CA2769820C - Method for making 3.alpha.-hydroxy, 3.beta.- methyl-5.alpha.-pregnan-20-one (ganaxolone) - Google Patents
Method for making 3.alpha.-hydroxy, 3.beta.- methyl-5.alpha.-pregnan-20-one (ganaxolone) Download PDFInfo
- Publication number
- CA2769820C CA2769820C CA2769820A CA2769820A CA2769820C CA 2769820 C CA2769820 C CA 2769820C CA 2769820 A CA2769820 A CA 2769820A CA 2769820 A CA2769820 A CA 2769820A CA 2769820 C CA2769820 C CA 2769820C
- Authority
- CA
- Canada
- Prior art keywords
- ganaxolone
- methyl
- methylating agent
- reaction
- dione
- 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.)
- Active
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/0015—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa
- C07J7/002—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group not substituted in position 17 alfa not substituted in position 16
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J5/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane and substituted in position 21 by only one singly bound oxygen atom, i.e. only one oxygen bound to position 21 by a single bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J7/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms
- C07J7/0005—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21
- C07J7/001—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group
- C07J7/004—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa
- C07J7/0045—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of two carbon atoms not substituted in position 21 substituted in position 20 by a keto group substituted in position 17 alfa not substituted in position 16
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US23355309P | 2009-08-13 | 2009-08-13 | |
| US61/233,553 | 2009-08-13 | ||
| PCT/US2010/045176 WO2011019821A2 (en) | 2009-08-13 | 2010-08-11 | METHOD FOR MAKING 3α-HYDROXY, 3β- METHYL-5α-PREGNAN-20-ONE (GANAXOLONE) |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2769820A1 CA2769820A1 (en) | 2011-02-17 |
| CA2769820C true CA2769820C (en) | 2017-06-27 |
Family
ID=43586809
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2769820A Active CA2769820C (en) | 2009-08-13 | 2010-08-11 | Method for making 3.alpha.-hydroxy, 3.beta.- methyl-5.alpha.-pregnan-20-one (ganaxolone) |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8362286B2 (enExample) |
| EP (1) | EP2464653B1 (enExample) |
| JP (1) | JP5745517B2 (enExample) |
| KR (1) | KR101778603B1 (enExample) |
| CN (1) | CN102549007B (enExample) |
| AU (1) | AU2010282570B2 (enExample) |
| BR (1) | BR112012003085B1 (enExample) |
| CA (1) | CA2769820C (enExample) |
| EA (1) | EA024269B1 (enExample) |
| ES (1) | ES2524724T3 (enExample) |
| IL (1) | IL217857A (enExample) |
| MX (1) | MX2012001728A (enExample) |
| NZ (1) | NZ597940A (enExample) |
| WO (1) | WO2011019821A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2812250T3 (es) | 2005-11-28 | 2021-03-16 | Marinus Pharmaceuticals Inc | Formulaciones de ganaxolona y procedimientos para la preparación y uso de las mismas |
| US9629853B2 (en) | 2014-05-21 | 2017-04-25 | Wisconsin Alumni Research Foundation | Uses of ganaxolone |
| CZ305837B6 (cs) * | 2015-02-25 | 2016-03-30 | Vysoká škola chemicko - technologická v Praze | (3α,5β,20S)-3-Nitrooxy-pregnan-20-karboxylová kyselina |
| AU2016338672A1 (en) * | 2015-10-16 | 2018-04-12 | Marinus Pharmaceuticals, Inc. | Injectable neurosteroid formulations containing nanoparticles |
| CN106366149B (zh) * | 2016-08-09 | 2018-01-23 | 南京臣功制药股份有限公司 | 一种醋酸甲羟孕酮分散片的有关物质及其分析检测方法 |
| CN106279326A (zh) * | 2016-08-09 | 2017-01-04 | 南京臣功制药股份有限公司 | 一种醋酸甲羟孕酮胶囊的有关物质及其分析检测方法 |
| EP4233861A3 (en) | 2016-08-11 | 2023-10-11 | Ovid Therapeutics, Inc. | Compositions for treatment of essential tremor |
| US10391105B2 (en) | 2016-09-09 | 2019-08-27 | Marinus Pharmaceuticals Inc. | Methods of treating certain depressive disorders and delirium tremens |
| IT201800009683A1 (it) * | 2018-10-22 | 2020-04-22 | Ind Chimica Srl | Processo per la preparazione di 3α-idrossi-5α-pregnan-20-one (brexanolone) |
| US11266662B2 (en) | 2018-12-07 | 2022-03-08 | Marinus Pharmaceuticals, Inc. | Ganaxolone for use in prophylaxis and treatment of postpartum depression |
| CN114728012A (zh) | 2019-08-05 | 2022-07-08 | 马瑞纳斯制药公司 | 用于治疗癫痫持续状态的加奈索酮 |
| CN114828889B (zh) | 2019-12-06 | 2025-02-14 | 马瑞纳斯制药公司 | 用于治疗结节性硬化症的加奈索酮 |
| IT202000021316A1 (it) | 2020-09-09 | 2022-03-09 | Ind Chimica Srl | PROCESSO PER LA PREPARAZIONE DI (3α,5α)-3-IDROSSI-3-METIL-PREGNAN-20-ONE (GANAXOLONE) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953429A (en) * | 1970-12-17 | 1976-04-27 | Glaxo Laboratories Limited | Anaesthetic steroids of the androstance and pregnane series |
