CA2093825A1 - Proanthocyanidin polymers having antiviral activity and methods of obtaining same - Google Patents
Proanthocyanidin polymers having antiviral activity and methods of obtaining sameInfo
- Publication number
- CA2093825A1 CA2093825A1 CA002093825A CA2093825A CA2093825A1 CA 2093825 A1 CA2093825 A1 CA 2093825A1 CA 002093825 A CA002093825 A CA 002093825A CA 2093825 A CA2093825 A CA 2093825A CA 2093825 A1 CA2093825 A1 CA 2093825A1
- Authority
- CA
- Canada
- Prior art keywords
- methods
- antiviral activity
- proanthocyanidin
- proanthocyanidin polymers
- obtaining same
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/765—Polymers containing oxygen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/16—Antivirals for RNA viruses for influenza or rhinoviruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
- C07D311/62—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2 with oxygen atoms directly attached in position 3, e.g. anthocyanidins
Abstract
The present invention provides for proanthocyanidin polymers with significant antiviral activity. The proanthocyanidin po-lymers can be chemically synthesized or can be isolated from a Croton or a Calophyllum plant species. The present invention en-compasses methods of using proanthocyanidin polymers in treating warm-blooded animals, including humans, infected with par-amyxovaridae such as respiratory syncytial virus, orthomyxovaridae such as influenza A, B and C, and herpes viruses such as Herpes Simplex virus.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US59689390A | 1990-10-12 | 1990-10-12 | |
US596,893 | 1990-10-12 | ||
US737,077 | 1991-07-29 | ||
US07/737,077 US5211944A (en) | 1990-10-12 | 1991-07-29 | Proanthocyanidin polymers having antiviral activity and methods of obtaining same |
PCT/US1991/007679 WO1992006695A1 (en) | 1990-10-12 | 1991-10-10 | Proanthocyanidin polymers having antiviral activity and methods of obtaining same |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2093825A1 true CA2093825A1 (en) | 1992-04-13 |
CA2093825C CA2093825C (en) | 2003-01-07 |
Family
ID=27082674
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002093825A Expired - Lifetime CA2093825C (en) | 1990-10-12 | 1991-10-10 | Proanthocyanidin polymers having antiviral activity and methods of obtaining same |
Country Status (12)
Country | Link |
---|---|
US (2) | US5211944A (en) |
EP (1) | EP0553253B1 (en) |
JP (1) | JP3448052B2 (en) |
KR (1) | KR100207949B1 (en) |
AT (1) | ATE194288T1 (en) |
AU (1) | AU660631B2 (en) |
CA (1) | CA2093825C (en) |
DE (1) | DE69132289D1 (en) |
MX (1) | MX9101540A (en) |
NZ (1) | NZ240200A (en) |
SG (1) | SG52707A1 (en) |
WO (1) | WO1992006695A1 (en) |
Families Citing this family (69)
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JP3103114B2 (en) * | 1992-03-31 | 2000-10-23 | アメリカ合衆国 | Calanolide antiviral compounds, compositions and uses thereof |
US5591770A (en) * | 1992-03-31 | 1997-01-07 | The United States Of America As Represented By The Department Of Health And Human Services | Calanolide and related antiretroviral compounds, compositions, and uses thereof |
US6774141B1 (en) | 1992-03-31 | 2004-08-10 | The United States Of America As Represented By The Secretary Of Health And Human Services | Calanolide and related antiviral compounds, compositions, and uses thereof |
US5650432A (en) * | 1995-03-24 | 1997-07-22 | Jlb, Inc. | Method of treating or preventing non-viral microbial infection |
US5646178A (en) * | 1992-10-09 | 1997-07-08 | Jlb, Inc. | Cranberry extract and biologically active compounds derived therefrom |
JP3426237B2 (en) * | 1993-05-28 | 2003-07-14 | ニューヨーク ブラッド センター,インコーポレイティド | Method for sterilizing biological compositions and formulations produced by this method |
US6277879B1 (en) | 1994-08-03 | 2001-08-21 | Sarawak Medichem Pharmaceuticals, Inc. | Calanolide analogues and methods of their use |
