Biologically reversible phosphate and phosphonate protective gruops
AssigneeBoard of Regents, The University of Texas System
InventorDavid Farquhar
Life of this patent
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Abstract
Protective groups are provided which are suitable for masking phosphates and phosphonates. The protected compositions can be introduced in a biological system and then demasked under certain biological conditions. This method permits phosphates and phosphonates which would themselves degrade in the biological system and therefore be ineffective to be introduced in a protected form and late released under the proper conditions.
Claims14
Compounds having the formula ##STR16## where R.sup.1 is selected from the group consisting of H, alkyl hydrocarbons having 1-10 carbons, aryl and alkaryl hydrocarbons having 6-10 carbons, and amines having the formula NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are independently selected from the group consisting of H and alkyl hydrocarbons having 1-10 carbons;
- R.sup.3 is selected from the group consisting of H and alkyl hydrocarbons having 1-3 carbons;
- X.sup.1 is selected from the group consisting of H and
- X.sup.2 is selected from the group consisting of R.sup.2 and OR.sup.2 ;
- and
- R.sup.2 is selected from the group consisting of H, alkyl hydrocarbons having 1-10 carbons, aryl and alkaryl hydrocarbons having 6-10 carbons, and nucleosides.
Compounds having the formula ##STR17## where R.sup.1 is selected from the group consisting of CH.sub.3,CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- X.sup.1 selected from the group consisting of H and R.sup.1 COOCH.sub.2 ;
- and
- R.sup.2 is selected from the group consisting of
- ' . 3'-dideoxyuridin-5'-yl groups
- 2',3'-dideoxycytidin-5'-yl groups
- 2',3'-dideoxyguanosin-5'-yl groups,
- and groups having the formula
- CH.sub.2 CH.sub.2 OCH.sub.2 B
- where B is a base selected from the group consisting of thymine, uracil, cytosine, guanine, adenine, and xanthine.
Compounds having the formula ##STR18## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- and
- R.sup.2 is selected from the group consisting of
- ' . 3'-dideoxyuridine-5'-yl
- 2'-fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-azido-2',3'-dideoxyuridine-5'-yl
- 3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-chloro-2',3'-dideoxyuridine-5'-yl
- 5-bromo-2',3'-dideoxyuridine-5'-yl
- 5-iodo-2',3'-dideoxyuridine-5'-yl
- 5-methyl-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-fluoro-2',3'-diideoxyuridine-5'-yl
- 5-methyl-3'-azido-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-ethyl-2',3'-dideoxyuridine-5'-yl
- 5-propyl-2',3'-dideoxyuridine-5'-yl
- 2',3'-dideoxycytidin-5'-yl
- 2'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-azido-2',3'-dideoxycytidin-5'-yl
- 5-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-chloro-2',3'-dideoxycytidin-5'-yl
- 5-bromo-2',3'-dideoxycytidin-5'-yl
- 5-iodo-2',3'-dideoxycytidin-5'-yl
- 5-methyl-2',3'-dideoxycytidin-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-methyl-3'-azido-2',3'-dideoxycytidin-5'-yl
- 2',3'-dideoxyadenosin-5'-yl
- 2',3'-dideoxyguanosin-5'-yl
- 2',3'-dideoxyxanthosin-5'-yl
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Guanine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Adenine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Thymine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Uracil
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Cytosine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Xanthine
Compounds having the formula ##STR19## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- and
- R.sup.2 is selected from the group consisting of
- ' . 3'-dideoxyuridine-5'-yl
- 2'fluoro-2',3'-dideoxyuridine-5'-yl;
- ' -fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-azido-2',3'-dideoxyuridine-5'-yl
- 3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-chloro-2',3'-dideoxyuridine-5'-yl
- 5-bromo-2',3'-dideoxyuridine-5'-yl
- 5-iodo-2',3'-dideoxyuridine-5'-yl
- 5-methyl-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-azido-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-ethyl-2',3'-dideoxyuridine-5'-yl
- 5-propyl-2',3'-dideoxyuridine-5'-yl
- 2',3'-dideoxycytidin-5'-yl
- 2'-fluoro-2',3'-diedoxycytidin-5'-yl
- 3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-azido-2',3'-dideoxycytidin-5'-yl
- 5-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-chloro-2',3'-dideoxycytidin-5'-yl
- 5-bromo-2',3'-dideoxycytidin-5'-yl
- 5-iodo-2',3'-dideoxycytidin-5'-yl
- 5-methyl-2',3'-dideoxycytidin-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-methy-3'-azido-2',3'-dideoxycytidin-5'-yl
- 2',3'-dideoxyadenosin-5'-yl
- 2',3'-dideoxyguanosin-5'-yl
- 2',3'-dideoxyxanthosin-5'-yl
- --CH.sub.2 CH.sub.2 OCH.sub.2 ---Guanine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Adenine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Thymine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Uracil
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Cytosine
- --CH.sub.2 CH.sub.2 OCH.sub.2 --Xanthine.
