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
• Article Data: 25

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

Description

L-Nateglinide is an impurity found within the commercial pharmaceutical Nateglinide (N379375), which is a novel D-phenylalanine-derivative hypoglycemic agent. It is a white to off-white solid and is commonly associated with antidiabetic medications.

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

• 105746-47-2 N-<(trans-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester 
• 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 
• 21685-51-8 D-phenylalanine methyl ester 
• 175284-00-1 p-menthan-7-oic acid methyl ester 
• 594837-86-2 C₁₉H₂₆NO₃^(1-)*K⁽¹⁺⁾ 
• 594837-85-1 C₁₉H₂₆NO₃^(1-)*Na⁽¹⁺⁾ 
• 958230-60-9 N-<(cis-4-Isopropylcyclohexyl)carbonyl>-D-phenylalanine methyl ester 
• 7084-93-7 (1r,4s)-4-isopropylcyclohexanecarboxylic acid 
• 958230-63-2 N-[(trans-4-Isopropylcyclohexyl)carbonyl]-L-phenylalanine methyl ester 
• 63-91-2 L-phenylalanine 
• 79-22-1 methyl chloroformate 

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.

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.