AU2001266505A1 - Substituted quinazoline derivatives and their use as inhibitors - Google Patents

Substituted quinazoline derivatives and their use as inhibitors

Info

Publication number: AU2001266505A1
Authority: AU; Australia
Prior art keywords: alkyl; compound; mmol; optionally substituted; starting
Prior art date: 2000-06-28
Legal status (The legal status 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 status listed.): Abandoned

Application number

AU2001266505A

Other languages

English (en)

Inventor

Frederic Jung

Andrew Mortlock

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

AstraZeneca AB

Original Assignee

AstraZeneca AB

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.)

2000-06-28

Filing date

2001-06-21

Publication date

2002-01-08

2001-06-21 Application filed by AstraZeneca AB filed Critical AstraZeneca AB

2002-01-08 Publication of AU2001266505A1 publication Critical patent/AU2001266505A1/en

Status Abandoned legal-status Critical Current

Links

239000003112 inhibitor Substances 0.000 title description 3
125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 969
238000002360 preparation method Methods 0.000 claims description 391
-1 Cι-3alkyl Chemical group 0.000 claims description 102
239000000203 mixture Substances 0.000 claims description 101
229910052739 hydrogen Inorganic materials 0.000 claims description 68
239000001257 hydrogen Substances 0.000 claims description 68
125000000623 heterocyclic group Chemical group 0.000 claims description 54
150000002148 esters Chemical class 0.000 claims description 43
108090000461 Aurora Kinase A Proteins 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
125000004356 hydroxy functional group Chemical group O* 0.000 claims description 35
102100032311 Aurora kinase A Human genes 0.000 claims description 33
125000003118 aryl group Chemical group 0.000 claims description 31
125000001424 substituent group Chemical group 0.000 claims description 31
125000000217 alkyl group Chemical group 0.000 claims description 27
125000005843 halogen group Chemical group 0.000 claims description 27
238000000034 method Methods 0.000 claims description 27
229910052757 nitrogen Inorganic materials 0.000 claims description 27
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
241000282414 Homo sapiens Species 0.000 claims description 22
229910052799 carbon Inorganic materials 0.000 claims description 21
150000003839 salts Chemical class 0.000 claims description 20
125000001072 heteroaryl group Chemical group 0.000 claims description 19
150000002431 hydrogen Chemical class 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
125000001183 hydrocarbyl group Chemical group 0.000 claims description 16
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
241001465754 Metazoa Species 0.000 claims description 15
150000001408 amides Chemical class 0.000 claims description 15
125000004093 cyano group Chemical group *C#N 0.000 claims description 15
229910052760 oxygen Inorganic materials 0.000 claims description 15
238000011282 treatment Methods 0.000 claims description 15
125000005842 heteroatom Chemical group 0.000 claims description 14
238000001727 in vivo Methods 0.000 claims description 14
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
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 claims description 11
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
125000000547 substituted alkyl group Chemical group 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
125000004043 oxo group Chemical group O=* 0.000 claims description 9
229910052717 sulfur Inorganic materials 0.000 claims description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 7
125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
150000001721 carbon Chemical group 0.000 claims description 5
230000005764 inhibitory process Effects 0.000 claims description 5
125000004122 cyclic group Chemical group 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical group OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 3
JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical class O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 3
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
229910020008 S(O) Inorganic materials 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 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
LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical compound O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 2
125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
125000003282 alkyl amino group Chemical group 0.000 claims 1
238000005160 1H NMR spectroscopy Methods 0.000 description 490
238000006243 chemical reaction Methods 0.000 description 470
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 376
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 282
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 254
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 122
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 122
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 100
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 98
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
239000007787 solid Substances 0.000 description 85
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
239000002904 solvent Substances 0.000 description 59
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 58
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 56
239000000243 solution Substances 0.000 description 53
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 51
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 41
238000010898 silica gel chromatography Methods 0.000 description 40
WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 34
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 30
210000004027 cell Anatomy 0.000 description 29
239000011541 reaction mixture Substances 0.000 description 28
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 26
235000019439 ethyl acetate Nutrition 0.000 description 26
ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 24
229940093499 ethyl acetate Drugs 0.000 description 23
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 23
238000010992 reflux Methods 0.000 description 23
PNPCRKVUWYDDST-UHFFFAOYSA-N 3-chloroaniline Chemical compound NC1=CC=CC(Cl)=C1 PNPCRKVUWYDDST-UHFFFAOYSA-N 0.000 description 22
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 22
229910000030 sodium bicarbonate Inorganic materials 0.000 description 22
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 21
