CA2524251A1 - Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disorders - Google Patents
Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disorders Download PDFInfo
- Publication number
- CA2524251A1 CA2524251A1 CA002524251A CA2524251A CA2524251A1 CA 2524251 A1 CA2524251 A1 CA 2524251A1 CA 002524251 A CA002524251 A CA 002524251A CA 2524251 A CA2524251 A CA 2524251A CA 2524251 A1 CA2524251 A1 CA 2524251A1
- Authority
- CA
- Canada
- Prior art keywords
- azetidine
- carboxamide
- trifluoromethyl
- butyl
- dichlorobenzhydryloxy
- 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.)
- Abandoned
Links
- 238000011282 treatment Methods 0.000 title claims abstract description 37
- 230000001404 mediated effect Effects 0.000 title claims abstract description 11
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- 102000005962 receptors Human genes 0.000 title description 11
- 108020003175 receptors Proteins 0.000 title description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 258
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 70
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 61
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 26
- 208000008589 Obesity Diseases 0.000 claims abstract description 20
- 125000003118 aryl group Chemical group 0.000 claims abstract description 20
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- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 claims abstract description 16
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 229940002612 prodrug Drugs 0.000 claims abstract description 8
- 239000000651 prodrug Substances 0.000 claims abstract description 8
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 3
- -1 3-(2,4,4'-trichlorobenzhydryloxy)-N-(tert-butyl)azetidine-1-carboxamide 3-(2,4'-dichlorobenzhydryloxy)-N-(tert-butyl)azetidine-1-carboxamide Chemical compound 0.000 claims description 191
- 238000000034 method Methods 0.000 claims description 181
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
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- LSJZXKGOYIYDQD-UHFFFAOYSA-N 3-[[4-(difluoromethoxy)phenyl]-[2-(trifluoromethyl)phenyl]methoxy]-n-prop-2-enylazetidine-1-carboxamide Chemical compound C1=CC(OC(F)F)=CC=C1C(C=1C(=CC=CC=1)C(F)(F)F)OC1CN(C(=O)NCC=C)C1 LSJZXKGOYIYDQD-UHFFFAOYSA-N 0.000 claims description 5
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- 208000011580 syndromic disease Diseases 0.000 description 1
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- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- JLEHSYHLHLHPAL-UHFFFAOYSA-N tert-butylurea Chemical compound CC(C)(C)NC(N)=O JLEHSYHLHLHPAL-UHFFFAOYSA-N 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical group 0.000 description 1
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- ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
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- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/04—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Neurology (AREA)
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- Pain & Pain Management (AREA)
- Addiction (AREA)
- Diabetes (AREA)
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- Obesity (AREA)
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- Rheumatology (AREA)
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- Heart & Thoracic Surgery (AREA)
- Child & Adolescent Psychology (AREA)
- Emergency Medicine (AREA)
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- Hospice & Palliative Care (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Nutrition Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0310056 | 2003-05-01 | ||
| GB0310056.7 | 2003-05-01 | ||
| PCT/GB2004/001831 WO2004096763A1 (en) | 2003-05-01 | 2004-04-29 | Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disorders |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2524251A1 true CA2524251A1 (en) | 2004-11-11 |
Family
ID=33397041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002524251A Abandoned CA2524251A1 (en) | 2003-05-01 | 2004-04-29 | Azetidinecarboxamide derivatives and their use in the treatment of cb1 receptor mediated disorders |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7504522B2 (https=) |
| EP (1) | EP1620395B1 (https=) |
| JP (1) | JP2006525298A (https=) |
| KR (1) | KR20060010770A (https=) |
| CN (1) | CN1802350A (https=) |
