The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Nov. 24, 1998
Filed:
Apr. 18, 1995
Herman Van Belle, Beerse, BE;
Willy Joannes Van Laerhoven, Beerse, BE;
Janssen Pharmaceutica, N.V., Beerse, BE;
Abstract
There is disclosed a process for preparing (l)-(-)-2-aminocarbonyl)-N-(4-amino-2,6-dichlorophenyl)-4-�5,5-bis(4-fluor ophenyl)pentyl!-1-piperazineacetamide which comprises the steps of (a) cyclizing (-)-(S,S)-N.sup.1,N.sup.2 -bis(1-phenylethyl)-1,2-ethanediamine with 2,3-dibromopropanamide in a reaction-inert solvent in the presence of a base, thus yielding an intermediate; (b) resolving the intermediate of into two stereoisomers and recovering thereby �1(S),2A,4(S)!-1,4-bis(1-phenylethyl)-2-piperazinecarboxamide; (c) hydrogenolyzing �1(S),2A,4(S)!-1,4-bis(1-phenylethyl)-2-piperazinecarboxamide under a hydrogen atmosphere in an alkanol in the presence of a hydrogenation catalyst to produce (+) -2-piperazinecarboxamide; (d) reductively N-alkylating (+)-2-piperazinecarboxamide with 5,5-bis(4-fluorophenyl)pentaldehyde under a hydrogen atmosphere in an alkanol in the presence of a hydrogenation catalyst to produce a compound of the formula: ##STR1## (e) N-alkylating the compound of Formula (VII) with an alkylating reagent of the formula: ##STR2## wherein W represents a reactive leaving group, in a reaction-inert solvent in the presence of a base to form the nitro analog of the desired compound; and (f) reducing the nitro compound in the presence of a reducing agent in a reaction-inert solvent.