64471-45-0

Usage

Uses

Used in Chiral Ligand Exchange High-Speed Countercurrent Chromatography:
(2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid is utilized as a chiral ligand in high-speed countercurrent chromatography for the enantioseparation of aromatic α-hydroxyl acids. Its unique stereochemistry allows for selective interactions with other chiral molecules, enabling the efficient separation of enantiomers.
Used in Enantioseparation of Aromatic α-Hydroxyl Acids:
(2R)-2-cyclopentyl-2-hydroxy-2-phenylacetic acid serves as a key component in the enantioseparation process of aromatic α-hydroxyl acids. Its R-configuration plays a vital role in distinguishing between enantiomers, facilitating the separation and purification of these compounds for various applications, such as pharmaceutical development and chemical synthesis.

Upstream product

• 137-43-9 Cyclopentyl bromide 
• 90581-53-6 (2S,5S)-2,5-diphenyl-1,3-dioxolan-4-one 
• 244277-90-5 (2R,5R)-2-(tert-butyl)-5-phenyl-5-cyclopentyl-1,3-dioxolan-4-one 
• 944324-89-4 (+/-)-[(1-cyano-1-cyclopentyl-1-phenylmethoxy)carbonyl]methyl acetate 
• 944324-84-9 (+/-)-1-cyclopentyl-1-hydroxy-1-phenylacetonitrile 
• 611-71-2 (R)-Mandelic Acid 
• 17199-29-0 (S)-Mandelic acid 
• 530-62-1 1,1'-carbonyldiimidazole 
• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 930-30-3 cyclopent-2-enone 
• 81036-97-7 (2S,5S)-2-tert-butyl-5-phenyl-1,3-dioxolan-4-one 
• 894795-19-8 (5R)-2-(tert-butyl)-5-phenyl-1,3-dioxolan-4-one 
• 185030-09-5 (R)-α-(cyclopentyl-1-ene)-α-hydroxyl-α-phenylacetic acid 
• 937179-77-6 cis-(2S,5S)-2-(tert-butyl)-5-phenyl-5-cyclopentyl-1,3-dioxolan-4-one 

Downstream Products

• 244277-89-2 J 104129 
• 183201-49-2 (R)-α-phenyl-α-cyclopentyl-α-hydroxyethanol 
• 64471-47-2 (R)-α-phenyl-α-cyclopentyl-α-hydroxyacetate methyl ester 
• 873912-87-9 N-methyl-3-pyrrolidinyl (-)-cyclopentylmandelate 
• 616866-21-8 (2R,3'R)-3'-(2-cyclopentyl-2-hydroxy-2-phenylacetoxy)-1'-methylpyrrolidine 
• 910099-87-5 (R)-α-phenyl-α-cyclopentyl-α-hydroxyethyl p-toluenesulfonate 
• 114121-68-5 (R)-2-[(S)-(1-Aza-bicyclo[2.2.2]oct-3-yl)oxy]-1-cyclopentyl-1-phenyl-ethanol 
• 114121-68-5 (R)-(-)-3-[(R)-2-hydroxy-2-cyclopentyl-2-phenylethoxy]-1-azabicyclo[2.2.2]octane 
• 852461-44-0 (R)-1-phenyl-1-cyclopentylethylene oxide 
• 719278-73-6 (3S)-1-benzylpyrrolidin-3-yl-(2R)-cyclopentyl(hydroxy)phenyl acetate 
• 236405-46-2 4-Amino-1-((2R)-2-cyclopentyl-2-hydroxy-2-phenylacetyl)piperidine monohydrochloride 
• 207856-85-7 (3S)-1-methylpyrrolidin-3-yl (2R)-2-cyclopentyl-2-hydroxy-2-phenylacetate 
• 1073444-46-8 (R)-2-cyclopentyl-1-(4-dimethylamino-piperidin-1-yl)-2-hydroxy-2-phenylethanone 
• 1128092-42-1 (R)-3-((R)-2-Cyclopentyl-2-hydroxy-2-phenylacetoxy)pyrrolidine-1-carboxylic acid t-butyl ester 

Relevant academic research and scientific papers

[sohupironiumu[sohupironiumu] bromide crystal morphology and manufacturing method thereof

A cocrystal containing the 1'R-diastereomer and the 1'S-diastereomer of sofpironium bromide at a ratio of 1:3 (Form CO), a crystal mixture (for example, Form B) containing Form CO and a crystalline form of the 1'R-diastereomer (Form MN), and a method for

CLASS OF BIFUNCTIONAL COMPOUNDS WITH QUATERNARY AMMONIUM SALT STRUCTURE

The invention provides a class of compounds represented by formula (I), having bifunctional active quaternary ammonium salt structure of a β2-adrenoreceptor agonist and an M receptor antagonist, a pharmaceutically acceptable salt, solvate, and optical isomer thereof. A pharmaceutical composition comprising such a compound with quaternary ammonium salt structure, a method for preparing such a compound with quaternary ammonium salt structure and an intermediate thereof, and uses thereof in treating pulmonary disorders are also provided. The compounds of the invention have high selectivity to the M receptor subtype, and have less adverse reaction and lower toxic and side effects in the treatment of pulmonary diseases such as COPD and asthma.

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.

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

A quaternary ammonium salt of pentethyl quinamidine optical isomer, pharmaceutical composition and its medical use

The invention relates to a quaternary ammonium salt compound shown as a formula I, or pharmaceutically acceptable salt or solvate thereof. The invention also relates to application of the compound as a selective M receptor antagonist, particularly a selec

Guanidine-containing compounds useful as muscarinic receptor antagonists

The invention provides compounds of formula I: or a pharmaceutically acceptable salt thereof, wherein R1-3, R5-7, a, X, Y, Y′, Y″, and Z are as defined in the specification. These compounds are muscarinic receptor antagonists. The in

AMIDINE-CONTAINING COMPOUNDS USEFUL AS MUSCARINIC RECEPTOR ANTAGONISTS

The invention relates to compounds of formula I: or a pharmaceutically acceptable salt thereof, where R1-3, R5, R7, a, b, Q, X, X′, X″, Y, Z, and Ar are as defined in the specification. These compounds are muscarinic recep

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.

Quaternary ammonium compounds useful as muscarinic receptor antagonists

The invention provides compounds of the formula: in salt or zwitterionic form or a pharmaceutically acceptable salt thereof, wherein R1-6, a, Z and Q are as defined in the specification. These compounds are muscarinic receptor antagonists. The

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.