JP2011503099A5 - - Google Patents
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- Publication number
- JP2011503099A5 JP2011503099A5 JP2010533285A JP2010533285A JP2011503099A5 JP 2011503099 A5 JP2011503099 A5 JP 2011503099A5 JP 2010533285 A JP2010533285 A JP 2010533285A JP 2010533285 A JP2010533285 A JP 2010533285A JP 2011503099 A5 JP2011503099 A5 JP 2011503099A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- alkyl
- oxo
- carboxamide
- tetrahydroindolizine
- 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
- -1 cyano, thio, oxy, hydroxy, carbonyloxy Chemical group 0.000 claims 27
- 150000001875 compounds Chemical class 0.000 claims 19
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 150000003857 carboxamides Chemical class 0.000 claims 9
- 125000005842 heteroatom Chemical group 0.000 claims 8
- 229910052739 hydrogen Inorganic materials 0.000 claims 8
- 239000001257 hydrogen Substances 0.000 claims 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 125000003118 aryl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- MDINGYBMHOPYQH-UHFFFAOYSA-N 6-chloro-7-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(Cl)=C1NC1=CC=C(I)C=C1F MDINGYBMHOPYQH-UHFFFAOYSA-N 0.000 claims 1
- MIBKUYFVZVEADN-UHFFFAOYSA-N 6-fluoro-7-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(F)=C1NC1=CC=C(I)C=C1F MIBKUYFVZVEADN-UHFFFAOYSA-N 0.000 claims 1
- RBYIURLPUPZLAC-UHFFFAOYSA-N 6-fluoro-7-(2-fluoro-4-iodoanilino)-n-(3-hydroxypropoxy)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCCONC(=O)C1=C2CCCN2C(=O)C(F)=C1NC1=CC=C(I)C=C1F RBYIURLPUPZLAC-UHFFFAOYSA-N 0.000 claims 1
- UPLHQDFQQZDQQB-UHFFFAOYSA-N 7-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C=C1NC1=CC=C(I)C=C1F UPLHQDFQQZDQQB-UHFFFAOYSA-N 0.000 claims 1
- VSZNNXCPOIBREY-UHFFFAOYSA-N 7-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)-6-methyl-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(C)=C1NC1=CC=C(I)C=C1F VSZNNXCPOIBREY-UHFFFAOYSA-N 0.000 claims 1
- BKZHHWSGUZPVIY-UHFFFAOYSA-N 7-(4-bromo-2-fluoroanilino)-6-fluoro-n-(2-hydroxyethoxy)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(F)=C1NC1=CC=C(Br)C=C1F BKZHHWSGUZPVIY-UHFFFAOYSA-N 0.000 claims 1
- JNEXVTRXIDHXHP-UHFFFAOYSA-N 7-(4-bromo-2-fluoroanilino)-n-(2-hydroxyethoxy)-6-methyl-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(C)=C1NC1=CC=C(Br)C=C1F JNEXVTRXIDHXHP-UHFFFAOYSA-N 0.000 claims 1
- QUXCVJUXKUSVQD-UHFFFAOYSA-N 7-(4-ethynyl-2-fluoroanilino)-6-fluoro-n-(2-hydroxyethoxy)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(F)=C1NC1=CC=C(C#C)C=C1F QUXCVJUXKUSVQD-UHFFFAOYSA-N 0.000 claims 1
- PFCILVQESKRVSI-UHFFFAOYSA-N 7-(4-ethynyl-2-fluoroanilino)-n-(2-hydroxyethoxy)-6-methyl-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OCCONC(=O)C1=C2CCCN2C(=O)C(C)=C1NC1=CC=C(C#C)C=C1F PFCILVQESKRVSI-UHFFFAOYSA-N 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 125000005553 heteroaryloxy group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001841 imino group Chemical group [H]N=* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- DLUDRGRCQCHJFO-LLVKDONJSA-N n-[(2r)-2,3-dihydroxypropoxy]-7-(2-fluoro-4-iodoanilino)-5-oxo-2,3-dihydro-1h-indolizine-8-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C1=C2CCCN2C(=O)C=C1NC1=CC=C(I)C=C1F DLUDRGRCQCHJFO-LLVKDONJSA-N 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 229940124530 sulfonamide Drugs 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US98727907P | 2007-11-12 | 2007-11-12 | |
