AR084779A1 - Procedimiento de sintesis de la agomelatina - Google Patents
Procedimiento de sintesis de la agomelatinaInfo
- Publication number
- AR084779A1 AR084779A1 ARP120100019A ARP120100019A AR084779A1 AR 084779 A1 AR084779 A1 AR 084779A1 AR P120100019 A ARP120100019 A AR P120100019A AR P120100019 A ARP120100019 A AR P120100019A AR 084779 A1 AR084779 A1 AR 084779A1
- Authority
- AR
- Argentina
- Prior art keywords
- formula
- compound
- give rise
- group
- function
- 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
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 title 1
- 229960002629 agomelatine Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- 150000001412 amines Chemical group 0.000 abstract 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical group CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 abstract 2
- IFCIFYPGYHSAOT-UHFFFAOYSA-N 1-(4-methoxyphenyl)pent-4-en-1-one Chemical compound COC1=CC=C(C(=O)CCC=C)C=C1 IFCIFYPGYHSAOT-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 238000005899 aromatization reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000018044 dehydration Effects 0.000 abstract 1
- 238000006297 dehydration reaction Methods 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- -1 vinyl halide Chemical class 0.000 abstract 1
- 229920002554 vinyl polymer Polymers 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the 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
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
- C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
-
- 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)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Psychology (AREA)
- Pain & Pain Management (AREA)
- Gynecology & Obstetrics (AREA)
- Endocrinology (AREA)
- Reproductive Health (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Indole Compounds (AREA)
- Inorganic Compounds Of Heavy Metals (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Reivindicación 1: Procedimiento de síntesis industrial del compuesto de fórmula (1) caracterizado porque se hace reaccionar la 1-(4-metoxifenil)-4-penten-1-ona de fórmula (2) con un compuesto de fórmula (3) en presencia de un cebador radicalario, en la que R’ y R’’, idénticos o diferentes, representan cada uno un grupo alquilo C1-6 lineal o ramificado, o bien R’ y R’’ forman juntos una cadena alquileno C2-3, pudiendo estar el ciclo así formado fusionado con un fenilo, y Xa representa un grupo -S-C(S)-OR en el que R representa un grupo alquilo C1-6 lineal o ramificado, para dar lugar al aducto de fórmula (4) en la que R, R’, R’’ son tales como se han definido anteriormente, compuesto de fórmula (4) que puede aislarse opcionalmente, cuya función amina puede desprotegerse opcionalmente y convertirse en una función acetamida, el cual se somete a una reacción de ciclación en presencia de un cebador radicalario para formar el compuesto de fórmula (5) entendiéndose que el grupo del anillo N designa una amina protegida definida en el grupo de formulas (6) en la que R’ y R” se definen tal como anteriormente, compuesto de fórmula (5) cuya función amina puede desprotegerse opcionalmente, dicho compuesto de fórmula (5) se somete bien a una reducción/esterificación seguida de una deshidratación, bien se transforma en halogenuro vinílico para dar lugar al compuesto de fórmula (7) en la que Y representa un átomo de halógeno o un átomo de hidrógeno, teniendo el grupo del anillo N la misma definición que anteriormente, compuesto de fórmula (7) cuya función amina protegida se convierte en función acetamida llegado el caso, es decir, cuando esta conversión no ha tenido lugar antes, para dar lugar al compuesto de fórmula (8) en la que Y es tal como se ha definido anteriormente, el cual se somete finalmente a una reacción de aromatización para dar lugar al compuesto de fórmula (1) que se aísla en la forma de un sólido.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1100023A FR2970001B1 (fr) | 2011-01-05 | 2011-01-05 | Nouveau procede de synthese de l'agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR084779A1 true AR084779A1 (es) | 2013-06-26 |