| US5232917A (en) * | 1987-08-25 | 1993-08-03 | University Of Southern California | Methods, compositions, and compounds for allosteric modulation of the GABA receptor by members of the androstane and pregnane series |
| US5319115A (en) * | 1987-08-25 | 1994-06-07 | Cocensys Inc. | Method for making 3α-hydroxy, 3β-substituted-pregnanes |
| AU698834B2 (en) * | 1993-05-24 | 1998-11-12 | Purdue Pharma Ltd. | Methods and compositions for inducing sleep |
| FR2720747B1 (fr) * | 1994-06-02 | 1996-07-12 | Roussel Uclaf | Nouveau procédé de préparation d'un stéroïde 16béta-méthyl et nouveaux intermédiaires. |
| AP653A (en) * | 1994-11-23 | 1998-07-21 | Cocensys Inc | Androstane and pregnane series for allosteric modulations of gaba receptor. |
| WO2006010085A1 (en) * | 2004-07-09 | 2006-01-26 | Roxro Pharma, Inc. | Use of neurosteroids to treat neuropathic pain |
| ES2812250T3 (es) * | 2005-11-28 | 2021-03-16 | Marinus Pharmaceuticals Inc | Formulaciones de ganaxolona y procedimientos para la preparación y uso de las mismas |
-
2010
- 2010-08-11 MX MX2012001728A patent/MX2012001728A/es active IP Right Grant
- 2010-08-11 CA CA2769820A patent/CA2769820C/en active Active
- 2010-08-11 WO PCT/US2010/045176 patent/WO2011019821A2/en not_active Ceased
- 2010-08-11 ES ES10808696.8T patent/ES2524724T3/es active Active
- 2010-08-11 AU AU2010282570A patent/AU2010282570B2/en active Active
- 2010-08-11 NZ NZ597940A patent/NZ597940A/xx unknown
- 2010-08-11 EA EA201270241A patent/EA024269B1/ru active IP Right Revival
- 2010-08-11 EP EP10808696.8A patent/EP2464653B1/en active Active
- 2010-08-11 BR BR112012003085-0A patent/BR112012003085B1/pt active IP Right Grant
- 2010-08-11 JP JP2012524841A patent/JP5745517B2/ja active Active
- 2010-08-11 US US12/854,226 patent/US8362286B2/en active Active
- 2010-08-11 CN CN201080035660.3A patent/CN102549007B/zh active Active
- 2010-08-11 KR KR1020127006429A patent/KR101778603B1/ko active Active
-
2012
- 2012-01-31 IL IL217857A patent/IL217857A/en active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| US8362286B2 (en) | 2013-01-29 |
| HK1171761A1 (en) | 2013-04-05 |
| MX2012001728A (es) | 2012-06-01 |
| IL217857A0 (en) | 2012-03-29 |
| JP5745517B2 (ja) | 2015-07-08 |
| KR101778603B1 (ko) | 2017-09-14 |
| JP2013501803A (ja) | 2013-01-17 |
| BR112012003085A2 (pt) | 2020-12-01 |
| EP2464653A4 (en) | 2013-01-16 |
| US20110040112A1 (en) | 2011-02-17 |
| CN102549007B (zh) | 2015-03-18 |
| KR20120084715A (ko) | 2012-07-30 |
| EA201270241A1 (ru) | 2013-09-30 |
| CA2769820A1 (en) | 2011-02-17 |
| WO2011019821A2 (en) | 2011-02-17 |
| ES2524724T3 (es) | 2014-12-11 |
| AU2010282570A1 (en) | 2012-02-23 |
| BR112012003085B1 (pt) | 2021-06-01 |
| EP2464653A2 (en) | 2012-06-20 |
| NZ597940A (en) | 2013-03-28 |
| EA024269B1 (ru) | 2016-09-30 |
| CN102549007A (zh) | 2012-07-04 |
| WO2011019821A3 (en) | 2011-06-16 |
| EP2464653B1 (en) | 2014-10-22 |
| AU2010282570B2 (en) | 2014-04-24 |
| IL217857A (en) | 2016-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2464653B1 (en) | Method for making 3 -hydroxy, 3 - methyl-5 -pregnan-20-one (ganaxolone) | |
| EP3645548B1 (en) | Methods for preparing bile acids | |
| CA2859852C (en) | Process for alkynylating 16-substituted-17-keto steroids | |
| WO2015102022A2 (en) | An improved process for the preparation of abiraterone acetate | |
| EP2596007A1 (en) | Process for the preparation of 17-desoxy-corticosteroids | |
| CN103772468A (zh) | 醋酸特拉司酮及其中间体的制备方法和用途 | |
| CN110950920A (zh) | 一种四烯雌酮的制备方法 | |
| HK1171761B (en) | METHOD FOR MAKING 3α-HYDROXY, 3β- METHYL-5α-PREGNAN-20-ONE (GANAXOLONE) | |
| CN103819436A (zh) | (3aR,4R,5R,6aS)-4-((E)-3,3-二氟-4-苯氧基丁-1-烯-1-基)-2-氧代六氢-2H-环戊烷[b]呋喃-5-基苯甲酸酯的一种晶型及相应晶体的制备方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20150728 |
|
| MPN | Maintenance fee for patent paid |
Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 14TH ANNIV.) - STANDARD Year of fee payment: 14 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20240724 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL Effective date: 20240726 |
|
| MPN | Maintenance fee for patent paid |
Free format text: FEE DESCRIPTION TEXT: MF (PATENT, 15TH ANNIV.) - STANDARD Year of fee payment: 15 |
|
| U00 | Fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U00-U101 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE REQUEST RECEIVED Effective date: 20250709 |
|
| U11 | Full renewal or maintenance fee paid |
Free format text: ST27 STATUS EVENT CODE: A-4-4-U10-U11-U102 (AS PROVIDED BY THE NATIONAL OFFICE); EVENT TEXT: MAINTENANCE FEE PAYMENT PAID IN FULL Effective date: 20250709 |