757247-75-9

Upstream product

• 573768-09-9 4-amino-2-chloro-3-methyl-benzonitrile 
• 627531-48-0 N-(3-chloro-4-cyano-2-methylphenyl)acetamide 
• 7463-35-6 N-(3-chloro-2-methylphenyl)acetamide 
• 125328-80-5 N-(4-bromo-3-chloro-2-methylphenyl)acetamide 
• 87-60-5 3-chloro-2-methylbenzenamine 

Downstream Products

• 864661-63-2 C₂₂H₁₉ClN₂O₃ 
• 945469-30-7 C₂₆H₄₂ClN₃O₃Si 
• 757247-76-0 (2R,3S)-1-tert-Butyloxycarbonyl-3-(tert-Butyldimethylsilanyloxy)-2-[(1S)-1-(3-chloro-4-cyano-2-methyl-phenylamino)-ethyl]pyrrolidine 
• 864361-79-5 diethyl 2-(3-chloro-4-cyano-2-methylphenyl)malonate 
• 864661-74-5 methyl 3-chloro-4-cyano-2-methylbenzoate 
• 864661-62-1 1-(3-Chloro-4-cyano-2-methylphenyl)-2-oxo-octahydrocyclopenta[b]-pyrrol-4-yl benzoate 
• 864661-61-0 2-(3-chloro-4-cyano-2-methylphenyl)-1-oxo-octahydrocyclopenta[c]-pyrrol-4-yl benzoate 
• 1114546-42-7 2-chloro-4-(5-ethyl-3,3-dimethyl-2,4-dioxopyrrolidin-1-yl)-3-methylbenzonitrile 
• 1114546-06-3 2-chloro-4-[(2S,3S)-3-hydroxy-2,3-dimethyl-5-oxopyrrolidin-1-yl]-3-methylbenzonitrile 
• 1421375-86-1 4-((E)-((2S,4R)-4-(tert-butyldimethylsilyloxy)-2-formylpyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile 
• 1421375-95-2 4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile 
• 1421375-97-4 4-((3S,3aR,4S)-4-(tert-butyldimethylsilyloxy)-3-isopropoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-2-chloro-3-methylbenzonitrile 
• 1421375-30-5 2-chloro-4-((3S,3aS,4S)-4-hydroxy-3-ethoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile 
• 1421375-32-7 2-chloro-4-((3S,3aS,4S)-4-hydroxy-3-isopropoxy-3a,4,5,6-tetrahydro-3H-pyrrolo[1,2-b]pyrazol-2-yl)-3-methylbenzonitrile 

Relevant academic research and scientific papers

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.

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

Discovery of potent and muscle selective androgen receptor modulators through scaffold modifications

A novel series of imidazolin-2-ones were designed and synthesized as highly potent, orally active and muscle selective androgen receptor modulators (SARMs), with most of the compounds exhibiting low nM in vitro potency in androgen receptor (AR) binding and functional assays. Once daily oral treatment with the lead compound 11a (AR Ki = 0.9 nM, EC50 = 1.8 nM) for 14 days induced muscle growth with an ED50 of 0.09 mg/kg, providing approximately 50-fold selectivity over prostate growth in an orchidectomized rat model. Pharmacokinetic studies in rats demonstrated that the lead compound 11a had oral bioavailability of 65% and a plasma half-life of 5.5 h. On the basis of their preclinical profiles, the SARMs in this series are expected to provide beneficial anabolic effects on muscle with minimal androgenic effects on prostate tissue.

Synthesis and SAR of tetrahydropyrrolo[1,2-b][1,2,5]thiadiazol-2(3H)-one 1,1-dioxide analogues as highly potent selective androgen receptor modulators

Replacement of the 3-oxo group of 2-chloro-4-[(7R,7aS)-7-hydroxy-1,3-dioxotetrahydro-1H-pyrrolo[1,2c]imidazol-2(3H)-yl]-3-methylbenzonitrile resulted in a sulfamide series of selective androgen receptor modulator (SARM) agonists.

Novel bicyclic compounds as modulators of androgen receptor function and method

The present invention relates to bicyclic compounds according to formula I, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example sarcopenia, wherein R1, R2, R5, X and n are defined herein.

BICYCLIC MODULATORS OF ANDROGEN RECEPTOR FUNCTION

The present invention relates to bicyclic compounds according to formula I, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example sarcopenia, wherein R1, R2, R5, X, Y and n are defined herein.

Sulfonylpyrrolidine modulators of androgen receptor function and method

Compounds are provided which are useful in the treatment of androgen receptor-associated conditions, such as age-related diseases, which compounds have the structure wherein R1 is hydrogen (H), alkyl or substituted alkyl, alkenyl or substituted alkenyl, arylalkyl or substituted arylalkyl, CO2R4a, CONR4aR4b, and CH2OR4a; R2 is hydrogen (H), OR3, SR3, halo, NHR3, NHCOR4c1, NHCO2R4c1, NHCONR4cR4d and NHSO2R4c; R3 in each functional group is hydrogen (H), alkyl or substituted alkyl, CHF2, CF3 and CON4e; R4, R4a, R4b, R4c, R4c1, R4d, R4e, R4f, R4g, or R4h in each functional group are the same or different and are hydrogen(H), alkyl or substituted alkyl, alkenyl or substituted alkenyl, alkynyl or substituted alkynyl, cycloalkyl or substituted cycloalkyl, arylalkyl or substituted arylalkyl, aryl or substituted aryl, or heteroaryl or substituted heteroaryl; R5 and R5′ are the same or different and are hydrogen(H), alkyl or substituted alkyl, alkenyl or substituted alkenyl, alkynyl or substituted alkynyl, cycloalkyl or substituted cycloalkyl, arylalkyl or substituted arylalkyl, aryl or substituted aryl, or heteroaryl or substituted heteroaryl, wherein at least one of R5 and R5′ is hydrogen, or R5 and R5′ taken together form a double bond with oxygen (O), sulfur (S), NR7 or CR7R7′; where R7 and R7′ are as defined herein; G is an aryl, heterocyclo or heteroaryl group, wherein said group is mono- or polycyclic, and which is optionally substituted; and n is an integer of 1 or 2, m is an integer of 1 or 2, Z is oxygen (—O—) or NR4h, a prodrug ester, all stereoisomers thereof and a pharmaceutically acceptable salt. A method for treating androgen receptor-associated conditions such as age-related diseases is also provided.

Novel bicyclic compounds as modulators of androgen receptor function and method

The present invention relates to bicyclic compounds according to formula I, pharmaceutical compositions containing such compounds and methods of using such compounds in the treatment of androgen receptor-associated conditions, such as age-related diseases, for example sarcopenia, wherein R1, R2, R2′ R5, G, n and W are defined herein.