Back to results
US 5,211,944 AGranted
Proanthocyanidin polymers having antiviral activity and methods of obtaining same
AssigneeShaman Pharmaceuticals, Inc.
InventorMichael S. Tempesta
Life of this patent
Estimating the term…
Abstract
The present invention provides for proanthocyanidin polymers with significant antiviral activity. The proanthocyanidin polymers can be chemically synthesized or can be isolated from a Croton or a Calophyllum plant species. The present invention encompasses methods of using proanthocyanidin polymers in treating warm-blooded animals, including humans, infected with paramyxovaridae such as respiratory syncytial virus, orthomyxovaridae such as influenza A, B and C, and herpes viruses such as Herpes Simplex virus.
Claims20
A proanthocyanidin polymer composition, characterized by:
- (a) the capability of dissolving in water and/or aqueous solution;
- (b) the capability of exerting a pronounced antiviral effect as demonstrated in in vitro assays for antiviral activity against respiratory syncytial virus, types A and B;
- parainfluenza virus, types 1 and 3;
- influenza virus, types A and B;
- and as demonstrated in in vivo tests for antiviral activity against respiratory syncytial virus;
- influenza virus, type A;
- parainfluenza virus, type 3;
- and herpes simplex virus, type 2;
- (c) comprising a proanthocyanidin polymer having a structure comprising flavonoid units selected from the group consisting of catechins, epicatechins, gallocatechins, galloepicatechins and combinations thereof;
- and
- (d) .sup.13 C NMR spectra having peak positions at .delta. 154.2, 145.1, 143.7, 132.8, 131.2, 130.3, 120.9-118.6 (series of broad peaks), 116.1, 115.4, 114.3, 108.0, 106.3, 96.6, 95.3, 81.8, 77.6, 75.3, 72.6, 1.5, 65.6, 37.1, 35.3, and 27.7.
8 more elements
An ester, ether or oxonium derivative of a proanthocyanidin polymer, in which the polymer is characterized by:
- (a) the capability of dissolving in water and/or aqueous solution;
- (b) the capability of exerting a pronounced antiviral effect as demonstrated in in vitro assays for antiviral activity against respiratory syncytial virus, types A and B;
- parainfluenza virus, types 1 and 3;
- influenza virus, types A and B;
- and as demonstrated in in vivo tests for antiviral activity against respiratory syncytial virus;
- influenza virus, type A;
- parainfluenza virus, type 3;
- and herpes simplex virus, type 2;
- (c) having a structure comprising flavonoid units selected from the group consisting of catechins, epicatechins, gallocatechins, galloepicatechins and combinations thereof;
- and
- (d) .sup.13 C NMR spectra having peak positions at .delta. 154.2, 145.1, 143.7, 132.8, 131.2, 130.3, 120.9-118.6 (series of broad peaks), 116.1, 115.4, 114.3, 108.0, 106.3, 96.6, 95.3, 81.8, 77.6, 75.3, 72.6, 71.5, 65.6, 37.1, 35.3, and 27.7.
8 more elements
A proanthocyanidin polymer composition characterized by:
- (a) the capability of dissolving in water and/or an aqueous solution;
- (b) the capability of exerting an antiviral effect as demonstrated in in vitro assays for antiviral activity against respiratory syncytial virus, types A and B;
- parainfluenza virus, types 1 and 3;
- influenza virus, types A and B;
- and as demonstrated in in vivo tests for antiviral activity against respiratory syncytial virus;
- influenza virus, type A;
- parainfluenza virus, type 3;
- and herpes simplex virus, type 2;
- (c) comprising a proanthocyanidin polymer having a structure comprising flavonoid units selected from the group consisting of catechins and epicatechins;
- and
- (d) a .sup.13 C NMR spectra substantially as illustrated in FIG. 4.
8 more elements
An ester, ether or oxonium derivative of a proanthocyanidin polymer, in which the polymer is characterized by:
- (a) the capability of dissolving in water and/or aqueous solution;
- (b) the capability of exerting an antiviral effect as demonstrated in in vitro assays for antiviral activity against respiratory syncytial virus, types A and B;
- parainfluenza virus, types 1 and 3;
- influenza virus, types A and B;
- and as demonstrated in in vivo tests for antiviral activity against respiratory syncytial virus;
- influenza virus, type A;
- parainfluenza virus, type 3;
- and herpes simplex virus, type 2;
- (c) comprising a proanthocyanidin polymer having a structure comprising flavonoid units selected from the group consisting of catechins and epicatechins;
- and
- (d) a .sup.13 C NMR spectra substantially as illustrated in FIG. 4.
8 more elements
A proanthocyanidin polymer composition obtained from a Croton tree by a method which comprises:
- (a) extracting the whole plane, the bark, the stems, the roots or the latex of the Croton tree with a lower alcohol of about 1-3 carbons, acetone, water or other water miscible solvent or combinations thereof to obtain an aqueous soluble fraction;
- (b) subjecting the aqueous soluble fraction to gel filtration, ultrafiltration or chromatography using aqueous and/or organic solvents;
- or combination thereof and
- (c) collecting the fraction detectable by ultra violet spectroscopy having a .lambda. maximum at about 200-350 nm, wherein the collected fraction is characterized by having .sup.13 C NMR spectra having peak positions at .delta.154.2, 145.1, 143.7, 132.8, 131.2, 130.3, 120.9-118.6 (series of broad peaks), 116.1, 115.4, 114.3, 108.0, 106.3, 96.6, 95.3, 81.8, 77.6, 75.3, 72.6, 71.5, 65.6, 37.1, 35.3, and 27.7.
1 more element
A proanthocyanidin polymer composition obtained from Calophyllum inophylum by a method which comprises:
- (a) extracting the whole plane, the bark, the stems, the roots or the latex of the Calophyllum inophylum with a lower alcohol of about 1-3 carbons, acetone, water or other water miscible solvent or combinations thereof to obtain an aqueous soluble fraction;
- (b) subjecting the aqueous soluble fraction to gel filtration, ultrafiltration or chromatography using aqueous and/or organic solvents;
- or combination thereof and
- (c) collecting the fraction detectable by ultra violet spectroscopy having a .lambda. maximum at about 200-350 nm, wherein the collected fraction is characterized by having .sup.13 C NMR spectra having peak positions at .delta.154.2, 145.1, 143.7, 132.8, 131.2, 130.3, 120.9-118.6 (series of broad peaks), 116.1, 115.4, 114.3, 108.0, 106.3, 96.6, 95.3, 81.8, 77.6, 75.3, 72.6, 71.5, 65.6, 37.1, 35.3, and 27.7.
1 more element
Dependencies are inferred from the claim text.