HRP20020696A2 - 3-aminoquinazolin-2,4-dione antibakterial agents - Google Patents

3-aminoquinazolin-2,4-dione antibakterial agents Download PDF

Info

Publication number: HRP20020696A2
Authority: HR; Croatia
Prior art keywords: amino; cyclopropyl; dione; fluoro; quinazoline
Prior art date: 2000-01-24

Application number

HR20020696A

Other languages

English (en)

Croatian (hr)

Inventor

Paul Bird

Edmund Lee Ellsworth

Dai Quoc Nguyen

Joseph Peter Sanchez

Howard Daniel Hollis Showalter

Rajeshwar Singh

Michael Andrew Stier

Tuan Phong Tran

Brian Morgan Watson

Judy Yip

Original Assignee

Warner Lambert Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2000-01-24

Filing date

2002-08-23

Publication date

2003-12-31

2002-08-23 Application filed by Warner Lambert Co filed Critical Warner Lambert Co

2003-12-31 Publication of HRP20020696A2 publication Critical patent/HRP20020696A2/hr

Links

NMGODFWGUBLTTA-UHFFFAOYSA-N 3-amino-1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)N(N)C(=O)NC2=C1 NMGODFWGUBLTTA-UHFFFAOYSA-N 0.000 title description 14
-1 where n is 0 or 1 Chemical group 0.000 claims description 366
238000000034 method Methods 0.000 claims description 353
150000001875 compounds Chemical class 0.000 claims description 287
125000000623 heterocyclic group Chemical group 0.000 claims description 48
125000003118 aryl group Chemical group 0.000 claims description 46
125000000547 substituted alkyl group Chemical group 0.000 claims description 42
125000005843 halogen group Chemical group 0.000 claims description 33
125000001072 heteroaryl group Chemical group 0.000 claims description 31
229910052757 nitrogen Inorganic materials 0.000 claims description 31
125000005017 substituted alkenyl group Chemical group 0.000 claims description 31
125000004426 substituted alkynyl group Chemical group 0.000 claims description 31
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 23
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 23
241000124008 Mammalia Species 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 21
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
239000004202 carbamide Substances 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
229910052717 sulfur Inorganic materials 0.000 claims description 13
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 12
208000035143 Bacterial infection Diseases 0.000 claims description 11
208000022362 bacterial infectious disease Diseases 0.000 claims description 11
125000005842 heteroatom Chemical group 0.000 claims description 11
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 claims description 10
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 10
239000003085 diluting agent Substances 0.000 claims description 10
229910052760 oxygen Inorganic materials 0.000 claims description 10
239000000546 pharmaceutical excipient Substances 0.000 claims description 9
125000003107 substituted aryl group Chemical group 0.000 claims description 9
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 9
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
108010054814 DNA Gyrase Proteins 0.000 claims description 7
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 7
125000004122 cyclic group Chemical group 0.000 claims description 7
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 7
125000004429 atom Chemical group 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
ZRLLSDAIVJNZMQ-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 ZRLLSDAIVJNZMQ-UHFFFAOYSA-N 0.000 claims description 5
230000002401 inhibitory effect Effects 0.000 claims description 5
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 5
SPECGCDSMBDLBR-UHFFFAOYSA-N 1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidine-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)=O)C1 SPECGCDSMBDLBR-UHFFFAOYSA-N 0.000 claims description 4
WTYPWMXNMZPJCE-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)azetidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C1 WTYPWMXNMZPJCE-UHFFFAOYSA-N 0.000 claims description 4
JASKKDJDJMQUCW-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)CC1 JASKKDJDJMQUCW-UHFFFAOYSA-N 0.000 claims description 4
REQQVRNKRVUMLG-UHFFFAOYSA-N 1-(3-amino-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)piperidine-3-carboxamide Chemical compound C1C(C(=O)N)CCCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl REQQVRNKRVUMLG-UHFFFAOYSA-N 0.000 claims description 3
NUZLMAGOIPFPSG-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)(C)O)C1 NUZLMAGOIPFPSG-UHFFFAOYSA-N 0.000 claims description 3
XJPMPMISIRYKGH-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(C)(C)O)C1 XJPMPMISIRYKGH-UHFFFAOYSA-N 0.000 claims description 3
IXDMETOHGBEQQB-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1C2C(N)C2CN1C(C(=CC=1C(=O)N(N)C2=O)F)=NC=1N2C1CC1 IXDMETOHGBEQQB-UHFFFAOYSA-N 0.000 claims description 3
LFARSGUVNIPJGM-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)(CN)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 LFARSGUVNIPJGM-UHFFFAOYSA-N 0.000 claims description 3
YWYGZFKUTIQGCL-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-(3-hydroxyiminopyrrolidin-1-yl)quinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(CC3)=NO)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 YWYGZFKUTIQGCL-UHFFFAOYSA-N 0.000 claims description 3
CLKAGUACIOUJAC-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-7-(2,7-diazaspiro[4.4]nonan-2-yl)-6-fluoroquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC4(CNCC4)CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 CLKAGUACIOUJAC-UHFFFAOYSA-N 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
PFSZPRDGUQBIJS-LURJTMIESA-N 3,5-diamino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C(N)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F PFSZPRDGUQBIJS-LURJTMIESA-N 0.000 claims description 2
OLCPOZCJEAXMFQ-UHFFFAOYSA-N 3,8-diamino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-5-methylquinazoline-2,4-dione Chemical compound C1C(C(N)C)CCN1C1=CC(C)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1N OLCPOZCJEAXMFQ-UHFFFAOYSA-N 0.000 claims description 2
HKNHNFKDEOQGLZ-UHFFFAOYSA-N 3,8-diamino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione Chemical compound C1C(C(N)C)CCN1C1=C(F)C(C)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1N HKNHNFKDEOQGLZ-UHFFFAOYSA-N 0.000 claims description 2
GTRJJQDFRZCWKQ-NXEZZACHSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[(3r)-3-[(1r)-1-(methylamino)ethyl]pyrrolidin-1-yl]pyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@H]([C@@H](C)NC)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 GTRJJQDFRZCWKQ-NXEZZACHSA-N 0.000 claims description 2
KGBQXGXVBHFICV-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-[3-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CNC(C)C)C1 KGBQXGXVBHFICV-UHFFFAOYSA-N 0.000 claims description 2
VLVSORUTOYXYIG-UHFFFAOYSA-N 3-amino-7-(2-amino-5-azaspiro[2.4]heptan-5-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC21CC2N VLVSORUTOYXYIG-UHFFFAOYSA-N 0.000 claims description 2
QBAYAKOQUGQOHL-UHFFFAOYSA-N 3-amino-7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(N)C1 QBAYAKOQUGQOHL-UHFFFAOYSA-N 0.000 claims description 2
ONJJNQNMGCKRBJ-UHFFFAOYSA-N 3-amino-7-(3-amino-3-phenylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(N)C1=CC=CC=C1 ONJJNQNMGCKRBJ-UHFFFAOYSA-N 0.000 claims description 2
NICJESYMFMNVRX-UHFFFAOYSA-N 3-amino-7-(3-amino-3-phenylpyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(N)(CC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 NICJESYMFMNVRX-UHFFFAOYSA-N 0.000 claims description 2
MYNASXNPNLIHST-UHFFFAOYSA-N 3-amino-7-(3-amino-4-fluoropyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C(F)C1 MYNASXNPNLIHST-UHFFFAOYSA-N 0.000 claims description 2
LMKZWBWISAEVOS-UHFFFAOYSA-N 3-amino-7-(3-amino-4-methoxypyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(N)C(OC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC LMKZWBWISAEVOS-UHFFFAOYSA-N 0.000 claims description 2
SQVTZXOBPCVCIL-UHFFFAOYSA-N 3-amino-7-(3-amino-4-methoxypyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(N)C(OC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SQVTZXOBPCVCIL-UHFFFAOYSA-N 0.000 claims description 2
RHLHZJMDAZKSES-UHFFFAOYSA-N 3-amino-7-(3-aminoazetidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C1 RHLHZJMDAZKSES-UHFFFAOYSA-N 0.000 claims description 2
VPDDXYVQSVBBMT-UHFFFAOYSA-N 3-amino-7-(3-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(N)C1 VPDDXYVQSVBBMT-UHFFFAOYSA-N 0.000 claims description 2
SMRJEBDYHBYSSD-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-2,4-dioxoquinazoline-8-carbonitrile Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C#N SMRJEBDYHBYSSD-UHFFFAOYSA-N 0.000 claims description 2
YKTNCTISKOJENP-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione Chemical compound O=C1N(N)C(=O)C=2C(C)=C(F)C(N3CC(N)CC3)=CC=2N1C1CC1 YKTNCTISKOJENP-UHFFFAOYSA-N 0.000 claims description 2
JFMXVEXEGIJVCH-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 JFMXVEXEGIJVCH-UHFFFAOYSA-N 0.000 claims description 2
APNFNASNMSAHKF-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(N)C1 APNFNASNMSAHKF-UHFFFAOYSA-N 0.000 claims description 2
MBXPBQAHLCCZOV-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoroquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OCC)=C1N1CCC(N)C1 MBXPBQAHLCCZOV-UHFFFAOYSA-N 0.000 claims description 2
NLGWNSVFUWNXQX-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoro-6-methoxyquinazoline-2,4-dione Chemical compound COC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(F)=C1N1CCC(N)C1 NLGWNSVFUWNXQX-UHFFFAOYSA-N 0.000 claims description 2
AEVLVLQRERPDHR-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F AEVLVLQRERPDHR-UHFFFAOYSA-N 0.000 claims description 2
GXQRPAGCOKWOTA-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-6-chloro-1-cyclopropyl-8-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=C(Cl)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F GXQRPAGCOKWOTA-UHFFFAOYSA-N 0.000 claims description 2
LXAOHWSBPOQFAW-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-(cyclobutylamino)-6-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CCC3)C2=C1Cl LXAOHWSBPOQFAW-UHFFFAOYSA-N 0.000 claims description 2
IZSIJRQLAKGNBV-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl IZSIJRQLAKGNBV-UHFFFAOYSA-N 0.000 claims description 2
GKVGMICZIRZYHZ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-6-fluoro-1-propan-2-ylquinazoline-2,4-dione Chemical compound FC=1C=C2C(=O)N(N)C(=O)N(C(C)C)C2=C(Cl)C=1N1CCC(N)C1 GKVGMICZIRZYHZ-UHFFFAOYSA-N 0.000 claims description 2
UFFBMSWIXMBGJA-UHFFFAOYSA-N 3-amino-7-(4-aminopiperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)CC1 UFFBMSWIXMBGJA-UHFFFAOYSA-N 0.000 claims description 2
USGOLBXMHMCSCB-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3C(N)C3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 USGOLBXMHMCSCB-UHFFFAOYSA-N 0.000 claims description 2
SETCPIXEEMNUEB-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C2C(N)C2CN1C(C=1Cl)=C(F)C=C(C(N(N)C2=O)=O)C=1N2C1CC1 SETCPIXEEMNUEB-UHFFFAOYSA-N 0.000 claims description 2
FZFXKOVOWBGKLJ-GFCCVEGCSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione Chemical compound C1[C@H](C(C)(N)C)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F FZFXKOVOWBGKLJ-GFCCVEGCSA-N 0.000 claims description 2
UOCLUTIPDCTUDR-SECBINFHSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@H](C(C)(N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 UOCLUTIPDCTUDR-SECBINFHSA-N 0.000 claims description 2
GSIKINSTFPRFLI-SNVBAGLBSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-ethyl-6-fluoroquinazoline-2,4-dione Chemical compound FC=1C=C2C(=O)N(N)C(=O)N(CC)C2=CC=1N1CC[C@@H](C(C)(C)N)C1 GSIKINSTFPRFLI-SNVBAGLBSA-N 0.000 claims description 2
JGYNWRYCSYCVFZ-ABAIWWIYSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JGYNWRYCSYCVFZ-ABAIWWIYSA-N 0.000 claims description 2
DGGJUSQBQMQVCO-WBMJQRKESA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C DGGJUSQBQMQVCO-WBMJQRKESA-N 0.000 claims description 2
WAKUORIXGDVWOW-KUHUBIRLSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WAKUORIXGDVWOW-KUHUBIRLSA-N 0.000 claims description 2
QWFJOUZUSNZNMP-QRWLVFNGSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 QWFJOUZUSNZNMP-QRWLVFNGSA-N 0.000 claims description 2
JWSVHFMSXBFEGF-IAQYHMDHSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JWSVHFMSXBFEGF-IAQYHMDHSA-N 0.000 claims description 2
HTJVBSQZMOTMTA-MLGOLLRUSA-N 3-amino-7-[(3r)-3-[(1r)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HTJVBSQZMOTMTA-MLGOLLRUSA-N 0.000 claims description 2
JGYNWRYCSYCVFZ-IAQYHMDHSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JGYNWRYCSYCVFZ-IAQYHMDHSA-N 0.000 claims description 2
DGGJUSQBQMQVCO-MLGOLLRUSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-ethoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](N)COCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C DGGJUSQBQMQVCO-MLGOLLRUSA-N 0.000 claims description 2
WAKUORIXGDVWOW-AUUYWEPGSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WAKUORIXGDVWOW-AUUYWEPGSA-N 0.000 claims description 2
QWFJOUZUSNZNMP-FOIQADDNSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-2-phenoxyethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1CCN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 QWFJOUZUSNZNMP-FOIQADDNSA-N 0.000 claims description 2
JWSVHFMSXBFEGF-ABAIWWIYSA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JWSVHFMSXBFEGF-ABAIWWIYSA-N 0.000 claims description 2
HTJVBSQZMOTMTA-WBMJQRKESA-N 3-amino-7-[(3r)-3-[(1s)-1-amino-3-methoxypropyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@@H](N)CCOC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HTJVBSQZMOTMTA-WBMJQRKESA-N 0.000 claims description 2
PWBWMMRYCDDDSD-DTWKUNHWSA-N 3-amino-7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@H]([C@@H](N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 PWBWMMRYCDDDSD-DTWKUNHWSA-N 0.000 claims description 2
DLJALTOFOUWOSY-AAEUAGOBSA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@H](F)[C@@H](C(C)(C)N)C1 DLJALTOFOUWOSY-AAEUAGOBSA-N 0.000 claims description 2
PSKJYUUFNGTWRT-JSGCOSHPSA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1C[C@H](F)[C@@H](C(C)(C)N)C1 PSKJYUUFNGTWRT-JSGCOSHPSA-N 0.000 claims description 2
SFTNKLNSKHZSIS-STQMWFEESA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SFTNKLNSKHZSIS-STQMWFEESA-N 0.000 claims description 2
SZRPGPJRTBWAQC-KBPBESRZSA-N 3-amino-7-[(3r,4r)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SZRPGPJRTBWAQC-KBPBESRZSA-N 0.000 claims description 2
FQEJJUYPFJSYTM-AEGPPILISA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FQEJJUYPFJSYTM-AEGPPILISA-N 0.000 claims description 2
WCWSUFKBVHIJCI-CWRNSKLLSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WCWSUFKBVHIJCI-CWRNSKLLSA-N 0.000 claims description 2
BIXIMKDTYJERQW-SOUVJXGZSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC BIXIMKDTYJERQW-SOUVJXGZSA-N 0.000 claims description 2
QCDOITHYWYGQQG-HRCADAONSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QCDOITHYWYGQQG-HRCADAONSA-N 0.000 claims description 2
WSNNNRWCTBIJLR-HZUKXOBISA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WSNNNRWCTBIJLR-HZUKXOBISA-N 0.000 claims description 2
JMZBLZXEJZISCQ-XNJJOIOASA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JMZBLZXEJZISCQ-XNJJOIOASA-N 0.000 claims description 2
WTYRDLVCSKPCMR-VBNZEHGJSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WTYRDLVCSKPCMR-VBNZEHGJSA-N 0.000 claims description 2
NIHCENZIYVQPQI-AFAVFJNCSA-N 3-amino-7-[(3r,4r)-3-[(1r)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NIHCENZIYVQPQI-AFAVFJNCSA-N 0.000 claims description 2
RMERSVKMJNOJBM-AEGPPILISA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC RMERSVKMJNOJBM-AEGPPILISA-N 0.000 claims description 2
YVNCLSOUFPUSBG-CWRNSKLLSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YVNCLSOUFPUSBG-CWRNSKLLSA-N 0.000 claims description 2
MOZUHBQCTICBJN-SOUVJXGZSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MOZUHBQCTICBJN-SOUVJXGZSA-N 0.000 claims description 2
WMMXZMSWPCDHCH-HRCADAONSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WMMXZMSWPCDHCH-HRCADAONSA-N 0.000 claims description 2
JNBFVIXMWYHESF-HZUKXOBISA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JNBFVIXMWYHESF-HZUKXOBISA-N 0.000 claims description 2
FVHCULAQBOQUHE-XNJJOIOASA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FVHCULAQBOQUHE-XNJJOIOASA-N 0.000 claims description 2
WXEULHODWRFMJL-VBNZEHGJSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WXEULHODWRFMJL-VBNZEHGJSA-N 0.000 claims description 2
YMLACVZZOGDLOE-AFAVFJNCSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YMLACVZZOGDLOE-AFAVFJNCSA-N 0.000 claims description 2
KAYKDFPFMATDAL-FPMFFAJLSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC KAYKDFPFMATDAL-FPMFFAJLSA-N 0.000 claims description 2
BXAJEQNNGNFGRI-AEGPPILISA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXAJEQNNGNFGRI-AEGPPILISA-N 0.000 claims description 2
FINKNCVICOYUPZ-MELADBBJSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FINKNCVICOYUPZ-MELADBBJSA-N 0.000 claims description 2
UQDOBNTYFUNMNV-SOUVJXGZSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](F)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UQDOBNTYFUNMNV-SOUVJXGZSA-N 0.000 claims description 2
HWEFAWYJNKYDOP-VZJVUDMVSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC HWEFAWYJNKYDOP-VZJVUDMVSA-N 0.000 claims description 2
CQINKMNYHQLMPR-JMPLFQLZSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CQINKMNYHQLMPR-JMPLFQLZSA-N 0.000 claims description 2
JUHGKXCYUJZZLC-TUKIKUTGSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JUHGKXCYUJZZLC-TUKIKUTGSA-N 0.000 claims description 2
QTWRUBAFBNVEBZ-KNXALSJPSA-N 3-amino-7-[(3r,4r)-3-[(1s)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@H](C)[C@@H]([C@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QTWRUBAFBNVEBZ-KNXALSJPSA-N 0.000 claims description 2
DLJALTOFOUWOSY-WCQYABFASA-N 3-amino-7-[(3r,4s)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@@H](C(C)(C)N)C1 DLJALTOFOUWOSY-WCQYABFASA-N 0.000 claims description 2
PSKJYUUFNGTWRT-GXTWGEPZSA-N 3-amino-7-[(3r,4s)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1C[C@@H](F)[C@@H](C(C)(C)N)C1 PSKJYUUFNGTWRT-GXTWGEPZSA-N 0.000 claims description 2
SFTNKLNSKHZSIS-QWHCGFSZSA-N 3-amino-7-[(3r,4s)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SFTNKLNSKHZSIS-QWHCGFSZSA-N 0.000 claims description 2
SZRPGPJRTBWAQC-UONOGXRCSA-N 3-amino-7-[(3r,4s)-3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@H](F)C2)C(C)(C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SZRPGPJRTBWAQC-UONOGXRCSA-N 0.000 claims description 2
KCNSFBLKYSGMEW-LDYMZIIASA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](CN)[C@H](C(F)(F)F)C1 KCNSFBLKYSGMEW-LDYMZIIASA-N 0.000 claims description 2
SUCBAXXOPKUWKE-GMSGAONNSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@@H](C(F)(F)F)[C@H](CN)CN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 SUCBAXXOPKUWKE-GMSGAONNSA-N 0.000 claims description 2
ZDZWWQMQJYXBNK-PRHODGIISA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@H](CN)C1 ZDZWWQMQJYXBNK-PRHODGIISA-N 0.000 claims description 2
URQPIPYFJOGMNV-NXEZZACHSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](CN)C1 URQPIPYFJOGMNV-NXEZZACHSA-N 0.000 claims description 2
BZQFKQGLRYJYFN-MWLCHTKSSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BZQFKQGLRYJYFN-MWLCHTKSSA-N 0.000 claims description 2
UMPSZZBKTQMQJD-RKDXNWHRSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl UMPSZZBKTQMQJD-RKDXNWHRSA-N 0.000 claims description 2
RMERSVKMJNOJBM-CFVMTHIKSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC RMERSVKMJNOJBM-CFVMTHIKSA-N 0.000 claims description 2
YVNCLSOUFPUSBG-IMJJTQAJSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YVNCLSOUFPUSBG-IMJJTQAJSA-N 0.000 claims description 2
MOZUHBQCTICBJN-ZNMIVQPWSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MOZUHBQCTICBJN-ZNMIVQPWSA-N 0.000 claims description 2
WMMXZMSWPCDHCH-XHSDSOJGSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WMMXZMSWPCDHCH-XHSDSOJGSA-N 0.000 claims description 2
JNBFVIXMWYHESF-WPGHFRTFSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JNBFVIXMWYHESF-WPGHFRTFSA-N 0.000 claims description 2
FVHCULAQBOQUHE-PJQXDXOGSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FVHCULAQBOQUHE-PJQXDXOGSA-N 0.000 claims description 2
WXEULHODWRFMJL-KCXAZCMYSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WXEULHODWRFMJL-KCXAZCMYSA-N 0.000 claims description 2
YMLACVZZOGDLOE-DQYPLSBCSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-ethoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YMLACVZZOGDLOE-DQYPLSBCSA-N 0.000 claims description 2
KAYKDFPFMATDAL-YUTCNCBUSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC KAYKDFPFMATDAL-YUTCNCBUSA-N 0.000 claims description 2
BXAJEQNNGNFGRI-CFVMTHIKSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXAJEQNNGNFGRI-CFVMTHIKSA-N 0.000 claims description 2
FINKNCVICOYUPZ-MJBXVCDLSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FINKNCVICOYUPZ-MJBXVCDLSA-N 0.000 claims description 2
UQDOBNTYFUNMNV-ZNMIVQPWSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UQDOBNTYFUNMNV-ZNMIVQPWSA-N 0.000 claims description 2
HWEFAWYJNKYDOP-DGFSRKRXSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC HWEFAWYJNKYDOP-DGFSRKRXSA-N 0.000 claims description 2
CQINKMNYHQLMPR-OOVXXXAESA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CQINKMNYHQLMPR-OOVXXXAESA-N 0.000 claims description 2
JUHGKXCYUJZZLC-UGFHNGPFSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC JUHGKXCYUJZZLC-UGFHNGPFSA-N 0.000 claims description 2
QTWRUBAFBNVEBZ-RLCCDNCMSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-methoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)COC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QTWRUBAFBNVEBZ-RLCCDNCMSA-N 0.000 claims description 2
NQPUKCYBHWTSMP-UHOSZYNNSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 NQPUKCYBHWTSMP-UHOSZYNNSA-N 0.000 claims description 2
CGZAJPLOVGTWQD-SXLOBPIMSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 CGZAJPLOVGTWQD-SXLOBPIMSA-N 0.000 claims description 2
AAMUVBRJTLUMSV-OTWHNJEPSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](F)C2)[C@@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 AAMUVBRJTLUMSV-OTWHNJEPSA-N 0.000 claims description 2
TXNCRGZHDIVKJN-ZCNNSNEGSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@H](F)C2)[C@@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 TXNCRGZHDIVKJN-ZCNNSNEGSA-N 0.000 claims description 2
WKLBQFDYSLDYMB-WNYOCNMUSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@@H]1[C@H](C)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WKLBQFDYSLDYMB-WNYOCNMUSA-N 0.000 claims description 2
VVEDUPLRSMQSNY-RFVSGWPVSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(C[C@H]1C)C=1C(=C2C(C(N(N)C(=O)N2C2CC2)=O)=CC=1F)C)OC1=CC=CC=C1 VVEDUPLRSMQSNY-RFVSGWPVSA-N 0.000 claims description 2
GJTHSOGLFZTWOA-XPGWFJOJSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](C)C2)[C@@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GJTHSOGLFZTWOA-XPGWFJOJSA-N 0.000 claims description 2
GYWQGQNXCURQEH-NQERJWCQSA-N 3-amino-7-[(3r,4s)-3-[(1r)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(C[C@H]1C)C=1C(=C2C(C(N(N)C(=O)N2C2CC2)=O)=CC=1)C)OC1=CC=CC=C1 GYWQGQNXCURQEH-NQERJWCQSA-N 0.000 claims description 2
NQPUKCYBHWTSMP-QXAKKESOSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 NQPUKCYBHWTSMP-QXAKKESOSA-N 0.000 claims description 2
CGZAJPLOVGTWQD-DFQSSKMNSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1[C@H](F)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 CGZAJPLOVGTWQD-DFQSSKMNSA-N 0.000 claims description 2
AAMUVBRJTLUMSV-IPMKNSEASA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](F)C2)[C@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 AAMUVBRJTLUMSV-IPMKNSEASA-N 0.000 claims description 2
TXNCRGZHDIVKJN-XUVXKRRUSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C[C@@H]([C@H](F)C2)[C@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 TXNCRGZHDIVKJN-XUVXKRRUSA-N 0.000 claims description 2
WKLBQFDYSLDYMB-HEFCMCLBSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@@H]1[C@H](C)CN(C1)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 WKLBQFDYSLDYMB-HEFCMCLBSA-N 0.000 claims description 2
GJTHSOGLFZTWOA-UIAACRFSSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](C)C2)[C@H](N)COC=2C=CC=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GJTHSOGLFZTWOA-UIAACRFSSA-N 0.000 claims description 2
GYWQGQNXCURQEH-GQWLDOHISA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-2-phenoxyethyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@H]1CN(C[C@H]1C)C=1C(=C2C(C(N(N)C(=O)N2C2CC2)=O)=CC=1)C)OC1=CC=CC=C1 GYWQGQNXCURQEH-GQWLDOHISA-N 0.000 claims description 2
FQEJJUYPFJSYTM-CFVMTHIKSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC FQEJJUYPFJSYTM-CFVMTHIKSA-N 0.000 claims description 2
WCWSUFKBVHIJCI-IMJJTQAJSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WCWSUFKBVHIJCI-IMJJTQAJSA-N 0.000 claims description 2
BIXIMKDTYJERQW-ZNMIVQPWSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC BIXIMKDTYJERQW-ZNMIVQPWSA-N 0.000 claims description 2
QCDOITHYWYGQQG-XHSDSOJGSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QCDOITHYWYGQQG-XHSDSOJGSA-N 0.000 claims description 2
WSNNNRWCTBIJLR-WPGHFRTFSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WSNNNRWCTBIJLR-WPGHFRTFSA-N 0.000 claims description 2
JMZBLZXEJZISCQ-PJQXDXOGSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JMZBLZXEJZISCQ-PJQXDXOGSA-N 0.000 claims description 2
WTYRDLVCSKPCMR-KCXAZCMYSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC WTYRDLVCSKPCMR-KCXAZCMYSA-N 0.000 claims description 2
NIHCENZIYVQPQI-DQYPLSBCSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-amino-3-methoxypropyl]-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](C)[C@@H]([C@@H](N)CCOC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NIHCENZIYVQPQI-DQYPLSBCSA-N 0.000 claims description 2
OWLKBDJHUBSXIQ-RLCGTCKNSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-aminoethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@@H]([C@H](C)N)C1 OWLKBDJHUBSXIQ-RLCGTCKNSA-N 0.000 claims description 2
VHLRVQRBLBRKBC-MRCXROJRSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-aminoethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@@H](F)[C@@H]([C@@H](N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C VHLRVQRBLBRKBC-MRCXROJRSA-N 0.000 claims description 2
DPVCHDCEWZUPRH-ZETCQYMHSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylamino)-5,8-difluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC(F)=C2C(=O)N(N)C(=O)N(NC3CC3)C2=C1F DPVCHDCEWZUPRH-ZETCQYMHSA-N 0.000 claims description 2
OPPWHAMEKGQMSO-ZETCQYMHSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylamino)-6,8-difluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CC3)C2=C1F OPPWHAMEKGQMSO-ZETCQYMHSA-N 0.000 claims description 2
XSKOMKHOPDOCTI-JTQLQIEISA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F XSKOMKHOPDOCTI-JTQLQIEISA-N 0.000 claims description 2
YWSUCUHCADKMQR-LURJTMIESA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C(F)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F YWSUCUHCADKMQR-LURJTMIESA-N 0.000 claims description 2
FKEICTOGGGAVEH-ZETCQYMHSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1[C@@H](N)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 FKEICTOGGGAVEH-ZETCQYMHSA-N 0.000 claims description 2
RFIZFCOQVQJHIT-QMMMGPOBSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 RFIZFCOQVQJHIT-QMMMGPOBSA-N 0.000 claims description 2
JPJSIIJEJSBWLK-QMMMGPOBSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-ethyl-8-fluoroquinazoline-2,4-dione Chemical compound C=1C=C2C(=O)N(N)C(=O)N(CC)C2=C(F)C=1N1CC[C@H](N)C1 JPJSIIJEJSBWLK-QMMMGPOBSA-N 0.000 claims description 2
MUHLIKWDGNBMTN-VIFPVBQESA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-8-chloro-1-(2,4-difluoroanilino)-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC=3C(=CC(F)=CC=3)F)C2=C1Cl MUHLIKWDGNBMTN-VIFPVBQESA-N 0.000 claims description 2