AXNUZKSSQHTNPZ-UHFFFAOYSA-N 3,4-difluoroaniline Chemical compound NC1=CC=C(F)C(F)=C1 AXNUZKSSQHTNPZ-UHFFFAOYSA-N 0.000 description 20
238000001914 filtration Methods 0.000 description 20
YSEMCVGMNUUNRK-UHFFFAOYSA-N 3-chloro-4-fluoroaniline Chemical compound NC1=CC=C(F)C(Cl)=C1 YSEMCVGMNUUNRK-UHFFFAOYSA-N 0.000 description 19
206010028980 Neoplasm Diseases 0.000 description 19
239000003480 eluent Substances 0.000 description 19
KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 18
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 17
JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 16
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 16
230000022131 cell cycle Effects 0.000 description 16
229940073584 methylene chloride Drugs 0.000 description 16
RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
239000002244 precipitate Substances 0.000 description 16
235000011121 sodium hydroxide Nutrition 0.000 description 16
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
239000004480 active ingredient Substances 0.000 description 15
229910052943 magnesium sulfate Inorganic materials 0.000 description 15
QZVQQUVWFIZUBQ-UHFFFAOYSA-N 3-fluoroaniline Chemical compound NC1=CC=CC(F)=C1 QZVQQUVWFIZUBQ-UHFFFAOYSA-N 0.000 description 14
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 14
PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 14
KQOIBXZRCYFZSO-UHFFFAOYSA-N 3,5-difluoroaniline Chemical compound NC1=CC(F)=CC(F)=C1 KQOIBXZRCYFZSO-UHFFFAOYSA-N 0.000 description 13
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 13
201000010099 disease Diseases 0.000 description 13
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
125000000524 functional group Chemical group 0.000 description 13
235000017557 sodium bicarbonate Nutrition 0.000 description 13
QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
230000000694 effects Effects 0.000 description 12
229910000069 nitrogen hydride Inorganic materials 0.000 description 12
239000000725 suspension Substances 0.000 description 12
238000012360 testing method Methods 0.000 description 12
NJXPYZHXZZCTNI-UHFFFAOYSA-N 3-aminobenzonitrile Chemical compound NC1=CC=CC(C#N)=C1 NJXPYZHXZZCTNI-UHFFFAOYSA-N 0.000 description 11
125000003545 alkoxy group Chemical group 0.000 description 11
150000001409 amidines Chemical class 0.000 description 11
230000015572 biosynthetic process Effects 0.000 description 11
239000003921 oil Substances 0.000 description 11
235000019198 oils Nutrition 0.000 description 11
108090000623 proteins and genes Proteins 0.000 description 11
239000012047 saturated solution Substances 0.000 description 11
KMHLGVTVACLEJE-UHFFFAOYSA-N 4-fluoro-2-methylaniline Chemical compound CC1=CC(F)=CC=C1N KMHLGVTVACLEJE-UHFFFAOYSA-N 0.000 description 10
OPKOKAMJFNKNAS-UHFFFAOYSA-N N-methylethanolamine Chemical compound CNCCO OPKOKAMJFNKNAS-UHFFFAOYSA-N 0.000 description 10
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 10
DGLFSNZWRYADFC-UHFFFAOYSA-N chembl2334586 Chemical compound C1CCC2=CN=C(N)N=C2C2=C1NC1=CC=C(C#CC(C)(O)C)C=C12 DGLFSNZWRYADFC-UHFFFAOYSA-N 0.000 description 10
VYFOAVADNIHPTR-UHFFFAOYSA-N isatoic anhydride Chemical compound NC1=CC=CC=C1CO VYFOAVADNIHPTR-UHFFFAOYSA-N 0.000 description 10
NCBZRJODKRCREW-UHFFFAOYSA-N m-anisidine Chemical compound COC1=CC=CC(N)=C1 NCBZRJODKRCREW-UHFFFAOYSA-N 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
QZUXMXZNVAJNSE-UHFFFAOYSA-N 2-fluoro-5-methylaniline Chemical compound CC1=CC=C(F)C(N)=C1 QZUXMXZNVAJNSE-UHFFFAOYSA-N 0.000 description 9
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 9
238000003556 assay Methods 0.000 description 9
201000011510 cancer Diseases 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 8
ZQEXBVHABAJPHJ-UHFFFAOYSA-N 2-fluoro-4-methylaniline Chemical compound CC1=CC=C(N)C(F)=C1 ZQEXBVHABAJPHJ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
229910052786 argon Inorganic materials 0.000 description 8
230000014509 gene expression Effects 0.000 description 8
HDOWRFHMPULYOA-UHFFFAOYSA-N piperidin-4-ol Chemical compound OC1CCNCC1 HDOWRFHMPULYOA-UHFFFAOYSA-N 0.000 description 8
239000000843 powder Substances 0.000 description 8
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical class N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 8
UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 8
CEPCPXLLFXPZGW-UHFFFAOYSA-N 2,4-difluoroaniline Chemical compound NC1=CC=C(F)C=C1F CEPCPXLLFXPZGW-UHFFFAOYSA-N 0.000 description 7
YNOOQIUSYGWMSS-UHFFFAOYSA-N 2,5-difluoroaniline Chemical compound NC1=CC(F)=CC=C1F YNOOQIUSYGWMSS-UHFFFAOYSA-N 0.000 description 7
FTZQXOJYPFINKJ-UHFFFAOYSA-N 2-fluoroaniline Chemical compound NC1=CC=CC=C1F FTZQXOJYPFINKJ-UHFFFAOYSA-N 0.000 description 7
LJWAPDSCYTZUJU-UHFFFAOYSA-N 3-fluoro-4-methoxyaniline Chemical compound COC1=CC=C(N)C=C1F LJWAPDSCYTZUJU-UHFFFAOYSA-N 0.000 description 7
XJCVRTZCHMZPBD-UHFFFAOYSA-N 3-nitroaniline Chemical compound NC1=CC=CC([N+]([O-])=O)=C1 XJCVRTZCHMZPBD-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
102000004190 Enzymes Human genes 0.000 description 7
108090000790 Enzymes Proteins 0.000 description 7
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 7
HIGRAKVNKLCVCA-UHFFFAOYSA-N alumine Chemical compound C1=CC=[Al]C=C1 HIGRAKVNKLCVCA-UHFFFAOYSA-N 0.000 description 7
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 7
239000007859 condensation product Substances 0.000 description 7
229960001760 dimethyl sulfoxide Drugs 0.000 description 7
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 7
VMPITZXILSNTON-UHFFFAOYSA-N o-anisidine Chemical compound COC1=CC=CC=C1N VMPITZXILSNTON-UHFFFAOYSA-N 0.000 description 7
239000000546 pharmaceutical excipient Substances 0.000 description 7
239000000047 product Substances 0.000 description 7
230000002062 proliferating effect Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
CSFDTBRRIBJILD-UHFFFAOYSA-N 4-chloro-2-fluoroaniline Chemical compound NC1=CC=C(Cl)C=C1F CSFDTBRRIBJILD-UHFFFAOYSA-N 0.000 description 6
MAXBVGJEFDMHNV-UHFFFAOYSA-N 5-chloropyridin-2-amine Chemical compound NC1=CC=C(Cl)C=N1 MAXBVGJEFDMHNV-UHFFFAOYSA-N 0.000 description 6
JLCDTNNLXUMYFQ-UHFFFAOYSA-N 5-fluoro-2-methylaniline Chemical compound CC1=CC=C(F)C=C1N JLCDTNNLXUMYFQ-UHFFFAOYSA-N 0.000 description 6
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HVVNJUAVDAZWCB-RXMQYKEDSA-N D-prolinol Chemical compound OC[C@H]1CCCN1 HVVNJUAVDAZWCB-RXMQYKEDSA-N 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
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LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

