JP2011522849A5 - - Google Patents
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- Publication number
- JP2011522849A5 JP2011522849A5 JP2011512860A JP2011512860A JP2011522849A5 JP 2011522849 A5 JP2011522849 A5 JP 2011522849A5 JP 2011512860 A JP2011512860 A JP 2011512860A JP 2011512860 A JP2011512860 A JP 2011512860A JP 2011522849 A5 JP2011522849 A5 JP 2011522849A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- alkylamino
- cycloalkyl
- amino
- 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.)
- Granted
Links
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 34
- 125000001153 fluoro group Chemical group F* 0.000 claims 34
- -1 bromo, difluoromethyl Chemical group 0.000 claims 30
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 26
- 125000001424 substituent group Chemical group 0.000 claims 26
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 25
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 23
- 229910052739 hydrogen Inorganic materials 0.000 claims 22
- 239000001257 hydrogen Substances 0.000 claims 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 21
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 17
- 125000004043 oxo group Chemical group O=* 0.000 claims 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 12
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 12
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 10
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- 150000002431 hydrogen Chemical class 0.000 claims 5
- 230000002062 proliferating effect Effects 0.000 claims 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 5
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 125000005842 heteroatom Chemical group 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 239000012024 dehydrating agents Substances 0.000 claims 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
- YDTDKKULPWTHRV-UHFFFAOYSA-N 1H-indazol-3-amine Chemical compound C1=CC=C2C(N)=NNC2=C1 YDTDKKULPWTHRV-UHFFFAOYSA-N 0.000 claims 1
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical group C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- 206010027476 Metastases Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 238000007126 N-alkylation reaction Methods 0.000 claims 1
- 208000000821 Parathyroid Neoplasms Diseases 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000002246 antineoplastic agent Substances 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 210000001508 eye Anatomy 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 210000003128 head Anatomy 0.000 claims 1
- 210000004185 liver Anatomy 0.000 claims 1
- 208000026045 malignant tumor of parathyroid gland Diseases 0.000 claims 1
- 230000009401 metastasis Effects 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 210000005000 reproductive tract Anatomy 0.000 claims 1
- 230000000241 respiratory effect Effects 0.000 claims 1
- 210000003491 skin Anatomy 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 238000010561 standard procedure Methods 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 238000001356 surgical procedure Methods 0.000 claims 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 210000001685 thyroid gland Anatomy 0.000 claims 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08010422.7 | 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011522849A JP2011522849A (ja) | 2011-08-04 |
| JP2011522849A5 true JP2011522849A5 (https=) | 2012-08-02 |
| JP5506788B2 JP5506788B2 (ja) | 2014-05-28 |
Family
ID=40846407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011512860A Expired - Fee Related JP5506788B2 (ja) | 2008-06-09 | 2009-05-29 | 置換４−（インダゾリル）−１，４−ジヒドロピリジン類およびそれらの使用方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US8551989B2 (https=) |
| EP (1) | EP2294062B1 (https=) |
| JP (1) | JP5506788B2 (https=) |
| CA (1) | CA2727204C (https=) |
| ES (1) | ES2432068T3 (https=) |
| WO (1) | WO2009149837A1 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| JP6943857B2 (ja) | 2015-12-22 | 2021-10-06 | シンジェンタ パーティシペーションズ アーゲー | 有害生物防除活性ピラゾール誘導体 |
| 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 |
| CA3095233A1 (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 |
| CA2482838A1 (en) | 2002-05-31 | 2003-12-11 | Eisai Co., Ltd. | Pyrazole compounds and pharmaceutical compositions containing the compound |
| BR0315103A (pt) | 2002-10-07 | 2005-08-16 | Artesian Therapeutics Inc | Compostos de diidropiridina tendo capacidade simultânea de bloquear os canais de cálcio do tipo l e inibir a atividade da fosfodiesterase do tipo 3 |
| 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 |
| BRPI0514687A (pt) * | 2004-08-26 | 2008-06-17 | Pfizer | compostos amino heteroarila como inibidores de proteìna tirosina cinase |
| US20090298872A1 (en) | 2004-12-13 | 2009-12-03 | 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 |
| BRPI0708615A2 (pt) * | 2006-03-07 | 2011-06-07 | Array Biopharma Inc | compostos de pirazol heterobicìclicos e métodos de uso |
| 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 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 WO PCT/EP2009/003838 patent/WO2009149837A1/en not_active Ceased
- 2009-05-29 CA CA2727204A patent/CA2727204C/en not_active Expired - Fee Related
- 2009-05-29 JP JP2011512860A patent/JP5506788B2/ja not_active Expired - Fee Related
- 2009-05-29 EP EP09761400.2A patent/EP2294062B1/en not_active Not-in-force
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