CU20120163A7 - Intermedios de agomelatina y método de preparación de éstos - Google Patents
Intermedios de agomelatina y método de preparación de éstosInfo
- Publication number
- CU20120163A7 CU20120163A7 CUP2012000163A CU20120163A CU20120163A7 CU 20120163 A7 CU20120163 A7 CU 20120163A7 CU P2012000163 A CUP2012000163 A CU P2012000163A CU 20120163 A CU20120163 A CU 20120163A CU 20120163 A7 CU20120163 A7 CU 20120163A7
- Authority
- CU
- Cuba
- Prior art keywords
- agomelatine
- preparation
- intermediate compounds
- intermediates
- present
- Prior art date
Links
- 239000000543 intermediate Substances 0.000 title abstract 8
- 238000000034 method Methods 0.000 title abstract 4
- 238000002360 preparation method Methods 0.000 title abstract 4
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 abstract 5
- 229960002629 agomelatine Drugs 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 3
- GABLTKRIYDNDIN-UHFFFAOYSA-N 7-methoxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound C1CCC(=O)C2=CC(OC)=CC=C21 GABLTKRIYDNDIN-UHFFFAOYSA-N 0.000 abstract 1
- 229940126062 Compound A Drugs 0.000 abstract 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000009776 industrial production Methods 0.000 abstract 1
- 238000000746 purification Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- 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
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
-
- 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
- A61P25/06—Antimigraine agents
-
- 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
- A61P25/20—Hypnotics; Sedatives
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/18—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Battery Electrode And Active Subsutance (AREA)
Abstract
La presente invención se refiere a los compuestos intermedios para la preparación de agomelatina, así como a los métodos de preparación de éstos.El intermedio de la presente invención para la preparación de agomelatina es el compuesto A y/o el compuesto B como se muestra en la fórmula siguiente. También se proporcionan dos compuestos intermedios nuevos.Cuando se usan estos compuestos intermedios nuevos para preparar agomelatina, es sencillo de manipular,bien controlado y con alta pureza, sin operaciones complicadas tales como rectificación y separación por cromatografía en columna, y adecuado para la producción industrial. Por otro lado, los métodos de preparación de los dos intermedios nuevos en sí mismos son sencillos y con alto rendimiento, usando sólo la usada muy comúnmente 7-metoxi-tetralona como material de partida original y que experimenta una etapa de reacción para obtener los intermedios, seguido de una etapa más para convertir los compuestos intermedios en el producto deseado agomelatina.Dichos procesos de reacción están muy simplificados, mejorándose el rendimiento de la reacción y superando la dificultad de purificación del método previo, comparado con la técnica anterior para la preaparación de agomelatina.Típicamente, el rendimiento de la presente invención es mayor del 70%. Espacio para Fórmula
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010101973700A CN102276492B (zh) | 2010-06-08 | 2010-06-08 | 阿戈美拉汀中间体及其制备方法 |
| PCT/CN2011/075438 WO2011153939A1 (en) | 2010-06-08 | 2011-06-08 | Agomelatine intermediates and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CU20120163A7 true CU20120163A7 (es) | 2013-01-30 |
| CU24148B1 CU24148B1 (es) | 2016-02-29 |
Family
ID=45097542
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CU20120163A CU24148B1 (es) | 2010-06-08 | 2011-06-08 | Intermedios de agomelatina y método de preparación de éstos |
Country Status (41)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2012046253A2 (en) * | 2010-10-08 | 2012-04-12 | Msn Laboratories Limited | Process for the preparation of n-[2- (7-methoxy-l-naphthyl) ethyl] acetamide and its novel crystalline forms |
| CN102452951B (zh) * | 2010-10-25 | 2014-02-19 | 天津泰普药品科技发展有限公司 | 阿戈美拉汀及其药物组合物 |
| ITMI20121444A1 (it) | 2012-08-27 | 2014-02-28 | Procos Spa | Processo per la produzione di agomelatine |
| EP2921473B1 (en) * | 2012-10-09 | 2017-09-27 | Jiangxi Synergy Pharmaceutical Co. Ltd. | 1-cyan-1-(7-methoxyl-1-naphtyl) methanol ester compound and preparation method and use thereof |
| CN112574066B (zh) * | 2019-09-27 | 2024-10-25 | 江苏豪森药业集团有限公司 | 一种阿戈美拉汀中间体的制备方法 |
| EP4081505A1 (en) * | 2019-12-23 | 2022-11-02 | DSM IP Assets B.V. | Dehydrogenation process |
| CN117964510A (zh) * | 2024-01-31 | 2024-05-03 | 浙江东亚药业股份有限公司 | 一种阿戈美拉汀的制备方法 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2658818B1 (fr) * | 1990-02-27 | 1993-12-31 | Adir Cie | Nouveaux derives a structure naphtalenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent. |
| DE10229842A1 (de) | 2002-07-03 | 2004-02-05 | Helmut Prof. Dr. Schmidhammer | Morphinanderivate und deren quartäre Ammoniumsalze substituiert in Position 14, Herstellungsverfahren und Verwendung |
| FR2866336B1 (fr) * | 2004-02-13 | 2006-03-24 | Servier Lab | Nouveau procede de synthese du (7-methoxy-3,4-dihydro-1-naphtalenyl) acetonitrile et application a la synthese de l'agomelatine |
| FR2866334B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese du (7-methoxy-1-naphtyl) acetonitrile et application a la synthese de l'agomelatine |
| FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| MX2008015843A (es) * | 2006-06-20 | 2009-01-09 | Hoffmann La Roche | Derivados de tetralina e indano y usos de los mismos. |
| CN101486665B (zh) * | 2009-03-03 | 2013-04-17 | 上海医药工业研究院 | 阿戈美拉汀中间体2-(7-甲氧基-1-萘基)乙酰胺的制备方法 |
| EP2705023A4 (en) * | 2011-01-04 | 2014-11-19 | Symed Labs Ltd | PROCESSES FOR THE PREPARATION OF N- [2- (7-METHOXY-1-NAPHTHYLLELYHYL) ACETAMIDE |
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2010
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2011
- 2011-06-08 KR KR1020137000375A patent/KR101470874B1/ko not_active Expired - Fee Related
- 2011-06-08 AU AU2011264206A patent/AU2011264206B2/en not_active Ceased
- 2011-06-08 ES ES11791930.8T patent/ES2656968T3/es active Active
- 2011-06-08 UA UAA201300117A patent/UA104684C2/ru unknown
- 2011-06-08 AP AP2013006659A patent/AP3205A/xx active
- 2011-06-08 MX MX2012013870A patent/MX2012013870A/es active IP Right Grant
- 2011-06-08 JP JP2013513535A patent/JP5519863B2/ja not_active Expired - Fee Related
- 2011-06-08 SG SG2012085296A patent/SG185667A1/en unknown
- 2011-06-08 LT LTEP11791930.8T patent/LT2580189T/lt unknown
- 2011-06-08 HU HUE11791930A patent/HUE035850T2/en unknown
- 2011-06-08 DK DK11791930.8T patent/DK2580189T3/da active
- 2011-06-08 RS RS20171239A patent/RS56659B1/sr unknown
- 2011-06-08 WO PCT/CN2011/075438 patent/WO2011153939A1/en not_active Ceased
- 2011-06-08 EP EP11791930.8A patent/EP2580189B1/en active Active
- 2011-06-08 PL PL11791930T patent/PL2580189T3/pl unknown
- 2011-06-08 PE PE2012002205A patent/PE20130252A1/es active IP Right Grant
- 2011-06-08 NZ NZ604081A patent/NZ604081A/en not_active IP Right Cessation
- 2011-06-08 PT PT117919308T patent/PT2580189T/pt unknown
- 2011-06-08 US US13/702,388 patent/US8779199B2/en active Active
- 2011-06-08 PH PH1/2012/502275A patent/PH12012502275A1/en unknown
- 2011-06-08 SI SI201131371T patent/SI2580189T1/en unknown
- 2011-06-08 GE GEAP201112941A patent/GEP20156234B/en unknown
- 2011-06-08 ME MEP-2018-6A patent/ME02992B/me unknown
- 2011-06-08 CA CA2801822A patent/CA2801822C/en not_active Expired - Fee Related
- 2011-06-08 BR BR112012031086-0A patent/BR112012031086B1/pt not_active IP Right Cessation
- 2011-06-08 HR HRP20171751TT patent/HRP20171751T1/hr unknown
- 2011-06-08 MY MYPI2012700965A patent/MY160954A/en unknown
- 2011-06-08 MA MA35423A patent/MA34292B1/fr unknown
- 2011-06-08 NO NO11791930A patent/NO2580189T3/no unknown
- 2011-06-08 CU CU20120163A patent/CU24148B1/es active IP Right Grant
- 2011-06-08 EA EA201201666A patent/EA020271B1/ru unknown
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2012
- 2012-11-21 ZA ZA2012/08764A patent/ZA201208764B/en unknown
- 2012-11-21 TN TNP2012000542A patent/TN2012000542A1/en unknown
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2018
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant of patent |