EA199900906A1 - Новый способ получения (+/-)3-(3,4-дихлорфенил)-2-диметиламино-2-метилпропан-1-ола или церикламина (inn) - Google Patents
Новый способ получения (+/-)3-(3,4-дихлорфенил)-2-диметиламино-2-метилпропан-1-ола или церикламина (inn)Info
- Publication number
- EA199900906A1 EA199900906A1 EA199900906A EA199900906A EA199900906A1 EA 199900906 A1 EA199900906 A1 EA 199900906A1 EA 199900906 A EA199900906 A EA 199900906A EA 199900906 A EA199900906 A EA 199900906A EA 199900906 A1 EA199900906 A1 EA 199900906A1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- dichlorophenyl
- cericlamine
- ola
- methylpropan
- dimethylamine
- Prior art date
Links
- -1 3,4-DICHLOROPHENYL Chemical class 0.000 title abstract 3
- FWYRGHMKHZXXQX-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-(dimethylamino)-2-methylpropan-1-ol Chemical compound CN(C)C(C)(CO)CC1=CC=C(Cl)C(Cl)=C1 FWYRGHMKHZXXQX-UHFFFAOYSA-N 0.000 title abstract 3
- 229950000303 cericlamine Drugs 0.000 title abstract 2
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 abstract 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- IHMZSAUTKBMJPH-UHFFFAOYSA-N 2-chloro-3-(3,4-dichlorophenyl)-2-methylpropanoic acid Chemical compound OC(=O)C(Cl)(C)CC1=CC=C(Cl)C(Cl)=C1 IHMZSAUTKBMJPH-UHFFFAOYSA-N 0.000 abstract 1
- SDYWXFYBZPNOFX-UHFFFAOYSA-N 3,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C(Cl)=C1 SDYWXFYBZPNOFX-UHFFFAOYSA-N 0.000 abstract 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 abstract 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001413 amino acids Chemical class 0.000 abstract 1
- 238000006254 arylation reaction Methods 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052987 metal hydride Inorganic materials 0.000 abstract 1
- 150000004681 metal hydrides Chemical class 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
-
- 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
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/58—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (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)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Способ изготовления церикламина, включающий: i) арилирование метакриловой кислоты хлоридом диазония 3,4-дихлоранилина, с получением (+/-)2-хлор-3-(3,4-дихлорфенил)-2-метилпропионовой кислоты, ii) аминирование кислоты диметиламином с получением (+/-)3-(3,4-дихлорфенил)-2-диметиламин-2-метилпропионовой кислоты или ее соли щелочного металла, iii) этерификацию аминокислоты или ее соли, затем iv) восстановление эфира металлогидридом или органометаллогидридом с получением (+/-)3-(3,4-дихлорфенил)-2- диметиламин-2 метилпропан-1-ола.Международная заявка была опубликована вместе с отчетом о международном поиске.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9704311A FR2761686B1 (fr) | 1997-04-07 | 1997-04-07 | Nouveau procede de preparation du (+/-)3-(3,4- dichlorophenyl)-2-dimethylamino-2-methyl-propan-1-ol ou cericlamine (inn) |
PCT/EP1998/002213 WO1998045248A1 (en) | 1997-04-07 | 1998-04-06 | Novel process for the preparation of (+/-)3- (3,4-dichlorophenyl)-2- dimethylamino-2-methylpropan-1-ol or cericlamine (inn) |
Publications (2)
Publication Number | Publication Date |
---|---|
EA199900906A1 true EA199900906A1 (ru) | 2000-08-28 |
EA004399B1 EA004399B1 (ru) | 2004-04-29 |
Family
ID=9505666
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EA199900906A EA004399B1 (ru) | 1997-04-07 | 1998-04-06 | Способ получения (+/-)3-(3,4-дихлорфенил)-2-диметиламино-2-метилпропан-1-ола или церикламина (inn) |
Country Status (21)
Country | Link |
---|---|
US (1) | US6121491A (ru) |
EP (1) | EP0973724B1 (ru) |
JP (1) | JP2001519799A (ru) |
KR (1) | KR20010006073A (ru) |
AT (1) | ATE251116T1 (ru) |
AU (1) | AU728636B2 (ru) |
BR (1) | BR9811459A (ru) |
CA (1) | CA2277874A1 (ru) |
DE (1) | DE69818653T2 (ru) |
DK (1) | DK0973724T3 (ru) |
EA (1) | EA004399B1 (ru) |
ES (1) | ES2209137T3 (ru) |
FR (1) | FR2761686B1 (ru) |
HU (1) | HUP0001753A3 (ru) |
IL (1) | IL130813A (ru) |
NZ (1) | NZ337588A (ru) |
PL (1) | PL336041A1 (ru) |
PT (1) | PT973724E (ru) |
SK (1) | SK284184B6 (ru) |
WO (1) | WO1998045248A1 (ru) |
ZA (1) | ZA982927B (ru) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
PL1691811T3 (pl) | 2003-12-11 | 2014-12-31 | Sunovion Pharmaceuticals Inc | Skojarzenie leku uspokajającego i modulatora neuroprzekaźnikowego oraz sposoby poprawy jakości snu i leczenia depresji |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2378746A1 (fr) * | 1977-01-28 | 1978-08-25 | Synthelabo | Derives d'acides a-amines |
JPS6078921A (ja) * | 1983-10-05 | 1985-05-04 | Toyo Soda Mfg Co Ltd | ハロゲン含有エチルベンゼン誘導体の製造方法 |
JPS61204150A (ja) * | 1985-03-08 | 1986-09-10 | Sagami Chem Res Center | α―ハロ―α―トリフルオロメチル―β―アリールプロピオン酸 |
FR2593499B1 (fr) * | 1986-01-30 | 1988-08-12 | Jouveinal Sa | Aminoalcools, leur procede de preparation et leurs applications, notamment en therapeutique |
FR2690916B1 (fr) * | 1992-05-05 | 1994-06-17 | Jouveinal Inst Rech | Nouveaux enantiomeres derives du (s)-amino-2-(dichloro-3,4-benzyl)-2-propanol-1. |
US5472970A (en) * | 1992-05-05 | 1995-12-05 | Institut De Recherche Jouveinal S.A. | Allylaminoesters and their application in therapeutics |
-
1997
- 1997-04-07 FR FR9704311A patent/FR2761686B1/fr not_active Expired - Fee Related
-
1998
- 1998-04-06 JP JP54241598A patent/JP2001519799A/ja active Pending
- 1998-04-06 US US09/381,118 patent/US6121491A/en not_active Expired - Fee Related
- 1998-04-06 IL IL13081398A patent/IL130813A/xx active IP Right Grant
- 1998-04-06 ZA ZA9802927A patent/ZA982927B/xx unknown
- 1998-04-06 PL PL98336041A patent/PL336041A1/xx unknown
- 1998-04-06 ES ES98922719T patent/ES2209137T3/es not_active Expired - Lifetime
- 1998-04-06 EP EP98922719A patent/EP0973724B1/en not_active Expired - Lifetime
- 1998-04-06 AT AT98922719T patent/ATE251116T1/de not_active IP Right Cessation
- 1998-04-06 DE DE69818653T patent/DE69818653T2/de not_active Expired - Fee Related
- 1998-04-06 KR KR1019997009151A patent/KR20010006073A/ko not_active Ceased
- 1998-04-06 BR BR9811459-0A patent/BR9811459A/pt not_active IP Right Cessation
- 1998-04-06 CA CA002277874A patent/CA2277874A1/en not_active Abandoned
- 1998-04-06 WO PCT/EP1998/002213 patent/WO1998045248A1/en not_active Application Discontinuation
- 1998-04-06 AU AU75259/98A patent/AU728636B2/en not_active Ceased
- 1998-04-06 SK SK1360-99A patent/SK284184B6/sk unknown
- 1998-04-06 EA EA199900906A patent/EA004399B1/ru not_active IP Right Cessation
- 1998-04-06 NZ NZ337588A patent/NZ337588A/xx unknown
- 1998-04-06 DK DK98922719T patent/DK0973724T3/da active
- 1998-04-06 HU HU0001753A patent/HUP0001753A3/hu unknown
- 1998-04-06 PT PT98922719T patent/PT973724E/pt unknown
Also Published As
Publication number | Publication date |
---|---|
KR20010006073A (ko) | 2001-01-15 |
EA004399B1 (ru) | 2004-04-29 |
AU728636B2 (en) | 2001-01-11 |
DK0973724T3 (da) | 2004-02-02 |
IL130813A0 (en) | 2001-01-28 |
ZA982927B (en) | 1999-07-15 |
JP2001519799A (ja) | 2001-10-23 |
DE69818653T2 (de) | 2004-08-19 |
SK136099A3 (en) | 2000-05-16 |
US6121491A (en) | 2000-09-19 |
PT973724E (pt) | 2004-02-27 |
ES2209137T3 (es) | 2004-06-16 |
EP0973724B1 (en) | 2003-10-01 |
BR9811459A (pt) | 2000-09-19 |
FR2761686A1 (fr) | 1998-10-09 |
DE69818653D1 (de) | 2003-11-06 |
HUP0001753A2 (hu) | 2000-11-28 |
PL336041A1 (en) | 2000-06-05 |
ATE251116T1 (de) | 2003-10-15 |
AU7525998A (en) | 1998-10-30 |
SK284184B6 (sk) | 2004-10-05 |
FR2761686B1 (fr) | 1999-05-14 |
IL130813A (en) | 2003-07-06 |
EP0973724A1 (en) | 2000-01-26 |
HUP0001753A3 (en) | 2000-12-28 |
WO1998045248A1 (en) | 1998-10-15 |
CA2277874A1 (en) | 1998-10-15 |
NZ337588A (en) | 2000-05-26 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM4A | Lapse of a eurasian patent due to non-payment of renewal fees within the time limit in the following designated state(s) |
Designated state(s): AM AZ BY KZ KG MD TJ TM RU |