VBNKDDYHSBUCLM-GOEBONIOSA-N 3-amino-7-[(3s,4r)-3-amino-4-(4-hydroxyphenyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=C(O)C=C1 VBNKDDYHSBUCLM-GOEBONIOSA-N 0.000 claims description 2
ROTWRQJAWBQSOY-PSASIEDQSA-N 3-amino-7-[(3s,4r)-3-amino-4-(trifluoromethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1[C@@H](C(F)(F)F)[C@H](N)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl ROTWRQJAWBQSOY-PSASIEDQSA-N 0.000 claims description 2
RVXZTPKDGTVNSL-PRHODGIISA-N 3-amino-7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](N)C1 RVXZTPKDGTVNSL-PRHODGIISA-N 0.000 claims description 2
PQTPQNWFGHUDHR-GOEBONIOSA-N 3-amino-7-[(3s,4r)-3-amino-4-phenylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=CC=C1 PQTPQNWFGHUDHR-GOEBONIOSA-N 0.000 claims description 2
GMCPKAWGIVMLBF-ZBFHGGJFSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC GMCPKAWGIVMLBF-ZBFHGGJFSA-N 0.000 claims description 2
VBDSQUOHJPEUMO-WBVHZDCISA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C VBDSQUOHJPEUMO-WBVHZDCISA-N 0.000 claims description 2
RTOOKIGWHNEETL-CVEARBPZSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC RTOOKIGWHNEETL-CVEARBPZSA-N 0.000 claims description 2
QRNGWKNPJGFQPC-SJORKVTESA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-ethoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COCC)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QRNGWKNPJGFQPC-SJORKVTESA-N 0.000 claims description 2
MZNFGFBDNSMXIH-HIFRSBDPSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MZNFGFBDNSMXIH-HIFRSBDPSA-N 0.000 claims description 2
BXFDZZBOVBPDGX-ZBFHGGJFSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXFDZZBOVBPDGX-ZBFHGGJFSA-N 0.000 claims description 2
SCGINPRZWGNIJN-QUCCMNQESA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 SCGINPRZWGNIJN-QUCCMNQESA-N 0.000 claims description 2
XTGWCIGUYCKYEE-CTNGQTDRSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 XTGWCIGUYCKYEE-CTNGQTDRSA-N 0.000 claims description 2
XHJWTSVTXZXVAI-UXHICEINSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(C)(C)[C@@H]([C@@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 XHJWTSVTXZXVAI-UXHICEINSA-N 0.000 claims description 2
UOUBDUJSNOAUGB-RTWAWAEBSA-N 3-amino-7-[(4r)-4-[(1r)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(C)(C)[C@@H]([C@@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 UOUBDUJSNOAUGB-RTWAWAEBSA-N 0.000 claims description 2
MZNFGFBDNSMXIH-UKRRQHHQSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC MZNFGFBDNSMXIH-UKRRQHHQSA-N 0.000 claims description 2
BXFDZZBOVBPDGX-GDBMZVCRSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-methoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)[C@@H]([C@H](N)COC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXFDZZBOVBPDGX-GDBMZVCRSA-N 0.000 claims description 2
SCGINPRZWGNIJN-UYAOXDASSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)OC)OC1=CC=CC=C1 SCGINPRZWGNIJN-UYAOXDASSA-N 0.000 claims description 2
XTGWCIGUYCKYEE-TZIWHRDSSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C([C@@H](N)[C@H]1CN(CC1(C)C)C1=C(C2=C(C(N(N)C(=O)N2C2CC2)=O)C=C1F)C)OC1=CC=CC=C1 XTGWCIGUYCKYEE-TZIWHRDSSA-N 0.000 claims description 2
XHJWTSVTXZXVAI-WOJBJXKFSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(C)(C)[C@@H]([C@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 XHJWTSVTXZXVAI-WOJBJXKFSA-N 0.000 claims description 2
UOUBDUJSNOAUGB-NHCUHLMSSA-N 3-amino-7-[(4r)-4-[(1s)-1-amino-2-phenoxyethyl]-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(C)(C)[C@@H]([C@H](N)COC=3C=CC=CC=3)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 UOUBDUJSNOAUGB-NHCUHLMSSA-N 0.000 claims description 2
TWIRCKLBUNQVOF-LLVKDONJSA-N 3-amino-7-[(7s)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C([C@H]1N)N(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC11CC1 TWIRCKLBUNQVOF-LLVKDONJSA-N 0.000 claims description 2
YLJXHSMLHOQOQO-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C(C3CCCCC3C2)CN)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 YLJXHSMLHOQOQO-UHFFFAOYSA-N 0.000 claims description 2
SAXDOWIIPOHGJK-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-1,3,3a,4,5,6,7,7a-octahydroisoindol-2-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2C(C3CCCCC3C2)CN)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SAXDOWIIPOHGJK-UHFFFAOYSA-N 0.000 claims description 2
WZEFJJXSICOLBU-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3(CN)CC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 WZEFJJXSICOLBU-UHFFFAOYSA-N 0.000 claims description 2
GQDNXEYBOILUQI-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC3(CN)CC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GQDNXEYBOILUQI-UHFFFAOYSA-N 0.000 claims description 2
GTMSVWIYIYVALU-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=N1 GTMSVWIYIYVALU-UHFFFAOYSA-N 0.000 claims description 2
RXYNGNBFBLYGSY-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=N1 RXYNGNBFBLYGSY-UHFFFAOYSA-N 0.000 claims description 2
FEHIBOSQMNCPEA-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2N=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 FEHIBOSQMNCPEA-UHFFFAOYSA-N 0.000 claims description 2
RNKBXOPKFRJXLU-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2N=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 RNKBXOPKFRJXLU-UHFFFAOYSA-N 0.000 claims description 2
VLPCEPGNRLOKKI-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound S1C(CN)=NC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=C1 VLPCEPGNRLOKKI-UHFFFAOYSA-N 0.000 claims description 2
VGZXYHMCVGVCNU-UHFFFAOYSA-N 3-amino-7-[2-(aminomethyl)-1,3-thiazol-4-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound S1C(CN)=NC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2)Cl)=C1 VGZXYHMCVGVCNU-UHFFFAOYSA-N 0.000 claims description 2
MCNRVILVRXNFEW-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COCC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C MCNRVILVRXNFEW-UHFFFAOYSA-N 0.000 claims description 2
WIASPBIONPUBMS-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COCC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WIASPBIONPUBMS-UHFFFAOYSA-N 0.000 claims description 2
RJMVZYHGELRPCW-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COCC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C RJMVZYHGELRPCW-UHFFFAOYSA-N 0.000 claims description 2
WVGCPHLVGBIWQO-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COCC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WVGCPHLVGBIWQO-UHFFFAOYSA-N 0.000 claims description 2
FXWFMHCPNJKXRV-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COCC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FXWFMHCPNJKXRV-UHFFFAOYSA-N 0.000 claims description 2
JYTPZOFUDSEQLZ-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COCC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JYTPZOFUDSEQLZ-UHFFFAOYSA-N 0.000 claims description 2
UKCYMUVIAIBGCN-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)COCC)CCN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UKCYMUVIAIBGCN-UHFFFAOYSA-N 0.000 claims description 2
KOAOBZHRZZCYOO-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)COCC)CCN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C KOAOBZHRZZCYOO-UHFFFAOYSA-N 0.000 claims description 2
PBIQRYGYWPNSOC-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-ethoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)COCC)CCN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PBIQRYGYWPNSOC-UHFFFAOYSA-N 0.000 claims description 2
YTPFASONAAHNOG-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YTPFASONAAHNOG-UHFFFAOYSA-N 0.000 claims description 2
FKUXSJDSRQEGOR-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FKUXSJDSRQEGOR-UHFFFAOYSA-N 0.000 claims description 2
JTQIFMBURAIWOK-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)COC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C JTQIFMBURAIWOK-UHFFFAOYSA-N 0.000 claims description 2
CZZQRAFHQVAXKC-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CZZQRAFHQVAXKC-UHFFFAOYSA-N 0.000 claims description 2
USOBMQHLJRHNHP-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C USOBMQHLJRHNHP-UHFFFAOYSA-N 0.000 claims description 2
RGTJHADPUQZPAB-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)COC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C RGTJHADPUQZPAB-UHFFFAOYSA-N 0.000 claims description 2
NLBOGRPLEXDCAN-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C(C)OC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NLBOGRPLEXDCAN-UHFFFAOYSA-N 0.000 claims description 2
GSNGUCUBKBUSIT-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C(C)OC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C GSNGUCUBKBUSIT-UHFFFAOYSA-N 0.000 claims description 2
HVMUQYPJHVLDFX-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C(C)OC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HVMUQYPJHVLDFX-UHFFFAOYSA-N 0.000 claims description 2
FGNJSINCCBWGKM-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)C(C)OC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C FGNJSINCCBWGKM-UHFFFAOYSA-N 0.000 claims description 2
PPKGGFYLRDMPDU-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)C(C)OC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PPKGGFYLRDMPDU-UHFFFAOYSA-N 0.000 claims description 2
NIPRWNSBKFLTLK-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)C(C(N)C(C)OC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NIPRWNSBKFLTLK-UHFFFAOYSA-N 0.000 claims description 2
IVRACUCUDYVUFK-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)C(C)OC)CCN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C IVRACUCUDYVUFK-UHFFFAOYSA-N 0.000 claims description 2
KNVIEJDUABRWNZ-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)C(C)OC)CCN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C KNVIEJDUABRWNZ-UHFFFAOYSA-N 0.000 claims description 2
HCYKRKVCTRDJIX-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-methoxypropyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C(N)C(C)OC)CCN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HCYKRKVCTRDJIX-UHFFFAOYSA-N 0.000 claims description 2
GIJSTEQVJBEVIB-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound FC1=NC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(F)C1C(N)COC1=CC=CC=C1 GIJSTEQVJBEVIB-UHFFFAOYSA-N 0.000 claims description 2
HNLFBZMCUGLSSV-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C(F)C2)C(N)COC=2C=CC=CC=2)C=NC(C(N(N)C2=O)=O)=C1N2C1CC1 HNLFBZMCUGLSSV-UHFFFAOYSA-N 0.000 claims description 2
VWECUHYVXMUQNJ-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C(F)C2)C(N)COC=2C=CC=CC=2)N=CC(C(N(N)C2=O)=O)=C1N2C1CC1 VWECUHYVXMUQNJ-UHFFFAOYSA-N 0.000 claims description 2
UUQNJAPPAKVUAJ-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=NC=2F)C)CC1C(N)COC1=CC=CC=C1 UUQNJAPPAKVUAJ-UHFFFAOYSA-N 0.000 claims description 2
YRHAJMYFXPKAKY-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=NC=2)C)CC1C(N)COC1=CC=CC=C1 YRHAJMYFXPKAKY-UHFFFAOYSA-N 0.000 claims description 2
AXBALEBUMDJPTA-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CN=2)C)CC1C(N)COC1=CC=CC=C1 AXBALEBUMDJPTA-UHFFFAOYSA-N 0.000 claims description 2
XLCAWRBBNAPVNM-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound FC1=NC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1C(N)COC1=CC=CC=C1 XLCAWRBBNAPVNM-UHFFFAOYSA-N 0.000 claims description 2
VMUWOJIAZFRLQI-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(CC2)C(N)COC=2C=CC=CC=2)C=NC(C(N(N)C2=O)=O)=C1N2C1CC1 VMUWOJIAZFRLQI-UHFFFAOYSA-N 0.000 claims description 2
UBWYHZMRRKOYGJ-UHFFFAOYSA-N 3-amino-7-[3-(1-amino-2-phenoxyethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(CC2)C(N)COC=2C=CC=CC=2)N=CC(C(N(N)C2=O)=O)=C1N2C1CC1 UBWYHZMRRKOYGJ-UHFFFAOYSA-N 0.000 claims description 2
CFMWTONEDJGNEA-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-3-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(F)(C(C)N)C1 CFMWTONEDJGNEA-UHFFFAOYSA-N 0.000 claims description 2
QYHNCGDAXNRFGY-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-3-methoxypyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(OC)(C(C)N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QYHNCGDAXNRFGY-UHFFFAOYSA-N 0.000 claims description 2
NPEQTLBTOLZKFH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NPEQTLBTOLZKFH-UHFFFAOYSA-N 0.000 claims description 2
ZBLCSRAYXXNYGY-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C ZBLCSRAYXXNYGY-UHFFFAOYSA-N 0.000 claims description 2
UXJUCUCJFDROJE-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(F)C(C(N)C)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UXJUCUCJFDROJE-UHFFFAOYSA-N 0.000 claims description 2
ZFFKHRCQSMRYSW-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C)C(C(C)N)C1 ZFFKHRCQSMRYSW-UHFFFAOYSA-N 0.000 claims description 2
AXBNANCXFLNTPV-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C AXBNANCXFLNTPV-UHFFFAOYSA-N 0.000 claims description 2
KURNMRMNDDYRKZ-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(C(C)N)C1 KURNMRMNDDYRKZ-UHFFFAOYSA-N 0.000 claims description 2
GPKXDBZXFOCAJT-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(C(N)C)CCN1C1=CC(C)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C GPKXDBZXFOCAJT-UHFFFAOYSA-N 0.000 claims description 2
CZCYAKDNGWYMBC-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5,8-dimethylquinazoline-2,4-dione Chemical compound C1C(C(N)C)CCN1C(C(=C1C)F)=C(C)C2=C1C(=O)N(N)C(=O)N2C1CC1 CZCYAKDNGWYMBC-UHFFFAOYSA-N 0.000 claims description 2
PXDQRBZQWZZZNR-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound FC1=C(C)C(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)N)C1 PXDQRBZQWZZZNR-UHFFFAOYSA-N 0.000 claims description 2
WOVLHNXJEKPFRK-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)pyrrolidin-1-yl]-1-cyclopropyl-8-methoxy-5-methylquinazoline-2,4-dione Chemical compound COC1=C(N2CC(CC2)C(C)N)C=C(C)C(C(N(N)C2=O)=O)=C1N2C1CC1 WOVLHNXJEKPFRK-UHFFFAOYSA-N 0.000 claims description 2
HYSNAXRDIFGYKO-UHFFFAOYSA-N 3-amino-7-[3-(1-aminopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C(N)CC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C HYSNAXRDIFGYKO-UHFFFAOYSA-N 0.000 claims description 2
UDZZMBWUJRMXKG-UHFFFAOYSA-N 3-amino-7-[3-(2-aminoethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC(CCN)C1 UDZZMBWUJRMXKG-UHFFFAOYSA-N 0.000 claims description 2
HITXXKABPONDNP-UHFFFAOYSA-N 3-amino-7-[3-(2-aminoethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(CCN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl HITXXKABPONDNP-UHFFFAOYSA-N 0.000 claims description 2
VWHUEMGFIDMTDV-UHFFFAOYSA-N 3-amino-7-[3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound FC1=NC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(F)C(C(C)(C)N)C1 VWHUEMGFIDMTDV-UHFFFAOYSA-N 0.000 claims description 2
DKXIYYJQZUNVGA-UHFFFAOYSA-N 3-amino-7-[3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C(F)C2)C(C)(C)N)C=NC(C(N(N)C2=O)=O)=C1N2C1CC1 DKXIYYJQZUNVGA-UHFFFAOYSA-N 0.000 claims description 2
DIPPDJOOYUFWLO-UHFFFAOYSA-N 3-amino-7-[3-(2-aminopropan-2-yl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C(F)C2)C(C)(C)N)N=CC(C(N(N)C2=O)=O)=C1N2C1CC1 DIPPDJOOYUFWLO-UHFFFAOYSA-N 0.000 claims description 2
NDRNJXYVSWVSNG-UHFFFAOYSA-N 3-amino-7-[3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)(C)N)C1 NDRNJXYVSWVSNG-UHFFFAOYSA-N 0.000 claims description 2
VGEJBOUMCFOLLC-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(CN)(CF)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 VGEJBOUMCFOLLC-UHFFFAOYSA-N 0.000 claims description 2
RPBSNJWGNSKHOM-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-(methoxymethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(COC)(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C RPBSNJWGNSKHOM-UHFFFAOYSA-N 0.000 claims description 2
YGKAPMCVYQSGRM-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-benzylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC1(CN)CC1=CC=CC=C1 YGKAPMCVYQSGRM-UHFFFAOYSA-N 0.000 claims description 2
IIGRIZUDZAXUNS-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-hydroxypyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)(CN)C1 IIGRIZUDZAXUNS-UHFFFAOYSA-N 0.000 claims description 2
VQSODMXYBKLVDH-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C)(CN)C1 VQSODMXYBKLVDH-UHFFFAOYSA-N 0.000 claims description 2
XOYHKQSGPPTWAD-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(CN)C1 XOYHKQSGPPTWAD-UHFFFAOYSA-N 0.000 claims description 2
FDPXWWAQMWLPDR-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(C)(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl FDPXWWAQMWLPDR-UHFFFAOYSA-N 0.000 claims description 2
JKSLNRWNPCBWAT-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-phenylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(CN)C1=CC=CC=C1 JKSLNRWNPCBWAT-UHFFFAOYSA-N 0.000 claims description 2
PFAJJDAMOIXZMN-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)phenyl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2C=C(CN)C=CC=2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 PFAJJDAMOIXZMN-UHFFFAOYSA-N 0.000 claims description 2
BKNGPKYIPVGISS-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)phenyl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2C=C(CN)C=CC=2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 BKNGPKYIPVGISS-UHFFFAOYSA-N 0.000 claims description 2
NNSUFMUPVLRTEA-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)phenyl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2C=C(CN)C=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 NNSUFMUPVLRTEA-UHFFFAOYSA-N 0.000 claims description 2
FVXLUEIOPNDQCM-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)phenyl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2C=C(CN)C=CC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 FVXLUEIOPNDQCM-UHFFFAOYSA-N 0.000 claims description 2
BWXHDANGZXHVDO-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)phenyl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound NCC1=CC=CC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=C1 BWXHDANGZXHVDO-UHFFFAOYSA-N 0.000 claims description 2
YADGFMPPTBRCNU-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)phenyl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound NCC1=CC=CC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2)Cl)=C1 YADGFMPPTBRCNU-UHFFFAOYSA-N 0.000 claims description 2
UTYJPVXOAGQZNS-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(CN)C1 UTYJPVXOAGQZNS-UHFFFAOYSA-N 0.000 claims description 2
DWELFMYWXKTTGT-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC(CN)C1 DWELFMYWXKTTGT-UHFFFAOYSA-N 0.000 claims description 2
KMOXXHGLMKCGRK-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C1C(CN)CCCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 KMOXXHGLMKCGRK-UHFFFAOYSA-N 0.000 claims description 2
GRBRTALESMNRJD-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(CN)CCCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl GRBRTALESMNRJD-UHFFFAOYSA-N 0.000 claims description 2
WWJJMIXOFUVRBI-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 WWJJMIXOFUVRBI-UHFFFAOYSA-N 0.000 claims description 2
YIVGSUPJSMHNEV-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(CN)C1 YIVGSUPJSMHNEV-UHFFFAOYSA-N 0.000 claims description 2
GNQIQERLAURHGP-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(CN)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 GNQIQERLAURHGP-UHFFFAOYSA-N 0.000 claims description 2
YGNPKMIIZKPZKU-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-6,8-dichloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(CN)CCN1C1=C(Cl)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl YGNPKMIIZKPZKU-UHFFFAOYSA-N 0.000 claims description 2
KHTSEDLVGMSKAJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl KHTSEDLVGMSKAJ-UHFFFAOYSA-N 0.000 claims description 2
OALBPTZREKXPIM-UHFFFAOYSA-N 3-amino-7-[3-amino-4-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C(CF)C1 OALBPTZREKXPIM-UHFFFAOYSA-N 0.000 claims description 2
KPEAZQRJPMJXJT-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-ethoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COCC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C KPEAZQRJPMJXJT-UHFFFAOYSA-N 0.000 claims description 2
SMDLSNLIQFGZQR-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-ethoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COCC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SMDLSNLIQFGZQR-UHFFFAOYSA-N 0.000 claims description 2
GRXRVQDLXPKRNU-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-ethoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COCC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C GRXRVQDLXPKRNU-UHFFFAOYSA-N 0.000 claims description 2
TZRXNTDEOOJEOX-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COC)CN1C1=C(F)N=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C TZRXNTDEOOJEOX-UHFFFAOYSA-N 0.000 claims description 2
PKBTXJAYWZVJJY-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COC)CN1C1=CN=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PKBTXJAYWZVJJY-UHFFFAOYSA-N 0.000 claims description 2
SYRCIDHXOSWLRM-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-methoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound C1C(C)(C)C(C(N)COC)CN1C1=NC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SYRCIDHXOSWLRM-UHFFFAOYSA-N 0.000 claims description 2
KIDXJJUVIKPCOD-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound FC1=NC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(CC1(C)C)CC1C(N)COC1=CC=CC=C1 KIDXJJUVIKPCOD-UHFFFAOYSA-N 0.000 claims description 2
QTXQQPOORDXHBQ-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[3,2-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C)(C)C(C(N)COC=3C=CC=CC=3)C2)C=NC(C(N(N)C2=O)=O)=C1N2C1CC1 QTXQQPOORDXHBQ-UHFFFAOYSA-N 0.000 claims description 2
VGWZEGVEGQPYNW-UHFFFAOYSA-N 3-amino-7-[4-(1-amino-2-phenoxyethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-8-methylpyrido[4,3-d]pyrimidine-2,4-dione Chemical compound CC1=C(N2CC(C)(C)C(C(N)COC=3C=CC=CC=3)C2)N=CC(C(N(N)C2=O)=O)=C1N2C1CC1 VGWZEGVEGQPYNW-UHFFFAOYSA-N 0.000 claims description 2
OPXSUSIFKCWAAZ-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(F)(F)C1 OPXSUSIFKCWAAZ-UHFFFAOYSA-N 0.000 claims description 2
ODGYFTKNQVXYPX-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C ODGYFTKNQVXYPX-UHFFFAOYSA-N 0.000 claims description 2
GVYDJTMGSWNLLQ-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(F)(F)C(C(C)N)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 GVYDJTMGSWNLLQ-UHFFFAOYSA-N 0.000 claims description 2
YSWSMAOIADXSJJ-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C YSWSMAOIADXSJJ-UHFFFAOYSA-N 0.000 claims description 2
SIPVOUZPSPRUAB-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl SIPVOUZPSPRUAB-UHFFFAOYSA-N 0.000 claims description 2
LURQEEMHISKSRX-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(N)C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl LURQEEMHISKSRX-UHFFFAOYSA-N 0.000 claims description 2
FXLFPNNYZRRJCG-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(C)(C)C1 FXLFPNNYZRRJCG-UHFFFAOYSA-N 0.000 claims description 2
WHVDJPHTVKCYDW-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1C(C)(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C WHVDJPHTVKCYDW-UHFFFAOYSA-N 0.000 claims description 2
RSCLUHGIBZKZFO-UHFFFAOYSA-N 3-amino-7-[4-(2-aminopropan-2-yl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(F)(F)C(C(C)(C)N)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 RSCLUHGIBZKZFO-UHFFFAOYSA-N 0.000 claims description 2
HJUIXGXPYMFZOH-UHFFFAOYSA-N 3-amino-7-[4-(2-aminopropan-2-yl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(F)(F)C(C(C)(C)N)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 HJUIXGXPYMFZOH-UHFFFAOYSA-N 0.000 claims description 2
QILKGBMFMDBJDG-UHFFFAOYSA-N 3-amino-7-[4-(2-aminopropan-2-yl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(C(C)(N)C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl QILKGBMFMDBJDG-UHFFFAOYSA-N 0.000 claims description 2
YJTLAGQFKMRSHQ-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C(F)(F)C1 YJTLAGQFKMRSHQ-UHFFFAOYSA-N 0.000 claims description 2
HVYIEAHRHFOQNA-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC(CN)C(F)(F)C1 HVYIEAHRHFOQNA-UHFFFAOYSA-N 0.000 claims description 2
VWQSCDFRKGGQGQ-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC(F)(F)C(CN)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 VWQSCDFRKGGQGQ-UHFFFAOYSA-N 0.000 claims description 2
LLQRSSCZBZXNKD-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(N2CC(F)(F)C(CN)C2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 LLQRSSCZBZXNKD-UHFFFAOYSA-N 0.000 claims description 2
UCDQJTZOFJBISG-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound C1C(F)(F)C(CN)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl UCDQJTZOFJBISG-UHFFFAOYSA-N 0.000 claims description 2
MMXUEEUSEQTGLI-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)-3,3-difluoropyrrolidin-1-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound C1C(F)(F)C(CN)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl MMXUEEUSEQTGLI-UHFFFAOYSA-N 0.000 claims description 2
RTILSMIWBOHCLQ-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1C1=CSC(CN)=C1 RTILSMIWBOHCLQ-UHFFFAOYSA-N 0.000 claims description 2
ZAURZWBNIZPUJO-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1C1=CSC(CN)=C1 ZAURZWBNIZPUJO-UHFFFAOYSA-N 0.000 claims description 2
PIXOZOYGPDFQRN-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(C=2C=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 PIXOZOYGPDFQRN-UHFFFAOYSA-N 0.000 claims description 2
BCBJQYLJYAALNN-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-1-cyclopropyl-8-methylquinazoline-2,4-dione Chemical compound CC1=C(C=2C=C(CN)SC=2)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 BCBJQYLJYAALNN-UHFFFAOYSA-N 0.000 claims description 2
MAXNCKAGFRGUGY-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione Chemical compound S1C(CN)=CC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=C1 MAXNCKAGFRGUGY-UHFFFAOYSA-N 0.000 claims description 2
GIKALOAWFNMZSD-UHFFFAOYSA-N 3-amino-7-[5-(aminomethyl)thiophen-3-yl]-8-chloro-1-cyclopropylquinazoline-2,4-dione Chemical compound S1C(CN)=CC(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2)Cl)=C1 GIKALOAWFNMZSD-UHFFFAOYSA-N 0.000 claims description 2
QAPRITTXNPCYSU-UHFFFAOYSA-N 3-amino-7-[7-(1-aminoethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound CC(N)C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)C)CC11CC1 QAPRITTXNPCYSU-UHFFFAOYSA-N 0.000 claims description 2
AINBVJBQTTZKNW-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(CN)C21CC2 AINBVJBQTTZKNW-UHFFFAOYSA-N 0.000 claims description 2
ASPRZCFYJNJRGE-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(CN)C21CC2 ASPRZCFYJNJRGE-UHFFFAOYSA-N 0.000 claims description 2
XHDGVTPMBJEXOC-QXXIUIOUSA-N 3-amino-8-[(3R)-3-[(1S)-1-aminoethyl]pyrrolidin-1-yl]-7-fluoro-12-methyl-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N3C(C)CCC1=C32 XHDGVTPMBJEXOC-QXXIUIOUSA-N 0.000 claims description 2
MFMDCVFUAGRPIL-CBMCFHRWSA-N 3-amino-8-[(3R)-3-[(1S)-1-aminoethyl]pyrrolidin-1-yl]-7-fluoro-12-methyl-10-oxa-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N3C(C)COC1=C32 MFMDCVFUAGRPIL-CBMCFHRWSA-N 0.000 claims description 2
LGBHTXIBLKBUKN-GKAPJAKFSA-N 3-amino-8-[(3S)-3-aminopyrrolidin-1-yl]-7-fluoro-12-methyl-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound FC1=CC(C(N(N)C2=O)=O)=C3N2C(C)CCC3=C1N1CC[C@H](N)C1 LGBHTXIBLKBUKN-GKAPJAKFSA-N 0.000 claims description 2
MQYWJXVDBHTHJE-MQWKRIRWSA-N 3-amino-8-[(3S)-3-aminopyrrolidin-1-yl]-7-fluoro-12-methyl-10-oxa-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound FC1=CC(C(N(N)C2=O)=O)=C3N2C(C)COC3=C1N1CC[C@H](N)C1 MQYWJXVDBHTHJE-MQWKRIRWSA-N 0.000 claims description 2
DTSFGOGGBWDFOX-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)quinazoline-2,4-dione Chemical compound C1C2CN(C)CC2CN1C(C=1Cl)=C(F)C=C(C(N(N)C2=O)=O)C=1N2C1CC1 DTSFGOGGBWDFOX-UHFFFAOYSA-N 0.000 claims description 2
UYELLIFHKILPAN-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(CO)CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 UYELLIFHKILPAN-UHFFFAOYSA-N 0.000 claims description 2
JFFKNWQKPVVSFQ-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C1C(CNC(C)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl JFFKNWQKPVVSFQ-UHFFFAOYSA-N 0.000 claims description 2
LEQNXEXZTCRROR-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-piperazin-1-ylquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CCNCC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 LEQNXEXZTCRROR-UHFFFAOYSA-N 0.000 claims description 2
RRTPRFUHVCSHRT-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CCCC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 RRTPRFUHVCSHRT-UHFFFAOYSA-N 0.000 claims description 2
PPWBBORVAVZKHU-UHFFFAOYSA-N 7-(1,3,3a,4,5,6,7,7a-octahydropyrrolo[3,4-c]pyridin-2-yl)-3-amino-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C12=NC(N3CC4CNCCC4C3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 PPWBBORVAVZKHU-UHFFFAOYSA-N 0.000 claims description 2
GTGRQHMVAQLFNN-UHFFFAOYSA-N 7-(2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridin-2-yl)-3-amino-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C12=NC(C3NC4CNCC4CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 GTGRQHMVAQLFNN-UHFFFAOYSA-N 0.000 claims description 2
QFJKMFIBXMYTMK-RNCFNFMXSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@@H]([C@@H](N)CNC(N)=O)C1 QFJKMFIBXMYTMK-RNCFNFMXSA-N 0.000 claims description 2
SAKXLGUKGULDTQ-YGRLFVJLSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@@H]([C@@H](N)CNC(N)=O)C1 SAKXLGUKGULDTQ-YGRLFVJLSA-N 0.000 claims description 2
SRWFLGFQKJBLMZ-MFKMUULPSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound COC1=C(N2C[C@@H](CC2)[C@@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SRWFLGFQKJBLMZ-MFKMUULPSA-N 0.000 claims description 2
BOAVHSIPQXSDQP-RISCZKNCSA-N [(2r)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound CC1=C(N2C[C@@H](CC2)[C@@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 BOAVHSIPQXSDQP-RISCZKNCSA-N 0.000 claims description 2
SOOAHHRQDBLUHM-LQJRIPTKSA-N [(2r)-2-amino-2-[(3r,4s)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@@H]([C@@H](N)CNC(N)=O)C1 SOOAHHRQDBLUHM-LQJRIPTKSA-N 0.000 claims description 2
CYMKJADKSGUUCQ-DVJZZOLTSA-N [(2r)-2-amino-2-[(3r,4s)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound C1[C@H]([C@@H](N)CNC(N)=O)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CYMKJADKSGUUCQ-DVJZZOLTSA-N 0.000 claims description 2
RBLVGNVIPIQVKY-SWHYSGLUSA-N [(2r)-2-amino-2-[(3r,4s)-1-(3-amino-1-cyclopropyl-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound COC1=C(N2C[C@@H]([C@H](C)C2)[C@@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 RBLVGNVIPIQVKY-SWHYSGLUSA-N 0.000 claims description 2
PJUXHXXITBWVGH-ONERCXAPSA-N [(2r)-2-amino-2-[(3r,4s)-1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound C1[C@H]([C@@H](N)CNC(N)=O)[C@H](C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PJUXHXXITBWVGH-ONERCXAPSA-N 0.000 claims description 2
QFJKMFIBXMYTMK-NOZJJQNGSA-N [(2s)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@@H]([C@H](N)CNC(N)=O)C1 QFJKMFIBXMYTMK-NOZJJQNGSA-N 0.000 claims description 2
SAKXLGUKGULDTQ-QMTHXVAHSA-N [(2s)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@@H]([C@H](N)CNC(N)=O)C1 SAKXLGUKGULDTQ-QMTHXVAHSA-N 0.000 claims description 2
SRWFLGFQKJBLMZ-ZWNOBZJWSA-N [(2s)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound COC1=C(N2C[C@@H](CC2)[C@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 SRWFLGFQKJBLMZ-ZWNOBZJWSA-N 0.000 claims description 2
BOAVHSIPQXSDQP-BXUZGUMPSA-N [(2s)-2-amino-2-[(3r)-1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]urea Chemical compound CC1=C(N2C[C@@H](CC2)[C@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 BOAVHSIPQXSDQP-BXUZGUMPSA-N 0.000 claims description 2
SOOAHHRQDBLUHM-DUFXMDAXSA-N [(2s)-2-amino-2-[(3r,4r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@H](C)[C@@H]([C@H](N)CNC(N)=O)C1 SOOAHHRQDBLUHM-DUFXMDAXSA-N 0.000 claims description 2
CYMKJADKSGUUCQ-DYQSUWPFSA-N [(2s)-2-amino-2-[(3r,4r)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound C1[C@H]([C@H](N)CNC(N)=O)[C@@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CYMKJADKSGUUCQ-DYQSUWPFSA-N 0.000 claims description 2
RBLVGNVIPIQVKY-LEWSCRJBSA-N [(2s)-2-amino-2-[(3r,4r)-1-(3-amino-1-cyclopropyl-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound COC1=C(N2C[C@@H]([C@@H](C)C2)[C@H](N)CNC(N)=O)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 RBLVGNVIPIQVKY-LEWSCRJBSA-N 0.000 claims description 2
PJUXHXXITBWVGH-NZVBXONLSA-N [(2s)-2-amino-2-[(3r,4r)-1-(3-amino-1-cyclopropyl-8-methyl-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethyl]urea Chemical compound C1[C@H]([C@H](N)CNC(N)=O)[C@@H](C)CN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C PJUXHXXITBWVGH-NZVBXONLSA-N 0.000 claims description 2
RPFFJRFAWHVIJK-UHFFFAOYSA-N n-[[1-(3-amino-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]methyl]methanesulfonamide Chemical compound C1C(CNS(=O)(=O)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl RPFFJRFAWHVIJK-UHFFFAOYSA-N 0.000 claims description 2
239000000825 pharmaceutical preparation Substances 0.000 claims 8
125000004193 piperazinyl group Chemical group 0.000 claims 2
UCJVXLRCPAIDEL-UHFFFAOYSA-N 3-amino-7-(4-amino-2,3-dihydropyrrol-1-yl)-1-butan-2-yl-8-chloro-6-fluoroquinazoline-2,4-dione Chemical compound FC=1C=C2C(=O)N(N)C(=O)N(C(C)CC)C2=C(Cl)C=1N1CCC(N)=C1 UCJVXLRCPAIDEL-UHFFFAOYSA-N 0.000 claims 1
DMVCNEPYSFWQBP-ZWKOPEQDSA-N 3-amino-7-[(3r,4s)-3-[(1s)-1-aminoethyl]-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2C[C@@H]([C@H](F)C2)[C@H](C)N)C=CC(C(N(N)C2=O)=O)=C1N2C1CC1 DMVCNEPYSFWQBP-ZWKOPEQDSA-N 0.000 claims 1
XZUDRAJEAHGSJN-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-[(2,2,2-trifluoroethylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C12=C(Cl)C(N3CC(CNCC(F)(F)F)CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 XZUDRAJEAHGSJN-UHFFFAOYSA-N 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 367
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 306
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 293
239000000243 solution Substances 0.000 description 207
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 153
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 144
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 142
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 119
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 114
235000019439 ethyl acetate Nutrition 0.000 description 102
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 94
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 84
238000005160 1H NMR spectroscopy Methods 0.000 description 83
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 81
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 69
239000000203 mixture Substances 0.000 description 65
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 64
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 64
238000006243 chemical reaction Methods 0.000 description 64
230000015572 biosynthetic process Effects 0.000 description 63
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 62
239000007787 solid Substances 0.000 description 62
239000012044 organic layer Substances 0.000 description 60
239000012266 salt solution Substances 0.000 description 60
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 59
239000011541 reaction mixture Substances 0.000 description 59
WJGKQOLBCQGWAL-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6,7-difluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(F)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 WJGKQOLBCQGWAL-UHFFFAOYSA-N 0.000 description 58
LFIVFMAMROTIED-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6,7-difluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(F)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 LFIVFMAMROTIED-UHFFFAOYSA-N 0.000 description 58
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 58
229910052943 magnesium sulfate Inorganic materials 0.000 description 57
235000019341 magnesium sulphate Nutrition 0.000 description 57
238000003786 synthesis reaction Methods 0.000 description 57
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
238000003818 flash chromatography Methods 0.000 description 48
229940086542 triethylamine Drugs 0.000 description 48
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 46
239000002904 solvent Substances 0.000 description 42
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 42
UEJLAUQTARPJTG-UHFFFAOYSA-N (8-chloro-1-cyclopropyl-6,7-difluoro-2,4-dioxoquinazolin-3-yl)carbamic acid Chemical compound C12=C(Cl)C(F)=C(F)C=C2C(=O)N(NC(=O)O)C(=O)N1C1CC1 UEJLAUQTARPJTG-UHFFFAOYSA-N 0.000 description 41
239000000706 filtrate Substances 0.000 description 39
239000002253 acid Substances 0.000 description 37
230000002829 reductive effect Effects 0.000 description 37
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 35
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 34
125000000217 alkyl group Chemical group 0.000 description 34
229910052938 sodium sulfate Inorganic materials 0.000 description 34
235000011152 sodium sulphate Nutrition 0.000 description 34
239000007832 Na2SO4 Substances 0.000 description 33
150000001412 amines Chemical class 0.000 description 32
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 32
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 31
WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 28
229960001760 dimethyl sulfoxide Drugs 0.000 description 28
239000002585 base Substances 0.000 description 27
125000006239 protecting group Chemical group 0.000 description 25
150000002148 esters Chemical class 0.000 description 24
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
235000010233 benzoic acid Nutrition 0.000 description 23
239000000284 extract Substances 0.000 description 21
VQNBCXNRVVLUKX-UHFFFAOYSA-N 3-amino-7-chloro-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C12=NC(Cl)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 VQNBCXNRVVLUKX-UHFFFAOYSA-N 0.000 description 19
239000000047 product Substances 0.000 description 19
238000010992 reflux Methods 0.000 description 19
239000005711 Benzoic acid Substances 0.000 description 18
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
150000001408 amides Chemical class 0.000 description 18
238000001914 filtration Methods 0.000 description 18
DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 18
SDQJTWBNWQABLE-UHFFFAOYSA-N 1h-quinazoline-2,4-dione Chemical compound C1=CC=C2C(=O)NC(=O)NC2=C1 SDQJTWBNWQABLE-UHFFFAOYSA-N 0.000 description 17
239000003921 oil Substances 0.000 description 17
239000003054 catalyst Substances 0.000 description 16
239000003153 chemical reaction reagent Substances 0.000 description 16
238000004440 column chromatography Methods 0.000 description 16
229910000104 sodium hydride Inorganic materials 0.000 description 16
125000004494 ethyl ester group Chemical group 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
125000001424 substituent group Chemical group 0.000 description 15
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 14
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 14
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 14
235000017557 sodium bicarbonate Nutrition 0.000 description 14
229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
239000012312 sodium hydride Substances 0.000 description 14
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 13
239000000543 intermediate Substances 0.000 description 13
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
229910052763 palladium Inorganic materials 0.000 description 12
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 12
150000007660 quinolones Chemical class 0.000 description 12
239000007858 starting material Substances 0.000 description 12
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 11
230000000844 anti-bacterial effect Effects 0.000 description 11
229910052794 bromium Inorganic materials 0.000 description 11
239000000460 chlorine Substances 0.000 description 11
239000002244 precipitate Substances 0.000 description 11
238000000746 purification Methods 0.000 description 11
JWKDABYXHUGBOR-UHFFFAOYSA-N tert-butyl n-amino-n-[2-(cyclopropylamino)-4,5-difluorobenzoyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC(F)=C(F)C=C1NC1CC1 JWKDABYXHUGBOR-UHFFFAOYSA-N 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 10
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical group C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
238000001816 cooling Methods 0.000 description 10
239000011521 glass Substances 0.000 description 10
239000012038 nucleophile Substances 0.000 description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
229910052801 chlorine Inorganic materials 0.000 description 9
229910052731 fluorine Inorganic materials 0.000 description 9
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
229910000041 hydrogen chloride Inorganic materials 0.000 description 9
229910052751 metal Inorganic materials 0.000 description 9
239000002184 metal Substances 0.000 description 9
238000003756 stirring Methods 0.000 description 9
ZAJMGFOHORRQHJ-ZJUUUORDSA-N [(1R)-1-[(3S)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]ethyl]carbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H](CC1)[C@@H](C)NC(O)=O)OC)C1CC1)=O ZAJMGFOHORRQHJ-ZJUUUORDSA-N 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
244000309464 bull Species 0.000 description 8
125000000753 cycloalkyl group Chemical group 0.000 description 8
239000007789 gas Substances 0.000 description 8
230000026030 halogenation Effects 0.000 description 8
238000005658 halogenation reaction Methods 0.000 description 8
150000003235 pyrrolidines Chemical class 0.000 description 8
CISXRFRLKWCFJS-UHFFFAOYSA-N 2,4,5-trifluoro-3-methylbenzoic acid Chemical compound CC1=C(F)C(F)=CC(C(O)=O)=C1F CISXRFRLKWCFJS-UHFFFAOYSA-N 0.000 description 7
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
UBKQNIHKFMGZBC-UHFFFAOYSA-N 3-(dibenzylamino)-6,7-difluoro-1h-quinazoline-2,4-dione Chemical compound O=C1C=2C=C(F)C(F)=CC=2NC(=O)N1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 UBKQNIHKFMGZBC-UHFFFAOYSA-N 0.000 description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 7
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 7
HSOCJGNHMUFGLP-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[3-(methanesulfonamidomethyl)pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(CNS(=O)(=O)C)CCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl HSOCJGNHMUFGLP-UHFFFAOYSA-N 0.000 description 7
125000003342 alkenyl group Chemical group 0.000 description 7
150000001558 benzoic acid derivatives Chemical class 0.000 description 7
238000004587 chromatography analysis Methods 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000011737 fluorine Substances 0.000 description 7
235000019253 formic acid Nutrition 0.000 description 7
238000005984 hydrogenation reaction Methods 0.000 description 7
239000012948 isocyanate Substances 0.000 description 7
150000002513 isocyanates Chemical class 0.000 description 7
150000002576 ketones Chemical group 0.000 description 7
RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 7
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 7
229920006395 saturated elastomer Polymers 0.000 description 7
239000000725 suspension Substances 0.000 description 7
YJUGBLWSKSKQOO-UHFFFAOYSA-N tert-butyl n-amino-n-[3-chloro-2-(cyclopropylamino)-4,5-difluorobenzoyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC(F)=C(F)C(Cl)=C1NC1CC1 YJUGBLWSKSKQOO-UHFFFAOYSA-N 0.000 description 7
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
JZKIUAPWPWPRQJ-UHFFFAOYSA-N 2-(cyclopropylamino)-4,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1NC1CC1 JZKIUAPWPWPRQJ-UHFFFAOYSA-N 0.000 description 6
DPANLOTXSNLKIA-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6,7-difluoro-5-methylquinazoline-2,4-dione Chemical compound O=C1N(N)C(=O)C=2C(C)=C(F)C(F)=CC=2N1C1CC1 DPANLOTXSNLKIA-UHFFFAOYSA-N 0.000 description 6
RWNJQPHKFOIGMK-FJXQXJEOSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylamino)-5,8-difluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=CC(F)=C2C(=O)N(N)C(=O)N(NC3CC3)C2=C1F RWNJQPHKFOIGMK-FJXQXJEOSA-N 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 6
KFTZCNLLRKFMQH-BYPYZUCNSA-N [(3s)-pyrrolidin-3-yl]carbamic acid Chemical compound OC(=O)N[C@H]1CCNC1 KFTZCNLLRKFMQH-BYPYZUCNSA-N 0.000 description 6
230000029936 alkylation Effects 0.000 description 6
238000005804 alkylation reaction Methods 0.000 description 6
238000005576 amination reaction Methods 0.000 description 6
CLCQGUABBALPKC-UHFFFAOYSA-N amino-[2-(cyclopropylamino)-4,5-difluorobenzoyl]carbamic acid Chemical compound OC(=O)N(N)C(=O)C1=CC(F)=C(F)C=C1NC1CC1 CLCQGUABBALPKC-UHFFFAOYSA-N 0.000 description 6
239000003242 anti bacterial agent Substances 0.000 description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 6
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 6
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 6
229910052681 coesite Inorganic materials 0.000 description 6
229910052906 cristobalite Inorganic materials 0.000 description 6
229910052740 iodine Inorganic materials 0.000 description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
239000002480 mineral oil Substances 0.000 description 6
235000010446 mineral oil Nutrition 0.000 description 6
239000000377 silicon dioxide Substances 0.000 description 6
235000012239 silicon dioxide Nutrition 0.000 description 6
239000001632 sodium acetate Substances 0.000 description 6
235000017281 sodium acetate Nutrition 0.000 description 6
MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 6
229910052682 stishovite Inorganic materials 0.000 description 6
239000000126 substance Substances 0.000 description 6
238000006467 substitution reaction Methods 0.000 description 6
DQQJBEAXSOOCPG-UHFFFAOYSA-N tert-butyl n-pyrrolidin-3-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNC1 DQQJBEAXSOOCPG-UHFFFAOYSA-N 0.000 description 6
229910052905 tridymite Inorganic materials 0.000 description 6
ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 6
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 5
FVRSGQOZJYBPQI-UHFFFAOYSA-N 1-(cyclopropylmethyl)-3-(dibenzylamino)-6,7-difluoroquinazoline-2,4-dione Chemical compound O=C1N(N(CC=2C=CC=CC=2)CC=2C=CC=CC=2)C(=O)C=2C=C(F)C(F)=CC=2N1CC1CC1 FVRSGQOZJYBPQI-UHFFFAOYSA-N 0.000 description 5
IFZDYNYZWOBYIG-UHFFFAOYSA-N 2-amino-3-chloro-4,5-difluorobenzoic acid Chemical compound NC1=C(Cl)C(F)=C(F)C=C1C(O)=O IFZDYNYZWOBYIG-UHFFFAOYSA-N 0.000 description 5
MMBZQEWHXIZIMA-UHFFFAOYSA-N 3-(dibenzylamino)-1-ethyl-6,7-difluoroquinazoline-2,4-dione Chemical compound O=C1N(CC)C2=CC(F)=C(F)C=C2C(=O)N1N(CC=1C=CC=CC=1)CC1=CC=CC=C1 MMBZQEWHXIZIMA-UHFFFAOYSA-N 0.000 description 5
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
CEZGKXLXBJRIIA-DHXVBOOMSA-N 3-amino-7-[(3s)-3-[(1r)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H]([C@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CEZGKXLXBJRIIA-DHXVBOOMSA-N 0.000 description 5
XVPKSVLRFAQIBT-FJXQXJEOSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylamino)-6,8-difluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CC3)C2=C1F XVPKSVLRFAQIBT-FJXQXJEOSA-N 0.000 description 5
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 5
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
239000004215 Carbon black (E152) Substances 0.000 description 5
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
MNGRNJKFWXMCOY-VIFPVBQESA-N [5-amino-1-cyclopropyl-6,8-difluoro-7-[(3S)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound NC1=C2C(N(C(N(C2=C(C(=C1F)N1C[C@H](CC1)NC(=O)OC(C)(C)C)F)C1CC1)=O)NC(O)=O)=O MNGRNJKFWXMCOY-VIFPVBQESA-N 0.000 description 5
125000000304 alkynyl group Chemical group 0.000 description 5
150000001559 benzoic acids Chemical class 0.000 description 5
238000005660 chlorination reaction Methods 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
229930195733 hydrocarbon Natural products 0.000 description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
239000013067 intermediate product Substances 0.000 description 5
150000002923 oximes Chemical class 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
238000000926 separation method Methods 0.000 description 5
238000010561 standard procedure Methods 0.000 description 5
238000012360 testing method Methods 0.000 description 5
UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 description 5
IRFSXVIRXMYULF-UHFFFAOYSA-N 1,2-dihydroquinoline Chemical class C1=CC=C2C=CCNC2=C1 IRFSXVIRXMYULF-UHFFFAOYSA-N 0.000 description 4
MGOLQSWUTYNHLQ-UHFFFAOYSA-N 2-(cyclopropylamino)-3-ethoxy-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OCC)=C1NC1CC1 MGOLQSWUTYNHLQ-UHFFFAOYSA-N 0.000 description 4
YQGNOHKZNDOAMS-UHFFFAOYSA-N 2-(cyclopropylamino)-3-fluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound FC1=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OC)=CC(C(O)=O)=C1NC1CC1 YQGNOHKZNDOAMS-UHFFFAOYSA-N 0.000 description 4
YEMGRWLATWFPNC-UHFFFAOYSA-N 2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(C)=C1NC1CC1 YEMGRWLATWFPNC-UHFFFAOYSA-N 0.000 description 4
OKGVLNCIQZERRV-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6,7-difluoroquinazoline-2,4-dione Chemical compound C12=CC(F)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 OKGVLNCIQZERRV-UHFFFAOYSA-N 0.000 description 4
KNZFPXJGVGLPCL-RGMNGODLSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-5,6,8-trifluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=C(F)C(F)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F KNZFPXJGVGLPCL-RGMNGODLSA-N 0.000 description 4
ILVFSJGIZKDLQD-FVGYRXGTSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-8-chloro-1-(2,4-difluoroanilino)-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC=3C(=CC(F)=CC=3)F)C2=C1Cl ILVFSJGIZKDLQD-FVGYRXGTSA-N 0.000 description 4
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
241000894006 Bacteria Species 0.000 description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical group C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 4
125000003545 alkoxy group Chemical group 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
238000007664 blowing Methods 0.000 description 4
235000013877 carbamide Nutrition 0.000 description 4
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
238000006555 catalytic reaction Methods 0.000 description 4
WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 4
MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 4
239000012043 crude product Substances 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
VNGUJPHYEQJGMW-UHFFFAOYSA-N ethyl 2,3-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC=C1N1CC(NC(=O)OC(C)(C)C)CC1 VNGUJPHYEQJGMW-UHFFFAOYSA-N 0.000 description 4
CGIGBVUFCTXFKN-UHFFFAOYSA-N ethyl 2-fluoro-4-pyrrolidin-1-ylbenzoate Chemical compound C1=C(F)C(C(=O)OCC)=CC=C1N1CCCC1 CGIGBVUFCTXFKN-UHFFFAOYSA-N 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
229910000027 potassium carbonate Inorganic materials 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
239000000758 substrate Substances 0.000 description 4
QELMUWDFAGEENM-UHFFFAOYSA-N tert-butyl n-(3-phenylpyrrolidin-3-yl)carbamate Chemical compound C=1C=CC=CC=1C1(NC(=O)OC(C)(C)C)CCNC1 QELMUWDFAGEENM-UHFFFAOYSA-N 0.000 description 4
WIEJVMZWPIUWHO-UHFFFAOYSA-N tert-butyl n-(pyrrolidin-3-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCNC1 WIEJVMZWPIUWHO-UHFFFAOYSA-N 0.000 description 4
DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 4
QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 3
FSKNYSRREPJZKC-UHFFFAOYSA-N (8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxo-7-pyrrolidin-1-ylquinazolin-3-yl)carbamic acid Chemical compound C12=C(Cl)C(N3CCCC3)=C(F)C=C2C(=O)N(NC(=O)O)C(=O)N1C1CC1 FSKNYSRREPJZKC-UHFFFAOYSA-N 0.000 description 3
CUNPECGHILOXJH-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-3-fluoropyrrolidin-3-yl]ethylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(F)(C(C)NC(O)=O)C1 CUNPECGHILOXJH-UHFFFAOYSA-N 0.000 description 3
BJHAQNKKHWKRGP-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C)C(C(C)NC(O)=O)C1 BJHAQNKKHWKRGP-UHFFFAOYSA-N 0.000 description 3
BLSSXGDGAYUNTL-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)piperidin-3-yl]ethylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(C(C)NC(O)=O)C1 BLSSXGDGAYUNTL-UHFFFAOYSA-N 0.000 description 3
BCZJHULRTYMTDK-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 BCZJHULRTYMTDK-UHFFFAOYSA-N 0.000 description 3
YVJHZWWMKFQKDC-UHFFFAOYSA-N 2,4,5-trifluoro-3-methoxybenzoic acid Chemical compound COC1=C(F)C(F)=CC(C(O)=O)=C1F YVJHZWWMKFQKDC-UHFFFAOYSA-N 0.000 description 3
AKAMNXFLKYKFOJ-UHFFFAOYSA-N 2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1F AKAMNXFLKYKFOJ-UHFFFAOYSA-N 0.000 description 3
HTURLAGGUMXTAE-UHFFFAOYSA-N 2-(2,4-difluoroanilino)-4,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C=C1NC1=CC=C(F)C=C1F HTURLAGGUMXTAE-UHFFFAOYSA-N 0.000 description 3
PSGPBQHPUPJTPB-JTQLQIEISA-N 2-(cyclopropylamino)-3,5,6-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C1=C(F)C(F)=C(C(O)=O)C(NC2CC2)=C1F PSGPBQHPUPJTPB-JTQLQIEISA-N 0.000 description 3
SAZGLQMQHCVLMP-NSHDSACASA-N 2-(cyclopropylamino)-3,5-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(O)=O)C(NC2CC2)=C1F SAZGLQMQHCVLMP-NSHDSACASA-N 0.000 description 3
OBSAOCZSTUUSNS-NSHDSACASA-N 2-(cyclopropylamino)-3,6-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C1=CC(F)=C(C(O)=O)C(NC2CC2)=C1F OBSAOCZSTUUSNS-NSHDSACASA-N 0.000 description 3
NGRSPGRZJQJUBI-UHFFFAOYSA-N 2-(cyclopropylamino)-3-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=CC=C(C(O)=O)C(NC2CC2)=C1F NGRSPGRZJQJUBI-UHFFFAOYSA-N 0.000 description 3
ZVPMXYZZVPPXPJ-UHFFFAOYSA-N 2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(F)=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C(C)=C1NC1CC1 ZVPMXYZZVPPXPJ-UHFFFAOYSA-N 0.000 description 3
VTNRGKNKYVRRLB-UHFFFAOYSA-N 2-(cyclopropylamino)-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-3-(phenylmethoxyiminomethyl)benzoic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(O)=O)C(NC2CC2)=C1C=NOCC1=CC=CC=C1 VTNRGKNKYVRRLB-UHFFFAOYSA-N 0.000 description 3
DNAQNIOMQYBGBZ-UHFFFAOYSA-N 2-(cyclopropylamino)-5-fluoro-4-pyrrolidin-1-ylbenzoic acid Chemical compound OC(=O)C1=CC(F)=C(N2CCCC2)C=C1NC1CC1 DNAQNIOMQYBGBZ-UHFFFAOYSA-N 0.000 description 3
DGOZIZVTANAGCA-UHFFFAOYSA-N 2-amino-4,5-difluorobenzoic acid Chemical compound NC1=CC(F)=C(F)C=C1C(O)=O DGOZIZVTANAGCA-UHFFFAOYSA-N 0.000 description 3
GFXOJLCHSLSWDG-UHFFFAOYSA-N 2-amino-n',n'-dibenzyl-4,5-difluorobenzohydrazide Chemical compound NC1=CC(F)=C(F)C=C1C(=O)NN(CC=1C=CC=CC=1)CC1=CC=CC=C1 GFXOJLCHSLSWDG-UHFFFAOYSA-N 0.000 description 3
DUKAXINRLMKHHN-UHFFFAOYSA-N 2-bromo-3-chloro-4,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(Cl)=C1Br DUKAXINRLMKHHN-UHFFFAOYSA-N 0.000 description 3
FLYGUSNYKRVMER-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methyl-7-pyrrolidin-1-ylquinazoline-2,4-dione Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC1 FLYGUSNYKRVMER-UHFFFAOYSA-N 0.000 description 3
FASNKGJGQXLOPA-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C2C(N)C2CN1C(C=1Cl)=C(F)C=C(C(N(N)C2=O)=O)C=1N2C1CC1 FASNKGJGQXLOPA-UHFFFAOYSA-N 0.000 description 3
KBESHLYCSZINAJ-UHFFFAOYSA-N 3-chloro-2,4,5-trifluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(Cl)=C1F KBESHLYCSZINAJ-UHFFFAOYSA-N 0.000 description 3
QGXISKGPLMKYJK-NSHDSACASA-N 3-chloro-2-(cyclopropylamino)-5-fluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(O)=O)C(NC2CC2)=C1Cl QGXISKGPLMKYJK-NSHDSACASA-N 0.000 description 3
PMHWMWJIEAQCPA-UHFFFAOYSA-N 5-amino-8,9-difluoro-3-methyl-2,3-dihydro-1-oxa-3a,5-diazaphenalene-4,6-dione Chemical compound O1CC(C)N2C(=O)N(N)C(=O)C3=C2C1=C(F)C(F)=C3 PMHWMWJIEAQCPA-UHFFFAOYSA-N 0.000 description 3
ZXBHTJQIWXYDMI-UHFFFAOYSA-N 5-chloro-2-(cyclopropylamino)-3-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=C(Cl)C=C(C(O)=O)C(NC2CC2)=C1F ZXBHTJQIWXYDMI-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 3
RNGACVSMDJBBJQ-UHFFFAOYSA-N C1CC1N2C3=C(C(=C(C=C3C(=O)N(C2=O)NC(=O)O)F)N4CCC(=NO)C4)Cl Chemical compound C1CC1N2C3=C(C(=C(C=C3C(=O)N(C2=O)NC(=O)O)F)N4CCC(=NO)C4)Cl RNGACVSMDJBBJQ-UHFFFAOYSA-N 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
PSJZUNCLHZZCJR-UHFFFAOYSA-N NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)(C)CNC(=O)O)C)C1CC1)=O Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)(C)CNC(=O)O)C)C1CC1)=O PSJZUNCLHZZCJR-UHFFFAOYSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
OBSZOKMCBCLMDG-NXEZZACHSA-N [(3R,4S)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]methylcarbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H]([C@@H](C1)C)CNC(O)=O)OC)C1CC1)=O OBSZOKMCBCLMDG-NXEZZACHSA-N 0.000 description 3
XMMMJASZRGZJJF-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-5-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]carbamic acid Chemical compound O=C1N(N)C(=O)C=2C(C)=C(F)C(N3CC(CC3)NC(O)=O)=CC=2N1C1CC1 XMMMJASZRGZJJF-UHFFFAOYSA-N 0.000 description 3
IWPMMJLQCMINFR-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-fluoropyrrolidin-3-yl]carbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(F)C(NC(O)=O)C1 IWPMMJLQCMINFR-UHFFFAOYSA-N 0.000 description 3
DOWPNMKSWSIMNE-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3-(methoxymethyl)pyrrolidin-3-yl]methylcarbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)(COC)CNC(O)=O)C)C1CC1)=O DOWPNMKSWSIMNE-UHFFFAOYSA-N 0.000 description 3
UNKUCRDKKWRWKF-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3-phenylpyrrolidin-3-yl]carbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(NC(O)=O)C1=CC=CC=C1 UNKUCRDKKWRWKF-UHFFFAOYSA-N 0.000 description 3
OQCKJZFQRBFDDJ-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3-phenylpyrrolidin-3-yl]methylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(CNC(O)=O)C1=CC=CC=C1 OQCKJZFQRBFDDJ-UHFFFAOYSA-N 0.000 description 3
DWJOFEVMCNIKSI-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)piperidin-3-yl]methylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC(CNC(O)=O)C1 DWJOFEVMCNIKSI-UHFFFAOYSA-N 0.000 description 3
PSYPRWFTPQUGIA-UHFFFAOYSA-N [1-cyclopropyl-6-fluoro-8-methyl-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound FC1=CC(C(N(NC(O)=O)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(NC(=O)OC(C)(C)C)C1 PSYPRWFTPQUGIA-UHFFFAOYSA-N 0.000 description 3
WMISSEJIBBKIEJ-UHFFFAOYSA-N [1-cyclopropyl-8-ethoxy-6-fluoro-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound FC1=CC(C(N(NC(O)=O)C(=O)N2C3CC3)=O)=C2C(OCC)=C1N1CCC(NC(=O)OC(C)(C)C)C1 WMISSEJIBBKIEJ-UHFFFAOYSA-N 0.000 description 3
OAWNEMSAQWYPEB-UHFFFAOYSA-N [1-cyclopropyl-8-fluoro-6-methoxy-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound COC1=CC(C(N(NC(O)=O)C(=O)N2C3CC3)=O)=C2C(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 OAWNEMSAQWYPEB-UHFFFAOYSA-N 0.000 description 3
KXKHJJHEMIXONA-UHFFFAOYSA-N [1-cyclopropyl-8-fluoro-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=CC=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1F KXKHJJHEMIXONA-UHFFFAOYSA-N 0.000 description 3
RNIDUGDWDSHGDS-UHFFFAOYSA-N [5-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-5-azaspiro[2.4]heptan-7-yl]methylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(CNC(O)=O)C21CC2 RNIDUGDWDSHGDS-UHFFFAOYSA-N 0.000 description 3
NWOKEOSLAZBCJM-UHFFFAOYSA-N [5-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-5-azaspiro[2.4]heptan-7-yl]methylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(CNC(O)=O)C21CC2 NWOKEOSLAZBCJM-UHFFFAOYSA-N 0.000 description 3
LOYYLQDELODEGH-UHFFFAOYSA-N [8-chloro-1-(cyclobutylamino)-6-fluoro-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(NC3CCC3)C2=C1Cl LOYYLQDELODEGH-UHFFFAOYSA-N 0.000 description 3
UYWAGBCHQZZLJW-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[3-(hydroxymethyl)pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(CO)CCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl UYWAGBCHQZZLJW-UHFFFAOYSA-N 0.000 description 3
KGXPHTZSGNZJFG-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(NC(=O)OC(C)(C)C)(C=2C=CC=CC=2)CCN1C(C=1Cl)=C(F)C=C(C(N(NC(O)=O)C2=O)=O)C=1N2C1CC1 KGXPHTZSGNZJFG-UHFFFAOYSA-N 0.000 description 3
DQISBTARDZEMLW-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-azabicyclo[3.1.0]hexan-3-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C2C(NC(=O)OC(C)(C)C)C2CN1C(C=1Cl)=C(F)C=C(C(N(NC(O)=O)C2=O)=O)C=1N2C1CC1 DQISBTARDZEMLW-UHFFFAOYSA-N 0.000 description 3
BSBXSXKLPBKLEO-UHFFFAOYSA-N [8-cyano-1-cyclopropyl-6-fluoro-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1C#N BSBXSXKLPBKLEO-UHFFFAOYSA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
HRDCWPUIXQGAAM-UHFFFAOYSA-N amino(benzoyl)carbamic acid Chemical compound OC(=O)N(N)C(=O)C1=CC=CC=C1 HRDCWPUIXQGAAM-UHFFFAOYSA-N 0.000 description 3
CKYZTGMIVXEZCY-UHFFFAOYSA-N amino-[2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]carbamic acid Chemical compound OC(=O)N(N)C(=O)C1=CC(F)=C(F)C=C1NC1=CC=C(F)C=C1F CKYZTGMIVXEZCY-UHFFFAOYSA-N 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
RNFNDJAIBTYOQL-UHFFFAOYSA-N chloral hydrate Chemical compound OC(O)C(Cl)(Cl)Cl RNFNDJAIBTYOQL-UHFFFAOYSA-N 0.000 description 3
229960002327 chloral hydrate Drugs 0.000 description 3
239000010949 copper Substances 0.000 description 3
230000008878 coupling Effects 0.000 description 3
238000010168 coupling process Methods 0.000 description 3
238000005859 coupling reaction Methods 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
150000004292 cyclic ethers Chemical class 0.000 description 3
125000004663 dialkyl amino group Chemical group 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
JAPFJWKJDHOMGJ-UHFFFAOYSA-N ethyl 2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound C1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 JAPFJWKJDHOMGJ-UHFFFAOYSA-N 0.000 description 3
PLDDUAULBKUJAS-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(CNC(=O)OC(C)(C)C)C1 PLDDUAULBKUJAS-UHFFFAOYSA-N 0.000 description 3
XITYZNUXHDHZKA-JTQLQIEISA-N ethyl 3-chloro-2,5-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(F)C(C(=O)OCC)=CC(F)=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 XITYZNUXHDHZKA-JTQLQIEISA-N 0.000 description 3
125000000524 functional group Chemical group 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
150000004678 hydrides Chemical class 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000012280 lithium aluminium hydride Substances 0.000 description 3
229960002510 mandelic acid Drugs 0.000 description 3
IHUQJPKASFTOBM-UHFFFAOYSA-N n-(2,4-dinitrophenyl)hydroxylamine Chemical compound ONC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O IHUQJPKASFTOBM-UHFFFAOYSA-N 0.000 description 3
ZNBZUZLRLFZYET-UHFFFAOYSA-N n-[1-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)ethylidene]hydroxylamine Chemical compound C1C2(CC2)C(C(=NO)C)CN1CC1=CC=CC=C1 ZNBZUZLRLFZYET-UHFFFAOYSA-N 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
125000004433 nitrogen atom Chemical group N* 0.000 description 3
230000000269 nucleophilic effect Effects 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
150000002924 oxiranes Chemical class 0.000 description 3
239000011591 potassium Substances 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
KFTZCNLLRKFMQH-UHFFFAOYSA-N pyrrolidin-3-ylcarbamic acid Chemical compound OC(=O)NC1CCNC1 KFTZCNLLRKFMQH-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
239000012047 saturated solution Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 3
150000003462 sulfoxides Chemical class 0.000 description 3
239000011593 sulfur Substances 0.000 description 3
IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 3
KHPQHXGYYXYTDN-UHFFFAOYSA-N tert-butyl n-(piperidin-3-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CCCNC1 KHPQHXGYYXYTDN-UHFFFAOYSA-N 0.000 description 3
OOHUYMFBULRIKW-UHFFFAOYSA-N tert-butyl n-[[3-chloro-2-(cyclopropylamino)-5-fluoro-4-pyrrolidin-1-ylbenzoyl]amino]carbamate Chemical compound ClC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CCCC1 OOHUYMFBULRIKW-UHFFFAOYSA-N 0.000 description 3
ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
150000003672 ureas Chemical group 0.000 description 3
BZMMRNKDONDVIB-UHFFFAOYSA-N (1-ethoxycyclopropyl)oxy-trimethylsilane Chemical compound CCOC1(O[Si](C)(C)C)CC1 BZMMRNKDONDVIB-UHFFFAOYSA-N 0.000 description 2
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
RIHSDGDGZCNTAD-UHFFFAOYSA-N 1-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)ethanone Chemical compound C1C2(CC2)C(C(=O)C)CN1CC1=CC=CC=C1 RIHSDGDGZCNTAD-UHFFFAOYSA-N 0.000 description 2
UAVGQMYLETUIIP-UHFFFAOYSA-N 1-(7,8-difluoro-3-methyl-2,3-dihydro-1,4-benzoxazin-4-yl)-2-hydroxyiminoethanone Chemical compound FC1=CC=C2N(C(=O)C=NO)C(C)COC2=C1F UAVGQMYLETUIIP-UHFFFAOYSA-N 0.000 description 2
BXTNFYDALPLOTQ-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3-methoxypyrrolidin-3-yl]ethylcarbamic acid Chemical compound C1C(OC)(C(C)NC(O)=O)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C BXTNFYDALPLOTQ-UHFFFAOYSA-N 0.000 description 2
QLTMOMYFGJLVAC-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-4-methylpyrrolidin-3-yl]ethylcarbamic acid Chemical compound C1C(C)C(C(NC(O)=O)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QLTMOMYFGJLVAC-UHFFFAOYSA-N 0.000 description 2
ZIKPWAIZPGTPHD-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)piperidin-3-yl]ethylcarbamic acid Chemical compound C1C(C(NC(O)=O)C)CCCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C ZIKPWAIZPGTPHD-UHFFFAOYSA-N 0.000 description 2
BBAXQOJRIACXAE-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-5-methylquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C(C)=C(F)C(F)=CC=2N1C1CC1 BBAXQOJRIACXAE-UHFFFAOYSA-N 0.000 description 2
VHLOUICJKIEZJE-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoro-8-methylquinazoline-2,4-dione Chemical compound CC1=C(F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 VHLOUICJKIEZJE-UHFFFAOYSA-N 0.000 description 2
JPIQZZJSEQBUNF-UHFFFAOYSA-N 1-cyclopropyl-6,7-difluoroquinazoline-2,4-dione Chemical compound O=C1NC(=O)C=2C=C(F)C(F)=CC=2N1C1CC1 JPIQZZJSEQBUNF-UHFFFAOYSA-N 0.000 description 2
UUWIIEPTTXHXHP-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-hydroxysulfonothioylpyrido[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C=2C=C(F)C(S(=O)(=S)O)=NC=2N1C1CC1 UUWIIEPTTXHXHP-UHFFFAOYSA-N 0.000 description 2
XIOXYTMCWHFHDQ-UHFFFAOYSA-N 1-cyclopropyl-6-fluoro-7-methylsulfanylpyrido[2,3-d]pyrimidine-2,4-dione Chemical compound O=C1NC(=O)C=2C=C(F)C(SC)=NC=2N1C1CC1 XIOXYTMCWHFHDQ-UHFFFAOYSA-N 0.000 description 2
VKCJKOCVSQPRJF-UHFFFAOYSA-N 1-cyclopropyl-8-ethyl-6,7-difluoroquinazoline-2,4-dione Chemical compound CCC1=C(F)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 VKCJKOCVSQPRJF-UHFFFAOYSA-N 0.000 description 2
XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 2
DBJFCKAZPYOLBP-UHFFFAOYSA-N 2,4,5-trifluoro-3-(phenylmethoxyiminomethyl)benzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(C=NOCC=2C=CC=CC=2)=C1F DBJFCKAZPYOLBP-UHFFFAOYSA-N 0.000 description 2
RNXYODOPINJXQD-UHFFFAOYSA-N 2,6-dichloro-n-(cyclopropylcarbamoyl)-5-fluoropyridine-3-carboxamide Chemical compound N1=C(Cl)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1Cl RNXYODOPINJXQD-UHFFFAOYSA-N 0.000 description 2
SJQOYQFMCLGIMN-UHFFFAOYSA-N 2-(butan-2-ylamino)-3-chloro-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1=C(C(O)=O)C(NC(C)CC)=C(Cl)C(N2CC(CC2)NC(=O)OC(C)(C)C)=C1F SJQOYQFMCLGIMN-UHFFFAOYSA-N 0.000 description 2
GLGNFKKDDWVGCO-UHFFFAOYSA-N 2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(F)=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C(OC)=C1NC1CC1 GLGNFKKDDWVGCO-UHFFFAOYSA-N 0.000 description 2
VTFCXMNTJYSFIR-UHFFFAOYSA-N 2-amino-5-chloro-4-fluorobenzoic acid Chemical compound NC1=CC(F)=C(Cl)C=C1C(O)=O VTFCXMNTJYSFIR-UHFFFAOYSA-N 0.000 description 2
IYRJODMZHWPACV-UHFFFAOYSA-N 2-pyrrolidin-3-ylpropan-2-ol Chemical compound CC(C)(O)C1CCNC1 IYRJODMZHWPACV-UHFFFAOYSA-N 0.000 description 2
PUNCYPYHZDAAFT-UHFFFAOYSA-N 3,4,6-trifluoro-2-methylbenzamide Chemical compound CC1=C(F)C(F)=CC(F)=C1C(N)=O PUNCYPYHZDAAFT-UHFFFAOYSA-N 0.000 description 2
DRSBAYGWJDVTJT-DHTOPLTISA-N 3-amino-1-cyclopropyl-6-fluoro-7-[(3r)-3-[(1r)-1-(methylamino)ethyl]pyrrolidin-1-yl]pyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](C)NC)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 DRSBAYGWJDVTJT-DHTOPLTISA-N 0.000 description 2
IYMWYSOXLZRBDG-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-hydroxysulfonothioylpyrido[2,3-d]pyrimidine-2,4-dione Chemical compound C12=NC(S(O)(=O)=S)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 IYMWYSOXLZRBDG-UHFFFAOYSA-N 0.000 description 2
FMSRPZVXQVAYBC-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methoxy-7-pyrrolidin-1-ylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC1 FMSRPZVXQVAYBC-UHFFFAOYSA-N 0.000 description 2
RSTPIMNUVMQFMQ-QWHCGFSZSA-N 3-amino-1-cyclopropyl-7-[(3r)-3-[(1s)-1-(ethylamino)ethyl]pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione Chemical compound C1[C@H]([C@H](C)NCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C RSTPIMNUVMQFMQ-QWHCGFSZSA-N 0.000 description 2
DZJNJNPCNQIIQB-JHEYCYPBSA-N 3-amino-1-cyclopropyl-7-[(3r)-3-[(1s)-1-(ethylamino)ethyl]pyrrolidin-1-yl]-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@H](C)NCC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C DZJNJNPCNQIIQB-JHEYCYPBSA-N 0.000 description 2
KZIFDDHQIZBWDZ-UHFFFAOYSA-N 3-amino-1-cyclopropyl-8-ethyl-6,7-difluoroquinazoline-2,4-dione Chemical compound CCC1=C(F)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 KZIFDDHQIZBWDZ-UHFFFAOYSA-N 0.000 description 2
FBZYWRAYHYNGIY-UHFFFAOYSA-N 3-amino-7-(2-amino-5-azaspiro[2.4]heptan-5-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CCC21CC2N FBZYWRAYHYNGIY-UHFFFAOYSA-N 0.000 description 2
YVKARDDEPDIMAW-UHFFFAOYSA-N 3-amino-7-(3-amino-3-methylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(N)C1 YVKARDDEPDIMAW-UHFFFAOYSA-N 0.000 description 2
FCCBYADJONTRAR-UHFFFAOYSA-N 3-amino-7-(3-amino-4-fluoropyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(N)C(F)C1 FCCBYADJONTRAR-UHFFFAOYSA-N 0.000 description 2
PYMLOGUHBHDDDD-UHFFFAOYSA-N 3-amino-7-(3-amino-4-methoxypyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(N)C(OC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1OC PYMLOGUHBHDDDD-UHFFFAOYSA-N 0.000 description 2
DULAPBRRLOTGEA-UHFFFAOYSA-N 3-amino-7-(3-amino-4-methoxypyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(N)C(OC)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C DULAPBRRLOTGEA-UHFFFAOYSA-N 0.000 description 2
NOMNLRFWBUGKMX-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.O=C1N(N)C(=O)C=2C(C)=C(F)C(N3CC(N)CC3)=CC=2N1C1CC1 NOMNLRFWBUGKMX-UHFFFAOYSA-N 0.000 description 2
AZBUXTXNGNAFDX-UHFFFAOYSA-N 3-amino-7-(6-amino-3-azabicyclo[3.1.0]hexan-3-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(N2CC3C(N)C3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 AZBUXTXNGNAFDX-UHFFFAOYSA-N 0.000 description 2
FPGPDSXCAGDSCS-UHFFFAOYSA-N 3-amino-7-(7-amino-5-methyl-3-azabicyclo[3.2.0]heptan-3-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione Chemical compound COC1=C(N2CC3(C)CC(N)C3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 FPGPDSXCAGDSCS-UHFFFAOYSA-N 0.000 description 2
WARILAOSVCTZHW-UXQCFNEQSA-N 3-amino-7-[(3s)-3-[(1r)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@H]([C@@H](C)N)C1 WARILAOSVCTZHW-UXQCFNEQSA-N 0.000 description 2
NDEZBXLQDYBISD-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.COC1=C(N2CC3(CN)CC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 NDEZBXLQDYBISD-UHFFFAOYSA-N 0.000 description 2
FOPKVPJYMUNVHX-UHFFFAOYSA-N 3-amino-7-[1-(aminomethyl)-3-azabicyclo[3.1.0]hexan-3-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(N2CC3(CN)CC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 FOPKVPJYMUNVHX-UHFFFAOYSA-N 0.000 description 2
OGIXTCAUYCPEIX-UHFFFAOYSA-N 3-amino-7-[3-(2-aminoethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC(CCN)C1 OGIXTCAUYCPEIX-UHFFFAOYSA-N 0.000 description 2
CRVHZOLJNZATFA-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-hydroxypyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(O)(CN)C1 CRVHZOLJNZATFA-UHFFFAOYSA-N 0.000 description 2
IPMRREAGKOOZGU-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-phenylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(CN)C1=CC=CC=C1 IPMRREAGKOOZGU-UHFFFAOYSA-N 0.000 description 2
IFVYCDRWSZNRBZ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)azetidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C1 IFVYCDRWSZNRBZ-UHFFFAOYSA-N 0.000 description 2
FDBCOOAUGVAZKJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(CN)C1 FDBCOOAUGVAZKJ-UHFFFAOYSA-N 0.000 description 2
JQKQPGZGGHLAGC-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC(CN)C1 JQKQPGZGGHLAGC-UHFFFAOYSA-N 0.000 description 2
ICWQWMNAYJVMHJ-UHFFFAOYSA-N 3-amino-7-[4-(aminomethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)CC1 ICWQWMNAYJVMHJ-UHFFFAOYSA-N 0.000 description 2
YWAVONXVCJBKCA-UHFFFAOYSA-N 3-amino-7-[7-(1-aminoethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC(N)C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)C)CC11CC1 YWAVONXVCJBKCA-UHFFFAOYSA-N 0.000 description 2
OCPWJXAGUWLAGV-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CC(CN)C21CC2 OCPWJXAGUWLAGV-UHFFFAOYSA-N 0.000 description 2
DZLQAGNSWSNNNR-UHFFFAOYSA-N 3-azabicyclo[3.1.0]hexan-6-ylcarbamic acid Chemical compound C1NCC2C(NC(=O)O)C21 DZLQAGNSWSNNNR-UHFFFAOYSA-N 0.000 description 2
NBSLFEKLBGUUEA-UHFFFAOYSA-N 3-ethyl-2,4,5-trifluorobenzamide Chemical compound CCC1=C(F)C(F)=CC(C(N)=O)=C1F NBSLFEKLBGUUEA-UHFFFAOYSA-N 0.000 description 2
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 2
ZQQSRVPOAHYHEL-UHFFFAOYSA-N 4-bromo-2-fluorobenzoic acid Chemical class OC(=O)C1=CC=C(Br)C=C1F ZQQSRVPOAHYHEL-UHFFFAOYSA-N 0.000 description 2
TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical class OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 2
QMUXRCCIZUUWQR-UHFFFAOYSA-N 5-amino-8,9-difluoro-5-methyl-6,7-dihydro-5h-pyrido[3,2,1-ij]quinazoline-1,3-dione Chemical compound C1CC(C)(N)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3 QMUXRCCIZUUWQR-UHFFFAOYSA-N 0.000 description 2
LHTZMHLHUPXGHH-UHFFFAOYSA-N 5-chloro-2-(cyclopropylamino)-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC(Cl)=C(F)C=C1NC1CC1 LHTZMHLHUPXGHH-UHFFFAOYSA-N 0.000 description 2
FJANZXDFICNMCN-UHFFFAOYSA-N 6,7-difluoro-3-methyl-3,4-dihydro-5-oxa-2a-aza-acenaphthylene-1,2-dione Chemical compound O=C1C(=O)N2C(C)COC3=C2C1=CC(F)=C3F FJANZXDFICNMCN-UHFFFAOYSA-N 0.000 description 2
ZJQMCCCNQBUWKU-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine-5-carboxylic acid Chemical compound FC1=CC(C(O)=O)=C2NC(C)COC2=C1F ZJQMCCCNQBUWKU-UHFFFAOYSA-N 0.000 description 2
NQNNGQFUHXZUQQ-UHFFFAOYSA-N 7-(1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridin-6-yl)-3-amino-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(N2CC3NCCCC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 NQNNGQFUHXZUQQ-UHFFFAOYSA-N 0.000 description 2
XYFHOYFAEHDZGW-UHFFFAOYSA-N 7-[7a-(aminomethyl)-3,3a,4,5,6,7-hexahydro-1h-isoindol-2-yl]-3-amino-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.CC1=C(N2CC3(CN)CCCCC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 XYFHOYFAEHDZGW-UHFFFAOYSA-N 0.000 description 2
ZZEOFKLXAXVIOD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione Chemical compound N1=C(Cl)C(F)=CC(C(NC2=O)=O)=C1N2C1CC1 ZZEOFKLXAXVIOD-UHFFFAOYSA-N 0.000 description 2
CGEUYSMLTTYJHA-UHFFFAOYSA-N 8,9-difluoro-3-methyl-2,3-dihydro-1-oxa-3a,5-diaza-phenalene-4,6-dione Chemical compound O1CC(C)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3 CGEUYSMLTTYJHA-UHFFFAOYSA-N 0.000 description 2
VRSAEAQQGFVZFV-UHFFFAOYSA-N 8,9-difluoro-5-methyl-6,7-dihydro-5h-pyrido[3,2,1-ij]quinazoline-1,3-dione Chemical compound C1CC(C)N2C(=O)NC(=O)C3=C2C1=C(F)C(F)=C3 VRSAEAQQGFVZFV-UHFFFAOYSA-N 0.000 description 2
ZHGNHOOVYPHPNJ-UHFFFAOYSA-N Amigdalin Chemical compound FC(F)(F)C(=O)OCC1OC(OCC2OC(OC(C#N)C3=CC=CC=C3)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C2OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C(OC(=O)C(F)(F)F)C1OC(=O)C(F)(F)F ZHGNHOOVYPHPNJ-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
108010041052 DNA Topoisomerase IV Proteins 0.000 description 2
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
239000007818 Grignard reagent Substances 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
239000012359 Methanesulfonyl chloride Substances 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
239000002262 Schiff base Substances 0.000 description 2
150000004753 Schiff bases Chemical class 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
FKCMADOPPWWGNZ-YUMQZZPRSA-N [(2r)-1-[(2s)-2-amino-3-methylbutanoyl]pyrrolidin-2-yl]boronic acid Chemical compound CC(C)[C@H](N)C(=O)N1CCC[C@H]1B(O)O FKCMADOPPWWGNZ-YUMQZZPRSA-N 0.000 description 2
LDQNYHNPPYYEBF-PRHODGIISA-N [(3R,4S)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-fluoropyrrolidin-3-yl]methylcarbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H]([C@@H](C1)F)CNC(O)=O)OC)C1CC1)=O LDQNYHNPPYYEBF-PRHODGIISA-N 0.000 description 2
QITRHDONYHOMEQ-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)piperidin-3-yl]methylcarbamic acid Chemical compound FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(CNC(O)=O)C1 QITRHDONYHOMEQ-UHFFFAOYSA-N 0.000 description 2
OULOUDNKONNREH-UHFFFAOYSA-N [1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3-(fluoromethyl)pyrrolidin-3-yl]methylcarbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(CC1)(CF)CNC(O)=O)C)C1CC1)=O OULOUDNKONNREH-UHFFFAOYSA-N 0.000 description 2
238000010958 [3+2] cycloaddition reaction Methods 0.000 description 2
BZJBKQNZSPKBQK-UHFFFAOYSA-N [6,8-dichloro-1-cyclopropyl-7-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=C(Cl)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl BZJBKQNZSPKBQK-UHFFFAOYSA-N 0.000 description 2
BGRGVVRSJXYHLB-UHFFFAOYSA-N [7-(3-carbamoylpiperidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(C(=O)N)CCCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl BGRGVVRSJXYHLB-UHFFFAOYSA-N 0.000 description 2
JHHZHVYKGCFNMM-FMLNKVPISA-N [7-[(3S,4S)-3-[1-amino-2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]-4-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C(C)(C)(C)OC(=O)C([C@@H]1CN(C[C@H]1C)C1=C(C=C2C(N(C(N(C2=C1Cl)C1CC1)=O)NC(O)=O)=O)F)N JHHZHVYKGCFNMM-FMLNKVPISA-N 0.000 description 2
XKDKVSOGSDWQBN-UHFFFAOYSA-N [7a-(aminomethyl)-3,3a,4,5,6,7-hexahydro-1H-isoindol-2-yl]carbamic acid Chemical compound NCC12CN(CC2CCCC1)NC(O)=O XKDKVSOGSDWQBN-UHFFFAOYSA-N 0.000 description 2
LTIHUXMRGZOUKJ-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound CC(C)(C)OC(=O)NC1CN(C=2C(=C3C(C(N(NC(O)=O)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC11CC1 LTIHUXMRGZOUKJ-UHFFFAOYSA-N 0.000 description 2
AVRXUQALDJVGAX-UHFFFAOYSA-N [[2-(cyclopropylamino)-3-ethoxy-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OCC)=C1NC1CC1 AVRXUQALDJVGAX-UHFFFAOYSA-N 0.000 description 2
IYZBCRMRIRUZTO-UHFFFAOYSA-N [[2-(cyclopropylamino)-3-fluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound FC1=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OC)=CC(C(=O)NNC(O)=O)=C1NC1CC1 IYZBCRMRIRUZTO-UHFFFAOYSA-N 0.000 description 2
NFJYXCOYGPYWMJ-UHFFFAOYSA-N [[2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C(OC)=C1NC1CC1 NFJYXCOYGPYWMJ-UHFFFAOYSA-N 0.000 description 2
XOJFHITZCDSABC-UHFFFAOYSA-N [[2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(C)=C1NC1CC1 XOJFHITZCDSABC-UHFFFAOYSA-N 0.000 description 2
FZXRBBRJITXWLY-UHFFFAOYSA-N [[2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CNC(=O)OC(C)(C)C)CC2)C(C)=C1NC1CC1 FZXRBBRJITXWLY-UHFFFAOYSA-N 0.000 description 2
PEGIKIAHJGTNFW-CQSZACIVSA-N [[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[(7S)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]benzoyl]amino]carbamic acid Chemical compound C([C@H]1NC(=O)OC(C)(C)C)N(C=2C(=C(NC3CC3)C(C(=O)NNC(O)=O)=CC=2F)Cl)CC11CC1 PEGIKIAHJGTNFW-CQSZACIVSA-N 0.000 description 2
RPBWMILJKYAMOO-UHFFFAOYSA-N [[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(=O)NNC(O)=O)C(NC2CC2)=C1Cl RPBWMILJKYAMOO-UHFFFAOYSA-N 0.000 description 2
NEWLMSNHUACYQQ-UHFFFAOYSA-N [[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[3-methyl-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoyl]amino]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)(C)CCN1C1=C(F)C=C(C(=O)NNC(O)=O)C(NC2CC2)=C1Cl NEWLMSNHUACYQQ-UHFFFAOYSA-N 0.000 description 2
FYJKEHKQUPSJDH-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;potassium Chemical compound [K].C[Si](C)(C)N[Si](C)(C)C FYJKEHKQUPSJDH-UHFFFAOYSA-N 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000001299 aldehydes Chemical class 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
150000001356 alkyl thiols Chemical class 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
235000019270 ammonium chloride Nutrition 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
229940088710 antibiotic agent Drugs 0.000 description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
150000003936 benzamides Chemical class 0.000 description 2
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
MXSTYZFUEGSFSI-AWEZNQCLSA-N benzyl 2,3,5,6-tetrafluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1F)F)=C(F)C(F)=C1C(=O)OCC1=CC=CC=C1 MXSTYZFUEGSFSI-AWEZNQCLSA-N 0.000 description 2
YHZJBIHCJSVWKD-KRWDZBQOSA-N benzyl 2-(cyclopropylamino)-3,5,6-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1NC2CC2)F)=C(F)C(F)=C1C(=O)OCC1=CC=CC=C1 YHZJBIHCJSVWKD-KRWDZBQOSA-N 0.000 description 2
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical class OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
239000012267 brine Substances 0.000 description 2
230000031709 bromination Effects 0.000 description 2
238000005893 bromination reaction Methods 0.000 description 2
ODWXUNBKCRECNW-UHFFFAOYSA-M bromocopper(1+) Chemical compound Br[Cu+] ODWXUNBKCRECNW-UHFFFAOYSA-M 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
229910002091 carbon monoxide Inorganic materials 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
238000004296 chiral HPLC Methods 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
229960003405 ciprofloxacin Drugs 0.000 description 2
229910052802 copper Inorganic materials 0.000 description 2
KZZKOVLJUKWSKX-UHFFFAOYSA-N cyclobutanamine Chemical compound NC1CCC1 KZZKOVLJUKWSKX-UHFFFAOYSA-N 0.000 description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
238000010511 deprotection reaction Methods 0.000 description 2
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
SBHMXBYMQZRRLC-UHFFFAOYSA-N ethyl 2,3,4,5-tetrafluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(F)=C1F SBHMXBYMQZRRLC-UHFFFAOYSA-N 0.000 description 2
GJFOWPZJBADLDJ-UHFFFAOYSA-N ethyl 2,3,4,6-tetrafluorobenzoate Chemical compound CCOC(=O)C1=C(F)C=C(F)C(F)=C1F GJFOWPZJBADLDJ-UHFFFAOYSA-N 0.000 description 2
MLANUBGYWOMWLZ-UHFFFAOYSA-N ethyl 2,3,4-trifluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C(F)=C1F MLANUBGYWOMWLZ-UHFFFAOYSA-N 0.000 description 2
PLHHLRVGWNGWPX-JTQLQIEISA-N ethyl 2,3,5-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC(F)=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 PLHHLRVGWNGWPX-JTQLQIEISA-N 0.000 description 2
ZXFYRSUEOKXKOQ-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-methoxybenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(OC)=C1F ZXFYRSUEOKXKOQ-UHFFFAOYSA-N 0.000 description 2
YCDADJUAUJPWHD-UHFFFAOYSA-N ethyl 2,4,5-trifluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C=C1F YCDADJUAUJPWHD-UHFFFAOYSA-N 0.000 description 2
AQTKJIVKYZAFNJ-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 AQTKJIVKYZAFNJ-UHFFFAOYSA-N 0.000 description 2
KJFHMLDTVFQOQA-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound CC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(CNC(=O)OC(C)(C)C)CC1 KJFHMLDTVFQOQA-UHFFFAOYSA-N 0.000 description 2
LRIZYRFXKQSOFG-UHFFFAOYSA-N ethyl 2,5-difluoro-4-pyrrolidin-1-ylbenzoate Chemical compound C1=C(F)C(C(=O)OCC)=CC(F)=C1N1CCCC1 LRIZYRFXKQSOFG-UHFFFAOYSA-N 0.000 description 2
RCKVZZTXQFAAPT-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-3-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC=C1N1CCC(NC(=O)OC(C)(C)C)C1 RCKVZZTXQFAAPT-UHFFFAOYSA-N 0.000 description 2
