105816-05-5

Basic information

• Product Name: L-Nateglinide
• Synonyms: L-Nateglinide;L-Phenylalanine, N-[[4-(1-methylethyl)cyclohexyl]carbonyl]-, trans-;L-Phenylalanine, N-[[trans-4-(1-methylethyl)cyclohexyl]carbonyl]- (9CI);ent-Nateglinide;N-(trans-4-isopropylcyclohexanecarbonyl)-L-phenylalanine;Nateglinide Related CoMpound B;Nateglinide Related Compound B (10 mg) (N-(trans-4-isopropylcyclohexanecarbonyl)-L-phenylalanine);N-[[trans-4-(1-Methylethyl)cyclohexyl]carbonyl]-L-phenylalanine
• CAS NO: 105816-05-5
• Molecular Formula: C19H27NO3
• Molecular Weight: 317.42
• Product Categories: Amino Acids & Derivatives;Metabolites & Impurities
• Mol File: 105816-05-5.mol

Chemical Properties

• Melting Point: 103-111°C
• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: L-Nateglinide(CAS DataBase Reference)
• NIST Chemistry Reference: L-Nateglinide(105816-05-5)
• EPA Substance Registry System: L-Nateglinide(105816-05-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• Hazardous Substances Data: 105816-05-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
L-Nateglinide is used as an impurity in the development and production of Nateglinide (N379375), a hypoglycemic agent. Its presence is significant for ensuring the quality and safety of the final pharmaceutical product, as it can impact the efficacy and potential side effects of the medication.
Used in Antidiabetic Applications:
L-Nateglinide is used as a component in the commercial pharmaceutical Nateglinide, which serves as an antidiabetic agent. It helps in managing blood sugar levels in patients with diabetes, contributing to the overall effectiveness of the treatment.
Used in Quality Control and Research:
L-Nateglinide is used as a reference compound in the quality control and research of Nateglinide and other related hypoglycemic agents. Its analysis and characterization are essential for understanding the properties and behavior of the active pharmaceutical ingredient and ensuring the development of safe and effective medications.

Upstream product

• 7077-05-6 trans-4-isopropylcyclohexane-1-carboxylic acid 
• 673-06-3 D-(R)-phenylalanine 
• 541-41-3 chloroformic acid ethyl ester 
• 84855-54-9 trans-4-iso-propylcyclohexylcarbonyl chloride 
• 175284-00-1 p-menthan-7-oic acid methyl ester 
• 594837-86-2 C₁₉H₂₆NO₃^(1-)*K⁽¹⁺⁾ 
• 594837-85-1 C₁₉H₂₆NO₃^(1-)*Na⁽¹⁺⁾ 
• 100597-38-4 4-iso-propylcyclohexanecarbonyl chloride 
• 1245809-48-6 C₁₇H₂₄O₄S 
• 536-66-3 p-isopropylbenzoic acid 
• 13828-35-8 Methyl cis-4-isopropylcyclohexanecarboxylate 
• 7084-93-7 (1r,4s)-4-isopropylcyclohexanecarboxylic acid 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 100803-81-4 D-phenylalanine sodium salt 

Relevant articles and documents

METHODS FOR TREATING CHRONIC FATIGUE SYNDROME AND MYALGIC ENCEPHALOMYELITIS

In one aspect the invention relates to a method of treatment selected from the group consisting of: (a) treating a symptom such as pain in a subject identified or diagnosed as having Myalgic Encephalomyelitis/Chronic Fatigue Syndrome (ME/CFS); (b) treating a symptom such as pain in a subject having dysfunctional TRPM3 ion channel activity; (c) restoring NK cell function in a subject having dysfunctional TRPM3 ion channel activity; and (d) restoring calcium homeostasis in a subject having dysfunctional TRPM3 ion channel activity. The method comprises the step of administering to the subject a therapeutically effective amount of at least one therapeutic compound selected from the group consisting of: (i) an opioid receptor antagonist; (ii) an opioid antagonist; and (iii) a therapeutic compound that restores TRPM3 ion channel activity. In some embodiments the therapeutic compound is naltrexone hydrochloride.

