HRP20030081A2 - Benzimidazole derivatives, preparation and therapeutic use thereof - Google Patents
Benzimidazole derivatives, preparation and therapeutic use thereof Download PDFInfo
- Publication number
- HRP20030081A2 HRP20030081A2 HR20030081A HRP20030081A HRP20030081A2 HR P20030081 A2 HRP20030081 A2 HR P20030081A2 HR 20030081 A HR20030081 A HR 20030081A HR P20030081 A HRP20030081 A HR P20030081A HR P20030081 A2 HRP20030081 A2 HR P20030081A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- hydrogen atom
- quinolin
- alkyl group
- dihydro
- Prior art date
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- 238000002360 preparation method Methods 0.000 title description 12
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 title description 2
- 230000001225 therapeutic effect Effects 0.000 title description 2
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 118
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 69
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 56
- 239000000203 mixture Substances 0.000 claims description 52
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- -1 aminopyridyl Chemical group 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 24
- 229910052799 carbon Chemical group 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 18
- 125000004076 pyridyl group Chemical group 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 239000000543 intermediate Substances 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- VPXJSTOFWHBSEJ-UHFFFAOYSA-N 5h-quinolin-6-one Chemical compound C1=CN=C2C=CC(=O)CC2=C1 VPXJSTOFWHBSEJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000003277 amino group Chemical group 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
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- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
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- 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 description 6
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- JUPJLRHBPREHBT-UHFFFAOYSA-N 2-[4-(4-methoxyphenyl)piperazin-1-yl]-1,3-diazatricyclo[6.3.1.04,12]dodeca-2,4,6,8(12)-tetraen-9-one Chemical compound C1=CC(OC)=CC=C1N1CCN(C=2N3CCC(=O)C=4C=CC=C(C3=4)N=2)CC1 JUPJLRHBPREHBT-UHFFFAOYSA-N 0.000 claims 1
- 201000011040 acute kidney failure Diseases 0.000 claims 1
- 208000012998 acute renal failure Diseases 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 120
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
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- 239000000243 solution Substances 0.000 description 31
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Classifications
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- 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
- C07D471/06—Peri-condensed systems
-
- A—HUMAN NECESSITIES
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0010419A FR2812878B1 (fr) | 2000-08-08 | 2000-08-08 | Derives de benzimidazole, leur preparation et leur application en therapeutique |
| FR0014696A FR2816619B1 (fr) | 2000-11-15 | 2000-11-15 | Derives de benzimidazole, leur preparation et leur application en therapeutique |
| PCT/FR2001/002556 WO2002012239A1 (fr) | 2000-08-08 | 2001-08-06 | Derives de benzimidazole, leur preparation et leur application en therapeutique |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20030081A2 true HRP20030081A2 (en) | 2005-02-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| HR20030081A HRP20030081A2 (en) | 2000-08-08 | 2003-02-06 | Benzimidazole derivatives, preparation and therapeutic use thereof |
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| Country | Link |
|---|---|
| US (2) | US6794382B2 (no) |
| EP (1) | EP1309594B1 (no) |
| JP (1) | JP2004505975A (no) |
| KR (1) | KR20030020450A (no) |
| CN (1) | CN1446218A (no) |
| AR (1) | AR030121A1 (no) |
| AT (1) | ATE284886T1 (no) |
| AU (1) | AU2001282267A1 (no) |
| BG (1) | BG107460A (no) |
| BR (1) | BR0113046A (no) |
| CA (1) | CA2412368A1 (no) |
| CZ (1) | CZ294493B6 (no) |
