Claims
- 1. A substituted purine of formula (I) ##STR12## wherein X is sulphur or oxygen; R.sup.1 is hydroxy, R.sup.2 is amino; R.sup.3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl; R.sup.4 is hydrogen, hydroxy, or lower alkyl; R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzoyloxy, benzoyloxyalkyl, benzyloxy, sulphamoyloxy, phosphate, carboxypropionyloxy, or acetoxy; R.sup.6 is hydrogen, alkyl, hydroxyalkyl or a pharmaceutically acceptable salt thereof.
- 2. A substituted purine of formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 wherein X is an oxygen atom.
- 3. A substituted purine of formula (I) according to claim 2 wherein R.sup.1 is hydroxy, R.sup.2 is amino; R.sup.3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl or phenyl; R.sup.4 is hydrogen or hydroxy; R.sup.5 is hydrogen, hydroxy, hydroxyalkyl, amino, carboxypropionyloxy, acetoxy, benzyloxy, benzoyloxy, benzoyloxyalkyl, phosphate, or sulphamoyloxy; R.sup.6 is hydrogen, alkyl, or hydroxyalkyl; or a pharmaceutically acceptable salt thereof.
- 4. A substituted purine of formula (I) according to claim 2 wherein R.sup.1 is hydroxy; R.sup.2 is amino; R.sup.5 is hydroxy, benzoyloxy, carboxypropionyloxy, or hydroxyalkyl and R.sup.3, R.sup.4 and R.sup.6 are all hydrogen atoms or a pharmaceutically acceptable salt thereof.
- 5. A substituted purine of formula (I) according to claim 1 wherein R.sup.1 is hydroxy, E.sup.2 is amino, R.sup.5 is hydroxy and R.sup.3, R.sup.4 and R.sup.6 are each hydrogen; or a pharmaceutically acceptable salt thereof.
- 6. A substituted purine of formula (I) or a pharmaceutically acceptable salt thereof according to claim 1 wherein X is sulphur.
- 7. A substituted purine of formula (I) or a pharmaceutically acceptable salt thereof according to claim 2 wherein R.sup.2 is amino, R.sup.1 and R.sup.5 are both hydroxy and R.sup.3, R.sup.4 and R.sup.6 are each hydrogen.
- 8. A substituted purine of formula (I) or a pharmaceutically acceptable salt thereof according to claim 4 wherein R.sup.1 is hydroxy, R.sup.2 is amino, R.sup.5 is benzoyloxy and R.sup.3, R.sup.4 and R.sup.6 are each hydrogen.
- 9. A substituted purine of formula (I) or a pharmaceutically acceptable salt thereof according to claim 4 wherein R.sup.1 is hydroxy, R.sup.2 is amino, R.sup.5 is hydroxymethyl and R.sup.3, R.sup.4 and R.sup.5 are each hydrogen.
- 10. A substituted purine of formula (I) or a pharmaceutically acceptable salt thereof according to claim 4 wherein R.sup.1 is hydroxy, R.sup.2 is amino, R.sup.5 is carboxypropionyloxy and R.sup.3, R.sup.4 and R.sup.6 are each hydrogen.
- 11. A pharmaceutical composition which comprises an effective non-toxic antiviral treatment amount of a substituted purine of the formula (I) ##STR13## wherein X is sulphur or oxygen; R.sup.1 is hydroxy, R.sup.2 is amino; R.sup.3 is hydrogen, straight or branched chain or cyclic alkyl, hydroxyalkyl, benzoylalkyl or phenyl; R.sup.4 is hydrogen, hydroxy, or alkyl; R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzoyloxy, benzoyloxyalkyl, benzyloxy, sulphamoyloxy, phosphate, carboxypropionyloxy, or acetoxy; R.sup.6 is hydrogen, alkyl, or hydroxyalkyl; or a pharmaceutically acceptable salt thereof; together with a pharmaceutically acceptable carrier therefor.
- 12. A pharmaceutical composition as claimed in claim 11 in which X is oxygen.
- 13. A pharmaceutical composition as claimed in claim 11 in which R.sup.2 is amino, R.sup.1 and R.sup.5 are both hydroxy and R.sup.3, R.sup.4 and R.sup.6 are each hydrogen.
- 14. A pharmaceutical composition as claimed in claim 11, which is in the form of an ointment or cream.
- 15. A pharmaceutical composition as claimed in claim 11, which is in the form of a tablet.
- 16. A pharmaceutical composition for oral or parenteral administration as claimed in claim 11, comprising the compound in an amount of 1 to 250 mg per unit dose.
- 17. A pharmaceutical composition as claimed in claim 16 for parenteral administration or eye or nose drops comprising the compound in a concentration from 0.1 to 10% in an aqueous medium.
- 18. A pharmaceutical composition as claimed in claim 11 in a form for topical administration comprising the compound in a concentration from 0.1 to 10%.
- 19. A pharmaceutical composition as claimed in claim 18 comprising the compound in a concentration of 1%.
- 20. A purine selected from the group consisting of:
- 9-(3-Benzoylpropoxymethyl)guanine
- 9-[1-(2-Hydroxyethoxy)ethyl]guanine
- 9-Ethoxymethylguanine and
- 9-(4-Hydroxy-n-butoxymethyl)guanine hemihydrate.
- 21. The composition according to claim 11 in which the amount is 1 to 250 mg.
- 22. A pharmaceutical composition of claim 11 in which the substituted purine is selected from the group consisting of:
- 9-(3-Benzoylpropoxymethyl)guanine;
- 9-[1-(2-Hydroxyethoxy)ethyl]guanine;
- 9-Ethoxymethylguanine; and
- 9-(4-Hydroxy-n-butoxymethyl)guanine hemihydrate.
- 23. A method of treating a viral infection in a mammal, which comprises the administration of an effective, antiviral, non-toxic amount of a substituted purine of formula I as defined in claim 1 or a pharmaceutically acceptable acid addition salt thereof.
- 24. A method of treating a viral infection as claimed in claim 23 in which X is oxygen.
- 25. A method according to claim 23 wherein administration is by topical application.
- 26. A method according to claim 23 wherein administration is by the oral route.
- 27. A method according to claim 23 wherein administration is by the parenteral route.
- 28. A method according to claim 27 wherein the compound of formula (I) is administered in doses of from 0.1 to 250 mg/kg body weight.
- 29. A method according to claim 28, wherein the doses are repeated at least twice daily.
- 30. A method as claimed in claim 23 wherein the substituted purine compound is 9-(2-hydroxyethoxymethyl)guanine, 9(2-benzoyloxyethoxymethyl)guanine, 9-(3-hydroxypropoxymethyl) guanine, or 9-{2-(3-carboxypropionyloxy)ethoxymethyl}guanine,
- 31. A method of claim 23 in which the substituted purine is selected from the group consisting of:
- 9-(3-Benzoylpropoxymethyl)guanine;
- 9-[1-(2-Hydroxyethoxy)ethyl]guanine; and
- 9-Ethoxymethylguanine.
- 32. 9-(2-Formyloxyethoxymethyl) guanine or a pharmaceutically acceptable salt thereof.
- 33. A pharmaceutical composition comprising an effective non-toxic antiviral infection treatment amount of 9-(2-formyloxyethoxymethyl)guanine or a pharmaceutically acceptable salt thereof and a pharmaceutical acceptable carrier therefor.
- 34. A method of treating a susceptible viral infection in a mammal which comprises administering an effective non-toxic anti-viral amount of 9-(2-formyloxyethoxymethyl)guanine or a pharmaceutically acceptable salt thereof to said mammal.
- 35. The compound of the formula I ##STR14## wherein X is sulphur or oxygen, R.sup.1 is hydroxy; R.sup.2 is amino; R.sup.3 is hydrogen, straight or branch chain or cyclic alkyl, hydroxyalkyl, benzyloxyalkyl or phenyl; R.sup.4 is hydrogen, hydroxy or alkyl; R.sup.5 is hydrogen, hydroxy, amino, alkyl, hydroxyalkyl, benzyloxy, benzoyloxy, benzoyloxymethyl, sulphamoyloxy, phosphate or straight chain or cyclic acyloxy having from 1 to 8 carbon atoms; R.sup.6 is hydrogen or alkyl, or a pharmaceutically acceptable salt thereof.
- 36. The compound or pharmaceutically acceptable salt of claim 35 wherein R.sup.5 is straight chain or cyclic acyloxy having from 1 to 8 carbon atoms.
- 37. The compound or pharmaceutically acceptable of claim 36 wherein R.sup.5 is straight chain acyloxy.
- 38. The compound or pharmaceutically acceptable salt of claim 1 wherein R.sup.5 is acetoxy.
- 39. 9-(2-hydroxyethoxymethyl)guanine.
- 40. A pharmaceutically acceptable salt of 9-(2-hydroxyethoxymethyl)guanine.
- 41. A pharmaceutical composition comprising an effective non-toxic antiviral treatment amount of 9-(2-hydroxyethoxymethyl) guanine or a pharmaceutically acceptable salt thereof together with a pharmaceutically acceptable carrier therefore.
- 42. The composition of claim 41 in a form for oral administration.
