42346-68-9

Usage

Uses

Used in Pharmaceutical Industry:
1-METHYL-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID is used as an active pharmaceutical ingredient for the treatment of chemotherapy-induced nausea and vomiting. Its application as an ondansetron in-adhesive transdermal patch allows for a non-invasive and convenient method of administration, providing continuous and controlled release of the drug to effectively manage nausea and vomiting associated with cancer treatments.

InChI:InChI=1/C6H9NO3/c1-7-3-4(6(9)10)2-5(7)8/h4H,2-3H2,1H3,(H,9,10)

Upstream product

• 59857-86-2 (±)-methyl 1-methyl-5-oxo-pyrrolidine-3-carboxylate 
• 617-52-7 Dimethyl itakonate 
• 97-65-4 2-methylenesuccinic acid 
• 74-89-5 methylamine 

Downstream Products

• 304858-50-2 1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 1291486-24-2 1-methyl-5-oxo-pyrrolidine-3-carbonyl chloride 
• 304858-62-6 N-(2-hydroxyethyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 304858-68-2 1-methyl-5-oxo-N-(3-oxopropyl)-N-phenylpyrrolidine-3-carboxamide 
• 304858-54-6 N-(3-chloropropyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 679003-57-7 2-{[(1-methyl-5-oxopyrrolidin-3-yl)carbonyl]-anilino}acetic acid 
• 679003-56-6 ethyl 2-{[(1-methyl-5-oxopyrrolidin-3-yl)carbonyl]-anilino}acetate 
• 304858-56-8 N-(4-chlorobutyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 304858-58-0 N-(5-chloropentyl)-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 863024-33-3 N-[2-(1,3-dioxolan-2-yl)ethyl]-1-methyl-5-oxo-N-phenyl-pyrrolidine-3-carboxamide 
• 304859-35-6 N-[3-(4-benzylpiperazin-1-yl)propyl]-1-methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide 
• 780027-26-1 N-[3-(4-benzylpiperidin-1-yl)propyl]-1-methyl-N-(3-methylphenyl)-5-oxopyrrolidine-3-carboxamide 

Relevant academic research and scientific papers

NOVEL COMPOUNDS

Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.

MIXTURES OF ITACONIC ACID OR ITACONIC ACID DERIVATIVES AND PRIMARY AMINES FOR PRODUCING 1,3- AND 1,4-ALKYL METHYL PYRROLIDONES

The present invention relates to a mixture comprising itaconic acid or an itaconic acid derivative and a primary amine of the formula (I) [in-line-formulae]R—NH2??(I)[/in-line-formulae] where the molar ratio of primary amine to itaconic acid or the itaconic acid derivative is in the range from 0.5:1 to 20:1, wherein the mixture comprises 50 mole percent or less of 4-carboxypyrrolidones of the formula (II), derivatives of the 4-carboxypyrrolidones of the formula (II) and 4-carbamidopyrrolidones of the formula (III) based on the itaconic acid used or the itaconic acid derivative used and in which R is a linear or branched saturated aliphatic radical having 1 to 24 carbon atoms or a saturated cycloaliphatic radical having 3 to 24 carbon atoms. The invention further provides for the use of the inventive mixtures for preparing 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones, and also a process for preparing 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones. In addition, the present invention relates to mixtures comprising 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones and 1,3-alkylmethylpyrrolidines, where the proportion of 1,3-alkylmethylpyrrolidines is in the range from 10 to 10 000 ppm, and to mixtures comprising 1,3-alkylmethylpyrrolidone and 1,4-alkylmethylpyrrolidone, wherein the molar ratio of 1,3-alkylmethylpyrrolidone to 1,4-alkylmethylpyrrolidone is in the range from 1:1 to 10:1.

CCR5 antagonists as anti-HIV-1 agents. 1. Synthesis and biological evaluation of 5-oxopyrrolidine-3-carboxamide derivatives

A novel lead compound, N-{3-[4-(4-fluorobenzoyl)piperidin-1-yl]propyl}-1- methyl-5-oxo-N-phenylpyrrolidine-3-carboxamide (1), was identified as a CCR5 antagonist by high-throughput screening using [125I]RANTES and CCR5-expressing CHO cells. The IC50 value of 1 was 1.9 μM. In an effort to improve the binding affinity of 1, a series of 5-oxopyrrolidine-3- carboxamides was synthesized. Introduction of 3,4-dichloro substituents to the central phenyl ring (10i, IC50=0.057 μM; 11b, IC 50=0.050 μM) or replacing the 1-methyl group of the 5-oxopyrrolidine moiety with a 1-benzyl group (12e, IC50=0.038 μM) was found to be effective for improving CCR5 affinity. Compound 10i, 11b, and 12e also inhibited CCR5-using HIV-1 envelope-mediated membrane fusion with IC50 values of 0.44, 0.19, and 0.49 μM, respectively.