US2010120901A1PendingUtilityA1
Novel compounds, pharmaceutical compositions containing same, and methods of use for same
Est. expiryJul 9, 2022(expired)· nominal 20-yr term from priority
A61P 43/00C07D 409/12A61P 31/04A61P 3/00A61P 35/00A61P 3/04A61P 31/00C07D 333/32
32
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Claims
Abstract
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.
Claims
exact text as granted — not AI-modified1 - 8 . (canceled)
9 . A compound of formula II:
wherein
R 6 =C 2 -C 20 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, or alkylaryl, —CHR 10 OR 11 , —CO(O)R 10 , —C(O)NR 10 R 11 , —CH 2 C(O)R 10 , or —CH 2 C(O)NHR 10 , where R 10 and R 11 are each independently H, C 1 -C 10 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, or alkylaryl, optionally containing halogen atoms, but R 6 is not di-, tri-, or tetra-alkyl substituted phenyl;
R 7 =—OH, —OR 12 , —OCH 2 C(O)R 12 , —OCH 2 C(O)NHR 12 , —OC(O)R 12 , —OC(O)OR 12 , —OC(O)NHNH—R 12 or —OC(O)NR 12 R 13 , where R 12 and R 13 are each independently H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, or alkylaryl, and where R 12 and R 13 can optionally contain halogen atoms;
R 8 =H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl;
R 9 =C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl;
with the following provisos:
when R 6 is ethyl, if R 8 and R 9 are not the same, then R 8 or R 9 are not ethyl or —CH 2 (C 6 H 5 ), but R 8 and R 9 can be the same, even if R 6 is ethyl, and
when R 6 is phenyl, and R 7 is —OH, R 8 and R 9 cannot simultaneously be —CH 3 and -propenyl, and
when R 6 is phenyl, R 8 and R 9 cannot simultaneously be —CH 3 or —CH 2 —(C 6 H 5 ).
10 . A compound according to claim 9 , wherein R 10 is C 1 -C 10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl.
11 . A compound according to claim 9 , wherein R 8 is —H or —CH 3 .
12 . A compound according to claim 9 , wherein R 9 is -nC 6 -C 8 alkyl.
13 . A compound according to claim 9 , wherein the compound is selected from the group consisting of:
14 . A compound of formula III:
wherein
R 14 =—C(O)R 18 , where R 18 is H, C 1 -C 10 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl, optionally containing halogen atoms;
R 15 =—OH, —OR 19 , —OCH 2 C(O)R 19 , —OCH 2 C(O)NHR 19 , —OC(O)R 19 , —OC(O)OR 19 , —OC(O)NHNH—R 19 , or —OC(O)NR 19 R 20 , where R 19 and R 20 are each independently H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, or alkylaryl, and where R 19 and R 20 can each optionally contain halogen atoms;
R 16 =H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl;
R 17 =C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl;
with the following provisos:
when R 14 is —C(O)CH 3 , then R 16 and/or R 17 are not geranyl, p-fluorobenzyl, cinnamyl, farnesyl, methyl, or —CH 2 —(C 6 H 5 ), and
when R 14 is —C(O)C 6 H 5 , then either R 16 or R 17 are not methyl.
15 . A compound according to claim 14 , wherein the compound is selected from the group consisting of:
16 . 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)OR 27 , —OCH 2 C(O)NHR 27 , —OC(O)R 27 , —OC(O)OR 27 , —OC(O)NHNH—R 27 , or —OC(O)NR 27 R 28 , where R 27 and R 28 are each independently H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, or alkylaryl, and where R 27 and R 28 can each optionally contain halogen atoms;
R 23 =H, C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl; and
R 24 =C 1 -C 20 alkyl, cycloalkyl, alkenyl, aryl, arylalkyl, or alkylaryl.
17 . A pharmaceutical composition according to claim 16 , wherein the compound is selected from the group consisting of:
18 . (canceled)
19 . A pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula II.
20 . A pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula III.
21 . A method of inducing weight loss in an animal or human subject comprising administering an effective amount of a pharmaceutical composition according to claim 16 to said subject.
22 . The method of claim 21 , wherein the subject is a human.
23 . The method of claim 21 , wherein the subject is an animal.
24 . The method of claim 22 , wherein the pharmaceutical composition comprises a compound selected from the group consisting of:
25 . The method of claim 23 , wherein the pharmaceutical composition comprises a compound selected from the group consisting of:
26 . A method of treating cancer in an animal or human subject, comprising administering an effective amount of a pharmaceutical composition according to claim 16 to said subject.
27 . The method of claim 26 , wherein the subject is a human.
28 . The method of claim 26 , wherein the subject is an animal.
29 . The method of claim 27 , wherein the pharmaceutical composition comprises a compound selected from the group consisting of:
30 . The method of claim 28 , wherein the pharmaceutical composition comprises a compound selected from the group consisting of:
31 . A method of stimulating the activity of CPT-1 in an animal or human subject comprising administering an effective amount of a pharmaceutical composition according to claim 16 to said subject.
32 . The method of claim 31 , wherein the subject is a human.
33 . The method of claim 31 , wherein the subject is an animal.
34 . The method of claim 32 , wherein the compound is selected from the group consisting of:
35 . The method of claim 33 , wherein the compound is selected from the group consisting of:
36 . A method of inhibiting the activity of neuropeptide-Y in an animal or human subject comprising administering an effective amount of a pharmaceutical composition according to claim 16 to said subject.
37 . The method of claim 36 , wherein the subject is a human.
38 . The method of claim 36 , wherein the subject is an animal.
39 . A method of inhibiting fatty acid synthase activity in an animal or human subject comprising administering an effective amount of a pharmaceutical composition according to claim 16 to said subject.
40 . The method of claim 39 , wherein the subject is a human.
41 . The method of claim 39 , wherein the subject is an animal.
42 . A method of inhibiting growth of invasive microbial cells in an animal or human subject comprising the administration of an effective amount of a pharmaceutical composition according to claim 16 to said subject.
43 . The method of claim 42 , wherein the subject is a human.
44 . The method of claim 42 , wherein the subject is an animal.
45 . The method of claim 43 , wherein the compound is selected from the group consisting of:
46 . The method of claim 44 , wherein the compound is selected from the group consisting of:
47 . A pharmaceutical composition comprising a pharmaceutical diluent and a compound of formula:Cited by (0)
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