Therapeutic compounds
The invention provides compounds having the general formula I: and pharmaceutically acceptable salts thereof, wherein the variables R 1 , R 2 , R 3 , R 4 , subscipt m and n, have the meaning as described herein, and compositions containing such compounds and methods for using such compounds and compositions.
1. A compound of formula I:
or a pharmaceutically acceptable salt thereof, wherein:
R 1 is C 12-20 alkyl, C 12-20 alkenyl or C 12-20 alkynyl, and wherein the C 12-20 alkyl, C 12-20 alkenyl and C 12-20 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR a , —SR a , —NR a R b , oxo, —NO 2 and —CN;
R 2 is methyl
each R 3 is independently selected from the group consisting of —F, —Cl, —Br, —I, —OH, —OR a , —SR a , —NR a R b , —CN, C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl, and wherein the C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR a , —SR a , —NR a R b , oxo, —NO 2 and —CN;
each R a is independently selected from the group consisting of —F, —C 1 , —Br, —I, —OR a , —SR a , —NR a R b , —NO 2 , —CN, C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl, and wherein the C 1-4 alkyl, C 2-4 alkenyl and C 2-4 alkynyl are optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR, —SR a , —NR a R b , oxo, —NO 2 and —CN;
each R 3 is independently hydrogen or C 1-4 alkyl;
each R b is independently hydrogen or C 1-4 alkyl;
the subscript m is 0, 1, 2 or 3; and
the subscript n is 0, 1, 2, or 3.
2. The compound of claim 1 that is a compound of formula Ia:
or a pharmaceutically acceptable salt thereof.
3. The compound of claim 1 , wherein R 1 is n-pentadecyl.
4. The compound of claim 1 , that is selected from the group consisting of:
or a pharmaceutically acceptable salt thereof.
5. A pharmaceutical composition comprising a compound of formula (I) as described in claim 1 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
6. A method to prepare a compound of formula I or a pharmaceutically acceptable salt thereof, as described in claim 1 , comprising converting a corresponding compound of formula II or a salt thereof to the compound of formula I or the pharmaceutically acceptable salt thereof:
wherein:
R 5 is C 1-10 alkyl that is optionally substituted with one or more groups independently, selected from —F, —Cl, —Br, —I, —OR a , —SR a , oxo, —NO 2 and —CN; and
R 6 is hydrogen or C 1-6 alkyl that is optionally substituted with one or more groups independently selected from —F, —Cl, —Br, —I, —OR a , —SR a , —NR a R b , oxo, —NO 2 and —CN.
7. A pharmaceutical composition comprising the compound of claim 4 , or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.