US6043271A (en) * | 1994-08-03 | 2000-03-28 | Sarawak Medichem Pharmaceuticals, Inc. | Method for the preparation of (±)-calanolide A and intermediates thereof |
US5892060A (en) * | 1994-08-03 | 1999-04-06 | Sarawak Medichem Pharmaceuticals, Inc. | Method for the preparation of (+)-calanolide a and analogues thereof |
US5977385A (en) * | 1994-08-03 | 1999-11-02 | Sarawak Medichem Pharmaceuticals | Method for the preparation of (+)-calanolide A and analogues thereof |
US5554645A (en) * | 1994-10-03 | 1996-09-10 | Mars, Incorporated | Antineoplastic cocoa extracts and methods for making and using the same |
JPH1059846A (en) * | 1996-06-10 | 1998-03-03 | Kikkoman Corp | Preventive or remedy for cararacta |
WO1998016111A1 (en) * | 1996-10-16 | 1998-04-23 | Shaman Pharmaceuticals, Inc. | Enteric formulations of proanthocyanidin polymer antidiarrheal compositions |
AU775330B2 (en) * | 1996-10-16 | 2004-07-29 | Napo Pharmaceuticals Inc. | Enteric formulations of proanthocyanidin polymer antidiarrheal compositions |
US5968973A (en) * | 1996-11-18 | 1999-10-19 | Cancer Institute (Hospital), Chinese Academy Of Medical Sciences | Method for treating hyperplasia |
US6197808B1 (en) * | 1996-11-18 | 2001-03-06 | Cancer Instititute (Hospital), Chinese Academy Of Medical Sciences | Methods for treating hyperplasia |
JP3213557B2 (en) * | 1996-11-18 | 2001-10-02 | 三井農林株式会社 | A remedy for condyloma acuminatum containing tea catechin as an active ingredient |
WO1999012541A1 (en) | 1997-09-09 | 1999-03-18 | Rutgers, The State University Of New Jersey | Plant proanthocyanidin extract effective at inhibiting adherence of bacteria with p-type fimbriae to surfaces |
US6060235A (en) | 1997-09-19 | 2000-05-09 | Geltex Pharmaceuticals, Inc. | Antiviral polymers comprising acid functional groups and hydrophobic groups |
WO2000047062A2 (en) * | 1999-02-01 | 2000-08-17 | Shaman Pharmaceuticals, Inc. | Enteric formulations of proanthocyanidin polymer dietary supplements and methods for preparing same |
EP1173442A2 (en) | 1999-04-26 | 2002-01-23 | Sarawak Medichem Pharmaceuticals Inc. | Methods for preparing antiviral calanolide compounds |
EP1223928A2 (en) | 1999-07-08 | 2002-07-24 | Patrick Thomas Prendergast | Use of flavones, coumarins and related compounds to treat infections |
EP1143807A3 (en) * | 1999-08-13 | 2002-09-11 | Dry Creek Nutrition, Inc. | Novel polyphenolic polymeric compositions, method of their isolation, and a method of altering and improving taste characteristics of edible consumables |
US6210681B1 (en) * | 1999-09-07 | 2001-04-03 | Jlb, Inc. | Plant proanthocyanidin extracts |
JP4963338B2 (en) * | 1999-10-20 | 2012-06-27 | 株式会社ダイセル | Cigarette smoke element and method for manufacturing the same |
US6391330B1 (en) | 2000-05-11 | 2002-05-21 | Michael A. Ross | Proanthocyanidins and ascorbic acid composition for topical application to human respiratory and oral mucosa |
AU2001288574B2 (en) * | 2000-08-31 | 2006-06-15 | Phenolics Llc | Efficient method for producing compositions enriched in anthocyanins |
US7306815B2 (en) * | 2000-08-31 | 2007-12-11 | Phenolics, Llc | Compositions enriched in phenolic compounds and methods for producing the same |
US6960360B2 (en) | 2000-08-31 | 2005-11-01 | Phenolics, Llc | Efficient method for producing compositions enriched in total phenols |
EP1213025A1 (en) * | 2000-12-06 | 2002-06-12 | Laboratoires Serobiologiques(Societe Anonyme) | Cosmetic and/or dermopharmaceutical composition containing extracts obtained from the leaves of Argania spinosa |
WO2003080593A1 (en) * | 2002-03-22 | 2003-10-02 | Beijing Jiankai Technology Co., Ltd. | Hydrophilic polymers-flavonoids conjugates and pharmaceutical compositions comprising them |
AU2003243191B2 (en) | 2002-05-02 | 2007-09-20 | President And Fellows Of Harvard College | Formulations limiting spread of pulmonary infections |
