CA2916504A1 - Carbazole carboxamide compounds useful as kinase inhibitors - Google Patents
Carbazole carboxamide compounds useful as kinase inhibitors Download PDFInfo
- Publication number
- CA2916504A1 CA2916504A1 CA2916504A CA2916504A CA2916504A1 CA 2916504 A1 CA2916504 A1 CA 2916504A1 CA 2916504 A CA2916504 A CA 2916504A CA 2916504 A CA2916504 A CA 2916504A CA 2916504 A1 CA2916504 A1 CA 2916504A1
- Authority
- CA
- Canada
- Prior art keywords
- carbazole
- carboxamide
- mixture
- dioxo
- mmol
- 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.)
- Abandoned
Links
- GFHHIWFKWFBNRU-UHFFFAOYSA-N 9h-carbazole-1-carboxamide Chemical class C12=CC=CC=C2NC2=C1C=CC=C2C(=O)N GFHHIWFKWFBNRU-UHFFFAOYSA-N 0.000 title description 6
- 229940043355 kinase inhibitor Drugs 0.000 title description 4
- 239000003757 phosphotransferase inhibitor Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 300
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 85
- 150000003839 salts Chemical class 0.000 claims abstract description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 29
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 25
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 18
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 6
- 238000011282 treatment Methods 0.000 claims description 38
- 239000003814 drug Substances 0.000 claims description 21
- 239000003937 drug carrier Substances 0.000 claims description 13
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 238000002560 therapeutic procedure Methods 0.000 claims description 4
- VIRRHNLXPOCKII-UHFFFAOYSA-N 4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(methoxymethyl)-9h-carbazole-1-carboxamide Chemical compound O=C1C=C2C(F)=CC=CN2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C(C=23)=CC=C(C=4)COC)C(N)=O)=CC=C1 VIRRHNLXPOCKII-UHFFFAOYSA-N 0.000 claims 4
- AXNKUCHUGAZVMO-UHFFFAOYSA-N 4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(F)C3=CC2=O)=O)=CC=C1 AXNKUCHUGAZVMO-UHFFFAOYSA-N 0.000 claims 3
- BPINSDADQGFXNS-UHFFFAOYSA-N 4-[2-chloro-3-(1-methyl-2,4-dioxoquinazolin-3-yl)phenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(Cl)C(N2C(=O)C3=CC=CC=C3N(C2=O)C)=CC=C1 BPINSDADQGFXNS-UHFFFAOYSA-N 0.000 claims 2
- KXUXXPNDCAWJHM-UHFFFAOYSA-N 4-[2-chloro-3-(8-fluoro-1-methyl-2,4-dioxoquinazolin-3-yl)phenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(Cl)C(N2C(=O)C3=CC=CC(F)=C3N(C2=O)C)=CC=C1 KXUXXPNDCAWJHM-UHFFFAOYSA-N 0.000 claims 2
- IWVCATOVLJOXMB-UHFFFAOYSA-N 4-[3-(4-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=CC3=C(F)C2=O)=O)=CC=C1 IWVCATOVLJOXMB-UHFFFAOYSA-N 0.000 claims 2
- FFVSEFDDGUYDFO-UHFFFAOYSA-N 4-[3-(5,7-dioxo-[1,3]thiazolo[3,2-c]pyrimidin-6-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CSC3=CC2=O)=O)=CC=C1 FFVSEFDDGUYDFO-UHFFFAOYSA-N 0.000 claims 2
- XAJGLHVYSGTVTF-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2,2-dimethylpropanoylamino)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(NC(=O)C(C)(C)C)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(Cl)C3=CC2=O)=O)=CC=C1 XAJGLHVYSGTVTF-UHFFFAOYSA-N 0.000 claims 2
- RXHAROKPHMWUME-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(Cl)C3=CC2=O)=O)=CC=C1 RXHAROKPHMWUME-UHFFFAOYSA-N 0.000 claims 2
- RNLHORWOBQSYJE-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(methoxymethyl)-9h-carbazole-1-carboxamide Chemical compound O=C1C=C2C(Cl)=CC=CN2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C(C=23)=CC=C(C=4)COC)C(N)=O)=CC=C1 RNLHORWOBQSYJE-UHFFFAOYSA-N 0.000 claims 2
- BEKXRKQECXXKGJ-UHFFFAOYSA-N 4-[3-(5-chloro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(pyrrolidin-1-ylmethyl)-9h-carbazole-1-carboxamide Chemical compound C1=CC=C(N2C(N3C=CC=C(Cl)C3=CC2=O)=O)C(C)=C1C(C=1C2=CC=3)=CC=C(C(N)=O)C=1NC2=CC=3CN1CCCC1 BEKXRKQECXXKGJ-UHFFFAOYSA-N 0.000 claims 2
- JPJRIRSPLLYPRY-UHFFFAOYSA-N 4-[3-(5-fluoro-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-7-(hydroxymethyl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(CO)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(N3C=CC=C(F)C3=CC2=O)=O)=CC=C1 JPJRIRSPLLYPRY-UHFFFAOYSA-N 0.000 claims 2
- KQUDGOWUGZTCKG-UHFFFAOYSA-N 4-[3-(6-fluoro-1-methyl-2,4-dioxoquinazolin-3-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(C3=CC(F)=CC=C3N(C)C2=O)=O)=CC=C1 KQUDGOWUGZTCKG-UHFFFAOYSA-N 0.000 claims 2
- BEVUBRZINAWGDH-UHFFFAOYSA-N 4-[3-(8-fluoro-1-methyl-2,4-dioxoquinazolin-3-yl)-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-5-methyl-9h-carbazole-1-carboxamide Chemical compound O=C1N(C)C2=C(F)C=CC=C2C(=O)N1C1=C(C)C(C=2C=CC(=C3NC=4C=C(C=C(C=4C3=2)C)C(C)(C)O)C(N)=O)=CC=C1 BEVUBRZINAWGDH-UHFFFAOYSA-N 0.000 claims 2
- OPCHAIUSSHIEQR-UHFFFAOYSA-N 4-[3-[3-(4-fluorophenyl)-2,6-dioxopyrimidin-1-yl]-2-methylphenyl]-7-(2-hydroxypropan-2-yl)-9h-carbazole-1-carboxamide Chemical compound CC1=C(C=2C=3C4=CC=C(C=C4NC=3C(C(N)=O)=CC=2)C(C)(C)O)C=CC=C1N(C1=O)C(=O)C=CN1C1=CC=C(F)C=C1 OPCHAIUSSHIEQR-UHFFFAOYSA-N 0.000 claims 2
- YSLQGJFYBNLPDI-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(5-methoxy-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)C=C3N(C2=O)C=CC=C3OC)=CC=C1 YSLQGJFYBNLPDI-UHFFFAOYSA-N 0.000 claims 2
- HPPFVYVYCRLUIG-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(6-methoxy-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)C=C3N(C2=O)C=CC(=C3)OC)=CC=C1 HPPFVYVYCRLUIG-UHFFFAOYSA-N 0.000 claims 2
- HMFXPCSTCHRNIX-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(7-methoxy-1,3-dioxopyrido[1,2-c]pyrimidin-2-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)C=C3C=CC(=CN3C2=O)OC)=CC=C1 HMFXPCSTCHRNIX-UHFFFAOYSA-N 0.000 claims 2
- RAGWYGVSFHQCQZ-UHFFFAOYSA-N 7-(2-hydroxypropan-2-yl)-4-[3-(8-methoxy-1-methyl-2,4-dioxoquinazolin-3-yl)-2-methylphenyl]-9h-carbazole-1-carboxamide Chemical compound N1C2=CC(C(C)(C)O)=CC=C2C2=C1C(C(N)=O)=CC=C2C1=C(C)C(N2C(=O)N(C)C3=C(C2=O)C=CC=C3OC)=CC=C1 RAGWYGVSFHQCQZ-UHFFFAOYSA-N 0.000 claims 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
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- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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| US61/839,130 | 2013-06-25 | ||
| PCT/US2014/043980 WO2014210087A1 (en) | 2013-06-25 | 2014-06-25 | Carbazole carboxamide compounds useful as kinase inhibitors |
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| CA2916504A1 true CA2916504A1 (en) | 2014-12-31 |
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| PE20171239A1 (es) | 2014-10-24 | 2017-08-24 | Bristol Myers Squibb Co | Derivados de carbazol |
| HUE050706T2 (hu) | 2014-10-24 | 2020-12-28 | Bristol Myers Squibb Co | Indol karboxamid vegyületek, amelyek hasznosak kináz inhibitorokként |
| CN105802100A (zh) * | 2016-04-22 | 2016-07-27 | 宁波硫华聚合物有限公司 | 橡胶促进剂粘合剂六甲氧基甲基蜜胺预分散母胶粒及其制备方法 |
| CN105694150A (zh) * | 2016-04-25 | 2016-06-22 | 无锡智谷锐拓技术服务有限公司 | 一种耐油橡胶 |
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| CN105907150A (zh) * | 2016-06-02 | 2016-08-31 | 扬州兰都塑料科技有限公司 | 一种电缆涂料用阻燃剂 |
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| CN115335380B (zh) | 2020-02-03 | 2024-08-02 | 百时美施贵宝公司 | 可用作irak4抑制剂的三环杂芳基化合物 |
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| CA2140722A1 (en) | 1994-01-24 | 1995-07-25 | Joseph A. Jakubowski | Beta-carboline thromboxane synthase inhibitors |
| US7405295B2 (en) | 2003-06-04 | 2008-07-29 | Cgi Pharmaceuticals, Inc. | Certain imidazo[1,2-a]pyrazin-8-ylamines and method of inhibition of Bruton's tyrosine kinase by such compounds |
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2014
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- 2014-06-25 AU AU2014302550A patent/AU2014302550A1/en not_active Abandoned
- 2014-06-25 SG SG11201510028PA patent/SG11201510028PA/en unknown
- 2014-06-25 WO PCT/US2014/043980 patent/WO2014210087A1/en not_active Ceased
- 2014-06-25 EA EA201690012A patent/EA025863B1/ru not_active IP Right Cessation
- 2014-06-25 CN CN201480046669.2A patent/CN105473573B/zh not_active Expired - Fee Related
- 2014-06-25 CA CA2916504A patent/CA2916504A1/en not_active Abandoned
- 2014-06-25 JP JP2016523870A patent/JP6353530B2/ja not_active Expired - Fee Related
- 2014-06-25 MX MX2015016771A patent/MX2015016771A/es unknown
- 2014-06-25 BR BR112015031432A patent/BR112015031432A2/pt not_active Application Discontinuation
- 2014-06-25 US US14/392,355 patent/US9714234B2/en active Active
- 2014-06-25 KR KR1020167001634A patent/KR102345381B1/ko not_active Expired - Fee Related
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2015
- 2015-12-22 IL IL243295A patent/IL243295A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL243295A0 (en) | 2016-02-29 |
| MX2015016771A (es) | 2016-03-31 |
| BR112015031432A2 (pt) | 2017-07-25 |
| US20160200710A1 (en) | 2016-07-14 |
| KR20160022890A (ko) | 2016-03-02 |
| EA025863B1 (ru) | 2017-02-28 |
| WO2014210087A1 (en) | 2014-12-31 |
| US9714234B2 (en) | 2017-07-25 |
| JP6353530B2 (ja) | 2018-07-04 |
| SG11201510028PA (en) | 2016-01-28 |
| EA201690012A1 (ru) | 2016-05-31 |
| EP3013815B1 (en) | 2017-05-03 |
| EP3013815A1 (en) | 2016-05-04 |
| JP2016523908A (ja) | 2016-08-12 |
| CN105473573A (zh) | 2016-04-06 |
| KR102345381B1 (ko) | 2021-12-29 |
| AU2014302550A1 (en) | 2016-02-11 |
| CN105473573B (zh) | 2018-03-16 |
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