JP2015528508A5 - - Google Patents
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- Publication number
- JP2015528508A5 JP2015528508A5 JP2015532064A JP2015532064A JP2015528508A5 JP 2015528508 A5 JP2015528508 A5 JP 2015528508A5 JP 2015532064 A JP2015532064 A JP 2015532064A JP 2015532064 A JP2015532064 A JP 2015532064A JP 2015528508 A5 JP2015528508 A5 JP 2015528508A5
- Authority
- JP
- Japan
- Prior art keywords
- pyrazol
- dimethyl
- alkoxy
- amine
- quinolin
- Prior art date
- 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.)
- Granted
Links
- 150000003839 salts Chemical class 0.000 claims 12
- 150000001875 compounds Chemical class 0.000 claims 11
- -1 cyano, hydroxyl Chemical group 0.000 claims 11
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 4
- QODPGRHWJBWTJC-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-(2-methoxyethoxy)quinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OCCOC)=CC2=NC=CC=1NC1=NNC(C)=C1C QODPGRHWJBWTJC-UHFFFAOYSA-N 0.000 claims 3
- 208000009766 Blau syndrome Diseases 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001153 fluoro group Chemical group F* 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 2
- BFDDPFRPBQXQBX-GFCCVEGCSA-N (2r)-1-[6-tert-butylsulfonyl-4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]quinolin-7-yl]oxypropan-2-ol Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OC[C@H](O)C)=CC2=NC=CC=1NC1=NNC(C)=C1C BFDDPFRPBQXQBX-GFCCVEGCSA-N 0.000 claims 1
- BFDDPFRPBQXQBX-LBPRGKRZSA-N (2s)-1-[6-tert-butylsulfonyl-4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]quinolin-7-yl]oxypropan-2-ol Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OC[C@@H](O)C)=CC2=NC=CC=1NC1=NNC(C)=C1C BFDDPFRPBQXQBX-LBPRGKRZSA-N 0.000 claims 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- HOTBTVYQQMHEBB-UHFFFAOYSA-N 1-[6-tert-butylsulfonyl-4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]quinolin-7-yl]oxy-2-methylpropan-2-ol Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(OCC(C)(C)O)=C(S(=O)(=O)C(C)(C)C)C=C12 HOTBTVYQQMHEBB-UHFFFAOYSA-N 0.000 claims 1
- HZDJLSITORIPGT-UHFFFAOYSA-N 2-[4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]-7-methoxyquinolin-6-yl]sulfonyl-2-methylpropan-1-ol Chemical compound C=12C=C(S(=O)(=O)C(C)(C)CO)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C HZDJLSITORIPGT-UHFFFAOYSA-N 0.000 claims 1
- LSTLSXLHIRBYFQ-UHFFFAOYSA-N 2-[4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]-7-methoxyquinolin-6-yl]sulfonylethanol Chemical compound C=12C=C(S(=O)(=O)CCO)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C LSTLSXLHIRBYFQ-UHFFFAOYSA-N 0.000 claims 1
- HRBKEPLXBIHJME-UHFFFAOYSA-N 2-[6-tert-butylsulfonyl-4-[(4,5-dimethyl-1h-pyrazol-3-yl)amino]quinolin-7-yl]oxyethanol Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(OCCO)=C(S(=O)(=O)C(C)(C)C)C=C12 HRBKEPLXBIHJME-UHFFFAOYSA-N 0.000 claims 1
- OVPZGUMHWDAVSH-UHFFFAOYSA-N 6-(2,2-dimethyloxan-4-yl)sulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxyquinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C3CC(C)(C)OCC3)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C OVPZGUMHWDAVSH-UHFFFAOYSA-N 0.000 claims 1
- SHJUBFAKVSHFJQ-OCZCAGDBSA-N 6-[(2r,6s)-2,6-dimethyloxan-4-yl]sulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxyquinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C3C[C@@H](C)O[C@@H](C)C3)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C SHJUBFAKVSHFJQ-OCZCAGDBSA-N 0.000 claims 1
