US4323573A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Adenine derivatives
Assignee: SmithKline Beecham Corp
•
Filing: 1978-02-01
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Granted: 1982-04-06
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Expires: 1998-02-01
Abstract
Abstract Novel 2-amino substituted adenine compounds and their use as antiviral compounds are disclosed. In particular the compound 2-amino-9-(2-hydroxyethoxymethyl) adenine is particularly advantageous as an antiviral in that it has high oral absorption and that upon metabolism in mammals, it has the property of being converted to 9-(2-hydroxyethoxymethyl) guanine which is also a highly active antiviral.
Inventors
- 👤 Howard J. Schaeffer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 02:22
CPC Classifications
C; C07; C07C; C07C323/00; A; A61; A61P; A61P31/00; A61P31/12; C07D; C07D473/00; C07D473/26; C07D473/32; C07D473/34
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
74 words
A compound of the formula (I) ##STR12## wherein R 1 is amino, R 2 is amino X is oxygen or sulphur R 3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl; R 4 is hydrogen, hydroxy or alkyl; R 5 is hydroxy, amino, alkyl, hydroxyalkyl, benzyloxy, benzoyloxymethyl, sulphamoyloxy, phosphate, or acyloxy having 1 to 8 carbon atoms, R 6 is hydrogen or alkyl; or a pharmaceutically acceptable salt thereof.
Claim 2
Dependent Claim
74 words
A compound of the formula (I) ##STR12## wherein R 1 is amino, R 2 is amino X is oxygen or sulphur R 3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl; R 4 is hydrogen, hydroxy or alkyl; R 5 is hydroxy, amino, alkyl, hydroxyalkyl, benzyloxy, benzoyloxymethyl, sulphamoyloxy, phosphate, or acyloxy having 1 to 8 carbon atoms, R 6 is hydrogen or alkyl; or a pharmaceutically acceptable salt thereof.
Claim 3
Dependent Claim
22 words
A pharmaceutical composition for use as an antiviral which comprises an effective antiviral amount of the compound or salt of claim 1.
Claim 4
Dependent Claim
33 words
A method of treating a susceptible virus infection in a mammal which comprises the administration to the infected mammal of an effective, non-toxic antiviral amount of the compound or salt of claim 1.
Claim 5
Dependent Claim
12 words
The compound or salt of claim 1 in which X is oxygen.
Claim 6
Dependent Claim
10 words
The composition of claim 2 in which X is oxygen.
Claim 7
Dependent Claim
10 words
The method of claim 3 in which X is oxygen.
Claim 8
Dependent Claim
13 words
The compound or salt of claim 1 in which R 5 is acetoxy.
Claim 9
Dependent Claim
15 words
The method of claim 3 in which the virus infection is a herpes virus infection.
Claim 10
Dependent Claim
16 words
The compound or salt of claim 1 in which the salt is an acid addition salt.
Claim 11
Dependent Claim
15 words
The compound or salt of claim 1 in which R 5 is hydroxy or phosphate.
Claim 12
Dependent Claim
13 words
The composition of claim 2 in which R 5 is hydroxy or phosphate.
Claim 13
Dependent Claim
13 words
The method of claim 3 in which R 5 is hydroxy or phosphate.
Claim 14
Dependent Claim
1 words
2-amino-9-(2-hydroxyethoxymethyl)adenine.
Claim 15
Dependent Claim
1 words
2-amino-9-(2-hydroxyethoxymethyl)adenine.
Claim 16
Dependent Claim
6 words
A pharmaceutically acceptable salt of 2-amino-9-(2-hydroxyethoxymethyl)adenine.
Claim 17
Dependent Claim
6 words
A pharmaceutically acceptable salt of 2-amino-9-(2-hydroxyethoxymethyl)adenine.
Claim 18
Dependent Claim
14 words
The salt of claim 14 in which the salt is an acid addition salt.
Claim 19
Independent Claim
36 words
The method of treating a susceptible viral infection in a mammal having said viral infection which comprises the administration to said mammal of an effective antiviral non-toxic amount of 2-amino-9-(2-hydroxyethoxymethyl)adenine or a pharmaceutically acceptable salt thereof.
Claim 20
Independent Claim
36 words
The method of treating a susceptible viral infection in a mammal having said viral infection which comprises the administration to said mammal of an effective antiviral non-toxic amount of 2-amino-9-(2-hydroxyethoxymethyl)adenine or a pharmaceutically acceptable salt thereof.
Claim 21
Dependent Claim
14 words
The method of claim 16 in which the administration is oral, parenteral or topical.
Claim 22
Dependent Claim
15 words
The method of claim 16 in which the viral infection is a herpes virus infection.
Claim 23
Dependent Claim
23 words
A pharmaceutical composition comprising an effective antiviral amount of 2-amino-9-(2-hydroxyethoxymethyl)adenine or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier therefore.
Claim 24
Dependent Claim
23 words
A pharmaceutical composition comprising an effective antiviral amount of 2-amino-9-(2-hydroxyethoxymethyl)adenine or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier therefore.
Claim 25
Dependent Claim
15 words
A pharmaceutical composition of claim 19 in a form for oral, parenteral or topical administration.
Claim 26
Dependent Claim
24 words
A pharmaceutical composition for treating a susceptible viral infection comprising an effective antiviral treatment amount of 2-amino-9(2-hydroxyethoxymethyl)adenine together with a pharmacuetically acceptable carrier therefore.
Claim 27
Dependent Claim
24 words
A pharmaceutical composition for treating a susceptible viral infection comprising an effective antiviral treatment amount of 2-amino-9(2-hydroxyethoxymethyl)adenine together with a pharmacuetically acceptable carrier therefore.
Claim 28
Independent Claim
27 words
A method of treating a herpes virus infection in a human which comprises administering to said human an effective anti herpes treatment amount of the compound 2-amino-9-(2-hydroxyethoxymethyl)adenine.
Claim 29
Independent Claim
27 words
A method of treating a herpes virus infection in a human which comprises administering to said human an effective anti herpes treatment amount of the compound 2-amino-9-(2-hydroxyethoxymethyl)adenine.
Claim 30
Dependent Claim
16 words
The method of claim 22 in which the compound is administered in a pharmacuetically acceptable carrier.
Claim 31
Dependent Claim
18 words
The method of claim 18 in which the viral infection is a herpes simplex or herpes zoster infection.
Claim 32
Dependent Claim
19 words
The method of claim 22 in which the herpes virus infection is a herpes simplex or herpes zoster infection.
References Cited (Backward Citations)
US4146715A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-04-05 | 1985-10-05 | 1986-04-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-04-05 | 1989-10-05 | 1990-04-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-04-05 | 1993-10-05 | 1994-04-06 | $7700.00 | Window Closed / Lapsed |