US2005148768A1PendingUtilityA1
Cobalt-porphyrin complexes and use thereof as an anti-obesity agent
Est. expiryDec 15, 2020(expired)· nominal 20-yr term from priority
C07D 487/22A61P 3/04
50
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Claims
Abstract
Cobalt-porphyrin (Co-P) complexes for use as anti-obesity agents, and compositions and methods related thereto. The Co-P complexes exhibit reduced redox activity compared to cobalt mesoporphyrin (Co-MP) and cobalt protoporphyrin (Co-PP), which alleviates the deleterious effects associated with administration of Co-P associated with oxidative stress, particularly in the context of injection site toxicity.
Claims
exact text as granted — not AI-modified1 . A cobalt-porphyrin complex having the structure:
or a salt thereof, wherein:
R 1 and R 2 are the same or different and independently —(CH 2 ) n -A-R 5 , wherein A is —C(═O)O—, —OC(═O)—, —C(═O)N(R)—, —N(R)C(═O)—, —C(═O)—, —N(R)—, —O— or —S—, and R is hydrogen, alkyl, substituted alkyl, arylalkyl, or substituted arylalkyl, and n is 2 or 3;
R 3 and R 4 are the same or different and independently —CH═CH 2 or —CH 2 CH 3 ;
R 5 is, at each occurrence, the same or different and independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl or substituted arylalkyl; and
L 1 and L 2 are optional ligands;
and with the proviso that the cobalt-porphyrin complex of structure (I) has no more than 5% of the redox activity of cobalt mesoporphyrin.
2 . The complex of claim 1 wherein A is —C(═O)O—.
3 . The complex of claim 1 wherein A is —OC(═O)—.
4 . The complex of claim 1 wherein A is —C(═O)N(R)—.
5 . The complex of claim 1 wherein A is —N(R)C(═O)—.
6 . The complex of claim 1 wherein A is —C(═O)—.
7 . The complex of claim 1 wherein A is —N(R)—.
8 . The complex of claim 1 wherein A is —O—.
9 . The complex of claim 1 wherein A is —S—.
10 . The complex of claim 1 wherein n is 2.
11 . The complex of claim 1 wherein n is 3.
12 . The complex of claim 1 wherein R is hydrogen.
13 . The complex of claim 1 wherein R is lower alkyl.
14 . The complex of claim 1 wherein R 5 is hydrogen.
15 . The complex of claim 1 wherein R 5 is alkyl.
16 . The complex of claim 15 wherein R 5 is lower alkyl.
17 . The complex of claim 1 wherein R 5 is substituted alkyl.
18 . The complex of claim 1 wherein R 5 is aryl or substituted aryl.
19 . The complex of claim 1 wherein R 5 is arylalkyl or substituted arylalkyl.
20 . The complex of claim 19 wherein arylalkyl is benzyl.
21 . The complex of claim 1 wherein R 3 and R 4 are the same.
22 . The complex of claim 20 wherein R 3 and R 4 are —CH═CH 2 .
23 . The complex of claim 20 wherein R 3 and R 4 are —CH 2 CH 3 .
24 . The complex of claim 1 wherein at least one of L 1 or L 2 is present.
25 . The complex of claim 1 wherein both L 1 and L 2 are present.
26 . The complex of claim 25 wherein L 1 and L 2 are glycinate.
27 . The complex of claim 25 wherein L 1 and L 2 are imidazole.
28 . The complex of claim 25 wherein L 1 and L 2 are halogen.
29 . The complex of claim 25 wherein L 1 and L 2 are a mono- or di-substituted amino.
30 . The complex of claim 25 where L 1 and L 2 are a substituted or unsubstituted heterocycle.
31 . A composition comprising a compound of claim 1 in combination with a pharmaceutically acceptable carrier.
32 . A method for treating obesity, comprising administering an effective amount of a composition comprising a cobalt-porphyrin complex and a pharmaceutically acceptable carrier, wherein the cobalt-porphyrin complex has the structure:
or a salt thereof, wherein:
R 1 and R 2 are the same or different and independently —(CH 2 ) n -A-R 5 , wherein A is —C(═O)O—, —OC(═O)—, —C(═O)N(R)—, —N(R)C(═O)—, —C(═O)—, —O— or —S—, and R is hydrogen, alkyl, substituted alkyl, arylalkyl, or substituted arylalkyl, and n is 2 or 3;
R 3 and R 4 are the same or different and independently —CH═CH 2 or —CH 2 CH 3 ;
R 5 is, at each occurrence, the same or different and independently hydrogen, alkyl, substituted alkyl, aryl, substituted aryl, arylalkyl or substituted arylalkyl; and
L 1 and L 2 are optional ligands;
and with the proviso that the cobalt-porphyrin complex of structure (I) has no more than 50% of the redox activity of cobalt mesoporphyrin.
33 . The method of claim 32 wherein the composition is administered by injection.
34 . The complex of claim 32 wherein A is —C(═O)O—.
35 . The complex of claim 32 wherein A is —OC(═O)—.
36 . The complex of claim 32 wherein A is —C(═O)N(R)—.
37 . The complex of claim 32 wherein A is —N(R)C(═O)—.
38 . The complex of claim 32 wherein A is —C(═O)—.
39 . The complex of claim 32 wherein A is —N(R)—.
40 . The complex of claim 32 wherein A is —O—.
41 . The complex of claim 32 wherein A is —S—.
42 . The complex of claim 32 wherein n is 2 .
43 . The complex of claim 32 wherein n is 3 .
44 . The complex of claim 32 wherein R is hydrogen.
45 . The complex of claim 32 wherein R is lower alkyl.
46 . The complex of claim 32 wherein R 5 is hydrogen.
47 . The complex of claim 32 wherein R 5 is alkyl.
48 . The complex of claim 47 wherein R 5 is lower alkyl.
49 . The complex of claim 32 wherein R 5 is substituted alkyl.
50 . The complex of claim 32 wherein R 5 is aryl or substituted aryl.
51 . The complex of claim 50 wherein R 5 is arylalkyl or substituted arylalkyl.
52 . The complex of claim 51 wherein arylalkyl is benzyl.
53 . The complex of claim 32 wherein R 3 and R 4 are the same.
54 . The complex of claim 53 wherein R 3 and R 4 are —CH═CH 2 .
55 . The complex of claim 53 wherein R 3 and R 4 are —CH 2 CH 3 .
56 . The complex of claim 32 wherein one of L 1 or L 2 is present.
57 . The complex of claim 32 wherein both L 1 and L 2 are present.
58 . The complex of claim 57 wherein L 1 and L 2 are glycinate.
59 . The complex of claim 57 wherein L 1 and L 2 are imidazole.
60 . The complex of claim 57 wherein L 1 and L 2 are halogen.
61 . The complex of claim 57 wherein L 1 and L 2 are a mono- or di-substituted amino.
62 . The complex of claim 57 wherein, and L 2 are a substituted or unsubstituted heterocycle.Cited by (0)
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