Patent JPH05242542A successfully refreshed from Google Patents.
Patent US4556659A successfully refreshed from Google Patents.
US4556659A
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Substituted 9-(1-0- or 3-0-monosubstituted or 1,3-Di-0-substituted propoxymethyl)-purines as antiviral agents
Assignee: Syntex USA LLC
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Filing: 1982-08-09
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Granted: 1985-12-03
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Expires: 2002-08-09
Abstract
Abstract Compounds useful as antiviral agents are defined by the following formula: <IMAGE> (I) wherein R1 is hydrogen, -C(Y)OR7 or -C(O)NHR7 wherein R7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R2 is -C(Y)OR7 or -C(O)NHR7 wherein R7 is as defined above; Y is oxygen or sulfur; R3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR9R10 wherein R9 and R10 are independently hydrogen or lower alkyl of one to six carbon atoms or -NHC(O)R8 wherein R8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, -NR9R10 wherein R9 and R10 are as defined above or -NHC(O)R8 wherein R8 is as defined above and R4 together with R5 is a bond; or (b) R5 together with R6 is a keto group and R4 is hydrogen.
Inventors
- 👤 Julien P. H. Verheyden
- 👤 John C. Martin
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 17:00
CPC Classifications
C; C07; C07D; C07D473/00; C07D473/40; A; A61; A61P; A61P31/00; A61P31/12; C07C; C07C43/00; C07C43/02; C07C43/03; C07C43/14; C07C43/17; C07C43/174; C07C43/1745; C07C43/178; C07C43/1785; C07D473/26; C07D473/32; C07D473/34
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
190 words
A compound of the formula ##STR7## wherein R 1 is hydrogen, --C(Y) OR 7 or --C(O)NHR 7 wherein R 7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R 2 is --C(Y)OR 7 or --C(O)NHR 7 wherein R 7 is as defined above; Y is oxygen or sulfur; R 3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR 9 R 10 wherein R 9 and R 10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R 8 wherein R 8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R 6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR 9 R 10 wherein R 9 and R 10 are as defined above or -NHC(O)R 8 wherein R 8 is as defined above and R 4 together with R 5 is a bond; or (b) R 5 together with R 6 is a keto group and R 4 is hydrogen.
Claim 2
Dependent Claim
190 words
A compound of the formula ##STR7## wherein R 1 is hydrogen, --C(Y) OR 7 or --C(O)NHR 7 wherein R 7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R 2 is --C(Y)OR 7 or --C(O)NHR 7 wherein R 7 is as defined above; Y is oxygen or sulfur; R 3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR 9 R 10 wherein R 9 and R 10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R 8 wherein R 8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R 6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR 9 R 10 wherein R 9 and R 10 are as defined above or -NHC(O)R 8 wherein R 8 is as defined above and R 4 together with R 5 is a bond; or (b) R 5 together with R 6 is a keto group and R 4 is hydrogen.
Claim 3
Dependent Claim
44 words
A compound of claim 1 wherein R 3 is hydrogen or amino and R 6 is hydrogen, thio or NH 2 and R 4 together with R 5 is a bond with the proviso that R 3 and R 6 are not both hydrogen.
Claim 4
Dependent Claim
34 words
A compound of claim 2 wherein R 3 is hydrogen, R 4 together with R 5 is a bond, R 6 is amino, R 1 and R 2 are independently methoxycarbonyl which is 6-amino--[1,3-di(methoxycarbonyloxy)-2-propoxymethyl]purine.
Claim 5
Dependent Claim
21 words
A compound of claim 1 of the formula ##STR8## wherein R 1 and R 2 are as defined in claim 1.
Claim 6
Dependent Claim
23 words
A compound of claim 4 wherein R 1 and R 2 are --C(O)OR 7 wherein R 7 is as defined in claim 1.
Claim 7
Dependent Claim
17 words
A compound of claim 5 wherein R 1 and R 2 are independently methoxycarbonyl which is 9-[1,3-di(methoxycarbonyloxy)-2-propoxymethyl]guanine.
