JP2012502927A5 - - Google Patents
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- Publication number
- JP2012502927A5 JP2012502927A5 JP2011527166A JP2011527166A JP2012502927A5 JP 2012502927 A5 JP2012502927 A5 JP 2012502927A5 JP 2011527166 A JP2011527166 A JP 2011527166A JP 2011527166 A JP2011527166 A JP 2011527166A JP 2012502927 A5 JP2012502927 A5 JP 2012502927A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- acetic acid
- methyl
- indol
- tetrahydropyrido
- 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.)
- Pending
Links
- -1 NR f R g Inorganic materials 0.000 claims description 31
- 125000000217 alkyl group Chemical group 0.000 claims description 30
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
- 125000001072 heteroaryl group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 138
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 51
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 49
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 23
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 10
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 1
- 125000001216 2-naphthoyl group Chemical group C1=C(C=CC2=CC=CC=C12)C(=O)* 0.000 claims 1
- RNOVGJWJVRESAA-UHFFFAOYSA-N 4-fluoro-2-(trifluoromethyl)phenol Chemical group OC1=CC=C(F)C=C1C(F)(F)F RNOVGJWJVRESAA-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 102000009389 Prostaglandin D receptors Human genes 0.000 claims 1
- 108050000258 Prostaglandin D receptors Proteins 0.000 claims 1
- 125000006638 cyclopentyl carbonyl group Chemical group 0.000 claims 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 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
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19278708P | 2008-09-22 | 2008-09-22 | |
| US61/192,787 | 2008-09-22 | ||
| US17243909P | 2009-04-24 | 2009-04-24 | |
| US61/172,439 | 2009-04-24 | ||
| PCT/CA2009/001321 WO2010031183A1 (en) | 2008-09-22 | 2009-09-17 | Indole derivatives as crth2 receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012502927A JP2012502927A (ja) | 2012-02-02 |
| JP2012502927A5 true JP2012502927A5 (enExample) | 2012-10-25 |
Family
ID=42039054
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011527166A Pending JP2012502927A (ja) | 2008-09-22 | 2009-09-17 | Ｃｒｔｈ２受容体拮抗薬としてのインドール誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8637671B2 (enExample) |
| EP (1) | EP2346865B1 (enExample) |
| JP (1) | JP2012502927A (enExample) |
| AU (1) | AU2009295230A1 (enExample) |
| CA (1) | CA2737483A1 (enExample) |
| WO (1) | WO2010031183A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8637541B2 (en) * | 2008-09-22 | 2014-01-28 | Merck Canada Inc. | Indole derivatives as CRTH2 receptor antagonists |
| EP2401269B1 (en) | 2009-02-24 | 2014-01-29 | Merck Sharp & Dohme Corp. | Indole derivatives as crth2 receptor antagonists |
| DK2558447T3 (da) | 2010-03-22 | 2014-11-10 | Actelion Pharmaceuticals Ltd | 3-(heteroaryl-amino)-1,2,3,4-tetrahydro-9h-carbazolderivater og deres anvendelse som prostaglandin d2-receptormodulatorer |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| EP2661265B1 (en) | 2010-12-23 | 2017-03-08 | Merck Sharp & Dohme Corp. | Quinolines and aza-quinolines as crth2 receptor modulators |
| MX2013007295A (es) | 2010-12-23 | 2013-08-26 | Merck Sharp & Dohme | Quinoxalinas y aza-quinoxalinas como moduladores del receptor de crth2. |
| KR101928595B1 (ko) * | 2011-04-14 | 2018-12-12 | 이도르시아 파마슈티컬스 리미티드 | 7-(헤테로아릴-아미노)-6,7,8,9-테트라히드로피리도［1,2-ａ］인돌 아세트산 유도체 및 프로스타글란딘 ｄ2 수용체 조절자로서의 이의 용도 |
| EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
| EP2720545B1 (en) | 2011-06-17 | 2016-11-30 | Merck Sharp & Dohme Corp. | Cycloalkyl-fused tetrahydroquinolines as crth2 receptor modulators |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| JP6152489B2 (ja) * | 2014-03-17 | 2017-06-21 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | アザインドール酢酸誘導体及びプロスタグランジンｄ２受容体調節剤としてのそれらの使用 |
