JP2012512888A5 - - Google Patents
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- JP2012512888A5 JP2012512888A5 JP2011542421A JP2011542421A JP2012512888A5 JP 2012512888 A5 JP2012512888 A5 JP 2012512888A5 JP 2011542421 A JP2011542421 A JP 2011542421A JP 2011542421 A JP2011542421 A JP 2011542421A JP 2012512888 A5 JP2012512888 A5 JP 2012512888A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- hydrogen
- membered
- heteroatoms
- 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
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- 125000000217 alkyl group Chemical group 0.000 claims 48
- 229910052739 hydrogen Inorganic materials 0.000 claims 46
- 239000001257 hydrogen Substances 0.000 claims 46
- 125000005842 heteroatom Chemical group 0.000 claims 41
- 229910052760 oxygen Inorganic materials 0.000 claims 38
- 229910052717 sulfur Inorganic materials 0.000 claims 37
- 125000000623 heterocyclic group Chemical group 0.000 claims 35
- 150000002431 hydrogen Chemical class 0.000 claims 31
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 16
- 150000001875 compounds Chemical class 0.000 claims 16
- -1 ═O 2 Inorganic materials 0.000 claims 16
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 14
- 229910052731 fluorine Inorganic materials 0.000 claims 14
- 229910052794 bromium Inorganic materials 0.000 claims 13
- 229910052799 carbon Inorganic materials 0.000 claims 13
- 229910052801 chlorine Inorganic materials 0.000 claims 13
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000002757 morpholinyl group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000000335 thiazolyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000004193 piperazinyl group Chemical group 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 7
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 6
- 125000004432 carbon atom Chemical group C* 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 150000002367 halogens Chemical class 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 5
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 4
- 229910052796 boron Inorganic materials 0.000 claims 4
- 125000002950 monocyclic group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000001041 indolyl group Chemical group 0.000 claims 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims 3
- BNFOEMZRKYULDQ-UHFFFAOYSA-N 1-imidazolidin-1-ylimidazolidin-2-one Chemical compound O=C1NCCN1N1CNCC1 BNFOEMZRKYULDQ-UHFFFAOYSA-N 0.000 claims 2
- OOYREISBUILOLV-UHFFFAOYSA-N 3,4-dihydro-1,3-benzoxazin-2-one Chemical compound C1=CC=C2OC(=O)NCC2=C1 OOYREISBUILOLV-UHFFFAOYSA-N 0.000 claims 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 2
- 125000003016 chromanyl group Chemical group O1C(CCC2=CC=CC=C12)* 0.000 claims 2
- 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 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 2
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 2
- 201000006417 multiple sclerosis Diseases 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 2
- ROSODFDWJFAKQI-UHFFFAOYSA-N 1,2-dihydropyrrolo[3,4-c]pyridin-3-one Chemical compound C1=NC=C2C(=O)NCC2=C1 ROSODFDWJFAKQI-UHFFFAOYSA-N 0.000 claims 1
- WBNLAHSOVLAWCE-UHFFFAOYSA-N 1,3-dihydrofuro[3,4-c]pyridine Chemical compound N1=CC=C2COCC2=C1 WBNLAHSOVLAWCE-UHFFFAOYSA-N 0.000 claims 1
- GVUIEABSHOBWRY-UHFFFAOYSA-N 3-(1,3-oxazolidin-2-yl)-1,3-oxazolidin-2-one Chemical compound O=C1OCCN1C1OCCN1 GVUIEABSHOBWRY-UHFFFAOYSA-N 0.000 claims 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims 1