| US60/987,279 | 2007-11-12 | ||
| PCT/US2008/082846 WO2009064675A1 (en) | 2007-11-12 | 2008-11-07 | Mapk/erk kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011503099A JP2011503099A (ja) | 2011-01-27 |
| JP2011503099A5 true JP2011503099A5 (enExample) | 2011-12-08 |
| JP5453290B2 JP5453290B2 (ja) | 2014-03-26 |
Family
ID=40340592
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010533285A Active JP5453290B2 (ja) | 2007-11-12 | 2008-11-07 | Ｍａｐｋ／ｅｒｋキナーゼ阻害剤 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US8022057B2 (enExample) |
| EP (1) | EP2227469B9 (enExample) |
| JP (1) | JP5453290B2 (enExample) |
| AR (1) | AR069462A1 (enExample) |
| CA (1) | CA2705452C (enExample) |
| CL (1) | CL2008003366A1 (enExample) |
| ES (1) | ES2456966T3 (enExample) |
| PE (1) | PE20090998A1 (enExample) |
| TW (1) | TW200934775A (enExample) |
| WO (1) | WO2009064675A1 (enExample) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7723477B2 (en) | 2005-10-31 | 2010-05-25 | Oncomed Pharmaceuticals, Inc. | Compositions and methods for inhibiting Wnt-dependent solid tumor cell growth |
| NZ577047A (en) | 2006-10-23 | 2011-02-25 | Takeda Pharmaceutical | Mapk/erk kinase inhibitors |
| JO2985B1 (ar) | 2006-12-20 | 2016-09-05 | Takeda Pharmaceuticals Co | مثبطات كينازmapk/erk |
| CL2009000949A1 (es) * | 2008-04-21 | 2010-12-24 | Novartis Ag | Compuestos derivados de 1,2,3,5-tetrahidro-indolizina, 6,7,8,9-tetrahidro-4h-quinolizina sustituidos, inhibidores de la actividad de cinasa de mek; su composicion farmaceutica; su uso para el tratamiento de enfermedades hiperproliferativas, tal como cancer e inflamaciones. |
| TWI506037B (zh) | 2008-09-26 | 2015-11-01 | Oncomed Pharm Inc | 捲曲結合劑類及彼等之用途 |
| CN102458580A (zh) * | 2009-04-21 | 2012-05-16 | 诺瓦提斯公司 | 作为mek抑制剂的杂环化合物 |
| MY156209A (en) | 2009-11-04 | 2016-01-29 | Novartis Ag | Heterocyclic sulfonamide derivatives useful mek inhibitors |
| WO2011067348A2 (en) | 2009-12-03 | 2011-06-09 | Novartis Ag | Mek inhibitor salts and solvates thereof |
| CN101747300B (zh) * | 2009-12-22 | 2012-11-07 | 上海大学 | 基于紫杉醇和氮芥的协同前药及其制备方法 |
| TWI535445B (zh) | 2010-01-12 | 2016-06-01 | 安可美德藥物股份有限公司 | Ｗｎｔ拮抗劑及治療和篩選方法 |
| CN102020651B (zh) * | 2010-11-02 | 2012-07-18 | 北京赛林泰医药技术有限公司 | 6-芳基氨基吡啶酮甲酰胺mek抑制剂 |
| AR087309A1 (es) * | 2011-07-27 | 2014-03-12 | Glaxo Group Ltd | Compuesto heterociclico de anillos condensados sustituido, composicion farmaceutica que lo comprende y su uso para la fabricacion de un medicamento para el tratamiento de enfermedades neurogenerativas y aterosclerosis |
| EP2739358B1 (en) | 2011-08-01 | 2018-11-28 | F.Hoffmann-La Roche Ag | Methods of treating cancer using pd-1 axis binding antagonists and mek inhibitors |