- QWECBUNTPLWDBL-UHFFFAOYSA-N 6-tert-butylsulfonyl-4-[(4,5-dimethyl-1H-pyrazol-3-yl)amino]quinolin-7-ol Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(O)=C(S(=O)(=O)C(C)(C)C)C=C12 QWECBUNTPLWDBL-UHFFFAOYSA-N 0.000 claims 1
- PLYPDBCKMUBDTF-UHFFFAOYSA-N 6-tert-butylsulfonyl-7-(2,2-difluoroethoxy)-n-(4,5-dimethyl-1h-pyrazol-3-yl)quinolin-4-amine Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(OCC(F)F)=C(S(=O)(=O)C(C)(C)C)C=C12 PLYPDBCKMUBDTF-UHFFFAOYSA-N 0.000 claims 1
- DPILGXGHKJEOAS-UHFFFAOYSA-N 6-tert-butylsulfonyl-7-(difluoromethoxy)-n-(4,5-dimethyl-1h-pyrazol-3-yl)quinolin-4-amine Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(OC(F)F)=C(S(=O)(=O)C(C)(C)C)C=C12 DPILGXGHKJEOAS-UHFFFAOYSA-N 0.000 claims 1
- DPSNWHXNCQBYAH-UHFFFAOYSA-N 6-tert-butylsulfonyl-7-methoxy-n-[4-methyl-5-(trifluoromethyl)-1h-pyrazol-3-yl]quinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OC)=CC2=NC=CC=1NC1=NNC(C(F)(F)F)=C1C DPSNWHXNCQBYAH-UHFFFAOYSA-N 0.000 claims 1
- LSBUSOIHRLJSJM-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-(2,2,2-trifluoroethoxy)quinolin-4-amine Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(OCC(F)(F)F)=C(S(=O)(=O)C(C)(C)C)C=C12 LSBUSOIHRLJSJM-UHFFFAOYSA-N 0.000 claims 1
- VENUDGUYMCDYAB-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-(3-methoxypropoxy)quinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OCCCOC)=CC2=NC=CC=1NC1=NNC(C)=C1C VENUDGUYMCDYAB-UHFFFAOYSA-N 0.000 claims 1
- UVCJVWDOTPZNJM-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-ethoxyquinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OCC)=CC2=NC=CC=1NC1=NNC(C)=C1C UVCJVWDOTPZNJM-UHFFFAOYSA-N 0.000 claims 1
- SNLKRSSBDMHRFL-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-fluoroquinolin-4-amine Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(F)=C(S(=O)(=O)C(C)(C)C)C=C12 SNLKRSSBDMHRFL-UHFFFAOYSA-N 0.000 claims 1
- LHPFRDAGGDMRMZ-UHFFFAOYSA-N 6-tert-butylsulfonyl-n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxyquinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)(C)C)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C LHPFRDAGGDMRMZ-UHFFFAOYSA-N 0.000 claims 1
- SVARURAGDUBTCW-UHFFFAOYSA-N 7-(difluoromethoxy)-n-(4,5-dimethyl-1h-pyrazol-3-yl)-6-(oxan-4-ylsulfonyl)quinolin-4-amine Chemical compound CC1=C(C)NN=C1NC1=CC=NC2=CC(OC(F)F)=C(S(=O)(=O)C3CCOCC3)C=C12 SVARURAGDUBTCW-UHFFFAOYSA-N 0.000 claims 1
- GMWIWJMSCHALJV-UHFFFAOYSA-N 7-methoxy-n-[4-methyl-5-(trifluoromethyl)-1h-pyrazol-3-yl]-6-(oxan-4-ylsulfonyl)quinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C3CCOCC3)C(OC)=CC2=NC=CC=1NC1=NNC(C(F)(F)F)=C1C GMWIWJMSCHALJV-UHFFFAOYSA-N 0.000 claims 1
- LHUXIXHXMCIUBN-UHFFFAOYSA-N 7-methoxy-n-[4-methyl-5-(trifluoromethyl)-1h-pyrazol-3-yl]-6-propan-2-ylsulfonylquinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C(C)C)C(OC)=CC2=NC=CC=1NC1=NNC(C(F)(F)F)=C1C LHUXIXHXMCIUBN-UHFFFAOYSA-N 0.000 claims 1
- 208000007082 Alcoholic Fatty Liver Diseases 0.000 claims 1
- 206010003827 Autoimmune hepatitis Diseases 0.000 claims 1
- 108090000426 Caspase-1 Proteins 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 101001109137 Homo sapiens Receptor-interacting serine/threonine-protein kinase 2 Proteins 0.000 claims 1
