JP2011509302A5 - - Google Patents
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- JP2011509302A5 JP2011509302A5 JP2010542343A JP2010542343A JP2011509302A5 JP 2011509302 A5 JP2011509302 A5 JP 2011509302A5 JP 2010542343 A JP2010542343 A JP 2010542343A JP 2010542343 A JP2010542343 A JP 2010542343A JP 2011509302 A5 JP2011509302 A5 JP 2011509302A5
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- JP
- Japan
- Prior art keywords
- compound according
- hydrogen
- compound
- alkyl
- optionally substituted
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 139
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 66
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 13
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 6
- -1 3-fluorophenoxy Chemical group 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 5
- 101000777293 Homo sapiens Serine/threonine-protein kinase Chk1 Proteins 0.000 claims description 4
- 101000777277 Homo sapiens Serine/threonine-protein kinase Chk2 Proteins 0.000 claims description 4
- 102100031081 Serine/threonine-protein kinase Chk1 Human genes 0.000 claims description 4
- 102100031075 Serine/threonine-protein kinase Chk2 Human genes 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 206010028980 Neoplasm Diseases 0.000 claims description 3
- 201000011510 cancer Diseases 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 230000001093 anti-cancer Effects 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000003112 inhibitor Substances 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
- 238000011275 oncology therapy Methods 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- 229920002554 vinyl polymer Polymers 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 description 24
- 0 C*(*)C*(C)C(C)(*)C(N(CCN(c1c(*)cnc2c1c(*)n[n]2)I)I)=O Chemical compound C*(*)C*(C)C(C)(*)C(N(CCN(c1c(*)cnc2c1c(*)n[n]2)I)I)=O 0.000 description 18
- 241000124008 Mammalia Species 0.000 description 4
- SRUBQVFBUPNJPS-UIOOFZCWSA-N CC(C)(CC1)N[C@@H]1[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl Chemical compound CC(C)(CC1)N[C@@H]1[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl SRUBQVFBUPNJPS-UIOOFZCWSA-N 0.000 description 1
- FKPBPDTXHICJSN-XMMPIXPASA-N CC(C)NCC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1cccc(F)c1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NCC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1cccc(F)c1)=O)c(cc1)ccc1Cl FKPBPDTXHICJSN-XMMPIXPASA-N 0.000 description 1
- KGZLISZNHMDDIA-XMMPIXPASA-N CC(C)NC[C@@H](C(N(CC1)CCN1c(c(c(OC)n[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c(c(c(OC)n[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl KGZLISZNHMDDIA-XMMPIXPASA-N 0.000 description 1
- XSEBVQYOKBAUMZ-XMMPIXPASA-N CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1)=O)c(cc1)ccc1Cl XSEBVQYOKBAUMZ-XMMPIXPASA-N 0.000 description 1
- KWRPNMQGGUOVAY-LJQANCHMSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1C#N)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1C#N)=O)c(cc1)ccc1Cl KWRPNMQGGUOVAY-LJQANCHMSA-N 0.000 description 1
- KCGMPJYIKCDNNU-QGZVFWFLSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c1c(C(F)(F)F)cnc2c1cn[nH]2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c1c(C(F)(F)F)cnc2c1cn[nH]2)=O)c(cc1)ccc1Cl KCGMPJYIKCDNNU-QGZVFWFLSA-N 0.000 description 1
- VFQMWGVFLLUWME-GFOWMXPYSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O)c(cc1)ccc1Cl VFQMWGVFLLUWME-GFOWMXPYSA-N 0.000 description 1
- HUYJXXMOMIZURM-LJQANCHMSA-N CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCCO)n[nH]2)=O)c(cc1)ccc1Cl Chemical compound CC(C)NC[C@@H](C(N(CC1)CCN1c1ccnc2c1c(OCCO)n[nH]2)=O)c(cc1)ccc1Cl HUYJXXMOMIZURM-LJQANCHMSA-N 0.000 description 1
- PORMJORUFSXADA-OAQYLSRUSA-N COc1n[nH]c(nc2)c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)c2-c1ccccc1 Chemical compound COc1n[nH]c(nc2)c1c(N(CC1)CCN1C([C@@H](Cc(cc1)ccc1Cl)N)=O)c2-c1ccccc1 PORMJORUFSXADA-OAQYLSRUSA-N 0.000 description 1
