JP2014521705A5 - - Google Patents
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- Publication number
- JP2014521705A5 JP2014521705A5 JP2014524284A JP2014524284A JP2014521705A5 JP 2014521705 A5 JP2014521705 A5 JP 2014521705A5 JP 2014524284 A JP2014524284 A JP 2014524284A JP 2014524284 A JP2014524284 A JP 2014524284A JP 2014521705 A5 JP2014521705 A5 JP 2014521705A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- amide
- benzimidazol
- cyclopropanecarboxylic acid
- formula
- 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
- 239000000203 mixture Substances 0.000 claims 18
- 230000001419 dependent effect Effects 0.000 claims 12
- 229910052739 hydrogen Inorganic materials 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- MGVCJDUADZGAFE-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(2-chlorophenyl)cyclopropane-1-carboxamide Chemical compound ClC1=CC=CC=C1C1C(C(=O)NC=2NC3=CC=CC=C3N=2)C1 MGVCJDUADZGAFE-UHFFFAOYSA-N 0.000 claims 6
- FOQUERCPDVTVEK-UHFFFAOYSA-N n-(4-chloro-1h-imidazo[4,5-c]pyridin-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N1C=2C(Cl)=NC=CC=2N=C1NC(=O)C1CC1C1=CC=CC=C1 FOQUERCPDVTVEK-UHFFFAOYSA-N 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- HZGWRKOFUDOOLU-UHFFFAOYSA-N n-(6-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC(Cl)=CN=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 HZGWRKOFUDOOLU-UHFFFAOYSA-N 0.000 claims 4
- LSWJBLLZGKDWMB-UHFFFAOYSA-N n-(6-cyano-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC(C#N)=CC=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 LSWJBLLZGKDWMB-UHFFFAOYSA-N 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- XSXXRSFZRDHQNQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-(6-cyano-1h-benzimidazol-2-yl)cyclopropane-1-carboxamide Chemical compound ClC1=CC=CC=C1C1C(C(=O)NC=2NC3=CC(=CC=C3N=2)C#N)C1 XSXXRSFZRDHQNQ-UHFFFAOYSA-N 0.000 claims 2
- ODNXCMPSVSKQJG-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C2=CC(C(F)(F)F)=CC=C2N=C1NC(=O)C1CC1C1=CC=CC=C1Cl ODNXCMPSVSKQJG-UHFFFAOYSA-N 0.000 claims 2
- FWLLGFWJIGDNEX-UHFFFAOYSA-N 2-phenyl-n-[6-(trifluoromethyl)-1h-benzimidazol-2-yl]cyclopropane-1-carboxamide Chemical compound N1C2=CC(C(F)(F)F)=CC=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 FWLLGFWJIGDNEX-UHFFFAOYSA-N 0.000 claims 2
- 125000001931 aliphatic group Chemical group 0.000 claims 2
- 230000033115 angiogenesis Effects 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- SLEOUAYKERAFGV-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(3-bromophenyl)cyclopropane-1-carboxamide Chemical compound BrC1=CC=CC(C2C(C2)C(=O)NC=2NC3=CC=CC=C3N=2)=C1 SLEOUAYKERAFGV-UHFFFAOYSA-N 0.000 claims 2
- JMGGZIGMGLACDQ-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide Chemical compound FC1=CC=CC(C2C(C2)C(=O)NC=2NC3=CC=CC=C3N=2)=C1 JMGGZIGMGLACDQ-UHFFFAOYSA-N 0.000 claims 2
- KKLDCFFHHFOJQG-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(3-methylphenyl)cyclopropane-1-carboxamide Chemical compound CC1=CC=CC(C2C(C2)C(=O)NC=2NC3=CC=CC=C3N=2)=C1 KKLDCFFHHFOJQG-UHFFFAOYSA-N 0.000 claims 2
- QUUAFAHVCBDKMO-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(3-nitrophenyl)cyclopropane-1-carboxamide Chemical compound [O-][N+](=O)C1=CC=CC(C2C(C2)C(=O)NC=2NC3=CC=CC=C3N=2)=C1 QUUAFAHVCBDKMO-UHFFFAOYSA-N 0.000 claims 2
- YHNNCTAUSKHMJT-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(4-fluorophenyl)cyclopropane-1-carboxamide Chemical compound C1=CC(F)=CC=C1C1C(C(=O)NC=2NC3=CC=CC=C3N=2)C1 YHNNCTAUSKHMJT-UHFFFAOYSA-N 0.000 claims 2
- JIPVBLDRCKYYAL-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-(5-bromo-2-fluorophenyl)cyclopropane-1-carboxamide Chemical compound FC1=CC=C(Br)C=C1C1C(C(=O)NC=2NC3=CC=CC=C3N=2)C1 JIPVBLDRCKYYAL-UHFFFAOYSA-N 0.000 claims 2
- XSIZKMVNFSTJAG-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 XSIZKMVNFSTJAG-UHFFFAOYSA-N 0.000 claims 2
- YSDKIBXLLIFMLE-UHFFFAOYSA-N n-(1h-imidazo[4,5-b]pyridin-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC=CN=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 YSDKIBXLLIFMLE-UHFFFAOYSA-N 0.000 claims 2
- WRGCYNGTPRTSKY-UHFFFAOYSA-N n-(4-amino-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C=2C(N)=CC=CC=2NC=1NC(=O)C1CC1C1=CC=CC=C1 WRGCYNGTPRTSKY-UHFFFAOYSA-N 0.000 claims 2
- ICZDSMZPXANWFZ-UHFFFAOYSA-N n-(4-nitro-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C=2C([N+](=O)[O-])=CC=CC=2NC=1NC(=O)C1CC1C1=CC=CC=C1 ICZDSMZPXANWFZ-UHFFFAOYSA-N 0.000 claims 2
- NRHGNXZUNHSEFL-UHFFFAOYSA-N n-(5,6-dimethyl-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1NC(=O)C1CC1C1=CC=CC=C1 NRHGNXZUNHSEFL-UHFFFAOYSA-N 0.000 claims 2
- NOTNYUBHCNDKJJ-UHFFFAOYSA-N n-(6-bromo-1h-imidazo[4,5-b]pyridin-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC(Br)=CN=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 NOTNYUBHCNDKJJ-UHFFFAOYSA-N 0.000 claims 2
- RBMCRCWDYDLOIY-UHFFFAOYSA-N n-(6-chloro-1h-benzimidazol-2-yl)-2,2-difluoro-3-phenylcyclopropane-1-carboxamide Chemical compound FC1(F)C(C(=O)NC=2NC3=CC(Cl)=CC=C3N=2)C1C1=CC=CC=C1 RBMCRCWDYDLOIY-UHFFFAOYSA-N 0.000 claims 2
- YUYWNWMJKMVZLQ-UHFFFAOYSA-N n-(6-chloro-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N1C2=CC(Cl)=CC=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 YUYWNWMJKMVZLQ-UHFFFAOYSA-N 0.000 claims 2
- LAEYKNJBAMXJAP-UHFFFAOYSA-N n-(6-chloro-1h-imidazo[4,5-b]pyridin-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide Chemical compound FC1=CC=CC(C2C(C2)C(=O)NC=2NC3=NC=C(Cl)C=C3N=2)=C1 LAEYKNJBAMXJAP-UHFFFAOYSA-N 0.000 claims 2
- WJLLQIQKNCGRIU-UHFFFAOYSA-N n-(6-cyano-1h-benzimidazol-2-yl)-2-(3-fluorophenyl)cyclopropane-1-carboxamide Chemical compound FC1=CC=CC(C2C(C2)C(=O)NC=2NC3=CC(=CC=C3N=2)C#N)=C1 WJLLQIQKNCGRIU-UHFFFAOYSA-N 0.000 claims 2
- IVBUXTTTWZFBRS-UHFFFAOYSA-N n-(6-ethyl-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC(CC)=CC=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 IVBUXTTTWZFBRS-UHFFFAOYSA-N 0.000 claims 2
- YGTRXGSEHCHETH-UHFFFAOYSA-N n-(6-methoxy-1h-benzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC(OC)=CC=C2NC=1NC(=O)C1CC1C1=CC=CC=C1 YGTRXGSEHCHETH-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- JMXSIVSSGVIPKE-UHFFFAOYSA-N 1-(1-propylbenzimidazol-2-yl)cyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2N(CCC)C=1C1(C(N)=O)CC1 JMXSIVSSGVIPKE-UHFFFAOYSA-N 0.000 claims 1
