METHODS FOR MAKING VALERENIC ACID DERIVATIVES AND THEIR USE

摘要

The present invention is directed to compounds, intermediates and methods for making valerenic acid and its derivatives as well as the use of such compounds as GABAA receptor ligands.

主权项

1. A compound of formula (I): wherein the dotted line between C10 and C11 represents an optional double bond; D is selected from the group of 5-membered rings consisting of the following structures: R1 is selected from the group consisting of substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —(C0-C10)C(O)R10, —(C0-C10)C(O)OR10, —(C0-C10)OC(O)R10, —(C1-C10)SR10, —(C0-C10)C(O)NR11R12, —(C0-C10)C(O)NHN11R12 and —(C1-C10)OR10;
wherein R10, R11 and R12 independently from each other are selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8 cycloalkenyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; R2, R3, R4, R7, R8 and R9 independently from each other are selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8 cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —CN, —(C1-C10)OH, —NR11R12, —(C0-C10)C(O)R10, —(C0-C10)C(O)OR10, —(C0-C10)OC(O)R10, —(C1-C10)SR10, —(C0-C10)C(O)NR11R12, —C(O)NHNR11R12 and —(C0-C10)OR10;
wherein R10, R11 and R12 independently from each other are selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8 cycloalkenyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; R5 is selected from the group consisting of O and CHR13;
wherein R13 is selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8 cycloalkenyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl; R6 is selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8 cycloalkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, —CN, —(C1-C10)OH, —NR11R12, —(C0-C10)C(O)R10, —(C0-C10)C(O)OR10, —(C1-C10)OC(O)R10, —(C1-C10)SR10, —(C0-C10)C(O)NR11R12, —C(O)NHN11R12, —(C1-C10)OR10, —OR14 and —OC(O)R14;
wherein R10, R11, R12 and R14 independently from each other are selected from the group consisting of H, substituted or unsubstituted C1-C10 alkyl, substituted or unsubstituted C3-C8 cycloalkyl, substituted or unsubstituted C2-C10 alkenyl, substituted or unsubstituted C4-C8 cycloalkenyl, substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl;or a pharmaceutically salt thereof or solvate thereof;excluding the following compounds: