CA2727204C - Substituted 4-(indazolyl)-1,4-dihydropyridines and methods of use thereof - Google Patents
Substituted 4-(indazolyl)-1,4-dihydropyridines and methods of use thereof Download PDFInfo
- Publication number
- CA2727204C CA2727204C CA2727204A CA2727204A CA2727204C CA 2727204 C CA2727204 C CA 2727204C CA 2727204 A CA2727204 A CA 2727204A CA 2727204 A CA2727204 A CA 2727204A CA 2727204 C CA2727204 C CA 2727204C
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- group
- alkyl
- alkylamino
- amino
- cycloalkyl
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- 238000000034 method Methods 0.000 title claims abstract description 153
- YKZJPQSQSIKVBV-UHFFFAOYSA-N 3-(1,4-dihydropyridin-4-yl)-2h-indazole Chemical class C1=CNC=CC1C1=C2C=CC=CC2=NN1 YKZJPQSQSIKVBV-UHFFFAOYSA-N 0.000 title abstract 2
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- -1 bromo, difluoromethyl Chemical group 0.000 claims description 147
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 76
- 125000001153 fluoro group Chemical group F* 0.000 claims description 68
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 55
- 125000001424 substituent group Chemical group 0.000 claims description 54
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- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
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- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 40
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 24
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 21
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- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 10
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 9
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 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 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000003821 2-(trimethylsilyl)ethoxymethyl group Chemical group [H]C([H])([H])[Si](C([H])([H])[H])(C([H])([H])[H])C([H])([H])C(OC([H])([H])[*])([H])[H] 0.000 claims description 6
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- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08010422 | 2008-06-09 | ||
| EP08010422.7 | 2008-06-09 | ||
| PCT/EP2009/003838 WO2009149837A1 (en) | 2008-06-09 | 2009-05-29 | Substituted 4- (indazolyl) -1,4-dihydropyridines and methods of use thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2727204A1 CA2727204A1 (en) | 2009-12-17 |
| CA2727204C true CA2727204C (en) | 2016-02-02 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2727204A Expired - Fee Related CA2727204C (en) | 2008-06-09 | 2009-05-29 | Substituted 4-(indazolyl)-1,4-dihydropyridines and methods of use thereof |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8551989B2 (OSRAM) |
| EP (1) | EP2294062B1 (OSRAM) |
| JP (1) | JP5506788B2 (OSRAM) |
| CA (1) | CA2727204C (OSRAM) |
| ES (1) | ES2432068T3 (OSRAM) |
| WO (1) | WO2009149837A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP5674211B2 (ja) * | 2009-07-10 | 2015-02-25 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | インダゾリル置換のジヒドロイソオキサゾロピリジンおよびその使用方法 |
| US9056867B2 (en) | 2011-09-16 | 2015-06-16 | Novartis Ag | N-substituted heterocyclyl carboxamides |
| EP3393245A1 (en) | 2015-12-22 | 2018-10-31 | Syngenta Participations AG | Pesticidally active pyrazole derivatives |
| WO2018165501A1 (en) * | 2017-03-10 | 2018-09-13 | Lycera Corporation | INDOLINYL SULFONAMIDE AND RELATED COMPOUNDS FOR USE AS AGONISTS OF RORγ AND THE TREATMENT OF DISEASE |