- WMBVNAHBGYIBMM-MRXNPFEDSA-N N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1Br)=O Chemical compound N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1Br)=O WMBVNAHBGYIBMM-MRXNPFEDSA-N 0.000 description 1
- CJKNZMSCRYFSAL-ZYMOGRSISA-N N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O Chemical compound N[C@H](Cc(cc1)ccc1Cl)C(N(CC1)CCN1c1ccnc2c1c(OCC(CO)O)n[nH]2)=O CJKNZMSCRYFSAL-ZYMOGRSISA-N 0.000 description 1
- PNASZRMIPBMOOH-DQEYMECFSA-N O=C([C@H]([C@H]1NCCC1)c(cc1)ccc1Cl)N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1 Chemical compound O=C([C@H]([C@H]1NCCC1)c(cc1)ccc1Cl)N(CC1)CCN1c(c(cn[nH]1)c1nc1)c1-c1ccccc1 PNASZRMIPBMOOH-DQEYMECFSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1986508P | 2008-01-09 | 2008-01-09 | |
| US61/019,865 | 2008-01-09 | ||
| PCT/US2009/030450 WO2009089359A1 (en) | 2008-01-09 | 2009-01-08 | Pyrazolopyridines as kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032869A Division JP2014129379A (ja) | 2008-01-09 | 2014-02-24 | キナーゼ阻害薬としてのピラゾロピリジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509302A JP2011509302A (ja) | 2011-03-24 |
| JP2011509302A5 true JP2011509302A5 (enExample) | 2012-02-16 |
| JP5608098B2 JP5608098B2 (ja) | 2014-10-15 |
Family
ID=40351716
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010542343A Expired - Fee Related JP5608098B2 (ja) | 2008-01-09 | 2009-01-08 | キナーゼ阻害薬としてのピラゾロピリジン |
| JP2014032869A Withdrawn JP2014129379A (ja) | 2008-01-09 | 2014-02-24 | キナーゼ阻害薬としてのピラゾロピリジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032869A Withdrawn JP2014129379A (ja) | 2008-01-09 | 2014-02-24 | キナーゼ阻害薬としてのピラゾロピリジン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8372842B2 (enExample) |
| EP (1) | EP2242757B1 (enExample) |
| JP (2) | JP5608098B2 (enExample) |
| CN (1) | CN101965347B (enExample) |
| CA (1) | CA2711741A1 (enExample) |
| ES (1) | ES2392014T3 (enExample) |
| WO (1) | WO2009089359A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101959887B (zh) | 2008-01-08 | 2013-07-31 | 阵列生物制药公司 | 作为激酶抑制剂的吡咯并吡啶 |
| AR071717A1 (es) | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| US8481557B2 (en) * | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| TW201304778A (zh) | 2010-11-16 | 2013-02-01 | Array Biopharma Inc | 檢查點激酶１抑制劑及ｗｅｅ１激酶抑制劑之組合 |
| EP2809668B1 (en) * | 2012-02-02 | 2017-04-12 | Actelion Pharmaceuticals Ltd. | 4-(benzoimidazol-2-yl)-thiazole compounds and related aza derivatives |
| AU2013252514B2 (en) | 2012-04-23 | 2017-07-20 | Genentech, Inc. | Intermediates and processes for preparing compounds |
| CN104119331B (zh) * | 2013-04-26 | 2018-02-06 | 广东东阳光药业有限公司 | 烯基化合物及其使用方法和用途 |
| CA2928568A1 (en) | 2013-07-26 | 2015-01-29 | Update Pharma Inc. | Combinatorial methods to improve the therapeutic benefit of bisantrene |
| KR102325163B1 (ko) | 2013-08-22 | 2021-11-11 | 제넨테크, 인크. | 화합물의 제조 방법 |
| GB201410815D0 (en) * | 2014-06-17 | 2014-07-30 | Ucb Biopharma Sprl And Katholieke Universiteit Leuven | Therapeutic agents |
| TWI899933B (zh) | 2023-04-06 | 2025-10-01 | 美商輝瑞大藥廠 | 經取代吲唑丙酸衍生化合物及其用途 |
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| DE19853278A1 (de) | 1998-11-19 | 2000-05-25 | Aventis Pharma Gmbh | Substituierte 4-Amino-2-aryl-cyclopenta[d]pyrimidine, ihre Herstellung, ihre Verwendung und sie enthaltende pharmazeutische Präparate |
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| JP2005534632A (ja) * | 2002-05-10 | 2005-11-17 | ニューロクライン バイオサイエンセズ， インコーポレイテッド | メラノコルチンレセプターリガンドとしての置換ピペラジン |
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| TW200526547A (en) * | 2003-09-22 | 2005-08-16 | Theravance Inc | Amino-substituted ethylamino β2 adrenergic receptor agonists |
| US20050130954A1 (en) * | 2003-11-21 | 2005-06-16 | Mitchell Ian S. | AKT protein kinase inhibitors |
