US4352792A
Expired / Lapsed
US
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3-Alkoxyflavone antiviral agents
Assignee: Hoffmann La Roche Inc
•
Filing: 1980-04-07
•
Granted: 1982-10-05
•
Expires: 2000-04-07
Abstract
Abstract Antiviral compositions containing 3-alkoxyflavone compounds as their active ingredients are disclosed.
Inventors
- 👤 Hideo Ishitsuka
- 👤 Haruyoshi Shirai
- 👤 Isao Umeda
- 👤 Yasuji Suhara
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 16:27
CPC Classifications
C; C07; C07D; C07D311/00; C07D311/02; C07D311/04; C07D311/22; C07D311/26; C07D311/28; C07D311/30; A; A61; A61P; A61P31/00; A61P31/12
Claims Analysis
Total Claims: 74
Claim 1
Independent Claim
131 words
An anti-enteroviral composition comprising: (a) as an active ingredient a compound of the formula: ##STR5## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-enteroviral agent; and (b) a pharmaceutically acceptable carrier material.
Claim 2
Dependent Claim
131 words
An anti-enteroviral composition comprising: (a) as an active ingredient a compound of the formula: ##STR5## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-enteroviral agent; and (b) a pharmaceutically acceptable carrier material.
Claim 3
Dependent Claim
131 words
An anti-rhinoviral composition comprising: (a) as an active ingredient a compound of the formula: ##STR6## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-rhinoviral agent; and (b) a pharmaceutically acceptable carrier material.
Claim 4
Dependent Claim
131 words
An anti-rhinoviral composition comprising: (a) as an active ingredient a compound of the formula: ##STR6## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-rhinoviral agent; and (b) a pharmaceutically acceptable carrier material.
Claim 5
Dependent Claim
131 words
An anti-influenzaviral composition comprising: (a) as an active ingredient a compound of the formula: ##STR7## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-influenzaviral agent; and (b) a pharmaceutically acceptable carrier material.
Claim 6
Dependent Claim
131 words
An anti-influenzaviral composition comprising: (a) as an active ingredient a compound of the formula: ##STR7## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-influenzaviral agent; and (b) a pharmaceutically acceptable carrier material.
Claim 7
Dependent Claim
13 words
The composition of claim 1, 2 or 3 wherein R 5 is hydroxy.
Claim 8
Dependent Claim
10 words
The composition of claim 4 wherein the compound is 3-ethoxy-4',5-dihydroxy-3',7-dimethoxyflavone.
Claim 9
Dependent Claim
10 words
The composition of claim 4 wherein the compound is 4',5-dihydroxy-3-isopropoxy-3',7-dimethoxyflavone.
Claim 10
Dependent Claim
10 words
The composition of claim 4 wherein the compound is 4',5-dihydroxy-3,3',7-trimethoxyflavone.
Claim 11
Dependent Claim
10 words
The composition of claim 4 wherein the compound is 4'-hydroxy-3,3',5,7-tetramethoxyflavone.
Claim 12
Dependent Claim
10 words
The composition of claim 4 wherein the compound is 4',5-dihydroxy-3,7-dimethoxyflavone.
Claim 13
Dependent Claim
10 words
The composition of claim 4 wherein the compound is 4',5-dihydroxy-2',3,7-trimethoxyflavone.
Claim 14
Dependent Claim
14 words
The composition of claim 1, 2 or 3 wherein R 5 is lower alkoxy.
Claim 15
Dependent Claim
10 words
The composition of claim 11 wherein the compound is 5,7-dihydroxy-3,4'-dimethoxyflavone.
Claim 16
Dependent Claim
10 words
The composition of claim 11 wherein the compound is 3',5-dihydroxy-3,4',7-trimethoxyflavone.
Claim 17
Dependent Claim
10 words
The composition of claim 11 wherein the compound is 5-hydroxy-3,4',7-trimethoxyflavone.
Claim 18
Dependent Claim
14 words
The composition of claim 1, 2 or 3 wherein R 5 is lower alkanoyloxy.
Claim 19
Dependent Claim
10 words
The composition of claim 15 wherein the compound is 4'-acetoxy-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 20
Dependent Claim
10 words
The composition of claim 15 wherein the compound is 5-hydroxy-3,3',7-trimethoxy-4'-(pivaloyloxy)-flavone.
Claim 21
Dependent Claim
10 words
The composition of claim 15 wherein the compound is 5-(isobutyryloxy)-3,3',7-trimethoxy-4'-(pivaloyloxy)-flavone.
Claim 22
Dependent Claim
10 words
The composition of claim 15 wherein the compound is 3,3',7-trimethoxy-4',5-bis-(propionyloxy)-flavone.