| WO2019185525A1 (en) * | 2018-03-28 | 2019-10-03 | Bayer Pharma Aktiengesellschaft | 4-(3-amino-6-fluoro-1h-indazol-5-yl)-1,2,6-trimethyl-1,4-dihydropyridine-3,5-dic arbonitrile compounds for treating hyperproliferative disorders |
| AU2024249981A1 (en) | 2023-04-06 | 2025-10-16 | Pfizer Inc. | Substituted indazole propionic acid derivative compounds and uses thereof as ampk activators |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4011106A1 (de) | 1990-04-06 | 1991-10-10 | Bayer Ag | Neue heterocyclisch substituierte dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DE4202526A1 (de) | 1992-01-30 | 1993-08-05 | Bayer Ag | Neue 4-cinnolinyl- und 4-naphthyridinyl-dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| DE4313697A1 (de) | 1993-04-27 | 1994-11-03 | Bayer Ag | Chinolyl-dihydropyridinester, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimitteln |
| DE4321030A1 (de) | 1993-06-24 | 1995-01-05 | Bayer Ag | 4-bicyclisch substituierte Dihydropyridine, Verfahren zu ihrer Herstellung und ihre Verwendung in Arzneimittel |
| TW200406385A (en) | 2002-05-31 | 2004-05-01 | Eisai Co Ltd | Pyrazole compound and pharmaceutical composition containing the same |
| JP2006504738A (ja) | 2002-10-07 | 2006-02-09 | アルテシアン セラピューティック，インコーポレイティド | Ｌ型カルシウムチャンネルを遮断し、かつホスホジエステラーゼ３型活性を阻害する同時能力を有するジヒドロピリジン化合物 |
| US7008953B2 (en) * | 2003-07-30 | 2006-03-07 | Agouron Pharmaceuticals, Inc. | 3, 5 Disubstituted indazole compounds, pharmaceutical compositions, and methods for mediating or inhibiting cell proliferation |
| WO2005016885A2 (en) | 2003-08-14 | 2005-02-24 | Artesian Therapeutics, Inc. | COMPOUNDS WITH COMBINED CALCIUM CHANNEL BLOCKER AND β-ADRENERGIC ANTAGONIST OR PARTIAL AGONIST ACTIVITIES FOR TREATMENT OF HEART DISEASE |
| US7569578B2 (en) | 2003-12-05 | 2009-08-04 | Bristol-Meyers Squibb Company | Heterocyclic anti-migraine agents |
| EP1722792A1 (de) | 2004-03-03 | 2006-11-22 | Boehringer Ingelheim International GmbH | Ausgewählte cgrp-antagonisten, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
| JP2008510792A (ja) * | 2004-08-26 | 2008-04-10 | ファイザー・インク | タンパク質チロシンキナーゼ阻害剤としてのアミノヘテロアリール化合物 |
| WO2006066011A2 (en) | 2004-12-13 | 2006-06-22 | Irm Llc | Compounds and compositions as modulators of steroidal receptors and calcium channel activities |
| US20070112015A1 (en) | 2005-10-28 | 2007-05-17 | Chemocentryx, Inc. | Substituted dihydropyridines and methods of use |
| DE102006005180A1 (de) * | 2006-02-06 | 2007-08-09 | Merck Patent Gmbh | Indazol-heteroaryl-derivate |
| JP2009529047A (ja) * | 2006-03-07 | 2009-08-13 | アレイ バイオファーマ、インコーポレイテッド | ヘテロ二環系ピラゾール化合物およびその使用 |
| WO2007124288A1 (en) * | 2006-04-19 | 2007-11-01 | Novartis Ag | Indazole compounds and methods for inhibition of cdc7 |
| CN101558040B (zh) | 2006-12-14 | 2013-03-27 | 拜耳先灵医药股份有限公司 | 用作蛋白激酶抑制剂的二氢吡啶衍生物 |
-
2009
- 2009-05-29 JP JP2011512860A patent/JP5506788B2/ja not_active Expired - Fee Related
- 2009-05-29 WO PCT/EP2009/003838 patent/WO2009149837A1/en not_active Ceased
- 2009-05-29 US US12/996,465 patent/US8551989B2/en not_active Expired - Fee Related
- 2009-05-29 ES ES09761400T patent/ES2432068T3/es active Active
- 2009-05-29 EP EP09761400.2A patent/EP2294062B1/en not_active Not-in-force
- 2009-05-29 CA CA2727204A patent/CA2727204C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2727204A1 (en) | 2009-12-17 |
| EP2294062B1 (en) | 2013-08-21 |
| US8551989B2 (en) | 2013-10-08 |
| ES2432068T3 (es) | 2013-11-29 |
| US20110207731A1 (en) | 2011-08-25 |
| JP5506788B2 (ja) | 2014-05-28 |
| WO2009149837A1 (en) | 2009-12-17 |
| JP2011522849A (ja) | 2011-08-04 |
| EP2294062A1 (en) | 2011-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140401 |
|
| MKLA | Lapsed |
Effective date: 20190529 |