US7208183B2 (en) * | 2002-10-05 | 2007-04-24 | Bobrowski Paul J | Methods and preparations of the latex from the croton species |
US20040071793A1 (en) * | 2002-10-05 | 2004-04-15 | Bobrowski Paul J. | Oral rehydration methods and compositions |
AU2004220541B2 (en) * | 2003-03-12 | 2009-03-26 | Epitome Pharmaceuticals Limited | Rapidly absorbing lipophilic skin compositions and uses therefor |
FR2852842A1 (en) * | 2003-03-31 | 2004-10-01 | Silab Sa | Process for preparing an active component from the resin exudate of fruits of Daemonorops or Croton, useful for dermatological application to protect against free radicals |
US20050074510A1 (en) * | 2003-10-04 | 2005-04-07 | Bobrowski Paul J. | Topical preparations for use in treatment of anorectal disease |
US20050207983A1 (en) | 2004-03-05 | 2005-09-22 | Pulmatrix, Inc. | Formulations decreasing particle exhalation |
WO2005089780A1 (en) * | 2004-03-18 | 2005-09-29 | Umeda Jimusho Ltd. | Composition against aids virus and method of selectively inactivating virus-infected cells |
JP2005314316A (en) * | 2004-04-30 | 2005-11-10 | Kikkoman Corp | Anti-sars coronavirus agent |
US20070065486A1 (en) * | 2004-05-21 | 2007-03-22 | Migco Limited | Migraine remedy |
ES2245610B1 (en) * | 2004-06-23 | 2007-03-16 | Investigacion Y Nutricion, S.L. | PRODUCT OF VEGETABLE ORIGIN AND ITS OBTAINING PROCEDURE. |
US20060073220A1 (en) * | 2004-07-08 | 2006-04-06 | Daugherty F J | Cinnamon extract enriched for polyphenols and methods of preparing same |
US20060204600A1 (en) * | 2005-03-11 | 2006-09-14 | Paul Konz | Dragon's blood anti-viral materials and methods |
US20090076132A1 (en) * | 2005-03-11 | 2009-03-19 | Gary Pekoe | Antiviral compositions and methods of treatment |
JP2009535419A (en) | 2006-05-01 | 2009-10-01 | ナポ ファーマシューティカルズ インク. | Treatment of constipation-type irritable bowel syndrome |
PT2529626T (en) * | 2006-05-01 | 2018-02-27 | Napo Pharmaceuticals Inc | Compositions and methods for treating or preventing colon cancer |
US20070254050A1 (en) | 2006-05-01 | 2007-11-01 | Quart Barry D | Method for treatment of diarrhea-predominant irritable bowel syndrome |
WO2009099405A2 (en) * | 2008-01-30 | 2009-08-13 | Dalos, Llc | Antibacterial compositions and methods of treatment |
JP4892690B2 (en) * | 2008-09-03 | 2012-03-07 | 財団法人宮崎県産業支援財団 | Hepatitis C virus production inhibitor |
US8629121B2 (en) * | 2009-01-27 | 2014-01-14 | World Force Technologies, Llc | High molecular weight polysaccharide that binds and inhibits virus |
WO2011024049A2 (en) | 2009-08-26 | 2011-03-03 | Glenmark Pharmaceuticals Ltd | Method for producing proanthocyanidin polymer compositions for pharmaceutical formulations |
JP5343016B2 (en) * | 2010-01-22 | 2013-11-13 | 株式会社ロッテ | Anti-influenza virus agent and influenza infection suppression product obtained by adsorbing, impregnating and adding the same |
WO2012030664A1 (en) | 2010-08-30 | 2012-03-08 | Pulmatrix, Inc. | Dry powder formulations and methods for treating pulmonary diseases |
US8758824B2 (en) | 2010-08-30 | 2014-06-24 | Pulmatrix, Inc. | Respirably dry powder comprising calcium lactate, sodium chloride and leucine |
AU2011308865B2 (en) | 2010-09-29 | 2017-01-05 | Pulmatrix, Inc. | Monovalent metal cation dry powders for inhalation |
DK2621488T3 (en) | 2010-09-29 | 2019-03-04 | Pulmatrix Operating Co Inc | CATIONIC DRY POWDER |
US8962680B2 (en) | 2010-10-31 | 2015-02-24 | Salix Pharmaceuticals, Ltd. | Methods and compositions for treating HIV-associated diarrhea |
BR112013018688B1 (en) * | 2011-01-27 | 2021-08-24 | Napo Pharmaceuticals, Inc | METHOD OF PRODUCTION OF A POLYMER COMPOSITION OF PROANTHOCYANIDINE |
CN107596518B (en) | 2012-02-29 | 2021-04-23 | 普马特里克斯营业公司 | Inhalable dry powder |
IN2014MN01933A (en) * | 2012-03-13 | 2015-07-10 | Piramal Entpr Ltd | |
KR101349609B1 (en) * | 2012-06-08 | 2014-01-09 | 순천향대학교 산학협력단 | Indicator for Analysis of Vaccin for Fish and Method of Analysing Vaccine for Fish Using the Same |
EP2981247B1 (en) | 2013-04-01 | 2023-06-07 | Pulmatrix Operating Company, Inc. | Tiotropium dry powders |
JOP20190275A1 (en) | 2017-05-31 | 2019-11-27 | Napo Pharmaceuticals Inc | Methods and compositions for treating congenital diarrhea disorder |
JOP20190276A1 (en) | 2017-05-31 | 2019-11-27 | Napo Pharmaceuticals Inc | Methods and compositions for treating bile acid diarrhea, diarrhea associated with small intestine resection or gallbladder removal, and short bowel syndrome |
CN113613660B (en) * | 2019-03-29 | 2024-02-06 | 赢创运营有限公司 | Combination preparation comprising an anthocyanin composition and an antiviral agent |
CN114624367B (en) * | 2020-12-14 | 2023-05-09 | 四川大学 | Method for extracting bamboo leaf flavone by adopting solid oxonium salt solvent-free pressurization |
US20230060934A1 (en) * | 2021-08-25 | 2023-03-02 | Michael Wayne Dockery | Botanical antiviral nutritional supplement |
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---|---|---|---|---|
FR2226185A1 (en) * | 1973-04-20 | 1974-11-15 | Vincent Yves | Therapeutically active tannin fractions prepd. - from Cupressus sempervirens fruits by extracting with solvents |
CA1086651A (en) * | 1977-12-12 | 1980-09-30 | Her Majesty The Queen In Right Of Canada As Represented By The Minister Of Health And Welfare Canada | Compositions for, and treatment of, herpes viral infections |
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JPS59196884A (en) * | 1983-04-20 | 1984-11-08 | Nippon Shinyaku Co Ltd | Novel tannin |
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GB8518289D0 (en) * | 1985-07-19 | 1985-08-29 | Inverni Della Beffa Spa | Obtaining proanthocyanidine a2 |
JPH0231074B2 (en) * | 1986-08-26 | 1990-07-11 | Nippon Shinyaku Co Ltd | SHINTANNIN |
CA2001898A1 (en) * | 1988-10-31 | 1990-04-30 | Kuo-Hsiung Lee | Inhibition of human retroviruses |
JPH05504937A (en) * | 1989-05-12 | 1993-07-29 | カリエル,レオン | Compositions based on proanthocyanidol. Its pharmacological application |
-
1991
- 1991-07-29 US US07/737,077 patent/US5211944A/en not_active Expired - Lifetime
- 1991-10-10 WO PCT/US1991/007679 patent/WO1992006695A1/en active IP Right Grant
- 1991-10-10 JP JP51851291A patent/JP3448052B2/en not_active Expired - Lifetime
- 1991-10-10 AT AT91919754T patent/ATE194288T1/en not_active IP Right Cessation
- 1991-10-10 DE DE69132289T patent/DE69132289D1/en not_active Expired - Lifetime
- 1991-10-10 SG SG1996008125A patent/SG52707A1/en unknown
- 1991-10-10 CA CA002093825A patent/CA2093825C/en not_active Expired - Lifetime
- 1991-10-10 AU AU88780/91A patent/AU660631B2/en not_active Expired
- 1991-10-10 EP EP91919754A patent/EP0553253B1/en not_active Expired - Lifetime
- 1991-10-11 MX MX9101540A patent/MX9101540A/en unknown
- 1991-10-11 NZ NZ240200A patent/NZ240200A/en unknown
-
1994
- 1994-02-09 US US08/194,779 patent/US5494661A/en not_active Expired - Lifetime
-
1999
- 1999-11-01 KR KR1019930701100A patent/KR100207949B1/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
ATE194288T1 (en) | 2000-07-15 |
CA2093825C (en) | 2003-01-07 |
EP0553253A4 (en) | 1993-09-15 |
DE69132289D1 (en) | 2000-08-10 |
SG52707A1 (en) | 1998-09-28 |
EP0553253A1 (en) | 1993-08-04 |
JPH06502413A (en) | 1994-03-17 |
KR930702010A (en) | 1993-09-08 |
WO1992006695A1 (en) | 1992-04-30 |
US5211944A (en) | 1993-05-18 |
EP0553253B1 (en) | 2000-07-05 |
AU660631B2 (en) | 1995-07-06 |
JP3448052B2 (en) | 2003-09-16 |
NZ240200A (en) | 1994-04-27 |
KR100207949B1 (en) | 1999-07-15 |
AU8878091A (en) | 1992-05-20 |
US5494661A (en) | 1996-02-27 |
MX9101540A (en) | 1992-06-05 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request | ||
MKEX | Expiry | ||
MKEX | Expiry |
Effective date: 20111010 |