Claim 23
Dependent Claim
10 words
The composition of claim 15 wherein the compound is 4',5-diacetoxy-3,3',7-trimethoxyflavone.
Claim 24
Dependent Claim
13 words
The composition of claim 1, 2 or 3 wherein R 5 is aminoacyloxy.
Claim 25
Dependent Claim
10 words
The composition of claim 21 wherein the compound is 5-hydroxy-4'-(L-lysyloxy)-3,3',7-trimethoxyflavone.
Claim 26
Dependent Claim
10 words
The composition of claim 21 wherein the compound is 4'-(L-alanyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 27
Dependent Claim
10 words
The composition of claim 21 wherein the compound is 4'-(L-glutaminyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 28
Dependent Claim
10 words
The composition of claim 21 wherein the compound is 4'-(L-α-glutamyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 29
Dependent Claim
13 words
The composition of claim 1, 2 or 3 wherein R 5 is glycosyloxy.
Claim 30
Dependent Claim
10 words
The composition of claim 26 wherein the compound is 4'-(β-D-glucopyranosyloxy)-5-hydroxy-3,3',7-trimethoxy-flavone.
Claim 31
Dependent Claim
17 words
The composition of claim 1, 2 or 3 wherein R 5 is a hydroxy-substituted dicarboxylic acid residue.
Claim 32
Dependent Claim
10 words
The composition of claim 28 wherein the compound is 4'-(3-carboxy-2,3-dihydroxypropionyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 33
Dependent Claim
13 words
The composition of claim 1, 2 or 3 wherein R 5 is amino.
Claim 34
Dependent Claim
10 words
The composition of claim 30 wherein the compound is 4'-amino-5,7-dihydroxy-3-methoxyflavone.
Claim 35
Dependent Claim
10 words
The composition of claim 30 wherein the compound is 4'-amino-5-hydroxy-3,7-dimethoxyflavone.
Claim 36
Dependent Claim
13 words
The composition of claim 1, 2 or 3 wherein R 5 is nicotinoyloxy.
Claim 37
Dependent Claim
10 words
The composition of claim 33 wherein the compound is 3,3',7-trimethoxy-4',5-bis-(nicotinoyloxy)-flavone.
Claim 38
Dependent Claim
14 words
The composition of claim 1, 2 or 3 wherein R 5 is lower alkoxycarbonyloxy.
Claim 39
Dependent Claim
10 words
The composition of claim 35 wherein the compound is 4',5-bis-(ethoxycarbonyloxy)-3,3',7-trimethoxyflavone.
Claim 40
Dependent Claim
23 words
The composition of claim 1, 2 or 3 wherein compound I amounts to about 0.001% to about 70% by weight of the composition.
Claim 41
Dependent Claim
125 words
A compound of the formula: ##STR8## wherein R 10 is hydroxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 20 is hydroxy or lower alkoxy; R 40 is hydrogen or lower alkoxy; R 50 is hydroxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 60 is lower alkoxy, with the proviso that when R 10 is acetoxy, R 50 is other than acetoxy and with the further proviso that when R 50 is hydroxy, R 60 is other than methoxy; or pharmaceutically acceptable salts thereof.
Claim 42
Dependent Claim
125 words
A compound of the formula: ##STR8## wherein R 10 is hydroxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 20 is hydroxy or lower alkoxy; R 40 is hydrogen or lower alkoxy; R 50 is hydroxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 60 is lower alkoxy, with the proviso that when R 10 is acetoxy, R 50 is other than acetoxy and with the further proviso that when R 50 is hydroxy, R 60 is other than methoxy; or pharmaceutically acceptable salts thereof.
Claim 43
Dependent Claim
10 words
The compound of claim 38 wherein R 50 is hydroxy.
Claim 44
Dependent Claim
6 words
The compound of claim 39, 3-ethoxy-4',5-dihydroxy-3',7-dimethoxyflavone.
Claim 45
Dependent Claim
6 words
The compound of claim 39, 4',5-dihydroxy-3-isopropoxy-3',7-dimethoxyflavone.
Claim 46
Dependent Claim
11 words
The compound of claim 38 wherein R 50 is lower alkanoyloxy.
Claim 47
Dependent Claim
6 words
The compound of claim 42, 4'-acetoxy-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 48
Dependent Claim
6 words
The compound of claim 42, 5-hydroxy-3,3',7-trimethoxy-4'-(pivaloyloxy)-flavone.
Claim 49
Dependent Claim
6 words
The compound of claim 42, 5-(isobutyryloxy)-3,3',7-trimethoxy-4'-(pivaloyloxy)-flavone.
