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US4644011A
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Pharmaceutical preparations containing (+)-cyanidan-3-ol derivatives, the use thereof, novel substituted (+)-cyanidan-3-ol derivatives, and processes for producing them
Assignee: Haleon CH SARL
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Filing: 1985-07-09
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Granted: 1987-02-17
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Expires: 2005-07-09
Abstract
Abstract Pharmaceutical preparations containing (+)-cyanidan-3-ol derivatives of the formula I ##STR1## wherein R' and R" are hydrogen, an unsubstituted or substituted hydrocarbon radical, or heterocyclic radical, halogen, formyl, free or functionally modified carboxyl, free or etherified or esterified hydroxyl, free, etherified or oxidized mercapto, unsubstituted or substituted sulfamoyl, acyl or unsubstituted or substituted amino, where however R' and R" cannot both be hydrogen simultaneously, and R 1 , R 2 , R 3 , R 4 and R 5 are each hydrogen or an unsubstituted or substituted hydrocarbon radical, and R 2 and R 3 together can also be an unsubstituted or substituted methylene group, and R 1 also an acyl group or an amidated carboxyl group; and therapeutically applicable salts of these compounds, as well as new compounds of these preparations. These pharmaceutical preparations are particularly valuable for treating liver and venous diseases.
Inventors
- 👤 Marc E. Ballenegger
- 👤 Christian G. Rimbault
- 👤 Alban I. Albert
- 👤 Andre J. Weith
- 👤 Pierre Courbat
- 👤 Robert G. Tyson
- 👤 Derek R. Palmer
- 👤 David G. Thompson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:32
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/74; C07D407/00; C07D407/02; C07D407/04; A; A61; A61K; A61K31/00; A61K31/33; A61K31/335; A61K31/35; A61K31/357; A61K31/36; A61P; A61P1/00; A61P1/16; A61P9/00; C07D311/04; C07D311/58; C07D311/60; C07D311/62
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
107 words
A pharmaceutical preparation for the treatment of a liver disease comprising a therapeutically effective amount of a compound of the formula ##STR5## wherein R' is hydrogen, halogen, or C 1 -C 7 alkylbenzyl; R" is C 1 -C 7 -alkyl which is substituted by hydroxy-imino; C 2 -C 7 -alkenyl substituted by acetoxymethylthio; C 1 -C 7 -alkylbenzyl; formyl; or trifluoroacetyl; and R 1 , R 2 , R 3 , R 4 , and R 5 are each hydrogen, C 1 -C 7 -alkyl or phenyl-C 1 -C 7 -alkyl, and R 1 can also be C 8 -C 16 -alkanoyl; and a pharmaceutically acceptable carrier.
Claim 2
Dependent Claim
107 words
A pharmaceutical preparation for the treatment of a liver disease comprising a therapeutically effective amount of a compound of the formula ##STR5## wherein R' is hydrogen, halogen, or C 1 -C 7 alkylbenzyl; R" is C 1 -C 7 -alkyl which is substituted by hydroxy-imino; C 2 -C 7 -alkenyl substituted by acetoxymethylthio; C 1 -C 7 -alkylbenzyl; formyl; or trifluoroacetyl; and R 1 , R 2 , R 3 , R 4 , and R 5 are each hydrogen, C 1 -C 7 -alkyl or phenyl-C 1 -C 7 -alkyl, and R 1 can also be C 8 -C 16 -alkanoyl; and a pharmaceutically acceptable carrier.
Claim 3
Dependent Claim
83 words
A pharmaceutical preparation for the treatment of a venous disease comprising a therapeutically effective amount of a compound of the formula ##STR6## wherein R' is hydrogen, C 1 -C 7 alkylbenzyl, or halobenzyl; R" is C 1 -C 4 -alkyl-benzyl, halobenzyl, or carboxyl; and R 1 , R 2 , R 3 , R 4 and R 5 are each hydrogen, C 1 -C 7 -alkyl or phenyl-C 1 -C 7 -alkyl; or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Claim 4
Dependent Claim
83 words
A pharmaceutical preparation for the treatment of a venous disease comprising a therapeutically effective amount of a compound of the formula ##STR6## wherein R' is hydrogen, C 1 -C 7 alkylbenzyl, or halobenzyl; R" is C 1 -C 4 -alkyl-benzyl, halobenzyl, or carboxyl; and R 1 , R 2 , R 3 , R 4 and R 5 are each hydrogen, C 1 -C 7 -alkyl or phenyl-C 1 -C 7 -alkyl; or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.
Claim 5
Dependent Claim
36 words
A pharmaceutical preparation for the treatment of a venous disease comprising a therapeutically effective amount of a compound selected from 8-(4-N,N-dimethylaminobenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol, 6,8-di-(1-piperidyl-methyl)-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, 6,8-di[phenyl-(1-piperidyl-methyl)]-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, 8-formyl-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, 8-formyl-3-O-formyl-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, or a therapeutically active salt thereof and a pharmaceutically acceptable carrier.
