PE20140037A1 - Nuevo procedimiento de sintesis de la agomelatina - Google Patents
Nuevo procedimiento de sintesis de la agomelatinaInfo
- Publication number
- PE20140037A1 PE20140037A1 PE2013001435A PE2013001435A PE20140037A1 PE 20140037 A1 PE20140037 A1 PE 20140037A1 PE 2013001435 A PE2013001435 A PE 2013001435A PE 2013001435 A PE2013001435 A PE 2013001435A PE 20140037 A1 PE20140037 A1 PE 20140037A1
- Authority
- PE
- Peru
- Prior art keywords
- compound
- formula
- agomelatin
- reaction
- submit
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 abstract 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 238000006722 reduction reaction Methods 0.000 abstract 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 abstract 1
- 238000005899 aromatization reaction Methods 0.000 abstract 1
- 230000001351 cycling effect Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/18—Feminine contraceptives
-
- 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
-
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
-
- 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
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/37—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by etherified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
- C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
- C07C255/40—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by doubly-bound oxygen atoms
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Hospice & Palliative Care (AREA)
- Endocrinology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Gynecology & Obstetrics (AREA)
- Cardiology (AREA)
- Reproductive Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
SE REFIERE A UN PROCEDIMIENTO DE SINTESIS DE LA AGOMELATINA QUE COMPRENDE: A) HACER REACCIONAR EL CIANURO DE ALILO (CH2=CHCH2CN) CON UN COMPUESTO DE FORMULA (III) PARA OBTENER UN COMPUESTO DE FORMULA (IV) EN PRESENCIA DE CLOROBENCENO, DONDE Xa ES S-C(S)-OR, EN DONDE R ES ALQUILO(C1-C6); B) SOMETER EL COMPUESTO DE FORMULA (IV) A UNA REACCION DE CICLACION A UNA TEMPERATURA DE 130 A 135�C EN PRESENCIA DE UN CEBADOR RADICALARIO PARA FORMAR EL COMPUESTO DE FORMULA (V); C) SOMETER EL COMPUESTO (V) A UNA REACCION DE REDUCCION O DESHIDRATACION PARA FORMAR EL COMPUESTO DE FORMULA (VI) EN PRESENCIA DE ISOPROPOXIDO DE ALUMINIO; D) DICHO COMPUESTO (VI) SE SOMETE A UNA REACCION DE AROMATIZACION PARA FORMAR EL COMPUESTO DE FORMULA (VII) EN PRESENCIA DE UNA QUINONA; E) SOMETER EL COMPUESTO (VII) A UNA REDUCCION POR HIDROGENO EN PRESENCIA DE NIQUEL DE RANEY EN UN MEDIO PROTICO POLAR Y A UNA REACCION CON ANHIDRIDO ACETICO PARA OBTENER AGOMELATINA, EL CUAL SE AISLA EN LA FORMA DE UN SOLIDO
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1100024A FR2970000B1 (fr) | 2011-01-05 | 2011-01-05 | Nouveau procede de synthese de l'agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PE20140037A1 true PE20140037A1 (es) | 2014-02-01 |
Family
ID=44088993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PE2013001435A PE20140037A1 (es) | 2011-01-05 | 2012-01-04 | Nuevo procedimiento de sintesis de la agomelatina |
Country Status (43)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103058879B (zh) * | 2012-12-20 | 2015-09-09 | 安徽悦康凯悦制药有限公司 | 阿戈美拉汀的制备方法 |
| CN103804232B (zh) * | 2014-01-26 | 2015-08-19 | 江西同和药业股份有限公司 | 一种1-氰基-1-(7-甲氧基-3,4-二氢-1-萘基)甲醇酯类化合物及其制备方法和应用 |
| CN107353229B (zh) * | 2017-08-08 | 2019-04-30 | 许昌恒生制药有限公司 | 一种阿戈美拉汀中间体的制备方法 |
Family Cites Families (4)
