CA2658379C - Spirocyclic azaindole derivatives - Google Patents
Spirocyclic azaindole derivatives Download PDFInfo
- Publication number
- CA2658379C CA2658379C CA2658379A CA2658379A CA2658379C CA 2658379 C CA2658379 C CA 2658379C CA 2658379 A CA2658379 A CA 2658379A CA 2658379 A CA2658379 A CA 2658379A CA 2658379 C CA2658379 C CA 2658379C
- Authority
- CA
- Canada
- Prior art keywords
- azaindole
- spiro
- cyclohexane
- alkyl
- polysubstituted
- 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.)
- Expired - Fee Related
Links
- 125000005334 azaindolyl group Chemical class N1N=C(C2=CC=CC=C12)* 0.000 title claims abstract description 60
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 14
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- 239000000203 mixture Substances 0.000 claims description 168
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 99
- 229920006395 saturated elastomer Polymers 0.000 claims description 74
- -1 benzodioxanyl Chemical group 0.000 claims description 57
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000001072 heteroaryl group Chemical group 0.000 claims description 44
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 31
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- 150000003839 salts Chemical class 0.000 claims description 29
- 239000003814 drug Substances 0.000 claims description 27
- 238000011282 treatment Methods 0.000 claims description 26
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 22
- 230000036407 pain Effects 0.000 claims description 19
- 229910052740 iodine Inorganic materials 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001544 thienyl group Chemical group 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
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- 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 11
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
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- HZXJVDYQRYYYOR-UHFFFAOYSA-K scandium(iii) trifluoromethanesulfonate Chemical compound [Sc+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F HZXJVDYQRYYYOR-UHFFFAOYSA-K 0.000 description 1
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- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
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- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
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- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
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- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/12—Antidiuretics, e.g. drugs for diabetes insipidus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Diabetes (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Rheumatology (AREA)
- Hospice & Palliative Care (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Dermatology (AREA)
- Anesthesiology (AREA)
- Child & Adolescent Psychology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006033114A DE102006033114A1 (de) | 2006-07-18 | 2006-07-18 | Spirocyclische Azaindol-Derivate |
| DE102006033114.1 | 2006-07-18 | ||
| PCT/EP2007/006326 WO2008009416A1 (de) | 2006-07-18 | 2007-07-17 | Spirocyclische azaindol-derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2658379A1 CA2658379A1 (en) | 2008-01-24 |
| CA2658379C true CA2658379C (en) | 2014-05-06 |
Family
ID=38704887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2658379A Expired - Fee Related CA2658379C (en) | 2006-07-18 | 2007-07-17 | Spirocyclic azaindole derivatives |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8399503B2 (https=) |
| EP (1) | EP2041142B1 (https=) |
| JP (1) | JP5269784B2 (https=) |
| KR (1) | KR101421034B1 (https=) |
| CN (1) | CN101490055B (https=) |
| AR (1) | AR062079A1 (https=) |
| AU (1) | AU2007276414B2 (https=) |
| BR (1) | BRPI0714650A2 (https=) |
| CA (1) | CA2658379C (https=) |
