342639-02-5

Basic information

• Product Name: Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-diMethyl-1-piperidinyl]Methyl]-1-oxo-3-phenylpropyl]-, rel- (9CI)
• Synonyms: Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-diMethyl-1-piperidinyl]Methyl]-1-oxo-3-phenylpropyl]-, rel- (9CI);2-(2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetic acid
• CAS NO: 342639-02-5
• Molecular Formula: C25H32N2O4
• Molecular Weight: 424.53258
• Mol File: 342639-02-5.mol

Chemical Properties

• Boiling Point: 684.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.166±0.06 g/cm3(Predicted)
• PKA: 3.39±0.10(Predicted)
• CAS DataBase Reference: Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-diMethyl-1-piperidinyl]Methyl]-1-oxo-3-phenylpropyl]-, rel- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-diMethyl-1-piperidinyl]Methyl]-1-oxo-3-phenylpropyl]-, rel- (9CI)(342639-02-5)
• EPA Substance Registry System: Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-diMethyl-1-piperidinyl]Methyl]-1-oxo-3-phenylpropyl]-, rel- (9CI)(342639-02-5)

Safety Data

• Hazardous Substances Data: 342639-02-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-, rel(9CI) is used as a potential pharmaceutical compound for its unique structure and properties that may contribute to the development of new drugs or therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, Glycine, N-[2-[[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]-, rel(9CI) may serve as a valuable tool for studying the interactions between biological molecules and the compound's specific structural features, potentially leading to insights into new biochemical pathways or mechanisms.

Upstream product

• 1314751-88-6 ethyl 2-((S)-2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetate hydrochloride 
• 145603-86-7 (+)-<<2'(S)-<<4(R)-3-(hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl>methyl>-1-oxo-3-phenylpropyl>amino>acetic acid 2-methylpropyl ester 
• 145590-44-9 alvimopan 
• 149541-62-8 cis-(-)-carbonic acid ethyl 1,3-dimethyl-4-[3-(l-methylethoxy)phenyl]-4-piperidinyl ester 
• 145340-44-9 1,3-dimethyl-4-[3-(propan-2-yloxy)phenyl]-4-piperidinol 
• 4629-80-5 1,3-dimethyl-4-piperidinone 
• 145678-87-1 (-)-3(S),4(S)-dimethyl-4-(3-hydroxyphenyl)piperidine 
• 131738-73-3 3-(isopropyloxy)phenylbromide 
• 223424-24-6 (3S,4S)-4-(3-Isopropoxy-phenyl)-1,3,4-trimethyl-piperidine 
• 444904-02-3 (S)-1,2,3,6-tetrahydro-1,3-dimethyl-4-[3-(1-methylethoxy)phenyl]pyridine 
• 149541-62-8 C₁₉H₂₉NO₄ 
• 149541-62-8 C₁₉H₂₉NO₄ 

Relevant articles and documents

Stereoselective HPLC separation of alvimopan on cellulose-based immobilized polysaccharide as a chiral stationary phase

Chiral separation by normal phase high performance liquid chromatography is one of the most powerful technique to quantify the chiral purity of the compounds. In this study, a novel, simple, and specific analytical method was proposed to ascertain the chi

Synthesis and characterization of all possible diastereoisomers of alvimopan

Isolation of all possible diastereomers of alvimopan 1 was found to be challenging. In order to perform cut off studies during analytical method development, it was mandatory to synthesize and characterize all the diastereomeric impurities. Here in, our efforts toward the synthesis and isolation of alvimopan (1) diastereomers are discussed.

IMPROVED PROCESS FOR THE PREPARATION OF [[2(S)-[[4(R)-(3-HYDROXYPHENYL)-3(R),4-DIMETHYL-1-PIPERIDINYL]METHYL]-1-OXO-3-PHENYLPROPYL]AMINO]ACETIC ACID DIHYDRATE

The present invention relates to an improved process for the preparation of [[2(S)-[[4(R)-(3-hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]amino]acetic acid dihydrate, represented by the following structural formula (I).

A Love [...] synthetic method

The invention relates to a synthesis method of alvimopan. The method comprises the steps of taking the compound A of an acetyl protection piperidine fragment as a raw material and reacting with (S)-ethyl-2-(2-benzyl-3-methyl sulfonoxy alanyl)-acetic acid, then performing one-step basic hydrolysis to prepare the alvimopan. In the technical solution, the synthesis method has the advantages of mild production conditions, simple production process, less side reactions, high product yield, high purity and the like, and is suitable for industrialized large-scale production.

AN IMPROVED PROCESS FOR THE PREPARATION OF [[2(S)-[[4(R)-(3-HYDROXY PHENYL)-3(R), 4-DIMETHYL-1 -PIPERIDINYL]METHYL]-1 -OXO-3-PHENYLPROPYL] AMINO]ACETIC ACID DIHYDRATE

The present invention relates to an improved process for the preparation of [[2(S)-[[4(R)- (3 -hydroxypheny l)-3 (R),4-dimethyl- 1 -piperidinyl] methyl] - 1 -oxo- 3 -phenylpropyl] amino] acetic acid dihydrate, represented by the following structural formula:

Alvimopan preparation method

The invention provides a double salt of methyl phenylpropionyl glycine organic base (L+) which has an (S) configuration and is substituted by a leaving group (X), and a method for preparing alvimopan by using the double salt as an intermediate.

Method for preparing Alvimopan intermediate

The invention discloses a method for preparing an Alvimopan intermediate shown as a formula VI. The method comprises the following steps: under temperature condition of 30-160 DEG C, in an organic solvent, a compound shown as a formula III is subjected to a racemization reaction shown as follows; wherein R is hydrogen OR C1-6 alkyl. The invention also discloses a method for preparing the compound shown as the formula III, which comprises the followings steps: in the solvent, under condition that a pH value is 7-14, a compound shown as a formula II is subjected to a neutralization reaction shown as follows; wherein, Z is chlorine, bromine, acid radical of succinic acid or acid radical of (+)-dibenzoyltartaric acid. The preparation method has the advantages of simple operation, mild reaction condition, little three wastes, environmental protection, high raw material utilization rate, and high yield, and is benefit for industrial production.

PROCESS FOR THE PREPARATION OF ALVIMOPAN OR ITS PHARMACEUTICALLY ACCEPTABLE SALT OR SOLVATE THEREOF

The present invention relates to novel intermediates, ethyl N-[(2S)-2 -benzyl-3- hydroxypropanoyl]glycinate and ethyl N-[(2S)-2-benzyl-3-{[(4-bromophenyl)sulfonyl] oxy}propanoyl]glycinate, and processes for their preparation. The present invention also relates to a process for producing alvimopan or its pharmaceutically acceptable salt or solvate thereof using these novel intermediates.(A).

Solid dispersions of opioid antagonists

Solid dispersions of stable, amorphous opioid antagonists, particularly [[2(S)-[[4(R)-(3-hydroxyphenyl)-3(R),4-dimethyl-piperidinyl]methyl]-1-oxo-3-phenylpropyl]amino]acetic acid, with improved water solubility and bioavailability are disclosed. Also disclosed are methods of preventing or treating a side effect associated with an opioid. In addition, methods of treating or preventing pain, ileus, and opioid bowel dysfunction are disclosed.

Compositions containing opioid antagonists

Compositions containing opioid antagonists are disclosed, particularly alvimopan and its active metabolite in solid dosage forms, where the drug is uniformly distributed, achieves the desired bioavailability, and is stable. Methods of preparing and using the compositions containing opioid antagonists are also disclosed. The results are achieved by a combination of processing techniques and component selection.