JP2009541472A5 - - Google Patents
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- Publication number
- JP2009541472A5 JP2009541472A5 JP2009517333A JP2009517333A JP2009541472A5 JP 2009541472 A5 JP2009541472 A5 JP 2009541472A5 JP 2009517333 A JP2009517333 A JP 2009517333A JP 2009517333 A JP2009517333 A JP 2009517333A JP 2009541472 A5 JP2009541472 A5 JP 2009541472A5
- Authority
- JP
- Japan
- Prior art keywords
- benzimidazol
- pyrazol
- fluoro
- dimethylaminopropoxy
- carboxamide
- 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
- 150000001875 compounds Chemical class 0.000 claims 7
- 230000001575 pathological effect Effects 0.000 claims 3
- XCKMPQWPGHTSHA-UHFFFAOYSA-N 3-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(OCCCN(C)C)C=C2N1 XCKMPQWPGHTSHA-UHFFFAOYSA-N 0.000 claims 2
- -1 3-dimethylaminopropoxy Chemical group 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- OSTWUCPGWNUYLO-UHFFFAOYSA-N 1,1-diethyl-3-[5-(6-fluoro-5-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCOCC3)C=C2N1 OSTWUCPGWNUYLO-UHFFFAOYSA-N 0.000 claims 1
- NVGCPDIVOAKBPS-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC=C(N3CCN(C)CC3)C=C2N1 NVGCPDIVOAKBPS-UHFFFAOYSA-N 0.000 claims 1
- ASZIJOOHZRHJNK-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-fluoro-5-(1,4-oxazepan-4-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCOCCC3)C=C2N1 ASZIJOOHZRHJNK-UHFFFAOYSA-N 0.000 claims 1
- FERRVYZKCLDYEV-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-fluoro-5-(2-piperidin-1-ylethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C(NC1=C2)=NC1=CC(F)=C2OCCN1CCCCC1 FERRVYZKCLDYEV-UHFFFAOYSA-N 0.000 claims 1
- MFHOXGAPSGZOPI-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-fluoro-5-(3-piperidin-1-ylpropoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C(NC1=C2)=NC1=CC(F)=C2OCCCN1CCCCC1 MFHOXGAPSGZOPI-UHFFFAOYSA-N 0.000 claims 1
- KMIWCJXOWPZWQW-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-fluoro-5-(4-methyl-1,4-diazepan-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCN(C)CCC3)C=C2N1 KMIWCJXOWPZWQW-UHFFFAOYSA-N 0.000 claims 1
- HIBLDGCWJMGFGF-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCN(C)CC3)C=C2N1 HIBLDGCWJMGFGF-UHFFFAOYSA-N 0.000 claims 1
- YFJCJBDOYQIPMR-UHFFFAOYSA-N 1,1-diethyl-3-[5-[6-fluoro-5-(4-piperidin-1-ylbutoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(OCCCCN3CCCCC3)=C(F)C=C2N1 YFJCJBDOYQIPMR-UHFFFAOYSA-N 0.000 claims 1
- SFTHSXLQNNJPNX-UHFFFAOYSA-N 1-[2-[4-(diethylcarbamoylamino)-1H-pyrazol-5-yl]-6-fluoro-1H-benzimidazol-5-yl]-1-[2-(dimethylamino)ethyl]-3,3-diethylurea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N(CCN(C)C)C(=O)N(CC)CC)C=C2N1 SFTHSXLQNNJPNX-UHFFFAOYSA-N 0.000 claims 1
- FRUOEXNFTORCIN-UHFFFAOYSA-N 1-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-3-(2-methylpropyl)urea Chemical compound CC(C)CNC(=O)NC1=CNN=C1C1=NC2=CC(F)=C(OCCCN(C)C)C=C2N1 FRUOEXNFTORCIN-UHFFFAOYSA-N 0.000 claims 1
- VNKDRSCWWLVEOY-UHFFFAOYSA-N 1-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CNN=C1C1=NC2=CC(F)=C(OCCCN(C)C)C=C2N1 VNKDRSCWWLVEOY-UHFFFAOYSA-N 0.000 claims 1
- MGIXTLLEVJPYHL-UHFFFAOYSA-N 1-ethyl-3-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1-propan-2-ylurea Chemical compound CCN(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC=C(N3CCN(C)CC3)C=C2N1 MGIXTLLEVJPYHL-UHFFFAOYSA-N 0.000 claims 1