AU2001266505A 2000-06-28 2001-06-21 Substituted quinazoline derivatives and their use as inhibitors Abandoned AU2001266505A1 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
EP00401842		2000-06-28
EP00401842		2000-06-28
PCT/SE2001/001450 WO2002000649A1 (en)	2000-06-28	2001-06-21	Substituted quinazoline derivatives and their use as inhibitors

Publications (1)

Publication Number	Publication Date
AU2001266505A1 true AU2001266505A1 (en)	2002-01-08

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ID=8173742

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AU2001266505A Abandoned AU2001266505A1 (en)	2000-06-28	2001-06-21	Substituted quinazoline derivatives and their use as inhibitors

Country Status (27)

Country	Link
US (2)	US6919338B2 (et)
EP (1)	EP1299381B1 (et)
JP (1)	JP2004501914A (et)
KR (1)	KR20030014411A (et)
CN (1)	CN1267431C (et)
AR (1)	AR030432A1 (et)
AT (1)	ATE394102T1 (et)
AU (1)	AU2001266505A1 (et)
BG (1)	BG107376A (et)
BR (1)	BR0111754A (et)
CA (1)	CA2412592A1 (et)
CZ (1)	CZ20024120A3 (et)
DE (1)	DE60133897D1 (et)
EE (1)	EE200200715A (et)
ES (1)	ES2305081T3 (et)
HK (1)	HK1053124A1 (et)
HU (1)	HUP0301236A2 (et)
IL (1)	IL153246A0 (et)
IS (1)	IS6656A (et)
MX (1)	MXPA02011974A (et)
NO (1)	NO20026010D0 (et)
NZ (1)	NZ522696A (et)
PL (1)	PL360439A1 (et)
RU (1)	RU2283311C2 (et)
SK (1)	SK18102002A3 (et)
WO (1)	WO2002000649A1 (et)
ZA (1)	ZA200209412B (et)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113311166A (zh) *	2021-04-28	2021-08-27	新疆农垦科学院	一种用于绵羊早期妊娠诊断的蛋白生物标志物及其用于绵羊早期妊娠检测的方法
CN115557601A (zh) *	2022-11-08	2023-01-03	成都理工大学	生物质微球及其制备方法与应用、生物反应器、地下井