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| EE (1) | EE200300048A (no) |
| ES (1) | ES2233671T3 (no) |
| HK (1) | HK1053118A1 (no) |
| HR (1) | HRP20030081A2 (no) |
| HU (1) | HUP0301514A2 (no) |
| IL (1) | IL153708A0 (no) |
| IS (1) | IS6661A (no) |
| MX (1) | MXPA03000753A (no) |
| NO (1) | NO20030596L (no) |
| PL (1) | PL365080A1 (no) |
| PT (1) | PT1309594E (no) |
| SK (1) | SK1582003A3 (no) |
| WO (1) | WO2002012239A1 (no) |
| YU (1) | YU7203A (no) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US20050119251A1 (en) * | 2001-12-21 | 2005-06-02 | Jian-Min Fu | Nicotinamide derivatives and their use as therapeutic agents |
| US20040014744A1 (en) * | 2002-04-05 | 2004-01-22 | Fortuna Haviv | Substituted pyridines having antiangiogenic activity |
| WO2003103666A2 (en) * | 2002-06-07 | 2003-12-18 | Altana Pharma Ag | Novel 4,5-dihydro-imidazo[4,5,1-ij]quinolin-6-ones |
| AU2003240742A1 (en) * | 2002-06-07 | 2003-12-22 | Altana Pharma Ag | 4,5-dihydro-imidazo (4,5,1-ij) quinolin-6-ones derivatives and their use as poly (adp-ribosyl) transferase (parp) inhibitors |
| WO2004108723A1 (en) * | 2003-06-04 | 2004-12-16 | Altana Pharma Ag | 4,5-dihydro-imidazo[4,5,1-ii]quinolin-6-ones as parp inhibitors |
| GB0317466D0 (en) * | 2003-07-25 | 2003-08-27 | Univ Sheffield | Use |
| ES2371469T3 (es) | 2003-12-01 | 2012-01-03 | Kudos Pharmaceuticals Limited | Inhibidores de reparación de daños en adn para el tratamiento del cáncer. |
| US20080167321A1 (en) * | 2004-09-20 | 2008-07-10 | Xenon Pharmaceuticals Inc. | Pyridine Derivatives For Inhibiting Human Stearoyl-Coa-Desaturase |
| CA2580845A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Pyridazine derivatives for inhibiting human stearoyl-coa-desaturase |
| BRPI0515483A (pt) | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos para o tratamento de doenças mediadas por enzimas estearoil-coa desaturase |
| MX2007003325A (es) | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores estearoil-coa-desaturasa. |
| BRPI0515478A (pt) * | 2004-09-20 | 2008-07-22 | Xenon Pharmaceuticals Inc | derivados heterocìclicos e seu uso como mediadores de estearoil-coa-desaturase |
| AR051294A1 (es) * | 2004-09-20 | 2007-01-03 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como inhibidores de la estearoil-coa desaturasa |
| AU2005286648A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-CoA desaturase inhibitors |
| CA2580762A1 (en) * | 2004-09-20 | 2006-03-30 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as therapeutic agents |
| WO2006101521A2 (en) * | 2004-09-20 | 2006-09-28 | Xenon Pharmaceuticals Inc. | Heterocyclic derivatives and their use as stearoyl-coa desaturase inhibitors |
| US7842817B2 (en) | 2005-01-11 | 2010-11-30 | Neurosearch A/S | 2-amino benzimidazole derivatives and their use as modulators of small-conductance calcium-activated potassium channels |
| CN101208089A (zh) * | 2005-06-03 | 2008-06-25 | 泽农医药公司 | 氨基噻唑衍生物作为人硬酯酰-CoA去饱和酶抑制剂 |
| CN101268077A (zh) * | 2005-08-05 | 2008-09-17 | 阿斯利康(瑞典)有限公司 | 三环苯并咪唑及其作为代谢型谷氨酸受体调节剂的用途 |
| JP2009541454A (ja) * | 2006-07-03 | 2009-11-26 | ノイロサーチ アクティーゼルスカブ | モノアミン再摂取阻害剤及びカリウムチャネル活性剤の併用 |
| GB0716532D0 (en) | 2007-08-24 | 2007-10-03 | Angeletti P Ist Richerche Bio | Therapeutic compounds |
| GB201220157D0 (en) * | 2012-11-08 | 2012-12-26 | Selvita Sa | Substitute tricyclic benzimidazoles as kinase inhibitors |
| CN103923088B (zh) * | 2013-01-11 | 2016-09-07 | 上海汇伦生命科技有限公司 | 2,5-二氮杂双环[2.2.1]庚烷类化合物和制备方法、其药用组合物及其在医药上的应用 |
| ES2755827T3 (es) | 2013-03-15 | 2020-04-23 | Incyte Holdings Corp | Heterciclos tricíclicos como inhibidores de proteína BET |
| CN104230896A (zh) | 2013-06-17 | 2014-12-24 | 上海汇伦生命科技有限公司 | 苯并咪唑-2-哌嗪杂环类化合物、其药物组合物及其制备方法和用途 |
| US9309246B2 (en) | 2013-12-19 | 2016-04-12 | Incyte Corporation | Tricyclic heterocycles as BET protein inhibitors |
| RS64231B1 (sr) | 2014-04-23 | 2023-06-30 | Incyte Holdings Corp | 1h-pirolo[2,3-c]piridin-7(6h)-on i pirazolo[3,4-c]piridin-7(6h)-on kao inhibitori bet proteina |
| JP6614585B2 (ja) * | 2015-05-29 | 2019-12-04 | 塩野義製薬株式会社 | Ｈｉｖ複製阻害作用を有する含窒素３環性誘導体 |
