HRP960269A2 - Heterocyclic ring-fused pyrimidine derivatives - Google Patents

Heterocyclic ring-fused pyrimidine derivatives Download PDF

Info

Publication number: HRP960269A2
Authority: HR; Croatia
Prior art keywords: pyrimidin; amine; alkyl; pyrido; phenyl
Prior art date: 1995-06-07

Application number

HR95/007,881A

Other languages

English (en)

Croatian (hr)

Inventor

Daniel Arnold Lee

Susan Beth Sobolov-Jaynes

Original Assignee

Pfizer

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.)

1995-06-07

Filing date

1996-06-06

Publication date

1997-08-31

1996-06-06 Application filed by Pfizer filed Critical Pfizer

1997-08-31 Publication of HRP960269A2 publication Critical patent/HRP960269A2/hr

Links

150000003230 pyrimidines Chemical class 0.000 title description 8
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 title description 3
125000000623 heterocyclic group Chemical group 0.000 title 1
-1 nitro, hydroxy, amino Chemical group 0.000 claims description 156
150000001875 compounds Chemical class 0.000 claims description 141
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 77
238000000034 method Methods 0.000 claims description 63
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 53
125000003282 alkyl amino group Chemical group 0.000 claims description 47
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
125000000217 alkyl group Chemical group 0.000 claims description 37
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 34
206010028980 Neoplasm Diseases 0.000 claims description 30
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
125000003545 alkoxy group Chemical group 0.000 claims description 22
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 21
150000001412 amines Chemical class 0.000 claims description 21
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
125000004414 alkyl thio group Chemical group 0.000 claims description 18
125000005236 alkanoylamino group Chemical group 0.000 claims description 17
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 17
238000011282 treatment Methods 0.000 claims description 16
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 15
125000005843 halogen group Chemical group 0.000 claims description 15
229910052757 nitrogen Inorganic materials 0.000 claims description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 15
125000004423 acyloxy group Chemical group 0.000 claims description 14
208000035475 disorder Diseases 0.000 claims description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
230000003463 hyperproliferative effect Effects 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
201000011510 cancer Diseases 0.000 claims description 12
125000005518 carboxamido group Chemical group 0.000 claims description 12
210000004027 cell Anatomy 0.000 claims description 11
201000010099 disease Diseases 0.000 claims description 11
229910052727 yttrium Inorganic materials 0.000 claims description 10
125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 8
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 7
229910052799 carbon Inorganic materials 0.000 claims description 7
230000002062 proliferating effect Effects 0.000 claims description 7
125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 6
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
CXAPZNBQPOKHKN-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)pyrido[3,4-d]pyrimidine Chemical compound N1=CC=C2C(N3CCC4=CC=C(C=C43)Cl)=NC=NC2=C1 CXAPZNBQPOKHKN-UHFFFAOYSA-N 0.000 claims description 6
241000124008 Mammalia Species 0.000 claims description 6
KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
125000005596 alkyl carboxamido group Chemical group 0.000 claims description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
229910052739 hydrogen Inorganic materials 0.000 claims description 6
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
BHPQVEMLECZBDB-UHFFFAOYSA-N n-(1h-indol-5-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C2C(NC=3C=C4C=CNC4=CC=3)=NC=NC2=C1 BHPQVEMLECZBDB-UHFFFAOYSA-N 0.000 claims description 6
LNPZJAMDBWPNSF-UHFFFAOYSA-N n-(3-methylphenyl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 LNPZJAMDBWPNSF-UHFFFAOYSA-N 0.000 claims description 6
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000005494 pyridonyl group Chemical group 0.000 claims description 6
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
