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US 2014/0154192 A1Published application
Glutathione analogs and uses thereof
AssigneeRegents of the University of Minnesota
InventorsRobert Vince, Swati Sudhakar More
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Abstract
The invention provides compounds of formula (I): (I) or salts thereof, wherein R1, R2, R3 Z, and X have any of the values defined herein, as well as compositions comprising such compounds. The compounds and compositions are useful for treating neurodegenerative disorders.
Claims49
A compound of formula I:
- wherein:
- each R1 is independently H, (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl, or heteroaryl(C1-C6)alkyl;
- each R1a is independently H, (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl, or heteroaryl(C1-C6)alkyl;
- R2 is OH, NH2, —O—C(C═O)—R1a, —NH—C(C═O)—R1a or —NH—C(C═O)O—R1a;
- Z is —CH2—, —NH—, —O—, or —S—;
- X is —S— or absent, R3 is H, (C1-C6)alkyl, —(CH2)CH(NHR6)CO2H or
- and R7 is H;
- or X is absent, and R3 and R7 together with the atoms to which they are attached form a heterocycle, wherein the heterocycle is optionally substituted with one or more groups selected from oxo (═O), (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl and heteroaryl(C1-C6)alkyl;
- each R4 is independently H, (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl, or heteroaryl(C1-C6)alkyl;
- R5 is OH, NH2, —O—C(C═O)—R1a, —NH—C(C═O)—R1a or —NH—C(C═O)O—R1a;
- R6 is H, (C1-C6)alkyl or —C(C═O)—R1;
- and
- Y is —CH2—, —O—, —S— or NH;
- or a salt thereof;
- provided the compound of formula I is not a compound of formula:
12 more elements
A method for treating Alzheimer's Disease, amyotrophic lateral sclerosis (ALS), diabetes, acetaminophen toxicity or stroke in a mammal, comprising administering a compound of formula (I):
- wherein:
- each R1 is independently H, (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl, or heteroaryl(C1-C6)alkyl;
- each R1a is independently H, (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl, or heteroaryl(C1-C6)alkyl;
- R2 is OH, NH2, —O—C(C═O)—R1a, —NH—C(C═O)—R1a or —NH—C(C═O)O—R1a;
- Z is —CH2—, —NH—, —O—, or —S—;
- X is —S— or absent, R3 is H, (C1-C6)alkyl, —(CH2)CH(NHR6)CO2H or
- and R7 is H;
- or X is absent, and R3 and R7 together with the atoms to which they are attached form a heterocycle, wherein the heterocycle is optionally substituted with one or more groups selected from oxo (═O), H, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl and heteroaryl(C1-C6)alkyl;
- each R4 is independently H, (C1-C6)alkyl, (C3-C8)cycloalkyl, aryl(C1-C6)alkyl, or heteroaryl(C1-C6)alkyl;
- R5 is OH, NH2, —O—C(C═O)—R1a, —NH—C(C═O)—R1a or —NH—C(C═O)O—R1a;
- R6 is H, (C1-C6)alkyl or —C(C═O)—R1;
- and
- Y is —CH2—, —O—, —S— or NH;
- or a pharmaceutically acceptable salt thereof to the mammal.
11 more elements
Dependencies are inferred from the claim text.