| AT (1) | ATE453620T1 (https=) |
| AU (1) | AU2004234125A1 (https=) |
| BR (1) | BRPI0409938A (https=) |
| CA (1) | CA2524251A1 (https=) |
| DE (1) | DE602004024880D1 (https=) |
| EA (1) | EA010583B1 (https=) |
| MX (1) | MXPA05011670A (https=) |
| NO (1) | NO20055654L (https=) |
| NZ (1) | NZ543016A (https=) |
| WO (1) | WO2004096763A1 (https=) |
| ZA (1) | ZA200508831B (https=) |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
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| NZ543322A (en) * | 2003-05-01 | 2009-03-31 | Vernalis Res Ltd | The use of azetidinecarboxamide derivates in therapy |
| AU2004252109B2 (en) | 2003-06-11 | 2010-04-08 | Merck Sharp & Dohme Corp. | Substituted 3-alkyl and 3-alkenyl azetidine derivatives |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| CA2613678A1 (en) | 2005-06-02 | 2006-12-07 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| US7906652B2 (en) | 2005-11-28 | 2011-03-15 | Merck Sharp & Dohme Corp. | Heterocycle-substituted 3-alkyl azetidine derivatives |
| AU2007222069A1 (en) * | 2006-02-21 | 2007-09-13 | Ampla Pharmaceuticals Inc. | CB1 antagonists and inverse agonists |
| JP2010500300A (ja) | 2006-08-08 | 2010-01-07 | サノフィ−アベンティス | アリールアミノアリール−アルキル−置換イミダゾリジン−２，４−ジオン、それらの製造法、それらの化合物を含有する薬剤、およびそれらの使用 |
| EP2025674A1 (de) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Substituierte Tetrahydronaphthaline, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| CA2709863A1 (fr) * | 2007-12-18 | 2009-09-03 | Sanofi-Aventis | Derives d'azetidines, leur preparation et leur application en therapeutique |
| FR2925051B1 (fr) * | 2007-12-18 | 2010-05-21 | Sanofi Aventis | Derives d'azetidines,leur preparation et leur application en therapeutique |
| WO2009157006A1 (en) * | 2008-06-26 | 2009-12-30 | Micro Labs Limited | Process of preparing ebastine |
| WO2010003624A2 (en) | 2008-07-09 | 2010-01-14 | Sanofi-Aventis | Heterocyclic compounds, processes for their preparation, medicaments comprising these compounds, and the use thereof |
| WO2010047982A1 (en) | 2008-10-22 | 2010-04-29 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
| JP5557845B2 (ja) | 2008-10-31 | 2014-07-23 | メルク・シャープ・アンド・ドーム・コーポレーション | 糖尿病用剤として有用な新規環状ベンゾイミダゾール誘導体 |
| WO2010068601A1 (en) | 2008-12-08 | 2010-06-17 | Sanofi-Aventis | A crystalline heteroaromatic fluoroglycoside hydrate, processes for making, methods of use and pharmaceutical compositions thereof |
| MX2012001729A (es) | 2009-08-26 | 2012-06-13 | Sanofi Sa | Nuevos hidratos cristalinos de fluoroglicosido heteroaromatico, productos farmaceuticos que comprenden estos compuestos, y su empleo. |
| US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
| WO2011157827A1 (de) | 2010-06-18 | 2011-12-22 | Sanofi | Azolopyridin-3-on-derivate als inhibitoren von lipasen und phospholipasen |
| BR112013021236B1 (pt) | 2011-02-25 | 2021-05-25 | Merck Sharp & Dohme Corp | composto derivado de benzimidazol, e, composição |
| US8895547B2 (en) | 2011-03-08 | 2014-11-25 | Sanofi | Substituted phenyl-oxathiazine derivatives, method for producing them, drugs containing said compounds and the use thereof |
| EP2683702B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Neue substituierte phenyl-oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| US8828995B2 (en) | 2011-03-08 | 2014-09-09 | Sanofi | Branched oxathiazine derivatives, method for the production thereof, use thereof as medicine and drug containing said derivatives and use thereof |
| US8871758B2 (en) | 2011-03-08 | 2014-10-28 | Sanofi | Tetrasubstituted oxathiazine derivatives, method for producing them, their use as medicine and drug containing said derivatives and the use thereof |
| EP2683701B1 (de) | 2011-03-08 | 2014-12-24 | Sanofi | Mit benzyl- oder heteromethylengruppen substituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| EP2683698B1 (de) | 2011-03-08 | 2017-10-04 | Sanofi | Mit adamantan- oder noradamantan substituierte benzyl-oxathiazinderivate, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683705B1 (de) | 2011-03-08 | 2015-04-22 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| WO2012120052A1 (de) | 2011-03-08 | 2012-09-13 | Sanofi | Mit carbozyklen oder heterozyklen substituierte oxathiazinderivate, verfahren zu deren herstellung, diese verbindungen enthaltende arzneimittel und deren verwendung |