| US20150132301A1 (en) * | 2011-12-09 | 2015-05-14 | Oncomed Pharmaceuticals, Inc. | Combination Therapy for Treatment of Cancer |
| WO2013109142A1 (en) | 2012-01-16 | 2013-07-25 | Stichting Het Nederlands Kanker Instituut | Combined pdk and mapk/erk pathway inhibition in neoplasia |
| PL3702351T3 (pl) | 2012-10-19 | 2024-04-02 | Array Biopharma, Inc. | Formulacja zawierająca inhibitor mek |
| JP2016510411A (ja) | 2013-02-04 | 2016-04-07 | オンコメッド ファーマシューティカルズ インコーポレイテッド | Ｗｎｔ経路インヒビターによる処置の方法およびモニタリング |
| US9216163B2 (en) | 2013-05-20 | 2015-12-22 | Kyorin Pharmaceutical Co., Ltd. | Method of inhibiting angiogenesis |
| WO2014204263A1 (en) * | 2013-06-20 | 2014-12-24 | The Asan Foundation | Substituted pyridinone compounds as mek inhibitors |
| WO2015041534A1 (en) | 2013-09-20 | 2015-03-26 | Stichting Het Nederlands Kanker Instituut | P90rsk in combination with raf/erk/mek |
| EP3046557A1 (en) | 2013-09-20 | 2016-07-27 | Stichting Het Nederlands Kanker Instituut | Rock in combination with mapk-pathway |
| US20170027940A1 (en) | 2014-04-10 | 2017-02-02 | Stichting Het Nederlands Kanker Instituut | Method for treating cancer |
| WO2015178770A1 (en) | 2014-05-19 | 2015-11-26 | Stichting Het Nederlands Kanker Instituut | Compositions for cancer treatment |
| MX2017000546A (es) | 2014-07-15 | 2017-03-08 | Genentech Inc | Composiciones para el tratamiento del cancer mediante el uso de antagonistas de union al eje de pd-1 e inhibidores de mek. |
| WO2017058007A1 (en) | 2015-10-01 | 2017-04-06 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Histone deacetylase inhibitors for the use in the treatment of drug resistant melanoma |
| WO2017099591A1 (en) | 2015-12-07 | 2017-06-15 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Treatment of inhibitor resistant braf-mutant cancers |
| WO2017204626A1 (en) | 2016-05-24 | 2017-11-30 | Stichting Het Nederlands Kanker Instituut-Antoni van Leeuwenhoek Ziekenhuis | Combination therapy - combined map2k4/map3k1 and mek/erk inhibition |
| WO2018218633A1 (en) | 2017-06-02 | 2018-12-06 | Beijing Percans Oncology Co. Ltd. | Combination therapies for treating cancers |
| WO2019195959A1 (en) | 2018-04-08 | 2019-10-17 | Cothera Biosciences, Inc. | Combination therapy for cancers with braf mutation |
| JP7507145B2 (ja) | 2018-08-13 | 2024-06-27 | ベイジン パーカンズ オンコロジー カンパニー リミテッド | 癌治療のためのバイオマーカー |
| CN111662282B (zh) * | 2019-03-07 | 2021-07-06 | 湖南化工研究院有限公司 | 氮杂环并吡啶类化合物及其中间体 |
Family Cites Families (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0670044B2 (ja) * | 1987-11-20 | 1994-09-07 | キッセイ薬品工業株式会社 | ４ｈ―キノリジン―４―オン誘導体 |
| AU616916B2 (en) * | 1987-11-20 | 1991-11-14 | Kissei Pharmaceutical Co. Ltd. | 4h-quinolizin-4-one compounds exhibiting therapeutic activities |
| WO1998037881A1 (en) | 1997-02-28 | 1998-09-03 | Warner Lambert Company | Method of treating or preventing septic shock by administering a mek inhibitor |
| CA2349180A1 (en) | 1999-01-13 | 2000-07-20 | Stephen Douglas Barrett | Anthranilic acid derivatives |
