IP Library › Granted Patent US 7,847,101

Granted Patent B2

US 7,847,101 · App. 10/521,948 · Granted Dec 7, 2010

Pyrazolylbenzothiazole derivatives and their use as therapeutic agents

Assignee: Valocor Therapeutics, Inc.

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Quick Facts

Patent No.: US 7,847,101
App. No.: 10/521,948
Granted: Dec 7, 2010
Kind: B2

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Abstract

Pharmaceutical pyrazolybenzothiazole compositions of formula (1) are provided. The compositions may be pharmaceutically acceptable salts. R 1 , R 2 and R 3 at each occurrence are independently selected from amino, aminosulfinyl, aminosulfonyl, aryl, azido, halogen, heteroalkyl, heteroaryl, hydrazinyl, hydrocarbyl, hydrogen, hydroxyl, nitro, nitroso, phosphate, phosphinate, phosphonate, phosphonium, phosphorothioate, phosphoryl, sulfamoyl, sulfate, sulfinic acid, sulfonamido, sulfonate, sulfonic acid, sulfonyl, sulfoxido, thiol, thioureido, and ureido, and R 4 is selected from hydrogen, heteroalkyl, heteroaryl, and hydrocarbyl.

Claims (447)

1. A compound of formula (1):

as a single tautomer, a mixture of tautomers, a single stereoisomer, a mixture of stereoisomers, or a racemic mixture; or a pharmaceutically acceptable salt thereof; wherein:

R 1 at each occurrence is independently selected from amino, aminosulfinyl, aminosulfonyl, aryl, azido, halogen, heteroalkyl, heteroaryl, hydrazinyl, hydrocarbyl, hydrogen, hydroxyl, nitro, nitroso, phosphate, phosphinate, phosphonate, phosphonium, phosphorothioate, phosphoryl, sulfamoyl, sulfate, sulfinic acid, sulfonamido, sulfonate, sulfonic acid, sulfoxido, thiol, thioureido, and ureido;

R 2 is amino, aminosulfinyl, aminosulfonyl, azido, halogen, heteroaryl, hydrazinyl, hydroxyl, nitro, nitroso, phosphate, phosphinate, phosphonate, phosphonium, phosphorothioate, phosphoryl, sulfamoyl, sulfate, sulfinic acid, sulfonamido, sulfonate, sulfonic acid, sulfoxido, thiol, thioureido, or ureido;

R 3 is selected from heterocycle, halogen-substituted hydrocarbyl and hydrocarbyl; and

R 4 is selected from hydrogen, heteroalkyl, heteroaryl, and hydrocarbyl.

2. A compound of formula (1):

as a single tautomer, a mixture of tautomers, a single stereoisomer, a mixture of stereoisomers, or a racemic mixture; or a pharmaceutically acceptable salt thereof; wherein:

R 2 is amino;

R 3 is selected from hydrocarbyl, —O-hydrocarbyl and —S-hydrocarbyl; and

R 4 is selected from hydrogen, heteroalkyl, heteroaryl, and hydrocarbyl.

3. A compound of formula (2):

as a single tautomer, a mixture of tautomers, a single stereoisomer, a mixture of stereoisomers, or a racemic mixture; or a pharmaceutically acceptable salt thereof; wherein:

R 4 is selected from hydrogen, heteroalkyl, heteroaryl, and hydrocarbyl; and

R 5 , R 6 , R 7 and R 8 at each occurrence is independently selected from heteroalkyl, heteroaryl, hydrocarbyl and hydrogen, with the proviso that R 7 and R 8 may join together to form a heterocyclic ring including the nitrogen to which they are both bonded, and that R 1 , R 5 , R 6 , R 7 and R 8 are not all hydrogens, and wherein the compound of Formula (2) is not 1H-pyrazole-3,5-diamine, 4-(2-benzothiazolyl)-N 3 -(4-methylphenyl); or 1H-pyrazole-3,5-diamine, 4-(2-benzothiazolyl)-N 3 -phenyl.

4. A pharmaceutical composition comprising a pharmaceutically acceptable excipient and a compound selected from the group consisting of:

(4-Benzothiazol-2-yl-1H-pyrazol-3-yl)-[2-(1H-imidazol-4-yl)-ethyl]-amine;

(4-Benzothiazol-2-yl-2H-pyrazol-3-yl)-methyl-amine;

[2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazol-6-yl]-methanol;

[2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-5-yl]-methanol;

[2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-6-yl]-methanol;

2-(1H-Pyrazol-4-yl)-benzothiazole-6-sulfonic acid amide;

2-(3-Amino-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-6-sulfonic acid amide;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-4,5,6-trifluoro-benzothiazole-7-sulfonic acid amide;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-6-carboxylic acid methyl ester;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-6-sulfonic acid methylamide;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-benzothiazole-6-carboxylic acid;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-benzothiazole-6-carboxylic acid methyl ester;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid methylamide;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2,6-dimethyl-pyrimidin-4-yl)-amide;

