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US 5,807,847 AGranted
Nitrate esters
AssigneeQueen's University at Kingston
InventorsGregory R. J. Thatcher, Brian M. Bennett
Life of this patent
Estimating the term…
Abstract
Aliphatic Nitrate esters having a sulfur or phosphorus atom .beta. or .gamma. to a nitrate group having efficacy as vasodilators are described. Preferred nitrate esters may be synthesized by nitration of a 3-bromo-1,2-propanediol, and subsequent reaction to yield the desired mono, di or tetra nitrate ester.
Claims7
Aliphatic nitrate esters containing at least one nitrate group, in which a S or P atom is situated .beta. or .gamma. to a nitrate group, having the general formula:
- ##STR10## where X is CH.sub.2, O, NH, NMe, S, SO.sub.3 M, PO.sub.3 HM, PO.sub.3 M.sub.2, SH, SR.sub.7, P(O)(OR.sub.6)(OR.sub.6), P(O)(OR.sub.6)(OM), P(O)(OR.sub.5)(R.sub.6), P(O)(OM)R.sub.6, SO.sub.2 M, S(O)R.sub.8, S(O).sub.2 R.sub.9, S(O)OR.sub.8 or S(O).sub.2 OR.sub.9 ;
- Y is SR.sub.4, SR.sub.10, SSR.sub.10, SO.sub.2 M, SO.sub.3 M, PO.sub.3 HM, PO.sub.3 M.sub.2, P(O)(OR.sub.5)(OM), or P(O)(OR.sub.5)(OR.sub.6), or does not exist;
- R.sub.5, R.sub.6, R.sub.8, R.sub.9, R.sub.10, are the same or different alkyls containing 1-12 carbon atoms or C.sub.1 or C.sub.2 connections to R.sub.1 or R.sub.3 in cyclic derivatives;
- R.sub.7 is C.sub.1 -C.sub.8, alkyl or acyl;
- R.sub.2 and R.sub.4 are the same or different and selected from H, ONO.sub.2, C.sub.1 -C.sub.4 alkyl optionally bearing 1-3 nitrate groups, and acyl groups (--C(O)R.sub.10);
- R.sub.1 and R.sub.3 are the same or different and selected from H, C.sub.1 -C.sub.4 alkyl and chains, which may include one O, linking R.sub.1 and R.sub.3 to form pentosyl, hexosyl, cyclopentyl or cycohexyl rings, which rings optionally bear hydroxyl substituents;
- and
- M is H, Na.sup.+, K.sup.+, NH.sub.4.sup.+ or N.sup.+ H.sub.n R.sub.11(4-n), where n is 0-3;
- and
- with the proviso that, when R.sub.6 is an alkyl group, and R, R.sub.2 and R.sub.4 .dbd.H, R.sub.3 is not H or methyl.
7 more elements
A pharmaceutical composition comprising an effective amount of an aliphatic nitrate ester having the formula:
- ##STR13## where X is CH.sub.2, O, NH, NMe, S, SO.sub.3 M, PO.sub.3 HM, PO.sub.3 M.sub.2, SH, SR.sub.7, P(O)(OR.sub.5)(OR.sub.6), P(O)(OR.sub.6)(OM), P(O)(OR.sub.6)(R.sub.6), P(O)(OM)R.sub.6, SO.sub.2 M, S(O)R.sub.6, S(O).sub.2 R.sub.9, S(O)OR.sub.8 or S(O).sub.2 OR.sub.9 ;
- Y is SR.sub.4, SR.sub.10, SSR.sub.10, SO.sub.2 M, SO.sub.3 M, PO.sub.3 HM, PO.sub.3 M.sub.2, P(0)(OR.sub.5)(OM), or P(O)(OR.sub.5)(OR.sub.6), or does not exist;
- R.sub.5, R.sub.6, R.sub.8. R.sub.9, R.sub.10, are the same or different alkyls containing 1-12 carbon atoms or C.sub.1 or C.sub.2 connections to R.sub.1 or R.sub.3 in cyclic derivatives;
- R.sub.7 is C.sub.1 -C.sub.8, alkyl or acyl;
- R.sub.2 and R.sub.4 are the same or different and selected from H, ONO.sub.2, C.sub.1 -C.sub.4 alkyl optionally bearing 1-3 nitrate groups, and acyl groups (--C(O)R.sub.10);
- R.sub.1 and R.sub.3 are the same or different and selected from H, C.sub.1 -C.sub.4 alkyl and chains, which may include one O, linking R.sub.1 and R.sub.3 to form pentosyl, hexosyl, cyclopentyl or cycohexyl rings, which rings optionally bear hydroxyl substituents;
- and
- M is H, Na.sup.+, K.sup.+, NH.sub.4.sup.+ or N.sup.+ H.sub.n R.sub.11(4-n, where n is 0-3;
- and
- with the proviso that, when R.sub.6 is an alkyl group, and R.sub.1, R.sub.2 and R.sub.4 .dbd.H, R.sub.3 is not H or methyl;
- in admixture with a physiologically acceptable carrier therefor.
8 more elements
Dependencies are inferred from the claim text.