JP2011526926A5 - - Google Patents
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- Publication number
- JP2011526926A5 JP2011526926A5 JP2011516860A JP2011516860A JP2011526926A5 JP 2011526926 A5 JP2011526926 A5 JP 2011526926A5 JP 2011516860 A JP2011516860 A JP 2011516860A JP 2011516860 A JP2011516860 A JP 2011516860A JP 2011526926 A5 JP2011526926 A5 JP 2011526926A5
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- amide
- carboxylic acid
- phenylamino
- compound according
- 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 22
- 125000000217 alkyl group Chemical group 0.000 claims 12
- 241000124008 Mammalia Species 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004452 carbocyclyl group Chemical group 0.000 claims 3
- 230000002159 abnormal effect Effects 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 230000010261 cell growth Effects 0.000 claims 2
- 239000003795 chemical substances by application Substances 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000003463 hyperproliferative Effects 0.000 claims 2
- 200000000018 inflammatory disease Diseases 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 239000011780 sodium chloride Substances 0.000 claims 2
- LQRZNLGKCYARCP-UHFFFAOYSA-N 4-(2-fluoro-4-iodoanilino)-N-(1-hydroxy-2-methylpropan-2-yl)oxy-1H-pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound OCC(C)(C)ONC(=O)C1=CN=C2NN=CC2=C1NC1=CC=C(I)C=C1F LQRZNLGKCYARCP-UHFFFAOYSA-N 0.000 claims 1
- GQTQXWHZDPDURC-UHFFFAOYSA-N 4-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1,2-benzothiazole-5-carboxamide Chemical compound OCCONC(=O)C1=CC=C2SN=CC2=C1NC1=CC=C(I)C=C1F GQTQXWHZDPDURC-UHFFFAOYSA-N 0.000 claims 1
- YMRXJLXWVAGVBT-UHFFFAOYSA-N 4-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1H-indazole-5-carboxamide Chemical compound OCCONC(=O)C1=CC=C2NN=CC2=C1NC1=CC=C(I)C=C1F YMRXJLXWVAGVBT-UHFFFAOYSA-N 0.000 claims 1
- JKZGFJXSSQZDOU-UHFFFAOYSA-N 4-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1H-pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound OCCONC(=O)C1=CN=C2NN=CC2=C1NC1=CC=C(I)C=C1F JKZGFJXSSQZDOU-UHFFFAOYSA-N 0.000 claims 1
- IJOPYGAXIHQICU-UHFFFAOYSA-N 4-(2-fluoro-4-iodoanilino)-N-(oxan-4-yloxy)-1H-indazole-5-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOC2CCOCC2)C=CC2=C1C=NN2 IJOPYGAXIHQICU-UHFFFAOYSA-N 0.000 claims 1
- HQBQYHYNUJJVDY-VIFPVBQESA-N 4-(2-fluoro-4-iodoanilino)-N-[(2S)-2-hydroxypropoxy]-1,2-benzothiazole-5-carboxamide Chemical compound C[C@H](O)CONC(=O)C1=CC=C2SN=CC2=C1NC1=CC=C(I)C=C1F HQBQYHYNUJJVDY-VIFPVBQESA-N 0.000 claims 1
- FXQYDGOQAWPLHY-QMMMGPOBSA-N 4-(2-fluoro-4-iodoanilino)-N-[(2S)-2-hydroxypropoxy]-1H-pyrazolo[3,4-b]pyridine-5-carboxamide Chemical compound C[C@H](O)CONC(=O)C1=CN=C2NN=CC2=C1NC1=CC=C(I)C=C1F FXQYDGOQAWPLHY-QMMMGPOBSA-N 0.000 claims 1
- PJBCKFFOHMEAQE-UHFFFAOYSA-N 4-(2-fluoro-4-iodoanilino)-N-methoxy-1H-indazole-5-carboxamide Chemical compound CONC(=O)C1=CC=C2NN=CC2=C1NC1=CC=C(I)C=C1F PJBCKFFOHMEAQE-UHFFFAOYSA-N 0.000 claims 1
