64471-43-8

Usage

Uses

Used in Pharmaceutical Industry:
(S)-α-cyclopentyl-α-hydroxy-α-phenylacetic acid is used as a chiral building block for the synthesis of pharmaceutical agents. Its unique chemical structure allows for the development of new drugs with potential therapeutic applications.
Used in Drug Discovery and Development:
(S)-α-cyclopentyl-α-hydroxy-α-phenylacetic acid is used as a valuable molecule in drug discovery and development. Its potential biological activity and therapeutic potential make it an important compound for researchers and scientists in the field of medicinal chemistry and pharmaceutical sciences.
Used in the Treatment of Various Diseases and Conditions:
(S)-α-cyclopentyl-α-hydroxy-α-phenylacetic acid has potential therapeutic potential in the treatment of various diseases and conditions. Its unique chemical structure and potential biological activity make it a promising candidate for further research and development in the pharmaceutical industry.

Upstream product

• 302842-81-5 (S)-α-(cyclopentyl-1-ene)-α-hydroxy-α-phenylacetic acic 
• 137-43-9 Cyclopentyl bromide 
• 90581-53-6 (2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one 
• 937179-77-6 cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-cyclopentyl-1,3-dioxolan-4-one 
• 944324-89-4 (+/-)-[(1-cyano-1-cyclopentyl-1-phenylmethoxy)carbonyl]methyl acetate 
• 944325-18-2 (S)-(+)-1-cyano-1-cyclopentyl-1-phenylmethyl hydroxyacetate 
• 944324-84-9 (+/-)-1-cyclopentyl-1-hydroxy-1-phenylacetonitrile 
• 5422-88-8 phenyl cyclopentyl ketone 
• 17199-29-0 (S)-Mandelic acid 
• 427-49-6 2-cyclopentyl-2-hydroxy-2-phenylacetic acid 
• 90581-52-5 cis-(2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one 
• 611-71-2 (R)-Mandelic Acid 
• 302842-80-4 (2S,5R)-2-(tert-butyl)-5-phenyl-5-(1-hydroxycyclopentyl)-1,3-dioxolan-4-one 
• 185030-08-4 cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-(cyclopentyl-1-ene)-1,3-dioxolan-4-one 

Downstream Products

• 183201-50-5 (S)-1-Cyclopentyl-1-phenyl-ethane-1,2-diol 
• 860644-54-8 (S)-methyl-α-cyclopentyl-α-hydroxyl-α-phenylacetate 
• 244277-89-2 (+)-J 104129 
• 184488-62-8 (S)-2-Cyclopentyl-2-phenyl-oxirane 
• 114121-68-5 (S)-2-[(R)-(1-Aza-bicyclo[2.2.2]oct-3-yl)oxy]-1-cyclopentyl-1-phenyl-ethanol 
• 114121-68-5 (S)-2-[(S)-(1-Aza-bicyclo[2.2.2]oct-3-yl)oxy]-1-cyclopentyl-1-phenyl-ethanol 
• 852461-42-8 Toluene-4-sulfonic acid (S)-2-cyclopentyl-2-hydroxy-2-phenyl-ethyl ester 
• 860469-61-0 (S)-N-trichloroethoxyformyl-3-azabicyclo[3,3,1]nonan-9-yl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate 
• 230632-95-8 (S)-N-methyl-3-azabicyclo[3,3,1]nonan-9-yl 2'-cyclopentyl-2'-hydroxy-2'-phenylacetate 

Relevant academic research and scientific papers

Discovery of a Novel Muscarinic Receptor PET Radioligand with Rapid Kinetics in the Monkey Brain

Positron emission tomography (PET), together with a suitable radioligand, is one of the more prominent methods for measuring changes in synaptic neurotransmitter concentrations in vivo. The radioligand of choice for such measurements on the cholinergic sy

PROCESSES FOR MAKING, AND METHODS OF USING, GLYCOPYRRONIUM COMPOUNDS

Provided herein are processes for making and methods of using salts of glycopyrronium, including solid forms and forms suitable for use as topicals. Disclosed here are processes for making salts of glycopyrronium, also processes for making compositions comprising salts of glycopyrronium, and methods of treating hyperhidrosis with salts of glycopyrronium as well as with compositions comprising salts of glycopyrronium such as, but not limited to, topical compositions. Disclosed herein are methods of treating hyperhidrosis including administering salts of glycopyrronium to subjects in need thereof.