Families Citing this family (98)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7473691B2 (en) *	2000-09-15	2009-01-06	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
MXPA03002299A (es)	2000-09-15	2003-06-06	Vertex Pharma	Compuestos de pirazol utiles como inhibidores de proteina cinasa.
US6660731B2 (en) *	2000-09-15	2003-12-09	Vertex Pharmaceuticals Incorporated	Pyrazole compounds useful as protein kinase inhibitors
ATE528303T1 (de) *	2000-12-21	2011-10-15	Vertex Pharma	Pyrazoleverbindungen als proteinkinasehemmer
DK1463506T3 (da)	2001-12-24	2010-01-11	Astrazeneca Ab	Substituerede quinazolin-derivater som inhibitorer af aurora-kinaser
WO2003066629A2 (en) *	2002-02-06	2003-08-14	Vertex Pharmaceuticals Incorporated	Heteroaryl compounds useful as inhibitors of gsk-3
DK1482931T3 (da) *	2002-03-05	2011-12-19	Transtech Pharma Inc	Mono- og bicycliske azolderivater der inhiberer interaktionen af ligander med RAGE
ATE468336T1 (de) *	2002-03-15	2010-06-15	Vertex Pharma	Azolylaminoazine als proteinkinasehemmer
EP2316834A1 (en)	2002-05-06	2011-05-04	Vertex Pharmaceuticals Incorporated	Thiadiazoles or oxadiazoles and their use as inhibitors of JAK protein kinase
MY141867A (en) *	2002-06-20	2010-07-16	Vertex Pharma	Substituted pyrimidines useful as protein kinase inhibitors
EP2277867B1 (en)	2002-07-15	2012-12-05	Symphony Evolution, Inc.	Compounds, pharmaceutical compositions thereof and their use in treating cancer
DE60308387T2 (de) *	2002-08-02	2007-09-20	Vertex Pharmaceuticals Inc., Cambridge	Pyrazolenthaltende zusammensetzungen und ihre verwendung als gsk-3 inhibitoren
GB0221245D0 (en) *	2002-09-13	2002-10-23	Astrazeneca Ab	Chemical process
AU2003290313B2 (en) *	2002-12-24	2007-05-10	Astrazeneca Ab	Phosphonooxy quinazoline derivatives and their pharmaceutical use
MXPA05006920A (es) *	2002-12-24	2006-02-10	Astrazeneca Ab	Compuestos de quinazolina.
UA86470C2 (ru) *	2002-12-24	2009-04-27	Астразенека Аб	Производные фосфонооксихиназолина и их фармацевтическое применение
US7601718B2 (en) *	2003-02-06	2009-10-13	Vertex Pharmaceuticals Incorporated	Compositions useful as inhibitors of protein kinases
KR20060003351A (ko) *	2003-04-16	2006-01-10	아스트라제네카 아베	화합물
ZA200508300B (en) *	2003-05-20	2007-03-28	Transtech Pharma Inc	RAGE antagonists as agents to reverse amyloidosis and diseases associated therewith
WO2004105764A1 (en) *	2003-06-02	2004-12-09	Astrazeneca Ab	(3- ((quinazolin-4-yl) amino )-1h-pyrazol-1-yl) acetamide derivatives and related compounds as aurora kinase inhibitors for the treatment of proliferative diseases such as cancer
TW200505452A (en) *	2003-06-17	2005-02-16	Astrazeneca Ab	Chemical compounds
GB0320793D0 (en) *	2003-09-05	2003-10-08	Astrazeneca Ab	Chemical process
ES2371383T3 (es)	2003-09-26	2011-12-30	Exelixis, Inc.	N-[3-fluoro-4-({6-(metiloxi)-7-[(3-morfolin-4-ilpropil)oxi]quinolin-4-il}oxi)fenil]-n'-(4-fluorofenil)ciclopropan-1,1-dicarboxamida para el tratamiento del cáncer.
US20090143399A1 (en) *	2003-10-14	2009-06-04	Arizona Board Of Regents On Behalf Of The University Of Arizona	Protein Kinase Inhibitors
