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US 7,232,929 B2Granted
Amide derivatives of 2,2,3,3-tetramethylcyclopropane carboxylic acid
AssigneeYissum Research Development Company of the Hebrew University of Jerusalem
InventorsMeir Bialer, Boris Yagen, Eyal Sobol, Dan Kaufmann
Life of this patent
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Abstract
The invention relates to new 2,2,3,3-tetramethylcyclopropane carboxamide derivative compounds, pharmaceutical compositions thereof and uses thereof for treating psychotic disorders, neurodegenerative diseases, epilepsy and pain.
Claims25
A 2,2,3,3-tetramethylcyclopropane carboxamide derivative compound of formula I:
- including enantiomers, hydrates, solvates and pharmaceutically acceptable salts thereof
- wherein,
- R1 is hydrogen or C1–C6 alkyl group and
- R2 is selected from the group consisting of:
- (a) a member having the structural formula:
- —C(═O)—(CH2)n—NR3R4
- wherein n=0–6, R3 and R4 are the same or different and are independently selected from the group consisting of hydrogen, C1–C6alkyl group, an acyl group having the formula RC(═O)—, wherein R is a C1–C6alkyl group, and a keto group having the formula RC(═O)R′—, wherein R and R′ are C1–C6alkyl groups which may be the same or different;
- (b) a C1–C6alkyl sulfonamide group;
- (c) an (N—C1–C6alkyl)C1–C6alkyl sulfonamide group;
- (d) an aryl sulfonamide group;
- (e) a thiadiazole sulfonamide group;
- (f) a C1–C6alkyl-thiadiazole sulfonamide group;
- (g) an (N—C1–C6alkyl)aryl sulfonamide group;
- (h) an (N—C1–C6alkyl)C1–C6alkyl aryl sulfonamide group;
- (i) an (N—C1–C6alkyl)thiadiazole sulfonamide group;
- (j) an (N—C1–C6alkyl)C1–C6alkyl-thiadiazole sulfonamide group;
- and
- (k) a C1–C6alkoxy group.
15 more elements
A 2,2,3,3-tetramethylcyclopropane carboxamide derivative compound of formula I:
- including enantiomers, hydrates, solvates and pharmaceutically acceptable salts thereof
- wherein,
- R1 is C1–C6 alkyl group and
- R2 is selected from the group consisting of:
- (a) a member having the structural formula:
- —C(═O)—(CH2)n—NR3R4
- wherein n=0–6, R3 and R4 are the same or different and are independently selected from the group consisting of hydrogen, C1–C6alkyl group, an acyl group having the formula RC(═O)—, wherein R is a C1–C6alkyl group, and a keto group having the formula RC(═O)R′—, wherein R and R′ are C1–C6alkyl groups which may be the same or different;
- (b) a C1–C6alkyl sulfonamide group;
- (c) an (N—C1–C6alkyl)C1–C6alkyl sulfonamide group;
- (d) an aryl sulfonamide group;
- (e) a C2–C6alkyl aryl sulfonamide group;
- (f) a thiadiazole sulfonamide group;
- (g) a C1–C6alkyl-thiadiazole sulfonamide group;
- (h) an (N—C1–C6alkyl)aryl sulfonamide group;
- (i) an (N—C1–C6alkyl)C1–C6alkyl aryl sulfonamide group;
- (j) an (N—C1–C6alkyl)thiadiazole sulfonamide group;
- (k) an (N—C1–C6alkyl)C1–C6alkyl-thiadiazole sulfonamide group;
- and
- (l) a C1–C6alkoxy group.
16 more elements
A pharmaceutical composition comprising as an active ingredient a therapeutically effective amount of at least one compound of formula I:
- including enantiomers, hydrates, solvates and pharmaceutically acceptable salts thereof
- wherein,
- R1 is hydrogen or C1–C6 alkyl group and
- R2 is selected from the group consisting of:
- (a) a member having the structural formula:
- —C(═O)—(CH2)n—NR3R4
- wherein n=0–6, R3 and R4 are the same or different and are independently selected from the group consisting of hydrogen, C1–C6alkyl group, an acyl group having the formula RC(═O)—, wherein R is a C1–C6alkyl group, and a keto group having the formula RC(═O)R′—, wherein R and R′ are C1–C6alkyl groups which may be the same or different;
- (b) a C1–C6alkyl sulfonamide group;
- (c) an (N—C1–C6alkyl)C1–C6alkyl sulfonamide group;
- (d) an aryl sulfonamide group;
- (e) a thiadiazole sulfonamide group;
- (f) a C1–C6alkyl-thiadiazole sulfonamide group;
- (g) an (N—C1–C6alkyl)aryl sulfonamide group;
- (h) an (N—C1–C6alkyl)C1–C6alkyl aryl sulfonamide group;
- (i) an (N—C1–C6alkyl)thiadiazole sulfonamide group;
- (j) an (N—C1–C6alkyl)C1–C6alkyl-thiadiazole sulfonamide group;
- and
- (k) a C1–C6alkoxy group and a pharmaceutically acceptable carrier.
15 more elements
A method of treating or ameliorating a medical condition selected from psychotic disorders, neurodegenerative diseases, epilepsy and pain, in a mammal in need of such treatment comprising administering to the mammal an effective amount of a compound of formula I:
- including enantiomers, hydrates, solvates and pharmaceutically acceptable salts thereof
- wherein,
- R1 is hydrogen or C1–C6 alkyl group and
- R2 is selected from the group consisting of:
- (a) a member having the structural formula:
- —C(═O)—(CH2)n—NR3R4
- wherein n=0–6, R3 and R4 are the same or different and are independently selected from the group consisting of hydrogen, C1–C6alkyl group, an acyl group having the formula RC(═O)—, wherein R is a C1–C6alkyl group, and a keto group having the formula RC(═O)R′—, wherein R and R′ are C1–C6alkyl groups which may be the same or different;
- (b) a C1–C6alkyl sulfonamide group;
- (c) an (N—C1–C6alkyl)C1–C6alkyl sulfonamide group;
- (d) an aryl sulfonamide group;
- (e) a C2–C6alkyl aryl sulfonamide group;
- (f) a thiadiazole sulfonamide group;
- (g) a C1–C6alkyl-thiadiazole sulfonamide group;
- (h) an (N—C1–C6alkyl)aryl sulfonamide group;
- (i) an (N—C1–C6alkyl)C1–C6alkyl aryl sulfonamide group;
- (j) an (N—C1–C6alkyl)thiadiazole sulfonamide group;
- (k) an (N—C1–C6alkyl)C1–C6alkyl-thiadiazole sulfonamide group;
- and
- (l) a C1–C6alkoxy group.
16 more elements
Dependencies are inferred from the claim text.