Processes and intermediates for preparing substituted hexahydrofuro [2,3-b] furans
The invention described herein pertains to processes and compounds useful in the preparation of bis-tetrahydrofurans. The invention described herein also pertains to compounds useful for treating HIV infections.
1. A compound having the formula
wherein R 1 is hydrogen or an OH protecting group, or is selected from the group consisting of alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, heteroalkyl, heteroalkenyl, cycloheteroalkyl, cycloheteroalkenyl, aryl, heteroaryl, arylalkyl, and heteroarylalkyl, each of which is optionally substituted; R 2 is alkyl, cycloalkyl, heteroalkyl, cycloheteroalkyl, arylalkyl, or heteroalkyl, each of which is optionally substituted; R P2 is hydrogen, hydroxyl protecting group or a pro -drug forming group; R 3 is alkyl, heteroalkyl, cycloalkyl, cycloheteroalkyl, arylalkyl, or heteroarylalkyl; Ar is aryl is optionally substituted with a radical —(CH 2 ) X Z x , where x is an integer from 0-6 and Z X is selected from halogen, hydroxy, alkanoyloxy, optionally substituted aroyloxy, alkyl, alkoxy, cycloalkyl, cycloalkoxy, alkenyl, alkynyl, haloalkyl, haloalkoxy, halocycloalkyl, halocycloalkoxy, C 1 -C 6 alkylamino, (C 1 -C 6 alkyl)(C 1 -C 6 alkyl)amino, alkylcarbonylamino, N—(C 1 -C 6 alkyl)alkylcarbonylamino, aminoalkyl, C 1 -C 6 alkylaminoalkyl, (C 1 -C 6 alkyl)(C 1 -C 6 alky)aminoalkyl, alkylcarbonylaminoalkyl, N—(C 1 -C 6 alkyl)alkylcarbonylaminoalkyl, cyano, and nitro or Z X is selected from —CO 2 R 4 and—CONR 5 R 6 , where R 4 , R 5 , and R 6 are each independently selected in each occurrence from hydrogen, C 1 -C 6 alkyl, aryl-C 1 -C 6 alkyl, and heteroaryl-C 1 -C 6 alkyl; or Ar is 3,4-methylenedioxyphenyl; or Ar is heteroaryl which is optionally substituted; and
wherein the compound is not
2. The compound of claim 1 which is
3. The compound of claim 1 wherein R 2 is arylalkyl.
4. The compound of claim 3 wherein R 2 is benzyl.
5. The compound of claim 1 wherein R 3 is branched alkyl.
6. The compound of claim 5 wherein R 3 is iso-butyl.
7. The compound of claim 1 wherein R P2 is hydrogen.
8. The compound of claim 1 wherein Ar is substituted phenyl.
9. The compound of claim 1 wherein R 1 is alkyl or arylalkyl.
10. The compound of claim 9 wherein R 1 is methyl or benzyl.
11. The compound of claim 1 wherein Ar is phenyl substituted on the 4 position with OMe, CH 2 OMe or Ar is 3,4-methylenedioxyphenyl.
12. The compound of claim 1 wherein Ar is phenyl substituted on the 4 position with OMe, CH 2 OMe, or Ar is 3,4-methylenedioxyphenyl; R 1 is methyl or benzyl; R 2 is arylalkyl; R is branched alkyl; and R P2 is hydrogen.
13. The compound of claim 12 wherein R 1 is methyl; R 2 is benzyl; and R 3 is iso-butyl.
14. A pharmaceutical composition comprising the compound of claim 1 ; and one or more carriers, diluents, or excipients, or a combination thereof.
15. A method of treating a patient in need of relief from HIV infection comprising the step of administering to the patient a therapeutically effective amount of the compound of claim 1 .
16. A pharmaceutical composition comprising the compound of claim 2 ; and one or more carriers, diluents, or excipients, or a combination thereof.
17. A method of treating a patient in need of relief from HIV infection comprising the step of administering to the patient a therapeutically effective amount of the compound of claim 2 .