Claim 6
Dependent Claim
36 words
A pharmaceutical preparation for the treatment of a venous disease comprising a therapeutically effective amount of a compound selected from 8-(4-N,N-dimethylaminobenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol, 6,8-di-(1-piperidyl-methyl)-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, 6,8-di[phenyl-(1-piperidyl-methyl)]-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, 8-formyl-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, 8-formyl-3-O-formyl-3',4'-O,O-diphenylmethylene-(+)-cyanidan-3-ol, or a therapeutically active salt thereof and a pharmaceutically acceptable carrier.
Claim 7
Dependent Claim
33 words
A pharmaceutical preparation for the treatment of a venous disease comprising a therapeutically effective amount of a compound selected from 8-(4-methylbenzyl)-(+)-cyanidan-3-ol, 8-(2-methylbenzyl)-(+)-cyanidan-3-ol, 6,8-di(2-methylbenzyl)-(+)-cyanidan-3-ol, 8-(4-fluorobenzyl)-(+)-cyanidan-3-ol, 8-(4-methoxybenzyl)-(+)-cyanidan-3-ol, 8-benzyl-3-O-methyl-(+)-cyanidan-3-ol, 8-(4-fluorobenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol, 8-(4-methylbenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol, and a pharmaceutically acceptable carrier.
Claim 8
Dependent Claim
33 words
A pharmaceutical preparation for the treatment of a venous disease comprising a therapeutically effective amount of a compound selected from 8-(4-methylbenzyl)-(+)-cyanidan-3-ol, 8-(2-methylbenzyl)-(+)-cyanidan-3-ol, 6,8-di(2-methylbenzyl)-(+)-cyanidan-3-ol, 8-(4-fluorobenzyl)-(+)-cyanidan-3-ol, 8-(4-methoxybenzyl)-(+)-cyanidan-3-ol, 8-benzyl-3-O-methyl-(+)-cyanidan-3-ol, 8-(4-fluorobenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol, 8-(4-methylbenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol, and a pharmaceutically acceptable carrier.
Claim 9
Dependent Claim
16 words
Pharmaceutical preparation for the treatment of liver diseases which contains 8-formyl-3-O-palmitoyl-(+)-cyanidan-3-ol and a pharmaceutically acceptable carrier.
Claim 10
Dependent Claim
16 words
Pharmaceutical preparation for the treatment of liver diseases which contains 8-formyl-3-O-palmitoyl-(+)-cyanidan-3-ol and a pharmaceutically acceptable carrier.
Claim 11
Dependent Claim
15 words
Pharmaceutical preparation for the treatment of venous diseases according to claim 69 which contains 8-(4-methylbenzyl)-(+)-cyanidan-3-ol.
Claim 12
Dependent Claim
15 words
Pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 8-(2-methylbenzyl)-(+)-cyanidan-3-ol.
Claim 13
Dependent Claim
15 words
Pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 6,8-di-(2-methylbenzyl)-(+)-cyanidan-3-ol.
Claim 14
Dependent Claim
16 words
A pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 8-(4-fluorobenzyl)-(+)-cyanidan-3-ol.
Claim 15
Dependent Claim
16 words
A pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 8-(4-methoxybenzyl)-(+)-cyanidan-3-ol.
Claim 16
Dependent Claim
16 words
A pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 8-benzyl-3-O-methyl-(+)-cyanidan-3-ol.
Claim 17
Dependent Claim
16 words
A pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 8-(4-fluorobenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol.
Claim 18
Dependent Claim
16 words
A pharmaceutical preparation for the treatment of venous diseases according to claim 4 which contains 8-(4-methylbenzyl)-3,5,7,3',4'-penta-O-methyl-(+)-cyanidan-3-ol.
Claim 19
Dependent Claim
17 words
A pharmaceutical preparation for the treatment of liver diseases which contains 8-formyl-3-O-palmitoyl-5,7,3',4'-tetra-O-benzyl-(+)-cyanidan-3-ol and a pharmaceutically acceptable carrier.
Claim 20
Dependent Claim
17 words
A pharmaceutical preparation for the treatment of liver diseases which contains 8-formyl-3-O-palmitoyl-5,7,3',4'-tetra-O-benzyl-(+)-cyanidan-3-ol and a pharmaceutically acceptable carrier.
References Cited (Backward Citations)
US4166861A
Cited
US4255336A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-02-16 | 1990-08-18 | 1991-02-17 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-02-16 | 1994-08-18 | 1995-02-17 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-02-16 | 1998-08-18 | 1999-02-17 | $7700.00 | Window Closed / Lapsed |