US20080051414A1 (en) *	2003-10-14	2008-02-28	Arizona Board Of Regents On Behalf Of The University Of Arizona	Protein Kinase Inhibitors
CA2542076C (en) *	2003-10-14	2013-02-26	Arizona Board Of Regents On Behalf Of The University Of Arizona	Substituted tricyclic compounds as protein kinase inhibitors
US20090099165A1 (en) *	2003-10-14	2009-04-16	Arizona Board Of Regents On Behalf Of The University Of Arizona	Protein Kinase Inhibitors
CA2540342A1 (en) *	2003-10-31	2005-05-12	Neurogen Corporation	4-amino (aza) quinoline derivatives as capsaicin receptor agonists
WO2005056547A2 (en) *	2003-12-04	2005-06-23	Vertex Pharmaceuticals Incorporated	Quinoxalines useful as inhibitors of protein kinases
US7572914B2 (en) *	2003-12-19	2009-08-11	Takeda Pharmaceutical Company Limited	Kinase inhibitors
US8119684B2 (en) *	2003-12-30	2012-02-21	Dana-Farber Cancer Institute, Inc.	Thiophene derivatives for up-regulating HLA-DM activity
JPWO2005090332A1 (ja) *	2004-03-23	2008-01-31	萬有製薬株式会社	置換キナゾリン又はピリドピリミジン誘導体
US20050250829A1 (en) *	2004-04-23	2005-11-10	Takeda San Diego, Inc.	Kinase inhibitors
US7550598B2 (en) *	2004-08-18	2009-06-23	Takeda Pharmaceutical Company Limited	Kinase inhibitors
US20090036485A1 (en) *	2004-10-12	2009-02-05	Frederic Henri Jung	Quinoline derivatives
JP4237242B2 (ja) *	2004-10-12	2009-03-11	アストラゼネカアクチボラグ	キナゾリン誘導体
DE602005023333D1 (de)	2004-10-15	2010-10-14	Takeda Pharmaceutical	Kinaseinhibitoren
CN1854130B (zh) *	2005-04-15	2011-04-20	中国医学科学院药物研究所	喹唑啉衍生物、及其制法和药物组合物与用途
GB0509227D0 (en) *	2005-05-05	2005-06-15	Chroma Therapeutics Ltd	Intracellular enzyme inhibitors
GB0510963D0 (en) *	2005-05-28	2005-07-06	Astrazeneca Ab	Chemical compounds
EP1917259B1 (en) *	2005-08-18	2012-01-25	Vertex Pharmaceuticals Incorporated	Pyrazine kinase inhibitors
US8119655B2 (en)	2005-10-07	2012-02-21	Takeda Pharmaceutical Company Limited	Kinase inhibitors
EP1948193B1 (en) *	2005-11-03	2015-01-07	Vertex Pharmaceuticals Incorporated	Aminopyrimidines useful as kinase inhibitors
EP1785420A1 (en) *	2005-11-14	2007-05-16	4Sc Ag	Thiazole analogues and uses thereof
EA018128B1 (ru)	2006-01-23	2013-05-30	Амген Инк.	Модуляторы аурора киназы, способы их получения и их применение
US7560551B2 (en)	2006-01-23	2009-07-14	Amgen Inc.	Aurora kinase modulators and method of use
US7868177B2 (en) *	2006-02-24	2011-01-11	Amgen Inc.	Multi-cyclic compounds and method of use
JP2009528336A (ja) *	2006-03-02	2009-08-06	アストラゼネカアクチボラグ	キノリン誘導体
UY30183A1 (es) *	2006-03-02	2007-10-31	Astrazeneca Ab	Derivados de quinolina
WO2007113005A2 (en) *	2006-04-03	2007-10-11	European Molecular Biology Laboratory (Embl)	2-substituted 3-aminosulfonyl-thiophene derivatives as aurora kinase inhibitors
EA200970361A1 (ru)	2006-10-09	2010-02-26	Такеда Фармасьютикал Компани Лимитед	Ингибиторы киназы
WO2008044045A1 (en)	2006-10-12	2008-04-17	Astex Therapeutics Limited	Pharmaceutical combinations
JP5528806B2 (ja)	2006-10-12	2014-06-25	アステックス、セラピューティックス、リミテッド	複合薬剤
US8236823B2 (en)	2006-10-27	2012-08-07	Amgen Inc.	Multi-cyclic compounds and methods of use
WO2008055233A1 (en) *	2006-10-31	2008-05-08	Supergen, Inc.	Protein kinase inhibitors