VFUAAGBLFHOQAV-UHFFFAOYSA-N 5-bromo-n-(3-ethynylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(Br)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 VFUAAGBLFHOQAV-UHFFFAOYSA-N 0.000 claims description 5
210000001072 colon Anatomy 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
229910052717 sulfur Inorganic materials 0.000 claims description 5
KAIRQZLXOKATIQ-UHFFFAOYSA-N 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carbonitrile Chemical compound C#CC1=CC=CC(NC=2C=3C(C#N)=CNC=3N=CN=2)=C1 KAIRQZLXOKATIQ-UHFFFAOYSA-N 0.000 claims description 4
125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
201000004681 Psoriasis Diseases 0.000 claims description 4
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 4
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
125000003368 amide group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
125000005605 benzo group Chemical group 0.000 claims description 4
210000000481 breast Anatomy 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000001475 halogen functional group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
210000004072 lung Anatomy 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
CVPVAPRGSBCQRN-UHFFFAOYSA-N n-(1h-indazol-5-yl)pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CC=C2C(NC=3C=C4C=NNC4=CC=3)=NC=NC2=C1 CVPVAPRGSBCQRN-UHFFFAOYSA-N 0.000 claims description 4
JXFAHPCDBDADEP-UHFFFAOYSA-N n-(3-ethynyl-4-fluorophenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(F)C(C#C)=C1 JXFAHPCDBDADEP-UHFFFAOYSA-N 0.000 claims description 4
HDARLEDIXFDUNN-UHFFFAOYSA-N n-phenylpyrido[2,3-d]pyrimidin-4-amine Chemical compound N=1C=NC2=NC=CC=C2C=1NC1=CC=CC=C1 HDARLEDIXFDUNN-UHFFFAOYSA-N 0.000 claims description 4
GXHHNATXYAMTDG-UHFFFAOYSA-N n-phenylpyrido[3,4-d]pyrimidin-4-amine Chemical compound N=1C=NC2=CN=CC=C2C=1NC1=CC=CC=C1 GXHHNATXYAMTDG-UHFFFAOYSA-N 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 4
210000002784 stomach Anatomy 0.000 claims description 4
210000003932 urinary bladder Anatomy 0.000 claims description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
XWQYVWRXHMSKRB-UHFFFAOYSA-N 2-methyl-4-[(6-methylpyrido[3,4-d]pyrimidin-4-yl)amino]phenol dihydrochloride Chemical compound Cl.Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(O)C(C)=C1 XWQYVWRXHMSKRB-UHFFFAOYSA-N 0.000 claims description 3
DXZWKHBMXNTZOI-UHFFFAOYSA-N 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carboxylic acid Chemical compound C=12C(C(=O)O)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 DXZWKHBMXNTZOI-UHFFFAOYSA-N 0.000 claims description 3
VYOGNKSYOFTQLH-UHFFFAOYSA-N 4-(4-bromo-7-methyl-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC(C(=CC=C2C)Br)=C2N1C1=C2C=C(C)N=CC2=NC=N1 VYOGNKSYOFTQLH-UHFFFAOYSA-N 0.000 claims description 3
SGLIJWXMPPZXRW-UHFFFAOYSA-N 4-(6,7-dimethyl-2,3-dihydroindol-1-yl)pyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.N1=CC=C2C(N3CCC4=CC=C(C(=C43)C)C)=NC=NC2=C1 SGLIJWXMPPZXRW-UHFFFAOYSA-N 0.000 claims description 3
QPEFVPDESAJGGO-UHFFFAOYSA-N 4-(6-bromo-5-fluoro-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC2=CC(F)=C(Br)C=C2N1C1=C2C=C(C)N=CC2=NC=N1 QPEFVPDESAJGGO-UHFFFAOYSA-N 0.000 claims description 3
YQACOZRQAQJJNS-UHFFFAOYSA-N 6-methyl-n-[3-(trifluoromethyl)phenyl]pyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=CC(C(F)(F)F)=C1 YQACOZRQAQJJNS-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
125000004093 cyano group Chemical group *C#N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
210000003238 esophagus Anatomy 0.000 claims description 3
210000003128 head Anatomy 0.000 claims description 3
210000003734 kidney Anatomy 0.000 claims description 3
210000004185 liver Anatomy 0.000 claims description 3
FSIWLHREFRIZCX-UHFFFAOYSA-N n-(1-benzothiophen-5-yl)pyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CC=C2C(NC=3C=C4C=CSC4=CC=3)=NC=NC2=C1 FSIWLHREFRIZCX-UHFFFAOYSA-N 0.000 claims description 3
ITTZBDQOYAADFL-UHFFFAOYSA-N n-(1h-indol-5-yl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=C2NC=CC2=CC(NC2=C3C=C(N=CC3=NC=N2)C)=C1 ITTZBDQOYAADFL-UHFFFAOYSA-N 0.000 claims description 3
HAWXKROVNIIVEX-UHFFFAOYSA-N n-(3-chlorophenyl)-7-methylpyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C=NC(C)=CC2=NC=NC=1NC1=CC=CC(Cl)=C1 HAWXKROVNIIVEX-UHFFFAOYSA-N 0.000 claims description 3
ZKISXEYMMCKORH-UHFFFAOYSA-N n-(3-chlorophenyl)-7h-purin-6-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C=3N=CNC=3N=CN=2)=C1 ZKISXEYMMCKORH-UHFFFAOYSA-N 0.000 claims description 3
