Patent ID: 6683154
Filing Date: 2004-01-27
Classification: C07B,C07C

Abstract:
A pharmaceutical composition comprising an antimicrobial-effective amount of a &bgr;-amino acid oligomer or polymer wherein each residue of the oligomer or polymer is a &bgr;-amino acid residue comprising formula: wherein p is an integer greater than 6; wherein X is independently selected from the group consisting of hydrogen, linear or branched C1-C6-alkyl, alkenyl, or alkynyl; mono- or bicyclic aryl, mono- or bicyclic heteroaryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, mono- or bicyclic heteroaryl-C1-C6-alkyl, â€”(CH2)n+1â€”OR, â€”(CH)n+1â€”SR, â€”(CH2)n+1â€”S(&boxH;O)â€”CH2â€”R, â€”(CH2)n+1â€”S(&boxH;O)2â€”CH2â€”R, â€”(CH2)n+1â€”NRR, â€”(CH2)n+1â€”NHC(&boxH;O)R, â€”(CH2)n+1â€”NHS(&boxH;O)2â€”CH2â€”R, â€”(CH2)n+1â€”Oâ€”(CH2)mâ€”R1, â€”(CH2)n+1â€”Sâ€”(CH2)mâ€”R1, â€”(CH2)n+1â€”S(&boxH;O)â€”(CH2)mâ€”R1, â€”(CH2)n+1â€”S(&boxH;O)2â€”(CH2)mâ€”R1, â€”(CH2)n+1â€”NHâ€”(CH2)mâ€”R1, â€”(CH2)n+1â€”Nâ€”{(CH2)mâ€”R1}2, â€”(CH2)n+1â€”NHC(&boxH;O)â€”(CH2)n+1â€”R1, and â€”(CH2)n+1â€”NHS(&boxH;O)2â€”(CH2)mâ€”R1; wherein R is independently selected from the group consisting of hydrogen, C1-C6-alkyl, alkenyl, or alkynyl; mono- or bicyclic aryl, mono- or bicyclic heteraryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, mono- or bicyclic heteroaryl-C1-C6-alkyl; and wherein R1 is independently selected from the group consisting of hydroxy, C1-C6-alkyloxy, aryloxy, heteroaryloxy, thio, C1-C6-alkylthio, C1-C6-alkylsulfinyl, C1-C6-alkylsulfonyl, arylthio, arylsulfinyl, arylsulfonyl, heteroarylthio, heteroarylsulfinyl, heteroarylsulfonyl, amino, mono- or di-C1-C6-alkylamino, mono- or diarylamino, mono- or diheteroarylamino, N-alkyl-N-arylamino, N-alkyl-N-heteroarylamino, N-aryl-N-heteroarylamino, aryl-C1-C6-alkylamino, carboxylic acid, carboxamide, mono- or di-C1-C6-alkylcarboxamide, mono- or diarylcarboxamide, mono- or diheteroarylcarboxamide, N-alkyl-N-arylcarboxamide, N-alkyl-N-heteroarylcarboxamide, N-aryl-N-heteroarylcarboxamide, sulfonic acid, sulfonamide, mono- or di-C1-C6-alkylsulfonamide, mono- or diarylsulfonamide, mono- or diheteroarylsulfonamide, N-alkyl-N-arylsulfonamide, N-alkyl-N-heteroarylsulfonamide, N-aryl-N-heteroarylsulfonamide, urea; mono- di- or tri-substituted urea, wherein the subsitutent(s) is selected from the group consisting of C1-C6-alkyl, aryl, heteroaryl; O-alkylurethane, O-arylurethane, and O-heteroarylurethane; wherein Y is independently selected from the group consisting of hydrogen, linear or branched C1-C6-alkyl, alkenyl, or alkynyl; mono- or bicyclic aryl, mono- or bicyclic heteroaryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, mono- or bicyclic heteroaryl-C1-C6-alkyl, â€”(CH2)nâ€”OR, â€”(CH2)nâ€”SR, â€”(CH2)nâ€”S(&boxH;O)â€”CH2â€”R, â€”(CH2)nâ€”S(&boxH;O)2â€”CH2â€”R, â€”(CH2)nâ€”NRR, â€”(CH2)nâ€”NHC(&boxH;O)R, â€”(CH2)nâ€”NHS(&boxH;O)2â€”CH2â€”R, â€”(CH2)nâ€”Oâ€”(CH2)mâ€”R1, â€”(CH2)nâ€”Sâ€”(CH2)mâ€”R1, â€”(CH2)nâ€”S(&boxH;O)â€”(CH2)mâ€”R1, â€”(CH2)nâ€”S(&boxH;O)2â€”(CH2)mâ€”R1, â€”(CH2)nâ€”NHâ€”(CH2)mâ€”R1, â€”(CH2)nâ€”Nâ€”{(CH2)mâ€”R1}2â€”(CH2)nâ€”NHC(&boxH;O)â€”(CH2)mâ€”R1, and â€”(CH2)nâ€”NHS(&boxH;O)2â€”(CH2)mâ€”R1; wherein R and R1 are as defined hereinabove; or X and Y combined, together with the carbon atoms to which they are bonded, independently define a substituted or unsubstituted C3-C8 cycloalkyl, cycloalkenyl or heterocyclic ring having one or more N, O or S atom(s) as the heteroatom(s); the substituents on carbon atoms of the rings being independently selected from the group consisting of linear or branched C1-C6-alkyl, alkenyl, alkynyl; mono- or bicyclic aryl, mono- or bicyclic heteraryl having up to 5 heteroatoms selected from N, O, and S; mono- or bicyclic aryl-C1-C6-alkyl, mono- or bicyclic heteroaryl-C1-C6-alkyl, and the substituents listed above for X and Y when X and Y are not combined; the substituents on nitrogen heteroatoms of the rings being independently selected from the group consisting of â€”S(&boxH;O)2â€”CH2â€”R, â€”C(&boxH;O)â€”R, â€”S(&boxH;O)2â€”(CH2)mâ€”R1, â€”C(&boxH;O)â€”(CH2)n+1â€”R1; wherein R and R1 are as defined hereinabove; m is an integer of from 2-6 and n is an integer of from 0-6; W is hydrogen or an amino-terminal capping group; Z is hydroxy or a carboxy-terminal capping group; and further wherein in at least one residue, X and Y are combined in a cyclic moiety; and pharmaceutically-suitable salts thereof; in combination with a pharmaceutically-suitable carrier.