Production of 2',3'-dideoxy-2',3'-didehydronucleosides
AssigneeBristol-Myers Squibb Company
InventorsJohn E. Starrett, Jr., Muzammil M. Mansuri, John C. Martin, Carl E. Fuller, Henry G. Howell
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Abstract
There are disclosed novel processes for producing 2',3'-dideoxy-2'3'-didehydronucleosides, for example, 2',3'-dideoxy-2',3'-didehydrothymidine in high yields and on a large scale. The compounds so-produced are useful as antiviral agents, especially as agents effective against the human immunodeficiency viruses (HIV).
Claims6
A process for producing a 2',3'-dideoxy-2',3'-didehydronucleoside represented by the formula ##STR24## wherein the base moiety is a member selected from the group of unsubstituted and substituted bases consisting of pyrimidine, aza-pyrimidine, and deaza-pyrimidine;
- X is selected from N and C-H;
- Y is selected from C-R.sup.5 and N;
- Z is selected from C-H and N;
- R.sup.4 is selected from OH and NH.sub.2 ;
- and R.sup.5 is selected from H, unsubstituted and halo-substituted alkyl having the formula C.sub.n H.sub.2n A, and unsubstituted and halo-substituted alkenyl having the formula --(CH.sub.2).sub.m -CH.dbd.CHA, wherein m is an integer selected from 0, 1, 2 and 3, n is an integer selected from 1, 2, and 3 and A is selected from H, F, Cl, Br, and I, comprising the steps of:
- (a) reacting, with a strong base, a 2'-deoxynucleoside represented by the formula ##STR25## to form a reactive 2,3'-anhydro-2'-deoxynucleoside intermediate represented by the formula ##STR26## and (b) converting in the presence of base selected from non-nucleophilic and nucleophilic bases said reactive 2,3'-anhydro-2'-deoxynucleoside from step (a) above to said 2',3'-dideoxy-2',3'-didehydronucleoside.
Dependencies are inferred from the claim text.