1421375-43-0

Basic information

• Product Name: 2-chloro-4-((3S,3aS,5S)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile
• CAS NO: 1421375-43-0
• Molecular Weight: 305.764
• Mol File: 1421375-43-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-chloro-4-((3S,3aS,5S)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-chloro-4-((3S,3aS,5S)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile(1421375-43-0)
• EPA Substance Registry System: 2-chloro-4-((3S,3aS,5S)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile(1421375-43-0)

Safety Data

• Hazardous Substances Data: 1421375-43-0(Hazardous Substances Data)

Upstream product

• 1421375-81-6 ((2S,4R)-4-(tert-butyldimethylsilyloxy)-1-nitrosopyrrolidin-2-yl)methanol 
• 1421375-80-5 (2S,4R)-methyl-4-(tert-butyldimethylsilyloxy)-1-nitrosopyrrolidine-2-carboxylate 
• 60096-51-7 (2S,4R)-methyl-4-hydroxy-1-nitrosopyrrolidine-2-carboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 1421375-86-1 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-formylpyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile 
• 1421375-84-9 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile 
• 1421375-82-7 ((2S,4R)-1-amino-4-(tert-butyldimethylsilyloxy)pyrrolidin-2-yl)methanol 
• 1297544-91-2 2-chloro-4-formyl-3-methylbenzonitrile 
• 757247-75-9 2-chloro-4-iodo-3-methylbenzonitrile 
• 1421375-33-8 2-chloro-4-((3S,3aS,5R)-5-hydroxy-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile 
• 1421375-98-5 4-((3S,3aR,5R)-5-(tert-butyldimethylsilyloxy)-3-methoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile 
• 1421375-88-3 4-((3S,3aR,5R)-5-(tert-butyldimethylsilyloxy)-3-hydroxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile 

Relevant articles and documents

3-Alkoxy-pyrrolo[1,2- b ]pyrazolines as selective androgen receptor modulators with ideal physicochemical properties for transdermal administration

We describe the synthesis and characterization of 3-alkoxy-pyrrolo[1,2-b]pyrazolines as novel selective androgen receptor (AR) modulators that possess excellent physicochemical properties for transdermal administration. Compound 26 bound to human AR with an IC50of 0.7 nM with great selectivity over other nuclear hormone receptors and potently activated AR in a C2C12 muscle cell reporter gene assay with an EC50of 0.5 nM. It showed high aqueous solubility of 1.3 g/L at pH 7.4, and an in silico model as well as a customized parallel artificial membrane permeability assay indicated good skin permeation. Indeed, when measuring skin permeation through excised human skin, an excellent flux of 2 μg/(cm2·h) was determined without any permeation enhancers. In a 2 week Hershberger model using castrated rats, the compound showed dose-dependent effects fully restoring skeletal muscle weight at 0.3 mg/kg/day after subcutaneous administration with high selectivity over prostate stimulation.

PYRAZOLINE DERIVATIVES AND THEIR USE AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

The invention relates to a compound of formula (I) in free form or in pharmaceutically acceptable salt form (I), in which the substituents are as defined in the specification; to compounds of formula (I) for use as androgen receptor modulators. The present invention further provides a combination of pharmacologically active agents and a pharmaceutical composition