HRP20120407T1 - Postupak priprave agomelatina - Google Patents
Postupak priprave agomelatina Download PDFInfo
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- HRP20120407T1 HRP20120407T1 HRP20120407AT HRP20120407T HRP20120407T1 HR P20120407 T1 HRP20120407 T1 HR P20120407T1 HR P20120407A T HRP20120407A T HR P20120407AT HR P20120407 T HRP20120407 T HR P20120407T HR P20120407 T1 HRP20120407 T1 HR P20120407T1
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- agomelatine
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- 238000000034 method Methods 0.000 title claims abstract 12
- 150000001875 compounds Chemical class 0.000 claims abstract 29
- 230000015572 biosynthetic process Effects 0.000 claims abstract 15
- 238000003786 synthesis reaction Methods 0.000 claims abstract 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 3
- KUKJAAZDXZNNPD-UHFFFAOYSA-N 7-methoxynaphthalen-1-ol Chemical compound C1=CC=C(O)C2=CC(OC)=CC=C21 KUKJAAZDXZNNPD-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 229910052763 palladium Inorganic materials 0.000 claims abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 claims abstract 2
- YJYPHIXNFHFHND-UHFFFAOYSA-N agomelatine Chemical compound C1=CC=C(CCNC(C)=O)C2=CC(OC)=CC=C21 YJYPHIXNFHFHND-UHFFFAOYSA-N 0.000 claims 7
- 229960002629 agomelatine Drugs 0.000 claims 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- RGDNOAUQSNCJIE-UHFFFAOYSA-N 2-[2-(7-methoxynaphthalen-1-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC1=CC=CC2=CC=C(OC)C=C21 RGDNOAUQSNCJIE-UHFFFAOYSA-N 0.000 claims 1
- IGDLZDCWMRPMGL-UHFFFAOYSA-N 2-ethenylisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(C=C)C(=O)C2=C1 IGDLZDCWMRPMGL-UHFFFAOYSA-N 0.000 claims 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 229910002056 binary alloy Inorganic materials 0.000 claims 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 235000017281 sodium acetate Nutrition 0.000 claims 1
- 239000001632 sodium acetate Substances 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
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- 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
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- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/08—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of a saturated carbon skeleton containing rings
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- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C233/11—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to carbon atoms of an unsaturated carbon skeleton containing six-membered aromatic rings
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- 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
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- 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
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Abstract
Postupak za industrijsku sintezu spoja formule (I) naznačen time, da se izlaže reakciji spoj 7-metoksi-1-naftol formule (II): u kojem se kondenzira, u nazočnosti paladija, nakon konverzije hidroksi funkcije u odlazeću skupinu poput halogen, tosilatne ili trifluormetansulfonatne skupine, spoj formule (III): CH2=CH-R (III), u kojem R predstavlja skupinupri čemu R' i R", koji mogu biti jednaki ili različiti, svaki za sebe predstavljaju ravnu ili razgrananu skupinu
Claims (11)
1. Postupak za industrijsku sintezu spoja formule (I)
[image]
naznačen time, da se izlaže reakciji spoj 7-metoksi-1-naftol formule (II):
[image]
u kojem se kondenzira, u nazočnosti paladija, nakon konverzije hidroksi funkcije u odlazeću skupinu poput halogen, tosilatne ili trifluormetansulfonatne skupine, spoj formule (III): CH2=CH-R (III), u kojem R predstavlja skupinu
[image]
pri čemu R' i R”, koji mogu biti jednaki ili različiti, svaki za sebe predstavljaju ravnu ili razgrananu skupinu (C1-C6)alkil ili R' i R” zajedno tvore (C2-C3)alkilenski lanac, a prsten koji se na taj način dobije može se stopiti s fenilnom skupinom, čime se dobiva spoj formule (IV):
[image]
pri čemu R je definiran jednako kao u prethodnom tekstu,
koji se podvrgava katalitičkoj hidrogenaciji, čime se dobiva spoj formule (V):
[image]
pri čemu R je definiran jednako kao u prethodnom tekstu,
koji se izlaže hidrolizi lužinom ili kiselinom ili djelovanju binarnog sustava redukcijsko sredstvo/kiselina, čime se dobiva spoj formule (VI) ili njegov hidroklorid:
[image]
koji se uspješno izlaže djelovanju natrijevog acetata, zatim octenog anhidrida, čime se dobiva spoj formule (I), koji se izdvaja u obliku krutine.
2. Postupak za sintezu spoja formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je spoj formule (III) N-vinilftalimid.
3. Postupak za sintezu spoja formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da je spoj formule (III) akrilamid.
4. Postupak za sintezu spoja formule (I) u skladu s patentnim zahtjevom 1, naznačen time, da se kondenzacija spoja formule (III) radi dobivanja spoja formule (IV) provodi uporabom tetrakis(trifenilfosfin)-paladija.
5. Spoj formule (IV) u skladu s patentnim zahtjevom 1, naznačen time, da se koristi kao međuspoj u sintezi agomelatina.
6. Uporaba spoja formule (IV) u skladu s patentnim zahtjevom 5, naznačena time, da se dotični spoj koristi u sintezi agomelatina.
7. Uporaba spoja formule (II) u skladu s patentnim zahtjevom 1, naznačena time, da se dotični spoj koristi u sintezi agomelatina.