2-(3-Amino-5-methyl-1H-pyrazol-4-yl)-benzothiazole-7-carboxylic acid methyl ester;

2-(3-Methyl-1H-pyrazol-4-yl)-benzothiazole;

2-(4-Benzothiazol-2-yl-1H-pyrazol-3-yl)-phenol;

2-(5-Amino-1H-pyrazol-4-yl)-benzothiazol-6-ylamine;

2-(5-Amino-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid methylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-4-fluorobenzothiazole-6-sulfonic acid amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-4-sulfonic acid (2-hydroxy-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-6-sulfonic acid amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-6-sulfonic acid (2-hydroxy-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-5-fluoro-benzothiazole-6-sulfonic acid (pyridin-4-ylmethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-5-ol;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-5-sulfonic acid methylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-carboxylic acid amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2-hydroxy-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2-methoxy-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid 4-fluoro-benzylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2-thiophen-2-yl-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid 4-chloro-benzylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid 4-methoxy-benzylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid benzylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid phenethyl-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid [2-(4-amino-phenyl)-ethyl]-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2-morpholin-4-yl-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2,2,2-trifluoro-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid cyclopropylmethyl-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid [2-(3H-imidazol-4-yl)-ethyl]-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid 4-amino-benzylamide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (pyridin-4-ylmethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (2-dimethylamino-ethyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid (3-dimethylamino-propyl)-amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid(acetic hydrazido)amide;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid(phenylhydrazino)amide;

2-(5-Amino-3-pyridin-4-yl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonic acid amide;

2-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-ethanol;

2-(5-Amino-4-benzothiazol-2-yl-2H-pyrazol-3-ylamino)-cyclopentanol;

2-{[2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-6-ylmethyl]-amino}-ethanol;

3-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-propan-1-ol;

3-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-propan-1-ol;

3-[5-Amino-4-(5-fluoro-6-methoxy-benzothiazol-2-yl)-1H-pyrazol-3-ylamino]-propan-1-ol;

3-{[2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-6-ylmethyl]-amino}-benzenesulfonamide;

4-(4-Benzothiazol-2-yl-1H-pyrazol-3-yl)-benzene-1,3-diol; 4-(4-Benzothiazol-2-yl-1H-pyrazol-3-yl)-phenol;

4-(4-fluorobenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-butan-1-ol;

4-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-butan-1-ol;

4-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-butyric acid;

4-(5-Amino-4-benzothiazol-2-yl-2H-pyrazol-3-ylamino)-N-thiazol-2-yl-benzenesulfonamide;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(2-fluoro-phenyl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(2-phenyl-cyclopropyl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(3-fluoro-phenyl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(3-nitro-phenyl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(4-fluoro-phenyl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(4-methoxy-phenyl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-(5-nitro-furan-2-yl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-furan-2-yl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-isoxazol-5-yl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-phenyl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-piperazin-1-yl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-pyridin-4-yl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-5-thiophen-2-yl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methoxy-benzothiazol-2-yl)-N 3 -[2-(3H-imidazol-4-yl)-ethyl]-1H-pyrazole-3,5-diamine;

4-(5-Fluoro-6-methyl-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

4-(5-Fluoro-6-methyl-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(5-Fluoro-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(5-Methoxy-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(5-Trifluoromethyl-benzothiazol-2-yl)-1H-pyrazol-3-ylamine;

4-(6-Bromo-5-fluoro-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-(6-Bromo-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-(6-Chlorobenzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(6-Dimethylaminomethyl-5-fluoro-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-(6-Dimethylaminomethyl-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(6-Fluoro-benzothiazol-2-yl)-1H-pyrazol-3-ylamine;

4-(6-Fluoro-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-(6-Methanesulfonyl-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(6-Methoxy-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-(6-Methoxy-benzothiazol-2-yl)-5-piperazin-1-yl-2H-pyrazol-3-ylamine;

4-(6-Nitro-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

4-(7-chloro-4-methoxy-benzothiazol-2-yl)-5-methyl-2H-pyrazol-3-ylamine;

4-(7-Chloro-5-fluoro-6-methoxy-benzothiazol-2-yl)-5-methyl-1H-pyrazol-3-ylamine;

4-[(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-methyl]-benzenesulfonamide;

4-[2-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-ethyl]-phenol;