A high-purity process for the preparation of nateglinide

A preparation method of high-purity nateglinide comprises the following steps: trans-4-isopropyl-cyclohexanecarboxylic acid is taken as a starting material, acyl chloride obtained by chlorinating sulfoxide chloride reacts with D-phenylalanine, the reaction product is subjected to acid hydrolysis to obtain B-type nateglinide, and then the B-type nateglinide is transformed in ethyl alcohol to obtain H-type nateglinide. The method is simple to operate, the raw materials are easy to obtain, the yield is higher and the product quality is high.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF DIABETES

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of fo

Synthesis and biological investigations of nitric oxide releasing nateglinide and meglitinide type II antidiabetic prodrugs: In-vivo antihyperglycemic activities and blood pressure lowering studies

A new group of hybrid nitric oxide-releasing type II antidiabetic drugs possessing a 1-(pyrrolidin-1-yl)diazen-1-ium-1,2-diolate (13 and 18), 1-(N,N-diethylamino)diazen-1-ium-1,2-diolate (14 and 19), or nitrooxyethyl (15 and 20) moiety attached to the car

A PROCESS FOR THE PREPARATION OF NATEGLINIDE

The present invention relates to a process for the preparation of substantially pure nateglinide of formula (I), substantially free from the cis-isomer and L-enantiomer and preparation of enantiomerically pure nateglinide form B, directly from the hydrolysis of a (-)-N-(trans-4-isopropylcyclohexyl-1-carbonyl)-D-phenylalanine alkyl ester in a ketonic solvent or water or mixture thereof.

A PROCESS FOR THE PREPARATION OF N-[[TRANS-4-(1-METHYLETHYL)CYCLOHEXYL]CARBONYL]-D-PHENYLALANINE

The present invention is directed to an novel, industrially viable and cost effective process for preparation of substantially pure N-[[trans-4-(l-methylethyl) cyclohexyl] carbonyl]-D- phenylalanine commonly known as Nateglinide.

PROCESS FOR PRODUCTION OF CARBOXYLIC ACID CHLORIDE COMPOUND

The present invention discloses methods for producing a carboxylic acid chloride compound which comprises the step of reacting an alkyl-substituted cyclohexyl carboxylic acid with a chlorinating agent in the presence of a specific urea compound. According to this invention, it is possible to produce a carboxylic acid chloride compound which has high reaction speed, and whose product has high purity or high yield. Thus produced carboxylic acid chloride compound is useful as an intermediate for producing D-phenylalanine derivatives which are used as agents for treating diabetes.

PROCESS FOR SYNTHESIZING HIGHLY PURE NATEGLINIDE POLYMORPHS

The present invention relates to an improved process for synthesizing highly pure nateglinide of formula-(I). More particularly, the present invention relates to the process for synthesizing highly enantiomerically pure nateglinide form B and form H direc

A NOVEL AND IMPROVED PROCESS FRO THE PREPARATION OF NATEGLINIDE AND ITS POLYMORPH FORM-H

Nateglinide is prepared by an improved process comprising reaction of trans-4-isopropyl cyclohexane carbonyl chloride with N,O-bis- trimethylsilyl protected D-phenyl alanine to give after aqueous workup, crude nateglinide which is converted to Nateglinide form- H using a mixture of cyclohexane / ethyl acetate. trans-4-isopropyl cyclohexane carbonyl chloride is prepared from trans-4- isopropyl cyclohexane carboxylic acid using oxalyl chloride.

PROCESS FOR PREPARING NATEGLINIDE B-TYPE CRYSTALS

An improved process for preparing (-)-N-[(trans-4-isopropylcyclohexane)carbonyl]-D-phenylalanine of Formula I.