| 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. |
| FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de 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 |
| 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 |
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2011
- 2011-01-05 FR FR1100024A patent/FR2970000B1/fr not_active Expired - Fee Related
- 2011-12-20 JO JOP/2011/0392A patent/JO3200B1/ar active
- 2011-12-30 UY UY0001033845A patent/UY33845A/es unknown
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2012
- 2012-01-03 SA SA112330134A patent/SA112330134B1/ar unknown
- 2012-01-04 RS RS20160320A patent/RS54753B9/sr unknown
- 2012-01-04 EP EP12703858.6A patent/EP2661422B9/fr active Active
- 2012-01-04 US US13/977,799 patent/US8853449B2/en not_active Ceased
- 2012-01-04 MX MX2013007837A patent/MX2013007837A/es active IP Right Grant
- 2012-01-04 PL PL12703858.6T patent/PL2661422T3/pl unknown
- 2012-01-04 GE GEAP201213180A patent/GEP20156365B/en unknown
- 2012-01-04 RU RU2013136344/04A patent/RU2550812C2/ru not_active IP Right Cessation
- 2012-01-04 TW TW101100368A patent/TWI438180B/zh not_active IP Right Cessation
- 2012-01-04 KR KR1020137020469A patent/KR101543432B1/ko not_active Expired - Fee Related
- 2012-01-04 ME MEP-2016-99A patent/ME02408B/me unknown
- 2012-01-04 HR HRP20160713TT patent/HRP20160713T1/hr unknown
- 2012-01-04 US US14/619,284 patent/USRE46218E1/en active Active
- 2012-01-04 CU CUP2013000092A patent/CU24289B1/es unknown
- 2012-01-04 AU AU2012220474A patent/AU2012220474B2/en not_active Ceased
- 2012-01-04 JP JP2013547894A patent/JP5837616B2/ja not_active Expired - Fee Related
- 2012-01-04 MY MYPI2013701043A patent/MY162977A/en unknown
- 2012-01-04 SG SG2013046370A patent/SG191733A1/en unknown
- 2012-01-04 WO PCT/FR2012/000005 patent/WO2012113999A1/fr not_active Ceased
- 2012-01-04 SI SI201230629A patent/SI2661422T1/sl unknown
- 2012-01-04 AP AP2013007022A patent/AP3609A/xx active
- 2012-01-04 PE PE2013001435A patent/PE20140037A1/es active IP Right Grant
- 2012-01-04 HU HUE12703858A patent/HUE028471T2/en unknown
- 2012-01-04 AR ARP120100020A patent/AR084780A1/es unknown
- 2012-01-04 BR BR112013017307A patent/BR112013017307A2/pt not_active IP Right Cessation
- 2012-01-04 EA EA201300794A patent/EA022077B1/ru unknown
- 2012-01-04 CA CA2823587A patent/CA2823587C/fr active Active
- 2012-01-04 CN CN201280004746.9A patent/CN103313965B/zh not_active Expired - Fee Related
- 2012-01-04 PH PH1/2013/501278A patent/PH12013501278A1/en unknown
- 2012-01-04 DK DK12703858.6T patent/DK2661422T3/en active
- 2012-01-04 ES ES12703858.6T patent/ES2583682T3/es active Active
- 2012-04-01 UA UAA201309590A patent/UA104122C2/uk unknown
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2013
- 2013-06-19 CR CR20130301A patent/CR20130301A/es unknown
- 2013-06-25 CL CL2013001882A patent/CL2013001882A1/es unknown
- 2013-06-25 TN TNP2013000274A patent/TN2013000274A1/fr unknown
- 2013-07-01 IL IL227281A patent/IL227281A/en active IP Right Grant
- 2013-07-03 CO CO13156552A patent/CO6731101A2/es unknown
- 2013-07-03 NI NI201300062A patent/NI201300062A/es unknown
- 2013-07-04 ZA ZA2013/05027A patent/ZA201305027B/en unknown
- 2013-07-05 EC ECSP13012735 patent/ECSP13012735A/es unknown
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2016
- 2016-07-11 CY CY20161100655T patent/CY1117774T1/el unknown
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| FG | Grant, registration |