KLDDQZNIRQUHKU-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-4-pyrrolidin-1-ylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(N2CCCC2)C=C1NC1CC1 KLDDQZNIRQUHKU-UHFFFAOYSA-N 0.000 description 2
MYSSYHAITZSBEY-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-6-methylsulfanylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(F)=C(SC)N=C1NC1CC1 MYSSYHAITZSBEY-UHFFFAOYSA-N 0.000 description 2
UPMFDOIEEUTSQC-UHFFFAOYSA-N ethyl 3-chloro-2,4,5-trifluorobenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(Cl)=C1F UPMFDOIEEUTSQC-UHFFFAOYSA-N 0.000 description 2
FDLKLRZONDKRDD-UHFFFAOYSA-N ethyl 3-chloro-2,5-difluoro-4-[3-(triazol-1-yl)pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(N2N=NC=C2)CC1 FDLKLRZONDKRDD-UHFFFAOYSA-N 0.000 description 2
KDKBIFLYOSNINK-ZDUSSCGKSA-N ethyl 3-chloro-2-(cyclopropylamino)-5-fluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 KDKBIFLYOSNINK-ZDUSSCGKSA-N 0.000 description 2
FEBASYOFRCJJIS-UHFFFAOYSA-N ethyl 5-chloro-2-(cyclopropylamino)-3-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC(Cl)=C1N1CCC(NC(=O)OC(C)(C)C)C1 FEBASYOFRCJJIS-UHFFFAOYSA-N 0.000 description 2
UNTKOCVJKCACCM-UHFFFAOYSA-N ethyl 5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2-(propan-2-ylamino)benzoate Chemical compound C1=C(NC(C)C)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 UNTKOCVJKCACCM-UHFFFAOYSA-N 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
238000001640 fractional crystallisation Methods 0.000 description 2
239000012458 free base Substances 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
WQYVRQLZKVEZGA-UHFFFAOYSA-N hypochlorite Chemical compound Cl[O-] WQYVRQLZKVEZGA-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
238000000338 in vitro Methods 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
JJXINDNYLSMEBI-UHFFFAOYSA-N isocyanato thiohypochlorite Chemical compound ClSN=C=O JJXINDNYLSMEBI-UHFFFAOYSA-N 0.000 description 2
239000010410 layer Substances 0.000 description 2
OVEHNNQXLPJPPL-UHFFFAOYSA-N lithium;n-propan-2-ylpropan-2-amine Chemical compound [Li].CC(C)NC(C)C OVEHNNQXLPJPPL-UHFFFAOYSA-N 0.000 description 2
150000002739 metals Chemical class 0.000 description 2
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
UHTYEKZZCFLKOJ-UHFFFAOYSA-N methyl 5,6-difluoro-2-methyl-1,2,3,4-tetrahydroquinoline-8-carboxylate Chemical compound C1CC(C)NC2=C1C(F)=C(F)C=C2C(=O)OC UHTYEKZZCFLKOJ-UHFFFAOYSA-N 0.000 description 2
FLKMOQAAIRZPTP-UHFFFAOYSA-N methyl 5,6-difluoro-2-methylquinoline-8-carboxylate Chemical compound C1=C(C)N=C2C(C(=O)OC)=CC(F)=C(F)C2=C1 FLKMOQAAIRZPTP-UHFFFAOYSA-N 0.000 description 2
VHFALIIFFRARFE-UHFFFAOYSA-N methyl 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine-5-carboxylate Chemical compound O1CC(C)NC2=C1C(F)=C(F)C=C2C(=O)OC VHFALIIFFRARFE-UHFFFAOYSA-N 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
239000002808 molecular sieve Substances 0.000 description 2
125000002757 morpholinyl group Chemical group 0.000 description 2
JVDVBWCTHUYCRJ-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-2,4,5-trifluoro-3-methoxybenzamide Chemical compound COC1=C(F)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1F JVDVBWCTHUYCRJ-UHFFFAOYSA-N 0.000 description 2
BYEGWNSSZUNVFM-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-2,4,5-trifluoro-3-methylbenzamide Chemical compound CC1=C(F)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1F BYEGWNSSZUNVFM-UHFFFAOYSA-N 0.000 description 2
ZIMCPIQGGYZXRS-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-3,4,6-trifluoro-2-methylbenzamide Chemical compound CC1=C(F)C(F)=CC(F)=C1C(=O)NC(=O)NC1CC1 ZIMCPIQGGYZXRS-UHFFFAOYSA-N 0.000 description 2
QWAPDZOXNZQTRF-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)-3-ethyl-2,4,5-trifluorobenzamide Chemical compound CCC1=C(F)C(F)=CC(C(=O)NC(=O)NC2CC2)=C1F QWAPDZOXNZQTRF-UHFFFAOYSA-N 0.000 description 2
QDLKRVMKDILCHC-UHFFFAOYSA-N n-(cyclopropylcarbamoyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(=O)NC1CC1 QDLKRVMKDILCHC-UHFFFAOYSA-N 0.000 description 2
VJPYEYRKXXVWNA-UHFFFAOYSA-N n-(pyrrolidin-3-ylmethyl)propan-2-amine Chemical compound CC(C)NCC1CCNC1 VJPYEYRKXXVWNA-UHFFFAOYSA-N 0.000 description 2
HGAWACRPWVRCFI-UHFFFAOYSA-N n-pyrrolidin-3-ylidenehydroxylamine Chemical compound ON=C1CCNC1 HGAWACRPWVRCFI-UHFFFAOYSA-N 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
YZERDTREOUSUHF-UHFFFAOYSA-N pentafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C(F)=C(F)C(F)=C1F YZERDTREOUSUHF-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229910052700 potassium Inorganic materials 0.000 description 2
235000011056 potassium acetate Nutrition 0.000 description 2
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000006268 reductive amination reaction Methods 0.000 description 2
238000011160 research Methods 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
239000011975 tartaric acid Substances 0.000 description 2
235000002906 tartaric acid Nutrition 0.000 description 2
LRTPRHCNWAEZBN-UWVGGRQHSA-N tert-butyl (3as,7ar)-1,2,3,3a,4,6,7,7a-octahydropyrrolo[3,4-c]pyridine-5-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@H]2CNC[C@H]21 LRTPRHCNWAEZBN-UWVGGRQHSA-N 0.000 description 2
FNMZLLREXJAYRY-UHFFFAOYSA-N tert-butyl n-(2,4-dioxo-1h-quinazolin-3-yl)carbamate Chemical compound C1=CC=C2C(=O)N(NC(=O)OC(C)(C)C)C(=O)NC2=C1 FNMZLLREXJAYRY-UHFFFAOYSA-N 0.000 description 2
UIYMGRQQGQOESZ-UHFFFAOYSA-N tert-butyl n-(3-azabicyclo[3.1.0]hexan-1-ylmethyl)carbamate Chemical compound C1NCC2(CNC(=O)OC(C)(C)C)C1C2 UIYMGRQQGQOESZ-UHFFFAOYSA-N 0.000 description 2
DQQJBEAXSOOCPG-ZETCQYMHSA-N tert-butyl n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H]1CCNC1 DQQJBEAXSOOCPG-ZETCQYMHSA-N 0.000 description 2
MLSQGNHGJMPPNM-UHFFFAOYSA-N tert-butyl n-[1-(4,4-dimethylpyrrolidin-3-yl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1CNCC1(C)C MLSQGNHGJMPPNM-UHFFFAOYSA-N 0.000 description 2
UAWBFPVQUJUVQG-UHFFFAOYSA-N tert-butyl n-[1-(4-methylpyrrolidin-3-yl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1CNCC1C UAWBFPVQUJUVQG-UHFFFAOYSA-N 0.000 description 2
UKXZEKOMLQUGDZ-UHFFFAOYSA-N tert-butyl n-[1-[2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]-5-(propan-2-ylamino)phenyl]pyrrolidin-3-yl]carbamate Chemical compound C1=C(C(=O)NNC(=O)OC(C)(C)C)C(NC(C)C)=CC(N2CC(CC2)NC(=O)OC(C)(C)C)=C1F UKXZEKOMLQUGDZ-UHFFFAOYSA-N 0.000 description 2
CEFJWUXTHLISAP-BDAKNGLRSA-N tert-butyl n-[[(3s,4s)-4-methylpyrrolidin-3-yl]methyl]carbamate Chemical compound C[C@@H]1CNC[C@H]1CNC(=O)OC(C)(C)C CEFJWUXTHLISAP-BDAKNGLRSA-N 0.000 description 2
AUHKMEIWCSKWTB-UHFFFAOYSA-N tert-butyl n-[[1-[5-(cyclopropylamino)-2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=CC(NC2CC2)=C(C(=O)NNC(=O)OC(C)(C)C)C=C1F AUHKMEIWCSKWTB-UHFFFAOYSA-N 0.000 description 2
JJOOCVNFHZXGPL-UHFFFAOYSA-N tert-butyl n-amino-n-benzoylcarbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC=CC=C1 JJOOCVNFHZXGPL-UHFFFAOYSA-N 0.000 description 2
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical group 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
ONDSBJMLAHVLMI-UHFFFAOYSA-N trimethylsilyldiazomethane Chemical compound C[Si](C)(C)[CH-][N+]#N ONDSBJMLAHVLMI-UHFFFAOYSA-N 0.000 description 2
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
ASGMFNBUXDJWJJ-JLCFBVMHSA-N (1R,3R)-3-[[3-bromo-1-[4-(5-methyl-1,3,4-thiadiazol-2-yl)phenyl]pyrazolo[3,4-d]pyrimidin-6-yl]amino]-N,1-dimethylcyclopentane-1-carboxamide Chemical compound BrC1=NN(C2=NC(=NC=C21)N[C@H]1C[C@@](CC1)(C(=O)NC)C)C1=CC=C(C=C1)C=1SC(=NN=1)C ASGMFNBUXDJWJJ-JLCFBVMHSA-N 0.000 description 1
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 description 1
GBVBYEVLALCXBL-RNFRBKRXSA-N (1r)-n-methyl-1-[(3r)-pyrrolidin-3-yl]ethanamine Chemical compound CN[C@H](C)[C@@H]1CCNC1 GBVBYEVLALCXBL-RNFRBKRXSA-N 0.000 description 1
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
KPIYLFUXCFFIFT-NTSWFWBYSA-N (1s)-1-[(3r)-pyrrolidin-3-yl]ethanamine Chemical compound C[C@H](N)[C@@H]1CCNC1 KPIYLFUXCFFIFT-NTSWFWBYSA-N 0.000 description 1
GBVBYEVLALCXBL-NKWVEPMBSA-N (1s)-n-methyl-1-[(3r)-pyrrolidin-3-yl]ethanamine Chemical compound CN[C@@H](C)[C@@H]1CCNC1 GBVBYEVLALCXBL-NKWVEPMBSA-N 0.000 description 1
SZUVGFMDDVSKSI-WIFOCOSTSA-N (1s,2s,3s,5r)-1-(carboxymethyl)-3,5-bis[(4-phenoxyphenyl)methyl-propylcarbamoyl]cyclopentane-1,2-dicarboxylic acid Chemical compound O=C([C@@H]1[C@@H]([C@](CC(O)=O)([C@H](C(=O)N(CCC)CC=2C=CC(OC=3C=CC=CC=3)=CC=2)C1)C(O)=O)C(O)=O)N(CCC)CC(C=C1)=CC=C1OC1=CC=CC=C1 SZUVGFMDDVSKSI-WIFOCOSTSA-N 0.000 description 1
VCDHLMWHIOUGCL-UHFFFAOYSA-N (2,4-dioxo-1h-quinazolin-3-yl)carbamic acid Chemical compound C1=CC=C2C(=O)N(NC(=O)O)C(=O)NC2=C1 VCDHLMWHIOUGCL-UHFFFAOYSA-N 0.000 description 1
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
IUSARDYWEPUTPN-OZBXUNDUSA-N (2r)-n-[(2s,3r)-4-[[(4s)-6-(2,2-dimethylpropyl)spiro[3,4-dihydropyrano[2,3-b]pyridine-2,1'-cyclobutane]-4-yl]amino]-3-hydroxy-1-[3-(1,3-thiazol-2-yl)phenyl]butan-2-yl]-2-methoxypropanamide Chemical compound C([C@H](NC(=O)[C@@H](C)OC)[C@H](O)CN[C@@H]1C2=CC(CC(C)(C)C)=CN=C2OC2(CCC2)C1)C(C=1)=CC=CC=1C1=NC=CS1 IUSARDYWEPUTPN-OZBXUNDUSA-N 0.000 description 1
YJLIKUSWRSEPSM-WGQQHEPDSA-N (2r,3r,4s,5r)-2-[6-amino-8-[(4-phenylphenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1CNC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O YJLIKUSWRSEPSM-WGQQHEPDSA-N 0.000 description 1
VIJSPAIQWVPKQZ-BLECARSGSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-acetamido-5-(diaminomethylideneamino)pentanoyl]amino]-4-methylpentanoyl]amino]-4,4-dimethylpentanoyl]amino]-4-methylpentanoyl]amino]propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid Chemical compound NC(=N)NCCC[C@@H](C(O)=O)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCNC(N)=N)NC(C)=O VIJSPAIQWVPKQZ-BLECARSGSA-N 0.000 description 1
WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
STBLNCCBQMHSRC-BATDWUPUSA-N (2s)-n-[(3s,4s)-5-acetyl-7-cyano-4-methyl-1-[(2-methylnaphthalen-1-yl)methyl]-2-oxo-3,4-dihydro-1,5-benzodiazepin-3-yl]-2-(methylamino)propanamide Chemical compound O=C1[C@@H](NC(=O)[C@H](C)NC)[C@H](C)N(C(C)=O)C2=CC(C#N)=CC=C2N1CC1=C(C)C=CC2=CC=CC=C12 STBLNCCBQMHSRC-BATDWUPUSA-N 0.000 description 1
NMQDTYHRKFPSSP-UHFFFAOYSA-N (3-hydroxypyrrolidin-3-yl)methylcarbamic acid Chemical compound OC(=O)NCC1(O)CCNC1 NMQDTYHRKFPSSP-UHFFFAOYSA-N 0.000 description 1
DEOXMCAZPVCALV-UHFFFAOYSA-N (3-methylpyrrolidin-3-yl)methylcarbamic acid Chemical compound OC(=O)NCC1(C)CCNC1 DEOXMCAZPVCALV-UHFFFAOYSA-N 0.000 description 1
WLFXFDRIZPXFFL-UHFFFAOYSA-N (3-phenylpyrrolidin-3-yl)methylcarbamic acid Chemical compound C=1C=CC=CC=1C1(CNC(=O)O)CCNC1 WLFXFDRIZPXFFL-UHFFFAOYSA-N 0.000 description 1
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
FNHHVPPSBFQMEL-KQHDFZBMSA-N (3S)-5-N-[(1S,5R)-3-hydroxy-6-bicyclo[3.1.0]hexanyl]-7-N,3-dimethyl-3-phenyl-2H-1-benzofuran-5,7-dicarboxamide Chemical compound CNC(=O)c1cc(cc2c1OC[C@@]2(C)c1ccccc1)C(=O)NC1[C@H]2CC(O)C[C@@H]12 FNHHVPPSBFQMEL-KQHDFZBMSA-N 0.000 description 1
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 1
UDQTXCHQKHIQMH-KYGLGHNPSA-N (3ar,5s,6s,7r,7ar)-5-(difluoromethyl)-2-(ethylamino)-5,6,7,7a-tetrahydro-3ah-pyrano[3,2-d][1,3]thiazole-6,7-diol Chemical compound S1C(NCC)=N[C@H]2[C@@H]1O[C@H](C(F)F)[C@@H](O)[C@@H]2O UDQTXCHQKHIQMH-KYGLGHNPSA-N 0.000 description 1
OOKAZRDERJMRCJ-KOUAFAAESA-N (3r)-7-[(1s,2s,4ar,6s,8s)-2,6-dimethyl-8-[(2s)-2-methylbutanoyl]oxy-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]-3-hydroxy-5-oxoheptanoic acid Chemical compound C1=C[C@H](C)[C@H](CCC(=O)C[C@@H](O)CC(O)=O)C2[C@@H](OC(=O)[C@@H](C)CC)C[C@@H](C)C[C@@H]21 OOKAZRDERJMRCJ-KOUAFAAESA-N 0.000 description 1
HUWSZNZAROKDRZ-RRLWZMAJSA-N (3r,4r)-3-azaniumyl-5-[[(2s,3r)-1-[(2s)-2,3-dicarboxypyrrolidin-1-yl]-3-methyl-1-oxopentan-2-yl]amino]-5-oxo-4-sulfanylpentane-1-sulfonate Chemical compound OS(=O)(=O)CC[C@@H](N)[C@@H](S)C(=O)N[C@@H]([C@H](C)CC)C(=O)N1CCC(C(O)=O)[C@H]1C(O)=O HUWSZNZAROKDRZ-RRLWZMAJSA-N 0.000 description 1
MPDDTAJMJCESGV-CTUHWIOQSA-M (3r,5r)-7-[2-(4-fluorophenyl)-5-[methyl-[(1r)-1-phenylethyl]carbamoyl]-4-propan-2-ylpyrazol-3-yl]-3,5-dihydroxyheptanoate Chemical compound C1([C@@H](C)N(C)C(=O)C2=NN(C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)=C2C(C)C)C=2C=CC(F)=CC=2)=CC=CC=C1 MPDDTAJMJCESGV-CTUHWIOQSA-M 0.000 description 1
CYLQMANYNUPGOT-UHFFFAOYSA-N (4-methylpyrrolidin-3-yl)carbamic acid Chemical compound CC1CNCC1NC(O)=O CYLQMANYNUPGOT-UHFFFAOYSA-N 0.000 description 1
AOZAXYOJIUHCOM-UHFFFAOYSA-N (4-methylpyrrolidin-3-yl)methylcarbamic acid Chemical compound CC1CNCC1CNC(O)=O AOZAXYOJIUHCOM-UHFFFAOYSA-N 0.000 description 1
YQOLEILXOBUDMU-KRWDZBQOSA-N (4R)-5-[(6-bromo-3-methyl-2-pyrrolidin-1-ylquinoline-4-carbonyl)amino]-4-(2-chlorophenyl)pentanoic acid Chemical compound CC1=C(C2=C(C=CC(=C2)Br)N=C1N3CCCC3)C(=O)NC[C@H](CCC(=O)O)C4=CC=CC=C4Cl YQOLEILXOBUDMU-KRWDZBQOSA-N 0.000 description 1
STPKWKPURVSAJF-LJEWAXOPSA-N (4r,5r)-5-[4-[[4-(1-aza-4-azoniabicyclo[2.2.2]octan-4-ylmethyl)phenyl]methoxy]phenyl]-3,3-dibutyl-7-(dimethylamino)-1,1-dioxo-4,5-dihydro-2h-1$l^{6}-benzothiepin-4-ol Chemical compound O[C@H]1C(CCCC)(CCCC)CS(=O)(=O)C2=CC=C(N(C)C)C=C2[C@H]1C(C=C1)=CC=C1OCC(C=C1)=CC=C1C[N+]1(CC2)CCN2CC1 STPKWKPURVSAJF-LJEWAXOPSA-N 0.000 description 1
125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
125000004890 (C1-C6) alkylamino group Chemical group 0.000 description 1
UUDAMDVQRQNNHZ-UHFFFAOYSA-N (S)-AMPA Chemical compound CC=1ONC(=O)C=1CC(N)C(O)=O UUDAMDVQRQNNHZ-UHFFFAOYSA-N 0.000 description 1
DEVSOMFAQLZNKR-RJRFIUFISA-N (z)-3-[3-[3,5-bis(trifluoromethyl)phenyl]-1,2,4-triazol-1-yl]-n'-pyrazin-2-ylprop-2-enehydrazide Chemical compound FC(F)(F)C1=CC(C(F)(F)F)=CC(C2=NN(\C=C/C(=O)NNC=3N=CC=NC=3)C=N2)=C1 DEVSOMFAQLZNKR-RJRFIUFISA-N 0.000 description 1
CZVXEAWVGZTLON-UHFFFAOYSA-N 1,1-dibenzylhydrazine Chemical compound C=1C=CC=CC=1CN(N)CC1=CC=CC=C1 CZVXEAWVGZTLON-UHFFFAOYSA-N 0.000 description 1
FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical group C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
GXNVARTZYHDDNN-UHFFFAOYSA-N 1,2-dibenzylhydrazine Chemical compound C=1C=CC=CC=1CNNCC1=CC=CC=C1 GXNVARTZYHDDNN-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
KKHFRAFPESRGGD-UHFFFAOYSA-N 1,3-dimethyl-7-[3-(n-methylanilino)propyl]purine-2,6-dione Chemical compound C1=NC=2N(C)C(=O)N(C)C(=O)C=2N1CCCN(C)C1=CC=CC=C1 KKHFRAFPESRGGD-UHFFFAOYSA-N 0.000 description 1
WLLFFDSRCIVDEH-UHFFFAOYSA-N 1-(1-benzyl-4-methylpyrrolidin-3-yl)ethanone Chemical compound C1C(C(C)=O)C(C)CN1CC1=CC=CC=C1 WLLFFDSRCIVDEH-UHFFFAOYSA-N 0.000 description 1
PSOOKVRLQJHUPX-UHFFFAOYSA-N 1-(1-benzylpiperidin-3-yl)ethanone Chemical compound C1C(C(=O)C)CCCN1CC1=CC=CC=C1 PSOOKVRLQJHUPX-UHFFFAOYSA-N 0.000 description 1
RQDVPDBLCOYTCI-UHFFFAOYSA-N 1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidine-3-carboxylic acid Chemical class FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)=O)C1 RQDVPDBLCOYTCI-UHFFFAOYSA-N 0.000 description 1
IXEXVNLAENSVFU-UHFFFAOYSA-N 1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)pyrrolidine-3-carboxylic acid;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(O)=O)C1 IXEXVNLAENSVFU-UHFFFAOYSA-N 0.000 description 1
XINWDGBDNMNJAK-UHFFFAOYSA-N 1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidine-3-carboxylic acid Chemical class FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(O)=O)C1 XINWDGBDNMNJAK-UHFFFAOYSA-N 0.000 description 1
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
GGAFVIDSRBQZNM-UHFFFAOYSA-N 1-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)ethylcarbamic acid Chemical compound C1C2(CC2)C(C(NC(O)=O)C)CN1CC1=CC=CC=C1 GGAFVIDSRBQZNM-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
WZZBNLYBHUDSHF-DHLKQENFSA-N 1-[(3s,4s)-4-[8-(2-chloro-4-pyrimidin-2-yloxyphenyl)-7-fluoro-2-methylimidazo[4,5-c]quinolin-1-yl]-3-fluoropiperidin-1-yl]-2-hydroxyethanone Chemical compound CC1=NC2=CN=C3C=C(F)C(C=4C(=CC(OC=5N=CC=CN=5)=CC=4)Cl)=CC3=C2N1[C@H]1CCN(C(=O)CO)C[C@@H]1F WZZBNLYBHUDSHF-DHLKQENFSA-N 0.000 description 1
LQKPQUMBUHULIA-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-4,4-dimethylpyrrolidin-3-yl]ethylcarbamic acid Chemical compound C1C(C)(C)C(C(NC(O)=O)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C LQKPQUMBUHULIA-UHFFFAOYSA-N 0.000 description 1
MLAHFMWDJKJGMB-UHFFFAOYSA-N 1-[1-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]propylcarbamic acid Chemical compound C1C(C(NC(O)=O)CC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C MLAHFMWDJKJGMB-UHFFFAOYSA-N 0.000 description 1
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 1
MWYPZZJIYMONNA-UHFFFAOYSA-N 1-[5-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-5-azaspiro[2.4]heptan-7-yl]ethylcarbamic acid Chemical compound OC(=O)NC(C)C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)C)CC11CC1 MWYPZZJIYMONNA-UHFFFAOYSA-N 0.000 description 1
AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
QXOGPTXQGKQSJT-UHFFFAOYSA-N 1-amino-4-[4-(3,4-dimethylphenyl)sulfanylanilino]-9,10-dioxoanthracene-2-sulfonic acid Chemical compound Cc1ccc(Sc2ccc(Nc3cc(c(N)c4C(=O)c5ccccc5C(=O)c34)S(O)(=O)=O)cc2)cc1C QXOGPTXQGKQSJT-UHFFFAOYSA-N 0.000 description 1
CWEGCQIIDCZZED-UHFFFAOYSA-N 1-benzylpyrrolidine Chemical compound C=1C=CC=CC=1CN1CCCC1 CWEGCQIIDCZZED-UHFFFAOYSA-N 0.000 description 1
PKJBWOWQJHHAHG-UHFFFAOYSA-N 1-bromo-4-phenylbenzene Chemical group C1=CC(Br)=CC=C1C1=CC=CC=C1 PKJBWOWQJHHAHG-UHFFFAOYSA-N 0.000 description 1
MYMSJFSOOQERIO-UHFFFAOYSA-N 1-bromodecane Chemical compound CCCCCCCCCCBr MYMSJFSOOQERIO-UHFFFAOYSA-N 0.000 description 1
NUADXLCTIFJIAU-UHFFFAOYSA-N 1-hydroxyquinazoline-2,4-dione Chemical class C1=CC=C2C(O)=NC(=O)N(O)C2=C1 NUADXLCTIFJIAU-UHFFFAOYSA-N 0.000 description 1
PABBOSQGQGQPFP-UHFFFAOYSA-N 1-piperidin-3-ylethylcarbamic acid Chemical compound OC(=O)NC(C)C1CCCNC1 PABBOSQGQGQPFP-UHFFFAOYSA-N 0.000 description 1
IAZVVLJAKNNSDF-UHFFFAOYSA-N 1-pyrrolidin-3-ylpropylcarbamic acid Chemical compound OC(=O)NC(CC)C1CCNC1 IAZVVLJAKNNSDF-UHFFFAOYSA-N 0.000 description 1
WKTIBPHCHGGVEN-UHFFFAOYSA-N 1-pyrrolidin-3-yltriazole Chemical compound C1NCCC1N1N=NC=C1 WKTIBPHCHGGVEN-UHFFFAOYSA-N 0.000 description 1
LUQFTTCSOIWEPL-UHFFFAOYSA-N 1h-quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)NC(=O)NC2=C1 LUQFTTCSOIWEPL-UHFFFAOYSA-N 0.000 description 1
NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 description 1
SFKRXQKJTIYUAG-UHFFFAOYSA-N 2,3,4,5-tetrafluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(F)=C1F SFKRXQKJTIYUAG-UHFFFAOYSA-N 0.000 description 1
JMVKZWLEXQRABZ-UHFFFAOYSA-N 2,3,4,6-tetrafluorobenzoic acid Chemical compound OC(=O)C1=C(F)C=C(F)C(F)=C1F JMVKZWLEXQRABZ-UHFFFAOYSA-N 0.000 description 1
CGMSFYATZQKRJY-UHFFFAOYSA-N 2,3,4-trifluoro-5-methoxybenzoic acid Chemical compound COC1=CC(C(O)=O)=C(F)C(F)=C1F CGMSFYATZQKRJY-UHFFFAOYSA-N 0.000 description 1
WEPXLRANFJEOFZ-UHFFFAOYSA-N 2,3,4-trifluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(F)=C1F WEPXLRANFJEOFZ-UHFFFAOYSA-N 0.000 description 1
PQXKWPLDPFFDJP-UHFFFAOYSA-N 2,3-dimethyloxirane Chemical compound CC1OC1C PQXKWPLDPFFDJP-UHFFFAOYSA-N 0.000 description 1
HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical class OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
VRGBBPYUJDPXBB-UHFFFAOYSA-N 2,4,5-trifluoro-3-methoxybenzamide Chemical compound COC1=C(F)C(F)=CC(C(N)=O)=C1F VRGBBPYUJDPXBB-UHFFFAOYSA-N 0.000 description 1
FAHOHDHMFSGTMT-UHFFFAOYSA-N 2,4,5-trifluoro-3-methylbenzamide Chemical compound CC1=C(F)C(F)=CC(C(N)=O)=C1F FAHOHDHMFSGTMT-UHFFFAOYSA-N 0.000 description 1
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 1
ZVYNUGSPFZCYEV-UHFFFAOYSA-N 2,6-dichloro-5-fluoropyridine-3-carboxamide Chemical compound NC(=O)C1=CC(F)=C(Cl)N=C1Cl ZVYNUGSPFZCYEV-UHFFFAOYSA-N 0.000 description 1
WGFNXGPBPIJYLI-UHFFFAOYSA-N 2,6-difluoro-3-[(3-fluorophenyl)sulfonylamino]-n-(3-methoxy-1h-pyrazolo[3,4-b]pyridin-5-yl)benzamide Chemical compound C1=C2C(OC)=NNC2=NC=C1NC(=O)C(C=1F)=C(F)C=CC=1NS(=O)(=O)C1=CC=CC(F)=C1 WGFNXGPBPIJYLI-UHFFFAOYSA-N 0.000 description 1
JZUPYBRYQINNRE-UHFFFAOYSA-N 2,6-dimethyl-1,4-dioxane Chemical compound CC1COCC(C)O1 JZUPYBRYQINNRE-UHFFFAOYSA-N 0.000 description 1
SMVBEBQIMKHMPS-UHFFFAOYSA-N 2,7-diazaspiro[4.4]nonan-2-ylcarbamic acid Chemical compound C1N(NC(=O)O)CCC11CNCC1 SMVBEBQIMKHMPS-UHFFFAOYSA-N 0.000 description 1
FQMZXMVHHKXGTM-UHFFFAOYSA-N 2-(1-adamantyl)-n-[2-[2-(2-hydroxyethylamino)ethylamino]quinolin-5-yl]acetamide Chemical compound C1C(C2)CC(C3)CC2CC13CC(=O)NC1=CC=CC2=NC(NCCNCCO)=CC=C21 FQMZXMVHHKXGTM-UHFFFAOYSA-N 0.000 description 1
VCUXVXLUOHDHKK-UHFFFAOYSA-N 2-(2-aminopyrimidin-4-yl)-4-(2-chloro-4-methoxyphenyl)-1,3-thiazole-5-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=C(C(N)=O)SC(C=2N=C(N)N=CC=2)=N1 VCUXVXLUOHDHKK-UHFFFAOYSA-N 0.000 description 1
QEBYEVQKHRUYPE-UHFFFAOYSA-N 2-(2-chlorophenyl)-5-[(1-methylpyrazol-3-yl)methyl]-4-[[methyl(pyridin-3-ylmethyl)amino]methyl]-1h-pyrazolo[4,3-c]pyridine-3,6-dione Chemical compound C1=CN(C)N=C1CN1C(=O)C=C2NN(C=3C(=CC=CC=3)Cl)C(=O)C2=C1CN(C)CC1=CC=CN=C1 QEBYEVQKHRUYPE-UHFFFAOYSA-N 0.000 description 1
IOHPVZBSOKLVMN-UHFFFAOYSA-N 2-(2-phenylethyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1CCC1=CC=CC=C1 IOHPVZBSOKLVMN-UHFFFAOYSA-N 0.000 description 1
HMNDBQMEXAAKNB-UHFFFAOYSA-N 2-(cyclobutylamino)-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=CC(NC2CCC2)=C(C(O)=O)C=C1F HMNDBQMEXAAKNB-UHFFFAOYSA-N 0.000 description 1
YJKOYUXWHZCWQD-UHFFFAOYSA-N 2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoic acid Chemical compound OC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OC)=C1NC1CC1 YJKOYUXWHZCWQD-UHFFFAOYSA-N 0.000 description 1
UTZVSIXTYYWUOB-USJZOSNVSA-N 2-[(1s,2s,4as,8as)-2-hydroxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-1h-naphthalen-1-yl]-n-methoxy-n-methylacetamide Chemical compound CC1(C)CCC[C@]2(C)[C@H](CC(=O)N(C)OC)[C@@](C)(O)CC[C@H]21 UTZVSIXTYYWUOB-USJZOSNVSA-N 0.000 description 1
NPHAGMZXMINCCX-ZCFIWIBFSA-N 2-[(3r)-pyrrolidin-3-yl]propan-2-amine Chemical compound CC(C)(N)[C@@H]1CCNC1 NPHAGMZXMINCCX-ZCFIWIBFSA-N 0.000 description 1
PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
PAYROHWFGZADBR-UHFFFAOYSA-N 2-[[4-amino-5-(5-iodo-4-methoxy-2-propan-2-ylphenoxy)pyrimidin-2-yl]amino]propane-1,3-diol Chemical compound C1=C(I)C(OC)=CC(C(C)C)=C1OC1=CN=C(NC(CO)CO)N=C1N PAYROHWFGZADBR-UHFFFAOYSA-N 0.000 description 1
VVCMGAUPZIKYTH-VGHSCWAPSA-N 2-acetyloxybenzoic acid;[(2s,3r)-4-(dimethylamino)-3-methyl-1,2-diphenylbutan-2-yl] propanoate;1,3,7-trimethylpurine-2,6-dione Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O.CN1C(=O)N(C)C(=O)C2=C1N=CN2C.C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 VVCMGAUPZIKYTH-VGHSCWAPSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
YSUIQYOGTINQIN-UZFYAQMZSA-N 2-amino-9-[(1S,6R,8R,9S,10R,15R,17R,18R)-8-(6-aminopurin-9-yl)-9,18-difluoro-3,12-dihydroxy-3,12-bis(sulfanylidene)-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.2.1.06,10]octadecan-17-yl]-1H-purin-6-one Chemical compound NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(S)(=O)O[C@@H]4[C@@H](COP(S)(=O)O[C@@H]2[C@@H]3F)O[C@H]([C@H]4F)N2C=NC3=C2N=CN=C3N)C(=O)N1 YSUIQYOGTINQIN-UZFYAQMZSA-N 0.000 description 1
TVTJUIAKQFIXCE-HUKYDQBMSA-N 2-amino-9-[(2R,3S,4S,5R)-4-fluoro-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-ynyl-1H-purine-6,8-dione Chemical compound NC=1NC(C=2N(C(N(C=2N=1)[C@@H]1O[C@@H]([C@H]([C@H]1O)F)CO)=O)CC#C)=O TVTJUIAKQFIXCE-HUKYDQBMSA-N 0.000 description 1
RWZYAGGXGHYGMB-WGGUOBTBSA-N 2-aminobenzoic acid Chemical class NC1=CC=CC=C1[14C](O)=O RWZYAGGXGHYGMB-WGGUOBTBSA-N 0.000 description 1
IKCLCGXPQILATA-UHFFFAOYSA-N 2-chlorobenzoic acid Chemical class OC(=O)C1=CC=CC=C1Cl IKCLCGXPQILATA-UHFFFAOYSA-N 0.000 description 1
NSTREUWFTAOOKS-UHFFFAOYSA-N 2-fluorobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1F NSTREUWFTAOOKS-UHFFFAOYSA-N 0.000 description 1
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
LFOIDLOIBZFWDO-UHFFFAOYSA-N 2-methoxy-6-[6-methoxy-4-[(3-phenylmethoxyphenyl)methoxy]-1-benzofuran-2-yl]imidazo[2,1-b][1,3,4]thiadiazole Chemical compound N1=C2SC(OC)=NN2C=C1C(OC1=CC(OC)=C2)=CC1=C2OCC(C=1)=CC=CC=1OCC1=CC=CC=C1 LFOIDLOIBZFWDO-UHFFFAOYSA-N 0.000 description 1
125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
NYRRUVSVBBNTLE-RGMNGODLSA-N 3,5-diamino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6,8-difluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=C(F)C(N)=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F NYRRUVSVBBNTLE-RGMNGODLSA-N 0.000 description 1
DFRAKBCRUYUFNT-UHFFFAOYSA-N 3,8-dicyclohexyl-2,4,7,9-tetrahydro-[1,3]oxazino[5,6-h][1,3]benzoxazine Chemical compound C1CCCCC1N1CC(C=CC2=C3OCN(C2)C2CCCCC2)=C3OC1 DFRAKBCRUYUFNT-UHFFFAOYSA-N 0.000 description 1
QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 description 1
WFOVEDJTASPCIR-UHFFFAOYSA-N 3-[(4-methyl-5-pyridin-4-yl-1,2,4-triazol-3-yl)methylamino]-n-[[2-(trifluoromethyl)phenyl]methyl]benzamide Chemical compound N=1N=C(C=2C=CN=CC=2)N(C)C=1CNC(C=1)=CC=CC=1C(=O)NCC1=CC=CC=C1C(F)(F)F WFOVEDJTASPCIR-UHFFFAOYSA-N 0.000 description 1
OGAHNKARIDOKQV-ZVWHLABXSA-N 3-amino-1-cyclopropyl-6-fluoro-5-methyl-7-[(3r)-3-[(1s)-1-(methylamino)ethyl]pyrrolidin-1-yl]quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@H](C)NC)CCN1C(C(=C1C)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 OGAHNKARIDOKQV-ZVWHLABXSA-N 0.000 description 1
NUKPEHITNMYIJU-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(C(C)(C)O)C1 NUKPEHITNMYIJU-UHFFFAOYSA-N 0.000 description 1
OABLQLFHKHMUBE-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-7-[3-(2-hydroxypropan-2-yl)pyrrolidin-1-yl]-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C(C)(C)O)C1 OABLQLFHKHMUBE-UHFFFAOYSA-N 0.000 description 1
ZTUBFPBEOXSOBF-ZVWHLABXSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methyl-7-[(3r)-3-[(1s)-1-(methylamino)ethyl]pyrrolidin-1-yl]quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@H](C)NC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C ZTUBFPBEOXSOBF-ZVWHLABXSA-N 0.000 description 1
CQYDQJPJKHGSKE-UHFFFAOYSA-N 3-amino-1-cyclopropyl-6-fluoro-8-methyl-7-pyrrolidin-1-ylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCCC1 CQYDQJPJKHGSKE-UHFFFAOYSA-N 0.000 description 1
HIXJJCBBONXIRA-UHFFFAOYSA-N 3-amino-7,8-difluoro-12-methyl-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione Chemical compound C1CC(C)N2C(=O)N(N)C(=O)C3=C2C1=C(F)C(F)=C3 HIXJJCBBONXIRA-UHFFFAOYSA-N 0.000 description 1
HHUCACXDAYMCFA-UHFFFAOYSA-N 3-amino-7-(3-amino-3-phenylpyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N(C1)CCC1(N)C1=CC=CC=C1 HHUCACXDAYMCFA-UHFFFAOYSA-N 0.000 description 1
SLJJPQUSFFGTCR-UHFFFAOYSA-N 3-amino-7-(3-amino-3-phenylpyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C12=C(Cl)C(N3CC(N)(CC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 SLJJPQUSFFGTCR-UHFFFAOYSA-N 0.000 description 1
PXQQPXJGZDLTNV-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-butan-2-yl-8-chloro-6-fluoroquinazoline-2,4-dione Chemical compound FC=1C=C2C(=O)N(N)C(=O)N(C(C)CC)C2=C(Cl)C=1N1CCC(N)C1 PXQQPXJGZDLTNV-UHFFFAOYSA-N 0.000 description 1
BINKEAZZEKWNAU-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-2,4-dioxoquinazoline-8-carbonitrile;hydrochloride Chemical compound Cl.C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C#N BINKEAZZEKWNAU-UHFFFAOYSA-N 0.000 description 1
WTPDWGFRACETEF-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(N)C1 WTPDWGFRACETEF-UHFFFAOYSA-N 0.000 description 1
ABMBUIMCAPOBEI-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(N)C1 ABMBUIMCAPOBEI-UHFFFAOYSA-N 0.000 description 1
UOJAWYVCPKBOKI-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-ethoxy-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OCC)=C1N1CCC(N)C1 UOJAWYVCPKBOKI-UHFFFAOYSA-N 0.000 description 1
FQNCDXCWYOAOPR-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoro-6-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.COC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(F)=C1N1CCC(N)C1 FQNCDXCWYOAOPR-UHFFFAOYSA-N 0.000 description 1
PLBHUCNDERAECD-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-8-fluoroquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F PLBHUCNDERAECD-UHFFFAOYSA-N 0.000 description 1