MX2009004807A (es) *	2006-11-02	2009-06-15	Vertex Pharma	Aminopiridinas y aminopirimidinas utiles como inhibidores de proteina cinasa.
CA2673353A1 (en) *	2006-12-19	2008-06-26	Vertex Pharmaceuticals Incorporated	Aminopyrimidines useful as inhibitors of protein kinases
CN101668760B (zh) *	2007-03-09	2013-07-24	沃泰克斯药物股份有限公司	用作蛋白激酶抑制剂的氨基嘧啶类
NZ579483A (en)	2007-03-09	2012-07-27	Vertex Pharma	Aminopyridines useful as inhibitors of protein kinases
CA2679884A1 (en) *	2007-03-09	2008-09-18	Vertex Pharmaceuticals Incorporated	Aminopyrimidines useful as inhibitors of protein kinases
US7776857B2 (en) *	2007-04-05	2010-08-17	Amgen Inc.	Aurora kinase modulators and method of use
JP2010523700A (ja)	2007-04-13	2010-07-15	バーテックスファーマシューティカルズインコーポレイテッド	キナーゼインヒビターとして有用なアミノピリミジン
CN101801959A (zh) *	2007-05-02	2010-08-11	沃泰克斯药物股份有限公司	可用作激酶抑制剂的氨基嘧啶类化合物
MX2009011810A (es) *	2007-05-02	2010-01-14	Vertex Pharma	Tiazoles y pirazoles utiles como inhibidores de cinasa.
EP2155730A2 (en) *	2007-05-02	2010-02-24	Vertex Pharmaceuticals Incorporated	Aminopyrimidines useful as kinase inhibitors
GB0709031D0 (en) *	2007-05-10	2007-06-20	Sareum Ltd	Pharmaceutical compounds
MX2009012719A (es) *	2007-05-24	2010-02-04	Vertex Pharma	Tiazoles y pirazoles utiles como inhibidores de cinasa.
ES2395581T3 (es) *	2007-06-20	2013-02-13	Merck Sharp & Dohme Corp.	Inhibidores de quinasas janus
BRPI0813216A2 (pt) *	2007-06-21	2014-12-23	Irm Llc	Inibidores de proteínas cinases e métodos para usá-los.
TW200916468A (en)	2007-07-31	2009-04-16	Vertex Pharma	Process for preparing 5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-amine and derivatives thereof
DE102008015033A1 (de)	2008-03-17	2009-09-24	Aicuris Gmbh & Co. Kg	Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung
DE102008015032A1 (de)	2008-03-17	2009-09-24	Aicuris Gmbh & Co. Kg	Substituierte Pyrazolamide und ihre Verwendung
EP2288611B1 (en) *	2008-03-20	2013-05-15	Amgen Inc.	Aurora kinase modulators and method of use
US9126935B2 (en)	2008-08-14	2015-09-08	Amgen Inc.	Aurora kinase modulators and methods of use
EP2323622A1 (en) *	2008-09-03	2011-05-25	Vertex Pharmaceuticals Incorporated	Co-crystals and pharmaceutical formulations comprising the same
GB0820819D0 (en)	2008-11-13	2008-12-24	Sareum Ltd	Pharmaceutical compounds
ES2779001T3 (es)	2008-12-03	2020-08-13	Scripps Research Inst	Cultivos de células madre
DE102008062863A1 (de)	2008-12-17	2010-06-24	Aicuris Gmbh & Co. Kg	Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung
DE102008062878A1 (de)	2008-12-17	2010-06-24	Aicuris Gmbh & Co. Kg	Substituierte Furancarboxamide und ihre Verwendung
TW202241853A (zh)	2009-01-16	2022-11-01	美商艾克塞里克斯公司	包含n-(4-{[6,7-雙(甲氧基)喹啉-4-基]氧基}苯基)-n'-(4-氟苯基)環丙烷-1,1-二甲醯胺之蘋果酸鹽之醫藥組合物及其用途
PT2396307E (pt) *	2009-02-11	2015-02-04	Merck Patent Gmbh	Novas carboxamidas azaheterocíclicas de amino
UA108618C2 (uk)	2009-08-07	2015-05-25		Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку
WO2011041198A1 (en)	2009-09-30	2011-04-07	Transtech Pharma, Inc.	Substituted imidazole derivatives for treatment of alzheimers disease
CN102971313A (zh)	2010-04-14	2013-03-13	百时美施贵宝公司	新颖的葡糖激酶激活剂及其使用方法
