Patent ID: 6780968
Filing Date: 2004-08-24
Classification: A61K,A61P,C07K

Abstract:
A monocyclic compound having the formula (1): in which:X1, X2, X3, X4, which may be the same or different from one another, is selected from the group consisting of â€”CONRâ€”, â€”NRCOâ€”, â€”OCOâ€”, â€”COOâ€”, â€”CH2NRâ€” and â€”NRâ€”CH2â€”, where R is H or a C1-3 alkyl or benzyl; f, g, h, m, which may be the same or different from one another, may be 0 or 1; R1 and R2 which may be the same or different from one another, represent the side chain of a natural amino acid selected from the group consisting of tryptophan, phenylalanine, tyrosine and histidine, or the side chain of a non-natural amino acid selected from the group consisting of; tryptophan and phenylalanine, either mono- or di-substituted with residues selected from the group consisting of C1-3 alkyl or halo-alkyl, C1-3 alkoxyl or amino-alkoxyl, halogen, OH, NH2 and NR13R14, where R13 and R14, which may be the same or different from one another, represent a hydrogen or C1-3 alkyl group; R3 is selected from the group consisting of: linear or branched alkyl having the formula CnH2n+1 with n=1-5 (selected from the group consisting of methyl, ethyl, propyl, isopropyl, n-butyl and t-butyl) cycloalkyl or alkylcycloalkyl of formula CnH2nâˆ’1 with n=5-9 (selected from the group consisting of: cyclopentyl, cyclohexyl and methylcyclohexyl) (CH3)râ€”Ar1, where r=1 or 2 and where Ar1 is an aromatic group selected from the group consisting of: &agr;-naphthyl, &bgr;-naphthyl, phenyl, indole, said Ar1 group being possibly substituted with a maximum of two residues selected from the group consisting of: C1-3 alkyl, CF3, C1-3 alkoxyl, Cl, F, OH and NH2; R4 represents an L-Q group where: L is a chemical bond or CH2, and Q is selected from the group consisting of: OH, NH2, NR9R10, OR11, and where R9 and R10, which may be the same or different from one another, represent a hydrogen or C1-3alkyl group, C1-3hydroxy alkyl, C1-3dihydroxyaklyl, C1-3alkyl-CONHR12 (wherein R12 is a monoglycosidic group derived from D or L pentoses or hexoses (selected from the group consisting of ribose, arabinose, glucose, galactose, fructose, glucosamine, galactosamine N-acetylglucosamine and N-acetylgalactosamine)), C1-3alkyltetrazole, C1-3alkyl-COOH or wherein R9R10 are joined together to form with the N atom a morpholine or a piperidine ring and where R11 is a C1-3 alkyl chain, or a C2-4 amino-alkyl chain; NHCOR8 wherein R8 is a cyclohexane containing from 2 to 4 OH groups, C1-6 alkyl chain containing a polar group (chosen in the group consisting of NH2, COOH, CONHR12, (wherein R12 is as hereabove defined) or [1,4â€²]bipiperidine)) COOH, COOR17 or CONHR12, wherein R12 is as hereabove defined and R17 is as R17 or a group 4-nitrobenzyl R5, R6, R7 are H in which the carbon atom that carries the subtituents R3 and R7 has configuration R; wherein when R1&boxH;R2&boxH;a side chain of tryptophan and R4&boxH;CH2OH then R3 is not isopropyl.