- YJJCNPLHAIFNBA-UHFFFAOYSA-N 1-tert-butyl-3-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]urea Chemical compound N=1C=2C=C(F)C(OCCCN(C)C)=CC=2NC=1C1=NNC=C1NC(=O)NC(C)(C)C YJJCNPLHAIFNBA-UHFFFAOYSA-N 0.000 claims 1
- FFULMMNPJPWFJR-UHFFFAOYSA-N 3-[5-(6-fluoro-5-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCOCC3)C=C2N1 FFULMMNPJPWFJR-UHFFFAOYSA-N 0.000 claims 1
- XNQAGURRHHSIBD-UHFFFAOYSA-N 3-[5-[5-[2-(dimethylamino)ethylamino]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(NCCN(C)C)C=C2N1 XNQAGURRHHSIBD-UHFFFAOYSA-N 0.000 claims 1
- XWTIGMNAGMTVIG-UHFFFAOYSA-N 3-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-diethylurea Chemical compound CCN(CC)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(OCCCN(C)C)C=C2N1 XWTIGMNAGMTVIG-UHFFFAOYSA-N 0.000 claims 1
- UHDSNMCLGVCVJB-UHFFFAOYSA-N 3-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1-ethyl-1-propan-2-ylurea Chemical compound CCN(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(OCCCN(C)C)C=C2N1 UHDSNMCLGVCVJB-UHFFFAOYSA-N 0.000 claims 1
- UODQGOVWZZQWBL-UHFFFAOYSA-N 3-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1-methyl-1-propan-2-ylurea Chemical compound CC(C)N(C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(OCCCN(C)C)C=C2N1 UODQGOVWZZQWBL-UHFFFAOYSA-N 0.000 claims 1
- UBZWLLVOWVRRNG-UHFFFAOYSA-N 3-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC=C(N3CCN(C)CC3)C=C2N1 UBZWLLVOWVRRNG-UHFFFAOYSA-N 0.000 claims 1
- FKMDEBOWVVGVIJ-UHFFFAOYSA-N 3-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-dipropylurea Chemical compound CCCN(CCC)C(=O)NC1=CNN=C1C1=NC2=CC=C(N3CCN(C)CC3)C=C2N1 FKMDEBOWVVGVIJ-UHFFFAOYSA-N 0.000 claims 1
- ZMCQTMWMGXKBGB-UHFFFAOYSA-N 3-[5-[6-fluoro-5-(1,4-oxazepan-4-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCOCCC3)C=C2N1 ZMCQTMWMGXKBGB-UHFFFAOYSA-N 0.000 claims 1
- WTSQSSVRCUMRJA-UHFFFAOYSA-N 3-[5-[6-fluoro-5-(4-methyl-1,4-diazepan-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCN(C)CCC3)C=C2N1 WTSQSSVRCUMRJA-UHFFFAOYSA-N 0.000 claims 1
- LQTBALSNANRJTA-UHFFFAOYSA-N 3-[5-[6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-1,1-di(propan-2-yl)urea Chemical compound CC(C)N(C(C)C)C(=O)NC1=CNN=C1C1=NC2=CC(F)=C(N3CCN(C)CC3)C=C2N1 LQTBALSNANRJTA-UHFFFAOYSA-N 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- PUCZMFSHQLOIAY-UHFFFAOYSA-N N-[5-(6-fluoro-5-morpholin-4-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound FC1=CC=2N=C(C=3C(=CNN=3)NC(=O)N3CCCCC3)NC=2C=C1N1CCOCC1 PUCZMFSHQLOIAY-UHFFFAOYSA-N 0.000 claims 1
- GGFYARGSOOPPQR-UHFFFAOYSA-N N-[5-(6-fluoro-5-piperazin-1-yl-1H-benzimidazol-2-yl)-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound FC1=CC=2N=C(C=3C(=CNN=3)NC(=O)N3CCCCC3)NC=2C=C1N1CCNCC1 GGFYARGSOOPPQR-UHFFFAOYSA-N 0.000 claims 1
- XIMOTJVCOAZUQA-UHFFFAOYSA-N N-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]-4-methylpiperazine-1-carboxamide Chemical compound N=1C=2C=C(F)C(OCCCN(C)C)=CC=2NC=1C1=NNC=C1NC(=O)N1CCN(C)CC1 XIMOTJVCOAZUQA-UHFFFAOYSA-N 0.000 claims 1
- GYJNYIGSUKEIMQ-UHFFFAOYSA-N N-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]morpholine-4-carboxamide Chemical compound N=1C=2C=C(F)C(OCCCN(C)C)=CC=2NC=1C1=NNC=C1NC(=O)N1CCOCC1 GYJNYIGSUKEIMQ-UHFFFAOYSA-N 0.000 claims 1