| GB0330043D0 (en) | 2003-12-24 | 2004-01-28 | Pharmacia Italia Spa | Pyrrolo [2,3-b] pyridine derivatives active as kinase inhibitors process for their preparation and pharmaceutical compositions comprising them |
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| PE20061119A1 (es) | 2005-01-19 | 2006-11-27 | Aventis Pharma Sa | PIRAZOLO PIRIDINAS SUSTITUIDAS COMO INHIBIDORES DE CINASAS FAK, KDR Y Tie |
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| KR20080016659A (ko) * | 2005-05-20 | 2008-02-21 | 버텍스 파마슈티칼스 인코포레이티드 | 단백질 키나제의 억제제로서 유용한 피롤로피리딘 |
| WO2006130673A1 (en) | 2005-05-31 | 2006-12-07 | Janssen Pharmaceutica, N.V. | 3-benzoimidazolyl-pyrazolopyridines useful in treating kinase disorders |
| DK2395004T3 (en) | 2005-06-22 | 2016-03-21 | Plexxikon Inc | Pyrrolo [2,3-b] pyridine derivatives as protein kinase inhibitors |
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| CA2628179A1 (en) | 2005-11-15 | 2007-05-24 | Vertex Pharmaceuticals Incorporated | Azaindazoles useful as inhibitors of kinases |
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| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| ATE532789T1 (de) | 2006-07-06 | 2011-11-15 | Array Biopharma Inc | Dihydrothienopyrimidine als akt-proteinkinase- inhibitoren |
| CN101511842B (zh) | 2006-07-06 | 2012-10-31 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的二氢呋喃并嘧啶 |
| WO2008006032A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Cyclopenta [d] pyrimidines as akt protein kinase inhibitors |
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| WO2008075007A1 (en) | 2006-12-21 | 2008-06-26 | Cancer Research Technology Limited | Morpholino-substituted bicycloheteroaryl compounds and their use as anti cancer agents |
| EP2170886A1 (en) * | 2007-07-02 | 2010-04-07 | Cancer Research Technology Limited | 9h-pyrimido[4,5-b]indoles, 9h-pyrido[4',3':4,5]pyrrolo[2,3-d]pyridines, and 9h-1,3,6,9-tetraaza-fluorenes as chk1 kinase function inhibitors |
| US8618097B2 (en) | 2007-07-05 | 2013-12-31 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| SI2173723T1 (sl) | 2007-07-05 | 2011-12-30 | Array Biopharma Inc | Pirimidil ciklopentani kot inhibitorji AKT-protein-kinaze |
| AR069198A1 (es) | 2007-11-07 | 2010-01-06 | Schering Corp | Derivados de ribosil pirimidinas moduladores de quinasas de control chk1,y composiciones farmaceuticas que los comprenden utiles en el tratamiento del cancer. |
| CN101959887B (zh) * | 2008-01-08 | 2013-07-31 | 阵列生物制药公司 | 作为激酶抑制剂的吡咯并吡啶 |
| JP5346345B2 (ja) | 2008-01-09 | 2013-11-20 | アレイ バイオファーマ、インコーポレイテッド | Ａｋｔタンパク質キナーゼ阻害剤としての水酸化されたピリミジルシクロペンタン類 |
| CA2711782C (en) | 2008-01-09 | 2017-01-03 | Array Biopharma Inc. | 5h-cyclopenta[d]pyrimidines as akt protein kinase inhibitors |
| EP2240455B1 (en) | 2008-01-09 | 2012-12-26 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor |
| AR071717A1 (es) | 2008-05-13 | 2010-07-07 | Array Biopharma Inc | Pirrolo[2,3-b]piridinas inhibidoras de quinasas chk1 y chk2,composiciones farmaceuticas que las contienen,proceso para prepararlas y uso de las mismas en el tratamiento y prevencion del cancer. |
| US8481557B2 (en) * | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| CN102612365B (zh) | 2009-04-11 | 2017-04-12 | 阵列生物制药公司 | 用于强化dna损伤剂的检查点激酶1抑制剂 |
| TW201304778A (zh) | 2010-11-16 | 2013-02-01 | Array Biopharma Inc | 檢查點激酶１抑制劑及ｗｅｅ１激酶抑制劑之組合 |
-
2009
- 2009-01-08 EP EP09701216A patent/EP2242757B1/en active Active
- 2009-01-08 CA CA2711741A patent/CA2711741A1/en not_active Abandoned
- 2009-01-08 WO PCT/US2009/030450 patent/WO2009089359A1/en not_active Ceased
- 2009-01-08 CN CN2009801083206A patent/CN101965347B/zh not_active Expired - Fee Related
- 2009-01-08 ES ES09701216T patent/ES2392014T3/es active Active
- 2009-01-08 US US12/812,448 patent/US8372842B2/en not_active Expired - Fee Related
- 2009-01-08 JP JP2010542343A patent/JP5608098B2/ja not_active Expired - Fee Related
-
2014
- 2014-02-24 JP JP2014032869A patent/JP2014129379A/ja not_active Withdrawn