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US 2017/0246195 A1Published application
Mitoquinone derivatives used as mitochondrially targeted antioxidants
AssigneeAntipodean Pharmaceuticals, Inc.
InventorsKenneth Martin Taylor, Robin A.J. Smith
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Abstract
This invention relates to pharmaceutically acceptable amphiphilic antioxidant compounds, compositions and dosage forms comprising said compounds and methods and uses reliant on said compounds. The exemplified compounds are all mitoquinone derivatives, being methoxyphenyl alkyl triphenylphosphonium or methoxy dioxocyclohexadiene alkyl triphenylphosphonium derivatives. The compounds, compositions, dosage forms, uses and methods are useful in, for example, the treatment of diseases or conditions associated with oxidative stress.
Claims23
A chemically stable antioxidant compound, comprising:
- a lipophilic cationic moiety linked by a linking moiety to an antioxidant moiety;
- and
- an anionic complement for said cationic moiety,
- wherein the cationic moiety is capable of mitochondrially targeting the antioxidant moiety and is selected from the group consisting of a substituted or unsubstituted triphenylphosphonium cation, tribenzylammonium cation and phosphonium cation,
- wherein the linking moiety has a length equivalent to a linear saturated carbon chain of from 1 to 30 carbon atoms and comprises a straight alkylene chain, a substituted carbon chain or a branched carbon chain,
- wherein the antioxidant moiety is selected from the group consisting of (i) a quinone or a quinol, (ii) vitamin E or a vitamin E derivative, (iii) a chain breaking antioxidant, (iv) a derivatized fullerene, (v) a spin trap, (vi) butylated hydroxyanisole, (vii) butylated hydroxytoluene, (viii) 5,5-dimethylpyrroline-N-oxide, (ix) tert-butylnitrosobenzene, (x) tert-nitrosobenzene and (xi) α-phenyl-tert-butylnitrone,
- wherein the anionic complement is a pharmaceutically acceptable anion that is not nucleophilic and is not a halogen ion or a nitrate anion, and is selected from the group consisting of an alkyl sulfonate, an aryl sulfonate, tetrafluoroborate, trifluoromethanesulfonate, hexafluoroantimonate, hexafluoroarsenate, hexafluorophosphate, tetraphenylborate, and tetra(perfluorophenyl)borate, and
- wherein said anionic complement does not exhibit reactivity against the antioxidant moiety, the cationic moiety or the linking moiety.
5 more elements
Dependencies are inferred from the claim text.