| US7235537B2 (en) | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| TWI343377B (en) | 2002-03-13 | 2011-06-11 | Array Biopharma Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| WO2003077855A2 (en) | 2002-03-13 | 2003-09-25 | Array Biopharma, Inc | N3 alkylated benzimidazole derivatives as mek inhibitors |
| WO2005000818A1 (en) * | 2003-06-27 | 2005-01-06 | Warner-Lambert Company Llc | 5-substituted-4-`(substituted phenyl)!amino!-2-pyridone deviatives for use as mek inhibitors |
| US20050049276A1 (en) * | 2003-07-23 | 2005-03-03 | Warner-Lambert Company, Llc | Imidazopyridines and triazolopyridines |
| BRPI0412851A (pt) * | 2003-07-24 | 2006-10-03 | Warner Lambert Co | benzamidazóis de n-metila-substituìdos |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7517994B2 (en) * | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| NZ547481A (en) | 2003-11-19 | 2009-12-24 | Array Biopharma Inc | Heterocyclic inhibitors of mek and methods of use thereof |
| PT2298768E (pt) | 2004-06-11 | 2012-12-05 | Japan Tobacco Inc | Derivados de 5-amino-2,4,7-trioxo-3,4,7,8-tetra-hidro-2hpirido[ 2,3-d]pirimidina e compostos relacionados para o tratamento do cancro |
| JP2008520615A (ja) | 2004-11-24 | 2008-06-19 | ラボラトワール セローノ ソシエテ アノニム | 過増殖性障害を処置するためのｍｅｋ阻害剤としての新規４−アリールアミノピリドン誘導体 |
| ATE443063T1 (de) | 2004-12-01 | 2009-10-15 | Merck Serono Sa | Ä1,2,4ütriazoloä4,3-aüpyridin-derivative zur behandlung hyperproliferativer erkrankungen |
| CN102898364A (zh) * | 2005-05-18 | 2013-01-30 | 阵列生物制药公司 | Mek的杂环抑制剂及其使用方法 |
| NZ577047A (en) | 2006-10-23 | 2011-02-25 | Takeda Pharmaceutical | Mapk/erk kinase inhibitors |
| EP2113500A1 (en) * | 2006-10-31 | 2009-11-04 | Takeda Pharmaceutical Company Limited | MAPK/ERK kinase inhibitors |
| JO2985B1 (ar) * | 2006-12-20 | 2016-09-05 | Takeda Pharmaceuticals Co | مثبطات كينازmapk/erk |
| CL2009000949A1 (es) * | 2008-04-21 | 2010-12-24 | Novartis Ag | Compuestos derivados de 1,2,3,5-tetrahidro-indolizina, 6,7,8,9-tetrahidro-4h-quinolizina sustituidos, inhibidores de la actividad de cinasa de mek; su composicion farmaceutica; su uso para el tratamiento de enfermedades hiperproliferativas, tal como cancer e inflamaciones. |
| CN102458580A (zh) | 2009-04-21 | 2012-05-16 | 诺瓦提斯公司 | 作为mek抑制剂的杂环化合物 |
-
2008
- 2008-11-07 US US12/267,353 patent/US8022057B2/en active Active
- 2008-11-07 ES ES08849376.2T patent/ES2456966T3/es active Active
- 2008-11-07 CA CA2705452A patent/CA2705452C/en not_active Expired - Fee Related
- 2008-11-07 WO PCT/US2008/082846 patent/WO2009064675A1/en not_active Ceased
- 2008-11-07 JP JP2010533285A patent/JP5453290B2/ja active Active
- 2008-11-07 EP EP08849376.2A patent/EP2227469B9/en active Active
- 2008-11-11 TW TW097143569A patent/TW200934775A/zh unknown
- 2008-11-12 CL CL2008003366A patent/CL2008003366A1/es unknown
- 2008-11-12 AR ARP080104939A patent/AR069462A1/es unknown
- 2008-11-12 PE PE2008001910A patent/PE20090998A1/es not_active Application Discontinuation
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