JP2011509301A5 - - Google Patents
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- JP2011509301A5 JP2011509301A5 JP2010542341A JP2010542341A JP2011509301A5 JP 2011509301 A5 JP2011509301 A5 JP 2011509301A5 JP 2010542341 A JP2010542341 A JP 2010542341A JP 2010542341 A JP2010542341 A JP 2010542341A JP 2011509301 A5 JP2011509301 A5 JP 2011509301A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- hydrogen
- compound
- alkyl
- phenyl
- 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 description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 38
- -1 1-oxa-3,4-diazolyl Chemical group 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 230000003463 hyperproliferative effect Effects 0.000 claims description 5
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
- 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
- 125000004429 atom Chemical group 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 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229960003966 nicotinamide Drugs 0.000 claims description 4
- 235000005152 nicotinamide Nutrition 0.000 claims description 4
- 239000011570 nicotinamide Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 150000003839 salts Chemical class 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
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- ZVXKYWHJBYIYNI-UHFFFAOYSA-N 1h-pyrazole-4-carboxamide Chemical compound NC(=O)C=1C=NNC=1 ZVXKYWHJBYIYNI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 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
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 claims description 2
- BCCUXBGEPLKSEX-UHFFFAOYSA-N 5-methylpyridine-3-carboxamide Chemical compound CC1=CN=CC(C(N)=O)=C1 BCCUXBGEPLKSEX-UHFFFAOYSA-N 0.000 claims description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 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
- 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
- 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
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 4
- 241000124008 Mammalia Species 0.000 description 4
- 0 C*(*)*(C)C(*)(CC*(C)N(*)*)C(O)=O Chemical compound C*(*)*(C)C(*)(CC*(C)N(*)*)C(O)=O 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 |
|---|---|---|---|
| US1978608P | 2008-01-08 | 2008-01-08 | |
| US61/019,786 | 2008-01-08 | ||
| PCT/US2009/030443 WO2009089352A1 (en) | 2008-01-08 | 2009-01-08 | Pyrrolopyridines as kinase inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032761A Division JP2014129376A (ja) | 2008-01-08 | 2014-02-24 | キナーゼ阻害薬としてのピロロピリジン |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011509301A JP2011509301A (ja) | 2011-03-24 |
| JP2011509301A5 true JP2011509301A5 (cg-RX-API-DMAC7.html) | 2013-02-07 |
| JP5608097B2 JP5608097B2 (ja) | 2014-10-15 |
Family
ID=40352263
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010542341A Expired - Fee Related JP5608097B2 (ja) | 2008-01-08 | 2009-01-08 | キナーゼ阻害薬としてのピロロピリジン |
| JP2014032761A Withdrawn JP2014129376A (ja) | 2008-01-08 | 2014-02-24 | キナーゼ阻害薬としてのピロロピリジン |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014032761A Withdrawn JP2014129376A (ja) | 2008-01-08 | 2014-02-24 | キナーゼ阻害薬としてのピロロピリジン |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8841304B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP2242755B1 (cg-RX-API-DMAC7.html) |
| JP (2) | JP5608097B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN101959887B (cg-RX-API-DMAC7.html) |
| CA (1) | CA2711614A1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2394759T3 (cg-RX-API-DMAC7.html) |