- GDWIAFXXYDJDTC-UHFFFAOYSA-N N-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperazine-1-carboxamide Chemical compound N=1C=2C=C(F)C(OCCCN(C)C)=CC=2NC=1C1=NNC=C1NC(=O)N1CCNCC1 GDWIAFXXYDJDTC-UHFFFAOYSA-N 0.000 claims 1
- VMHRLMMZHIERDA-UHFFFAOYSA-N N-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound N=1C=2C=C(F)C(OCCCN(C)C)=CC=2NC=1C1=NNC=C1NC(=O)N1CCCCC1 VMHRLMMZHIERDA-UHFFFAOYSA-N 0.000 claims 1
- JMUSXAFWWOYSKT-UHFFFAOYSA-N N-[5-[5-[3-(dimethylamino)propoxy]-6-fluoro-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]pyrrolidine-1-carboxamide Chemical compound N=1C=2C=C(F)C(OCCCN(C)C)=CC=2NC=1C1=NNC=C1NC(=O)N1CCCC1 JMUSXAFWWOYSKT-UHFFFAOYSA-N 0.000 claims 1
- OKTVPPCYTKFVOR-UHFFFAOYSA-N N-[5-[6-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound C1CN(C)CCN1C1=CC=C(N=C(N2)C=3C(=CNN=3)NC(=O)N3CCCCC3)C2=C1 OKTVPPCYTKFVOR-UHFFFAOYSA-N 0.000 claims 1
- IZBKJHMWZXCNRN-UHFFFAOYSA-N N-[5-[6-fluoro-5-(1,4-oxazepan-4-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound FC1=CC=2N=C(C=3C(=CNN=3)NC(=O)N3CCCCC3)NC=2C=C1N1CCCOCC1 IZBKJHMWZXCNRN-UHFFFAOYSA-N 0.000 claims 1
- OXZHIOCZAKEIIV-UHFFFAOYSA-N N-[5-[6-fluoro-5-(2-piperidin-1-ylethoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound FC1=CC=2N=C(C=3C(=CNN=3)NC(=O)N3CCCCC3)NC=2C=C1OCCN1CCCCC1 OXZHIOCZAKEIIV-UHFFFAOYSA-N 0.000 claims 1
- AYEUKIZPVXRWNW-UHFFFAOYSA-N N-[5-[6-fluoro-5-(4-methyl-1,4-diazepan-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound C1CN(C)CCCN1C(C(=C1)F)=CC2=C1N=C(C=1C(=CNN=1)NC(=O)N1CCCCC1)N2 AYEUKIZPVXRWNW-UHFFFAOYSA-N 0.000 claims 1
- ALBCTTSDFKXKJN-UHFFFAOYSA-N N-[5-[6-fluoro-5-(4-methylpiperazin-1-yl)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound C1CN(C)CCN1C(C(=C1)F)=CC2=C1N=C(C=1C(=CNN=1)NC(=O)N1CCCCC1)N2 ALBCTTSDFKXKJN-UHFFFAOYSA-N 0.000 claims 1
- RKJIQRQZDMUFAV-UHFFFAOYSA-N N-[5-[6-fluoro-5-(4-piperidin-1-ylbutoxy)-1H-benzimidazol-2-yl]-1H-pyrazol-4-yl]piperidine-1-carboxamide Chemical compound FC1=CC=2NC(C=3C(=CNN=3)NC(=O)N3CCCCC3)=NC=2C=C1OCCCCN1CCCCC1 RKJIQRQZDMUFAV-UHFFFAOYSA-N 0.000 claims 1
- 102000001253 Protein Kinase Human genes 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 239000004202 carbamide Substances 0.000 claims 1
- 230000006378 damage Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 208000032839 leukemia Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 108060006633 protein kinase Proteins 0.000 claims 1
- 239000012453 solvate Substances 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0606064A FR2903406B1 (fr) | 2006-07-04 | 2006-07-04 | Derives de pyrazolylbenzimidazole,compositions les contenant et utilisation |
| FR0606064 | 2006-07-04 | ||
| PCT/FR2007/001126 WO2008003857A1 (fr) | 2006-07-04 | 2007-07-03 | Derives de pyrazolylbenzimidazole, compositions les contenant et leur utilisation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009541472A JP2009541472A (ja) | 2009-11-26 |
| JP2009541472A5 true JP2009541472A5 (https=) | 2010-08-19 |
| JP5746821B2 JP5746821B2 (ja) | 2015-07-08 |
Family
ID=37670881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009517333A Expired - Fee Related JP5746821B2 (ja) | 2006-07-04 | 2007-07-03 | ピラゾリルベンゾイミダゾール誘導体、これらを含有する組成物及びこれらの使用 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US9126969B2 (https=) |
