Details for Patent: 5,340,816
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Title: | Hydroxymethyl(methylenecyclopentyl) purines and pyrimidines |
Abstract: | Antiviral activity is exhibited by compounds having the formula ##STR1## and its pharmaceutically acceptable salts. |
Inventor(s): | Zahler; Robert (Pennington, NJ), Slusarchyk; William A. (Skillman, NJ) |
Assignee: | E. R. Squibb & Sons, Inc. (Princeton, NJ) |
Filing Date: | Jan 15, 1993 |
Application Number: | 08/004,006 |
Claims: | 1. A compound having the formula ##STR105## or a pharmaceutically acceptable salt thereof wherein: ##STR106## R.sub.2 is fluoro, chloro, bromo, iodo, hydrogen, methyl, trifluoromethyl, ethyl, n-propyl, 2-fluoroethyl, 2-chloroethyl, ethynyl or ##STR107## R.sub.3 is chloro, bromo, iodo, hydrogen, methyl or trifluoromethyl; R.sub.5 is hydrogen, alkyl of 1 to 10 carbons, substituted alkyl of 1 to 10 carbons wherein said substituent is selected from the group consisting of halogen, amino, azido, hydroxy, cyano, trialkylammonium wherein each alkyl has 1 to 6 carbons, alkoxy of 1 to 6 carbons, phenyl, and carboxy, phenyl, or phenyl substituted with one, two or three substituents selected from the group consisting of alkyl of 1 to 6 carbons, alkoxy of 1 to 6 carbons, halogen, trifluoromethyl, amino, alkylamino of 1 to 6 carbons, dialkylamino wherein each alkyl is of 1 to 6 carbons, nitro, cyano, alkanoyloxy of 2 to 11 carbons, carboxy, carbamoyl, and hydroxy; and R.sub.6 and R.sub.7 are independently hydrogen, --PO.sub.3 H.sub.2 or ##STR108## 2. A compound according to claim 1 wherein R.sub.6 and R.sub.7 are independently hydrogen or ##STR109## 3. A compound according to claim 1 wherein R.sub.6 and R.sub.7 are independently hydrogen or --PO.sub.3 H.sub.2. 4. A compound according to claim 1 wherein R.sub.6 and R.sub.7 are hydrogen. 5. A compound according to claim 1 wherein R.sub.1 is ##STR110## 6. A compound according to claim 1 wherein R.sub.1 is ##STR111## 7. A compound according to claim 1 wherein R.sub.1 is ##STR112## 8. A compound according to claim 1 wherein R.sub.1 is ##STR113## 9. A compound according to claim 1 wherein R.sub.1 is ##STR114## 10. A compound according to claim 1 wherein R.sub.1 is ##STR115## 11. A compound according to claim 1, [1S-(1.alpha.,3.alpha.,4.beta.)]-1-[4-hydroxy-3-(hydroxymethyl)-2 -methylenecyclopentyl]-5-methyl-2,4(1H,3H)-pyrimidinedione. 12. A compound according to claim 1, [1S-(1.alpha.,3.alpha.,4.beta.)]-4-amino-1-[4-hydroxy-3-(hydroxymethyl)-2- methylenecyclopentyl]-2(1H)-pyrimidinone. 13. A compound according to claim 1, [1S-(1.alpha.,3.alpha.,4.beta.)]-1-[4-hydroxy-3-(hydroxymethyl )-2-methylenecyclopentyl]-5-iodo-2,4(1H,3H)-pyrimidinedione. 14. A compound according to claim 1, [1S-[1.alpha.(E),3.alpha.,4.beta.]]-5-(2-bromoethenyl)-1-[4-hydroxy-3-(hyd roxymethyl)-2-methylenecyclopentyl]-2,4(1H,3H)-pyrimidinedione. 15. A compound according to claim 1, [1S-[1.alpha.(E),3.alpha.,4.beta.]]-5-(2-chloroethenyl)-1- [4-hydroxy-3-(hydroxymethyl)-2-methylenecyclopentyl]-2,4(1H,3H)-pyrimidine dione. 16. A compound according to claim 1, [1S-[1.alpha.(E),3.alpha.,4.beta.]]-1-[4-hydroxy-3-(hydroxymethyl)-2-methy lenecyclopentyl]-5-(2-iodoethenyl)-2,4(1H,3H)-pyrmidinedione. 17. A compound according to claim 1 wherein: ##STR116## 18. A compound according to claim 1 wherein: ##STR117## 19. An antiviral composition useful for treating herpes simplex virus 1 and 2, varicella zoster virus, and human cytomegalovirus comprising a pharmaceutically acceptable carrier and an effective amount of a compound of the formula ##STR118## wherein R.sub.1, R.sub.6 and R.sub.7 are as defined in claim 1. 20. A method of treating a herpes simplex virus 1, a herpes simplex virus 2, a varicella zoster virus, or a human cytomegalovirus infection in a mammalian species comprising administering an effective amount of the composition of claim 19. |