Claim 50
Dependent Claim
6 words
The compound of claim 42, 3,3',7-trimethoxy-4',5-bis-(propionyloxy)-flavone.
Claim 51
Dependent Claim
10 words
The compound of claim 38 wherein R 50 is aminoacyloxy.
Claim 52
Dependent Claim
6 words
The compound of claim 47, 5-hydroxy-4'-(L-lysyloxy)-3,3',7-trimethoxyflavone.
Claim 53
Dependent Claim
6 words
The compound of claim 47, 4'-(L-alanyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 54
Dependent Claim
6 words
The compound of claim 47, 4'-(L-glutaminyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 55
Dependent Claim
6 words
The compound of claim 47, 4'-(L-α-glutamyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 56
Dependent Claim
10 words
The compound of claim 38 wherein R 50 is glycosyloxy.
Claim 57
Dependent Claim
6 words
The compound of claim 52, 4'-(β-D-glucopyranosyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 58
Dependent Claim
14 words
The compound of claim 38 wherein R 50 is a hydroxy-substituted dicarboxylic acid residue.
Claim 59
Dependent Claim
7 words
The compound of claim 54, 4'-(3-carboxy-2,3-dihydroxy propionyloxy)-5-hydroxy-3,3',7-trimethoxyflavone.
Claim 60
Dependent Claim
10 words
The compound of claim 38 wherein R 50 is amino.
Claim 61
Dependent Claim
6 words
The compound of claim 56, 4'-amino-5,7-dihydroxy-3-methoxyflavone.
Claim 62
Dependent Claim
6 words
The compound of claim 56, 4'-amino-5-hydroxy-3,7-dimethoxyflavone.
Claim 63
Dependent Claim
10 words
The compound of claim 38 wherein R 50 is nicotinoyloxy.
Claim 64
Dependent Claim
6 words
The compound of claim 59, 3,3',7-trimethoxy-4',5-bis-(nicotinoyloxy)-flavone.
Claim 65
Dependent Claim
11 words
The compound of claim 38 wherein R 50 is lower alkoxycarbonyloxy.
Claim 66
Dependent Claim
6 words
The compound of claim 61, 4',5-bis-(ethoxycarbonyloxy)-3,3',7-trimethoxyflavone.
Claim 67
Independent Claim
130 words
A method for treating a mammal infected by an enterovirus comprising administering to said mammal a compound of the formula: ##STR9## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-enteroviral agent.
Claim 68
Independent Claim
130 words
A method for treating a mammal infected by an enterovirus comprising administering to said mammal a compound of the formula: ##STR9## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-enteroviral agent.
Claim 69
Independent Claim
130 words
A method for treating a mammal infected by a rhinovirus comprising administering to said mammal a compound of the formula: ##STR10## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-rhinoviral agent.
Claim 70
Independent Claim
130 words
A method for treating a mammal infected by a rhinovirus comprising administering to said mammal a compound of the formula: ##STR10## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-rhinoviral agent.
Claim 71
Independent Claim
130 words
A method for treating a mammal infected by an influenzavirus comprising administering to said mammal a compound of the formula: ##STR11## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-influenzaviral agent.
Claim 72
Independent Claim
130 words
A method for treating a mammal infected by an influenzavirus comprising administering to said mammal a compound of the formula: ##STR11## wherein R 1 is hydroxy, lower alkoxy, lower alkanoyloxy, lower alkoxycarbonyloxy or nicotinoyloxy; R 2 is hydroxy or lower alkoxy; R 3 is hydrogen or lower alkoxy; R 4 is hydrogen, hydroxy or lower alkoxy; R 5 is hydroxy, lower alkoxy, lower alkanoyloxy, aminoacyloxy where its acyloxy group has 2 to 10 carbon atoms, glycosyloxy which is derived from a monosaccharide of 5 to 7 carbon atoms, a hydroxy-substituted dicarboxylic acid residue where its dicarboxylic acid group has 2 to 8 carbon atoms, amino, nicotinoyloxy or lower alkoxycarbonyloxy and R 6 is lower alkoxy, or pharmaceutically acceptable salts thereof, in an amount which is effective as an anti-influenzaviral agent.
Claim 73
Dependent Claim
13 words
The method of claim 63, 64 or 65 wherein the compound is 3-ethoxy-4',5-dihydroxy-3',7-dimethoxyflavone.
Claim 74
Dependent Claim
32 words
The method of claim 66 wherein the compound is administered at a daily dose of about 1 mg. to about 100 mg. of compound per kilogram of body weight of the mammal.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-10-04 | 1986-04-05 | 1986-10-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-10-04 | 1990-04-05 | 1990-10-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-10-04 | 1994-04-05 | 1994-10-05 | $7700.00 | Window Closed / Lapsed |