| EP2683699B1 (de) | 2011-03-08 | 2015-06-24 | Sanofi | Di- und trisubstituierte oxathiazinderivate, verfahren zu deren herstellung, ihre verwendung als medikament sowie sie enthaltendes arzneimittel und deren verwendung |
| US9527875B2 (en) | 2012-08-02 | 2016-12-27 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| RU2015140066A (ru) | 2013-02-22 | 2017-03-30 | Мерк Шарп И Доум Корп. | Противодиабетические бициклические соединения |
| WO2014139388A1 (en) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Novel indole derivatives useful as anti-diabetic agents |
| EP3013958B1 (en) * | 2013-06-25 | 2019-12-25 | The United States of America, as represented by the Secretary, Department of Health and Human Services | Glucan-encapsulated sirna for treating type 2 diabetes mellitus |
| WO2015051496A1 (en) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
| CN105218474B (zh) * | 2015-10-22 | 2017-12-05 | 山东国邦药业股份有限公司 | (4r,5r)‑2‑二氯甲基‑4,5‑二氢‑5‑(4‑甲砜基苯基)‑4‑恶唑甲醇的合成方法 |
| AU2017260706B2 (en) | 2016-05-04 | 2023-05-11 | Inmed Pharmaceuticals Inc. | Use of topical formulations of cannabinoids in the treatment of epidermolysis bullosa and related connective tissue disorders |
| US11072602B2 (en) | 2016-12-06 | 2021-07-27 | Merck Sharp & Dohme Corp. | Antidiabetic heterocyclic compounds |
| EP3684353A4 (en) | 2017-09-22 | 2021-06-23 | Inmed Pharmaceuticals Inc. | TOPICAL FORMULATIONS OF CANNABINOIDS AND THEIR USES FOR PAIN TREATMENT |
| WO2019134985A1 (en) | 2018-01-08 | 2019-07-11 | F. Hoffmann-La Roche Ag | Octahydropyrido[1,2-alpha]pyrazines as magl inhibitors |
| EP3669876A1 (en) * | 2018-12-18 | 2020-06-24 | Aelis Farma | 3béta-(benzyloxy)-17alpha-methyl-pregn-5-en-20-one for use in the treatment of cognitive disorders |
| MX2023002224A (es) | 2020-09-03 | 2023-03-15 | Hoffmann La Roche | Compuestos heterociclicos. |
| US11141404B1 (en) * | 2020-11-18 | 2021-10-12 | Anebulo Pharmaceuticals, Inc. | Formulations and methods for treating acute cannabinoid overdose |
| AU2022362107A1 (en) | 2021-10-11 | 2024-05-02 | Anebulo Pharmaceuticals, Inc. | Crystalline forms of a cannabinoid receptor type 1 (cb1) modulator and methods of use and preparation thereof |
| AU2023351188A1 (en) * | 2022-09-26 | 2025-04-17 | Anebulo Pharmaceuticals, Inc. | Treatment of acute cannabinoid overdose |
| WO2025090133A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Compositions and methods for use of cannabinol compounds in neuroprotection |
| WO2025090587A1 (en) | 2023-10-23 | 2025-05-01 | Inmed Pharmaceuticals Inc. | Cannabinoids compounds and their use in the treatment of neuronal disorders |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4261990A (en) * | 1979-03-09 | 1981-04-14 | Ciba-Geigy Corporation | N-alkyleneiminoalkyl-dicarboximides as antiallergics and antiasthmatics |
| JPH03264562A (ja) * | 1989-05-22 | 1991-11-25 | Hokuriku Seiyaku Co Ltd | ピペリジン誘導体 |
| JP3194355B2 (ja) * | 1996-10-24 | 2001-07-30 | 宇部興産株式会社 | ピペリジン化合物及びその製法 |
| DE69911373T2 (de) * | 1998-01-23 | 2004-07-01 | Vernalis Research Ltd., Winnersh | Azetidincarboxamidderivate zur behandlung von zns-erkrankungen |
| GB9917386D0 (en) * | 1999-07-23 | 1999-09-22 | Cerebrus Ltd | Chemical compounds-II |
| US6566356B2 (en) * | 2000-03-03 | 2003-05-20 | Aventis Pharma S.A. | Pharmaceutical compositions containing 3-aminoazetidine derivatives, novel derivatives and their preparation |
| NZ543322A (en) * | 2003-05-01 | 2009-03-31 | Vernalis Res Ltd | The use of azetidinecarboxamide derivates in therapy |
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2005
- 2005-10-31 ZA ZA200508831A patent/ZA200508831B/en unknown
- 2005-11-30 NO NO20055654A patent/NO20055654L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| NO20055654D0 (no) | 2005-11-30 |
| EA200501585A1 (ru) | 2006-06-30 |
| NO20055654L (no) | 2006-01-31 |
| CN1802350A (zh) | 2006-07-12 |
| EP1620395A1 (en) | 2006-02-01 |
| KR20060010770A (ko) | 2006-02-02 |
| US20070054891A1 (en) | 2007-03-08 |
| US7504522B2 (en) | 2009-03-17 |
| NZ543016A (en) | 2009-03-31 |
| DE602004024880D1 (de) | 2010-02-11 |
| MXPA05011670A (es) | 2005-12-15 |
| ATE453620T1 (de) | 2010-01-15 |
| WO2004096763A1 (en) | 2004-11-11 |
| EP1620395B1 (en) | 2009-12-30 |
| AU2004234125A1 (en) | 2004-11-11 |
| ZA200508831B (en) | 2007-03-28 |
| BRPI0409938A (pt) | 2006-04-25 |
| EA010583B1 (ru) | 2008-10-30 |
| JP2006525298A (ja) | 2006-11-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |