US5055458A
Expired / Lapsed
US
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Purine derivatives having antiviral activity
Assignee: Beecham Group PLC
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Filing: 1989-07-28
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Granted: 1991-10-08
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Expires: 2009-07-28
Abstract
Abstract Compounds of formula (I) and pharmaceutically acceptable salts thereof: ##STR1## wherein R 1 is hydroxy, amino, chloro or OR 7 wherein R 7 is C 1-6 alkyl, phenyl or phenyl C 1-2 alkyl either of which phenyl moieties may be substituted by one or two substituents selected from halo, C 1-4 alkyl or C 1-4 alkoxy; R 2 amino or, when R 1 is hydroxy or amino, R 2 may also be hydrogen; X is --CH 2 CH 2 -- or a moiety of structure (a), (b) or (c): ##STR2## wherein n is 1 or 2; m is 0, 1 or 2; and R 3 is hydrogen or acyl; R 4 is a group of formula: ##STR3## wherein R 5 and R 6 are independently selected from hydrogen, C 1-6 alkyl and optionally substituted phenyl; having antiviral activity, processes for their preparation and their use as pharmaceuticals.
Inventors
- 👤 Stuart Bailey
- 👤 Michael R. Harnden
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 09:33
CPC Classifications
C; C07; C07D; C07D473/00; C07D473/02; C07F; C07F9/00; C07F9/02; C07F9/547; C07F9/6561; C07F9/65616; A; A61; A61P; A61P31/00; A61P31/12; A61P35/00; C07F9/28; C07F9/38; C07F9/40; C07F9/4003; C07F9/4006; C07F9/645; C07F9/6503; C07F9/6506; C07F9/6509; C07F9/6512
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
183 words
A compound of formula (I), or a pharmaceutically acceptable salt thereof: ##STR40## wherein R 1 is hydroxy, amino, chloro or OR 7 wherein R 7 is C 1-6 alkyl, phenyl C 1-2 alkyl either of which phenyl moieties may be substituted by one or two substituents selected from halo, C 1-4 alkyl or C 1-4 alkoxy; R 2 is amino or, when R 1 is hydroxy or amino, R 2 may also be hydrogen; X is --CH 2 CH 2 -- or a moiety of structure (a), (b) or (c): ##STR41## wherein n is 1 or 2; m is 0, 1 or 2; and R 3 is hydrogen or C 1-7 alkanoyl or benzoyl optionally substituted in the phenyl ring by one, two or three groups or atoms selected from halogen, C 1-4 alkyl and C 1-4 alkoxy; R 4 is a group of formula: ##STR42## wherein R 5 and R 6 are independently selected from hydrogen, C 1-6 alkyl and phenyl or phenyl substituted by one, two or three groups or atoms selected from halogen, C 1-4 alkyl and C 1-4 alkoxy.
Claim 2
Dependent Claim
183 words
A compound of formula (I), or a pharmaceutically acceptable salt thereof: ##STR40## wherein R 1 is hydroxy, amino, chloro or OR 7 wherein R 7 is C 1-6 alkyl, phenyl C 1-2 alkyl either of which phenyl moieties may be substituted by one or two substituents selected from halo, C 1-4 alkyl or C 1-4 alkoxy; R 2 is amino or, when R 1 is hydroxy or amino, R 2 may also be hydrogen; X is --CH 2 CH 2 -- or a moiety of structure (a), (b) or (c): ##STR41## wherein n is 1 or 2; m is 0, 1 or 2; and R 3 is hydrogen or C 1-7 alkanoyl or benzoyl optionally substituted in the phenyl ring by one, two or three groups or atoms selected from halogen, C 1-4 alkyl and C 1-4 alkoxy; R 4 is a group of formula: ##STR42## wherein R 5 and R 6 are independently selected from hydrogen, C 1-6 alkyl and phenyl or phenyl substituted by one, two or three groups or atoms selected from halogen, C 1-4 alkyl and C 1-4 alkoxy.
Claim 3
Dependent Claim
26 words
A compound according to claim 1 wherein R 1 is hydroxy and R 2 is amino, or R 1 is amino and R 2 is hydrogen.
Claim 4
Dependent Claim
14 words
A compound according to claim 1 wherein X is --CH 2 CH 2 --.
Claim 5
Dependent Claim
21 words
A compound according to claim 1 wherein X is of structure (a) as defined in claim 1, and n is 1.
Claim 6
Dependent Claim
15 words
A compound according to claim 1 wherein R 5 and R 6 are both hydrogen.