- 43. The composition of claim 41 in a form for parenteral administration.
- 44. The composition of claim 41 in a form for topical administration.
- 45. The method of treating a susceptible viral infection in a mammal having said viral infection which comprises the administration of an effective antiviral non-toxic amount of 9-(2-hydroxyethoxymethyl)guanine or a pharmaceutically acceptable salt thereof.
- 46. The method of claim 45 in which the administration is oral.
- 47. The method of claim 45 in which the administration is parenteral.
- 48. The method of claim 45 in which the administration is topical.
- 49. The method of claim 45 in which the viral infection is caused by a herpes virus.
- 50. A pharmaceutical composition containing an effective non-toxic antiviral treatment amount of the compound or salt of claim 35 and a pharmaceutically acceptable carrier therefore.
- 51. A method of treating a susceptible viral infection in a mammal having said viral infection which comprises the administration of an effective antiviral non-toxic amount of the compound or salt of claim 35.
- 52. A pharmaceutical composition as claimed in claim 12 which is in the form of a ointment or cream.
- 53. A pharmaceutical composition as claimed in claim 13 which is in the form of an ointment or cream.
- 54. A pharmaceutical composition as claimed in claim 12 which is in the form of a tablet.
- 55. A pharmaceutical composition as claimed in claim 13 which is in the form of a tablet.
- 56. A pharmaceutical composition as claimed in claim 12 comprising the compound in an amount of 1 to 250 mg per unit dose.
- 57. A pharmaceutical composition as claimed in claim 13 comprising the compound in an amount of 1 to 250 mg per unit dose.
- 58. A pharmaceutical composition as claimed in claim 12 in a form for topical administration comprising the compound in a concentration from 0.1 to 10%.
- 59. A pharmaceutical composition as claimed in claim 13 in a form for topical administration comprising the compound in a concentration from 0.1 to 10%.
- 60. The method of claim 23 in which the alkyl has from 1 to 12 carbon atoms.
- 61. A method according to claim 25 wherein the compound of formula (I) is administered in doses of from 0.1 to 250 mg/kg body weight.
- 62. A method according to claim 26 wherein the compound of formula (I) is administered in doses of from 0.1 to 250 mg/kg body weight.
- 63. The pharmaceutical composition of claim 50 comprising wherein R.sup.5 is straight chain or cyclic acyloxy having 1 to 8 carbon atoms.
- 64. The pharmaceutical composition of claim 50 wherein R.sup.5 is straight chain acyloxy.
- 65. The pharmaceutical composition of claim 50 wherein R.sup.5 is acetoxy.
- 66. The method of claim 51 wherein R.sup.5 is straight chain or cyclic acyloxy having 1 to 8 carbon atoms.
- 67. The method of claim 51 wherein R.sup.5 is straight chain acyloxy.
- 68. The method of claim 51 wherein R.sup.5 is acetoxy.
- 69. The purine or pharmaceutically acceptable salt of claim 3 wherein R.sup.5 is acetoxy.
- 70. The purine or pharmaceutically acceptable salt of claim 3 wherein R.sup.5 is phosphate.
- 71. The method of claim 23 in which R.sup.5 is acetoxy.
- 72. The method of claim 23 in which R.sup.5 is phosphate.
- 73. The method of claim 23 in which R.sup.5 is carboxypropionyloxy.
- 74. The composition of claim 12 in which R.sup.5 is phosphate.
- 75. The composition of claim 12 in which R.sup.5 is carboxypropionyloxy.
- 76. The composition of claim 12 in which R.sup.5 is acetoxy.
- 77. 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine.
- 78. A pharmaceutically acceptable salt of: 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine.
- 79. A pharmaceutical composition comprising an effective non-toxic antiviral infection treatment amount of 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine or a pharmaceutically acceptable salt thereof.
- 80. A method of treating a susceptible viral infection in a mammal which comprises administering an effective non-toxic antiviral amount of 9-[2-(3-carboxypropionyloxy)ethoxymethyl]guanine or a pharmaceutically acceptable salt thereof to said mammal.
- 81. The purine or pharmaceutically acceptable salt of claim 2 in which R.sup.5 is carboxypropionyloxy.
Priority Claims (1)
Number |
Date |
Country |
Kind |
38278/74 |
Sep 1974 |
GBX |
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Parent Case Info
This application is a continuation in part of my earlier filed copending U.S. Pat. application Ser. No. 608,263 filed Aug. 27, 1975, now abandoned.
Non-Patent Literature Citations (1)
Entry |
Schaeffer et al., J. Med. Chem., vol. 14, (1971), pp. 367-369. |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
608263 |
Aug 1975 |
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