US4755516A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Antiviral compounds
Assignee: Merck and Co Inc
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Filing: 1987-04-06
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Granted: 1988-07-05
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Expires: 2007-04-06
Abstract
Abstract 4-(Guanin-9-yl)butanals and their 3-oxa, 3-thia, and 2-ene counterparts and derivatives thereof, wherein the aldehyde is protected, which have antiviral activity, and are useful in treating viral infections, particularly herpes viral infections, such as herpes simplex viral infections, in mammals (especially humans), birds or fish.
Inventors
- 👤 Richard L. Tolman
- 👤 Wallace T. Ashton
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 15:27
CPC Classifications
C; C07; C07D; C07D473/00; C07D317/00; C07D317/08; C07D317/10; C07D317/14; C07D317/18; C07D317/24; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
236 words
A compound of the formula: ##STR17## and the pharmaceutically acceptable salts thereof wherein W is --OCH 2 --, --CH 2 CH 2 --, --SCH 2 -- or --CH═CH--; X is ##STR18## wherein M + is a pharmaceutically acceptable alkali metal cation; ═NOR 1 ; NR 3 ; ##STR19## wherein Y is O, S or NH.HA wherein HA is a pharmaceutically acceptable inorganic or organic strong acid; ##STR20## wherein each Z is independently O, S or NR 1 and R 4 is R 2 or the two R 4 s taken together with the Z moieties to which they are attached form a group ##STR21## wherein n is 2 or 3; each R 1 is independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, phenyl substituted with halo, with alkyl having 1 to 4 carbon atoms or with alkoxy having 1 to 4 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, or ##STR22## each R 2 is independently alkyl having 1 to 6 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, phenyl, phenyl substituted with halo, with alkyl having 1 to 4 carbon atoms or with alkoxy having 1 to 4 carbon atoms; each R 3 is independently selected from phenyl, phenyl substituted with halo, phenyl substituted with alkyl having 1 to 4 carbon atoms or phenyl substituted with alkoxy having 1 to 4 carbon atoms.
Claim 2
Dependent Claim
236 words
A compound of the formula: ##STR17## and the pharmaceutically acceptable salts thereof wherein W is --OCH 2 --, --CH 2 CH 2 --, --SCH 2 -- or --CH═CH--; X is ##STR18## wherein M + is a pharmaceutically acceptable alkali metal cation; ═NOR 1 ; NR 3 ; ##STR19## wherein Y is O, S or NH.HA wherein HA is a pharmaceutically acceptable inorganic or organic strong acid; ##STR20## wherein each Z is independently O, S or NR 1 and R 4 is R 2 or the two R 4 s taken together with the Z moieties to which they are attached form a group ##STR21## wherein n is 2 or 3; each R 1 is independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, phenyl substituted with halo, with alkyl having 1 to 4 carbon atoms or with alkoxy having 1 to 4 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, or ##STR22## each R 2 is independently alkyl having 1 to 6 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, phenyl, phenyl substituted with halo, with alkyl having 1 to 4 carbon atoms or with alkoxy having 1 to 4 carbon atoms; each R 3 is independently selected from phenyl, phenyl substituted with halo, phenyl substituted with alkyl having 1 to 4 carbon atoms or phenyl substituted with alkoxy having 1 to 4 carbon atoms.
Claim 3
Dependent Claim
26 words
A compound according to claim 1, wherein W is --OCH 2 -- or --CH 2 CH 2 -- and X is as defined in claim 1.
Claim 4
Dependent Claim
219 words
A compound according to claim 2, wherein X is ##STR23## wherein M + is a pharmaceutically-acceptable alkali metal cation; ═NOR 1 ; ═NR 3 ; ##STR24## wherein Y is O or NH.HA wherein HA is hydrochloric acid, formic acid or phosphoric acid; inorganic or organic strong acid; ##STR25## wherein each Z is independently O, S or NR 1 and R 4 is R 2 or the two R 4 s taken together with the Z moieties to which they are attached form a group ##STR26## wherein n is 2 or 3; each R 1 is independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, phenyl substituted with halo, phenyl substituted with alkyl having 1 to 4 carbon atoms, phenyl substituted with alkoxy having 1 to 4 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, or ##STR27## each R 2 is independently alkyl having 1 to 6 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, phenyl, phenyl substituted with halo, with alkyl having 1 to 4 carbon atoms or with alkoxy having 1 to 4 carbon atoms; each R 3 is selected from phenyl, phenyl substituted with halo, phenyl substituted with alkyl having 1 to 4 carbon atoms or phenyl substituted with alkoxy having 1 to 4 carbon atoms.
Claim 5
Dependent Claim
232 words
A compound according to claim 3, wherein X is ##STR28## wherein M + is a pharmaceutically-acceptable alkali metal cation; ═NOR 1 ; ##STR29## wherein Y is O or NH.HA wherein HA is hydrochloric acid, formic acid or phosphoric acid; ##STR30## wherein each Z is independently O or NR 1 and R 4 is alkyl of 1 to 6 carbon atoms or alkoxyalkyl of 1 to 6 carbon atoms or the two R 4 s taken together with the Z moieties to which they are attached form a group ##STR31## wherein Z is S, O or NR 1 and n is 2 or 3; each R 1 is independently hydrogen, alkyl having 1 to 6 carbon atoms, phenyl, phenyl substituted with halo, phenyl substituted with alkyl having 1 to 4 carbon atoms, phenyl substituted with alkoxy having 1 to 4 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, or ##STR32## each R 2 is independently alkyl having 1 to 6 carbon atoms, phenylalkyl wherein the alkyl moiety has 1 to 4 carbon atoms, phenyl or phenyl substituted with halo, with alkyl having 1 to 4 carbon atoms or with alkoxy having 1 to 4 carbon atoms; each R 3 is selected from phenyl, phenyl substituted with halo, phenyl substituted with alkyl having 1 to 4 carbon atoms or phenyl substituted with alkoxy having 1 to 4 carbon atoms.
Claim 6
Dependent Claim
5 words
4-(Guanin-9-yl)-3-oxabutanal, according to claim 1.
Claim 7
Dependent Claim
5 words
4-(Guanin-9-yl)butanal, according to claim 1.
Claim 8
Dependent Claim
19 words
An antiviral pharmaceutical composition comprising an effective amount of a compound according to claim 1 and a pharmaceutically-acceptable carrier.
Claim 9
Dependent Claim
23 words
A method of treating viral infections in mammals, birds or fish comprising administering an effective amount of a compound according to claim 1.
References Cited (Backward Citations)
EP0173624A2
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-07-05 | 1992-01-04 | 1992-07-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-07-05 | 1996-01-04 | 1996-07-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-07-05 | 2000-01-04 | 2000-07-05 | $7700.00 | Window Closed / Lapsed |