| EP3472157B1 (en) | 2016-06-20 | 2023-04-12 | Incyte Corporation | Crystalline solid forms of a bet inhibitor |
| CN110661676B (zh) * | 2018-06-29 | 2022-06-28 | 大唐移动通信设备有限公司 | 一种带宽部分的测量方法、配置方法、终端及网络设备 |
| CN111349094B (zh) * | 2020-04-23 | 2021-02-02 | 杭州师范大学 | 一种6H-咪唑[4,5,1-ij]并喹诺酮及其合成方法和应用 |
| US11833155B2 (en) | 2020-06-03 | 2023-12-05 | Incyte Corporation | Combination therapy for treatment of myeloproliferative neoplasms |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2710915B1 (fr) * | 1993-10-04 | 1995-11-24 | Synthelabo | Dérivés de pipéridine, leur préparation et leur utilisation en thérapeutique. |
| FR2731708B1 (fr) | 1995-03-13 | 1997-04-30 | Synthelabo | Derives de piperidine, leur procede de preparation et leur application en therapeutique |
| CZ300148B6 (cs) * | 1998-11-27 | 2009-02-25 | Abbott Gmbh & Co. Kg | Derivát substituovaného benzimidazolu, zpusob jeho prípravy a jeho použití |
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2001
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- 2001-08-06 EP EP01960871A patent/EP1309594B1/fr not_active Expired - Lifetime
- 2001-08-06 PT PT01960871T patent/PT1309594E/pt unknown
- 2001-08-06 PL PL01365080A patent/PL365080A1/xx not_active Application Discontinuation
- 2001-08-06 AT AT01960871T patent/ATE284886T1/de not_active IP Right Cessation
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- 2001-08-06 BR BR0113046-3A patent/BR0113046A/pt not_active IP Right Cessation
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- 2001-08-06 AR ARP010103751A patent/AR030121A1/es not_active Application Discontinuation
- 2001-08-06 US US10/343,467 patent/US6794382B2/en not_active Expired - Fee Related
- 2001-08-06 JP JP2002518214A patent/JP2004505975A/ja active Pending
- 2001-08-06 MX MXPA03000753A patent/MXPA03000753A/es unknown
- 2001-08-06 YU YU7203A patent/YU7203A/sh unknown
- 2001-08-06 HU HU0301514A patent/HUP0301514A2/hu unknown
- 2001-08-06 AU AU2001282267A patent/AU2001282267A1/en not_active Abandoned
- 2001-08-06 WO PCT/FR2001/002556 patent/WO2002012239A1/fr active IP Right Grant
- 2001-08-06 ES ES01960871T patent/ES2233671T3/es not_active Expired - Lifetime
- 2001-08-06 CA CA002412368A patent/CA2412368A1/fr not_active Abandoned
- 2001-08-06 DE DE60107859T patent/DE60107859T2/de not_active Expired - Lifetime
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2002
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2003
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- 2003-02-06 NO NO20030596A patent/NO20030596L/no not_active Application Discontinuation
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2004
- 2004-09-13 US US10/939,910 patent/US20050032779A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
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| PT1309594E (pt) | 2005-04-29 |
| IL153708A0 (en) | 2003-07-06 |
| AR030121A1 (es) | 2003-08-13 |
| HUP0301514A2 (hu) | 2003-09-29 |
| HK1053118A1 (en) | 2003-10-10 |
| WO2002012239A1 (fr) | 2002-02-14 |
| CZ2003354A3 (cs) | 2003-05-14 |
| DE60107859D1 (de) | 2005-01-20 |
| PL365080A1 (en) | 2004-12-27 |
| EP1309594A1 (fr) | 2003-05-14 |
| US20030203893A1 (en) | 2003-10-30 |
| EA200201259A1 (ru) | 2003-06-26 |
| MXPA03000753A (es) | 2003-10-15 |
| EP1309594B1 (fr) | 2004-12-15 |
| DE60107859T2 (de) | 2005-12-22 |
| NO20030596L (no) | 2003-04-01 |
| CZ294493B6 (cs) | 2005-01-12 |
| US6794382B2 (en) | 2004-09-21 |
| EE200300048A (et) | 2004-12-15 |
| YU7203A (sh) | 2006-01-16 |
| BR0113046A (pt) | 2003-07-01 |
| US20050032779A1 (en) | 2005-02-10 |
| EA005950B1 (ru) | 2005-08-25 |
| SK1582003A3 (en) | 2003-08-05 |
| BG107460A (bg) | 2003-09-30 |
| NO20030596D0 (no) | 2003-02-06 |
| JP2004505975A (ja) | 2004-02-26 |
| CN1446218A (zh) | 2003-10-01 |
| CA2412368A1 (fr) | 2002-02-14 |
| IS6661A (is) | 2002-12-19 |
| AU2001282267A1 (en) | 2002-02-18 |
| ATE284886T1 (de) | 2005-01-15 |
| ES2233671T3 (es) | 2005-06-16 |
| KR20030020450A (ko) | 2003-03-08 |
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