Patent ID: 6495693
Filing Date: 2002-12-17
Classification: A61K,C07C,C07D

Abstract:
A pharmaceutical composition comprising a pharmaceutically inert carrier and a pharmaceutically effective amount of a compound of formula I: wherein:R1 is selected from the group consisting of (a) phenyl, (b) a substituted phenyl group of formula II: wherein Rc is selected from the group consisting of acyl, alkyl, alkoxy, alkylalkoxy, azido, cyano, halo, hydrogen, nitro, trihalomethyl, thioalkoxy, and wherein Rb and Rc are fused to form a heteroaryl or heterocyclic ring with the phenyl ring, Rb and Rbâ€² are independently selected from the group consisting of hydrogen, halo, nitro, cyano, trihalomethyl, alkoxy, and thioalkoxy with the proviso that when Rc is hydrogen, then Rb and Rbâ€² are either both hydrogen or both substituents other than hydrogen, (c) 2-naphthyl, (d) 2-naphthyl substituted at the 4, 5, 6, 7 and/or 8 positions with 1 to 5 substituents selected from the group consisting of alkyl, alkoxy, halo, cyano, nitro, trihalomethyl, thioalkoxy, aryl, and heteroaryl, (e) heteroaryl, and (f) substituted heteroaryl containing 1 to 3 substituents selected from the group consisting of alkyl, alkoxy, aryl, aryloxy, cyano, halo, nitro, heteroaryl, thioalkoxy and thioaryloxy provided that said substituents are not ortho to the heteroaryl attachment to the â€”NH group; R2 is selected from the group consisting of hydrogen, alkyl of from 1 to 4 carbon atoms, alkylalkoxy of from 1 to 4 carbon atoms, alkylthioalkoxy of from 1 to 4 carbon atoms, aryl, heteroaryl, substituted aryl and substituted heteroaryl provided that the substituents are not ortho to the attachment of the aryl or heteroaryl atom to the carbon atom; R3 is selected from the group consisting of alkyl, alkenyl, alkynyl, aryl, cycloalkyl, cycloalkenyl, heteroaryl, substituted alkyl, substituted alkenyl, substituted alkynyl, and heterocyclic; X is â€”C(O)Y where Y is selected from the group consisting of (a) alkyl, (b) substituted alkyl with the proviso that the substitution on said substituted alkyl does not include &agr;-haloalkyl, &agr;-diazoalkyl or &agr;-OC(O)alkyl groups, (c) alkoxy or thioalkoxy, (d) substituted alkoxy or substituted thioalkoxy, (e) hydroxy, (f) aryl, (g) heteroaryl, (h) heterocyclic, (i) â€”NRâ€²Râ€³ where Râ€² and Râ€³ are independently selected from the group consisting of: hydrogen, alkyl, substituted alkyl of from 1 to 10 carbon atoms, having from 1 to 3 substituents selected from the group consisting of alkoxy, substituted alkoxy, acyl, acylamino, acyloxy, amino, aminoacyl, aminoacyloxy, cyano, halogen, carboxyl, carboxylalkyl, cycloalkyl, oxyacylamino, thiol, thioalkoxy, substituted thioalkoxy, aryl, heteroaryl, heterocyclic, nitro, and mono- and di-alkylamino, mono- and di(substituted alkyl)amino, mono- and di-cycloalkylamino, mono- and di-arylamino, mono- and di-heteroaryl-amino, mono- and di-heterocyclic amino, and unsymmetric di-substituted amines having different substituents selected from alkyl, substituted alkyl, cycloalkyl, aryl, heteroaryl and heterocyclic, cycloalkyl, aryl, heteroaryl, heterocyclic, and where Râ€² and Râ€³ are joined to form a cyclic group having from 2 to 8 carbon atoms optionally containing 1 to 2 additional heteroatoms selected from the group consisting of oxygen, sulfer and nitrogen and optionally substituted with one or more alkyl or alkoxy groups, and when R3 contains at least 3 carbon atoms, X can also be â€”CR4R4Yâ€² WHERE each R4 is independently selected from the group consisting of hydrogen, alkyl, cycloalkyl, aryl, heteroaryl and heterocyclic and Yâ€² is selected from the group consisting of amino, thiol, â€”OC(O)R5, â€”SSR5, â€”SSC(O)R5 where R5 is selected from the group consisting of alkyl, substituted alkyl, cycloalkyl, aryl, heteroaryl and heterocyclic, and with the proviso that when R1 is 3,4-dichlorophenyl, R2 is methyl, and R3 is benzyl derived from D-phenylalanine, then X is not â€”C(O)OCH3.