Difluoro-pentapeptide derivative anti-inflammatory agents

C - Chemistry – Metallurgy – 07 – K

Patent

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Details

C07K 5/06 (2006.01) A61K 38/05 (2006.01) C07K 7/02 (2006.01) A61K 38/00 (2006.01)

Patent

CA 2152267

The subject invention involves anti-inflammatory compounds having structure (I), wherein: (a) -X is cyclic alkyl, having from 4 to 15 carbon atoms; branched alkyl, having from 6 to 15 carbon atoms; or aryl having from 6 to 15 carbon atoms; (b) n is an integer from 0 to 2; (c) -V- is -OC(O-, - N(Q)C(O)-, -N(Q)C(S)-, -C(O)-, -SO2- or -P(O)(OH)-; (d) -Q is hydrogen; or straight or branched chain alkyl, saturated or unsaturated with 1 or 2 double bonds, having from 1 to 6 carbon atoms; or -Q and -X are covalently linked forming a cyclic moiety which includes the nitrogen to which -Q is bonded and from 5 to 20 carbon atoms; (e) Z as -O- or -NH-; when V is -OC(O)-, -Z- is -NH-; (f) -R1 is a hydrophobic moiety; (g) -R2 is a hydrophobic moiety; (h) -R3 is -(CH2)m-A-NH2 or -(CH2)m-A-B-C(NH2)~NH wherein m is an integer from 1 to about 6, -A- is a covalent bond or p-phenyl or p-cyclohexyl, and -B- is a covalent bond or -NH-; (i) -R4 is a hydrophobic moiety; (j) -R5 is -(CH2)m-A-NH2 or -(CH2)m-A-B-C(NH2) =NH wherein m is an integer from 1 to about 6, -A is a covalent bond or p- phenyl or p-cyclohexyl, and -B- is a covalent bond or -NH-; and (k) -Y is hydrogen or methyl. The subject invention also involves pharmaceutical compositions comprising the above compounds, and methods for treating inflammation or pain using such compounds and compositions.

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