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 | 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2011522849A JP2011522849A (ja) | 2011-08-04 |
| JP2011522849A5 true JP2011522849A5 (enExample) | 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 (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 |
|---|---|---|---|---|
| WO2011003604A1 (en) * | 2009-07-10 | 2011-01-13 | Bayer Schering Pharma Aktiengesellschaft | Indazolyl-substituted dihydroisoxa-zolopyridines and methods of use thereof |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| US10750742B2 (en) | 2015-12-22 | 2020-08-25 | 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 |
| 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 |
| TWI899933B (zh) | 2023-04-06 | 2025-10-01 | 美商輝瑞大藥廠 | 經取代吲唑丙酸衍生化合物及其用途 |
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 |
| KR20050004214A (ko) * | 2002-05-31 | 2005-01-12 | 에자이 가부시키가이샤 | 피라졸 화합물 및 이것을 포함하여 이루어지는 의약 조성물 |
| CA2501534A1 (en) | 2002-10-07 | 2004-04-22 | Artesian Therapeutics, Inc. | Dihydropyridine compounds having simultaneous ability to block l-type calcium channels and to inhibit phosphodiesterase type 3 activity |
| 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 |
| WO2006021886A1 (en) * | 2004-08-26 | 2006-03-02 | Pfizer Inc. | Aminoheteroaryl compounds as protein tyrosine kinase inhibitors |
| 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 |
| MX2008011220A (es) * | 2006-03-07 | 2008-09-11 | Array Biopharma Inc | Compuestos de pirazol heterobiciclicos y metodos de uso. |
| CN101472915A (zh) | 2006-04-19 | 2009-07-01 | 诺瓦提斯公司 | 吲唑化合物和抑制cdc7的方法 |
| MY148851A (en) | 2006-12-14 | 2013-06-14 | Bayer Ip Gmbh | Dihydropyridine derivatives as useful as protein kinase inhibitors |
-
2009
- 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 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