- AZZLAYRJGBKAJL-UHFFFAOYSA-N 4-(2-fluoro-4-methylsulfanylanilino)-N-(2-hydroxyethoxy)-1H-indazole-5-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOCCO)C=CC2=C1C=NN2 AZZLAYRJGBKAJL-UHFFFAOYSA-N 0.000 claims 1
- IJAVJYYBFRTIAU-UHFFFAOYSA-N 4-(4-bromo-2-fluoroanilino)-N-(2-hydroxyethoxy)-1H-indazole-5-carboxamide Chemical compound OCCONC(=O)C1=CC=C2NN=CC2=C1NC1=CC=C(Br)C=C1F IJAVJYYBFRTIAU-UHFFFAOYSA-N 0.000 claims 1
- ANOLNVJFCNLIDK-VIFPVBQESA-N 4-(4-bromo-2-fluoroanilino)-N-[(2S)-2-hydroxypropoxy]-1H-indazole-5-carboxamide Chemical compound C[C@H](O)CONC(=O)C1=CC=C2NN=CC2=C1NC1=CC=C(Br)C=C1F ANOLNVJFCNLIDK-VIFPVBQESA-N 0.000 claims 1
- RWZBARRAYNKEQD-UHFFFAOYSA-N 7-(2-fluoro-4-iodoanilino)-N-(2-hydroxyethoxy)-1,2-benzothiazole-6-carboxamide Chemical compound OCCONC(=O)C1=CC=C2C=NSC2=C1NC1=CC=C(I)C=C1F RWZBARRAYNKEQD-UHFFFAOYSA-N 0.000 claims 1
- NKWCGFFLRWBOEF-UHFFFAOYSA-N 7-(4-bromo-2-fluoroanilino)-N-(2-hydroxyethoxy)-1,2-benzothiazole-6-carboxamide Chemical compound OCCONC(=O)C1=CC=C2C=NSC2=C1NC1=CC=C(Br)C=C1F NKWCGFFLRWBOEF-UHFFFAOYSA-N 0.000 claims 1
- VYIKFFVOVOTEQC-LLVKDONJSA-N 7-(4-bromo-2-fluoroanilino)-N-[(2R)-2,3-dihydroxypropoxy]-1,2-benzothiazole-6-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C2C=NSC2=C1NC1=CC=C(Br)C=C1F VYIKFFVOVOTEQC-LLVKDONJSA-N 0.000 claims 1
- JKTVFQGPPKJXHP-CQSZACIVSA-N 7-(4-cyclopropyl-2-fluoroanilino)-N-[(2R)-2,3-dihydroxypropoxy]-1,2-benzothiazole-6-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C2C=NSC2=C1NC(C(=C1)F)=CC=C1C1CC1 JKTVFQGPPKJXHP-CQSZACIVSA-N 0.000 claims 1
- 241000255925 Diptera Species 0.000 claims 1
- DDHMFHZVMCWHNC-UHFFFAOYSA-N N-(cyclopropylmethoxy)-4-(2-fluoro-4-iodoanilino)-1H-indazole-5-carboxamide Chemical compound FC1=CC(I)=CC=C1NC1=C(C(=O)NOCC2CC2)C=CC2=C1C=NN2 DDHMFHZVMCWHNC-UHFFFAOYSA-N 0.000 claims 1
- LILVBVDAEFDXRJ-SNVBAGLBSA-N N-[(2R)-2,3-dihydroxypropoxy]-4-(2-fluoro-4-iodoanilino)-1,2-benzothiazole-5-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C2SN=CC2=C1NC1=CC=C(I)C=C1F LILVBVDAEFDXRJ-SNVBAGLBSA-N 0.000 claims 1
- GSFYVLMDLFXESB-SNVBAGLBSA-N N-[(2R)-2,3-dihydroxypropoxy]-4-(2-fluoro-4-iodoanilino)-1H-indazole-5-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C2NN=CC2=C1NC1=CC=C(I)C=C1F GSFYVLMDLFXESB-SNVBAGLBSA-N 0.000 claims 1
- FOOQXAKAICKOPK-LLVKDONJSA-N N-[(2R)-2,3-dihydroxypropoxy]-7-(2-fluoro-4-iodoanilino)-1,2-benzothiazole-6-carboxamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C2C=NSC2=C1NC1=CC=C(I)C=C1F FOOQXAKAICKOPK-LLVKDONJSA-N 0.000 claims 1
- CHULVOSWXYGKAP-LLVKDONJSA-N N-[(2R)-2,3-dihydroxypropoxy]-7-(2-fluoro-4-methylsulfanylanilino)-1,2-benzothiazole-6-carboxamide Chemical compound FC1=CC(SC)=CC=C1NC1=C(C(=O)NOC[C@H](O)CO)C=CC2=C1SN=C2 CHULVOSWXYGKAP-LLVKDONJSA-N 0.000 claims 1
- BEYHNMFRDWRJGB-UHFFFAOYSA-N N-ethoxy-4-(2-fluoro-4-iodoanilino)-1H-indazole-5-carboxamide Chemical compound CCONC(=O)C1=CC=C2NN=CC2=C1NC1=CC=C(I)C=C1F BEYHNMFRDWRJGB-UHFFFAOYSA-N 0.000 claims 1