BCLXVHJHHBULCV-UHFFFAOYSA-N n-(3-chlorophenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound ClC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 BCLXVHJHHBULCV-UHFFFAOYSA-N 0.000 claims description 3
RRCDEIQCICOTKZ-UHFFFAOYSA-N n-(3-chlorophenyl)pyrido[4,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC(NC=2C3=CN=CC=C3N=CN=2)=C1 RRCDEIQCICOTKZ-UHFFFAOYSA-N 0.000 claims description 3
YRRBOKHSOVSHSI-UHFFFAOYSA-N n-(3-ethynylphenyl)-5-methyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C=12C(C)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 YRRBOKHSOVSHSI-UHFFFAOYSA-N 0.000 claims description 3
NPMPBDSPHFHHMC-UHFFFAOYSA-N n-(3-ethynylphenyl)-5-methylsulfanyl-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C=12C(SC)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 NPMPBDSPHFHHMC-UHFFFAOYSA-N 0.000 claims description 3
XGPRAWMNWHDJKI-UHFFFAOYSA-N n-(3-ethynylphenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=CC(C#C)=C1 XGPRAWMNWHDJKI-UHFFFAOYSA-N 0.000 claims description 3
YFRSGDRAYOBDPX-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-(2-methoxyethyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(CCOC)C=CC2=C1NC1=CC=CC(C#C)=C1 YFRSGDRAYOBDPX-UHFFFAOYSA-N 0.000 claims description 3
HDNMPTXODRTFCR-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-[2-(2-methoxyethoxy)ethyl]pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound N1=CN=C2N(CCOCCOC)C=CC2=C1NC1=CC=CC(C#C)=C1 HDNMPTXODRTFCR-UHFFFAOYSA-N 0.000 claims description 3
NDKPPINOPXHVPF-UHFFFAOYSA-N n-(3-ethynylphenyl)-7-methylpyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2N(C)C=CC2=C1NC1=CC=CC(C#C)=C1 NDKPPINOPXHVPF-UHFFFAOYSA-N 0.000 claims description 3
LVTUVRVZECNLGU-UHFFFAOYSA-N n-(3-ethynylphenyl)-7h-purin-6-amine Chemical compound C#CC1=CC=CC(NC=2C=3N=CNC=3N=CN=2)=C1 LVTUVRVZECNLGU-UHFFFAOYSA-N 0.000 claims description 3
QFRDWIHAVDMHPE-UHFFFAOYSA-N n-(3-ethynylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C#CC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 QFRDWIHAVDMHPE-UHFFFAOYSA-N 0.000 claims description 3
HNGRZKXBWKRSCA-UHFFFAOYSA-N n-(3-ethynylphenyl)pyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.C#CC1=CC=CC(NC=2C3=CC=NC=C3N=CN=2)=C1 HNGRZKXBWKRSCA-UHFFFAOYSA-N 0.000 claims description 3
XBMUTDGAFSUQOT-UHFFFAOYSA-N n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.CC1=CC=CC(NC=2C=3C=CNC=3N=CN=2)=C1 XBMUTDGAFSUQOT-UHFFFAOYSA-N 0.000 claims description 3
CWHBDBIIXWUAJA-UHFFFAOYSA-N n-(4-bromo-3-fluorophenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(Br)C(F)=C1 CWHBDBIIXWUAJA-UHFFFAOYSA-N 0.000 claims description 3
KHEYWDNIEMRBQT-UHFFFAOYSA-N n-(4-fluoro-3-methylphenyl)-6-methylpyrido[3,4-d]pyrimidin-4-amine;hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(F)C(C)=C1 KHEYWDNIEMRBQT-UHFFFAOYSA-N 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
239000001301 oxygen Chemical group 0.000 claims description 3
210000000496 pancreas Anatomy 0.000 claims description 3
239000000651 prodrug Substances 0.000 claims description 3
229940002612 prodrug Drugs 0.000 claims description 3
XMVJITFPVVRMHC-UHFFFAOYSA-N roxarsone Chemical group OC1=CC=C([As](O)(O)=O)C=C1[N+]([O-])=O XMVJITFPVVRMHC-UHFFFAOYSA-N 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
210000001685 thyroid gland Anatomy 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 2
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
YKYIFUROKBDHCY-ONEGZZNKSA-N (e)-4-ethoxy-1,1,1-trifluorobut-3-en-2-one Chemical group CCO\C=C\C(=O)C(F)(F)F YKYIFUROKBDHCY-ONEGZZNKSA-N 0.000 claims description 2
DKLGVCDKNBPBEQ-UHFFFAOYSA-N 1-[4-(3-methylanilino)pyrrolo[2,3-d]pyrimidin-7-yl]ethanone;hydrochloride Chemical compound Cl.N1=CN=C2N(C(=O)C)C=CC2=C1NC1=CC=CC(C)=C1 DKLGVCDKNBPBEQ-UHFFFAOYSA-N 0.000 claims description 2
CPHXLFKIUVVIOQ-UHFFFAOYSA-N 2-(trifluoromethoxy)benzaldehyde Chemical group FC(F)(F)OC1=CC=CC=C1C=O CPHXLFKIUVVIOQ-UHFFFAOYSA-N 0.000 claims description 2
UZZQOANSYKQBJS-UHFFFAOYSA-N 2-iodo-4-[(6-methylpyrido[3,4-d]pyrimidin-4-yl)amino]phenol hydrochloride Chemical compound Cl.N1=CN=C2C=NC(C)=CC2=C1NC1=CC=C(O)C(I)=C1 UZZQOANSYKQBJS-UHFFFAOYSA-N 0.000 claims description 2
MZJBVKCTGOKCHG-UHFFFAOYSA-N 4-(6-bromo-7-methyl-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine;hydrochloride Chemical compound Cl.C1CC2=CC=C(Br)C(C)=C2N1C1=C2C=C(C)N=CC2=NC=N1 MZJBVKCTGOKCHG-UHFFFAOYSA-N 0.000 claims description 2
LOPBUDCQZDQIQH-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-5,7-dihydropyrrolo[2,3-d]pyrimidin-6-one Chemical compound ClC1=CC=C2CCN(C2=C1)C=1C2=C(N=CN=1)N=C(C2)O LOPBUDCQZDQIQH-UHFFFAOYSA-N 0.000 claims description 2
