You’re using a public version of DrugPatentWatch with 5 free searches available | Register to unlock more free searches. CREATE FREE ACCOUNT

Last Updated: March 28, 2024

Details for Patent: 5,340,816


✉ Email this page to a colleague

« Back to Dashboard


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.

Make Better Decisions: Try a trial or see plans & pricing

Drugs may be covered by multiple patents or regulatory protections. All trademarks and applicant names are the property of their respective owners or licensors. Although great care is taken in the proper and correct provision of this service, thinkBiotech LLC does not accept any responsibility for possible consequences of errors or omissions in the provided data. The data presented herein is for information purposes only. There is no warranty that the data contained herein is error free. thinkBiotech performs no independent verification of facts as provided by public sources nor are attempts made to provide legal or investing advice. Any reliance on data provided herein is done solely at the discretion of the user. Users of this service are advised to seek professional advice and independent confirmation before considering acting on any of the provided information. thinkBiotech LLC reserves the right to amend, extend or withdraw any part or all of the offered service without notice.