Family
ID=44121614
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120100019A AR084779A1 (es) | 2011-01-05 | 2012-01-04 | Procedimiento de sintesis de la agomelatina |
Country Status (42)
Family Cites Families (3)
| 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 |
| FR2934859B1 (fr) * | 2008-08-05 | 2010-08-13 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
-
2011
- 2011-01-05 FR FR1100023A patent/FR2970001B1/fr not_active Expired - Fee Related
- 2011-12-20 JO JOP/2011/0391A patent/JO3085B1/ar active
- 2011-12-30 UY UY0001033847A patent/UY33847A/es unknown
-
2012
- 2012-01-02 SA SA112330135A patent/SA112330135B1/ar unknown
- 2012-01-04 AU AU2012204817A patent/AU2012204817B2/en not_active Ceased
- 2012-01-04 CU CUP2013000087A patent/CU24291B1/es unknown
- 2012-01-04 BR BR112013017264A patent/BR112013017264A2/pt not_active IP Right Cessation
- 2012-01-04 JP JP2013547893A patent/JP5837615B2/ja not_active Expired - Fee Related
- 2012-01-04 CA CA2823584A patent/CA2823584C/fr active Active
- 2012-01-04 TW TW101100371A patent/TWI534127B/zh not_active IP Right Cessation
- 2012-01-04 CN CN201280004722.3A patent/CN103298779B/zh not_active Expired - Fee Related
- 2012-01-04 DK DK12703857.8T patent/DK2661423T3/da active
- 2012-01-04 US US13/977,796 patent/US8871975B2/en active Active
- 2012-01-04 KR KR1020137020467A patent/KR101544129B1/ko active IP Right Grant
- 2012-01-04 SI SI201230217T patent/SI2661423T1/sl unknown
- 2012-01-04 WO PCT/FR2012/000004 patent/WO2012093225A1/fr active Application Filing
- 2012-01-04 SG SG2013046354A patent/SG191191A1/en unknown
- 2012-01-04 ME MEP-2015-60A patent/ME02109B/me unknown
- 2012-01-04 MY MYPI2013701042A patent/MY162973A/en unknown
- 2012-01-04 GE GEAP201213179A patent/GEP201606576B/en unknown
- 2012-01-04 EP EP12703857.8A patent/EP2661423B1/fr active Active
- 2012-01-04 MX MX2013007838A patent/MX2013007838A/es active IP Right Grant
- 2012-01-04 PT PT127038578T patent/PT2661423E/pt unknown
- 2012-01-04 AR ARP120100019A patent/AR084779A1/es unknown
- 2012-01-04 ES ES12703857.8T patent/ES2539173T3/es active Active
- 2012-01-04 PE PE2013001436A patent/PE20140169A1/es active IP Right Grant
- 2012-01-04 RS RS20150268A patent/RS53958B1/en unknown
- 2012-01-04 AP AP2013007024A patent/AP3399A/xx active
- 2012-01-04 EA EA201300793A patent/EA024126B1/ru unknown
- 2012-01-04 PL PL12703857T patent/PL2661423T3/pl unknown
- 2012-04-01 UA UAA201309591A patent/UA104123C2/uk unknown
-
2013
- 2013-06-19 CR CR20130300A patent/CR20130300A/es unknown
- 2013-06-25 CL CL2013001881A patent/CL2013001881A1/es unknown
- 2013-06-25 TN TNP2013000273A patent/TN2013000273A1/fr unknown
- 2013-07-01 IL IL227282A patent/IL227282A/en active IP Right Grant
- 2013-07-03 GT GT201300176A patent/GT201300176A/es unknown
- 2013-07-03 CO CO13156553A patent/CO6731102A2/es unknown
- 2013-07-03 NI NI201300061A patent/NI201300061A/es unknown
- 2013-07-04 ZA ZA2013/05026A patent/ZA201305026B/en unknown
-
2014
- 2014-03-06 HK HK14102274.7A patent/HK1189217A1/xx not_active IP Right Cessation
-
2015
- 2015-05-12 HR HRP20150504TT patent/HRP20150504T1/hr unknown
- 2015-06-10 CY CY20151100504T patent/CY1116366T1/el unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |