Compounds, pharmaceutical compositions containing same, and methods of use for same
View Patent ↗A pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula IV wherein R 21 =H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, —CH 2 OR 25 , —C(O)R 25 , —CO(O)R 25 , —C(O)NR 25 R 26 , —CH 2 C(O)R 25 , or —CH 2 C(O)NHR 25 , where R 25 and R 26 are each independently H, C 1 -C 10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, optionally containing one or more halogen atoms. R 22 =—OH, —OR 27 , —OCH 2 C(O)R 27 , —OCH 2 C(O)NHR 27 , —OC(O)R 27 , —OC(O)OR 27 , —OC(O)NHNH—R 5 , or —OC(O)NR 27 R 28 , where R 27 and R 28 are each independently H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, and where R 27 and R 28 can each optionally contain halogen atoms; R 23 and R 24 , the same or different from each other, are C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl. Methods of using such formulations for the treatment of cancer, to effect weight loss, to treat microbially-based infections, to inhibit neuropeptide-Y and/or fatty acid synthase, and to stimulate CPT-1.
1. A compound of formula I:
wherein:
R 1 =H
R 2 =—OH, —OR 5 , —OCH 2 C(O)R 5 , —OCH 2 C(O)NHR 5 , —OC(O)R 5 , —OC(O)OR 5 , —OC(O)NHNH—R 5 , or —OC(O)NR 5 R 6 , where R 5 and R 6 are each independently H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, or alkylaryl, and where R 5 and R 6 can each optionally contain halogen atoms;
R 3 =H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl;
R 4 =C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl;
with the proviso that when R 2 is —OH, —OCH 3 , or —OC(O)CF 3 and R 3 is —CH 3 , then R 4 is not —CH 2 (C 6 H 5 ), or —CH═CH—CH 3 , and
the further proviso that when R 3 is —CH 2 —(C 6 H 5 ), then R 4 is not —CH 3 or —CH 2 CH 3 .
2. A compound according to claim 1 , wherein R 5 is H, C 1 -C 10 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl or alkylaryl.
3. A compound according to claim 2 , wherein R 5 is H, or C 1 -C 10 alkyl.
4. A compound according to claim 1 , wherein R 3 is H, C 1 -C 10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, and R 4 is C 1 -C 10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl.
5. A compound according to claim 4 , wherein R 3 is H, or C 1 -C 10 alkyl, and R 4 is C 1 -C 10 alkyl.
6. A compound according to claim 1 , wherein, R 3 is —H or —CH 3 .
7. A compound according to claim 1 , wherein R 4 is -nC 6 -C 8 alkyl.
8. A compound according to claim 1 , wherein the compound is selected from the group consisting of:
9. A pharmaceutical composition comprising a pharmaceutical diluent and a compound according to claim 1 .
10. A compound according to claim 1 , where:
R 1 is H;
R 2 is —OCH 2 C(O)NHR 5 , where R 5 is C 1 -C 10 aryl containing a halogen atom;
R 3 is CH 3 ; and
R 4 is -n-C 6 -C 8 alkyl.
11. A pharmaceutical composition comprising a pharmaceutical diluent and the compound of claim 10 .