| MX2016011900A (es) | 2014-03-18 | 2016-12-05 | Actelion Pharmaceuticals Ltd | Derivados de acido azaindol-acetico y su uso como moduladores del receptor de prostaglandina d2. |
| WO2016133793A1 (en) * | 2015-02-16 | 2016-08-25 | Merck Sharp & Dohme Corp. | FACTOR IXa INHIBITORS |
| DK3277722T3 (da) | 2015-04-02 | 2021-10-11 | Intervet Int Bv | Antistoffer mod canin interleukin-4 receptor alpha |
| WO2017005766A1 (en) | 2015-07-07 | 2017-01-12 | Intervet International B.V. | A process to make tricycic alcohol intermediates of crth2 antagonists |
| WO2017005759A1 (en) | 2015-07-07 | 2017-01-12 | Intervet International B.V. | A process to make azaindole derivatives |
| CN108026093B (zh) | 2015-09-15 | 2021-11-16 | 爱杜西亚药品有限公司 | 结晶形式 |
| JP7719077B2 (ja) | 2019-12-20 | 2025-08-05 | インターベット インターナショナル ベー． フェー． | アトピー性皮膚炎を処置するための二重特異性イヌ化抗体および二重特異性結合パートナー |
| JP2024532158A (ja) | 2021-08-20 | 2024-09-05 | インターベット インターナショナル ベー． フェー． | アトピー性皮膚炎を治療するためのホモ二量体融合タンパク質 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MC2096A1 (fr) | 1989-02-23 | 1991-02-15 | Hoffmann La Roche | Pyrroles substitues |
| WO1995015973A1 (en) | 1993-12-06 | 1995-06-15 | Cytel Corporation | Cs-1 peptidomimetics, compositions and methods of using the same |
| US5510332A (en) | 1994-07-07 | 1996-04-23 | Texas Biotechnology Corporation | Process to inhibit binding of the integrin α4 62 1 to VCAM-1 or fibronectin and linear peptides therefor |
| CA2193508A1 (en) | 1994-07-11 | 1996-01-25 | Eugene D. Thorsett | Inhibitors of leukocyte adhesion |
| US5811391A (en) | 1994-08-25 | 1998-09-22 | Cytel Corporation | Cyclic CS-1 peptidomimetics, compositions and methods of using same |
| GB9524630D0 (en) | 1994-12-24 | 1996-01-31 | Zeneca Ltd | Chemical compounds |
| US6306840B1 (en) | 1995-01-23 | 2001-10-23 | Biogen, Inc. | Cell adhesion inhibitors |
| WO1996031206A2 (en) | 1995-04-07 | 1996-10-10 | Warner-Lambert Company | Flavones and coumarins as agents for the treatment of atherosclerosis |
| WO1996040781A1 (en) | 1995-06-07 | 1996-12-19 | Tanabe Seiyaku Co., Ltd. | CYCLIC PEPTIDE INHIBITORS OF β1 AND β2 INTEGRIN-MEDIATED ADHESION |
| EP0842195A1 (en) | 1995-07-06 | 1998-05-20 | Zeneca Limited | Peptide inhibitors of fibronectine |
| US6248713B1 (en) | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
| DE60334015D1 (de) * | 2002-10-30 | 2010-10-14 | Merck Frosst Canada Ltd | Pyridopyrrolizin- und pyridoindolizinderivate |
| WO2006125179A1 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic compounds and their uses as therapeutic agents |
| JP4972644B2 (ja) | 2005-08-12 | 2012-07-11 | メルク カナダ インコーポレイテッド | Ｃｒｔｈ２受容体拮抗薬としてのインドール誘導体 |
| TW200902016A (en) * | 2007-05-22 | 2009-01-16 | Taigen Biotechnology Co Ltd | Kinesin inhibitors |
| JP2011500584A (ja) | 2007-10-10 | 2011-01-06 | ケミエテック，エルエルシ− | Ｃｒｔｈ２受容体拮抗薬としての複素環化合物 |
| US8637541B2 (en) * | 2008-09-22 | 2014-01-28 | Merck Canada Inc. | Indole derivatives as CRTH2 receptor antagonists |
| US8546422B2 (en) * | 2008-09-22 | 2013-10-01 | Merck Canada Inc. | Azaindole derivatives as CRTH2 receptor antagonists |
| EP2401269B1 (en) * | 2009-02-24 | 2014-01-29 | Merck Sharp & Dohme Corp. | Indole derivatives as crth2 receptor antagonists |
-
2009
- 2009-09-17 WO PCT/CA2009/001321 patent/WO2010031183A1/en not_active Ceased
- 2009-09-17 US US13/120,074 patent/US8637671B2/en active Active
- 2009-09-17 JP JP2011527166A patent/JP2012502927A/ja active Pending
- 2009-09-17 EP EP09813945.4A patent/EP2346865B1/en active Active
- 2009-09-17 CA CA2737483A patent/CA2737483A1/en not_active Abandoned
- 2009-09-17 AU AU2009295230A patent/AU2009295230A1/en not_active Abandoned
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