455957-94-5

Usage

Uses

Used in Pharmaceutical Industry:
(3S,4R)-1-TERT-BUTYL-4-(2,4-DIFLUOROPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID is used as a potential pharmaceutical candidate for its unique structure and potential biological activity. Its chiral nature and specific stereochemistry may offer advantages in drug development, such as selectivity and potency.
Used in Research Settings:
In research, (3S,4R)-1-TERT-BUTYL-4-(2,4-DIFLUOROPHENYL)PYRROLIDINE-3-CARBOXYLIC ACID can be employed as a chemical probe to study biological processes and interactions. Its unique structure may allow for the investigation of specific molecular targets or pathways, contributing to a better understanding of biological systems.

InChI:InChI=1/C15H19F2NO2/c1-15(2,3)18-7-11(12(8-18)14(19)20)10-5-4-9(16)6-13(10)17/h4-6,11-12H,7-8H2,1-3H3,(H,19,20)/t11-,12+/m0/s1

Upstream product

• 455957-73-0 methyl (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)-pyrrolidine-3-carboxylate 
• 862283-30-5 PF-884918 
• 794500-76-8 (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carbonitrile 
• 794500-77-9 (3R,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carbonitrile 
• 852305-06-7 (4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carbonitrile 

Downstream Products

• 1002728-83-7 (4S)-1-[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-ylcarbonyl]-4-[(4,4-dimethylcyclohexyl)(2,2-dimethylpropanoyl)amino]-N,N-dimethyl-L-prolineamide trifluoroacetate 
• 862281-92-3 (3R,4R,5S)-1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-3,5-dimethyl-4-phenylpiperidin-4-ol 
• 1153741-43-5 C₁₅H₁₈ClF₂NO*ClH 
• 938450-48-7 1-[2-(1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-4,5-dimethylphenyl]propan-1-one 
• 1226770-01-9 N-[(3S,5S)-1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-5-(piperazin-1-ylcarbonyl)pyrrolidin-3-yl]-N-(4,4-dimethylcyclohexyl)acetamide 
• 1221821-89-1 (3R,4R,5S)-1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-4-(4-methoxyphenyl)-3,5-dimethylpiperidin-4-ol hydrochloride 
• 1221821-92-6 3-[(3R,4R,5S)-1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}-4-hydroxy-3,5-dimethylpiperidin-4-yl]benzonitrile hydrochloride 

Relevant academic research and scientific papers

MELANOCORTIN RECEPTOR AGONISTS

The present invention relates to a compound having a good agonistic activity to melanocortin receptor, or pharmaceutically acceptable salt or isomer thereof, and an agonistic composition for melanocortin receptor comprising the same as an active ingredient.

MELANOCORTIN RECEPTOR AGONISTS

The present invention relates to a compound having a good agonistic activity to melanocortin receptor, or pharmaceutically acceptable salt or isomer thereof, and an agonistic composition for melanocortin receptor comprising the same as an active ingredient.

Discovery of a selective small-molecule melanocortin-4 receptor agonist with efficacy in a pilot study of sexual dysfunction in humans

The relevance of the melanocortin system to sexual activity is well established, and nonselective peptide agonists of the melanocortin receptors have shown evidence of efficacy in human sexual dysfunction. The role of the MC4 receptor subtype has received particular scrutiny, but the sufficiency of its selective activation in potentiating sexual response has remained uncertain owing to conflicting data from studies in preclinical species. We describe here the discovery of a novel series of small-molecule MC4 receptor agonists derived from library hit 2. The addition of methyl substituents at C3 and C5 of the 4-phenylpiperidin-4-ol ring was found to be markedly potency-enhancing, enabling the combination of low nanomolar potencies with full rule-of-five compliance. In general, the series shows only micromolar activity at other melanocortin receptors. Our preferred compound 40a provided significant systemic exposure in humans on both sublingual and oral administration and was safe and well tolerated up to the maximum tested dose. In a pilot clinical study of male erectile dysfunction, the highest dose of 40a tested (200 mg) provided a similar level of efficacy to sildenafil.

ACYLATED PIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel N-acylated piperidine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention

ACYLATED PIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel N-acylated piperidine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention

Pharmaceutically active compounds

The present invention relates to a class of melanocortin MCR4 agonists of general formula (I) wherein R1, R2, R3, R4 and R5 are as defined herein and especially to selective MCR4 agonist compounds, to

Enantioselective nitrile anion cyclization to substituted pyrrolidines. A highly efficient synthesis of (3S,4R)-N-tert-butyl-4-arylpyrrolidine-3- carboxylic acid

(Chemical Equation Presented) A practical asymmetric synthesis of N-tert-butyl disubstituted pyrrolidines via a nitrile anion cyclization strategy is described. The five-step chromatography-free synthesis of (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrr

PROCESS AND INTERMEDIATES FOR THE PREPARATION OF PYRROLIDINE CARBOXYLIC ACIDS

A novel process is provided for the preparation of pyrrolidine carboxylic acids, and the useful intermediates obtained therein. These compounds are intermediates for the synthesis of melanocortin-4 receptor (MC-4R), which are useful for the treatment of d

ACYLATED PIPERAZINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel N-acylated piperazine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or prevention

BICYCLIC PIPERIDINE DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel bicyclic N-acylated piperidine derivatives are agonists of the human melanocortin receptor(s) and, in particular, are selective agonists of the human melanocortin-4 receptor (MC-4R). They are therefore useful for the treatment, control, or p