EP 1235792 A1 20020904 - PREPARATION OF ¬4S-(4ALPHA,7ALPHA,10ABETA) -4-AMINO-OCTAHYDRO-5-OXO-7H-PYRIDO 2,1-B 1,3 THIAZEPINE-7-CARBOXYLIC ACID, METHYL ESTER AND SALTS THEREOF VIA NOVEL DISULFIDES
Title (en)
PREPARATION OF ¬4S-(4ALPHA,7ALPHA,10ABETA) -4-AMINO-OCTAHYDRO-5-OXO-7H-PYRIDO 2,1-B 1,3 THIAZEPINE-7-CARBOXYLIC ACID, METHYL ESTER AND SALTS THEREOF VIA NOVEL DISULFIDES
Title (de)
HERSTELLUNG VON 4S-(4-g(a),7-g(a),10A-g(b)) -4-AMINO-OCTAHYDRO-5-OXO-7H-PYRIDO 2,1-B 1,3 THIAZEPIN-7-CARBONSÄURE METHYLESTER UND SEINER SALZE VIA NEUE DISULFIDE
Title (fr)
PREPARATION DE L'ESTER METHYLIQUE DE L'ACIDE ¬4S-(4ALPHA,7ALPHA,10ABETA) -4-AMINO-OCTAHYDRO-5-OXO-7H-PYRIDO 2,1-B 1,3 THIAZEPINE-7-CARBOXYLIQUE, ET DE SES SELS VIA DE NOUVEAUX DISULFURES
Publication
Application
Priority
US 9915380 W 19990729
Abstract (en)
[origin: HU0202462A2] Protected N,N'-L-homocystinediyl-bis(6,6-dimethoxy-L-norleucine methyl ester) derivatives (I) are new. The protected N,N'-L-homocystinediyl-bis(6,6-dimethoxy-L-norleucine methyl ester) derivatives are of formula (I). [Image] P1a protecting group. Independent claims are also included for: (1) protected L-homocystine bis(6,6-dimethoxy-L-norleucine methyl ester) disalts of formula (II). (2) a process for preparing (I); (3) a process for preparing protected methyl [4S-(4alpha ,7alpha ,10abeta )]-4-amino-octahydro-5-oxo- 7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate derivatives of formula (III), comprising reacting (I) with a reagent that cleaves the disulfide bond and subjecting the product to acid-catalyzed cyclization: (4) a process for preparing methyl [4S-(4alpha ,7alpha ,10abeta )]-4-amino-octahydro-5-oxo- 7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylate (IV) comprising preparing (III) by process (3) and removing the protecting group; (5) a process for preparing [4S-(4alpha (R*),7alpha ,10abeta )]-octahydro-4-(2-mercapto-1-oxo -3-phenylpropylamino)-5- oxo-7H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid (V), comprising: (a) preparing (IV) by process (4); (b) coupling (IV) with a 2-acylthio-3-phenylpropionic acid of formula (VI); and (c) treating the product of formula (VII) to remove the acyl group and convert the methyl ester group to a carboxylic acid group. [Image] [Image] [Image] [Image].
IPC 1-7
IPC 8 full level
C07B 53/00 (2006.01); C07B 61/00 (2006.01); C07C 229/04 (2006.01); C07C 229/22 (2006.01); C07C 261/00 (2006.01); C07D 513/04 (2006.01); C07C 319/22 (2006.01); C07C 323/59 (2006.01); C07D 281/02 (2006.01)
CPC (source: EP KR)
C07C 319/22 (2013.01 - KR); C07C 323/25 (2013.01 - KR); Y02P 20/55 (2015.11 - EP)
Designated contracting state (EPC)
AT BE CH CY DE DK ES FI FR GB GR IE IT LI LU MC NL PT SE
DOCDB simple family (publication)
EP 1235792 A1 20020904; EP 1235792 A4 20030625; HK 1048802 A1 20030417; HU P0202462 A2 20021128; HU P0202462 A3 20050128; JP 2004514665 A 20040520; KR 20020067490 A 20020822
DOCDB simple family (application)
EP 99974268 A 19990729; HK 03100856 A 20030206; HU P0202462 A 19990729; JP 2002544394 A 19990729; KR 20027001165 A 20020128