Stereoisomers of N-substituted soft anticholinergics and their zwitterionic metabolite based on glycopyrrolate - Syntheses and pharmacological evaluations

Purpose. In this study, isomers of two N-substituted soft anticholinergics based on glycopyrrolate, SGM (PcPOAGP_NA.Me) and SGE (PcPOAGP_NA.Et) [3′-(2-cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1′-methyl-1′- alkoxycarbonylpyrrolidinium bromide] and their zwitterionic metabolite, SGa (PcPOAGP_NA.H) [3′-(2-cyclopentyl-2-phenyl-2-hydroxyacetoxy)-1′- methyl-1′-carboxymethylpyrrolidinium inner salt] were synthesized and their pharmacological activities were evaluated in vitro and in vivo. Methods. The isomers of SGM and SGE were synthesized with both optically pure methyl-cyclopentylmandelate and 3-hydroxy-N-methylpyrrolidine. Trans-esterification followed by quarternization with alkyl bromoacetate gave four isomers of SGM or SGE with the nitrogen chiral center unresolved (2R3′S-SGM, 2R3′R-SGM, 2S3′S-SGM, 2S3′R-SGM or 2R3′S-SGE, 2R3′R-SGE, 2S3′S-SGE, 2S3′R-SGE). The hydrolysis of these four isomers followed by HPLC separation resulted in eight fully resolved isomers of SGa (2R3′R1′R, 2R3′S1′R, 2R3′R1′S, 2R3′S1′S, 2S3′R1′R, 2S3′S1′R, 2S3′R1′S, and 2S3′S1′S). Pharmacological activities were assessed by using in vitro receptor-binding assay and guinea pig ileum pA2-assay, and by evaluating the in vivo rabbit mydriatic effects. Results were compared to those obtained with conventional anticholinergic agents, such as glycopyrrolate, N-meythylscopolamine, and tropicamide, as well as those obtained with previously prepared racemic mixtures and 2R isomers. Results. Receptor binding pK i values at cloned human muscarinic receptors (M1-M 4 subtypes) were in the 6.0-9.5 range for the newly synthesized SGM and SGE isomers, and in the 5.0-8.6 range for the SGa isomers. In all cases, 2R isomers were significantly more active than 2S isomers (27 to 447 times for SGM isomers, and 6 to 4467 times for SGa isomers). Among the four SGM isomers with unresolved 1′ (N) chiral center, the 3′R isomers were more active than the corresponding 3′S isomers (1.5-12.9 times), whereas, among the SGa isomers, the 3′S isomers were not always more active than the corresponding 3′R isomers indicating that activity determined based on configuration at chiral center 3′ is significantly affected by the configuration of the other two chiral centers, 2 and 1′. Among the completely resolved eight SGa isomers (all three chiral centers resolved), 1′S isomers were always more active than the corresponding 1′R isomers (1.8-22.4 times). Results also indicate that some isomers showed good M3/M2 muscarinic-receptor subtype-selectivity (about 3-5 times), and 2R and 3′S were the determining configurations for this property. Guinea pig ileum assays and rabbit mydriasis tests on SGa isomers further confirmed the stereospecificity. In rabbit eyes, some 2R-SGa isomers showed mydriatic potencies similar to glycopyrrolate and exceeded tropicamide, but their mydriatic effects lasted considerably shorter, and they did not induce dilation of the pupil in the contralateral, water-treated eye. These results indicate that these compounds are locally active, but safe and have a low potential to cause systemic side effects. The pharmacological potency of the eight SGa isomers was estimated as 2R3′S1′S ≈ 2R3′R1′S ≈ 2R3′S1′R > 2R3′R1′R > 2S3′R1′S > 2S3′S1′S ≈ 2S3′R1′R > 2S3′S1′R (p 3/M2 muscarinic-receptor subtype-selectivity of soft anticholinergics, SGM, SGE, and SGa have been demonstrated. In agreement with previous results, the potential for their effective and safe use has been confirmed.