4-Benzothiazol-2-yl-5-(3-dimethylamino-propyl)-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-(3-methylamino-propyl)-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-(4-dimethylamino-butyl)-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-(4-methylamino-butyl)-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-(4-nitro-phenyl)-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-cyclopropyl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-ethyl-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-furan-2-yl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-methyl-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-methylsulfanyl-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-phenyl-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-piperazin-1-yl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-piperidin-4-yl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-pyridin-3-yl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-pyridin-4-yl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-pyrrolidin-1-yl-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-thiophen-2-yl-2H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-N 3 -(1H-imidazol-2-ylmethyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(1H-imidazol-2-ylmethylene)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(2-dimethylamino-ethyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(2-ethylamino-ethyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(2-methoxy-ethyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(2-pyrrolidin-1-yl-ethyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(3-dimethylamino-propyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(3-imidazol-1-yl-propyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -[2-(1H-indol-3-yl)-ethyl]-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -piperidin-4-ylmethyl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -(2-morpholin-4-yl-ethyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -ethyl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -pyridin-3-ylmethyl-1H-pyrazole-3,5-diamine;

5-(2-Chloro-pyridin-3-yl)-4-(5-fluoro-6-methoxy-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

5-(3-Amino-propyl)-4-benzothiazol-2-yl-2H-pyrazol-3-ylamine;

5-(4-Amino-phenyl)-4-benzothiazol-2-yl-2H-pyrazol-3-ylamine;

5-Cyclopropyl-4-(5-fluoro-6-methoxy-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

5-Methyl-4-(4,5,6-trifluoro-benzothiazol-2-yl)-1H-pyrazol-3-ylamine;

5-Methyl-4-(5-trifluoromethylbenzothiazol-2-yl)-1H-pyrazol-3-ylamine;

5-Methyl-4-(6-methylaminomethyl-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

5-Methyl-4-(6-morpholin-4-ylmethyl-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

5-Methyl-4-(6-pyrrolidin-1-ylmethyl-benzothiazol-2-yl)-2H-pyrazol-3-ylamine;

5-Methyl-4-[6-(4-methyl-piperazin-1-ylmethyl)-benzothiazol-2-yl]-2H-pyrazol-3-ylamine;

5-Methyl-4-[6-(4-methyl-piperazine-1-sulfonyl)-benzothiazol-2-yl]-2H-pyrazol-3-ylamine;

N-[2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazol-6-yl]-acetamide;

N-[2-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-ylamino)-ethyl]-acetamide;

N-[4-(5-Amino-4-benzothiazol-2-yl-1H-pyrazol-3-yl)-phenyl]-hydroxylamine;

N-{2-[2-(5-Amino-3-methyl-1H-pyrazol-4-yl)-benzothiazole-6-sulfonylamino]-ethyl}-acetamide;

N-{2-[5-Amino-4-(5-fluoro-6-methoxy-benzothiazol-2-yl)-1H-pyrazol-3-ylamino]-ethyl}-acetamide;

N 3 -(2-Amino-ethyl)-4-benzothiazol-2-yl-1H-pyrazole-3,5-diamine;

N 3 -(2-Dimethylamino-ethyl)-4-(5-fluoro-6-methoxy-benzothiazol-2-yl)-1H-pyrazole-3,5-diamine;

N 3 -(3-Dimethylamino-propyl)-4-(5-fluoro-6-methoxy-benzothiazol-2-yl)-1H-pyrazole-3,5-diamine;

N 3 -(4-Amino-phenyl)-4-benzothiazol-2-yl-1H-pyrazole-3,5-diamine;

N 3 -[2-(3H-Imidazol-4-yl)-ethyl]-4-(6-methoxy-benzothiazol-2-yl)-1H-pyrazole-3,5-diamine;

2-(5-Amino-3-methyl-1H-pyrazol-4-yl)benzothiazole-5-carboxylic acid ethyl ester;

4-Benzothiazol-2-yl-N 5 -benzyl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-5-morpholin-4-yl-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-5-(4-methylpiperazin-1-yl)-1H-pyrazol-3-ylamine;

4-Benzothiazol-2-yl-N 5 -(3,5-dichlorophenyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -(3-trifluoromethanesulfonyl-phenyl)-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -quinolin-6-yl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -quinolin-5-yl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -pyridin-3-yl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 5 -pyridin-4-ylmethyl-1H-pyrazole-3,5-diamine;

4-Benzothiazol-2-yl-N 3 -(3-methylbutyl)-1H-pyrazole-3,5-diamine;

2-(3-Phenyl-1H-pyrazol-4-yl)benzothiazole;

2-[3-(4-Methoxyphenyl)-1H-pyrazol-4-yl]benzothiazole;

2-[3-(2-Methoxyphenyl)-1H-pyrazol-4-yl]benzothiazole; and

4-Benzothiazol-2-yl-2-methyl-2H-pyrazol-3-ylamine;

as a single tautomer, a mixture of tautomers, a single stereoisomer, a mixture of stereoisomers, or a racemic mixture; or a pharmaceutically acceptable salt thereof.

5. A compound selected from the group consisting of: