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 |
|---|---|---|---|---|
| AU2009295229B2 (en) * | 2008-09-22 | 2014-02-27 | Merck Canada Inc. | Indole derivatives as CRTH2 receptor antagonists |
| MA33134B1 (fr) * | 2009-02-24 | 2012-03-01 | Merck Canada Inc | Derives d'indole en tant qu'antagonistes du recepteur crth2 |
| MX2012010820A (es) | 2010-03-22 | 2012-10-10 | Actelion Pharmaceuticals Ltd | Derivados de 3-(heteroaril-amino)-1, 2, 3, 4-tetrahidro-9h-carbazo l y sus uso como moduladores del receptor de prostaglandina d2. |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| US9290453B2 (en) | 2010-12-23 | 2016-03-22 | Merck Sharp & Dohme Corp. | Quinolines and aza-quinolines as CRTH2 receptor modulators |
| BR112013015397A2 (pt) | 2010-12-23 | 2016-09-20 | Merck Sharp & Dohme | composto, composição farmacêutica, e, uso de um composto |
| WO2012140612A1 (en) | 2011-04-14 | 2012-10-18 | Actelion Pharmaceuticals Ltd | 7-(heteroaryl-amino)-6,7,8,9-tetrahydropyrido[1,2-a]indol acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
| EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
| PH12013502619A1 (en) | 2011-06-17 | 2014-02-17 | Merck Sharp & Dohme | Cycloalkyl-fused tetrahydroquinolines as crth2 receptor modulators |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| PH12016501764B1 (en) * | 2014-03-17 | 2024-05-17 | Idorsia Pharmaceuticals Ltd | Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
| WO2015140701A1 (en) | 2014-03-18 | 2015-09-24 | Actelion Pharmaceuticals Ltd | Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
| WO2016133793A1 (en) * | 2015-02-16 | 2016-08-25 | Merck Sharp & Dohme Corp. | FACTOR IXa INHIBITORS |
| EP3954710A3 (en) | 2015-04-02 | 2022-07-20 | Intervet International B.V. | Antibodies to canine 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 |
| WO2017046125A1 (en) | 2015-09-15 | 2017-03-23 | Actelion Pharmaceuticals Ltd | Crystalline forms |
| WO2021123092A1 (en) | 2019-12-20 | 2021-06-24 | Intervet International B.V. | Bispecific caninized antibodies for treating atopic dermatitis |
| US20240368249A1 (en) | 2021-08-20 | 2024-11-07 | Intervet Inc. | Fusion proteins for treating atopic dermatitis |
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 |
| AU693143B2 (en) | 1993-12-06 | 1998-06-25 | 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 |
| EP0769958B1 (en) | 1994-07-11 | 2003-04-16 | Athena Neurosciences, Inc. | 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 |
| AU5259296A (en) | 1995-04-07 | 1996-10-23 | Warner-Lambert Company | Flavones and coumarins as agents for the treatment of athero sclerosis |
| WO1996040781A1 (en) | 1995-06-07 | 1996-12-19 | Tanabe Seiyaku Co., Ltd. | CYCLIC PEPTIDE INHIBITORS OF β1 AND β2 INTEGRIN-MEDIATED ADHESION |
| JPH11508583A (ja) | 1995-07-06 | 1999-07-27 | ゼネカ・リミテッド | ペプチド系のフィブロネクチン阻害薬 |
| US6248713B1 (en) | 1995-07-11 | 2001-06-19 | Biogen, Inc. | Cell adhesion inhibitors |
| EP1558614B1 (en) * | 2002-10-30 | 2010-09-01 | Merck Frosst Canada Ltd. | Pyridopyrrolizine and pyridoindolizine derivatives |
| WO2006125179A1 (en) | 2005-05-19 | 2006-11-23 | Xenon Pharmaceuticals Inc. | Tricyclic compounds and their uses as therapeutic agents |
| US7696222B2 (en) * | 2005-08-12 | 2010-04-13 | Merck Frosst Canada Ltd | Indole derivatives as CRTH2 receptor antagonists |
| WO2008147852A1 (en) * | 2007-05-22 | 2008-12-04 | Taigen Biotechnology Co., Ltd. | Kinesin inhibitors |
| US8772312B2 (en) | 2007-10-10 | 2014-07-08 | Cspc Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd. | Heterocyclic compounds as CRTH2 receptor antagonists |
| WO2010031184A1 (en) | 2008-09-22 | 2010-03-25 | Merck Frosst Canada Ltd. | Azaindole derivatives as crth2 receptor antagonists |
| AU2009295229B2 (en) | 2008-09-22 | 2014-02-27 | Merck Canada Inc. | Indole derivatives as CRTH2 receptor antagonists |
| MA33134B1 (fr) * | 2009-02-24 | 2012-03-01 | Merck Canada Inc | Derives d'indole en tant qu'antagonistes du recepteur crth2 |
-
2009
- 2009-09-17 WO PCT/CA2009/001321 patent/WO2010031183A1/en not_active Ceased
- 2009-09-17 AU AU2009295230A patent/AU2009295230A1/en not_active Abandoned
- 2009-09-17 JP JP2011527166A patent/JP2012502927A/ja active Pending
- 2009-09-17 CA CA2737483A patent/CA2737483A1/en not_active Abandoned
- 2009-09-17 EP EP09813945.4A patent/EP2346865B1/en active Active
- 2009-09-17 US US13/120,074 patent/US8637671B2/en not_active Expired - Fee Related
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