Claim 8
Dependent Claim
17 words
A compound of claim 5 wherein R 1 and R 2 are independently n-butoxycarbonyl which is 9-[1,3-di(n-butoxycarbonyloxy)-2-propoxymethyl]guanine.
Claim 9
Dependent Claim
17 words
A compound of claim 5 wherein R 1 and R 2 are independently t-butoxycarbonyl which is 9-[1,3-di(t-butoxycarbonyloxy)-2-propoxymethyl]guanine.
Claim 10
Dependent Claim
18 words
A compound of claim 5 wherein R 1 and R 2 are independently n-octyloxycarbonyl which is 9-[1,3-di(n-octyloxycarbonyloxy)-2-propoxymethyl] guanine.
Claim 11
Dependent Claim
17 words
A compound of claim 5 wherein R 1 and R 2 are independently cyclopentyloxycarbonyl which is 9-[1,3-di(cyclopentyloxycarbonyloxy)-2-propoxymethyl]guanine.
Claim 12
Dependent Claim
17 words
A compound of claim 5 wherein R 1 and R 2 are independently benzyloxycarbonyl which is 9-[1,3-di-(benzyloxycarbonyloxy)-2-propoxymethyl]guanine.
Claim 13
Dependent Claim
25 words
A compound of claim 4 wherein R 1 is hydrogen and R 2 is -C(O)OR 7 wherein R 7 is as defined in claim 1.
Claim 14
Dependent Claim
18 words
A compound of claim 12 wherein R 1 is hydrogen and R 2 is methoxycarbonyl which is 9-(1-hydroxy-3-methoxycarbonyloxy-2-propoxymethyl)guanine.
Claim 15
Dependent Claim
18 words
A compound of claim 12 wherein R 1 is hydrogen and R 2 is n-butoxycarbonyl which is 9-(1-hydroxy--n-butoxycarbonyloxy-2-propoxymethyl)guanine.
Claim 16
Dependent Claim
18 words
A compound of claim 12 wherein R 1 is hydrogen and R 2 is n-octyloxycarbonyl which is 9-(1-hydroxy--n-octyloxycarbonyloxy-2-propoxymethyl)guanine.
Claim 17
Dependent Claim
18 words
A compound of claim 12 wherein R 1 is hydrogen and R 2 is cyclopentyloxycarbonyl which is 9-(1-hydroxy-3-cyclopentyloxycarbonyloxy-2-propoxymethyl)guanine.
Claim 18
Dependent Claim
18 words
A compound of claim 12 wherein R 1 is hydrogen and R 2 is benzyloxycarbonyloxy which is 9-(1-hydroxy-3-benzyloxycarbonyloxy-2-propoxymethyl)guanine.
Claim 19
Dependent Claim
23 words
A compound of claim 4 wherein R 1 and R 2 are --C(S)OR 7 wherein R 7 is as defined in claim 1.
Claim 20
Dependent Claim
23 words
A compound of claim 4 wherein R 1 and R 2 are --C(O)NHR 7 wherein R 7 is as defined in claim 1.
Claim 21
Dependent Claim
17 words
A compound of claim 19 wherein R 1 and R 2 are independently ethylaminocarbonyl which is 9-[1,3-di(ethylaminocarbonyloxy)-2-propoxymethyl]guanine.
Claim 22
Dependent Claim
200 words
An antiviral pharmaceutical composition which comprises a pharmaceutically acceptable carrier and a compound of the formula ##STR9## wherein R 1 is hydrogen, -C(Y)OR 7 or -C(O)NHR 7 wherein R 7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R 2 is --C(Y)OR 7 or --C(O)NHR 7 wherein R 7 is as defined above; Y is oxygen or sulfur; R 3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR 9 R 10 wherein R 9 and R 10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R 8 wherein R 8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R 6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR 9 R 10 wherein R 9 and R 10 are as defined above or --NHC(O)R 8 wherein R 8 is as defined above and R 4 together with R 5 is a bond; or (b) R 5 together with R 6 is a keto group and R 4 is hydrogen.
