Global Patent Index - EP 1235792 A1

EP 1235792 A1 2002-09-04 - 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

EP 1235792 A1 (EN)

Application

EP 99974268 A

Priority

US 9915380 W

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 (main, further and additional classification)

C07C 261/00; C07C 229/04; C07C 229/22; C07D 281/02

IPC 8 full level (invention and additional information)

C07D 513/04 (2006.01); 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); C07C 319/22 (2006.01); C07C 323/59 (2006.01); C07D 281/02 (2006.01)

CPC (invention and additional information)

Y02P 20/55 (2015.11)

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

EP 1235792 A1 20020904; EP 1235792 A4 20030625; HU 0202462 A2 20021128; HU 0202462 A3 20050128; JP 2004514665 A 20040520; KR 20020067490 A 20020822