- UDJATMXEQPFERC-UHFFFAOYSA-N 2-(4-chlorophenyl)-n-(1-methylbenzimidazol-2-yl)cyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2N(C)C=1NC(=O)C1CC1C1=CC=C(Cl)C=C1 UDJATMXEQPFERC-UHFFFAOYSA-N 0.000 claims 1
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 1
- 206010016654 Fibrosis Diseases 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004761 fibrosis Effects 0.000 claims 1
- 206010020718 hyperplasia Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 208000002780 macular degeneration Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- CPXXGNZCEDRJPC-UHFFFAOYSA-N n-(1-ethylbenzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2N(CC)C=1NC(=O)C1CC1C1=CC=CC=C1 CPXXGNZCEDRJPC-UHFFFAOYSA-N 0.000 claims 1
- DSOYXNGSPYIUIX-UHFFFAOYSA-N n-(1-methylbenzimidazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2N(C)C=1NC(=O)C1CC1C1=CC=CC=C1 DSOYXNGSPYIUIX-UHFFFAOYSA-N 0.000 claims 1
- QRYLQVWEMZNPPL-UHFFFAOYSA-N n-(1h-benzimidazol-2-yl)-1-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2NC=1NC(=O)C1(C=2C=CC=CC=2)CC1 QRYLQVWEMZNPPL-UHFFFAOYSA-N 0.000 claims 1
- OWNBLAOPYHELRJ-UHFFFAOYSA-N n-(6-methylsulfonyl-1,3-benzothiazol-2-yl)-2-phenylcyclopropane-1-carboxamide Chemical compound S1C2=CC(S(=O)(=O)C)=CC=C2N=C1NC(=O)C1CC1C1=CC=CC=C1 OWNBLAOPYHELRJ-UHFFFAOYSA-N 0.000 claims 1
- SYSPJOSGUHVHJH-UHFFFAOYSA-N n-[1-[2-(diethylamino)ethyl]benzimidazol-2-yl]-2-phenylcyclopropane-1-carboxamide Chemical compound N=1C2=CC=CC=C2N(CCN(CC)CC)C=1NC(=O)C1CC1C1=CC=CC=C1 SYSPJOSGUHVHJH-UHFFFAOYSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 208000014265 psoriasis 10 Diseases 0.000 claims 1
- 208000037803 restenosis Diseases 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 230000005747 tumor angiogenesis Effects 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11006501 | 2011-08-08 | ||
| EP11006501.8 | 2011-08-08 | ||
| PCT/EP2012/002874 WO2013020622A1 (en) | 2011-08-08 | 2012-07-07 | N-(benzimimdazol-2-yl)-cyclopropane carboxamides as lysophosphatidic acid antagonists |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014521705A JP2014521705A (ja) | 2014-08-28 |
| JP2014521705A5 true JP2014521705A5 (enExample) | 2015-08-27 |
| JP5978302B2 JP5978302B2 (ja) | 2016-08-24 |
Family
ID=46489167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014524284A Expired - Fee Related JP5978302B2 (ja) | 2011-08-08 | 2012-07-07 | リゾホスファチジン酸アンタゴニストとしての（ｎ−ベンズイミダゾール−２−イル）−シクロプロパンカルボキサミド |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US8912202B2 (enExample) |
| EP (1) | EP2742029B1 (enExample) |
| JP (1) | JP5978302B2 (enExample) |
| CN (1) | CN103702984B (enExample) |
| AU (1) | AU2012292649B8 (enExample) |
| CA (1) | CA2844469C (enExample) |
| ES (1) | ES2609003T3 (enExample) |
| IL (1) | IL230835B (enExample) |
