Polymeric boronic acid derivatives as lipase inhibitors
OwnerChad Huval, Xinhua Li +2inventors
InventorsChad Huval, Xinhua Li, Stephen Holmes-Farley, Pradeep Dhal
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Abstract
Human obesity is a health problem affecting a significant proportion of the American population. Numerous methods of treating obesity have been developed, but all have serious drawbacks. The present invention discloses a novel class of polymers with either a sulfur atom or an electron withdrawing group between a polymer backbone and a pendant aryl boronic acid group. Polymers having such an electron withdrawing group have been found to be particularly effective in inhibiting lipase in vitro and in vivo. Methods of treating obesity and reducing absorption of fat are also disclosed.
Claims47
A polymer substituted with at least one group represented by Structural Formula (I) or (II):
- wherein:
- R is a C6-C30 hydrocarbylene group optionally interrupted by one or more heteroatoms selected from the group consisting of NH, S, and O;
- each X is independently a substituted or unsubstituted alkyl group, an electron withdrawing group, or an electron donating group meta to the boronic acid moiety;
- Y is —C(O)Z-, -ZC(O)— or —S(CH2)n—;
- Z is a bond, CH2S, S, NH, or O;
- m is an integer from 0 to 3;
- k is an integer from 0 to 4;
- and
- n is an integer from 0 to 5.
19-23. (canceled)
A method for treating obesity in a mammal, comprising the step of orally administering to the mammal an effective amount of a polymer substituted with at least one group represented by Structural Formula (I) or (II):
- wherein:
- R is a C6-C30 hydrocarbylene group optionally interrupted by one or more heteroatoms selected from the group consisting of NH, S, and O;
- R1 is —H or a lower alkyl group;
- R2 is —H, a lower alkyl group, or is absent;
- each X is independently —H, a substituted or unsubstituted alkyl group, an electron withdrawing group, or an electron donating group meta to the boronic acid moiety;
- Y is —C(O)Z-, -ZC(O)— or —S(CH2)n—;
- Z is a bond, CH2S, S, NH, or O;
- Z1 is a bond, —C(O)NH—, —C(O)O—, —C6H4O—, or —C6H4NHC(O)—;
- m is an integer from 0 to 3;
- k is an integer from 0 to 4;
- n is an integer from 0 to 5.
43-47. (canceled)
A method for reducing absorption of fat in a mammal in need of such treatment, comprising the step of orally administering to the mammal an effective amount of a polymer substituted with at least one group represented by Structural Formula (I) or (II):
- wherein:
- R is a C6-C30 hydrocarbylene group optionally interrupted by one or more heteroatoms selected from the group consisting of NH, S and O;
- each X is independently —H, a substituted or unsubstituted alkyl group, an electron withdrawing group, or an electron donating group meta to the boronic acid moiety;
- Y is —C(O)Z-, -ZC(O)— or —S(CH2)n—;
- Z is a bond, CH2S, S, NH, or 0;
- m is an integer from 0 to 3;
- k is an integer from 0 to 4;
- and
- n is an integer from 0 to 5.
(canceled)
Dependencies are inferred from the claim text.