US4579849A
Expired / Lapsed
US
⏱️ 0.0 years remaining
N-alkylguanine acyclonucleosides as antiviral agents
Assignee: Merck and Co Inc
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Filing: 1984-04-06
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Granted: 1986-04-01
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Expires: 2004-04-06
Abstract
Abstract Disclosed are compounds of the formula: <IMAGE> I and the pharmaceutically acceptable salts thereof wherein R1 and R2 are independently alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl or haloalkynyl, each having 1 to 19 carbon atoms, or R2 is hydrogen; R3 is hydrogen, alkyl having 1 to 6 carbon atoms or hydroxyalkyl having 1 to 6 carbon atoms; R4 is hydrogen, halogen, amino or alkyl having 1 to 4 carbon atoms; R5, R6 and R7 are independently selected from hydrogen, hydroxy, alkyl having 1 to 6 carbon atoms, acyloxy having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, acyloxyalkyl having 1 to 12 carbon atoms, amino, alkylamino of 1 to 6 carbon atoms and -PO3=, or two of R5, R6 and R7 taken together form a group -OPO2O--, -CH2OPO2O-+13, -CH2OPO2OPO2O=-, or -OPO2OPO2O=-; A is O, S or CH2and X is a pharmaceutically acceptable anion. The compounds have antiviral activity, especially against viruses of the herpes class.
Inventors
- 👤 Malcolm MacCoss
- 👤 Richard L. Tolman
- 👤 Robert A. Strelitz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 20:24
CPC Classifications
C; C07; C07D; C07D473/00; A; A61; A61P; A61P31/00; A61P31/12; A61P31/20; A61P31/22; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
221 words
A compound of the formula: ##STR4## wherein R 1 and R 2 are independently alkyl or haloalkyl, each having 1 to 12 carbon atoms or alkenyl, haloalkenyl, alkynyl or haloalkynyl, each having 2 to 12 carbon atoms, or R 2 is hydrogen; R 3 is hydrogen, alkyl having 1 to 6 carbon atoms or hydroxyalkyl having 1 to 6 carbon atoms; R 4 is hydrogen, halogen, amino or alkyl having 1 to 4 carbon atoms; R 5 , R 6 and R 7 are independently selected from hydrogen, hydroxy, alkyl having 1 to 6 carbon atoms, acyloxy having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, acyloxyalkyl having 1 to 12 carbon atoms, amino, alkylamino having 1 to 6 carbon atoms and --PO 3 = or two of R 5 , R 6 and R 7 taken together form a group --OPO 2 O - --, --CH 2 OPO 2 O - --, --CH 2 OPO 2 OPO 2 O = --, or --OPO 2 OPO 2 O = --; A is 0, S or CH 2 and X is a pharmaceutically acceptable anion from the group consisting of fluoride, chloride, bromide, iodide, alkanoate having 1 to 6 carbon atoms, alkylsulfonate having 1 to 6 carbon atoms, sulfate and phosphate.
Claim 2
Dependent Claim
221 words
A compound of the formula: ##STR4## wherein R 1 and R 2 are independently alkyl or haloalkyl, each having 1 to 12 carbon atoms or alkenyl, haloalkenyl, alkynyl or haloalkynyl, each having 2 to 12 carbon atoms, or R 2 is hydrogen; R 3 is hydrogen, alkyl having 1 to 6 carbon atoms or hydroxyalkyl having 1 to 6 carbon atoms; R 4 is hydrogen, halogen, amino or alkyl having 1 to 4 carbon atoms; R 5 , R 6 and R 7 are independently selected from hydrogen, hydroxy, alkyl having 1 to 6 carbon atoms, acyloxy having 1 to 8 carbon atoms, alkoxy having 1 to 6 carbon atoms, hydroxyalkyl having 1 to 6 carbon atoms, acyloxyalkyl having 1 to 12 carbon atoms, amino, alkylamino having 1 to 6 carbon atoms and --PO 3 = or two of R 5 , R 6 and R 7 taken together form a group --OPO 2 O - --, --CH 2 OPO 2 O - --, --CH 2 OPO 2 OPO 2 O = --, or --OPO 2 OPO 2 O = --; A is 0, S or CH 2 and X is a pharmaceutically acceptable anion from the group consisting of fluoride, chloride, bromide, iodide, alkanoate having 1 to 6 carbon atoms, alkylsulfonate having 1 to 6 carbon atoms, sulfate and phosphate.
Claim 3
Dependent Claim
13 words
A compound according to claim 1, wherein R 1 is alkyl or alkenyl.
Claim 4
Dependent Claim
55 words
A compound according to claim 1, wherein R 1 and R 2 are methyl, R 3 and R 4 are H, R 5 is H or hydroxymethyl, R 6 is H and R 7 is hydroxyl or hydroxymethyl or, alternately, R 5 and R 7 taken together are --CH 2 OPO 2 O - --.
Claim 5
Dependent Claim
6 words
9-(1,3-Dihydroxy-2-propoxymethyl)-1,7-dimethylguaninium iodide, according to claim 1.
Claim 6
Dependent Claim
6 words
9-(1,3-Dihydroxy-2-propoxymethyl)-1-methyl-7-ethylguaninium iodide, according to claim 1.
Claim 7
Dependent Claim
6 words
9-(1,3-Dihydroxy-2-propoxymethyl)-1-ethyl-7-methylguaninium iodide, according to claim 1.
Claim 8
Dependent Claim
6 words
9-(1,3-Dihydroxy-2-propoxymethyl)-1,7-dimethylguaninium acetate, according to claim 1.
Claim 9
Dependent Claim
6 words
9-(2,3-Dihydroxy-1-propoxymethyl)-1,7-dimethylguaninium iodide, according to claim 1.
Claim 10
Dependent Claim
6 words
9-(2-Hydroxyethoxymethyl)-1,7-dimethylguaninium iodide, according to claim 1.
Claim 11
Dependent Claim
6 words
9-(4-Hydroxybutyl)-1,7-dimethylguaninium iodide, according to claim 1.
Claim 12
Dependent Claim
6 words
9-(4-Hydroxy-3-hydroxymethylbutyl)-1,7-dimethylguaninium iodide, according to claim 1.
Claim 13
Dependent Claim
5 words
9-(2,2-dioxo-1,3,2-dioxaphosphorinan-5-yloxymethyl)-1,7-dimethylguanine, according to claim 1.
Claim 14
Dependent Claim
19 words
An antiviral pharmaceutical composition comprising an effective amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
Claim 15
Dependent Claim
27 words
A method of treating viral infections in mammals comprising administering to patient in need of such treatment an effective amount of a compound according to claim 1.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-03-31 | 1989-09-30 | 1990-04-01 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-03-31 | 1993-09-30 | 1994-04-01 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-03-31 | 1997-09-30 | 1998-04-01 | $7700.00 | Window Closed / Lapsed |