Claim 7
Dependent Claim
10 words
A compound selected from the group consisting of: 9-[3-(diethoxyphosphorylmethoxy)propoxy]guanine, 9-[3-(phosphonomethoxy)propoxy]guanine,
Claim 8
Dependent Claim
10 words
A compound selected from the group consisting of: 9-[3-(diethoxyphosphorylmethoxy)propoxy]guanine, 9-[3-(phosphonomethoxy)propoxy]guanine,
Claim 9
Dependent Claim
26 words
6-diamino-9-[3-(diethoxyphosphorylmethoxy)propoxy]purine, 2,6-diamino-9-[3-(phosphonomethoxy)propoxy]purine, 9-[3-(diethoxyphosphorylmethoxy)propoxy]adenine, 9-[3-(phosphonomethoxy)propoxy]adenine, 9-[3-(ethoxy(hydroxy)phosphorylmethoxy)propoxy]guanine, 2,6-diamino-9-[(3-diethoxyphosphorylmethoxy-2-hydroxymethyl)propoxy]purine, 2,6-diamino-9-[(2-hydroxymethyl-3-phosphonomethoxy)propoxy]purine, 9-[(3-diethoxyphosphorylmethoxy-2-hydroxymethyl)propoxy]guanine, 9-[(2-hydroxymethyl-3-phosphonomethoxy)propoxy]guanine, 9-[(3-diethoxyphosphorylmethoxy-2-hydroxymethyl)propoxy]adenine, 9-[(2-hydroxymethyl-3-phosphonomethoxy)propoxy]adenine, 9-[(3-ethoxy(hydroxy)phosphorylmethoxy-2-hydroxymethyl)propoxy]guanine, 9-(1-diethoxyphosphorylmethoxy-3-hydroxyprop-2-oxy)guanine, 9-(1-hydroxy-3-phosphonomethoxyprop-2-oxy)guanine, 9-(1-diethoxyphosphorylmethoxy-3-hydroxyprop-2-oxy)adenine, 9-(1-hydroxy-3-phosphonomethoxyprop-2-oxy)adenine, 2,6-diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purine, 2,6-diamino-9-[1-hydroxy-3-(phosphonomethoxy)prop-2-oxy]purine, 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]guanine, 9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy]adenine, 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]adenine, 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine, 9-[1-hydroxy-4-(phosphonomethoxy)but-2-oxy]guanine, 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]adenine and 9-[1-hydroxy-4-(phosphonomethoxy)but-2-oxy]adenine.
Claim 10
Dependent Claim
26 words
6-diamino-9-[3-(diethoxyphosphorylmethoxy)propoxy]purine, 2,6-diamino-9-[3-(phosphonomethoxy)propoxy]purine, 9-[3-(diethoxyphosphorylmethoxy)propoxy]adenine, 9-[3-(phosphonomethoxy)propoxy]adenine, 9-[3-(ethoxy(hydroxy)phosphorylmethoxy)propoxy]guanine, 2,6-diamino-9-[(3-diethoxyphosphorylmethoxy-2-hydroxymethyl)propoxy]purine, 2,6-diamino-9-[(2-hydroxymethyl-3-phosphonomethoxy)propoxy]purine, 9-[(3-diethoxyphosphorylmethoxy-2-hydroxymethyl)propoxy]guanine, 9-[(2-hydroxymethyl-3-phosphonomethoxy)propoxy]guanine, 9-[(3-diethoxyphosphorylmethoxy-2-hydroxymethyl)propoxy]adenine, 9-[(2-hydroxymethyl-3-phosphonomethoxy)propoxy]adenine, 9-[(3-ethoxy(hydroxy)phosphorylmethoxy-2-hydroxymethyl)propoxy]guanine, 9-(1-diethoxyphosphorylmethoxy-3-hydroxyprop-2-oxy)guanine, 9-(1-hydroxy-3-phosphonomethoxyprop-2-oxy)guanine, 9-(1-diethoxyphosphorylmethoxy-3-hydroxyprop-2-oxy)adenine, 9-(1-hydroxy-3-phosphonomethoxyprop-2-oxy)adenine, 2,6-diamino-9-[1-(diethoxyphosphorylmethoxy)-3-hydroxyprop-2-oxy]purine, 2,6-diamino-9-[1-hydroxy-3-(phosphonomethoxy)prop-2-oxy]purine, 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]guanine, 9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy]adenine, 9-[2-hydroxy-3-(phosphonomethoxy)propoxy]adenine, 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine, 9-[1-hydroxy-4-(phosphonomethoxy)but-2-oxy]guanine, 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]adenine and 9-[1-hydroxy-4-(phosphonomethoxy)but-2-oxy]adenine.
Claim 11
Dependent Claim
39 words
A pharmaceutical composition for use in treating viral infections caused by viruses selected from the group consisting of lentiviruses, varicella-zoster virus, and cytomegalovirus comprising an effective amount of a compound according to claim 1 and a pharmaceutically acceptable carrier.
Claim 12
Dependent Claim
45 words
A method of treatment of viral infections caused by viruses selected from the group consisting of lentiviruses, varicella-zoster virus, and cytomegalovirus in mammals, which comprises the administration to the mammal in need of such treatment, an effective amount of a compound according to claim 1.
Claim 13
Dependent Claim
3 words
The compound 9-(1-Hydroxy-3-phosphonomethoxyprop-2-oxy)guanine.
Claim 14
Dependent Claim
3 words
The compound 9-(1-Hydroxy-3-phosphonomethoxyprop-2-oxy)guanine.
Claim 15
Dependent Claim
26 words
A method of treatment of cytomegalovirus infections in mammals comprising the administration to a mammal of an effective amount of the compound according to claim 9.
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