| WO (1) | WO2013020622A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9062013B2 (en) | 2011-02-02 | 2015-06-23 | Bionomics Limited | Positive allosteric modulators of the α7 nicotinic acetylcholine receptor and uses thereof |
| WO2017165256A1 (en) | 2016-03-22 | 2017-09-28 | Merck Sharp & Dohme Corp. | Allosteric modulators of nicotinic acetylcholine receptors |
| CN106291783B (zh) * | 2016-08-19 | 2018-01-09 | 天通（嘉兴）新材料有限公司 | 杀菌镀膜膜层结构及其制备方法 |
| CN109589325B (zh) * | 2019-02-19 | 2019-11-26 | 牡丹江医学院 | 一种用于治疗肠炎的药物组合物及其制备方法 |
| US11618751B1 (en) | 2022-03-25 | 2023-04-04 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 derivatives |
| US11319319B1 (en) | 2021-04-07 | 2022-05-03 | Ventus Therapeutics U.S., Inc. | Compounds for inhibiting NLRP3 and uses thereof |
| CN115108905B (zh) * | 2022-07-01 | 2025-04-08 | 湖南大学 | 铜催化羧酸的区域选择性烯烃化和三氟甲基化生成(z)-三氟甲烷烯醇酯的方法 |
| US12331048B2 (en) | 2022-10-31 | 2025-06-17 | Ventus Therapeutics U.S., Inc. | Pyrido-[3,4-d]pyridazine amine derivatives useful as NLRP3 inhibitors |
| CN116514897B (zh) * | 2023-05-09 | 2024-03-29 | 暨南大学 | 环丙烷或者环丙烯类化合物及其应用 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1294685A1 (en) * | 2000-06-29 | 2003-03-26 | Abbott Laboratories | Aryl phenycyclopropyl sulfide derivatives and their use as cell adhesion-inhibiting anti-inflammatory and immune-suppressive agents |
| TW200304820A (en) * | 2002-03-25 | 2003-10-16 | Avanir Pharmaceuticals | Use of benzimidazole analogs in the treatment of cell proliferation |
| US7622592B2 (en) * | 2002-11-01 | 2009-11-24 | Merck & Co., Inc. | Carbonylamino-benzimidazole derivatives as androgen receptor modulators |
| US7968577B2 (en) * | 2006-11-01 | 2011-06-28 | Bristol-Myers Squibb Company | Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof |
| US8163743B2 (en) * | 2008-06-05 | 2012-04-24 | GlaxoGroupLimited | 4-carboxamide indazole derivatives useful as inhibitors of PI3-kinases |
| EP2462128B1 (en) * | 2009-08-04 | 2016-09-21 | Amira Pharmaceuticals, Inc. | Compounds as lysophosphatidic acid receptor antagonists |
| JP5837821B2 (ja) | 2009-09-24 | 2015-12-24 | 中外製薬株式会社 | 抗体定常領域改変体 |
| GB2474748B (en) * | 2009-10-01 | 2011-10-12 | Amira Pharmaceuticals Inc | Polycyclic compounds as lysophosphatidic acid receptor antagonists |
| GB2474120B (en) * | 2009-10-01 | 2011-12-21 | Amira Pharmaceuticals Inc | Compounds as Lysophosphatidic acid receptor antagonists |
-
2012
- 2012-07-07 US US14/237,446 patent/US8912202B2/en not_active Expired - Fee Related
- 2012-07-07 AU AU2012292649A patent/AU2012292649B8/en not_active Ceased
- 2012-07-07 CN CN201280038210.9A patent/CN103702984B/zh not_active Expired - Fee Related
- 2012-07-07 CA CA2844469A patent/CA2844469C/en not_active Expired - Fee Related
- 2012-07-07 JP JP2014524284A patent/JP5978302B2/ja not_active Expired - Fee Related
- 2012-07-07 WO PCT/EP2012/002874 patent/WO2013020622A1/en not_active Ceased
- 2012-07-07 EP EP12733424.1A patent/EP2742029B1/en not_active Not-in-force
- 2012-07-07 ES ES12733424.1T patent/ES2609003T3/es active Active
-
2014
- 2014-02-06 IL IL230835A patent/IL230835B/en active IP Right Grant
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