- OPQRTAHIGADTMO-UHFFFAOYSA-N [4-(2-fluoro-4-iodoanilino)-1H-indazol-5-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound C1C(O)CN1C(=O)C1=CC=C(NN=C2)C2=C1NC1=CC=C(I)C=C1F OPQRTAHIGADTMO-UHFFFAOYSA-N 0.000 claims 1
- 239000002260 anti-inflammatory agent Substances 0.000 claims 1
- 229940121363 anti-inflammatory agents Drugs 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 229920000728 polyester Polymers 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7742608P | 2008-07-01 | 2008-07-01 | |
| US61/077,426 | 2008-07-01 | ||
| PCT/US2009/049453 WO2010003025A1 (en) | 2008-07-01 | 2009-07-01 | Bicyclic heterocycles as mek kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011526926A JP2011526926A (ja) | 2011-10-20 |
| JP2011526926A5 true JP2011526926A5 (US20070167479A1-20070719-C00034.png) | 2012-08-16 |
| JP5544358B2 JP5544358B2 (ja) | 2014-07-09 |
Family
ID=41038842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011516860A Expired - Fee Related JP5544358B2 (ja) | 2008-07-01 | 2009-07-01 | 置換二環式ヘテロ環化合物と使用方法 |
Country Status (15)
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EA201200651A1 (ru) | 2009-11-04 | 2012-12-28 | Новартис Аг | Гетероциклические сульфонамидные производные, применимые в качестве ингибиторов мек |
| AU2012265844A1 (en) * | 2009-12-08 | 2013-05-02 | Novartis Ag | Heterocyclic sulfonamide derivatives |
| 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 |
| AU2013337702A1 (en) | 2012-11-02 | 2015-05-21 | Merck Patent Gmbh | Method of reducing adverse effects in a cancer patient undergoing treatment with a MEK inhibitor |
| US9227969B2 (en) | 2013-08-14 | 2016-01-05 | Novartis Ag | Compounds and compositions as inhibitors of MEK |
| US9532987B2 (en) | 2013-09-05 | 2017-01-03 | Genentech, Inc. | Use of a combination of a MEK inhibitor and an ERK inhibitor for treatment of hyperproliferative diseases |
| NO2714752T3 (US20070167479A1-20070719-C00034.png) | 2014-05-08 | 2018-04-21 | ||
| CN104119332B (zh) * | 2014-07-08 | 2019-03-29 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的苯并杂环化合物及其制备方法和用途 |
| CN104860869B (zh) * | 2015-04-03 | 2017-11-03 | 北京大学 | 具有mek激酶抑制功能的化合物及其制备方法与应用 |
| HUE050317T2 (hu) | 2015-05-20 | 2020-11-30 | Amgen Inc | APJ receptor triazol agonistái |
| WO2017033113A1 (en) | 2015-08-21 | 2017-03-02 | Acerta Pharma B.V. | Therapeutic combinations of a mek inhibitor and a btk inhibitor |
| GB201516504D0 (en) | 2015-09-17 | 2015-11-04 | Astrazeneca Ab | Imadazo(4,5-c)quinolin-2-one Compounds and their use in treating cancer |
| AU2017249229A1 (en) | 2016-04-15 | 2018-10-04 | Genentech, Inc. | Diagnostic and therapeutic methods for cancer |
| WO2017192485A1 (en) | 2016-05-03 | 2017-11-09 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the apj receptor |
| HUE057733T2 (hu) | 2016-10-28 | 2022-06-28 | Chia Tai Tianqing Pharmaceutical Group Co Ltd | Neuropátiás faktor tirozinkináz receptor inhibitorként alkalmazott amino-pirazolopirimidin vegyület |
| WO2018093580A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
