Title:
チアゾロ[3,4,5-デ][4,1]ベンゾチアゼピン型生成物の作製方法。
Document Type and Number:
Japanese Patent JP2007519621
Kind Code:
A
Abstract:
Method for preparing 2-imino-9-trifluoromethyl-4,5-dihydro-2H,7H-thiazolo[3,4,5-de][4,1]benzothiazepine-6,6-dioxide methanesulfonate (10). Method for preparing 2-imino-9-trifluoromethyl-4,5-dihydro-2H,7H-thiazolo[3,4,5-de][4,1]benzothiazepine-6,6-dioxide methanesulfonate of formula (10) comprises: (a) protecting 4-trifluoromethylaniline by refluxing with di-tert-butyl-carbonate in monochlorobenzene; (b) converting the product to 2-hydroxymethyl-4-trifluoromethyl phenylcarbamate (12) without isolation of the intermediate 2-formyl compound; (c) reacting (12) with thioglycolic acid in presence of p-toluenesulfonic acid to form 7-trifluoromethyl-1,5-dihydro-3H-[4,1]benzothiazepin-2-one (6); (d) reducing (6) to 7-trifluoromethyl-1,2,3,5-tetrahydro[4,1]benzothiazepine (7); (e) reacting (7) with bromine and potassium thiocyanate in acetic acid to form 2-imino-9-trifluoromethyl-4,5-dihydro-2H,7H-thiazolo[3,4,5-de][4,1]benzothiazepine hydrobromide (8); and (f) oxidizing (8) to the free base form of (10) then treatment with methanesulfonic acid to give (10). [Image] Independent claims are also included for the following: (1) preparation of (6) by step (c); (2) preparation of the (S)-6-oxide of 2-imino-9-trifluoromethyl-4,5-dihydro-2H,7H-thiazolo[3,4,5-de][4,1]benzothiazepine; (3) preparation of (8) by steps (a)-(e); and (4) tert-butyl 2-hydroxymethyl-4-trifluoromethylphenyl carbamate (8); and 2-imino-9-trifluoromethyl-4,5-dihydro-2H,7H-thiazolo[3,4,5-de][4,1]benzothiazepin-6-oxide trifluoroacetate as new intermediates. ACTIVITY : Anticonvulsant; Vasotropic; Neuroprotective; Nootropic; Antiparkinsonian; Tranquilizer; Antidepressant; Neuroleptic; Analgesic; Antiinflammatory; Anorectic; Antimigraine; Antiemetic. No details of tests for these activities are given. MECHANISM OF ACTION : None given.
Inventors:
Miutei, Stephane
Marpearl, Joel
Rabiniyu, Michel
Schiebe, Michel
Marpearl, Joel
Rabiniyu, Michel
Schiebe, Michel
Application Number:
JP2006543580A
Publication Date:
July 19, 2007
Filing Date:
December 07, 2004
Export Citation:
Assignee:
Avantes Furuma S.A.
International Classes:
C07D513/06; A61P9/00; A61P9/10; A61P25/04; A61P25/08; A61P25/16; A61P25/28; B01J31/02; C07C269/04; C07C269/06; C07C271/28; C07D281/10; C07D513/04; A61K31/554; C07B61/00
Domestic Patent References:
| JPH08259447A | 1996-10-08 | |||
| JPH07179429A | 1995-07-18 | |||
| JP2002520253A | 2002-07-09 |
Attorney, Agent or Firm:
Yoshio Kawaguchi
Makoto Ono
Chihiro Watanabe
Kenkyo Kanayama
Katsuma Osaki
Mitsuaki Tsubokura
Makoto Ono
Chihiro Watanabe
Kenkyo Kanayama
Katsuma Osaki
Mitsuaki Tsubokura