8. Uporaba spoja formule (V) u skladu s patentnim zahtjevom 1 u sintezi agomelatina, naznačena time, da se ta uporaba ne odnosi na 2-[2-(7-metoksi-1-naftil)etil]-1H-izoindol-1,3(2H)-dion.
9. Postupak za sintezu agomelatina u skladu s patentnim zahtjevom 1 u kojem je početna tvar spoj formule (IV), naznačen time, da se spoj formule (IV) dobiva postupkom sinteze u skladu s jednim od patentnih zahtjeva 1 do 4.
10. Postupak za sintezu agomelatina u skladu s patentnim zahtjevom 1 u kojem je početna tvar spoj formule (V), naznačen time, da se spoj formule (V) dobiva postupkom sinteze u skladu s jednim od patentnih zahtjeva 1 do 4.
11. Postupak za sintezu agomelatina u skladu s patentnim zahtjevom 1 u kojem je početna tvar spoj formule (VI), naznačen time, da se spoj formule (VI) dobiva postupkom sinteze u skladu s jednim od patentnih zahtjeva 1 do 4.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0804465A FR2934859B1 (fr) | 2008-08-05 | 2008-08-05 | Nouveau procede de synthese de l'agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20120407T1 true HRP20120407T1 (hr) | 2012-06-30 |
Family
ID=40352219
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20120407AT HRP20120407T1 (hr) | 2008-08-05 | 2012-05-11 | Postupak priprave agomelatina |
Country Status (47)
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102190594A (zh) | 2010-03-17 | 2011-09-21 | 上海医药工业研究院 | 阿戈美拉汀氯化氢水合物及其制备方法 |
| WO2011154140A2 (en) | 2010-06-10 | 2011-12-15 | Gador S.A. | New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide and new crystalline form |
| CN102229541A (zh) * | 2010-09-17 | 2011-11-02 | 福建广生堂药业有限公司 | 阿戈美拉汀n-[2-(7-甲氧基萘-1-基)乙基]乙酰胺的制备方法 |
| CN102531956B (zh) * | 2010-12-21 | 2014-07-09 | 浙江九洲药业股份有限公司 | 用于制备阿戈美拉汀的中间体及相关制备方法 |
| FR2970001B1 (fr) * | 2011-01-05 | 2013-01-04 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| EP2562151A1 (en) * | 2011-08-25 | 2013-02-27 | Dr. Reddy's Laboratories Ltd. | Processes for the preparation of agomelatine and its intermediates |
| ITMI20121444A1 (it) | 2012-08-27 | 2014-02-28 | Procos Spa | Processo per la produzione di agomelatine |
| WO2014072998A1 (en) | 2012-11-07 | 2014-05-15 | Cadila Healthcare Limited | An improved process for preparation of agomelatine |
| JP6159415B2 (ja) * | 2013-11-20 | 2017-07-05 | マナック株式会社 | 含臭素ｎ−フェニルジアクリルイミド誘導体及びその製造方法 |
| FR3014434B1 (fr) * | 2013-12-05 | 2015-12-25 | Servier Lab | Nouveau procede de synthese du 7-methoxy-naphtalene-1-carbaldehyde et application a la synthese de l'agomelatine |
| FR3014437B1 (fr) * | 2013-12-05 | 2016-12-23 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| CN114394906A (zh) * | 2022-03-24 | 2022-04-26 | 中孚药业股份有限公司 | 一种阿戈美拉汀中间体的制备方法 |
| CN115872887B (zh) * | 2022-12-30 | 2023-07-07 | 上海国创医药股份有限公司 | 一种阿戈美拉汀的制备方法 |
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| 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. |
| DE19825454A1 (de) * | 1998-06-06 | 1999-12-16 | Aventis Res & Tech Gmbh & Co | Verfahren zur Herstellung von aromatischen Olefinen unter Katalyse von Palladiumkatalysatoren mit Phosphitliganden |
| FR2784375B1 (fr) * | 1998-10-12 | 2000-11-24 | Adir | Nouveaux derives cycliques a chaine cycloalkylenique, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| DE19859684A1 (de) * | 1998-12-23 | 2000-06-29 | Bayer Ag | Verfahren zur Herstellung von Fluor enthaltenden Phenethylaminen sowie neue, Fluor enthalende beta-Iminovinyl- und beta-Iminoethylbenzole |
| DE19931116A1 (de) * | 1999-07-06 | 2001-01-11 | Bayer Ag | Verfahren zur Herstellung von Phenethylaminen und neue chemische Verbindungen |
| FR2866335B1 (fr) * | 2004-02-13 | 2006-05-26 | Servier Lab | Nouveau procede de synthese de l'agomelatine |
| EP1732531A2 (en) * | 2004-02-25 | 2006-12-20 | La Jolla Pharmaceutical Company | Amines and amides for the treatment of diseases |
| JP4870660B2 (ja) * | 2004-03-15 | 2012-02-08 | アノーメッド インコーポレイティド | Ｃｘｃｒ４アンタゴニストの合成プロセス |
| JP5015016B2 (ja) * | 2006-02-07 | 2012-08-29 | 大正製薬株式会社 | １０ａ−アザライド化合物 |
| CN101638376B (zh) | 2008-07-29 | 2011-04-27 | 江苏恩华药业股份有限公司 | 阿戈美拉汀的制备方法及其中间体 |
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