Claim 23
Dependent Claim
200 words
An antiviral pharmaceutical composition which comprises a pharmaceutically acceptable carrier and a compound of the formula ##STR9## wherein R 1 is hydrogen, -C(Y)OR 7 or -C(O)NHR 7 wherein R 7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R 2 is --C(Y)OR 7 or --C(O)NHR 7 wherein R 7 is as defined above; Y is oxygen or sulfur; R 3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR 9 R 10 wherein R 9 and R 10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R 8 wherein R 8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R 6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR 9 R 10 wherein R 9 and R 10 are as defined above or --NHC(O)R 8 wherein R 8 is as defined above and R 4 together with R 5 is a bond; or (b) R 5 together with R 6 is a keto group and R 4 is hydrogen.
Claim 24
Dependent Claim
32 words
An antiviral pharmaceutical composition of claim 21 which comprises a pharmaceutically acceptable carrier and a compound of the formula ##STR10## wherein R 1 and R 2 are as defined in claim 21.
Claim 25
Independent Claim
215 words
A method of treating a viral infection in a warm blooded or cold blooded animal having a viral infection which comprises administering an effective amount of a compound of the formula ##STR11## wherein R 1 is hydrogen, --C(Y)OR 7 or --C(O)NHR 7 wherein R 7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R 2 is --C(Y)OR 7 or -C(O)NHR 7 wherein R 7 is as defined above; Y is oxygen or sulfur; R 3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR 9 R 10 wherein R 9 and R 10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R 8 wherein R 8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R 6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR 9 R 10 wherein R 9 and R 10 are as defined above or --NHC(O)R 8 wherein R 8 is as defined above and R 4 together with R 5 is a bond; or (b) R 5 together with R 6 is a keto group and R 4 is hydrogen.
Claim 26
Independent Claim
215 words
A method of treating a viral infection in a warm blooded or cold blooded animal having a viral infection which comprises administering an effective amount of a compound of the formula ##STR11## wherein R 1 is hydrogen, --C(Y)OR 7 or --C(O)NHR 7 wherein R 7 is alkyl of one to twelve carbon atoms, alkenyl of two to twelve carbon atoms, cyclopentyl, cyclohexyl, phenyl or benzyl; R 2 is --C(Y)OR 7 or -C(O)NHR 7 wherein R 7 is as defined above; Y is oxygen or sulfur; R 3 is hydrogen, halo, thio, lower alkylthio of one to six carbon atoms, azido, NR 9 R 10 wherein R 9 and R 10 are independently hydrogen or lower alkyl of one to six carbon atoms or --NHC(O)R 8 wherein R 8 is hydrogen, alkyl of one to nineteen carbon atoms or 1-adamantyl; and (a) R 6 is hydrogen, halo, lower alkoxy of one to six carbon atoms, azido, thio, lower alkylthio of one to six carbon atoms, --NR 9 R 10 wherein R 9 and R 10 are as defined above or --NHC(O)R 8 wherein R 8 is as defined above and R 4 together with R 5 is a bond; or (b) R 5 together with R 6 is a keto group and R 4 is hydrogen.
Claim 27
Dependent Claim
20 words
A method according to claim 23 of treating a viral infection in a warm blooded animal having a viral infection.
Claim 28
Dependent Claim
20 words
A method according to claim 23 of treating a viral infection in a cold blooded animal having a viral infection.
Claim 29
Dependent Claim
30 words
A method of claim 23 which comprises administering an effective amount of a compound of the formula ##STR12## wherein R 1 and R 2 are as defined in claim 23.
Claim 30
Dependent Claim
20 words
A method according to claim 26 of treating a viral infection in a warm blooded animal having a viral infection.
Claim 31
Dependent Claim
20 words
A method according to claim 26 of treating a viral infection in a cold blooded animal having a viral infection.
References Cited (Backward Citations)
US4199574A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1988-12-02 | 1989-06-03 | 1989-12-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-12-02 | 1993-06-03 | 1993-12-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-12-02 | 1997-06-03 | 1997-12-03 | $7700.00 | Window Closed / Lapsed |