US4058659A
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US
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6,8-Disubstituted purine derivatives of 9-β-D-ribofuranosyl 3',5'-cyclic phosphate
Assignee: Viratek Inc
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Filing: 1975-09-29
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Granted: 1977-11-15
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Expires: 1995-09-29
Abstract
Abstract Compounds of formula ##STR1## wherein X is --NR 1 R 2 , --Cl, --Br or SR; Y is --X, --OH or --NH 2 ; Z is hydrogen or --NH 2 ; and R' is hydrogen or C 1 -C 18 acyl; R being hydrogen, aryl, aralkyl, substituted aryl, substituted aralkyl, or C 1 -C 7 alkyl; and R 1 and R 2 being independently selected from the group consisting of hydrogen, phenyl, C 7 -C 10 aralkyl, C 1 -C 7 alkyl, C 1 -C 10 branched chain alkyl, C 1 -C 7 unsaturated alkyl or lower alkyl joined to form a 5 or 6-membered heterocyclic ring, with the proviso that when one of R 1 and R 2 are hydrogen, the other is not. The compounds variously exhibit phosphodiesterase inhibition, protein kinase activation, positive inotropic effects, adenyl cyclase inhibition and other biological activities.
Inventors
- 👤 Roland K. Robins
- 👤 Dennis A. Shuman
- 👤 Kay H. Boswell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 14:47
CPC Classifications
C; C07; C07H; C07H19/00; C07H19/02; C07H19/04; C07H19/16; C07H19/20
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
159 words
A compound of the structure: ##STR10## wherein Z is hydrogen or --NH 2 ; R' is hydrogen or C 1 -C 18 acyl; X is NR 1 R 2 , Cl, Br, or SR 3 ; Y is SR 4 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, phenyl, C 7 to C 10 aralkyl, saturated or unsaturated straight or branched chain C 1 to C 7 alkyl, or R 1 and R 2 are lower alkyl joined together to form a pyrrolidino or piperidino ring; R 3 is hydrogen, lower alkyl, phenyl, or benzyl; and R 4 is phenyl, C 7 to C 10 aralky, or substituted phenyl and substituted C 7 to C 10 aralkyl wherein the substituents are selected from the group consisting of chloro, bromo, fluoro, methyl, methoxy, or nitro, with the proviso that when one of R 1 or R 2 is hydrogen the other is not.
Claim 2
Dependent Claim
159 words
A compound of the structure: ##STR10## wherein Z is hydrogen or --NH 2 ; R' is hydrogen or C 1 -C 18 acyl; X is NR 1 R 2 , Cl, Br, or SR 3 ; Y is SR 4 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, phenyl, C 7 to C 10 aralkyl, saturated or unsaturated straight or branched chain C 1 to C 7 alkyl, or R 1 and R 2 are lower alkyl joined together to form a pyrrolidino or piperidino ring; R 3 is hydrogen, lower alkyl, phenyl, or benzyl; and R 4 is phenyl, C 7 to C 10 aralky, or substituted phenyl and substituted C 7 to C 10 aralkyl wherein the substituents are selected from the group consisting of chloro, bromo, fluoro, methyl, methoxy, or nitro, with the proviso that when one of R 1 or R 2 is hydrogen the other is not.
Claim 3
Dependent Claim
127 words
A compound according to claim 1 wherein X is NR 1 R 2 ; Y is SR 4 ; R 1 and R 2 are independently selected from the group consisting of hydrogen, phenyl, C 7 to C 10 aralkyl, saturated or unsaturated straight or branched chain C 1 to C 7 alkyl, or R 1 and R 2 are lower alkyl joined together to form a pyrrolidino or piperidion ring; R 4 is phenyl, C 7 to C 10 aralkyl or substituted phenyl and substituted C 7 to C 10 aralkyl wherein the substituents are selected from the group consisting of chloro, bromo, fluoro, methyl, methoxy, or nitro, with the proviso that when one of R 1 or R 2 is hydrogen the other is not.
Claim 4
Dependent Claim
14 words
A compound according to claim 2 wherein Z is hydrogen and R' is hydrogen.
Claim 5
Dependent Claim
41 words
A compound according to claim 2 wherein R 1 and R 2 are independently selected from the group consisting of hydrogen, methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl, n-pentyl, iso-pentyl, neo-pentyl, or n-hexyl; and R 4 is phenyl, p-chlorophenyl, or benzyl.
Claim 6
Dependent Claim
35 words
A compound according to claim 2 wherein R 4 is phenyl, benzyl, or substituted phenyl and substituted benzyl and the substituents are selected from the group consisting of chloro, bromo, fluoro, methyl, methoxy, or nitro.
Claim 7
Dependent Claim
34 words
A compound according to claim 2 wherein Z is hydrogen; R' is hydrogen; X is selected from the group consisting of methylamino, ethylamino, n-propylamino, n-butylamino, n-pentylamino, n-hexylamino; and Y is benzylthio, phenylthio, or p-chlorophenylthio.
Claim 8
Dependent Claim
10 words
A compound according to claim 4 designated 8-benzylthio-6-dimethylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 9
Dependent Claim
11 words
A compound according to claim 4 designated 8-benzylthio-6-diethylamino-9-β-D-ribofuranosylpurine 3', 5'-cyclic phosphate.
Claim 10
Dependent Claim
10 words
A compound according to claim 4 designated 8-benzylthio-6-dipropylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 11
Dependent Claim
10 words
A compound according to claim 4 designated 8-benzylamino-6-n-pentylamino-9-β-D-ribofuranosypurine 3',5'-cyclic phosphate.
Claim 12
Dependent Claim
10 words
A compound according to claim 4 designated 8-benzylthio-6-n-hexylamino-9-βD-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 13
Dependent Claim
10 words
A compound according to claim 4 designated 8-benzylthio-6-methylbutylamino-9-β-D-ribofuranosylpyrine 3',5'-cyclic phosphate.
Claim 14
Dependent Claim
11 words
A compound according to claim 4 designated 8-benzylthio-6-iso-propylamino-9-β-D-ribofuranosylpurine 3', 5'-cyclic phosphate.
Claim 15
Dependent Claim
3 words
8-Benzylthio-6-methylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 16
Dependent Claim
3 words
8-Benzylthio-6-methylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 17
Dependent Claim
3 words
8-Benzylthio-6-ethylamino-9β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 18
Dependent Claim
3 words
8-Benzylthio-6-ethylamino-9β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 19
Dependent Claim
3 words
8-Benzylthio-6-n-propylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 20
Dependent Claim
3 words
8-Benzylthio-6-n-propylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 21
Dependent Claim
3 words
8-Benzylthio-6-n-butylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
Claim 22
Dependent Claim
3 words
8-Benzylthio-6-n-butylamino-9-β-D-ribofuranosylpurine 3',5'-cyclic phosphate.
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) | 1980-11-14 | 1981-05-16 | 1981-11-15 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-11-14 | 1985-05-16 | 1985-11-15 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-11-14 | 1989-05-16 | 1989-11-15 | $7700.00 | Window Closed / Lapsed |