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 (enExample) |
| EP (1) | EP2294062B1 (enExample) |
| JP (1) | JP5506788B2 (enExample) |
| CA (1) | CA2727204C (enExample) |
| ES (1) | ES2432068T3 (enExample) |
| WO (1) | WO2009149837A1 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2767476A1 (en) * | 2009-07-10 | 2011-01-13 | Bayer Pharma Aktiengesellschaft | Indazolyl-substituted dihydroisoxazolopyridines and methods of use thereof |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| MX2018007527A (es) | 2015-12-22 | 2018-09-07 | Syngenta Participations Ag | Derivados de pirazol activos como pesticidas. |
| 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 |
| US20210047297A1 (en) * | 2018-03-28 | 2021-02-18 | 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 |
| KR20050070036A (ko) | 2002-10-07 | 2005-07-05 | 아티젼 쎄라퓨틱스, 인크. | Ｌ형 칼슘 채널을 차단하는 동시에 3형포스포디에스테라제의 활성을 억제할 수 있는디히드로피리딘 화합물 |
| 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 |
| WO2005084672A1 (de) | 2004-03-03 | 2005-09-15 | Boehringer Ingelheim International Gmbh | Ausgewählte cgrp-antagonisten, verfahren zu deren herstellung sowie deren verwendung als arzneimittel |
| MX2007001986A (es) * | 2004-08-26 | 2007-05-10 | Pfizer | Compuestos de aminoheteroarilo como inhibidores de proteina quinasa. |
| EP1828135A4 (en) | 2004-12-13 | 2009-08-12 | 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 |
| RU2008139599A (ru) * | 2006-03-07 | 2010-04-20 | Эррэй Биофарма Инк. (Us) | Гетеробициклические производные пиразола и способы их применения |
| RU2008145225A (ru) * | 2006-04-19 | 2010-05-27 | Новартис АГ (CH) | Соединения индазола и способы ингибирования cd7 |
| ES2396160T3 (es) * | 2006-12-14 | 2013-02-19 | Bayer Intellectual Property Gmbh | Derivados de DIHIDROPIRIDINA que utiliza como inhibidores de la proteina quinasa |
-
2009
- 2009-05-29 CA CA2727204A patent/CA2727204C/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 US US12/996,465 patent/US8551989B2/en not_active Expired - Fee Related
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| EP2294062B1 (en) | 2013-08-21 |
| US20110207731A1 (en) | 2011-08-25 |
| US8551989B2 (en) | 2013-10-08 |
| CA2727204A1 (en) | 2009-12-17 |
| JP5506788B2 (ja) | 2014-05-28 |
| JP2011522849A (ja) | 2011-08-04 |
| EP2294062A1 (en) | 2011-03-16 |
| ES2432068T3 (es) | 2013-11-29 |
| WO2009149837A1 (en) | 2009-12-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20140401 |
|
| MKLA | Lapsed |
Effective date: 20190529 |