| CL (1) | CL2007001917A1 (https=) |
| DE (1) | DE102006033114A1 (https=) |
| ES (1) | ES2434114T3 (https=) |
| IL (1) | IL196525A (https=) |
| MX (1) | MX2009000670A (https=) |
| NO (1) | NO342282B1 (https=) |
| NZ (1) | NZ573688A (https=) |
| PE (1) | PE20080277A1 (https=) |
| PL (1) | PL2041142T3 (https=) |
| RU (1) | RU2468028C2 (https=) |
| WO (1) | WO2008009416A1 (https=) |
| ZA (1) | ZA200901128B (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006033114A1 (de) | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| AU2009228637B2 (en) * | 2008-03-27 | 2013-12-19 | Grunenthal Gmbh | (Hetero-)aryl cyclohexane derivatives |
| CA2719735A1 (en) | 2008-03-27 | 2009-10-01 | Gruenenthal Gmbh | Substituted 4-aminocyclohexane derivatives |
| PT2260042E (pt) * | 2008-03-27 | 2011-12-06 | Gruenenthal Gmbh | Derivados de ciclo-hexano espirocíclicos substituídos |
| WO2009118174A1 (de) | 2008-03-27 | 2009-10-01 | Grünenthal GmbH | Substituierte cyclohexyldiamine |
| ATE537143T1 (de) * | 2008-03-27 | 2011-12-15 | Gruenenthal Gmbh | Spiro(5.5)undecan derivate |
| JP5599774B2 (ja) | 2008-03-27 | 2014-10-01 | グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング | ヒドロキシメチルシクロヘキシルアミン類 |
| WO2011153359A1 (en) | 2010-06-04 | 2011-12-08 | Albany Molecular Research, Inc. | Glycine transporter-1 inhibitors, methods of making them, and uses thereof |
| TWI582092B (zh) | 2010-07-28 | 2017-05-11 | 歌林達股份有限公司 | 順式－四氫－螺旋（環己烷－１,１’－吡啶［３,４－b］吲哚）－４－胺－衍生物 |
| EP2649044B1 (en) | 2010-12-08 | 2017-09-20 | Grünenthal GmbH | Method for synthesising substituted aminocyclohexanone derivatives |
| JP6557674B2 (ja) * | 2014-03-12 | 2019-08-07 | ザ・トラスティーズ・オブ・コランビア・ユニバーシティー・イン・ザ・シティー・オブ・ニューヨーク | 新規クラスのミュー−オピオイド受容体アゴニスト |
| HUE040133T2 (hu) | 2014-07-15 | 2019-02-28 | Gruenenthal Gmbh | Szubsztituált azaspiro(4.5)dekán származékok |
| TW201607923A (zh) | 2014-07-15 | 2016-03-01 | 歌林達有限公司 | 被取代之氮螺環（４．５）癸烷衍生物 |
| CA2998868A1 (en) | 2015-09-16 | 2017-03-23 | The Trustees Of Columbia University In The City Of New York | Carboxylic diarylthiazepineamines as mu-opioid receptor agonists |
| CN117447384B (zh) * | 2023-10-24 | 2024-12-27 | 四川大学 | 一种螺杂环芳基类化合物及其应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4065573A (en) | 1976-06-03 | 1977-12-27 | The Upjohn Company | 4-Amino-4-phenylcyclohexanone ketal compositions and process of use |
| EP0738717A1 (en) * | 1990-10-09 | 1996-10-23 | Neurogen Corporation | Certain substituted pyrimidines as intermediates for production of cycloalkyl and azacycloalkyl pyrrolopyrimidines |
| WO2000038720A1 (en) * | 1998-12-24 | 2000-07-06 | Meiji Seika Kaisha, Ltd. | Remedies for pain |
| GB9918965D0 (en) * | 1999-08-11 | 1999-10-13 | Cerebrus Ltd | Chemical compounds xxi |
| HUP0300413A2 (hu) * | 2000-04-10 | 2003-06-28 | Pfizer Products Inc. | Amidcsoportot viselő benzolgyűrűs csoporttal helyettesített piperidint tartalmazó és rokonszerkezetű vegyületek, eljárás az előállításukra és ezeket tartalmazó gyógyszerkészítmények |
| DE10123163A1 (de) | 2001-05-09 | 2003-01-16 | Gruenenthal Gmbh | Substituierte Cyclohexan-1,4-diaminderivate |
| RU2216737C1 (ru) * | 2002-03-19 | 2003-11-20 | Санкт-Петербургский государственный медицинский университет им. акад. И.П. Павлова | Способ оценки течения хронического воспалительного процесса в бронхолегочной системе больного муковисцидозом |
| DE10252667A1 (de) * | 2002-11-11 | 2004-05-27 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| US7872133B2 (en) * | 2003-06-23 | 2011-01-18 | Ono Pharmaceutical Co., Ltd. | Tricyclic heterocycle compound |
| DE10360793A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE10360792A1 (de) * | 2003-12-23 | 2005-07-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102004039382A1 (de) * | 2004-08-13 | 2006-02-23 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| US7659264B2 (en) * | 2004-10-07 | 2010-02-09 | Merck Sharp & Dohme Corp. | CGRP receptor antagonists |
