RS50545B - Novi postupak sinteze (7-metoksi-3,4-dihidro-1-naftalenil) acetonitrila i primena u sintezi agomelatina - Google Patents
Novi postupak sinteze (7-metoksi-3,4-dihidro-1-naftalenil) acetonitrila i primena u sintezi agomelatinaInfo
- Publication number
- RS50545B RS50545B RSP-2008/0039A RSP20080039A RS50545B RS 50545 B RS50545 B RS 50545B RS P20080039 A RSP20080039 A RS P20080039A RS 50545 B RS50545 B RS 50545B
- Authority
- RS
- Serbia
- Prior art keywords
- formula
- branched
- compound
- linear
- methoxy
- 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
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 title 3
- 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
- 230000002194 synthesizing effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 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
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000003637 basic solution Substances 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 230000001419 dependent effect Effects 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 238000003379 elimination reaction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 238000001953 recrystallisation Methods 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- 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
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/32—Separation; Purification; Stabilisation; Use of additives
-
- 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
- C07C255/33—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 with cyano groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by saturated carbon chains
-
- 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
- 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)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Child & Adolescent Psychology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Postupak industrijske sinteze jedinjenja formule (I) naznačen time što se podvrgava reakciji 7-metoksi-1-tetralon formule (IV): sa cijanosirćetnom kiselinom formule (V): u uslovima eliminacije obrazovane vode, u prisustvu katalitičke količine jedinjenja formule (VI): u kojoj R i R', isti ili različiti, svaki predstavlja linearnu ili razgranatu (C3-C10) alkil grupu, nesupstituisanu ili supstituisanu aril grupu, ili nesupstituisanu ili supstituisanu linearnu ili razgranatu (C1-C6) arilalkil grupu, kako bi se dobilo jedinjenje formule (I) nakon filtracije i ispiranja baznim rastvorom, jedinjenje formule (I) se izoluje u obliku čvrste mase posle rekristalizacije, uz razumevanje da se:-pod arilom podrazumeva fenil, naftil ili bifenil grupa,-izraz supstituisan odnosi na formule arila i arilalkila označavajući da aromatični deo ovih grupa može biti supstituisan sa 1 do 3 iste ili različite grupe, odabrane od linearnog ili razgranatog (C1-C6) alkila, hidroksi i linearnog ili razgranatog (C1-C6) alkoksi. Prijava sadrži još 7 zavisnih patentnih zahteva.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0401436A FR2866336B1 (fr) | 2004-02-13 | 2004-02-13 | Nouveau procede de synthese du (7-methoxy-3,4-dihydro-1-naphtalenyl) acetonitrile et application a la synthese de l'agomelatine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RS50545B true RS50545B (sr) | 2010-05-07 |
Family
ID=34685016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RSP-2008/0039A RS50545B (sr) | 2004-02-13 | 2005-02-11 | Novi postupak sinteze (7-metoksi-3,4-dihidro-1-naftalenil) acetonitrila i primena u sintezi agomelatina |
Country Status (33)
| Country | Link |
|---|---|
| US (1) | US7479569B2 (sr) |
| EP (1) | EP1564204B1 (sr) |
| JP (1) | JP4192155B2 (sr) |
| KR (1) | KR100682699B1 (sr) |
| CN (1) | CN1293048C (sr) |
| AR (1) | AR048235A1 (sr) |
| AT (1) | ATE382603T1 (sr) |
| AU (1) | AU2005200618B8 (sr) |
| BR (1) | BRPI0501093B1 (sr) |
| CA (1) | CA2495628C (sr) |
| CY (1) | CY1107156T1 (sr) |
| DE (1) | DE602005004044T2 (sr) |
| DK (1) | DK1564204T3 (sr) |
| EA (1) | EA007795B1 (sr) |
| ES (1) | ES2298964T3 (sr) |
| FR (1) | FR2866336B1 (sr) |
| GE (1) | GEP20063955B (sr) |
| HK (1) | HK1078565A1 (sr) |
| HR (1) | HRP20080134T3 (sr) |
| MA (1) | MA27515A1 (sr) |
| ME (1) | ME01401B (sr) |
| MX (1) | MXPA05001632A (sr) |
| MY (1) | MY143266A (sr) |
| NO (1) | NO333483B1 (sr) |
| NZ (1) | NZ538194A (sr) |
| PL (1) | PL1564204T3 (sr) |
| PT (1) | PT1564204E (sr) |
| RS (1) | RS50545B (sr) |
