Back to results
US 5,272,250 AGranted
Boronated phosphoramidate compounds
OwnerBernard F. Spielvogel, Anup Soodinventors
Life of this patent
Estimating the term…
Abstract
A class of pharmaceutically active boronated compounds are provided. The boronated compounds include boronated phosphoramidates, and boronated nucleosides, and oligomers thereof. The compounds are boronated by an aminoalkyl substituted polyborane, carborane, metallopolyborane or metallocarborane.
Claims18
A boronated compound according to the formula ##STR3## wherein:
- R and R.sup.1 are each independently selected from the group consisting of hydrogen, alkyl, and alkylaryl;
- R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, alkyl, alkylaryl, aryl, nucleosides and oligonucleotides;
- and
- W is polyborane or carborane, and wherein x is an integer from 1 to 20.
1 more element
A boronated compound according to the formula ##STR4## wherein:
- R is hydrogen or C.sub.1 to C.sub.5 linear alkyl;
- R.sup.2 and R.sup.3 are each independently selected from the group consisting of hydrogen, alkyl, alkylaryl, aryl, nucleosides and oligonucleotides;
- and
- W is a carborane, and wherein x is an integer from 1 to 5.
1 more element
A boronated compound selected from the group consisting of:
- (a) Dimethyl N-methyl-N-(o-carboranylmethyl) phosphoramidate;
- (b) Diethyl N-methyl-N-(o-carboranylmethyl) phosphoramidate;
- (c) Diethyl N-methyl-N(m-carboranylmethyl) phosphoramidate;
- (d) Dimethyl N-methyl-N-(p-carboranylmethyl) phosphoramidate;
- (e) Diisopropyl N-methyl-N-(p-{1-butyl} carboranylmethyl)-phosphoramidate;
- (f) Diethyl N-methyl-N-(o-{1-methyl} carboranylethyl)-phosphoramidate;
- (g) Di-n-propyl N-ethyl-N-(2-(dodecahydrododecaborato}ethyl)-phosphoramidate, disodium salt;
- (h) Dimethyl N-methyl-N-(2-{decahydrodecaborato}ethyl)-phosphoramidate, diammonium salt;
- (j) Thymidine-3'-O-[ethyl(N-methyl-N-{2-(o-carboranylethyl)})]-phosphoramidate
- (k) Guanosine-3'-O-[ethyl(N-methyl-N-{2-(o-carboranylethyl)})]-phosphoramidate ;
- (l) 2'-Deoxycytidine-3'-O-[ethyl(N-methyl-N-{(2-(o-carboranylethyl)})]-phospho ramidate;
- (m) Thymidine-3'-O-[ethyl(N-methyl-N-{2-(1,2-dicarbonidoundecaboranyl)ethyl)}) ]-phosphoramidate anion;
- (n) Adenosine-3'-O-[ethyl(N-methyl-N-{2-(1,2-dicarbonidoundecaboranyl)ethyl)}) ]-phosphoramidate, tetramethylammonium salt.
- (o) Dodecathymidylyl-(N-methyl-N-(o-(1-methyl)carboranylethyl)-phosphoramidate ;
- (p) Undecaguanyl-(N-methyl-N-(o-(1-methyl)carboranylethyl)-phosphoramidate;
- (q) Hexadecacytidylyl-(N-methyl-N-(o-(1-methyl)carboranylethyl)-phosphoramidat e;
- (r) ApTpCpGpTpTpTpAp.sup.* T where p=normal phosphate and p.sup.* =N-ethyl-N-(1,7-dicarboclosododecaboranyl)methylphosphoramidate (SEQ ID No. 1);
- (s) Tp.sup.* Ap.sup.* Tp.sup.* Gp.sup.* Cp.sup.* Ap.sup.* Tp.sup.* Gp.sup.* Ap.sup.* Ap.sup.* Cp.sup.* Cp.sup.* Gp.sup.* Tp.sup.* T where p.sup.* =N-butyl-N-(6-[{1-propyl}1,12-dicarboclosododecaboranyl])hexyl-phosphorami date (SEQ ID No. 2);
- (t) Tp'Tp'Ap'Ap'Ap'Tp.sup.* Tp.sup.* Tp.sup.* Ap.sup.* Ap.sup.* where p'=thiophosphate, p.sup.* =N-methyl-N-[2-(o-(1-methyl) carboranylethyl)] phosphoramidate (SEQ ID No. 3);
- (u) Cp.sup.* Cp.sup.* Cp.sup.* Gp.sup.* Gp.sup.* Gp.sup.* CpCpCpGpGpGp where p=normal phosphate and p.sup.* =N-ethyl-N-(1,7-dicarboclosododecaboranyl)methyl-phosphoramidate (SEQ ID No. 4);
- (v) Tp'Tp'Tp'Tp'Tp'Tp'Tp'Tp.sup.* Tp.sup.* Tp.sup.* Tp.sup.* Tp.sup.* T where p'=N-methyl-N-{2-(1,2-dicarbonidoundecaboranyl) ethyl)})]-phosphoramidate, ammonium salt and p.sup.* =N-butyl-N-(6-[{1-propyl} 1,12-dicarboclosododecaboranyl])hexyl-phosphoramidate (SEQ ID No. 5);
- and
- (w) Ap'Tp'Cp'Gp'Tp'Gp'Ap.sup.* Tp.sup.* Ap.sup.* Cp.sup.* Gp.sup.* T where p'=N-ethyl-N-(1,7-dicarboclosododecaboranyl)methyl-phosphoramidate and p.sup.* =N-ethyl-N-(2-{dodecahydrododecaborato}ethyl)-phosphoramidate, disodium salt (SEQ ID No. 6).
20 more elements
Dependencies are inferred from the claim text.