| WO2018093579A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
| EP3541805B1 (en) | 2016-11-16 | 2020-10-14 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
| MA46824A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole substitués par alkyle en tant qu'agonistes du récepteur apj |
| US10736883B2 (en) | 2016-11-16 | 2020-08-11 | Amgen Inc. | Triazole furan compounds as agonists of the APJ receptor |
| WO2018093577A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
| AU2018329925A1 (en) | 2017-09-08 | 2020-03-05 | F. Hoffmann-La Roche Ag | Diagnostic and therapeutic methods for cancer |
| EP3704122B1 (en) | 2017-11-03 | 2021-09-01 | Amgen Inc. | Fused triazole agonists of the apj receptor |
| EP3752200A1 (en) | 2018-02-13 | 2020-12-23 | Vib Vzw | Targeting minimal residual disease in cancer with rxr antagonists |
| US11807624B2 (en) | 2018-05-01 | 2023-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the APJ receptor |
| JP2023504623A (ja) * | 2019-12-04 | 2023-02-06 | アーカス バイオサイエンシーズ，インコーポレーテッド | Ｈｉｆ－２アルファの阻害剤 |
| CN113336786B (zh) * | 2021-05-31 | 2022-10-18 | 南京工业大学 | 一种非对映选择性的多取代环烷基化合物及其制备方法 |
| WO2024033381A1 (en) | 2022-08-10 | 2024-02-15 | Vib Vzw | Inhibition of tcf4/itf2 in the treatment of cancer |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2017853C3 (de) | 1970-04-14 | 1975-12-11 | Standard Elektrik Lorenz Ag, 7000 Stuttgart | Steuerverfahren zur Sicherung der Informationsverarbeitung und -Übertragung |
| ZA711710B (en) * | 1970-05-28 | 1971-12-29 | Squibb & Sons Inc | Amino derivatives of purazolo-pyridine carboxylic acids and esters |
| US3736326A (en) * | 1971-03-29 | 1973-05-29 | Squibb & Sons Inc | Isoxazolopyridine carboxylic acids and esters |
| US3780047A (en) * | 1972-07-05 | 1973-12-18 | Squibb & Sons Inc | Derivatives of pyrazolo(3',4'-2,3)pyrido(4,5-e)b-benzo-1,5-diazepines |
| US4012373A (en) * | 1972-09-22 | 1977-03-15 | E. R. Squibb & Sons, Inc. | Pyrazolo[3',4'-2,3]pyrido[4,5-e]b-benzo-1,5-diazepinones |
| GB8404586D0 (en) * | 1984-02-22 | 1984-03-28 | Beecham Group Plc | Compounds |
| JP2002020386A (ja) * | 2000-07-07 | 2002-01-23 | Ono Pharmaceut Co Ltd | ピラゾロピリジン誘導体 |
| CN1219753C (zh) | 2000-07-19 | 2005-09-21 | 沃尼尔·朗伯公司 | 4－碘苯氨基苯氧肟酸的氧合酯 |
| US20050009876A1 (en) * | 2000-07-31 | 2005-01-13 | Bhagwat Shripad S. | Indazole compounds, compositions thereof and methods of treatment therewith |
| UA76837C2 (uk) | 2002-03-13 | 2006-09-15 | Еррей Байофарма Інк. | N3 алкіловані похідні бензімідазолу як інгібітори мек |
| ES2549159T3 (es) | 2002-03-13 | 2015-10-23 | Array Biopharma, Inc. | Derivados de bencimidazol N3-alquilados como inhibidores de MEK |
| GB0220581D0 (en) | 2002-09-04 | 2002-10-09 | Novartis Ag | Organic Compound |
| CL2003002287A1 (es) * | 2002-11-25 | 2005-01-14 | Wyeth Corp | COMPUESTOS DERIVADOS DE TIENO[3,2-b]-PIRIDINA-6-CARBONITRILOS Y TIENEO[2,3-b]-PIRIDINA-5-CARBONITRILOS, COMPOSICION FARMACEUTICA, PROCEDIMIENTO DE PREPARACION Y COMPUESTOS INTERMEDIARIOS, Y SU USO EN EL TRATAMIENTO DEL CANCER, APOPLEJIA, OSTEOPOROSIS |