- 208000029523 Interstitial Lung disease Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 102100022502 Receptor-interacting serine/threonine-protein kinase 2 Human genes 0.000 claims 1
- 206010063837 Reperfusion injury Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010069351 acute lung injury Diseases 0.000 claims 1
- 208000026594 alcoholic fatty liver disease Diseases 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- UTGFZERHPKWOOY-UHFFFAOYSA-N n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxy-6-(2-methoxyethylsulfonyl)quinolin-4-amine Chemical compound C1=CN=C2C=C(OC)C(S(=O)(=O)CCOC)=CC2=C1NC1=NNC(C)=C1C UTGFZERHPKWOOY-UHFFFAOYSA-N 0.000 claims 1
- GTRTXSSFSXXYFL-UHFFFAOYSA-N n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxy-6-(4-methyloxan-4-yl)sulfonylquinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C3(C)CCOCC3)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C GTRTXSSFSXXYFL-UHFFFAOYSA-N 0.000 claims 1
- CXRQMMOWWNSBTM-UHFFFAOYSA-N n-(4,5-dimethyl-1h-pyrazol-3-yl)-7-methoxy-6-(oxan-4-ylsulfonyl)quinolin-4-amine Chemical compound C=12C=C(S(=O)(=O)C3CCOCC3)C(OC)=CC2=NC=CC=1NC1=NNC(C)=C1C CXRQMMOWWNSBTM-UHFFFAOYSA-N 0.000 claims 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
- 210000000056 organ Anatomy 0.000 claims 1
- VLCMRTMCMQJSKM-UHFFFAOYSA-N phenyl-[4-phenyl-8-(trifluoromethyl)quinolin-3-yl]methanone Chemical compound C=1C=CC=CC=1C(=O)C1=CN=C2C(C(F)(F)F)=CC=CC2=C1C1=CC=CC=C1 VLCMRTMCMQJSKM-UHFFFAOYSA-N 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 238000002054 transplantation Methods 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261700536P | 2012-09-13 | 2012-09-13 | |
| US61/700,536 | 2012-09-13 | ||
| US201361767378P | 2013-02-21 | 2013-02-21 | |
| US61/767,378 | 2013-02-21 | ||
| PCT/US2013/059600 WO2014043437A1 (en) | 2012-09-13 | 2013-09-13 | Amino-quinolines as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015528508A JP2015528508A (ja) | 2015-09-28 |
| JP2015528508A5 true JP2015528508A5 (enExample) | 2016-07-14 |
| JP6258331B2 JP6258331B2 (ja) | 2018-01-10 |
Family
ID=50278701
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015532064A Expired - Fee Related JP6258331B2 (ja) | 2012-09-13 | 2013-09-13 | キナーゼ阻害剤としてのアミノ−キノリン |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US9216965B2 (enExample) |
| EP (1) | EP2895167B1 (enExample) |
| JP (1) | JP6258331B2 (enExample) |
| KR (1) | KR20150053920A (enExample) |
| CN (1) | CN104602692B (enExample) |
| AR (1) | AR092530A1 (enExample) |
| AU (1) | AU2013315387B2 (enExample) |
| BR (1) | BR112015004967A2 (enExample) |
| CA (1) | CA2883155A1 (enExample) |
| CL (1) | CL2015000615A1 (enExample) |
| CR (1) | CR20150133A (enExample) |
| DO (1) | DOP2015000059A (enExample) |
| EA (1) | EA027984B1 (enExample) |
| ES (1) | ES2713172T3 (enExample) |
| IL (1) | IL237158A0 (enExample) |
| MX (1) | MX2015003275A (enExample) |
| PE (1) | PE20150774A1 (enExample) |
| PH (1) | PH12015500345A1 (enExample) |
| SG (1) | SG11201500973WA (enExample) |
| TW (1) | TW201425307A (enExample) |
| WO (1) | WO2014043437A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UY33549A (es) * | 2010-08-10 | 2012-01-31 | Glaxo Group Ltd | Quinolil aminas como agentes inhibidores de las quinasas |