RKSAGDHXJJUAAZ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-6-chloro-1-cyclopropyl-8-fluoroquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.C1C(N)CCN1C1=C(Cl)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1F RKSAGDHXJJUAAZ-UHFFFAOYSA-N 0.000 description 1
XFCMILOJGNQNJQ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-(cyclobutylamino)-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(NC3CCC3)C2=C1Cl XFCMILOJGNQNJQ-UHFFFAOYSA-N 0.000 description 1
ZLIIPNMSQNFJNJ-UHFFFAOYSA-N 3-amino-7-(3-aminopyrrolidin-1-yl)-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl ZLIIPNMSQNFJNJ-UHFFFAOYSA-N 0.000 description 1
ZNLDFRNWTKWEOQ-DDWIOCJRSA-N 3-amino-7-[(3R)-3-aminopyrrolidin-1-yl]-8-chloro-6-fluoro-1-propan-2-ylquinazoline-2,4-dione 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC=1C=C2C(=O)N(N)C(=O)N(C(C)C)C2=C(Cl)C=1N1CC[C@@H](N)C1 ZNLDFRNWTKWEOQ-DDWIOCJRSA-N 0.000 description 1
AHOSTKCQPPBDLY-UTONKHPSSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H](C(C)(N)C)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F AHOSTKCQPPBDLY-UTONKHPSSA-N 0.000 description 1
LNQJOAGOEPQGMS-RFVHGSKJSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CC[C@@H](C(C)(C)N)C1 LNQJOAGOEPQGMS-RFVHGSKJSA-N 0.000 description 1
VOKNCJBYEYCFSK-SBSPUUFOSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H](C(C)(N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 VOKNCJBYEYCFSK-SBSPUUFOSA-N 0.000 description 1
ANKPYIGFKBCEHD-HNCPQSOCSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-1-ethyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC=1C=C2C(=O)N(N)C(=O)N(CC)C2=CC=1N1CC[C@@H](C(C)(C)N)C1 ANKPYIGFKBCEHD-HNCPQSOCSA-N 0.000 description 1
RSRHECKHQUFWDS-SBSPUUFOSA-N 3-amino-7-[(3r)-3-(2-aminopropan-2-yl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H](C(C)(N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl RSRHECKHQUFWDS-SBSPUUFOSA-N 0.000 description 1
DYOPBGVIQJYWKT-OULXEKPRSA-N 3-amino-7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 DYOPBGVIQJYWKT-OULXEKPRSA-N 0.000 description 1
UBCKVMOGDJVZRS-OULXEKPRSA-N 3-amino-7-[(3r)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl UBCKVMOGDJVZRS-OULXEKPRSA-N 0.000 description 1
UMMNGHVJQVQNQO-JHQAJZDGSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](CN)[C@H](C(F)(F)F)C1 UMMNGHVJQVQNQO-JHQAJZDGSA-N 0.000 description 1
FRJNGFKFXGJMPL-YZUKSGEXSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-(trifluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](C(F)(F)F)[C@H](CN)CN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 FRJNGFKFXGJMPL-YZUKSGEXSA-N 0.000 description 1
NYLXPTOBPUBAKP-DAIXLEOSSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](F)[C@H](CN)C1 NYLXPTOBPUBAKP-DAIXLEOSSA-N 0.000 description 1
GVOQJEQGINSQJQ-DHTOPLTISA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](CN)C1 GVOQJEQGINSQJQ-DHTOPLTISA-N 0.000 description 1
UKSGWMYWSATPLA-FOKYBFFNSA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C UKSGWMYWSATPLA-FOKYBFFNSA-N 0.000 description 1
IMFRQKZCUZONHJ-VTLYIQCISA-N 3-amino-7-[(3r,4s)-3-(aminomethyl)-4-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](CN)[C@H](C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl IMFRQKZCUZONHJ-VTLYIQCISA-N 0.000 description 1
ZYADQXOQEXVASL-DHXVBOOMSA-N 3-amino-7-[(3s)-3-[(1r)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-5-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H]([C@H](N)C)CCN1C(C(=C1C)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 ZYADQXOQEXVASL-DHXVBOOMSA-N 0.000 description 1
WARILAOSVCTZHW-IYPAPVHQSA-N 3-amino-7-[(3s)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC[C@H]([C@H](C)N)C1 WARILAOSVCTZHW-IYPAPVHQSA-N 0.000 description 1
CEZGKXLXBJRIIA-ACMTZBLWSA-N 3-amino-7-[(3s)-3-[(1s)-1-aminoethyl]pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C CEZGKXLXBJRIIA-ACMTZBLWSA-N 0.000 description 1
JXFUCHOBQBAYQT-PPHPATTJSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-(cyclopropylmethyl)-8-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C1=CC=C2C(=O)N(N)C(=O)N(CC3CC3)C2=C1F JXFUCHOBQBAYQT-PPHPATTJSA-N 0.000 description 1
BCAHPRGZPFKUGT-FJXQXJEOSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C(C(=C1)F)=NC2=C1C(=O)N(N)C(=O)N2C1CC1 BCAHPRGZPFKUGT-FJXQXJEOSA-N 0.000 description 1
BPEVIOTUMZJAOB-QRPNPIFTSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](N)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 BPEVIOTUMZJAOB-QRPNPIFTSA-N 0.000 description 1
AMVCSCAODIKALF-QRPNPIFTSA-N 3-amino-7-[(3s)-3-aminopyrrolidin-1-yl]-1-ethyl-8-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C=1C=C2C(=O)N(N)C(=O)N(CC)C2=C(F)C=1N1CC[C@H](N)C1 AMVCSCAODIKALF-QRPNPIFTSA-N 0.000 description 1
JUGFRRIJVWAKOP-KUARMEPBSA-N 3-amino-7-[(3s,4r)-3-amino-4-(4-hydroxyphenyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=C(O)C=C1 JUGFRRIJVWAKOP-KUARMEPBSA-N 0.000 description 1
RURUAHSSUDTPRG-GHXDPTCOSA-N 3-amino-7-[(3s,4r)-3-amino-4-(trifluoromethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1[C@@H](C(F)(F)F)[C@H](N)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl RURUAHSSUDTPRG-GHXDPTCOSA-N 0.000 description 1
MKZORZFZIUDMEU-DAIXLEOSSA-N 3-amino-7-[(3s,4r)-3-amino-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1C[C@@H](C)[C@H](N)C1 MKZORZFZIUDMEU-DAIXLEOSSA-N 0.000 description 1
IQUDLNDPTUIKCB-KUARMEPBSA-N 3-amino-7-[(3s,4r)-3-amino-4-phenylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1([C@@H]2CN(C[C@H]2N)C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)=CC=CC=C1 IQUDLNDPTUIKCB-KUARMEPBSA-N 0.000 description 1
VYVNZMMXSHNJES-RFVHGSKJSA-N 3-amino-7-[(7s)-7-amino-5-azaspiro[2.4]heptan-5-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C([C@H]1N)N(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC11CC1 VYVNZMMXSHNJES-RFVHGSKJSA-N 0.000 description 1
AUHAELJWTZSXSM-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-3-fluoropyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(F)(C(C)N)C1 AUHAELJWTZSXSM-UHFFFAOYSA-N 0.000 description 1
NHCRTLNFBXYYDH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-3-methoxypyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(OC)(C(C)N)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NHCRTLNFBXYYDH-UHFFFAOYSA-N 0.000 description 1
RMTXVPQSJMHJQZ-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C)C(C(C)N)C1 RMTXVPQSJMHJQZ-UHFFFAOYSA-N 0.000 description 1
SNMVABNRCFRALH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)-4-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C SNMVABNRCFRALH-UHFFFAOYSA-N 0.000 description 1
KSHGSPOSLMZZAJ-UHFFFAOYSA-N 3-amino-7-[3-(1-aminoethyl)piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCCC(C(C)N)C1 KSHGSPOSLMZZAJ-UHFFFAOYSA-N 0.000 description 1
NCENSWFJWDJDIH-UHFFFAOYSA-N 3-amino-7-[3-(1-aminopropyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C(N)CC)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C NCENSWFJWDJDIH-UHFFFAOYSA-N 0.000 description 1
AXGMDASHCPHNPD-UHFFFAOYSA-N 3-amino-7-[3-(2-aminoethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CCN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl AXGMDASHCPHNPD-UHFFFAOYSA-N 0.000 description 1
XRJWZFHAORTBPI-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-(fluoromethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)(CF)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 XRJWZFHAORTBPI-UHFFFAOYSA-N 0.000 description 1
QUCCIKPDPPTAMJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-(methoxymethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(COC)(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C QUCCIKPDPPTAMJ-UHFFFAOYSA-N 0.000 description 1
MZNCQIAYNOZRLW-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-benzylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1CN(C=2C(=C3C(C(N(N)C(=O)N3C3CC3)=O)=CC=2F)Cl)CC1(CN)CC1=CC=CC=C1 MZNCQIAYNOZRLW-UHFFFAOYSA-N 0.000 description 1
BOQGXRFIZBKXCA-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(C)(CN)C1 BOQGXRFIZBKXCA-UHFFFAOYSA-N 0.000 description 1
MJEXVZKNLWYGMW-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)-3-methylpyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C)(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl MJEXVZKNLWYGMW-UHFFFAOYSA-N 0.000 description 1
ILRKEDGPSROFJA-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)piperidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)CCCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl ILRKEDGPSROFJA-UHFFFAOYSA-N 0.000 description 1
DHZKFGGXIOSWDX-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 DHZKFGGXIOSWDX-UHFFFAOYSA-N 0.000 description 1
HUXFMNVSPFSMDJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(C)=C1N1CCC(CN)C1 HUXFMNVSPFSMDJ-UHFFFAOYSA-N 0.000 description 1
ZGWNSOGHYLBQOJ-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 ZGWNSOGHYLBQOJ-UHFFFAOYSA-N 0.000 description 1
HSDRQRXLMXJWQS-UHFFFAOYSA-N 3-amino-7-[3-(aminomethyl)pyrrolidin-1-yl]-8-chloro-1-cyclopropyl-6-fluoroquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CN)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl HSDRQRXLMXJWQS-UHFFFAOYSA-N 0.000 description 1
PCPFOUWNFJLCLB-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CC(C(C)N)C(C)(C)C1 PCPFOUWNFJLCLB-UHFFFAOYSA-N 0.000 description 1
MFUNKJCFFMYGIK-UHFFFAOYSA-N 3-amino-7-[4-(1-aminoethyl)-3,3-dimethylpyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-8-methylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(C)(C)C(C(N)C)CN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1C MFUNKJCFFMYGIK-UHFFFAOYSA-N 0.000 description 1
YSXPQFLFRPAOMJ-UHFFFAOYSA-N 3-amino-7-[7-(aminomethyl)-5-azaspiro[2.4]heptan-5-yl]-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C(=O)N2C3CC3)=O)=C2C(OC)=C1N(C1)CC(CN)C21CC2 YSXPQFLFRPAOMJ-UHFFFAOYSA-N 0.000 description 1
OCHAJWBUVYEKDG-UHFFFAOYSA-N 3-amino-7-bromo-1h-quinazoline-2,4-dione Chemical compound BrC1=CC=C2C(=O)N(N)C(=O)NC2=C1 OCHAJWBUVYEKDG-UHFFFAOYSA-N 0.000 description 1
IXMOSZFSLFLSBD-JOJLQXQQSA-N 3-amino-8-[(3R)-3-[(1S)-1-aminoethyl]pyrrolidin-1-yl]-7-fluoro-12-methyl-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione hydrochloride Chemical compound Cl.C1[C@H]([C@@H](N)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N3C(C)CCC1=C32 IXMOSZFSLFLSBD-JOJLQXQQSA-N 0.000 description 1
AJISAFYWCLOWCA-MTICXXPYSA-N 3-amino-8-[(3S)-3-aminopyrrolidin-1-yl]-7-fluoro-12-methyl-10-oxa-1,3-diazatricyclo[7.3.1.05,13]trideca-5,7,9(13)-triene-2,4-dione hydrochloride Chemical compound Cl.FC1=CC(C(N(N)C2=O)=O)=C3N2C(C)COC3=C1N1CC[C@H](N)C1 AJISAFYWCLOWCA-MTICXXPYSA-N 0.000 description 1
POXFJYXPBAXTHZ-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-(2-methyl-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-5-yl)quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C2CN(C)CC2CN1C(C=1Cl)=C(F)C=C(C(N(N)C2=O)=O)C=1N2C1CC1 POXFJYXPBAXTHZ-UHFFFAOYSA-N 0.000 description 1
AEEWOZDXOCLUPA-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-[(2,2,2-trifluoroethylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C12=C(Cl)C(N3CC(CNCC(F)(F)F)CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 AEEWOZDXOCLUPA-UHFFFAOYSA-N 0.000 description 1
NZWNGIYRNKGBCQ-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-[3-[(propan-2-ylamino)methyl]pyrrolidin-1-yl]quinazoline-2,4-dione;hydrochloride Chemical compound Cl.C1C(CNC(C)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl NZWNGIYRNKGBCQ-UHFFFAOYSA-N 0.000 description 1
GPQVYMFUYZXKIE-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-piperazin-1-ylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C12=C(Cl)C(N3CCNCC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 GPQVYMFUYZXKIE-UHFFFAOYSA-N 0.000 description 1
GHOZFQGUXIOVQO-UHFFFAOYSA-N 3-amino-8-chloro-1-cyclopropyl-6-fluoro-7-pyrrolidin-1-ylquinazoline-2,4-dione;hydrochloride Chemical compound Cl.C12=C(Cl)C(N3CCCC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 GHOZFQGUXIOVQO-UHFFFAOYSA-N 0.000 description 1
NSFFUUCTCIWHRO-UHFFFAOYSA-N 3-chloro-2-(cyclopropylamino)-4,5-difluorobenzoic acid Chemical compound OC(=O)C1=CC(F)=C(F)C(Cl)=C1NC1CC1 NSFFUUCTCIWHRO-UHFFFAOYSA-N 0.000 description 1
FPHNWFFKQCPXPI-UHFFFAOYSA-N 3-chlorooxolane Chemical compound ClC1CCOC1 FPHNWFFKQCPXPI-UHFFFAOYSA-N 0.000 description 1
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
YNGXHRRTAUOVKC-UHFFFAOYSA-N 3-ethyl-2,4,5-trifluorobenzoic acid Chemical compound CCC1=C(F)C(F)=CC(C(O)=O)=C1F YNGXHRRTAUOVKC-UHFFFAOYSA-N 0.000 description 1
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 1
TZZSQUATPYDROZ-UHFFFAOYSA-N 3-hydroxy-1h-quinazoline-2,4-dione Chemical class C1=CC=C2C(=O)N(O)C(=O)NC2=C1 TZZSQUATPYDROZ-UHFFFAOYSA-N 0.000 description 1
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 description 1
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 description 1
WYFCZWSWFGJODV-MIANJLSGSA-N 4-[[(1s)-2-[(e)-3-[3-chloro-2-fluoro-6-(tetrazol-1-yl)phenyl]prop-2-enoyl]-5-(4-methyl-2-oxopiperazin-1-yl)-3,4-dihydro-1h-isoquinoline-1-carbonyl]amino]benzoic acid Chemical compound O=C1CN(C)CCN1C1=CC=CC2=C1CCN(C(=O)\C=C\C=1C(=CC=C(Cl)C=1F)N1N=NN=C1)[C@@H]2C(=O)NC1=CC=C(C(O)=O)C=C1 WYFCZWSWFGJODV-MIANJLSGSA-N 0.000 description 1
MPMKMQHJHDHPBE-RUZDIDTESA-N 4-[[(2r)-1-(1-benzothiophene-3-carbonyl)-2-methylazetidine-2-carbonyl]-[(3-chlorophenyl)methyl]amino]butanoic acid Chemical compound O=C([C@@]1(N(CC1)C(=O)C=1C2=CC=CC=C2SC=1)C)N(CCCC(O)=O)CC1=CC=CC(Cl)=C1 MPMKMQHJHDHPBE-RUZDIDTESA-N 0.000 description 1
GSDQYSSLIKJJOG-UHFFFAOYSA-N 4-chloro-2-(3-chloroanilino)benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1NC1=CC=CC(Cl)=C1 GSDQYSSLIKJJOG-UHFFFAOYSA-N 0.000 description 1
DQAZPZIYEOGZAF-UHFFFAOYSA-N 4-ethyl-n-[4-(3-ethynylanilino)-7-methoxyquinazolin-6-yl]piperazine-1-carboxamide Chemical compound C1CN(CC)CCN1C(=O)NC(C(=CC1=NC=N2)OC)=CC1=C2NC1=CC=CC(C#C)=C1 DQAZPZIYEOGZAF-UHFFFAOYSA-N 0.000 description 1
125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical compound [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 description 1
VKLKXFOZNHEBSW-UHFFFAOYSA-N 5-[[3-[(4-morpholin-4-ylbenzoyl)amino]phenyl]methoxy]pyridine-3-carboxamide Chemical compound O1CCN(CC1)C1=CC=C(C(=O)NC=2C=C(COC=3C=NC=C(C(=O)N)C=3)C=CC=2)C=C1 VKLKXFOZNHEBSW-UHFFFAOYSA-N 0.000 description 1
NDFCFTOWEKYFMV-UHFFFAOYSA-N 5-amino-1h-quinazoline-2,4-dione Chemical group N1C(=O)NC(=O)C2=C1C=CC=C2N NDFCFTOWEKYFMV-UHFFFAOYSA-N 0.000 description 1
JJPJLAXRRONNTI-UHFFFAOYSA-N 5-azaspiro[2.4]heptan-7-ylcarbamic acid Chemical compound C1CC12CNCC2NC(=O)O JJPJLAXRRONNTI-UHFFFAOYSA-N 0.000 description 1
XFJBGINZIMNZBW-CRAIPNDOSA-N 5-chloro-2-[4-[(1r,2s)-2-[2-(5-methylsulfonylpyridin-2-yl)oxyethyl]cyclopropyl]piperidin-1-yl]pyrimidine Chemical compound N1=CC(S(=O)(=O)C)=CC=C1OCC[C@H]1[C@@H](C2CCN(CC2)C=2N=CC(Cl)=CN=2)C1 XFJBGINZIMNZBW-CRAIPNDOSA-N 0.000 description 1
LGZVTHNZIAOAKM-UHFFFAOYSA-N 5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2-(propan-2-ylamino)benzoic acid Chemical compound C1=C(C(O)=O)C(NC(C)C)=CC(N2CC(CC2)NC(=O)OC(C)(C)C)=C1F LGZVTHNZIAOAKM-UHFFFAOYSA-N 0.000 description 1
YQURLNGUWNDBIR-UHFFFAOYSA-N 5-methyl-2,3,3a,4,6,6a-hexahydro-1h-pyrrolo[3,4-c]pyrrole Chemical compound C1NCC2CN(C)CC21 YQURLNGUWNDBIR-UHFFFAOYSA-N 0.000 description 1
UHSGELRYPQABHF-UHFFFAOYSA-N 5-methyl-3-azabicyclo[3.2.0]heptan-7-amine Chemical compound C1NCC2(C)C1C(N)C2 UHSGELRYPQABHF-UHFFFAOYSA-N 0.000 description 1
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 description 1
OYWCDOHPMUVCFN-UHFFFAOYSA-N 6-(3-amino-1-cyclopropyl-6-fluoro-8-methyl-2,4-dioxoquinazolin-7-yl)-3,4,4a,5,7,7a-hexahydro-2h-pyrrolo[3,4-b]pyridine-1-carboxylic acid Chemical class CC1=C(N2CC3N(CCCC3C2)C(O)=O)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 OYWCDOHPMUVCFN-UHFFFAOYSA-N 0.000 description 1
RSIWALKZYXPAGW-NSHDSACASA-N 6-(3-fluorophenyl)-3-methyl-7-[(1s)-1-(7h-purin-6-ylamino)ethyl]-[1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound C=1([C@@H](NC=2C=3N=CNC=3N=CN=2)C)N=C2SC=C(C)N2C(=O)C=1C1=CC=CC(F)=C1 RSIWALKZYXPAGW-NSHDSACASA-N 0.000 description 1
GDUANFXPOZTYKS-UHFFFAOYSA-N 6-bromo-8-[(2,6-difluoro-4-methoxybenzoyl)amino]-4-oxochromene-2-carboxylic acid Chemical compound FC1=CC(OC)=CC(F)=C1C(=O)NC1=CC(Br)=CC2=C1OC(C(O)=O)=CC2=O GDUANFXPOZTYKS-UHFFFAOYSA-N 0.000 description 1
XBMWHBCGUKOIGL-UHFFFAOYSA-N 7,8-difluoro-3-methyl-3,4-dihydro-2h-1,4-benzoxazine;hydrochloride Chemical compound Cl.FC1=CC=C2NC(C)COC2=C1F XBMWHBCGUKOIGL-UHFFFAOYSA-N 0.000 description 1
UXLHZNHLPYLLAW-UHFFFAOYSA-N 7-(1,3,3a,4,5,6,7,7a-octahydropyrrolo[3,4-c]pyridin-2-yl)-3-amino-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C12=NC(N3CC4CNCCC4C3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 UXLHZNHLPYLLAW-UHFFFAOYSA-N 0.000 description 1
HUFSQBIRTKFYRD-UHFFFAOYSA-N 7-(2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridin-2-yl)-3-amino-1-cyclopropyl-6-fluoropyrido[2,3-d]pyrimidine-2,4-dione;hydrochloride Chemical compound Cl.C12=NC(C3NC4CNCC4CC3)=C(F)C=C2C(=O)N(N)C(=O)N1C1CC1 HUFSQBIRTKFYRD-UHFFFAOYSA-N 0.000 description 1
HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 1
QSTSJYPYHUDKGT-UHFFFAOYSA-N 7-[7a-(aminomethyl)-3,3a,4,5,6,7-hexahydro-1h-isoindol-2-yl]-3-amino-1-cyclopropyl-6-fluoro-8-methoxyquinazoline-2,4-dione;hydrochloride Chemical compound Cl.COC1=C(N2CC3(CN)CCCCC3C2)C(F)=CC(C(N(N)C2=O)=O)=C1N2C1CC1 QSTSJYPYHUDKGT-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
YPKUTBCKHJBNKX-UHFFFAOYSA-N 8-bromo-5,6-difluoro-2-methylquinoline Chemical compound FC1=C(F)C=C(Br)C2=NC(C)=CC=C21 YPKUTBCKHJBNKX-UHFFFAOYSA-N 0.000 description 1
KPNLVIRHPYBGCQ-VIFPVBQESA-N 8-chloro-1-cyclopropyl-6-fluoro-3-(methylamino)-7-[(3s)-3-(methylamino)pyrrolidin-1-yl]quinazoline-2,4-dione Chemical compound C1[C@@H](NC)CCN1C1=C(F)C=C2C(=O)N(NC)C(=O)N(C3CC3)C2=C1Cl KPNLVIRHPYBGCQ-VIFPVBQESA-N 0.000 description 1
XASOHFCUIQARJT-UHFFFAOYSA-N 8-methoxy-6-[7-(2-morpholin-4-ylethoxy)imidazo[1,2-a]pyridin-3-yl]-2-(2,2,2-trifluoroethyl)-3,4-dihydroisoquinolin-1-one Chemical compound C(N1C(=O)C2=C(OC)C=C(C=3N4C(=NC=3)C=C(C=C4)OCCN3CCOCC3)C=C2CC1)C(F)(F)F XASOHFCUIQARJT-UHFFFAOYSA-N 0.000 description 1
IRBAWVGZNJIROV-SFHVURJKSA-N 9-(2-cyclopropylethynyl)-2-[[(2s)-1,4-dioxan-2-yl]methoxy]-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one Chemical compound C1=C2C3=CC=C(C#CC4CC4)C=C3CCN2C(=O)N=C1OC[C@@H]1COCCO1 IRBAWVGZNJIROV-SFHVURJKSA-N 0.000 description 1
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
IYHHRZBKXXKDDY-UHFFFAOYSA-N BI-605906 Chemical compound N=1C=2SC(C(N)=O)=C(N)C=2C(C(F)(F)CC)=CC=1N1CCC(S(C)(=O)=O)CC1 IYHHRZBKXXKDDY-UHFFFAOYSA-N 0.000 description 1
229910000906 Bronze Inorganic materials 0.000 description 1
JXBFWRHKTAPMLX-UHFFFAOYSA-N C(C)(C)(C)OC(=O)NCC1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1Cl)C1CC1)=O)NC(O)=O)=O)F Chemical compound C(C)(C)(C)OC(=O)NCC1CN(CC1)C1=C(C=C2C(N(C(N(C2=C1Cl)C1CC1)=O)NC(O)=O)=O)F JXBFWRHKTAPMLX-UHFFFAOYSA-N 0.000 description 1
JQUCWIWWWKZNCS-LESHARBVSA-N C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F Chemical compound C(C1=CC=CC=C1)(=O)NC=1SC[C@H]2[C@@](N1)(CO[C@H](C2)C)C=2SC=C(N2)NC(=O)C2=NC=C(C=C2)OC(F)F JQUCWIWWWKZNCS-LESHARBVSA-N 0.000 description 1
XAXVZWFMYBMFHS-BAUSSPIASA-N C(N)(O)=O.OC1=CC=C(C=C1)[C@H]1[C@@H](CNC1)N Chemical compound C(N)(O)=O.OC1=CC=C(C=C1)[C@H]1[C@@H](CNC1)N XAXVZWFMYBMFHS-BAUSSPIASA-N 0.000 description 1
ZWTRWPKVEDPSHZ-UHFFFAOYSA-N C1=CC=C(C=C1)C(=O)N(C(=O)O)NCl Chemical compound C1=CC=C(C=C1)C(=O)N(C(=O)O)NCl ZWTRWPKVEDPSHZ-UHFFFAOYSA-N 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
125000003601 C2-C6 alkynyl group Chemical group 0.000 description 1
KCBAMQOKOLXLOX-BSZYMOERSA-N CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O Chemical compound CC1=C(SC=N1)C2=CC=C(C=C2)[C@H](C)NC(=O)[C@@H]3C[C@H](CN3C(=O)[C@H](C(C)(C)C)NC(=O)CCCCCCCCCCNCCCONC(=O)C4=C(C(=C(C=C4)F)F)NC5=C(C=C(C=C5)I)F)O KCBAMQOKOLXLOX-BSZYMOERSA-N 0.000 description 1
UHNRLQRZRNKOKU-UHFFFAOYSA-N CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O Chemical compound CCN(CC1=NC2=C(N1)C1=CC=C(C=C1N=C2N)C1=NNC=C1)C(C)=O UHNRLQRZRNKOKU-UHFFFAOYSA-N 0.000 description 1
BQXUPNKLZNSUMC-YUQWMIPFSA-N CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 Chemical compound CCN(CCCCCOCC(=O)N[C@H](C(=O)N1C[C@H](O)C[C@H]1C(=O)N[C@@H](C)c1ccc(cc1)-c1scnc1C)C(C)(C)C)CCOc1ccc(cc1)C(=O)c1c(sc2cc(O)ccc12)-c1ccc(O)cc1 BQXUPNKLZNSUMC-YUQWMIPFSA-N 0.000 description 1
PKMUHQIDVVOXHQ-HXUWFJFHSA-N C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O Chemical compound C[C@H](C1=CC(C2=CC=C(CNC3CCCC3)S2)=CC=C1)NC(C1=C(C)C=CC(NC2CNC2)=C1)=O PKMUHQIDVVOXHQ-HXUWFJFHSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
229940126657 Compound 17 Drugs 0.000 description 1
229940126639 Compound 33 Drugs 0.000 description 1
229940127007 Compound 39 Drugs 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
OCUCCJIRFHNWBP-IYEMJOQQSA-L Copper gluconate Chemical class [Cu+2].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O OCUCCJIRFHNWBP-IYEMJOQQSA-L 0.000 description 1
GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
OHQAQYCNTCMTJB-AWEZNQCLSA-N FC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(Cl)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 Chemical compound FC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(Cl)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 OHQAQYCNTCMTJB-AWEZNQCLSA-N 0.000 description 1
RRSNDVCODIMOFX-MPKOGUQCSA-N Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O Chemical compound Fc1c(Cl)cccc1[C@H]1[C@@H](NC2(CCCCC2)[C@@]11C(=O)Nc2cc(Cl)ccc12)C(=O)Nc1ccc(cc1)C(=O)NCCCCCc1cccc2C(=O)N(Cc12)C1CCC(=O)NC1=O RRSNDVCODIMOFX-MPKOGUQCSA-N 0.000 description 1
KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 1
LVDRREOUMKACNJ-BKMJKUGQSA-N N-[(2R,3S)-2-(4-chlorophenyl)-1-(1,4-dimethyl-2-oxoquinolin-7-yl)-6-oxopiperidin-3-yl]-2-methylpropane-1-sulfonamide Chemical compound CC(C)CS(=O)(=O)N[C@H]1CCC(=O)N([C@@H]1c1ccc(Cl)cc1)c1ccc2c(C)cc(=O)n(C)c2c1 LVDRREOUMKACNJ-BKMJKUGQSA-N 0.000 description 1
DEYZMJLCNCAWDK-UHFFFAOYSA-N N-[1-(1-benzyl-4,4-dimethylpyrrolidin-3-yl)ethylidene]hydroxylamine Chemical compound C1C(C)(C)C(C(=NO)C)CN1CC1=CC=CC=C1 DEYZMJLCNCAWDK-UHFFFAOYSA-N 0.000 description 1
AVYVHIKSFXVDBG-UHFFFAOYSA-N N-benzyl-N-hydroxy-2,2-dimethylbutanamide Chemical compound C(C1=CC=CC=C1)N(C(C(CC)(C)C)=O)O AVYVHIKSFXVDBG-UHFFFAOYSA-N 0.000 description 1
POFVJRKJJBFPII-UHFFFAOYSA-N N-cyclopentyl-5-[2-[[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]amino]-5-fluoropyrimidin-4-yl]-4-methyl-1,3-thiazol-2-amine Chemical compound C1(CCCC1)NC=1SC(=C(N=1)C)C1=NC(=NC=C1F)NC1=NC=C(C=C1)CN1CCN(CC1)CC POFVJRKJJBFPII-UHFFFAOYSA-N 0.000 description 1
MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
OPFJDXRVMFKJJO-ZHHKINOHSA-N N-{[3-(2-benzamido-4-methyl-1,3-thiazol-5-yl)-pyrazol-5-yl]carbonyl}-G-dR-G-dD-dD-dD-NH2 Chemical compound S1C(C=2NN=C(C=2)C(=O)NCC(=O)N[C@H](CCCN=C(N)N)C(=O)NCC(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC(O)=O)C(N)=O)=C(C)N=C1NC(=O)C1=CC=CC=C1 OPFJDXRVMFKJJO-ZHHKINOHSA-N 0.000 description 1
IUIWQSOJQJOXPV-GFCCVEGCSA-N N1([C@@H]2CCN(C2)C2=C(F)C=C(C(=C2Cl)NC2CC2)C(=O)OCC)C=CN=N1 Chemical compound N1([C@@H]2CCN(C2)C2=C(F)C=C(C(=C2Cl)NC2CC2)C(=O)OCC)C=CN=N1 IUIWQSOJQJOXPV-GFCCVEGCSA-N 0.000 description 1
CSBJFWVEVCNEFA-UHFFFAOYSA-N NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(C(C1)C)CNC(O)=O)C)C1CC1)=O Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1CC(C(C1)C)CNC(O)=O)C)C1CC1)=O CSBJFWVEVCNEFA-UHFFFAOYSA-N 0.000 description 1
QOVYHDHLFPKQQG-NDEPHWFRSA-N N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O Chemical compound N[C@@H](CCC(=O)N1CCC(CC1)NC1=C2C=CC=CC2=NC(NCC2=CN(CCCNCCCNC3CCCCC3)N=N2)=N1)C(O)=O QOVYHDHLFPKQQG-NDEPHWFRSA-N 0.000 description 1
FYVBUMABRLOPIH-QRPNPIFTSA-N OC(=O)C(F)(F)F.FC=1C=C2C(=O)N(N)C(=O)N([C@@H](C)CC)C2=C(Cl)C=1N1CCC(N)=C1 Chemical compound OC(=O)C(F)(F)F.FC=1C=C2C(=O)N(N)C(=O)N([C@@H](C)CC)C2=C(Cl)C=1N1CCC(N)=C1 FYVBUMABRLOPIH-QRPNPIFTSA-N 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
108091000080 Phosphotransferase Proteins 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
PNUZDKCDAWUEGK-CYZMBNFOSA-N Sitafloxacin Chemical compound C([C@H]1N)N(C=2C(=C3C(C(C(C(O)=O)=CN3[C@H]3[C@H](C3)F)=O)=CC=2F)Cl)CC11CC1 PNUZDKCDAWUEGK-CYZMBNFOSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
KZVWEOXAPZXAFB-BQFCYCMXSA-N Temocaprilat Chemical compound C([C@H](N[C@H]1CS[C@@H](CN(C1=O)CC(=O)O)C=1SC=CC=1)C(O)=O)CC1=CC=CC=C1 KZVWEOXAPZXAFB-BQFCYCMXSA-N 0.000 description 1
101710183280 Topoisomerase Proteins 0.000 description 1
DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
LJOOWESTVASNOG-UFJKPHDISA-N [(1s,3r,4ar,7s,8s,8as)-3-hydroxy-8-[2-[(4r)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-1-yl] (2s)-2-methylbutanoate Chemical compound C([C@H]1[C@@H](C)C=C[C@H]2C[C@@H](O)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)CC1C[C@@H](O)CC(=O)O1 LJOOWESTVASNOG-UFJKPHDISA-N 0.000 description 1
SPXSEZMVRJLHQG-XMMPIXPASA-N [(2R)-1-[[4-[(3-phenylmethoxyphenoxy)methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound C(C1=CC=CC=C1)OC=1C=C(OCC2=CC=C(CN3[C@H](CCC3)CO)C=C2)C=CC=1 SPXSEZMVRJLHQG-XMMPIXPASA-N 0.000 description 1
IOSLINNLJFQMFF-XMMPIXPASA-N [(2R)-1-[[4-[[3-[(4-fluorophenyl)methylsulfanyl]phenoxy]methyl]phenyl]methyl]pyrrolidin-2-yl]methanol Chemical compound FC1=CC=C(CSC=2C=C(OCC3=CC=C(CN4[C@H](CCC4)CO)C=C3)C=CC=2)C=C1 IOSLINNLJFQMFF-XMMPIXPASA-N 0.000 description 1
LNUFLCYMSVYYNW-ZPJMAFJPSA-N [(2r,3r,4s,5r,6r)-2-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[(2r,3r,4s,5r,6r)-6-[[(3s,5s,8r,9s,10s,13r,14s,17r)-10,13-dimethyl-17-[(2r)-6-methylheptan-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-disulfo Chemical compound O([C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1[C@@H](COS(O)(=O)=O)O[C@H]([C@@H]([C@H]1OS(O)(=O)=O)OS(O)(=O)=O)O[C@@H]1C[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@@]2(C)CC1)C)[C@H](C)CCCC(C)C)[C@H]1O[C@H](COS(O)(=O)=O)[C@@H](OS(O)(=O)=O)[C@H](OS(O)(=O)=O)[C@H]1OS(O)(=O)=O LNUFLCYMSVYYNW-ZPJMAFJPSA-N 0.000 description 1
LDQNYHNPPYYEBF-PELKAZGASA-N [(3R,4R)-1-(3-amino-1-cyclopropyl-6-fluoro-8-methoxy-2,4-dioxoquinazolin-7-yl)-4-fluoropyrrolidin-3-yl]methylcarbamic acid Chemical compound NN1C(N(C2=C(C(=C(C=C2C1=O)F)N1C[C@H]([C@H](C1)F)CNC(O)=O)OC)C1CC1)=O LDQNYHNPPYYEBF-PELKAZGASA-N 0.000 description 1
PSLUFJFHTBIXMW-WYEYVKMPSA-N [(3r,4ar,5s,6s,6as,10s,10ar,10bs)-3-ethenyl-10,10b-dihydroxy-3,4a,7,7,10a-pentamethyl-1-oxo-6-(2-pyridin-2-ylethylcarbamoyloxy)-5,6,6a,8,9,10-hexahydro-2h-benzo[f]chromen-5-yl] acetate Chemical compound O([C@@H]1[C@@H]([C@]2(O[C@](C)(CC(=O)[C@]2(O)[C@@]2(C)[C@@H](O)CCC(C)(C)[C@@H]21)C=C)C)OC(=O)C)C(=O)NCCC1=CC=CC=N1 PSLUFJFHTBIXMW-WYEYVKMPSA-N 0.000 description 1
CYLQMANYNUPGOT-RFZPGFLSSA-N [(3s,4r)-4-methylpyrrolidin-3-yl]carbamic acid Chemical compound C[C@@H]1CNC[C@H]1NC(O)=O CYLQMANYNUPGOT-RFZPGFLSSA-N 0.000 description 1
ROMCPZBDSSQINP-UHFFFAOYSA-N [1-cyclopropyl-6-fluoro-8-methoxy-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound FC1=CC(C(N(NC(O)=O)C(=O)N2C3CC3)=O)=C2C(OC)=C1N1CCC(NC(=O)OC(C)(C)C)C1 ROMCPZBDSSQINP-UHFFFAOYSA-N 0.000 description 1
MOBFEDDRGRRCIU-UHFFFAOYSA-N [3-(aminomethyl)piperidin-1-yl]carbamic acid Chemical compound NCC1CCCN(NC(O)=O)C1 MOBFEDDRGRRCIU-UHFFFAOYSA-N 0.000 description 1
PCLHRTFHZMANIS-UHFFFAOYSA-N [3-(methoxymethyl)pyrrolidin-3-yl]methylcarbamic acid Chemical compound OC(=O)NCC1(COC)CCNC1 PCLHRTFHZMANIS-UHFFFAOYSA-N 0.000 description 1
QUEVIVYUBTVRGB-UHFFFAOYSA-N [3-[(2,2,2-trifluoroethylamino)methyl]pyrrolidin-1-yl]carbamic acid Chemical class OC(=O)NN1CCC(CNCC(F)(F)F)C1 QUEVIVYUBTVRGB-UHFFFAOYSA-N 0.000 description 1
AWLXQBINBITCRP-UHFFFAOYSA-N [4-(trifluoromethyl)pyrrolidin-3-yl]methanamine Chemical compound NCC1CNCC1C(F)(F)F AWLXQBINBITCRP-UHFFFAOYSA-N 0.000 description 1
PFISKUIPLMYHCF-UHFFFAOYSA-N [6-chloro-1-cyclopropyl-8-fluoro-7-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(NC(=O)OC(C)(C)C)CCN1C1=C(Cl)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1F PFISKUIPLMYHCF-UHFFFAOYSA-N 0.000 description 1
HCJNFATUIPOXFM-UHFFFAOYSA-N [8-chloro-1-cyclopropyl-6-fluoro-7-[3-methyl-3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]-2,4-dioxoquinazolin-3-yl]carbamic acid Chemical compound C1C(CNC(=O)OC(C)(C)C)(C)CCN1C1=C(F)C=C2C(=O)N(NC(O)=O)C(=O)N(C3CC3)C2=C1Cl HCJNFATUIPOXFM-UHFFFAOYSA-N 0.000 description 1
DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 description 1
SMNRFWMNPDABKZ-WVALLCKVSA-N [[(2R,3S,4R,5S)-5-(2,6-dioxo-3H-pyridin-3-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2R,3S,4S,5R,6R)-4-fluoro-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound OC[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2C=CC(=O)NC2=O)[C@H](O)[C@@H](F)[C@@H]1O SMNRFWMNPDABKZ-WVALLCKVSA-N 0.000 description 1
WREOTYWODABZMH-DTZQCDIJSA-N [[(2r,3s,4r,5r)-3,4-dihydroxy-5-[2-oxo-4-(2-phenylethoxyamino)pyrimidin-1-yl]oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O[C@@H]1[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O[C@H]1N(C=C\1)C(=O)NC/1=N\OCCC1=CC=CC=C1 WREOTYWODABZMH-DTZQCDIJSA-N 0.000 description 1
WUDOTHFYIOUGMT-UHFFFAOYSA-N [[2-(cyclopropylamino)-4,5-difluorobenzoyl]amino]carbamic acid Chemical compound C1(CC1)NC1=C(C(=O)NNC(=O)O)C=C(C(=C1)F)F WUDOTHFYIOUGMT-UHFFFAOYSA-N 0.000 description 1
GHVFSTHQAZBDGQ-QGZVFWFLSA-N [[2-(cyclopropylamino)-5-fluoro-4-[(7s)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]benzoyl]amino]carbamic acid Chemical compound C([C@H]1NC(=O)OC(C)(C)C)N(C=2C(=CC(=C(NC3CC3)C=2)C(=O)NNC(O)=O)F)CC11CC1 GHVFSTHQAZBDGQ-QGZVFWFLSA-N 0.000 description 1
QQIRAVWVGBTHMJ-UHFFFAOYSA-N [dimethyl-(trimethylsilylamino)silyl]methane;lithium Chemical compound [Li].C[Si](C)(C)N[Si](C)(C)C QQIRAVWVGBTHMJ-UHFFFAOYSA-N 0.000 description 1
239000000370 acceptor Substances 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000004913 activation Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
150000001298 alcohols Chemical group 0.000 description 1
QBYJBZPUGVGKQQ-SJJAEHHWSA-N aldrin Chemical compound C1[C@H]2C=C[C@@H]1[C@H]1[C@@](C3(Cl)Cl)(Cl)C(Cl)=C(Cl)[C@@]3(Cl)[C@H]12 QBYJBZPUGVGKQQ-SJJAEHHWSA-N 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005262 alkoxyamine group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000003282 alkyl amino group Chemical group 0.000 description 1
125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
235000001014 amino acid Nutrition 0.000 description 1
150000001414 amino alcohols Chemical class 0.000 description 1
UFWCPDSEOVJAEA-UHFFFAOYSA-N amino-[3-chloro-2-(cyclopropylamino)-4,5-difluorobenzoyl]carbamic acid Chemical compound OC(=O)N(N)C(=O)C1=CC(F)=C(F)C(Cl)=C1NC1CC1 UFWCPDSEOVJAEA-UHFFFAOYSA-N 0.000 description 1
229960004050 aminobenzoic acid Drugs 0.000 description 1
150000005415 aminobenzoic acids Chemical class 0.000 description 1
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
159000000032 aromatic acids Chemical class 0.000 description 1
150000004982 aromatic amines Chemical class 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
125000001769 aryl amino group Chemical group 0.000 description 1
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
XRWSZZJLZRKHHD-WVWIJVSJSA-N asunaprevir Chemical compound O=C([C@@H]1C[C@H](CN1C(=O)[C@@H](NC(=O)OC(C)(C)C)C(C)(C)C)OC1=NC=C(C2=CC=C(Cl)C=C21)OC)N[C@]1(C(=O)NS(=O)(=O)C2CC2)C[C@H]1C=C XRWSZZJLZRKHHD-WVWIJVSJSA-N 0.000 description 1
DLGYNVMUCSTYDQ-UHFFFAOYSA-N azane;pyridine Chemical compound N.C1=CC=NC=C1 DLGYNVMUCSTYDQ-UHFFFAOYSA-N 0.000 description 1
VMAXJDJIFGIBGH-UHFFFAOYSA-N azetidin-3-ylmethanamine Chemical compound NCC1CNC1 VMAXJDJIFGIBGH-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
WLPUFAZAMBXLPF-UHFFFAOYSA-N benzyl 2,3,4,5,6-pentafluorobenzoate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1C(=O)OCC1=CC=CC=C1 WLPUFAZAMBXLPF-UHFFFAOYSA-N 0.000 description 1
235000019445 benzyl alcohol Nutrition 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
150000003939 benzylamines Chemical class 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000002619 bicyclic group Chemical group 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
RUEKPBLTWGFBOD-UHFFFAOYSA-N bromoethyne Chemical group BrC#C RUEKPBLTWGFBOD-UHFFFAOYSA-N 0.000 description 1
AEILLAXRDHDKDY-UHFFFAOYSA-N bromomethylcyclopropane Chemical compound BrCC1CC1 AEILLAXRDHDKDY-UHFFFAOYSA-N 0.000 description 1
239000010974 bronze Substances 0.000 description 1
ILAJWURWJKXJPW-UHFFFAOYSA-N butanedioic acid;octanedioic acid Chemical class OC(=O)CCC(O)=O.OC(=O)CCCCCCC(O)=O ILAJWURWJKXJPW-UHFFFAOYSA-N 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
239000000292 calcium oxide Substances 0.000 description 1
ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
VBOOQHDNDZGGHE-BAUSSPIASA-N carbamic acid (3S,4R)-4-phenylpyrrolidin-3-amine Chemical compound C(N)(O)=O.C1(=CC=CC=C1)[C@H]1[C@@H](CNC1)N VBOOQHDNDZGGHE-BAUSSPIASA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001717 carbocyclic compounds Chemical class 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
VDANGULDQQJODZ-UHFFFAOYSA-N chloroprocaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1Cl VDANGULDQQJODZ-UHFFFAOYSA-N 0.000 description 1
229960002023 chloroprocaine Drugs 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
229960001231 choline Drugs 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125797 compound 12 Drugs 0.000 description 1
229940126543 compound 14 Drugs 0.000 description 1
229940125758 compound 15 Drugs 0.000 description 1
229940126142 compound 16 Drugs 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
229940125810 compound 20 Drugs 0.000 description 1
229940126086 compound 21 Drugs 0.000 description 1
229940126208 compound 22 Drugs 0.000 description 1
229940125833 compound 23 Drugs 0.000 description 1
229940125961 compound 24 Drugs 0.000 description 1
229940125846 compound 25 Drugs 0.000 description 1
229940125851 compound 27 Drugs 0.000 description 1
229940127204 compound 29 Drugs 0.000 description 1
229940126214 compound 3 Drugs 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
229940125878 compound 36 Drugs 0.000 description 1
229940125807 compound 37 Drugs 0.000 description 1
229940127573 compound 38 Drugs 0.000 description 1
229940126540 compound 41 Drugs 0.000 description 1
229940125936 compound 42 Drugs 0.000 description 1
229940125844 compound 46 Drugs 0.000 description 1
229940127271 compound 49 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
229940126545 compound 53 Drugs 0.000 description 1
229940125900 compound 59 Drugs 0.000 description 1
229940126179 compound 72 Drugs 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 1
NWFNSTOSIVLCJA-UHFFFAOYSA-L copper;diacetate;hydrate Chemical compound O.[Cu+2].CC([O-])=O.CC([O-])=O NWFNSTOSIVLCJA-UHFFFAOYSA-L 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000004855 decalinyl group Chemical group C1(CCCC2CCCCC12)* 0.000 description 1
238000005695 dehalogenation reaction Methods 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
238000011161 development Methods 0.000 description 1
238000006193 diazotization reaction Methods 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
229940043237 diethanolamine Drugs 0.000 description 1
125000006371 dihalo methyl group Chemical group 0.000 description 1
229940043279 diisopropylamine Drugs 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000002934 diuretic Substances 0.000 description 1
230000001882 diuretic effect Effects 0.000 description 1
125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012039 electrophile Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
238000010828 elution Methods 0.000 description 1
BJXYHBKEQFQVES-NWDGAFQWSA-N enpatoran Chemical compound N[C@H]1CN(C[C@H](C1)C(F)(F)F)C1=C2C=CC=NC2=C(C=C1)C#N BJXYHBKEQFQVES-NWDGAFQWSA-N 0.000 description 1
125000004185 ester group Chemical group 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
239000004210 ether based solvent Substances 0.000 description 1
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
VFRSADQPWYCXDG-LEUCUCNGSA-N ethyl (2s,5s)-5-methylpyrrolidine-2-carboxylate;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CCOC(=O)[C@@H]1CC[C@H](C)N1 VFRSADQPWYCXDG-LEUCUCNGSA-N 0.000 description 1
XTMYIEIMUNPCAN-UHFFFAOYSA-N ethyl 2,3,4-trifluoro-5-methoxybenzoate Chemical compound CCOC(=O)C1=CC(OC)=C(F)C(F)=C1F XTMYIEIMUNPCAN-UHFFFAOYSA-N 0.000 description 1
BWNOFHKEKFPTBV-JTQLQIEISA-N ethyl 2,3,6-trifluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=C(F)C=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 BWNOFHKEKFPTBV-JTQLQIEISA-N 0.000 description 1
DWRVQRRMMIQTBY-UHFFFAOYSA-N ethyl 2,3-difluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC(OC)=C1N1CC(NC(=O)OC(C)(C)C)CC1 DWRVQRRMMIQTBY-UHFFFAOYSA-N 0.000 description 1
IDCQRHBVSOPQSN-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-(phenylmethoxyiminomethyl)benzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(C=NOCC=2C=CC=CC=2)=C1F IDCQRHBVSOPQSN-UHFFFAOYSA-N 0.000 description 1
CNLWICAPVKYJDJ-UHFFFAOYSA-N ethyl 2,4,5-trifluoro-3-methylbenzoate Chemical compound CCOC(=O)C1=CC(F)=C(F)C(C)=C1F CNLWICAPVKYJDJ-UHFFFAOYSA-N 0.000 description 1
DXEDQZQUGXXWSF-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methoxy-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(CNC(=O)OC(C)(C)C)CC1 DXEDQZQUGXXWSF-UHFFFAOYSA-N 0.000 description 1
USTAENCAYUNVTB-UHFFFAOYSA-N ethyl 2,5-difluoro-3-methyl-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 USTAENCAYUNVTB-UHFFFAOYSA-N 0.000 description 1
GTHZCGNEWNJQJS-UHFFFAOYSA-N ethyl 2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-3-(phenylmethoxyiminomethyl)benzoate Chemical compound C=1C=CC=CC=1CON=CC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 GTHZCGNEWNJQJS-UHFFFAOYSA-N 0.000 description 1
DOKPAMDPONKHKL-KZUDCZAMSA-N ethyl 2-(butan-2-ylamino)-3-chloro-5-fluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(NC(C)CC)C(C(=O)OCC)=CC(F)=C1N1C[C@@H](NC(=O)OC(C)(C)C)CC1 DOKPAMDPONKHKL-KZUDCZAMSA-N 0.000 description 1
YXDJQYZWVRALDE-UHFFFAOYSA-N ethyl 2-(cyclobutylamino)-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CCOC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C=C1NC1CCC1 YXDJQYZWVRALDE-UHFFFAOYSA-N 0.000 description 1
MGPLAEBQINWPMD-ZDUSSCGKSA-N ethyl 2-(cyclopropylamino)-3,5-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 MGPLAEBQINWPMD-ZDUSSCGKSA-N 0.000 description 1
NSABSAJYHZYYMK-ZDUSSCGKSA-N ethyl 2-(cyclopropylamino)-3,6-difluoro-4-[(3s)-3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=C(F)C=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 NSABSAJYHZYYMK-ZDUSSCGKSA-N 0.000 description 1
RCSVXGMSCAHJGY-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-3-ethoxy-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CCOC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 RCSVXGMSCAHJGY-UHFFFAOYSA-N 0.000 description 1
XWDXQVZBNAZYEW-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-3-fluoro-5-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(NC2CC2)C(C(=O)OCC)=CC(OC)=C1N1CCC(NC(=O)OC(C)(C)C)C1 XWDXQVZBNAZYEW-UHFFFAOYSA-N 0.000 description 1
OTDZYMWFJNREHP-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-3-methoxy-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound COC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 OTDZYMWFJNREHP-UHFFFAOYSA-N 0.000 description 1
RJJPONQZMPHMAC-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-3-methyl-4-[3-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]pyrrolidin-1-yl]benzoate Chemical compound CC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(CNC(=O)OC(C)(C)C)C1 RJJPONQZMPHMAC-UHFFFAOYSA-N 0.000 description 1
JUPGNVIZIUFIDH-UHFFFAOYSA-N ethyl 2-(cyclopropylamino)-5-fluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]-3-(phenylmethoxyiminomethyl)benzoate Chemical compound C=1C=CC=CC=1CON=CC1=C(NC2CC2)C(C(=O)OCC)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 JUPGNVIZIUFIDH-UHFFFAOYSA-N 0.000 description 1
KOWLMUHLYWGECF-UHFFFAOYSA-N ethyl 2-chloro-5-fluoro-6-methylsulfanylpyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC(F)=C(SC)N=C1Cl KOWLMUHLYWGECF-UHFFFAOYSA-N 0.000 description 1
CINXGNHRKLMYRK-UHFFFAOYSA-N ethyl 2-cyclopropylideneacetate Chemical compound CCOC(=O)C=C1CC1 CINXGNHRKLMYRK-UHFFFAOYSA-N 0.000 description 1
GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
XITYZNUXHDHZKA-UHFFFAOYSA-N ethyl 3-chloro-2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound ClC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 XITYZNUXHDHZKA-UHFFFAOYSA-N 0.000 description 1
NXCURRNUONQADF-UHFFFAOYSA-N ethyl 3-ethoxy-2,5-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound CCOC1=C(F)C(C(=O)OCC)=CC(F)=C1N1CC(NC(=O)OC(C)(C)C)CC1 NXCURRNUONQADF-UHFFFAOYSA-N 0.000 description 1
FCWLRKKKNGDVQE-UHFFFAOYSA-N ethyl 5-benzyl-5-azaspiro[2.4]heptane-2-carboxylate Chemical compound CCOC(=O)C1CC11CN(CC=2C=CC=CC=2)CC1 FCWLRKKKNGDVQE-UHFFFAOYSA-N 0.000 description 1
JEZLFPHQDRWQJL-UHFFFAOYSA-N ethyl 5-benzyl-5-azaspiro[2.4]heptane-7-carboxylate Chemical compound C1C2(CC2)C(C(=O)OCC)CN1CC1=CC=CC=C1 JEZLFPHQDRWQJL-UHFFFAOYSA-N 0.000 description 1
ILCZUEOFLWBQFZ-UHFFFAOYSA-N ethyl 5-chloro-2,3-difluoro-4-[3-[(2-methylpropan-2-yl)oxycarbonylamino]pyrrolidin-1-yl]benzoate Chemical compound FC1=C(F)C(C(=O)OCC)=CC(Cl)=C1N1CC(NC(=O)OC(C)(C)C)CC1 ILCZUEOFLWBQFZ-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
125000006419 fluorocyclopropyl group Chemical group 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011491 glass wool Substances 0.000 description 1
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
230000003993 interaction Effects 0.000 description 1
239000011630 iodine Substances 0.000 description 1
VLODBNNWEWTQJX-UHFFFAOYSA-N iodocyclopropane Chemical compound IC1CC1 VLODBNNWEWTQJX-UHFFFAOYSA-N 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical class CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
NIZHERJWXFHGGU-UHFFFAOYSA-N isocyanato(trimethyl)silane Chemical compound C[Si](C)(C)N=C=O NIZHERJWXFHGGU-UHFFFAOYSA-N 0.000 description 1
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical group C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 1
150000003854 isothiazoles Chemical class 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
150000003893 lactate salts Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002688 maleic acid derivatives Chemical class 0.000 description 1
150000002690 malonic acid derivatives Chemical class 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
239000000155 melt Substances 0.000 description 1
125000005341 metaphosphate group Chemical group 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
YTLNZVFTBFLYEL-UHFFFAOYSA-N methyl 2-(cyclopropylamino)-4,5-difluorobenzoate Chemical compound COC(=O)C1=CC(F)=C(F)C=C1NC1CC1 YTLNZVFTBFLYEL-UHFFFAOYSA-N 0.000 description 1
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical class COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
230000011987 methylation Effects 0.000 description 1
238000007069 methylation reaction Methods 0.000 description 1
230000003278 mimic effect Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
PWBJWDKDPAPGED-UHFFFAOYSA-N n'-chlorobutanediamide Chemical compound NC(=O)CCC(=O)NCl PWBJWDKDPAPGED-UHFFFAOYSA-N 0.000 description 1
HYGXISCUUFVGQW-UHFFFAOYSA-N n,n-dimethylformamide;1,4-dioxane Chemical compound CN(C)C=O.C1COCCO1 HYGXISCUUFVGQW-UHFFFAOYSA-N 0.000 description 1
RPZAAFUKDPKTKP-UHFFFAOYSA-N n-(methoxymethyl)-1-phenyl-n-(trimethylsilylmethyl)methanamine Chemical compound COCN(C[Si](C)(C)C)CC1=CC=CC=C1 RPZAAFUKDPKTKP-UHFFFAOYSA-N 0.000 description 1
VBBUFMFZDHLELS-UHFFFAOYSA-N n-(oxomethylidene)carbamoyl chloride Chemical compound ClC(=O)N=C=O VBBUFMFZDHLELS-UHFFFAOYSA-N 0.000 description 1
YXLVSYUUZGMLFZ-UHFFFAOYSA-N n-[1-(1-benzyl-4-methylpyrrolidin-3-yl)ethylidene]hydroxylamine Chemical compound C1C(C(C)=NO)C(C)CN1CC1=CC=CC=C1 YXLVSYUUZGMLFZ-UHFFFAOYSA-N 0.000 description 1
IWYPOHZPEFBLBA-UHFFFAOYSA-N n-[1-(1-benzylpiperidin-3-yl)ethylidene]hydroxylamine Chemical compound C1C(C(=NO)C)CCCN1CC1=CC=CC=C1 IWYPOHZPEFBLBA-UHFFFAOYSA-N 0.000 description 1
YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
HYQPGGVTLYKWFG-UHFFFAOYSA-N n-[[1-(3-amino-8-chloro-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]methyl]methanesulfonamide;hydrochloride Chemical compound Cl.C1C(CNS(=O)(=O)C)CCN1C1=C(F)C=C2C(=O)N(N)C(=O)N(C3CC3)C2=C1Cl HYQPGGVTLYKWFG-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
NGZYRKGJWYJGRS-UHFFFAOYSA-N n-methylpyrrolidin-3-amine Chemical compound CNC1CCNC1 NGZYRKGJWYJGRS-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
XBXCNNQPRYLIDE-UHFFFAOYSA-M n-tert-butylcarbamate Chemical compound CC(C)(C)NC([O-])=O XBXCNNQPRYLIDE-UHFFFAOYSA-M 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
BVOCPVIXARZNQN-UHFFFAOYSA-N nipecotamide Chemical compound NC(=O)C1CCCNC1 BVOCPVIXARZNQN-UHFFFAOYSA-N 0.000 description 1
XJLSEXAGTJCILF-UHFFFAOYSA-N nipecotic acid Chemical compound OC(=O)C1CCCNC1 XJLSEXAGTJCILF-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
YLACRFYIUQZNIV-UHFFFAOYSA-N o-(2,4-dinitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O YLACRFYIUQZNIV-UHFFFAOYSA-N 0.000 description 1
HYDZPXNVHXJHBG-UHFFFAOYSA-N o-benzylhydroxylamine;hydron;chloride Chemical compound Cl.NOCC1=CC=CC=C1 HYDZPXNVHXJHBG-UHFFFAOYSA-N 0.000 description 1
WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical class CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000003891 oxalate salts Chemical class 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
LXNAVEXFUKBNMK-UHFFFAOYSA-N palladium(II) acetate Substances [Pd].CC(O)=O.CC(O)=O LXNAVEXFUKBNMK-UHFFFAOYSA-N 0.000 description 1
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical compound [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
102000020233 phosphotransferase Human genes 0.000 description 1
125000005498 phthalate group Chemical class 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 description 1
LTEKQAPRXFBRNN-UHFFFAOYSA-N piperidin-4-ylmethanamine Chemical compound NCC1CCNCC1 LTEKQAPRXFBRNN-UHFFFAOYSA-N 0.000 description 1
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
125000003367 polycyclic group Chemical group 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000002243 precursor Substances 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
230000008569 process Effects 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical group C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 description 1
125000004940 pyridazin-4-yl group Chemical group N1=NC=C(C=C1)* 0.000 description 1
125000004941 pyridazin-5-yl group Chemical group N1=NC=CC(=C1)* 0.000 description 1
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 description 1
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical group NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 description 1
QOTUIIJRVXKSJU-UHFFFAOYSA-N pyrrolidin-3-ylmethanol Chemical compound OCC1CCNC1 QOTUIIJRVXKSJU-UHFFFAOYSA-N 0.000 description 1
XSUHSSTUTHPGDQ-UHFFFAOYSA-N pyrrolidin-3-ylmethylcarbamic acid Chemical compound OC(=O)NCC1CCNC1 XSUHSSTUTHPGDQ-UHFFFAOYSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000006722 reduction reaction Methods 0.000 description 1
125000006413 ring segment Chemical group 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
150000003333 secondary alcohols Chemical class 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
KSAVQLQVUXSOCR-UHFFFAOYSA-M sodium lauroyl sarcosinate Chemical compound [Na+].CCCCCCCCCCCC(=O)N(C)CC([O-])=O KSAVQLQVUXSOCR-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
RSIJVJUOQBWMIM-UHFFFAOYSA-L sodium sulfate decahydrate Chemical compound O.O.O.O.O.O.O.O.O.O.[Na+].[Na+].[O-]S([O-])(=O)=O RSIJVJUOQBWMIM-UHFFFAOYSA-L 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
150000003457 sulfones Chemical group 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
206010042772 syncope Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical group CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
HOLFKYFPAJFTQK-UHFFFAOYSA-N tert-butyl n-(1-piperidin-3-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1CCCNC1 HOLFKYFPAJFTQK-UHFFFAOYSA-N 0.000 description 1
OWGYHEOEGOLPEK-UHFFFAOYSA-N tert-butyl n-(2-pyrrolidin-3-ylethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCC1CCNC1 OWGYHEOEGOLPEK-UHFFFAOYSA-N 0.000 description 1
QIYOMZXJQAKHEK-UHFFFAOYSA-N tert-butyl n-(3-azabicyclo[3.1.0]hexan-6-yl)carbamate Chemical compound C1NCC2C(NC(=O)OC(C)(C)C)C21 QIYOMZXJQAKHEK-UHFFFAOYSA-N 0.000 description 1
DIQWSFWWYVRXRO-UHFFFAOYSA-N tert-butyl n-(3-methylpyrrolidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)NC1(C)CCNC1 DIQWSFWWYVRXRO-UHFFFAOYSA-N 0.000 description 1
HOVWKJWUCRVIBO-UHFFFAOYSA-N tert-butyl n-(5-azaspiro[2.4]heptan-7-ylmethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCC1CNCC11CC1 HOVWKJWUCRVIBO-UHFFFAOYSA-N 0.000 description 1
VRLMNTJDNRPIFB-UHFFFAOYSA-N tert-butyl n-[(3-benzylpyrrolidin-3-yl)methyl]carbamate Chemical compound C=1C=CC=CC=1CC1(CNC(=O)OC(C)(C)C)CCNC1 VRLMNTJDNRPIFB-UHFFFAOYSA-N 0.000 description 1
AXCFIJFQUMHJRG-UHFFFAOYSA-N tert-butyl n-[(3-methylpyrrolidin-3-yl)methyl]carbamate Chemical compound CC(C)(C)OC(=O)NCC1(C)CCNC1 AXCFIJFQUMHJRG-UHFFFAOYSA-N 0.000 description 1
OTEUFMMUHJTHRF-NSHDSACASA-N tert-butyl n-[(3s)-1-(3-amino-1-cyclopropyl-6-fluoro-2,4-dioxoquinazolin-7-yl)pyrrolidin-3-yl]carbamate Chemical compound C1[C@@H](NC(=O)OC(C)(C)C)CCN1C(C(=C1)F)=CC2=C1C(=O)N(N)C(=O)N2C1CC1 OTEUFMMUHJTHRF-NSHDSACASA-N 0.000 description 1
JNSQOXAPISKZGT-AWEZNQCLSA-N tert-butyl n-[(3s)-1-[2-chloro-3-(cyclopropylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound ClC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CC[C@H](NC(=O)OC(C)(C)C)C1 JNSQOXAPISKZGT-AWEZNQCLSA-N 0.000 description 1
FQYOOTTXAJMDLQ-INIZCTEOSA-N tert-butyl n-[(3s)-1-[5-(2,4-difluoroanilino)-2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2C[C@H](CC2)NC(=O)OC(C)(C)C)C=C1NC1=CC=C(F)C=C1F FQYOOTTXAJMDLQ-INIZCTEOSA-N 0.000 description 1
GYGICGXBPFNMBP-INIZCTEOSA-N tert-butyl n-[(3s)-1-[5-(cyclopropylamino)-2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]-n-methylcarbamate Chemical compound C1[C@@H](N(C)C(=O)OC(C)(C)C)CCN1C1=CC(NC2CC2)=C(C(=O)NNC(=O)OC(C)(C)C)C=C1F GYGICGXBPFNMBP-INIZCTEOSA-N 0.000 description 1
YAVJOOLTQLKNGR-UHFFFAOYSA-N tert-butyl n-[1-(3-methoxypyrrolidin-3-yl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1(OC)CCNC1 YAVJOOLTQLKNGR-UHFFFAOYSA-N 0.000 description 1
TZPZNQJXNYELQK-UHFFFAOYSA-N tert-butyl n-[1-(5-azaspiro[2.4]heptan-7-yl)ethyl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)C1CNCC11CC1 TZPZNQJXNYELQK-UHFFFAOYSA-N 0.000 description 1
JJJDLYOZIBFYDH-UHFFFAOYSA-N tert-butyl n-[1-(5-benzyl-5-azaspiro[2.4]heptan-7-yl)ethyl]carbamate Chemical compound C1C2(CC2)C(C(NC(=O)OC(C)(C)C)C)CN1CC1=CC=CC=C1 JJJDLYOZIBFYDH-UHFFFAOYSA-N 0.000 description 1
QLXICPNSUOQISE-UHFFFAOYSA-N tert-butyl n-[1-[2-chloro-3-(cyclobutylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound ClC1=C(NC2CCC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 QLXICPNSUOQISE-UHFFFAOYSA-N 0.000 description 1
JZUFJGCCTLZSFE-UHFFFAOYSA-N tert-butyl n-[1-[3-(butan-2-ylamino)-2-chloro-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound C1=C(C(=O)NNC(=O)OC(C)(C)C)C(NC(C)CC)=C(Cl)C(N2CC(CC2)NC(=O)OC(C)(C)C)=C1F JZUFJGCCTLZSFE-UHFFFAOYSA-N 0.000 description 1
DBZPVFMDQGPXNE-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-2-ethoxy-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OCC)=C1NC1CC1 DBZPVFMDQGPXNE-UHFFFAOYSA-N 0.000 description 1
LBCZMSJBRAAFAB-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-2-fluoro-6-methoxy-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound FC1=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(OC)=CC(C(=O)NNC(=O)OC(C)(C)C)=C1NC1CC1 LBCZMSJBRAAFAB-UHFFFAOYSA-N 0.000 description 1
DPVSJMYBIRCSCJ-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-6-fluoro-2-methyl-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C(C)=C1NC1CC1 DPVSJMYBIRCSCJ-UHFFFAOYSA-N 0.000 description 1
WZDRADUYGSTDHX-UHFFFAOYSA-N tert-butyl n-[1-[3-(cyclopropylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]-2-(phenylmethoxyiminomethyl)phenyl]pyrrolidin-3-yl]carbamate Chemical compound C=1C=CC=CC=1CON=CC1=C(NC2CC2)C(C(=O)NNC(=O)OC(C)(C)C)=CC(F)=C1N1CCC(NC(=O)OC(C)(C)C)C1 WZDRADUYGSTDHX-UHFFFAOYSA-N 0.000 description 1
AFMAMAZBTWCOOI-UHFFFAOYSA-N tert-butyl n-[1-[5-(cyclobutylamino)-2-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC(CC2)NC(=O)OC(C)(C)C)C=C1NC1CCC1 AFMAMAZBTWCOOI-UHFFFAOYSA-N 0.000 description 1
MNIHYAVDKLMINM-SECBINFHSA-N tert-butyl n-[2-[(3r)-pyrrolidin-3-yl]propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)[C@@H]1CCNC1 MNIHYAVDKLMINM-SECBINFHSA-N 0.000 description 1
MNIHYAVDKLMINM-VIFPVBQESA-N tert-butyl n-[2-[(3s)-pyrrolidin-3-yl]propan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)NC(C)(C)[C@H]1CCNC1 MNIHYAVDKLMINM-VIFPVBQESA-N 0.000 description 1
GWYXCNXINAWWBV-JGVFFNPUSA-N tert-butyl n-[[(3s,4s)-4-(trifluoromethyl)pyrrolidin-3-yl]methyl]carbamate Chemical compound CC(C)(C)OC(=O)NC[C@@H]1CNC[C@H]1C(F)(F)F GWYXCNXINAWWBV-JGVFFNPUSA-N 0.000 description 1
XAQBCOMOVGTDFS-UHFFFAOYSA-N tert-butyl n-[[1-[2-chloro-3-(cyclopropylamino)-6-fluoro-4-[[(2-methylpropan-2-yl)oxycarbonylamino]carbamoyl]phenyl]pyrrolidin-3-yl]methyl]carbamate Chemical compound C1C(CNC(=O)OC(C)(C)C)CCN1C1=C(F)C=C(C(=O)NNC(=O)OC(C)(C)C)C(NC2CC2)=C1Cl XAQBCOMOVGTDFS-UHFFFAOYSA-N 0.000 description 1
DZSMPAMHLLIGCE-HXUWFJFHSA-N tert-butyl n-[[2-(cyclopropylamino)-5-fluoro-4-[(7s)-7-[(2-methylpropan-2-yl)oxycarbonylamino]-5-azaspiro[2.4]heptan-5-yl]benzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC3(CC3)[C@H](NC(=O)OC(C)(C)C)C2)C=C1NC1CC1 DZSMPAMHLLIGCE-HXUWFJFHSA-N 0.000 description 1
JMWMSTLGHHXNSR-UHFFFAOYSA-N tert-butyl n-[[2-(cyclopropylamino)-5-fluoro-4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-azabicyclo[3.1.0]hexan-3-yl]benzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC3C(C3NC(=O)OC(C)(C)C)C2)C=C1NC1CC1 JMWMSTLGHHXNSR-UHFFFAOYSA-N 0.000 description 1
YWYPFEUVPABOBS-UHFFFAOYSA-N tert-butyl n-[[2-(cyclopropylamino)-5-fluoro-4-pyrrolidin-1-ylbenzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CCCC2)C=C1NC1CC1 YWYPFEUVPABOBS-UHFFFAOYSA-N 0.000 description 1
RXNOKKHYLMUBQK-UHFFFAOYSA-N tert-butyl n-[[3-chloro-2-(cyclopropylamino)-5-fluoro-4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]-3-azabicyclo[3.1.0]hexan-3-yl]benzoyl]amino]carbamate Chemical compound CC(C)(C)OC(=O)NNC(=O)C1=CC(F)=C(N2CC3C(C3NC(=O)OC(C)(C)C)C2)C(Cl)=C1NC1CC1 RXNOKKHYLMUBQK-UHFFFAOYSA-N 0.000 description 1
LTEWWHZIIXPUBF-UHFFFAOYSA-N tert-butyl n-amino-n-[2-(2,4-difluoroanilino)-4,5-difluorobenzoyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC(F)=C(F)C=C1NC1=CC=C(F)C=C1F LTEWWHZIIXPUBF-UHFFFAOYSA-N 0.000 description 1
BSJLOBHRTVICMV-UHFFFAOYSA-N tert-butyl n-amino-n-[5-chloro-2-(cyclopropylamino)-4-fluorobenzoyl]carbamate Chemical compound CC(C)(C)OC(=O)N(N)C(=O)C1=CC(Cl)=C(F)C=C1NC1CC1 BSJLOBHRTVICMV-UHFFFAOYSA-N 0.000 description 1
RARMMJLRNFXCRR-UHFFFAOYSA-N tert-butyl n-ethyl-n-(4-fluoropyrrolidin-3-yl)carbamate Chemical compound CC(C)(C)OC(=O)N(CC)C1CNCC1F RARMMJLRNFXCRR-UHFFFAOYSA-N 0.000 description 1
XYKYUXYNQDXZTD-QMMMGPOBSA-N tert-butyl n-methyl-n-[(3s)-pyrrolidin-3-yl]carbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@H]1CCNC1 XYKYUXYNQDXZTD-QMMMGPOBSA-N 0.000 description 1
239000012414 tert-butyl nitrite Substances 0.000 description 1
CWXPZXBSDSIRCS-UHFFFAOYSA-N tert-butyl piperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCNCC1 CWXPZXBSDSIRCS-UHFFFAOYSA-N 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
150000003557 thiazoles Chemical class 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
125000005309 thioalkoxy group Chemical group 0.000 description 1
125000004568 thiomorpholinyl group Chemical group 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
238000001665 trituration Methods 0.000 description 1
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
AQLJVWUFPCUVLO-UHFFFAOYSA-N urea hydrogen peroxide Chemical compound OO.NC(N)=O AQLJVWUFPCUVLO-UHFFFAOYSA-N 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
- C07D239/96—Two oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/10—Spiro-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Virology (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Oncology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Paper (AREA)

HR20020696A 2000-01-24 2002-08-23 3-aminoquinazolin-2,4-dione antibakterial agents HRP20020696A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US17825200P	2000-01-24	2000-01-24
US24126700P	2000-10-18	2000-10-18

Publications (1)

Publication Number	Publication Date
HRP20020696A2 true HRP20020696A2 (en)	2003-12-31

Family

ID=26874138

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR20020696A HRP20020696A2 (en)	2000-01-24	2002-08-23	3-aminoquinazolin-2,4-dione antibakterial agents

Country Status (38)

Country	Link
US (2)	US7094780B1 (no)
EP (1)	EP1255739B1 (no)
JP (1)	JP4811978B2 (no)
KR (1)	KR20020067701A (no)
CN (1)	CN1425008A (no)
AP (1)	AP2002002603A0 (no)
AR (1)	AR030186A1 (no)
AT (1)	ATE398110T1 (no)
AU (1)	AU783078B2 (no)
BG (1)	BG107023A (no)
BR (1)	BR0017010A (no)
CA (1)	CA2393802C (no)
CO (1)	CO5320600A1 (no)
CR (1)	CR6709A (no)
DE (1)	DE60039194D1 (no)
EA (1)	EA005585B1 (no)
EE (1)	EE200200412A (no)
ES (1)	ES2304992T3 (no)
GE (1)	GEP20053429B (no)
HK (1)	HK1054237A1 (no)
HN (1)	HN2001000009A (no)
HR (1)	HRP20020696A2 (no)
HU (1)	HUP0204101A3 (no)
IL (1)	IL150393A0 (no)
IS (1)	IS6448A (no)
MA (1)	MA26866A1 (no)
MX (1)	MXPA02005989A (no)
NO (1)	NO20023516D0 (no)
OA (1)	OA12316A (no)
PA (1)	PA8510101A1 (no)
PE (1)	PE20011060A1 (no)
PL (1)	PL356837A1 (no)
SK (1)	SK10572002A3 (no)
SV (1)	SV2001000288A (no)
TN (1)	TNSN01011A1 (no)
UY (1)	UY26551A1 (no)
WO (1)	WO2001053273A1 (no)
YU (1)	YU55902A (no)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BR9812644B1 (pt)	1997-09-15	2010-07-13		quinolonas antimicrobianas, composição farmacêutica e uso das mesmas.
MXPA03010799A (es)	2001-05-30	2005-07-25	Warner Lambert Co	Agentes antibacterianos.
BR0210028A (pt) *	2001-06-19	2004-06-22	Warner Lambert Co	Agentes antibacterianos
US6900224B2 (en) *	2002-07-31	2005-05-31	The Procter & Gamble Company	Antimicrobial quinolones, their compositions and uses
WO2005026153A1 (en) *	2003-09-12	2005-03-24	Warner-Lambert Company Llc	Quinazoline-2, 4-diones as antibacterial agents
BRPI0414319A (pt) *	2003-09-12	2006-11-07	Warner Lambert Co	agentes antibacterianos de quinolona
JP2007511597A (ja) *	2003-11-18	2007-05-10	ワーナー−ランバートカンパニーリミテッドライアビリティーカンパニー	抗菌アミノキナゾリヂンヂオン誘導体
WO2006019965A2 (en) *	2004-07-16	2006-02-23	Takeda San Diego, Inc.	Dipeptidyl peptidase inhibitors
GB0416730D0 (en)	2004-07-27	2004-09-01	Novartis Ag	Organic compounds
ATE447572T1 (de) *	2005-01-26	2009-11-15	Hoffmann La Roche	Phenylmethanonderivate und ihre verwendung als glycin-transporter-1-hemmer
GB0507298D0 (en) *	2005-04-11	2005-05-18	Novartis Ag	Organic compounds
US7977346B2 (en)	2006-01-17	2011-07-12	Guoqing Paul Chen	Spiro compounds and methods of use
EP1999125A2 (en)	2006-03-28	2008-12-10	The Procter and Gamble Company	A coupling process for preparing quinolone intermediates
ATE507219T1 (de)	2006-03-28	2011-05-15	Warner Chilcott Co Llc	Malatsalze und polymorphe von (3s,5s)-7-ä3-amino- 5-methyl-piperidinylü-1-cyclopropyl-1,4-dihydro 8-methoxy-4-oxo-3-chinolincarbonsäure
US20080139574A1 (en)	2006-11-30	2008-06-12	Cadila Healthcare Limited	Novel quinoline derivatives
PL2239257T3 (pl) *	2008-01-30	2012-10-31	Shin Poong Pharmaceutical Co Ltd	Nowe pochodne chinazolino-2,4-dionu oraz zawierające je farmaceutyczne kompozycje do profilaktyki i leczenia chorób nerwów czaszkowych
WO2011031745A1 (en)	2009-09-09	2011-03-17	Achaogen, Inc.	Antibacterial fluoroquinolone analogs
WO2012088266A2 (en)	2010-12-22	2012-06-28	Incyte Corporation	Substituted imidazopyridazines and benzimidazoles as inhibitors of fgfr3
KR102132574B1 (ko)	2011-03-15	2020-07-09	로렌스 리버모어 내쇼날 시큐리티, 엘엘시	트라이사이클릭 자이라제 억제제
RS57621B1 (sr) *	2011-12-21	2018-11-30	Jiangsu Hengrui Medicine Co	Derivat šestočlanog heteroaril prstena pirola, postupak njegove pripreme i njegova medicinska upotreba
SG10201610416TA (en)	2012-06-13	2017-01-27	Incyte Corp	Substituted tricyclic compounds as fgfr inhibitors
WO2014026125A1 (en)	2012-08-10	2014-02-13	Incyte Corporation	Pyrazine derivatives as fgfr inhibitors
EP2895488A1 (en)	2012-09-12	2015-07-22	Trius Therapeutics, Inc.	Tricyclic gyrase inhibitors for use as antibacterial agents
US9266892B2 (en)	2012-12-19	2016-02-23	Incyte Holdings Corporation	Fused pyrazoles as FGFR inhibitors
SI2986610T1 (en)	2013-04-19	2018-04-30	Incyte Holdings Corporation	Bicyclic heterocycles as inhibitors of FGFR
US10851105B2 (en)	2014-10-22	2020-12-01	Incyte Corporation	Bicyclic heterocycles as FGFR4 inhibitors
MX2020004108A (es)	2015-02-20	2022-01-03	Incyte Corp	Heterociclos biciclicos como inhibidores de receptores del factor de crecimiento fibroblastico (fgfr).
MA41551A (fr)	2015-02-20	2017-12-26	Incyte Corp	Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4
WO2016134294A1 (en)	2015-02-20	2016-08-25	Incyte Corporation	Bicyclic heterocycles as fgfr4 inhibitors
CN108530448A (zh) *	2017-03-02	2018-09-14	浙江司太立制药股份有限公司	含有碱性氮杂螺环片段的苯并噻嗪-4-酮类化合物及其制备方法
AR111960A1 (es)	2017-05-26	2019-09-04	Incyte Corp	Formas cristalinas de un inhibidor de fgfr y procesos para su preparación
WO2019213544A2 (en)	2018-05-04	2019-11-07	Incyte Corporation	Solid forms of an fgfr inhibitor and processes for preparing the same
TW201946630A (zh)	2018-05-04	2019-12-16	美商英塞特公司	Fgfr抑制劑之鹽
CN111620866A (zh) *	2019-02-27	2020-09-04	南京药石科技股份有限公司	一种顺式-7,7-二氟-六氢-1H 吡咯并[3,4-c]吡啶衍生物及其制备方法
US11628162B2 (en)	2019-03-08	2023-04-18	Incyte Corporation	Methods of treating cancer with an FGFR inhibitor
WO2021007269A1 (en)	2019-07-09	2021-01-14	Incyte Corporation	Bicyclic heterocycles as fgfr inhibitors
IL291901A (en)	2019-10-14	2022-06-01	Incyte Corp	Bicyclyl heterocycles as fgr suppressors
US11566028B2 (en)	2019-10-16	2023-01-31	Incyte Corporation	Bicyclic heterocycles as FGFR inhibitors
WO2021113462A1 (en)	2019-12-04	2021-06-10	Incyte Corporation	Derivatives of an fgfr inhibitor
EP4069696A1 (en)	2019-12-04	2022-10-12	Incyte Corporation	Tricyclic heterocycles as fgfr inhibitors
CN111499513B (zh) *	2020-04-24	2023-03-14	上海毕得医药科技股份有限公司	一种2,3,4,5-四溴苯甲酸酯的合成方法
US11939331B2 (en)	2021-06-09	2024-03-26	Incyte Corporation	Tricyclic heterocycles as FGFR inhibitors

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1068263B (no) *		1959-11-05
NL80851C (no) *	1958-02-25	1956-03-15
ATE8626T1 (de)	1980-03-10	1984-08-15	Berri-Balzac Societe Dite:	3-amino-(1h,3h)-2,4-chinazolindionderivate.
GB2097784A (en)	1981-04-28	1982-11-10	Davidson Dr John Stirton	Dihydrobenzotriazepine diones; aminoquinazoline diones
AU5813394A (en)	1992-12-23	1994-07-19	Byk Gulden Lomberg Chemische Fabrik Gmbh	Anellated uracil derivates
AU6908398A (en)	1996-10-28	1998-05-22	Versicor Inc	Fused 2,4-pyrimidinedione combinatorial libraries and biologically active fused 2,4-pyramidinediones
US6331538B1 (en) *	1997-10-28	2001-12-18	Warner-Lambert Company	7-substituted quinazolin-2,4-diones useful as antibacterial agents
EP1080092B1 (en)	1998-05-26	2008-07-23	Warner-Lambert Company LLC	Bicyclic pyrimidines and bicyclic 3,4-dihydropyrimidines as inhibitors of cellular proliferation
WO2000035885A1 (en) *	1998-12-11	2000-06-22	F. Hoffmann-La Roche Ag	Cyclic hydrazine derivatives as tnf-alpha inhibitors

2000
- 2000-12-12 MX MXPA02005989A patent/MXPA02005989A/es active IP Right Grant
- 2000-12-12 BR BR0017010-0A patent/BR0017010A/pt not_active Application Discontinuation
- 2000-12-12 CA CA2393802A patent/CA2393802C/en not_active Expired - Fee Related
- 2000-12-12 AU AU20899/01A patent/AU783078B2/en not_active Ceased
- 2000-12-12 HU HU0204101A patent/HUP0204101A3/hu unknown
- 2000-12-12 EE EEP200200412A patent/EE200200412A/xx unknown
- 2000-12-12 WO PCT/US2000/033656 patent/WO2001053273A1/en active Search and Examination
- 2000-12-12 AT AT00984246T patent/ATE398110T1/de not_active IP Right Cessation
- 2000-12-12 CN CN00818578A patent/CN1425008A/zh active Pending
- 2000-12-12 US US10/182,221 patent/US7094780B1/en not_active Expired - Fee Related
- 2000-12-12 ES ES00984246T patent/ES2304992T3/es not_active Expired - Lifetime
- 2000-12-12 IL IL15039300A patent/IL150393A0/xx unknown
- 2000-12-12 KR KR1020027009515A patent/KR20020067701A/ko not_active Application Discontinuation
- 2000-12-12 SK SK1057-2002A patent/SK10572002A3/sk unknown
- 2000-12-12 EP EP00984246A patent/EP1255739B1/en not_active Expired - Lifetime
- 2000-12-12 AP APAP/P/2002/002603A patent/AP2002002603A0/en unknown
- 2000-12-12 OA OA1200200210A patent/OA12316A/en unknown
- 2000-12-12 EA EA200200661A patent/EA005585B1/ru not_active IP Right Cessation
- 2000-12-12 GE GE4912A patent/GEP20053429B/en unknown
- 2000-12-12 JP JP2001553275A patent/JP4811978B2/ja not_active Expired - Fee Related
- 2000-12-12 PL PL00356837A patent/PL356837A1/xx not_active Application Discontinuation
- 2000-12-12 YU YU55902A patent/YU55902A/sh unknown
- 2000-12-12 DE DE60039194T patent/DE60039194D1/de not_active Expired - Lifetime
2001
- 2001-01-19 PA PA20018510101A patent/PA8510101A1/es unknown
- 2001-01-22 CO CO01004183A patent/CO5320600A1/es not_active Application Discontinuation
- 2001-01-22 HN HN2001000009A patent/HN2001000009A/es unknown
- 2001-01-22 UY UY26551A patent/UY26551A1/es not_active Application Discontinuation
- 2001-01-22 PE PE2001000066A patent/PE20011060A1/es not_active Application Discontinuation
- 2001-01-22 SV SV2001000288A patent/SV2001000288A/es not_active Application Discontinuation
- 2001-01-22 TN TNTNSN01011A patent/TNSN01011A1/en unknown
- 2001-01-23 AR ARP010100278A patent/AR030186A1/es unknown
2002
- 2002-06-27 IS IS6448A patent/IS6448A/is unknown
- 2002-07-19 CR CR6709A patent/CR6709A/es not_active Application Discontinuation
- 2002-07-22 MA MA26734A patent/MA26866A1/fr unknown
- 2002-07-23 NO NO20023516A patent/NO20023516D0/no not_active Application Discontinuation
- 2002-08-22 BG BG107023A patent/BG107023A/xx unknown
- 2002-08-23 HR HR20020696A patent/HRP20020696A2/hr not_active Application Discontinuation
2003
- 2003-09-11 HK HK03106519.6A patent/HK1054237A1/zh unknown
2006
- 2006-06-13 US US11/452,121 patent/US7582627B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2393802C (en)	2011-04-19
CO5320600A1 (es)	2003-09-30
ATE398110T1 (de)	2008-07-15
EA005585B1 (ru)	2005-04-28
US20060183762A1 (en)	2006-08-17
HUP0204101A2 (hu)	2003-04-28
IS6448A (is)	2002-06-27
JP2003520277A (ja)	2003-07-02
HK1054237A1 (zh)	2003-11-21
PE20011060A1 (es)	2001-10-12
PL356837A1 (en)	2004-07-12
NO20023516L (no)	2002-07-23
AR030186A1 (es)	2003-08-13
MA26866A1 (fr)	2004-12-20
HUP0204101A3 (en)	2004-05-28
YU55902A (sh)	2006-01-16
EP1255739A1 (en)	2002-11-13
US7582627B2 (en)	2009-09-01
IL150393A0 (en)	2002-12-01
OA12316A (en)	2006-05-15
SV2001000288A (es)	2001-11-30
AU783078B2 (en)	2005-09-22
CA2393802A1 (en)	2001-07-26
GEP20053429B (en)	2005-01-25
EA200200661A1 (ru)	2003-02-27
US7094780B1 (en)	2006-08-22
PA8510101A1 (es)	2003-06-30
KR20020067701A (ko)	2002-08-23
EE200200412A (et)	2003-10-15
BG107023A (en)	2003-04-30
CR6709A (es)	2003-11-25
NO20023516D0 (no)	2002-07-23
EP1255739B1 (en)	2008-06-11
CN1425008A (zh)	2003-06-18
HN2001000009A (es)	2001-06-13
WO2001053273A1 (en)	2001-07-26
DE60039194D1 (de)	2008-07-24
SK10572002A3 (sk)	2003-10-07
ES2304992T3 (es)	2008-11-01
AU2089901A (en)	2001-07-31
US20060287308A1 (en)	2006-12-21
TNSN01011A1 (en)	2005-11-10
UY26551A1 (es)	2001-04-30
AP2002002603A0 (en)	2002-09-30
JP4811978B2 (ja)	2011-11-09
BR0017010A (pt)	2002-11-05
MXPA02005989A (es)	2002-10-23

Legal Events

Date	Code	Title
2003-12-31	A1OB	Publication of a patent application
2004-06-30	ARAI	Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application
2008-12-11	OBST	Application withdrawn

Publication	Publication Date	Title
EP1255739B1 (en)	2008-06-11	3-aminoquinazolin-2,4-dione antibacterial agents
DE69814135T2 (de)	2004-04-01	7-substituierte chinazolin-2,4-dionen verwendbar als antibakterielle mittel
EP0172651B1 (en)	1990-02-07	Substituted-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylic acids; substituted-5-amino-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids; substituted-5-amino-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids; derivatives thereof; pharmaceutical compositions comprising the compounds; and processes for producing the compounds
HU196986B (en)	1989-02-28	Process for producing new naphtiridine- and quinoline-carboxylic acids of antibacterial activity and pharmaceutical compositions containing them
EP3080131A1 (en)	2016-10-19	Imidazopyridazine compounds useful as modulators of il-12, il-23 and/or ifn alpha responses
EP3541817B1 (en)	2020-12-23	Imidazopyridazine modulators of il-12, il-23 and/or ifn-alpha
JPH0819099B2 (ja)	1996-02-28	アザビシクロキノロンカルボン酸化合物製造用中間体
US20180222904A1 (en)	2018-08-09	Bruton's tyrosine kinase inhibitors
JPH06508366A (ja)	1994-09-22	イミダゾ〔１，５−ａ〕キノキサリン
JP2002533465A (ja)	2002-10-08	Ｘａ因子阻害剤としての窒素を含む複素二環類
JPH0755945B2 (ja)	1995-06-14	抗菌剤
US4771055A (en)	1988-09-13	7-[[3-(aminomethyl)-3-alkyl]-1-pyrrolidinyl]-quinoline-carboxylic acids
EP0362759A1 (en)	1990-04-11	Pyridonecarboxylic acids
US20030114666A1 (en)	2003-06-19	Antibacterial agents
EP0347851B1 (en)	1993-11-10	Quinolonecarboxylic acids
JPH037260A (ja)	1991-01-14	新規キノロン誘導体またはその塩及びこれを含有する抗菌剤
CN112079836A (zh)	2020-12-15	***并嘧啶类化合物及其盐、组合物和应用