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US 9,957,214 B2Granted
Multifunctional radical quenchers
AssigneeArizona Board of Regents on behalf of Arizona State University
InventorsManikandadas Mathilakathu Madathil, Omar Khdour, Sidney Hecht
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Abstract
The invention provides a compound of formula (I): [insert formula (I)] wherein X, Y, and R1-R4 have any of the values defined in the specification, and salts thereof, as well as compositions comprising the compounds or salts. The compounds are useful for treating diseases associated with impaired mitochondrial function in an animal.
Claims8
A compound of formula Ib:
- wherein:
- R2 is H, cyano, nitro, halo, aryloxy, —OC1-C20alkyl, —OC2-C20alkenyl, —OC2-C20alkynyl, —NRbRc, —C(═O)NRbRc, or —C(═O)ORd;
- Y and R3 taken together are H, cyano, nitro, halo, aryloxy, —OC1-C20alkyl, —NRa(C1-C20alkyl), —NRa(aryl), —C1-C20alkyl, —C2-C20alkenyl, or —C2-C20alkynyl;
- R4 is a C1-C20alkyl, C2-C20alkenyl, or C2-C20alkynyl;
- Ra is H, C1-C20alkyl, C2-C20alkenyl, C2-C20alkynyl, or C1-C20alkanoyl;
- Rx is C1-C16alkyl, C2-C16alkenyl, C2-C16alkynyl, aryl, —OC1-C16alkyl, —OC2-C16alkenyl, —OC2-C16alkynyl, aryloxy, —N(H)C1-C16alkyl, —N(H)C2-C16alkenyl, —N(H)C2-C16alkynyl, or —N(H)aryl;
- or a salt thereof.
4 more elements
A compound selected from:
- and salts thereof.
A compound selected from:
A compound of formula I:
- wherein:
- X is NRa or —C(═O)N(Ra)—;
- Ra is H or methyl;
- R1 is a C1-C20 straight or branched, saturated or unsaturated carbon chain, wherein one or more carbon atoms can optionally be replaced with —O—, —NH—, a divalent phenyl group, or a divalent C3-C6cycloalkyl group;
- wherein R1 can be optionally substituted with one or more groups independently selected from halo, aryl, and oxo (═O);
- R2 is H or methyl;
- Y and R3 taken together are methoxy, 3-(tert-butoxycarbonyl)prop-1-yloxy, N-(3-(butoxycarbonyl)prop-1-yl)amino, N-(3-(hexyloxycarbonyl)prop-1-yl)amino, 3-(butoxycarbonyl)prop-1-yloxy, or 3-(hexyloxycarbonyl)prop-1-yloxy;
- and
- R4 is tridecyl, hexadecyl, or 10-undecen-1-yl;
- or a salt thereof;
- provided the compound is not:
8 more elements
A compound of formula I:
- wherein:
- X is NRa, or —C(═O)N(Ra)—;
- R1 is a C1-C20 straight or branched, saturated or unsaturated carbon chain, wherein one or more carbon atoms can optionally be replaced with —O—, —NH—, a divalent phenyl group, or a divalent C3-C6cycloalkyl group;
- wherein R1 can be optionally substituted with one or more groups independently selected from halo, aryl, and oxo (═O);
- R2 is H,
- Y is O,
- R3 is aryl, or a C1-C20 straight or branched, saturated or unsaturated carbon chain other than methyl;
- R4 is a C1-C20 straight or branched, saturated or unsaturated carbon chain, wherein one or more carbon atoms can optionally be replaced with a divalent phenyl group, or a divalent C3-C6cycloalkyl group;
- wherein R4 can be further optionally substituted with one or more groups independently selected from halo, oxo (═O), carboxy, C1-C3alkyl, C1-C3alkoxy, nitro, —SO3H, or tetrazolyl;
- or R1 and R4 taken together form a C3-C18 straight or branched, saturated or unsaturated carbon chain that can be optionally substituted with one or more groups independently selected from halo and oxo (═O);
- and
- Ra is H;
- or a salt thereof.
10 more elements
Dependencies are inferred from the claim text.