- MCPSVGWMYIXRQE-UHFFFAOYSA-N 7h-imidazo[1,2-a]pyrazin-8-one Chemical compound O=C1NC=CN2C=CN=C12 MCPSVGWMYIXRQE-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- 206010052779 Transplant rejections Diseases 0.000 claims 1
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000004602 benzodiazinyl group Chemical group N1=NC(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 claims 1
- 125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004619 benzopyranyl group Chemical group O1C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000004276 dioxalanyl group Chemical group 0.000 claims 1
- 125000005879 dioxolanyl group Chemical group 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
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- VDBNYAPERZTOOF-UHFFFAOYSA-N isoquinolin-1(2H)-one Chemical compound C1=CC=C2C(=O)NC=CC2=C1 VDBNYAPERZTOOF-UHFFFAOYSA-N 0.000 claims 1
- 125000005956 isoquinolyl group Chemical group 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000000160 oxazolidinyl group Chemical group 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 claims 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- VPDMWKMUFPCUBG-LICLKQGHSA-N CC/C(/C)=C(/C(CN)=O)\C1=CCc2cc(I)c(C)cc2N1 Chemical compound CC/C(/C)=C(/C(CN)=O)\C1=CCc2cc(I)c(C)cc2N1 VPDMWKMUFPCUBG-LICLKQGHSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13904708P | 2008-12-19 | 2008-12-19 | |
| US61/139,047 | 2008-12-19 | ||
| PCT/US2009/068415 WO2010080481A1 (en) | 2008-12-19 | 2009-12-17 | Carbazole carboxamide compounds useful as kinase inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012512888A JP2012512888A (ja) | 2012-06-07 |
| JP2012512888A5 true JP2012512888A5 (https=) | 2012-12-13 |
| JP5487214B2 JP5487214B2 (ja) | 2014-05-07 |
Family
ID=41622163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011542421A Expired - Fee Related JP5487214B2 (ja) | 2008-12-19 | 2009-12-17 | キナーゼ阻害剤として有用なカルバゾールカルボキシアミド化合物 |
Country Status (22)
| Country | Link |
|---|---|
| US (2) | US8084620B2 (https=) |
| EP (1) | EP2391602B1 (https=) |
| JP (1) | JP5487214B2 (https=) |
| KR (1) | KR20110098827A (https=) |
| CN (1) | CN102325753B (https=) |
| AR (1) | AR074812A1 (https=) |
| AU (1) | AU2009335821A1 (https=) |
| BR (1) | BRPI0922565A2 (https=) |
| CA (1) | CA2747670A1 (https=) |
| CL (1) | CL2011001516A1 (https=) |
| CO (1) | CO6390055A2 (https=) |
| EA (1) | EA019041B1 (https=) |
| ES (1) | ES2443948T3 (https=) |
| IL (1) | IL213185A0 (https=) |
| MX (1) | MX2011006171A (https=) |
| NZ (1) | NZ593096A (https=) |
| PE (1) | PE20110819A1 (https=) |
| SG (1) | SG171815A1 (https=) |
| TN (1) | TN2011000274A1 (https=) |
| TW (1) | TW201028401A (https=) |
| WO (1) | WO2010080481A1 (https=) |
| ZA (1) | ZA201104469B (https=) |
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| MX2008014450A (es) * | 2006-05-18 | 2009-03-09 | Mannkind Corp | Inhibidores de cinasa intracelular. |
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| PT2473049T (pt) | 2009-09-04 | 2019-03-04 | Sunesis Pharmaceuticals Inc | Inibidores de tirosina quinase de bruton |
| US8685969B2 (en) | 2010-06-16 | 2014-04-01 | Bristol-Myers Squibb Company | Carboline carboxamide compounds useful as kinase inhibitors |
| RU2556004C2 (ru) | 2011-01-25 | 2015-07-10 | Мицуй Кемикалс Агро, Инк. | Способ получения производного ароматического амида карбоновой кислоты |
| CN103582637B (zh) * | 2011-05-17 | 2015-08-12 | 弗·哈夫曼-拉罗切有限公司 | 酪氨酸激酶抑制剂 |
| WO2013156431A1 (en) | 2012-04-17 | 2013-10-24 | Syngenta Participations Ag | Pesticidally active pyridyl- and pyrimidyl- substituted thiazole and thiadiazole derivatives |
