Spermicidally active 5-halo-6-alkoxy-5,6-dihydro-2′,3′-dideoxy-uridines and their pharamaceutical compositions
AssigneeWayne Hughes Institute
InventorsOsmond D'Cruz, Fatih M. Uckun, Taracad Venkatachalam
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Abstract
Contraceptive activity as well as anti-viral protection can be provided by contraceptive compositions containing a pyrimidine-based nucleoside or nucleotide exhibiting spermicidal or sperm-immobilizing activity. In one example, the active ingredient contains a thymine ring (e.g. AZT) that has 5-halo, 6-alkoxy substitution. Additional improvements in anti-HIV activity for certain AZT derivatives are seen by providing the pentose ring of AZT with aryl phosphate substitution.
Claims24
A method of inhibiting conception in a mammal, comprising contacting mammalian sperm with an effective spermicidal amount of a compound of formula I:
- where
- R1 is H, N3, halogen, CN, COOH, NH2, NH—CH3, NH—COCH3, NH—Ph, NH—COPh or NH—CH2—Ph,
- R2 is halogen,
- R3 is C1-3 alkoxy, and
- R′ is selected from the group consisting of H, a phosphate,
- and a fatty acid acyl group
- where R4, R5, and R6 are the same or different and are selected from the group consisting of hydrogen, methyl, ethyl, fluoro, chloro, bromo, iodo, trifluoromethyl, nitro, cyano, methoxy, trifluoromethoxy and ethoxy, and R″ is an N-amino acid residue,
- or a pharmaceutically acceptable salt or ester of the compound of formula I.
A compound of formula I:
- where:
- R1 is N3;
- R2 is Br;
- R3 is OMe;
- R4 is Br;
- and
- R5 and R6 are hydrogen;
- or a pharmaceutically acceptable salt or ester thereof.
A pharmaceutical composition, comprising:
- an effective spermicidal amount of a compound of formula I:
- where
- R1 is H, CN, COOH, NH2, NH—CH3, NH—COCH3, NH—Ph, NH—COPh or NH—CH2—Ph,
- R2 is halogen,
- R3 is C1-3 alkoxy, and
- R′ is, selected from the group consisting of H, a phosphate,
- and a fatty acid acyl group,
- where
- R4, R5, and R6 are the same or different and are selected from the group consisting of hydrogen, methyl, ethyl, fluoro, chloro, bromo, iodo, trifluoromethyl, nitro, cyano, methoxy, trifluoromethoxy and ethoxy, and R″ is an N-amino acid residue,
- or a pharmaceutically acceptable salt or ester of the compound of formula I;
- and a carrier, diluent or vehicle suitable for contraceptive use.
A compound of the formula:
- where
- R1 is N3, NH2 NH—CH3, NH—COCH3, NH—Ph, NH—COPh or NH—CH2—Ph,
- R2 is halogen, R3 is C1-C3 alkoxy,
- R4 is hydrogen, halogen or C1-C3 alkoxy, and
- R5 and R6 are hydrogen.
Dependencies are inferred from the claim text.