Enzymatic resolution of hindered cyanohydrins, key precursors of muscarinic receptor antagonists

Enantiomerically pure 1-cycloalkyl-1-hydroxy-1-phenylcyanohydrins, key precursors in the synthesis of (S)-oxybutynin and other antimuscarinic agents, have been successfully prepared via lipase-catalyzed kinetic resolutions. Pseudomonas cepacia and Candida antarctica lipase B have shown excellent enantioselectivities in hydrolysis and acylation processes, depending on the substrate structure and the reaction conditions. Furthermore, molecular modeling of phosphonate transition state analogue for the C. antarctica lipase B enzymatic hydrolysis resolution step supports these facts, which were experimentally observed.

SOFT ANTICHOLINERGIC ESTERS

Soft anticholinergic esters of the formulas: wherein R1 and R2 are both phenyl or one of R1 and R2 is phenyl and the other is cyclopentyl; R is C1-C8 alkyl, straight or branched chain; and X- is an anion with a single negative charge; and wherein each asterisk marks a chiral center; said compound having the R, S or RS stereoisomeric configuration at each chiral center unless specified otherwise, or being a mixture thereof.

Stereoselective synthesis of the optical isomers of a new muscarinic receptor antagonist, HL-031120

We present here a practical stereoselective synthetic method to produce enantiopure isomers of a new muscarinic receptor antagonist, HL-031120 (3-quinuclidinyl-2′-cyclopentyl-2′-hydroxy-2′-phenylacetate, I). Four optical isomers were effectively by stereoselective synthesized using pivaldehyde as steric hindrance agent from the chiral starting material, ( S ) or ( R )-mandelic acid. The isomers were obtained with 70-76% yields in 98-99% e.e. Copyright Taylor & Francis Group, LLC.

Optical resolution, stereoselective synthesis, and crystal structure of 9α-(3-azabicyclo[3,3,1]nonanyl)-2′cyclopentyl-2′-hydroxy- 2′-phenylacetate

9α-(3-Azabicyclo[3,3,1 ]nonanyl)-2′-cyclopentyl-2′- hydroxy-2′-phenylacetate (1) was synthesized and its enantiomers were obtained by the optical resolution of racemates with the chiral host N-p-toluenesulfonylglutamic acid. Optical pure 1 was also effect

Stereoselective synthesis of α-alkyl-α-hydroxylphenylacetic acid. Part (I): Asymmetric alkylation of (S)-mandelic acid

An effective asymmetric synthesis of α-alkyl-α-hydroxyl phenyl acetic acid using benzaldehyde as steric hindrance agent has been accomplished by utilising the readily available and inexpensive chiral starting material, (S)-mandelic acid. The ee was determined by 1H NMR with Eu(hfc) 3 as shift reagent.

3,6-DISUBSTITUTED AZABICYCLO [3.1.0]HEXANE DERIVATIVES USEFUL AS MUSCARINIC RECEPTOR ANTAGONISTS

This invention generally relates to the derivatives of 3,6 disubstituted azabicyclo[3.1.0]hexanes. The compounds of this invention are muscarinic receptor antagonists which are useful, inter-alia, for the treatment of various diseases of the respiratory, urinary and gastrointestinal systems mediated through muscarinic receptors. The invention also relates to a process for the preparation of compounds of the present invention, pharmaceutical compositions containing the compounds of the present invention and the methods for treating the diseases mediated through muscarinic receptors.