| WO (1) | WO2009089352A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8372842B2 (en) * | 2008-01-09 | 2013-02-12 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| 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 |
| CA2767079A1 (en) * | 2009-07-08 | 2011-01-13 | Leo Pharma A/S | Heterocyclic compounds as jak receptor and protein tyrosine kinase inhibitors |
| US20140221370A1 (en) * | 2010-07-09 | 2014-08-07 | Array Biopharma Inc. | Pyrrolopyridines as kinase inhibitors |
| CA2817968C (en) | 2010-11-16 | 2019-03-12 | Array Biopharma Inc. | Combination of checkpoint kinase 1 inhibitors and wee 1 kinase inhibitors |
| WO2012135631A1 (en) | 2011-03-30 | 2012-10-04 | Arrien Pharmaeuticals Llc | Substituted 5-(pyrazin-2-yl)-1h-pyrazolo [3, 4-b] pyridine and pyrazolo [3, 4-b] pyridine derivatives as protein kinase inhibitors |
| GB201201566D0 (en) | 2012-01-30 | 2012-03-14 | Vernalis R&D Ltd | New chemical compounds |
| MY168958A (en) * | 2012-04-23 | 2019-01-28 | Genentech Inc | Intermediates and processes for preparing compounds |
| MX369174B (es) * | 2013-08-22 | 2019-10-30 | Genentech Inc | Proceso para la preparación de un compuesto. |
| AR101106A1 (es) | 2014-07-02 | 2016-11-23 | Pharmacyclics Llc | Inhibidores de tirosina quinasa de bruton |
| TW202043198A (zh) * | 2019-01-17 | 2020-12-01 | 美商Ｉｆｍ Ｄｕｅ有限公司 | 用於治療與sting活性相關之病況的化合物及組合物 |
Family Cites Families (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1999051582A1 (en) | 1998-03-31 | 1999-10-14 | Kyowa Hakko Kogyo Co., Ltd. | Nitrogenous heterocyclic compounds |
| 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 |
| US7115741B2 (en) | 2001-09-06 | 2006-10-03 | Levy Daniel E | 4-thieno[2,3-D]pyrimidin-4-YL piperazine compounds |
| WO2003028724A1 (en) | 2001-10-04 | 2003-04-10 | Smithkline Beecham Corporation | Chk1 kinase inhibitors |
| US6797825B2 (en) | 2001-12-13 | 2004-09-28 | Abbott Laboratories | Protein kinase inhibitors |
| MXPA04011093A (es) | 2002-05-10 | 2005-02-14 | Neurocrine Biosciences Inc | Piperazina sustituida como ligandos de receptores de melanocortina. |
| US20050256157A1 (en) | 2002-08-23 | 2005-11-17 | Chiron Corporation | Combination therapy with CHK1 inhibitors |
| EP1663994B1 (en) | 2003-08-05 | 2012-03-07 | Vertex Pharmaceuticals Incorporated | Tetrahydroquinazoline compounds as inhibitors of voltage-gated ion channels |
| BRPI0414238A (pt) | 2003-09-09 | 2006-10-31 | Ono Pharmaceutical Co | antagonistas de crf e compostos heterobicìclicos |
| TW200526547A (en) | 2003-09-22 | 2005-08-16 | Theravance Inc | Amino-substituted ethylamino β2 adrenergic receptor agonists |
| JP2007512364A (ja) * | 2003-11-21 | 2007-05-17 | アレイ バイオファーマ、インコーポレイテッド | Ａｋｔプロテインキナーゼインヒビター |
| 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 |
| GB0409080D0 (en) | 2004-04-23 | 2004-05-26 | Biofocus Discovery Ltd | Compounds which interact with protein kinases |
| JP5213229B2 (ja) | 2004-04-23 | 2013-06-19 | エグゼリクシス， インコーポレイテッド | キナーゼ調節因子および使用方法 |
| UY29177A1 (es) | 2004-10-25 | 2006-05-31 | Astex Therapeutics Ltd | Derivados sustituidos de purina, purinona y deazapurina, composiciones que los contienen métodos para su preparación y sus usos |
| CA2590961C (en) | 2004-12-28 | 2013-11-26 | Exelixis, Inc. | [1h-pyrazolo[3,4-d]pyrimidin-4-yl]-piperidine or -piperazine compounds as serine-threonine kinase modulators (p70s6k, atk1 and atk2) for the treatment of immunological, inflammatory and proliferative diseases |
| PE20061119A1 (es) | 2005-01-19 | 2006-11-27 | Aventis Pharma Sa | PIRAZOLO PIRIDINAS SUSTITUIDAS COMO INHIBIDORES DE CINASAS FAK, KDR Y Tie |
| GB0501999D0 (en) | 2005-02-01 | 2005-03-09 | Sentinel Oncology Ltd | Pharmaceutical compounds |