US9090633B2 (en)	2010-11-18	2015-07-28	Kasina Laila Innova Pharmaceuticals Private Limited	Substituted 4-(arylamino) selenophenopyrimidine compounds and methods of use thereof
JP5898687B2 (ja) *	2010-11-18	2016-04-06	カシナライライノバファーマシューティカルズプライベートリミテッド	置換４−（セレノフェン−２（または３）−イルアミノ）ピリミジン化合物およびその使用方法
US8785459B2 (en) *	2011-12-27	2014-07-22	Development Center For Biotechnology	Quinazoline compounds as kinase inhibitors
GB201202027D0 (en)	2012-02-06	2012-03-21	Sareum Ltd	Pharmaceutical compounds
ES2566205T3 (es)	2012-03-02	2016-04-11	Sareum Limited	Inhibidores de quinasa TYK2
CN103788085B (zh) *	2012-10-31	2016-09-07	复旦大学	2-（喹唑啉-4-氨基）-5-噻唑甲酰胺类衍生物及其生物药物用途
CN104098551B (zh) *	2013-04-03	2019-03-22	广东东阳光药业有限公司	作为欧若拉激酶抑制剂的取代喹唑啉类衍生物
HUE048498T2 (hu)	2013-09-16	2020-07-28	Astrazeneca Ab	Terápiás polimer nanorészecskék és eljárások elõállításukra és alkalmazásukra
MX2018004109A (es)	2015-10-05	2018-09-27	Univ Columbia	Activadores de flujo autofágico y fosfolipasa d y depuración de acumulaciones de proteína que incluyen tau y tratamiento de proteinopatías.
GB201617871D0 (en)	2016-10-21	2016-12-07	Sareum Limited	Pharmaceutical compounds
AR112027A1 (es) *	2017-06-15	2019-09-11	Biocryst Pharm Inc	Inhibidores de alk 2 quinasa que contienen imidazol
EP4025565A1 (en) *	2019-09-06	2022-07-13	Inflazome Limited	Nlrp3 inhibitors
CN110746398A (zh) *	2019-10-18	2020-02-04	刘沛友	4-杂环取代喹唑啉类衍生物及其制备方法和用途
CN111574473A (zh) *	2020-06-04	2020-08-25	宁夏农林科学院农业资源与环境研究所（宁夏土壤与植物营养重点实验室）	一种氨基噻唑类化合物的合成方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3870725A (en) *	1971-03-30	1975-03-11	Lilly Industries Ltd	Nitrothiazole derivatives
US5710158A (en) *	1991-05-10	1998-01-20	Rhone-Poulenc Rorer Pharmaceuticals Inc.	Aryl and heteroaryl quinazoline compounds which inhibit EGF and/or PDGF receptor tyrosine kinase
ES2108120T3 (es)	1991-05-10	1997-12-16	Rhone Poulenc Rorer Int	Compuestos bis arilicos y heteroarilicos mono- y biciclicos que inhiben tirosina quinasa receptora de egf y/o pdgf.
NZ243082A (en) *	1991-06-28	1995-02-24	Ici Plc	4-anilino-quinazoline derivatives; pharmaceutical compositions, preparatory processes, and use thereof
IL117620A0 (en) *	1995-03-27	1996-07-23	Fujisawa Pharmaceutical Co	Heterocyclic compounds processes for the preparation thereof and pharmaceutical compositions containing the same
GB9514265D0 (en)	1995-07-13	1995-09-13	Wellcome Found	Hetrocyclic compounds
US6716575B2 (en) *	1995-12-18	2004-04-06	Sugen, Inc.	Diagnosis and treatment of AUR1 and/or AUR2 related disorders
TW436485B (en)	1997-08-01	2001-05-28	American Cyanamid Co	Substituted quinazoline derivatives
GB9800569D0 (en)	1998-01-12	1998-03-11	Glaxo Group Ltd	Heterocyclic compounds
GB9800575D0 (en)	1998-01-12	1998-03-11	Glaxo Group Ltd	Heterocyclic compounds
BR9914326A (pt) *	1998-10-08	2001-06-26	Astrazeneca Ab	Uso de um composto, composto, processo para a preparação do mesmo, composição farmacêutica, e, método para produzir um efeito antiangiogênico e/ou de redução da permeabilidade vascular em animais de sangue quente em necessidade de um tal tratamento
GB9922171D0 (en)	1999-09-21	1999-11-17	Zeneca Ltd	Chemical compounds

