Patent US4760135A successfully refreshed from Google Patents.
US4760135A
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Phloretin and phlorizin derivative containing compounds
Assignee: KENTUCKY RESEARCH FOUNDATION A CORP OF, University of
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Filing: 1984-09-06
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Granted: 1988-07-26
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Expires: 2004-09-06
Abstract
Abstract Compounds including phloretin and/or phlorizin derivatives coupled to an undigestible and non-absorbable matrix are provided. The compounds have pharmacological efficacies. They inhibit sugar uptake from the intestine and may be used in composition form in methods for treating diabetes and for promoting weight loss. A method for the manufacture of these compounds and a novel intermediate phlorizin derivative for making these compounds are also disclosed.
Inventors
- 👤 Donald F. Diedrich
- 👤 Susanne L. Diedrich
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 20:04
CPC Classifications
C; C08; C08B; C08B11/00; C08B11/20; A; A61; A61K; A61K47/00; A61K47/50; A61K47/51; A61K47/56; A61K47/61; C07; C07H; C07H17/00; C07H17/04; C07H17/06; C07H17/065; C07H17/07
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
218 words
A compound, consisting of: a reaction product formed by serially coupling (1) an undigestible and non-absorbable polysaccharide matrix with a leash forming compound selected from a group consisting of glycine, N-N-diaminopropylmethylamine, tartaric acid, glutardialdehyde and NH 2 --(CHOH) n --CO 2 H wherein n=1-6 by dissolving the leash forming compound and matrix together in a solvent maintained at a pH of substantially 5.8 and then adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst to promote coupling and obtain a first intermediate product; (2) said first intermediate product with an intermediate inhibitory compound selected from a group consisting of compounds having the following structures: ##STR6## wherein R=--OH or --H and R 1 is a primary amine of from 1-10 carbon atoms effective in inhibiting glucose uptake by dissolving said first intermediate product and said intermediate inhibitory compound in solvents, mixing the solvents, and adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst to promote coupling while maintaining the pH of the mixed solvents at substantially 5.8 so as to form a second intermediate product; and (3) said second intermediate product with a promoter forming compound selected from a group consisting of ethylenediamine and ethanolamine by dissolving said promoter forming compound and said second intermediate product in solvent maintained at a pH of substantially 5.8 and adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst.
Claim 2
Dependent Claim
218 words
A compound, consisting of: a reaction product formed by serially coupling (1) an undigestible and non-absorbable polysaccharide matrix with a leash forming compound selected from a group consisting of glycine, N-N-diaminopropylmethylamine, tartaric acid, glutardialdehyde and NH 2 --(CHOH) n --CO 2 H wherein n=1-6 by dissolving the leash forming compound and matrix together in a solvent maintained at a pH of substantially 5.8 and then adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst to promote coupling and obtain a first intermediate product; (2) said first intermediate product with an intermediate inhibitory compound selected from a group consisting of compounds having the following structures: ##STR6## wherein R=--OH or --H and R 1 is a primary amine of from 1-10 carbon atoms effective in inhibiting glucose uptake by dissolving said first intermediate product and said intermediate inhibitory compound in solvents, mixing the solvents, and adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst to promote coupling while maintaining the pH of the mixed solvents at substantially 5.8 so as to form a second intermediate product; and (3) said second intermediate product with a promoter forming compound selected from a group consisting of ethylenediamine and ethanolamine by dissolving said promoter forming compound and said second intermediate product in solvent maintained at a pH of substantially 5.8 and adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst.
Claim 3
Dependent Claim
12 words
The compound of claim 1, wherein R 1 includes an aromatic ring.
Claim 4
Dependent Claim
12 words
The compound of claim 1, wherein said intermediate inhibitory compound is phlorizin-5'-benzylamine.
Claim 5
Dependent Claim
12 words
The compound of claim 1, wherein said intermediate inhibitory compound is 4'-deoxyphlorizin-5'-benzylamine.
Claim 6
Dependent Claim
12 words
The compound of claim 1, wherein said intermediate inhibitory compound is phloretin-3'-benzylamine.