| JP2008534664A (ja) | 2005-04-06 | 2008-08-28 | アストラゼネカ アクチボラグ | 置換複素環およびｃｈｋ１、ｐｄｋ１及びｐａｋ阻害剤としてのそれらの使用 |
| WO2006127587A1 (en) | 2005-05-20 | 2006-11-30 | Vertex Pharmaceuticals Incorporated | Pyrrolopyridines useful as inhibitors of protein kinase |
| US7541367B2 (en) | 2005-05-31 | 2009-06-02 | Janssen Pharmaceutica, N.V. | 3-benzoimidazolyl-pyrazolopyridines useful in treating kinase disorders |
| CN102603581B (zh) | 2005-06-22 | 2015-06-24 | 普莱希科公司 | 作为蛋白质激酶抑制剂的吡咯并[2,3-b]吡啶衍生物 |
| TWI421078B (zh) | 2005-10-06 | 2014-01-01 | Merck Sharp & Dohme | 關卡激酶抑制劑及其用途 |
| EP2514751A1 (en) | 2005-11-15 | 2012-10-24 | Vertex Pharmaceuticals, Inc. | Azaindazoles useful as inhibitor of kinases |
| DE102006005180A1 (de) | 2006-02-06 | 2007-08-09 | Merck Patent Gmbh | Indazol-heteroaryl-derivate |
| DE102006005179A1 (de) | 2006-02-06 | 2007-08-09 | Merck Patent Gmbh | Aminoindazolderivate |
| RU2008139599A (ru) | 2006-03-07 | 2010-04-20 | Эррэй Биофарма Инк. (Us) | Гетеробициклические производные пиразола и способы их применения |
| WO2007125321A2 (en) | 2006-04-25 | 2007-11-08 | Astex Therapeutics Limited | Purine and deazapurine derivatives as pharmaceutical compounds |
| JP2009534454A (ja) | 2006-04-25 | 2009-09-24 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| WO2008006039A1 (en) | 2006-07-06 | 2008-01-10 | Array Biopharma Inc. | Dihydrothieno pyrimidines as akt protein kinase inhibitors |
| SI2049500T1 (sl) | 2006-07-06 | 2012-01-31 | Array Biopharma Inc | Ciklopenta (d) pirimidini kot AKT protein kinazni inhibitorji |
| 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 |
| WO2008012635A2 (en) | 2006-07-26 | 2008-01-31 | Pfizer Products Inc. | Amine derivatives useful as anticancer agents |
| 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 |
| KR20150089099A (ko) | 2007-07-05 | 2015-08-04 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 억제제로서의 피리미딜 시클로펜탄 |
| US8377937B2 (en) | 2007-07-05 | 2013-02-19 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| JP2011503084A (ja) | 2007-11-07 | 2011-01-27 | シェーリング コーポレイション | 新規の細胞周期チェックポイント調節剤およびこれらの調節剤とチェックポイント阻害剤との併用 |
| CN101932564B (zh) | 2008-01-09 | 2012-12-26 | 阵列生物制药公司 | 作为akt蛋白激酶抑制剂的羟基化嘧啶基环戊烷类 |
| JP5539225B2 (ja) | 2008-01-09 | 2014-07-02 | 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 |
| US8372842B2 (en) * | 2008-01-09 | 2013-02-12 | Array Biopharma Inc. | Pyrazolopyridines as kinase inhibitors |
| JP5635910B2 (ja) | 2008-01-09 | 2014-12-03 | 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５Ｈ−シクロペンタ［ｄ］ピリミジン |
| 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. |
| SG10201900212QA (en) | 2009-04-11 | 2019-02-27 | Array Biopharma Inc | Checkpoint kinase 1 inhibitors for potentiating dna damaging agents |
| US8481557B2 (en) | 2009-04-11 | 2013-07-09 | Array Biopharma Inc. | Method of treatment using checkpoint kinase 1 inhibitors |
| CA2817968C (en) | 2010-11-16 | 2019-03-12 | Array Biopharma Inc. | Combination of checkpoint kinase 1 inhibitors and wee 1 kinase inhibitors |
-
2009
- 2009-01-08 WO PCT/US2009/030443 patent/WO2009089352A1/en not_active Ceased
- 2009-01-08 ES ES09700828T patent/ES2394759T3/es active Active
- 2009-01-08 JP JP2010542341A patent/JP5608097B2/ja not_active Expired - Fee Related
- 2009-01-08 CA CA2711614A patent/CA2711614A1/en not_active Abandoned
- 2009-01-08 EP EP09700828A patent/EP2242755B1/en active Active
- 2009-01-08 CN CN2009801081982A patent/CN101959887B/zh not_active Expired - Fee Related
- 2009-01-08 US US12/812,447 patent/US8841304B2/en not_active Expired - Fee Related
-
2014
- 2014-02-24 JP JP2014032761A patent/JP2014129376A/ja not_active Withdrawn