| CA2829131C (en) | 2011-03-04 | 2018-11-20 | Glaxosmithkline Intellectual Property (No.2) Limited | Amino-quinolines as kinase inhibitors |
| TWI547494B (zh) | 2011-08-18 | 2016-09-01 | 葛蘭素史克智慧財產發展有限公司 | 作為激酶抑制劑之胺基喹唑啉類 |
| TW201425307A (zh) | 2012-09-13 | 2014-07-01 | Glaxosmithkline Llc | 作為激酶抑制劑之胺基－喹啉類 |
| TWI592417B (zh) | 2012-09-13 | 2017-07-21 | 葛蘭素史克智慧財產發展有限公司 | 胺基喹唑啉激酶抑制劑之前藥 |
| WO2014128622A1 (en) | 2013-02-21 | 2014-08-28 | Glaxosmithkline Intellectual Property Development Limited | Quinazolines as kinase inhibitors |
| GB201506872D0 (en) | 2015-04-22 | 2015-06-03 | Ge Oil & Gas Uk Ltd | Novel compounds |
| GB201516243D0 (en) | 2015-09-14 | 2015-10-28 | Glaxosmithkline Ip Dev Ltd | Novel compounds |
| CA3000988A1 (en) | 2015-10-05 | 2017-04-13 | The Trustees Of Columbia University In The City Of New York | Activators of autophagic flux and phospholipase d and clearance of protein aggregates including tau and treatment of proteinopathies |
| CN107158385B (zh) * | 2016-03-14 | 2020-07-14 | 苏州大学 | Rip3抑制剂在制备抗血小板血栓药物中的用途 |
| KR20180135038A (ko) | 2016-04-20 | 2018-12-19 | 글락소스미스클라인 인털렉츄얼 프로퍼티 디벨로프먼트 리미티드 | Ripk2 억제제를 포함하는 컨쥬게이트 |
| WO2020094613A1 (en) | 2018-11-06 | 2020-05-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Nod2 inhibitors for the treatment of hereditary periodic fevers |
| CN114014890A (zh) * | 2021-03-12 | 2022-02-08 | 爱科诺生物医药(香港)有限公司 | 具有rip2激酶抑制活性的化合物，包含其的药物组合物，及其应用 |
| WO2025078493A1 (en) | 2023-10-11 | 2025-04-17 | Institut National de la Santé et de la Recherche Médicale | Local administration of ripk2 inhibitors for the curative treatment of allergic asthma |
Family Cites Families (73)
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| US4916135A (en) | 1989-05-08 | 1990-04-10 | Hoechst Roussel Pharmaceuticals Inc. | N-heteroaryl-4-quinolinamines |
| 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 |
| AU661533B2 (en) | 1992-01-20 | 1995-07-27 | Astrazeneca Ab | Quinazoline derivatives |
| GB9510757D0 (en) | 1994-09-19 | 1995-07-19 | Wellcome Found | Therapeuticaly active compounds |
| US6046206A (en) | 1995-06-07 | 2000-04-04 | Cell Pathways, Inc. | Method of treating a patient having a precancerous lesions with amide quinazoline derivatives |
| ES2186908T3 (es) | 1996-07-13 | 2003-05-16 | Glaxo Group Ltd | Compuestos heterociciclos condensados como inhibidores de pproteina-tirosina-quinasas. |
| AU3969697A (en) | 1996-08-01 | 1998-02-25 | Dow Agrosciences Llc | Quinolinium derivatives having fungicidal activity |
| NZ334125A (en) | 1996-09-25 | 2000-10-27 | Zeneca Ltd | Quinoline derivatives inhibiting the effect of growth factors such as VEGF |
| UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
| CA2341374A1 (en) | 1998-10-01 | 2000-04-13 | Astrazeneca Ab | Quinoline and quinazoline derivatives and their use as inhibitors of cytokine mediated diseases |
| GB2345486A (en) | 1999-01-11 | 2000-07-12 | Glaxo Group Ltd | Heteroaromatic protein tyrosine kinase inhibitors |
| WO2001021596A1 (en) | 1999-09-21 | 2001-03-29 | Astrazeneca Ab | Quinazoline derivatives and their use as pharmaceuticals |
| AU2001228638A1 (en) | 2000-01-28 | 2001-08-07 | Astrazeneca Ab | Chemical compounds |
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| US6521618B2 (en) | 2000-03-28 | 2003-02-18 | Wyeth | 3-cyanoquinolines, 3-cyano-1,6-naphthyridines, and 3-cyano-1,7-naphthyridines as protein kinase inhibitors |