| EP (1) | EP2041119B1 (https=) |
| JP (1) | JP5746821B2 (https=) |
| FR (1) | FR2903406B1 (https=) |
| WO (1) | WO2008003857A1 (https=) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1968579A1 (en) | 2005-12-30 | 2008-09-17 | Astex Therapeutics Limited | Pharmaceutical compounds |
| EP2049119A2 (en) | 2006-06-29 | 2009-04-22 | Astex Therapeutics Limited | Pharmaceutical combinations of 1-cyclopropyl-3-[3-(5-morphoolin-4-ylmethyl-1h-benzoimidazol-2-yl)-1h-1-pyrazol-4-yl]-urea |
| PH12012500252A1 (en) | 2009-08-07 | 2015-06-26 | Chugai Pharmaceutical Co Ltd | Aminopyrazole derivative |
| CA2780031A1 (en) * | 2009-11-12 | 2011-05-19 | Selvita S.A. | A compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent |
| US8604217B2 (en) | 2009-11-12 | 2013-12-10 | Selvita S.A. | Compound, a process for its preparation, a pharmaceutical composition, use of a compound, a method for modulating or regulating serine/threonine kinases and a serine/threonine kinases modulating agent |
| JP6161537B2 (ja) | 2010-04-07 | 2017-07-12 | エフ・ホフマン−ラ・ロシュ・アクチェンゲゼルシャフト | ピラゾール−４−イル−ヘテロシクリル−カルボキサミド化合物及び使用の方法 |
| AR088061A1 (es) | 2011-09-27 | 2014-05-07 | Hoffmann La Roche | Compuestos de pirazol-4-il-heterociclil-carboxamida y metodos de uso |
| US10391081B2 (en) | 2013-12-27 | 2019-08-27 | Chugai Seiyaku Kabushiki Kaisha | FGFR gatekeeper mutant gene and drug targeting same |
| EP3312172B1 (en) | 2015-06-17 | 2020-05-06 | Chugai Seiyaku Kabushiki Kaisha | Aminopyrazole derivatives useful as src kinase inhibitors |
| WO2025040140A1 (en) * | 2023-08-22 | 2025-02-27 | National Institute Of Biological Sciences, Beijing | Substituted pyrazol-4-yl urea as kinase inhibitors |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2831536A1 (fr) | 2001-10-26 | 2003-05-02 | Aventis Pharma Sa | Nouveaux derives de benzimidazoles, leur procede de preparation, leur application a titre de medicament, compositions pharmaceutiques et nouvelle utilisation notamment comme inhibiteurs de kdr |
| JP5039268B2 (ja) * | 2001-10-26 | 2012-10-03 | アベンティス・ファーマスーティカルズ・インコーポレイテツド | ベンゾイミダゾールおよび類縁体および蛋白キナーゼ阻害剤としてのその使用 |
| US6897208B2 (en) | 2001-10-26 | 2005-05-24 | Aventis Pharmaceuticals Inc. | Benzimidazoles |
| TWI372050B (en) * | 2003-07-03 | 2012-09-11 | Astex Therapeutics Ltd | (morpholin-4-ylmethyl-1h-benzimidazol-2-yl)-1h-pyrazoles |
| WO2006070202A1 (en) | 2004-12-30 | 2006-07-06 | Astex Therapeutics Limited | Pyrazole derivatives having kinase modulating activity |
| EP2049119A2 (en) * | 2006-06-29 | 2009-04-22 | Astex Therapeutics Limited | Pharmaceutical combinations of 1-cyclopropyl-3-[3-(5-morphoolin-4-ylmethyl-1h-benzoimidazol-2-yl)-1h-1-pyrazol-4-yl]-urea |
-
2006
- 2006-07-04 FR FR0606064A patent/FR2903406B1/fr active Active
-
2007
- 2007-07-03 EP EP07803834.6A patent/EP2041119B1/fr active Active
- 2007-07-03 JP JP2009517333A patent/JP5746821B2/ja not_active Expired - Fee Related
- 2007-07-03 WO PCT/FR2007/001126 patent/WO2008003857A1/fr not_active Ceased
-
2008
- 2008-12-18 US US12/338,176 patent/US9126969B2/en not_active Expired - Fee Related
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