| EP1829874B1 (en) * | 2004-12-22 | 2014-02-12 | Ono Pharmaceutical Co., Ltd. | Tricyclic compound and use thereof |
| DE102005016460A1 (de) * | 2005-04-11 | 2006-10-19 | Grünenthal GmbH | Spriocyclische Cyclohexanderivate zur Behandlung von Substanzabhängigkeit |
| DE102006019597A1 (de) * | 2006-04-27 | 2007-10-31 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102006033114A1 (de) | 2006-07-18 | 2008-01-24 | Grünenthal GmbH | Spirocyclische Azaindol-Derivate |
| DE102007009235A1 (de) * | 2007-02-22 | 2008-09-18 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| DE102007009319A1 (de) * | 2007-02-22 | 2008-08-28 | Grünenthal GmbH | Spirocyclische Cyclohexan-Derivate |
| PT2260042E (pt) * | 2008-03-27 | 2011-12-06 | Gruenenthal Gmbh | Derivados de ciclo-hexano espirocíclicos substituídos |
-
2006
- 2006-07-18 DE DE102006033114A patent/DE102006033114A1/de not_active Withdrawn
-
2007
- 2007-06-29 CL CL200701917A patent/CL2007001917A1/es unknown
- 2007-07-16 AR ARP070103151A patent/AR062079A1/es not_active Application Discontinuation
- 2007-07-16 PE PE2007000917A patent/PE20080277A1/es active IP Right Grant
- 2007-07-17 EP EP07786123.5A patent/EP2041142B1/de active Active
- 2007-07-17 MX MX2009000670A patent/MX2009000670A/es active IP Right Grant
- 2007-07-17 WO PCT/EP2007/006326 patent/WO2008009416A1/de not_active Ceased
- 2007-07-17 BR BRPI0714650-7A patent/BRPI0714650A2/pt not_active Application Discontinuation
- 2007-07-17 CA CA2658379A patent/CA2658379C/en not_active Expired - Fee Related
- 2007-07-17 NZ NZ573688A patent/NZ573688A/en not_active IP Right Cessation
- 2007-07-17 JP JP2009519861A patent/JP5269784B2/ja not_active Expired - Fee Related
- 2007-07-17 CN CN2007800272998A patent/CN101490055B/zh not_active Expired - Fee Related
- 2007-07-17 ES ES07786123T patent/ES2434114T3/es active Active
- 2007-07-17 AU AU2007276414A patent/AU2007276414B2/en not_active Ceased
- 2007-07-17 KR KR1020097003277A patent/KR101421034B1/ko not_active Expired - Fee Related
- 2007-07-17 PL PL07786123T patent/PL2041142T3/pl unknown
- 2007-07-17 RU RU2009105399/04A patent/RU2468028C2/ru not_active IP Right Cessation
-
2009
- 2009-01-15 US US12/354,001 patent/US8399503B2/en not_active Expired - Fee Related
- 2009-01-15 IL IL196525A patent/IL196525A/en active IP Right Grant
- 2009-01-19 NO NO20090294A patent/NO342282B1/no not_active IP Right Cessation
- 2009-02-17 ZA ZA2009/01128A patent/ZA200901128B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| KR101421034B1 (ko) | 2014-07-22 |
| PE20080277A1 (es) | 2008-04-11 |
| CL2007001917A1 (es) | 2008-03-14 |
| HK1129676A1 (en) | 2009-12-04 |
| AU2007276414A1 (en) | 2008-01-24 |
| JP5269784B2 (ja) | 2013-08-21 |
| CA2658379A1 (en) | 2008-01-24 |
| ES2434114T3 (es) | 2013-12-13 |
| US8399503B2 (en) | 2013-03-19 |
| NO20090294L (no) | 2009-03-31 |
| EP2041142B1 (de) | 2013-10-09 |
| IL196525A (en) | 2015-07-30 |
| WO2008009416A1 (de) | 2008-01-24 |
| ZA200901128B (en) | 2009-12-30 |
| IL196525A0 (en) | 2009-11-18 |
| RU2468028C2 (ru) | 2012-11-27 |
| RU2009105399A (ru) | 2010-08-27 |
| CN101490055B (zh) | 2013-10-16 |
| PL2041142T3 (pl) | 2014-01-31 |
| NO342282B1 (no) | 2018-04-30 |
| EP2041142A1 (de) | 2009-04-01 |
| AR062079A1 (es) | 2008-10-15 |
| AU2007276414B2 (en) | 2012-05-31 |
| MX2009000670A (es) | 2009-01-30 |
| CN101490055A (zh) | 2009-07-22 |
| KR20090035708A (ko) | 2009-04-10 |
| BRPI0714650A2 (pt) | 2013-04-02 |
| JP2009543825A (ja) | 2009-12-10 |
| DE102006033114A1 (de) | 2008-01-24 |
| NZ573688A (en) | 2011-12-22 |
| US20090156593A1 (en) | 2009-06-18 |
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Legal Events
| Date | Code | Title | Description |
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| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20200831 |