Back to results
US 5,789,608 AGranted
Phosphorus prodrugs
AssigneeDrug Innovation & Design, Inc.
InventorArnold Glazier
Life of this patent
Estimating the term…
Abstract
The composition and methods of synthesis of phosphorus prodrugs are described. These methods can be used to convert negatively charged phosphorous bearing drugs into neutrally charged; lipid soluble prodrugs which are able to passively diffuse into cells and into tissues in vivo. Prodrugs for a variety of antiviral and anti-leukemic agents are described.
Claims3
A compound represented by the following structural formula:
- ##STR31## wherein:
- R.sub.1 is a (--OCOR.sub.14) group;
- a (--O--CO--O--R.sub.14) group;
- a (--O--CO--NHCH.sub.3) group;
- or a (--O--CO--N(CH.sub.3).sub.2) group;
- R.sub.2 and R.sub.7 are independently hydrogen, a (--CO.sub.2 R.sub.10) group;
- a methyl group;
- a halogen;
- a methoxy group;
- a (--O--CO--R.sub.8) group, or a hydroxymethyl group (HO--CH.sub.2 --);
- R.sub.3 and R.sub.6 are independently hydrogen;
- a methyl group, a hydroxymethyl group (--CH.sub.2 --OH);
- --COOR.sub.9 ;
- a halogen;
- a hydroxyethyl group (--CH.sub.2 --CH.sub.2 --OH);
- --CH.sub.2 CO.sub.2 R.sub.11 ;
- or --CF.sub.3 ;
- R.sub.8 is a C1 to C31 straight chained alkyl group, isopropyl, t-butyl, a phenyl group or a group such that (H--O--CO--R.sub.8) is an amino acid, lactic acid, glycolic acid, acetoacetic acid;
- R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are independently a methyl, ethyl, phenyl or benzyl group;
- R.sub.14 is a C1-C31 straight chain alkyl group, --O--(C1-C31 straight chain group), isopropyl, --O-isopropyl, t-butyl, --O--(t-butyl), phenyl, --O-phenyl, --NHCH.sub.3, --N(CH.sub.3).sub.2 or R.sub.14 can be selected such that R.sub.14 --CO.sub.2 H is an amino acid;
- lactic acid;
- glycolic acid (--HO--CH.sub.2 --CO.sub.2 H);
- glyceric acid (HO--CH.sub.2 --CH(OH)--CO.sub.2 H);
- or acetoacetic acid (CH.sub.3 COCH.sub.2 --CO.sub.2 H).
21 more elements
A compound represented by the following structural formula:
- ##STR33## wherein:
- R.sub.1 is a (--OCOR.sub.14) group;
- a (--O--CO--O--R.sub.14) group;
- a (--O--CO--NHCH.sub.3) group;
- or a (--O--CO--N(CH.sub.3).sub.2) group;
- R.sub.2 and R.sub.7 are independently hydrogen;
- a (--CO.sub.2 R.sub.10) group;
- a C1--C31 straight chained alkyl group;
- isopropyl;
- t-butyl;
- a halogen;
- --O--(C1-C31 straight chained alkyl group);
- --O--(isopropyl);
- --O--(t-butyl);
- a (--O--CO--R.sub.8) group;
- or a hydroxymethyl group (HO--CH.sub.2);
- R.sub.3 and R.sub.6 are independently hydrogen;
- a C1-C31 straight chained alkyl group;
- isopropyl;
- t-butyl;
- a (--CO.sub.2 R.sub.9) group;
- a hydroxymethyl group (--CH.sub.2 --OH);
- a halogen;
- a hydroxyethyl group (--CH.sub.2 --CH.sub.2 --OH);
- a --CH.sub.2 CO.sub.2 R.sub.11 group;
- or --CF.sub.3 ;
- R.sub.8 is a C1-C31 straight chain alkyl group, isopropyl or t-butyl;
- a substituted or unsubstituted phenyl group, or a group such that (H--O--CO--R.sub.8) is an amino acid, lactic acid, glycolic acid, acetoacetic acid;
- R.sub.9, R.sub.10, R.sub.11 and R.sub.12 are independently a C1-C30 straight chain alkyl group, an isopropyl group or a t-butyl group;
- a phenyl group, a substituted phenyl group, a benzyl group or a substituted benzyl group;
- R.sub.14 is a C1-C31 straight chain alkyl group, --O--(C1-C31 straight chain group), isopropyl, --O-isopropyl, t-butyl, --O--(t-butyl), phenyl, --O-phenyl, a substituted phenyl group, --O--(substituted phenyl), --NHCH.sub.3, --N(CH.sub.3).sub.2 or R.sub.14 can be selected such that R.sub.14 --CO.sub.2 H is;
- an amino acid;
- lactic acid;
- glycolic acid (--HO--CH.sub.2 --CO.sub.2 H);
- glyceric acid (HO--CH.sub.2 --CH(OH)--CO.sub.2 H);
- or acetoacetic acid (CH.sub.3 COCH.sub.2 --CO.sub.2 H).
33 more elements
Dependencies are inferred from the claim text.