e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and Potential Antipsychotic Activity of 1H-Imidazo [1, 2-c] pyrazolo [3, 4-e] pyrimidines

HA DeWald, NW Beeson, FM Hershenson…

Index: DeWald; Beeson; Hershenson; Wise; Downs; Heffner; Coughenour; Pugsley Journal of Medicinal Chemistry, 1988 , vol. 31, # 2 p. 454 - 461

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Citation Number: 18

Abstract

In previous papers we described two series of compounds that lack dopamine antagonist activity and exhibit preclinical profiles suggestive of antipsychotic efficacy without extrapyramidal side effect p~ tential.~,~ As part of this continuing effort, we now report the investigation of a series of novel imidazopyrazolopyrimidines with preclinical effects that resemble those of antipsychotic drugs. This work was based, in part, on our earlier ...

4-acetamido-2,5-dimethylpyrazole-3-carboxamide Structure

4-acetamido-2,5...

~74%

1,3,5-trimethyl-4H-pyrazolo[4,3-d]pyrimidin-7-one Structure

1,3,5-trimethyl...

4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE Structure

4-AMINO-N,3-DIM...

~%

1,3,5-trimethyl-4H-pyrazolo[4,3-d]pyrimidin-7-one Structure

1,3,5-trimethyl...

1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE-5-CARBOXAMIDE Structure

1,3-DIMETHYL-4-...

~%

1,3,5-trimethyl-4H-pyrazolo[4,3-d]pyrimidin-7-one Structure

1,3,5-trimethyl...

1,3,5-trimethyl-4H-pyrazolo[4,3-d]pyrimidin-7-one Structure

1,3,5-trimethyl...

~96%

7-chloro-1,3,5-trimethylpyrazolo[4,3-d]pyrimidine Structure

7-chloro-1,3,5-...

4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE Structure

4-AMINO-N,3-DIM...

~%

7-chloro-1,3,5-trimethylpyrazolo[4,3-d]pyrimidine Structure

7-chloro-1,3,5-...

1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE-5-CARBOXAMIDE Structure

1,3-DIMETHYL-4-...

~%

7-chloro-1,3,5-trimethylpyrazolo[4,3-d]pyrimidine Structure

7-chloro-1,3,5-...

4-acetamido-2,5-dimethylpyrazole-3-carboxamide Structure

4-acetamido-2,5...

~%

7-chloro-1,3,5-trimethylpyrazolo[4,3-d]pyrimidine Structure

7-chloro-1,3,5-...

Ethanoic anhydride Structure

Ethanoic anhydride

4-AMINO-N,3-DIMETHYL-1H-PYRAZOLE-5-CARBOXAMIDE Structure

4-AMINO-N,3-DIM...

~87%

4-acetamido-2,5-dimethylpyrazole-3-carboxamide Structure

4-acetamido-2,5...

1,3-DIMETHYL-4-NITRO-1H-PYRAZOLE-5-CARBOXAMIDE Structure

1,3-DIMETHYL-4-...

~%

4-acetamido-2,5-dimethylpyrazole-3-carboxamide Structure

4-acetamido-2,5...

Aziridine Structure

7-chloro-1-ethyl-3,5-dimethylpyrazolo[4,3-d]pyrimidine Structure

7-chloro-1-ethy...

~90%

7-(aziridin-1-yl)-1-ethyl-3,5-dimethylpyrazolo[4,3-d]pyrimidine Structure

7-(aziridin-1-y...

N-(5-cyano-1,3-dimethyl-1H-pyrazol-4-yl)propanamide Structure

N-(5-cyano-1,3-...

~70%

5-ethyl-1,3-dimethyl-4H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-ethyl-1,3-dim...

4-amino-5-cyano-1,3-dimethyl pyrazole Structure

4-amino-5-cyano...

~%

5-ethyl-1,3-dimethyl-4H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-ethyl-1,3-dim...

7,8-dihydro-5-ethyl-1,3,8-trimethyl-1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidine Structure

7,8-dihydro-5-e...

~75%

5-ethyl-1,3,8-trimethyl-1H-imidazo[1,2-c]pyrazolo[3,4-e]pyrimidine Structure

5-ethyl-1,3,8-t...

2-Aminoethanol Structure

7-chloro-1-ethyl-3,5-dimethylpyrazolo[4,3-d]pyrimidine Structure

7-chloro-1-ethy...

~57%

2-[(1-ethyl-5-methylpyrazolo[4,3-d]pyrimidin-7-yl)amino]ethanol Structure

2-[(1-ethyl-5-m...

1,3-dimethyl-1,6-dihydro-pyrazolo[4,3-d]pyrimidin-7-one Structure

1,3-dimethyl-1,...

~%

7-Chloro-1,3-dimethyl-1H-pyrazolo[4,3-d]pyrimidine Structure

7-Chloro-1,3-di...

1,2-Ethanediamine Structure

1,2-Ethanediamine

1H-Pyrazole-5-carbonitrile,1,3-dimethyl-4-nitro- Structure

1H-Pyrazole-5-c...

~59%

5-(4,5-dihydro-1H-imidazol-2-yl)-1,3-dimethyl-4-nitropyrazole Structure

5-(4,5-dihydro-...

1,2-Ethanediamine Structure

1,2-Ethanediamine

4-amino-5-cyano-1,3-dimethyl pyrazole Structure

4-amino-5-cyano...

~65%

5-(4,5-dihydro-1H-imidazol-2-yl)-1,3-dimethylpyrazol-4-amine Structure

5-(4,5-dihydro-...