PQTYWQWATNSLSN-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-6-methylpyrido[3,4-d]pyrimidine Chemical compound C1CC2=CC=C(Cl)C=C2N1C1=C2C=C(C)N=CC2=NC=N1 PQTYWQWATNSLSN-UHFFFAOYSA-N 0.000 claims description 2
RKBKLXOJDZURGJ-UHFFFAOYSA-N 4-(6-chloro-2,3-dihydroindol-1-yl)-7h-pyrrolo[2,3-d]pyrimidine;hydrochloride Chemical compound Cl.C12=CC(Cl)=CC=C2CCN1C1=NC=NC2=C1C=CN2 RKBKLXOJDZURGJ-UHFFFAOYSA-N 0.000 claims description 2
WMAOJUAPQNRXMN-UHFFFAOYSA-N 5-iodo-n-(3-methylphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound CC1=CC=CC(NC=2C=3C(I)=CNC=3N=CN=2)=C1 WMAOJUAPQNRXMN-UHFFFAOYSA-N 0.000 claims description 2
MMGGSCIGUVFESP-UHFFFAOYSA-N 6-methyl-n-[3-(trifluoromethyl)phenyl]pyrido[3,4-d]pyrimidin-4-amine Chemical compound N1=CN=C2C=NC(C)=CC2=C1NC1=CC=CC(C(F)(F)F)=C1 MMGGSCIGUVFESP-UHFFFAOYSA-N 0.000 claims description 2
OZMLAELAHCCJQD-UHFFFAOYSA-N 7-(benzenesulfonyl)-n-(3-ethynylphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=CC2=C(NC=3C=C(C=CC=3)C#C)N=CN=C2N1S(=O)(=O)C1=CC=CC=C1 OZMLAELAHCCJQD-UHFFFAOYSA-N 0.000 claims description 2
206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
208000003174 Brain Neoplasms Diseases 0.000 claims description 2
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
208000004403 Prostatic Hyperplasia Diseases 0.000 claims description 2
125000000033 alkoxyamino group Chemical group 0.000 claims description 2
125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
150000001721 carbon Chemical group 0.000 claims description 2
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000003843 furanosyl group Chemical group 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
CRKWNMCCIJMCBS-UHFFFAOYSA-N methyl 4-(3-ethynylanilino)-7h-pyrrolo[2,3-d]pyrimidine-5-carboxylate Chemical compound C=12C(C(=O)OC)=CNC2=NC=NC=1NC1=CC=CC(C#C)=C1 CRKWNMCCIJMCBS-UHFFFAOYSA-N 0.000 claims description 2
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XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
FJVZDOGVDJCCCR-UHFFFAOYSA-M potassium periodate Chemical compound [K+].[O-]I(=O)(=O)=O FJVZDOGVDJCCCR-UHFFFAOYSA-M 0.000 description 1
OKBMCNHOEMXPTM-UHFFFAOYSA-M potassium peroxymonosulfate Chemical compound [K+].OOS([O-])(=O)=O OKBMCNHOEMXPTM-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000012256 powdered iron Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000008569 process Effects 0.000 description 1
230000009696 proliferative response Effects 0.000 description 1
159000000018 pyrido[2,3-d]pyrimidines Chemical class 0.000 description 1
OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 description 1
150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
206010038038 rectal cancer Diseases 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
201000001275 rectum cancer Diseases 0.000 description 1
230000004044 response Effects 0.000 description 1
208000037803 restenosis Diseases 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
125000004469 siloxy group Chemical group [SiH3]O* 0.000 description 1
239000010802 sludge Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
QJDUDPQVDAASMV-UHFFFAOYSA-M sodium;ethanethiolate Chemical compound [Na+].CC[S-] QJDUDPQVDAASMV-UHFFFAOYSA-M 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
201000011549 stomach cancer Diseases 0.000 description 1
125000003011 styrenyl group Chemical class [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
150000003461 sulfonyl halides Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
239000003765 sweetening agent Substances 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
239000007916 tablet composition Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 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
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000001107 thermogravimetry coupled to mass spectrometry Methods 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
208000013076 thyroid tumor Diseases 0.000 description 1
238000004448 titration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
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 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 description 1
125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
LSGOVYNHVSXFFJ-UHFFFAOYSA-N vanadate(3-) Chemical compound [O-][V]([O-])([O-])=O LSGOVYNHVSXFFJ-UHFFFAOYSA-N 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom

HR95/007,881A 1995-06-07 1996-06-06 Heterocyclic ring-fused pyrimidine derivatives HRP960269A2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/US1995/007881 WO1996040142A1 (en)	1995-06-07	1995-06-07	Heterocyclic ring-fused pyrimidine derivatives
HU9601559A HUP9601559A3 (en)	1995-06-07	1996-06-06	Heterocyclic ring-fused pyrimidine derivatives, pharmaceutical compositions containing the same and intermediates

Publications (1)

Publication Number	Publication Date
HRP960269A2 true HRP960269A2 (en)	1997-08-31

Family

ID=89994036

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HR95/007,881A HRP960269A2 (en)	1995-06-07	1996-06-06	Heterocyclic ring-fused pyrimidine derivatives

Country Status (32)

Country	Link
EP (1)	EP0831829B1 (es)
JP (1)	JP3290666B2 (es)
CN (1)	CN1141298A (es)
AP (1)	AP637A (es)
AR (1)	AR002746A1 (es)
AT (1)	ATE247469T1 (es)
AU (1)	AU5479196A (es)
BR (1)	BR9602695A (es)
CA (1)	CA2223081C (es)
CO (1)	CO4440628A1 (es)
CZ (1)	CZ164196A3 (es)
DE (1)	DE69531558T2 (es)
DK (1)	DK0831829T3 (es)
ES (1)	ES2203642T3 (es)
FI (1)	FI974443A0 (es)
HR (1)	HRP960269A2 (es)
HU (1)	HUP9601559A3 (es)
IL (1)	IL118487A0 (es)
MA (1)	MA26409A1 (es)
MX (1)	MX9709867A (es)
NO (1)	NO962386L (es)
NZ (1)	NZ286755A (es)
OA (1)	OA10460A (es)
PL (1)	PL314641A1 (es)
PT (1)	PT831829E (es)
RU (1)	RU2136683C1 (es)
SG (1)	SG45483A1 (es)
SI (1)	SI9600184A (es)
SK (1)	SK72996A3 (es)
TR (1)	TR199600474A2 (es)
WO (1)	WO1996040142A1 (es)
ZA (1)	ZA964725B (es)

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1995
- 1995-06-07 MX MX9709867A patent/MX9709867A/es not_active IP Right Cessation
- 1995-06-07 DK DK95924027T patent/DK0831829T3/da active
- 1995-06-07 AT AT95924027T patent/ATE247469T1/de not_active IP Right Cessation
- 1995-06-07 SK SK729-96A patent/SK72996A3/sk unknown
- 1995-06-07 JP JP50039097A patent/JP3290666B2/ja not_active Expired - Fee Related
- 1995-06-07 DE DE69531558T patent/DE69531558T2/de not_active Expired - Fee Related
- 1995-06-07 EP EP95924027A patent/EP0831829B1/en not_active Expired - Lifetime
- 1995-06-07 CA CA002223081A patent/CA2223081C/en not_active Expired - Fee Related
- 1995-06-07 PT PT95924027T patent/PT831829E/pt unknown
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- 1995-06-07 WO PCT/US1995/007881 patent/WO1996040142A1/en active IP Right Grant
1996
- 1996-05-09 AP APAP/P/1996/000805A patent/AP637A/en active
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- 1996-06-03 MA MA24256A patent/MA26409A1/fr unknown
- 1996-06-05 SG SG1996009982A patent/SG45483A1/en unknown
- 1996-06-05 PL PL96314641A patent/PL314641A1/xx unknown
- 1996-06-05 CN CN96108101A patent/CN1141298A/zh active Pending
- 1996-06-06 AU AU54791/96A patent/AU5479196A/en not_active Abandoned
- 1996-06-06 SI SI9600184A patent/SI9600184A/sl unknown
- 1996-06-06 HR HR95/007,881A patent/HRP960269A2/hr not_active Application Discontinuation
- 1996-06-06 HU HU9601559A patent/HUP9601559A3/hu unknown
- 1996-06-06 CZ CZ961641A patent/CZ164196A3/cs unknown
- 1996-06-06 NZ NZ286755A patent/NZ286755A/en unknown
- 1996-06-06 NO NO962386A patent/NO962386L/no unknown
- 1996-06-06 ZA ZA9604725A patent/ZA964725B/xx unknown
- 1996-06-06 TR TR96/00474A patent/TR199600474A2/xx unknown
- 1996-06-07 BR BR9602695A patent/BR9602695A/pt active Search and Examination
- 1996-06-07 OA OA60838A patent/OA10460A/en unknown
- 1996-06-07 RU RU96111016A patent/RU2136683C1/ru active
- 1996-06-07 CO CO96029731A patent/CO4440628A1/es unknown
1997
- 1997-12-05 FI FI974443A patent/FI974443A0/fi unknown

Also Published As

Publication number	Publication date
OA10460A (en)	2002-03-28
NO962386L (no)	1996-12-09
JPH10508875A (ja)	1998-09-02
AR002746A1 (es)	1998-04-29
SK72996A3 (en)	1997-04-09
IL118487A0 (en)	1996-09-12
BR9602695A (pt)	1998-10-06
SI9600184A (en)	1997-04-30
PT831829E (pt)	2003-12-31
PL314641A1 (en)	1996-12-09
CA2223081A1 (en)	1996-12-19
ATE247469T1 (de)	2003-09-15
CZ164196A3 (en)	1996-12-11
EP0831829A1 (en)	1998-04-01
WO1996040142A1 (en)	1996-12-19
FI974443A (fi)	1997-12-05
NZ286755A (en)	1998-03-25
AP637A (en)	1998-04-08
SG45483A1 (en)	1998-01-16
EP0831829B1 (en)	2003-08-20
MA26409A1 (fr)	2004-12-20
DK0831829T3 (da)	2003-12-15
HUP9601559A2 (en)	1997-02-28
CO4440628A1 (es)	1997-05-07
CA2223081C (en)	2001-03-06
TR199600474A2 (tr)	1996-12-21
DE69531558D1 (de)	2003-09-25
EP0831829A4 (en)	1998-11-25
ZA964725B (en)	1997-12-08
DE69531558T2 (de)	2004-03-18
ES2203642T3 (es)	2004-04-16
AU5479196A (en)	1996-12-19
AP9600805A0 (en)	1996-07-31
JP3290666B2 (ja)	2002-06-10
HU9601559D0 (en)	1996-08-28
HUP9601559A3 (en)	1997-07-28
RU2136683C1 (ru)	1999-09-10
CN1141298A (zh)	1997-01-29
MX9709867A (es)	1998-03-31
FI974443A0 (fi)	1997-12-05
NO962386D0 (no)	1996-06-06

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Date	Code	Title	Description
1996-06-06	AIPI	Request for the grant of a patent on the basis of a substantive examination of a patent application
1997-08-31	A1OB	Publication of a patent application
1999-06-06	ODRP	Renewal fee for the maintenance of a patent	Payment date: 19990606 Year of fee payment: 4
2005-02-25	ODBC	Application rejected

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