Ascorbic acid derivatives
AssigneeMerrell Dow Pharmaceuticals Inc.
InventorsGilbert Marciniak, J. Martin Grisar
Life of this patent
Estimating the term…
Abstract
Derivatives of 3,4-dihydroxy-2,5-dihydrofuran-5-ones, intermediates and processes useful for their preparation are disclosed. These compounds are useful as free-radical scavengers and exhibit cellular protective properties.
Claims16
A compound of the formula ##STR7## the enantiomers and mixtures thereof, the inner salts and the pharmaceutically acceptable salts thereof wherein
- Q is NR.sub.4 R.sub.5 or N.sup..sym. R.sub.4 R.sub.5 R.sub.6 .multidot.X.sup..crclbar., n is an integer 1 to 4,
- X is a halide or OS(O).sub.2 R.sub.7, with R.sub.7 being C.sub.1-6 alkyl, (CH.sub.2).sub.m -Z substituted phenyl wherein m is 0,1,2,3 or 4 and Z is H, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or nothing when R.sub.2 is nothing thereby forming the inner salt,
- R.sub.1 is H or C.sub.1-20 alkyl,
- R.sub.2 is H, C.sub.1-20 alkyl, or nothing when the inner salt is formed,
- R.sub.3 is H, or OH, and each of
- R.sub.4, R.sub.5 and R.sub.6 are C.sub.1-6 alkyl, (CH.sub.2).sub.x aryl or (CH.sub.2).sub.x halogenated aryl, x being zero, or 1 to 6, with the proviso that when n is one and Q is NR.sub.4 R.sub.5, then one of R.sub.1 or R.sub.2 is other than H.
A process for treating tissues subject to reperfusion damage in a subject which comprises administering a pharmaceutically effective amount of a compound of the formula ##STR8## the enantiomers and mixtures thereof, the inner salts and the pharmaceutically acceptable salts thereof wherein
- Q is NR.sub.4 R.sub.5 or N.sup..sym. R.sub.4 R.sub.5 R.sub.6 .multidot.X.sup..crclbar., n is an integer 1 to 4,
- X is a halide or OS(O).sub.2 R.sub.7, with R.sub.7 being C.sub.1-6 alkyl, (CH.sub.2).sub.m -Z substituted phenyl wherein m is 0,1,2,3 or 4 and Z is H, C.sub.1-6 alkyl, C.sub.1-6 alkoxy or halogen, or nothing when R.sub.2 is hydrogen,
- R.sub.1 is H or C.sub.1-20 alkyl,
- R.sub.2 is H, C.sub.1-20 alkyl, or nothing when the inner salt is formed,
- R.sub.3 is H, or OH, and each of
- R.sub.4, R.sub.5 and R.sub.6 are C.sub.1-6 alkyl, (CH.sub.2).sub.x aryl or (CH.sub.2).sub.x halogenated aryl, x being zero, or 1 to 6, with the proviso that when n is one and Q is NR.sub.4 R.sub.5, then one of R.sub.1 or R.sub.2 is other than H.
Dependencies are inferred from the claim text.