Claim 7
Dependent Claim
17 words
The compound of claim 1, wherein said polysaccharide matrix has a molecular weight of from 25,000-90,000 daltons.
Claim 8
Dependent Claim
57 words
The compound of claim 1, wherein said polysaccharide matrix includes substantially 150-500 monomeric units selected from a group consisting of ##STR7## and any mixtures thereof, wherein R=--OH, --O--CH 2 --CO 2 H, --O--CH 2 --CHOH--CH 2 Br, --Si(OC 2 H 5 ) 2 --C 3 H 6 NH 2 , --NH 2 , or --NH--CO--CH 3 .
Claim 9
Dependent Claim
10 words
The compound of claim 1, wherein said matrix is carboxymethylcellulose.
Claim 10
Dependent Claim
11 words
The compound of claim 1, wherein said matrix is sodium carboxymethylcellulose.
Claim 11
Dependent Claim
19 words
The compound of claim 1, wherein said matrix is a carboxymethyl derivative of a galactomannan from the guar plant.
Claim 12
Dependent Claim
18 words
The compound of claim 1, wherein said matrix is a water soluble cross-linked dextran of substantially 70,000 daltons.
Claim 13
Dependent Claim
10 words
The compound of claim 1, wherein said matrix is CH-Sepharose.
Claim 14
Dependent Claim
20 words
The compound of claim 1, wherein said matrix is an N-hydroxysuccinimide-activated ester of a derivatized cross-linked agarose gel bead support.
Claim 15
Dependent Claim
164 words
A compound effective in inhibiting glucose uptake in a mammalian intestine, consisting of: a reaction product formed by serially coupling (1) a polysaccharide matrix with a leash forming compound selected from a group consisting of glycine, N-N-diaminopropylmethylamine, tartaric acid, glutardialdehyde and NH 2 --(CHOH) n --CO 2 H wherein n=1-6 by dissolving the leash forming compound and matrix together in a solvent maintained at a pH of substantially 5.8 and then adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst to promote coupling and obtain a first intermediate product and (2) said first intermediate product with an intermediate inhibitory compound selected from a group consisting of compounds having the following structures: ##STR8## wherein R=--OH or --H and R 1 is a primary amine of from 1-10 carbon atoms by dissolving said first intermediate product and said intermediate inhibitory compound in solvents, mixing the solvents, and adding 1-ethyl-3-(3-dimethylaminopropyl) carboddimide HCl as a catalyst to promote coupling while maintaining the pH of the mixed solvents at substantially 5.8.
Claim 16
Dependent Claim
164 words
A compound effective in inhibiting glucose uptake in a mammalian intestine, consisting of: a reaction product formed by serially coupling (1) a polysaccharide matrix with a leash forming compound selected from a group consisting of glycine, N-N-diaminopropylmethylamine, tartaric acid, glutardialdehyde and NH 2 --(CHOH) n --CO 2 H wherein n=1-6 by dissolving the leash forming compound and matrix together in a solvent maintained at a pH of substantially 5.8 and then adding 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide HCl as a catalyst to promote coupling and obtain a first intermediate product and (2) said first intermediate product with an intermediate inhibitory compound selected from a group consisting of compounds having the following structures: ##STR8## wherein R=--OH or --H and R 1 is a primary amine of from 1-10 carbon atoms by dissolving said first intermediate product and said intermediate inhibitory compound in solvents, mixing the solvents, and adding 1-ethyl-3-(3-dimethylaminopropyl) carboddimide HCl as a catalyst to promote coupling while maintaining the pH of the mixed solvents at substantially 5.8.
Claim 17
Dependent Claim
57 words
The compound of claim 14, wherein said polysaccharide matrix includes monomeric units selected from a group consisting of ##STR9## and any mixtures thereof, wherein R=--OH, --O--CH 2 --CO 2 --CO 2 H, --O--CH 2 --CHOH--CH 2 Br, --Si(OC 2 H 5 ) 2 --C 3 H 6 NH 2 ; --NH 2 , or --NH--CO--CH 3 .
References Cited (Backward Citations)
US3523937A
Cited
US4224439A
Cited
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