Compounds having the formula ##STR20## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3;
- and
- R.sup.2 is selected from the group consisting of
- ' . 3'-dideoxyuridine-5'-yl
- 2'-fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-azido-2',3'-dideoxyuridine-5'-yl
- 3'amino-2',3'-didoxyuridine-5'-yl
- 5-chloro-2',3'-dideoxyuridine-5'-yl
- 5-bromo-2,3'-dideoxyuridine-5'-yl
- 5-iodo-2',3'-dideoxyuridine-5'-yl
- 5-methyl-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-azido-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-ethyl-2',3'-dideoxyuridine-5'-yl
- 5-propyl-2',3'-dideoxyuridine-5'-yl
- 2',3'-dideoxycytidin-5'-yl
- 2'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-azido-2',3'-dideoxycytidin-5'-yl
- 5-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-chloro-2',3'-dideoxycytidin-5'-yl
- 5-bromo-2',3'-dideoxycytidin-5'-yl
- 5-iodo-2',3'-dideoxycytidin-5'-yl
- 5-methyl-2',3'-dideoxycytidin-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxycytidin-
- 5'-yl
- 5-methyl-3'-azido-2',3'-dideoxycytidin-5'-yl.
Compounds having the formula ##STR21## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- and
- R.sup.2 is selected from the group consisting of
- ' . 3'-dideoxyuridine-5'-yl
- 2'-fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-fluoro-2',3'-dideoxyuridine-5'-yl
- 3'-azido-2',3'-dideoxyuridine-5'-yl
- 3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-chloro-2',3'-dideoxyuridine-5'-yl
- 5-bromo-2,3'-dideoxyuridine-5'-yl
- 5-iodo-2',3'-dideoxyuridine-5'-yl
- 5-methyl-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-azido-2',3'-dideoxyuridine-5'-yl
- 5-methyl-3'-amino-2',3'-dideoxyuridine-5'-yl
- 5-ethyl-2',3'-dideoxyuridine-5'-yl
- 5-propyl-2',3'-dideoxyuridine-5'-yl
- 2',3'-dideoxycytidin-5'-yl
- 2'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 3'-azido-2',3'-dideoxycytidin-5'-yl
- 5-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-chloro-2',3'-dideoxycytidin-5'-yl
- 5-bromo-2',3'-dideoxycytidin-5'-yl
- 5-iodo-2',3'-dideoxycytidin-5'-yl
- 5-methyl-2',3'-dideoxycytidin-5'-yl
- 5-methyl-3'-fluoro-2',3'-dideoxycytidin-5'-yl
- 5-methyl-3'-azido-2',3'-dideoxycytidin-5'-yl.
Compounds having the formula ##STR22## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- and
- R.sup.2 is selected from the group consisting of
- ' . 3'-dideoxyadensosin-5'-yl, and
- 2',3'-dideoxyxanthosin-5'-yl.
- 2',3'-dideoxyxanthosin-5'-yl.
Compounds having the formula ##STR23## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- and
- B is a base selected from the group consisting of guanine, adenine, thymine, uracil, cytosine, and xanthine.
Compounds having the formula ##STR24## where R.sup.1 is selected from the group consisting of H, CH.sub.3, CH.sub.2 CH.sub.3, CH(CH.sub.3).sub.2, and C(CH.sub.3).sub.3 ;
- and
- B is a base selected from the group consisting of guanine, adenine, thymine, uracil, cytosine, and xanthine.
Dependencies are inferred from the claim text.