ES2432068T3 - 4-(Indazolil)-1,4-dihidropiridinas sustituidas y procedimientos de uso de las mismas - Google Patents
4-(Indazolil)-1,4-dihidropiridinas sustituidas y procedimientos de uso de las mismas Download PDFInfo
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- ES2432068T3 ES2432068T3 ES09761400T ES09761400T ES2432068T3 ES 2432068 T3 ES2432068 T3 ES 2432068T3 ES 09761400 T ES09761400 T ES 09761400T ES 09761400 T ES09761400 T ES 09761400T ES 2432068 T3 ES2432068 T3 ES 2432068T3
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- alkyl
- alkylamino
- cycloalkyl
- amino
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- 238000000034 method Methods 0.000 title claims description 169
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 title claims description 14
- 125000004925 dihydropyridyl group Chemical class N1(CC=CC=C1)* 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 226
- -1 bromo, difluoromethyl Chemical group 0.000 claims abstract description 161
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 71
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 68
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 60
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 59
- 125000001424 substituent group Chemical group 0.000 claims abstract description 54
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 45
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 38
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 36
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 31
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 27
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims abstract description 18
- 125000006568 (C4-C7) heterocycloalkyl group Chemical group 0.000 claims abstract description 16
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 16
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 10
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 50
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 47
- 239000001257 hydrogen Substances 0.000 claims description 46
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 42
- 206010028980 Neoplasm Diseases 0.000 claims description 36
- 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
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- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 16
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- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 11
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
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- 125000000217 alkyl group Chemical group 0.000 claims description 9
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- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 8
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 8
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- 229940124597 therapeutic agent Drugs 0.000 claims description 8
- 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 7
- 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
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- 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 7
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
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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 | 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 |
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| ES2432068T3 true ES2432068T3 (es) | 2013-11-29 |
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| 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)
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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 |
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- 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
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|---|---|
| CA2727204C (en) | 2016-02-02 |
| CA2727204A1 (en) | 2009-12-17 |
| EP2294062B1 (en) | 2013-08-21 |
| US8551989B2 (en) | 2013-10-08 |
| 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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