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| BR0113056A (pt) | 2000-08-09 | 2003-07-08 | Astrazeneca Ab | Composto, processo papa a preparação do mesmo, composição farmacêutica, e, método para produzir um efeito antiangiogênico e/ou redutor da permeabilidade vascular em um animal de sangue quente, e, uso de um composto |
| GB0104422D0 (en) | 2001-02-22 | 2001-04-11 | Glaxo Group Ltd | Quinoline derivative |
| SE0101675D0 (sv) | 2001-05-11 | 2001-05-11 | Astrazeneca Ab | Novel composition |
| US7115617B2 (en) | 2001-08-22 | 2006-10-03 | Amgen Inc. | Amino-substituted pyrimidinyl derivatives and methods of use |
| WO2003026664A1 (en) | 2001-09-26 | 2003-04-03 | Bayer Corporation | 2-phenylamino-4- (5-pyrazolylamino) -pyramidine derivatives as kinase inhibitors, in particular, src kinase inhibitors |
| US7402585B2 (en) | 2001-12-24 | 2008-07-22 | Astrazeneca Ab | Substituted quinazoline derivatives as inhibitors of aurora kinases |
| TWI275390B (en) * | 2002-04-30 | 2007-03-11 | Wyeth Corp | Process for the preparation of 7-substituted-3- quinolinecarbonitriles |
| US7262200B2 (en) | 2002-10-25 | 2007-08-28 | Vertex Pharmaceuticals Incorporated | Indazolinone compositions useful as kinase inhibitors |
| US20040122161A1 (en) | 2002-12-21 | 2004-06-24 | Paul Charles W. | Hot melt adhesive based on acrylic block copolymers |
| ATE438644T1 (de) | 2002-12-24 | 2009-08-15 | Astrazeneca Ab | Chinazolinderivate |
| TWI328009B (en) | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| BRPI0410720A (pt) | 2003-05-27 | 2006-06-20 | Pfizer Prod Inc | quinazolinas e pirido[3,4-d]pirimidinas como inibidores do receptor de tirosina cinase |
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-
2013
- 2013-09-11 TW TW102132714A patent/TW201425307A/zh unknown
- 2013-09-11 AR ARP130103248A patent/AR092530A1/es unknown
- 2013-09-13 SG SG11201500973WA patent/SG11201500973WA/en unknown
- 2013-09-13 ES ES13836616T patent/ES2713172T3/es active Active
- 2013-09-13 JP JP2015532064A patent/JP6258331B2/ja not_active Expired - Fee Related
- 2013-09-13 EP EP13836616.6A patent/EP2895167B1/en active Active
- 2013-09-13 AU AU2013315387A patent/AU2013315387B2/en not_active Ceased
- 2013-09-13 US US14/396,559 patent/US9216965B2/en not_active Expired - Fee Related
- 2013-09-13 MX MX2015003275A patent/MX2015003275A/es unknown
- 2013-09-13 WO PCT/US2013/059600 patent/WO2014043437A1/en not_active Ceased
- 2013-09-13 BR BR112015004967A patent/BR112015004967A2/pt active Search and Examination
- 2013-09-13 CA CA2883155A patent/CA2883155A1/en not_active Abandoned
- 2013-09-13 PE PE2015000276A patent/PE20150774A1/es not_active Application Discontinuation
- 2013-09-13 KR KR1020157006177A patent/KR20150053920A/ko not_active Withdrawn
- 2013-09-13 EA EA201590552A patent/EA027984B1/ru not_active IP Right Cessation
- 2013-09-13 CN CN201380045559.XA patent/CN104602692B/zh not_active Expired - Fee Related
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2015
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- 2015-02-17 PH PH12015500345A patent/PH12015500345A1/en unknown
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- 2015-03-13 DO DO2015000059A patent/DOP2015000059A/es unknown
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