| GB0316237D0 (en) | 2003-07-11 | 2003-08-13 | Astrazeneca Ab | Therapeutic agents |
| GB0316232D0 (en) | 2003-07-11 | 2003-08-13 | Astrazeneca Ab | Therapeutic agents |
| US20050049276A1 (en) * | 2003-07-23 | 2005-03-03 | Warner-Lambert Company, Llc | Imidazopyridines and triazolopyridines |
| ATE506953T1 (de) | 2003-08-07 | 2011-05-15 | Rigel Pharmaceuticals Inc | 2,4-pyrimidindiamin-verbindungen und verwendungen als antiproliferative mittel |
| US7144907B2 (en) * | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7538120B2 (en) * | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| DK1689233T3 (da) * | 2003-11-19 | 2012-10-15 | Array Biopharma Inc | Bicykliske inhibitorer af MEK |
| ES2299906T3 (es) | 2003-11-25 | 2008-06-01 | Eli Lilly And Company | Moduladores de receptores activados por proliferadores de peroxisomas. |
| AU2004299438A1 (en) | 2003-12-19 | 2005-06-30 | Biovitrum Ab | Novel benzofuran derivatives, which can be used in prophylaxis or treatment of 5-HT6 receptor-related disorder |
| ES2338060T3 (es) | 2003-12-22 | 2010-05-03 | Basilea Pharmaceutica Ag | Componentes de tipo ariloxi y ariltoxia-cetofenona para el tratamiento del cancer. |
| EP1699488A2 (en) | 2003-12-23 | 2006-09-13 | Pfizer Products Incorporated | Therapeutic combination for cognition enhancement and psychotic disorders |
| JP2009507024A (ja) | 2005-09-01 | 2009-02-19 | アレイ バイオファーマ、インコーポレイテッド | Ｒａｆ阻害剤化合物およびその使用方法 |
| EA025871B9 (ru) * | 2005-10-07 | 2017-08-31 | Экселиксис, Инк. | Ингибиторы mek и способы их применения |
| US20100063066A1 (en) | 2006-08-31 | 2010-03-11 | Array Biopharma, Inc. | Raf inhibitor compounds and methods of use thereof |
-
2009
- 2009-07-01 PE PE2010001198A patent/PE20110570A1/es not_active Application Discontinuation
- 2009-07-01 MX MX2010014559A patent/MX2010014559A/es active IP Right Grant
- 2009-07-01 EP EP09774475A patent/EP2310373A1/en not_active Withdrawn
- 2009-07-01 BR BRPI0910175A patent/BRPI0910175A2/pt not_active IP Right Cessation
- 2009-07-01 CA CA2727250A patent/CA2727250A1/en not_active Abandoned
- 2009-07-01 AU AU2009266956A patent/AU2009266956B2/en not_active Ceased
- 2009-07-01 JP JP2011516860A patent/JP5544358B2/ja not_active Expired - Fee Related
- 2009-07-01 CN CN200980133788.0A patent/CN102137847B/zh not_active Expired - Fee Related
- 2009-07-01 KR KR1020117002481A patent/KR20110029161A/ko not_active Application Discontinuation
- 2009-07-01 RU RU2011103454/04A patent/RU2509078C2/ru not_active IP Right Cessation
- 2009-07-01 US US12/999,003 patent/US8841462B2/en not_active Expired - Fee Related
- 2009-07-01 WO PCT/US2009/049453 patent/WO2010003025A1/en active Application Filing
-
2010
- 2010-12-12 IL IL209931A patent/IL209931A0/en unknown
- 2010-12-13 ZA ZA2010/08963A patent/ZA201008963B/en unknown
- 2010-12-30 CL CL2010001641A patent/CL2010001641A1/es unknown
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