Biologically reversible phosphate and phosphonate protective groups
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.
Claims6
A bioreversibly protected phosphate compound having the formula:
- ##STR12## where R.sup.1 is selected from the group consisting of hydrogen, alkyl hydrocarbons having from 1-10 carbon atoms, aryl or alkaryl hydrocarbons having from 6-10 carbon atoms, and amines having the formula NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are independently hydrogen or an alkyl hydrocarbon having from 1-10 carbon atoms;
- R.sup.2 is nucleosid-5'-yl;
- and
- R.sup.3 is hydrogen or methyl.
A bioreversibly protected phosphate compound having the formula:
- ##STR13## where R.sup.1 is selected from the group consisting of hydrogen, alkyl hydrocarbons having from 1-10 carbon atoms, aryl or alkaryl hydrocarbons having from 6-10 carbon atoms, and amines having the formula NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are independently hydrogen or an alkyl hydrocarbon having from 1-10 carbon atoms;
- R.sup.2 is 2'-deoxynucleosid-5'-yl;
- and
- R.sup.3 is hydrogen or methyl.
A bioreversibly protected phosphate compound, having the formula:
- ##STR14## where R.sup.1 is selected from the group consisting of hydrogen, alkyl hydrocarbons having from 1-10 carbon atoms, aryl or alkaryl hydrocarbons having from 6-10 carbon atoms, and amines having the formula NR.sup.4 R.sup.5 where R.sup.4 and R.sup.5 are independently hydrogen or an alkyl hydrocarbon having from 1-10 carbon atoms;
- R.sup.2 is selected from the group consisting of
- ' -deoxy-5-fluorouridin-5'-yl
- 2'-deoxy-3'-O-acetyl-5-fluorouridin-5'-yl
- 2'-deoxyuridin-5'-yl
- 2'-deoxy-5-bromouridin-5'-yl
- 2'-deoxy-5-iodouridin-5'-yl
- ' -deoxy-t-(bromovinyl)-uridin-5'-yl thymidin-5'-yl, and
- 3'-O-acetylthymidin-5'-yl;
- and
- R.sup.3 is hydrogen or methyl.
Dependencies are inferred from the claim text.