| SG (1) | SG114704A1 (sr) |
| SI (1) | SI1564204T1 (sr) |
| UA (1) | UA76649C2 (sr) |
| WO (1) | WO2005077888A1 (sr) |
| ZA (1) | ZA200501254B (sr) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| FR2889523B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline v de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2889522B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iv de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| FR2889521B1 (fr) * | 2005-08-03 | 2007-12-28 | Servier Lab | Nouvelle forme cristalline iii de l'agomelatine, son procede de preparation et les compositions pharmaceutiques qui la contiennent |
| WO2007079317A2 (en) * | 2005-12-06 | 2007-07-12 | Neurocrine Biosciences, Inc. | Use of sedative hypnotics for treating obesity or maintaining weight loss |
| 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 |
| CN102276492B (zh) | 2010-06-08 | 2013-04-10 | 上海医药工业研究院 | 阿戈美拉汀中间体及其制备方法 |
| EP2580183B1 (en) | 2010-06-10 | 2014-07-23 | Gador S.A. | New process for the preparation of n-[2-(7-methoxy-1-naphthyl)-ethyl]acetamide |
| CN102060733B (zh) * | 2010-12-06 | 2014-01-29 | 威海迪素制药有限公司 | (7-甲氧基-3,4-二氢-1-萘基)乙腈的制备方法 |
| WO2013054273A2 (en) | 2011-10-11 | 2013-04-18 | Ranbaxy Laboratories Limited | Process for the preparation of agomelatine |
| US20140336380A1 (en) | 2011-12-01 | 2014-11-13 | Ranbaxy Laboratories Limited | Process for the preparation of agomelatine |
| WO2014001939A1 (en) * | 2012-06-30 | 2014-01-03 | Alembic Pharmaceuticals Limited | Process for preparation of agomelatine and crystalline form i thereof |
| ITMI20121444A1 (it) | 2012-08-27 | 2014-02-28 | Procos Spa | Processo per la produzione di agomelatine |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US432702A (en) * | 1890-07-22 | Car-seat | ||
| US3931188A (en) * | 1974-05-06 | 1976-01-06 | Bristol-Myers Company | 3-Hydroxy-5,6-benzomorphinan derivatives |
| US3992403A (en) * | 1975-05-30 | 1976-11-16 | Schering Corporation | 2-Imidazolines and their use as hypoglycemic agents |
| 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. |
| 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 |
-
2004
- 2004-02-13 FR FR0401436A patent/FR2866336B1/fr not_active Expired - Fee Related
-
2005
- 2005-02-01 CA CA002495628A patent/CA2495628C/fr not_active Expired - Lifetime
- 2005-02-04 US US11/051,869 patent/US7479569B2/en active Active
- 2005-02-07 MY MYPI20050475A patent/MY143266A/en unknown
- 2005-02-07 SG SG200500678A patent/SG114704A1/en unknown
- 2005-02-10 MX MXPA05001632A patent/MXPA05001632A/es active IP Right Grant
- 2005-02-11 NZ NZ538194A patent/NZ538194A/en unknown
- 2005-02-11 DE DE602005004044T patent/DE602005004044T2/de not_active Expired - Lifetime
- 2005-02-11 PT PT05290309T patent/PT1564204E/pt unknown
- 2005-02-11 NO NO20050738A patent/NO333483B1/no unknown
- 2005-02-11 PL PL05290309T patent/PL1564204T3/pl unknown
- 2005-02-11 AR ARP050100499A patent/AR048235A1/es unknown
- 2005-02-11 DK DK05290309T patent/DK1564204T3/da active
- 2005-02-11 RS RSP-2008/0039A patent/RS50545B/sr unknown
- 2005-02-11 AT AT05290309T patent/ATE382603T1/de active
- 2005-02-11 WO PCT/FR2005/000324 patent/WO2005077888A1/fr active Application Filing
- 2005-02-11 SI SI200530155T patent/SI1564204T1/sl unknown
- 2005-02-11 ZA ZA2005/01254A patent/ZA200501254B/en unknown
- 2005-02-11 MA MA28098A patent/MA27515A1/fr unknown
- 2005-02-11 UA UAA200501279A patent/UA76649C2/uk unknown
- 2005-02-11 ME MEP-2008-946A patent/ME01401B/me unknown
- 2005-02-11 GE GEAP8622A patent/GEP20063955B/en unknown
- 2005-02-11 ES ES05290309T patent/ES2298964T3/es not_active Expired - Lifetime
- 2005-02-11 AU AU2005200618A patent/AU2005200618B8/en not_active Expired
- 2005-02-11 EP EP05290309A patent/EP1564204B1/fr not_active Expired - Lifetime
- 2005-02-12 KR KR1020050011750A patent/KR100682699B1/ko active Protection Beyond IP Right Term
- 2005-02-14 BR BRPI0501093-4A patent/BRPI0501093B1/pt active IP Right Grant
- 2005-02-14 JP JP2005035755A patent/JP4192155B2/ja not_active Expired - Lifetime
- 2005-02-14 EA EA200500202A patent/EA007795B1/ru unknown
- 2005-02-16 CN CNB2005100077521A patent/CN1293048C/zh not_active Expired - Lifetime
- 2005-11-21 HK HK05110486A patent/HK1078565A1/xx unknown
-
2008
- 2008-01-28 CY CY20081100095T patent/CY1107156T1/el unknown
- 2008-03-25 HR HR20080134T patent/HRP20080134T3/xx unknown
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