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113311166A (zh) *	2021-04-28	2021-08-27	新疆农垦科学院	一种用于绵羊早期妊娠诊断的蛋白生物标志物及其用于绵羊早期妊娠检测的方法
CN113311166B (zh) *	2021-04-28	2022-10-28	新疆农垦科学院	一种用于绵羊早期妊娠诊断的蛋白生物标志物及其用于绵羊早期妊娠检测的方法
CN115557601A (zh) *	2022-11-08	2023-01-03	成都理工大学	生物质微球及其制备方法与应用、生物反应器、地下井

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JP2004501914A (ja)	2004-01-22
EP1299381A1 (en)	2003-04-09
ES2305081T3 (es)	2008-11-01
US20060046987A1 (en)	2006-03-02
SK18102002A3 (sk)	2003-07-01
CN1267431C (zh)	2006-08-02
PL360439A1 (en)	2004-09-06
ATE394102T1 (de)	2008-05-15
MXPA02011974A (es)	2004-09-06
AR030432A1 (es)	2003-08-20
NO20026010L (no)	2002-12-13
IL153246A0 (en)	2003-07-06
EE200200715A (et)	2004-08-16
KR20030014411A (ko)	2003-02-17
IS6656A (is)	2002-12-17
CN1496364A (zh)	2004-05-12
BG107376A (bg)	2003-09-30
DE60133897D1 (de)	2008-06-19
WO2002000649A9 (en)	2007-09-20
RU2283311C2 (ru)	2006-09-10
NO20026010D0 (no)	2002-12-13
CA2412592A1 (en)	2002-01-03
US6919338B2 (en)	2005-07-19
BR0111754A (pt)	2003-04-29
HUP0301236A2 (hu)	2003-10-28
NZ522696A (en)	2004-08-27
US20030187002A1 (en)	2003-10-02
WO2002000649A1 (en)	2002-01-03
ZA200209412B (en)	2004-02-19
CZ20024120A3 (cs)	2003-03-12
EP1299381B1 (en)	2008-05-07
HK1053124A1 (en)	2003-10-10

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Publication	Publication Date	Title
US6919338B2 (en)	2005-07-19	Substituted quinazoline derivatives and their use as inhibitors of aurora-2 kinase
US7402585B2 (en)	2008-07-22	Substituted quinazoline derivatives as inhibitors of aurora kinases
US7105669B1 (en)	2006-09-12	Quinazoline derivatives
US7081461B1 (en)	2006-07-25	Quinazoline compounds and pharmaceutical compositions containing them
US7709479B1 (en)	2010-05-04	Quinazoline derivatives and their use as pharmaceuticals
US7235559B1 (en)	2007-06-26	Therapeutic quinazoline derivatives
US6977259B2 (en)	2005-12-20	Quinoline derivatives and their use as aurora 2 kinase inhibitors
JP4619545B2 (ja)	2011-01-26	アミド誘導体