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US 7,829,713 B2Granted
Therapeutic piperazines
AssigneeHelicon Therapeutics, Inc.
InventorsTerrence P. Keenan, Alan P. Kaplan
Life of this patent
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Abstract
The invention includes a compound of formula I: wherein R1, X, Z, n, and m have any of the values described herein, as well as salts of such compounds, compositions comprising such compounds, and therapeutic methods that comprise the administration of such compounds. The compounds are inhibitors of PDE4 function and are useful for improving cognitive function in animals.
Claims3
A compound of formula I:
- wherein:
- R1 is H, (C1-C6)alkyl, aryl, aryl(C1-C6)alkyl, indolyl;
- n is 1;
- m is 1;
- W is O or two hydrogens;
- X is N—Y—R4;
- Y is a direct bond or CH2;
- R4 is H, (C1-C6)alkyl, (C1-C6)alkoxy, (C1-C6)alkanoyl, hydroxy, (C1-C6)alkoxycarbonyl, carboxy, aryl, or aryl(C1-C6)alkyl;
- Z has the following formula:
- wherein R2 is methyl and R3 is cyclopropyl or cyclopentyl;
- wherein the ring containing X is optionally substituted on carbon with one or more halo, (C1-C6)alkyl, or (C1-C6)alkoxy;
- or a pharmaceutically acceptable salt thereof;
- and
- wherein if R1 is H, R4 cannot be aryl(C1-C6)alkyl.
11 more elements
A compound selected from the group consisting of:
- (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine;
- (2S,5S)-5-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-2-methyl-piperazine;
- (2R,5S)-5-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-2-methyl-piperazine;
- (R)-6-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-2-one;
- (S)-6-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-2-one;
- (R)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine;
- (S)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-phenethyl-piperazine;
- (R)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-phenethyl-piperazine;
- (S)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-(3-phenyl-propyl)-piperazine;
- (S)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-naphthalen-1-ylmethyl-piperazine;
- (S)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-naphthalen-2-ylmethyl-piperazine;
- (R)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-phenyl-piperazine;
- (S)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-isopropyl-piperazine;
- (S)-1-(3-Cyclopentyloxy-4-methoxy-phenyl)-3-isobutyl-piperazine;
- 1-(3-Cyclopentyloxy-4-methoxy-phenyl)-piperazine;
- (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-1-methyl-piperazine;
- (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-1-ethyl-piperazine;
- (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-1-benzyl-piperazine;
- 1-[(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-ethanone;
- (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carboxylic acid ethyl ester;
- [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid methyl ester;
- and
- [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid.
20 more elements
A compound selected from the group consisting of:
- (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine;
- and
- [(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazin-1-yl]-acetic acid;
- or a pharmaceutically acceptable salt thereof.
1 more element
Dependencies are inferred from the claim text.