| AU2013250726B2 (en) | 2012-04-20 | 2017-01-05 | Advinus Therapeutics Limited | Substituted hetero-bicyclic compounds, compositions and medicinal applications thereof |
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| US9353087B2 (en) | 2012-06-08 | 2016-05-31 | Biogen Ma Inc. | Inhibitors of Bruton's tyrosine kinase |
| CN104704129A (zh) | 2012-07-24 | 2015-06-10 | 药品循环公司 | 与对布鲁顿酪氨酸激酶(btk)抑制剂的抗性相关的突变 |
| BR112015004666B1 (pt) * | 2012-09-07 | 2022-04-26 | Novartis Ag | Derivados de indol carboxamida, seu uso, e composição farmacêutica |
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| WO2014210087A1 (en) * | 2013-06-25 | 2014-12-31 | Bristol-Myers Squibb Company | Carbazole carboxamide compounds useful as kinase inhibitors |
| TWI648272B (zh) | 2013-06-25 | 2019-01-21 | 美商必治妥美雅史谷比公司 | 經取代之四氫咔唑及咔唑甲醯胺化合物 |
| JP6509838B2 (ja) * | 2013-06-26 | 2019-05-08 | アッヴィ・インコーポレイテッド | Ｂｔｋ阻害薬としての一級カルボキサミド類 |
| EA034666B1 (ru) | 2013-09-13 | 2020-03-04 | Бейджин Свитзерланд Гмбх | Антитело против pd-1 и его применение для лечения рака или вирусной инфекции и фрагмент антитела |
| WO2015110263A1 (en) * | 2014-01-21 | 2015-07-30 | Ac Immune Sa | Carbazole and carboline compounds for use in the diagnosis, treatment, alleviation or prevention of disorders associated with amyloid or amyolid-like proteins |
| PE20170247A1 (es) | 2014-05-15 | 2017-03-29 | Iteos Therapeutics | Derivados de pirrolidina-2,5-diona, composiciones farmaceuticas y metodos para usar como inhibidores ido1 |
| TWI726608B (zh) | 2014-07-03 | 2021-05-01 | 英屬開曼群島商百濟神州有限公司 | 抗pd-l1抗體及其作為治療及診斷之用途 |
| US10023576B2 (en) | 2014-10-22 | 2018-07-17 | Bristol-Myers Squibb Company | Heteroaryl substituted pyrrolotriazine amine compounds as PI3K inhibitors |
| US10214537B2 (en) | 2014-10-22 | 2019-02-26 | Bristol-Myers Squibb Company | Bicyclic heteroaryl amine compounds |
| SI3209651T1 (sl) | 2014-10-24 | 2019-12-31 | Bristol-Myers Squibb Company | Derivati karbazola |
| EA034931B1 (ru) | 2014-10-24 | 2020-04-08 | Бристол-Майерс Сквибб Компани | Индолкарбоксамидные соединения |
| JP6592512B2 (ja) * | 2014-10-24 | 2019-10-16 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | 三環式アトロプ異性体の化合物 |
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| EP3365334B1 (en) * | 2015-10-21 | 2024-07-17 | Otsuka Pharmaceutical Co., Ltd. | Benzolactam compounds as protein kinase inhibitors |
| CN105272903B (zh) * | 2015-11-17 | 2018-07-10 | 江苏师范大学 | 系列含氟咔唑类化合物及其制备方法和应用 |
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| KR102674902B1 (ko) | 2016-12-01 | 2024-06-14 | 아비나스 오퍼레이션스, 인코포레이티드 | 에스트로겐 수용체 분해제로서의 테트라히드로나프탈렌 및 테트라히드로이소퀴놀린 유도체 |
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| AU2017382870B2 (en) | 2016-12-22 | 2022-03-24 | Incyte Corporation | Benzooxazole derivatives as immunomodulators |
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- 2009-12-17 MX MX2011006171A patent/MX2011006171A/es active IP Right Grant
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- 2009-12-17 PE PE2011001234A patent/PE20110819A1/es not_active Application Discontinuation
- 2009-12-17 WO PCT/US2009/068415 patent/WO2010080481A1/en not_active Ceased
- 2009-12-17 SG SG2011037793A patent/SG171815A1/en unknown
- 2009-12-17 EP EP09793680.1A patent/EP2391602B1/en not_active Not-in-force
- 2009-12-17 KR KR1020117016659A patent/KR20110098827A/ko not_active Withdrawn
- 2009-12-17 CN CN200980157181.6A patent/CN102325753B/zh not_active Expired - Fee Related
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- 2009-12-17 ES ES09793680.1T patent/ES2443948T3/es active Active
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