Compositions containing hypoglycemically active stilbenoids
AssigneeInsmed Incorporated
InventorsWayne D. Inman, David C. Hopp
Life of this patent
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Abstract
The use of isolated or purified stilbenoid compounds including longistyline A-2-carboxylic acid as hypoglycemic agents or to lower serum glucose levels is described. The invention also relates to the use of such stibenoid compounds in combination with other hypoglycemic agents.
Claims11
A method of lowering blood glucose in a mammal comprising administration to said mammal a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a hypoglycemically effective amount of an isolated compound having the formula (I):
- wherein,
- A is selected from the group consisting of a single bond and a double bond in trans conformation;
- R1 is selected from the group consisting of H, OH, C1-6alkoxy, COOH, and COOC1-6alkyl;
- R2 is selected from the group consisting of H, OH, and C1-10alkoxy;
- R3 is selected from the group consisting of H, C1-10alkyl, C2-10alkenyl, C2-10alkynyl, and C1-8cycloalkyl;
- R4 is selected from the group consisting of H, OH, and C1-10alkoxy;
- R5 are selected from the group consisting of H, C1-10alkyl, C2-10alkenyl,
- C2-10alkynyl, and C1-8cycloalkyl;
- R6 is selected from the group consisting of H, OH, C1-6alkoxy, COOH, and COOC1-6alkyl;
- R7 is selected from the group consisting of H, OH, C1-6alkoxy, COOH, and COOC1-6alkyl;
- and
- wherein at least one of R3 and R5 is selected from the group consisting of C1-10alkyl, C2-10alkenyl, C2-10alkynyl, and C1-8cycloalkyl;
- or a pharmaceutically acceptable salt thereof.
A method of lowering blood glucose in a mammal comprising administration to said mammal a pharmaceutical composition comprising a pharmaceutically acceptable carrier and a hypoglycemically effective amount of an isolated compound selected from the group consisting of:
- (A) Longistyline C;
- (B) Longistyline A;
- (C) longistyline A-6-carboxylic acid;
- (D) 7,8-dihydrolongistyline C;
- (E) 7,8,2″,3″-tetrahydrolongistyline C;
- (F) 7,8,2″,3″-tetrahydrolongistyline A-6-carboxylic acid;
- (G) 3-hydroxy-4isoprenyl-5-methoxystilbene-2-carboxylic acid;
- (H) 3-hydroxy-4-(3-methylbutyl)-5-methoxy-7,8-dihydrostilbene-2-carboxylic acid;
- (I) 4-isopentenylresveratrol (3,4′,5-trihydroxy-4-(3-methyl-2-butenyl)stilbene;
- (J) 3,5-dimethoxy-4-(3-methyl-2-butenyl)stilbene;
- (K) 3,4′,5-trimethoxy-4-(3-methyl-2-butenyl)stilbene;
- (L) chlorophorin;
- (M) 3,5-dimethoxy-4-(3-methyl-2-butenyl)bibenzene;
- (N) 3,5-dihydroxy-4-(3-methyl-2-butenyl)bibenzene;
- (O) 3,5-dihydroxy-4-(3-methyl-2-butenyl)bibenzyl-2-carboxylic acid;
- (P) 3-hydroxy-5-methoxy-4-(3-methyl-2-butenyl)bibenzene;
- (Q) 5-hydroxy-3-methoxy-4-(3-methyl-2-butenyl)bibenzene;
- (R) 3,5-dihydroxy-2-(3-methyl1-2-butenyl1)bibenzene;
- (S) 3-hydroxy-5-methoxy-2-(3-methyl-2-butenyl)bibenzene;
- (T) 5-hydroxy-3-methoxy-2-(3-methyl-2-butenyl)bibenzene;
- (U) 3,5-dihydroxy-4-(3,7-dimethyl-2,6-octadienyl)-bibenzene;
- (V) 3,5-dimethoxy-4-(3,7-dimethyl-2,6-octadienyl)-bibenzene;
- (W) 3,5-diacetyl-4-(3,7-dimethyl-2,6-octadienyl)-bibenzene;
- (X) 3,4′,5-trihydroxy4-(3,7-dimethyl-2,6-octadienyl)-bibenzene;
- (Y) 3,5-dihydroxy-4-(3,7-dimethyloctyl)bibenzene;
- (Z) 3,5-dimethoxy-4-(3,7-dimethyloctyl)bibenzene;
- (AA) 2-geranyl-3,5-dihydroxybibenzene;
- (AB) 2-geranyl-3,5-dimethoxybibenzene;
- (AC) 2-geranyl-3-hydroxy-5-methoxybibenzene;
- and
- (AD) 3-methoxy-4′-hydroxy-4-(3-methyl-2-butenyl)bibenzene.
Dependencies are inferred from the claim text.