376348-77-5

Usage

Uses

Used in Pharmaceutical Industry:
4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE is used as a weight-loss drug for its ability to influence the brain's appetite control center, thereby reducing food intake and promoting weight loss in obese individuals.
Used in Research and Development:
4,4-DIFLUORO-N-((1S)-3-HYDROXY-1-PHENYLPROPYL)CYCLOHEXANE-1-CARBOXAMIDE is used as a subject of research for its potential therapeutic effects on conditions such as type 2 diabetes and cardiovascular diseases, despite its withdrawal from the market due to safety concerns.

Upstream product

• 122665-97-8 4,4-difluorocyclohexanecarboxylic acid 
• 82769-76-4 (S)-3-amino-3-phenylpropanol 
• 376348-78-6 4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide 
• 376348-76-4 ethyl (S)-3-[(4,4-difluorocyclohexyl)carboxamido]-3-phenylpropanoate 
• 376348-75-3 4,4-difluorocyclohexane-1-carbonyl chloride 
• 340188-50-3 ethyl (S)-3-amino-3-phenyl-propionate hydrochloride 

Downstream Products

• 376348-78-6 4,4-difluorocyclohexanecarboxylic acid (3-oxo-1-phenyl-propyl)-amide 
• 674782-29-7 maraviroc 

Relevant academic research and scientific papers

METHOD FOR PREPARING MARAVIROC

Provided is a method for preparing a tropane derivative, maraviroc, including reacting a compound of formula (II) with a compound of formula (I), wherein the compound of formula (II) is prepared by the steps of acetylation of a compound of formula (III), activation and substitution of a compound of formula (IV) by a chlorination agent, cyclization of a compound of formula (V), and debenzylation of a compound of formula (VI) by hydrogenation. Hence, the present disclosure provides a method for preparing maraviroc with good yield and simple operation.

Asymmetric synthesis of maraviroc (UK-427,857)

The asymmetric synthesis of Maraviroc (UK-427,857), a chemochine receptor 5 (CCR-5) receptor antagonist, based on an expeditious organocatalytic enantioselective assembly of the chiral βamino aldehyde key fragment is presented. The reactions were performed on a gram-scale and allow for the rapid construction of new Maraviroc analogues.

Process research and scale-up of a commercialisable route to maraviroc (UK-427,857), a CCR-5 receptor antagonist

A six-step synthetic route to the CCR-5 receptor antagonist, Maraviroc (UK-427,857) (1) has been developed and demonstrated at scale in a pilot plant. The route has supported four Pilot-Plant campaigns and has produced multikilogram quantities of 1. Continued development of the synthetic route has resulted in a robust process with improved throughput compared to that of the original synthesis (Haycock-Lewandowski, S. J.; Mawby, N. J.; Wilder, A.; Ahman, J. Org. Process Res. Dev. 2008, 12, 1094-1103).

NOVEL PIPERIDINE/8-AZABICYCLO [3.2.1] OCTAN DERIVATIVES AS MODUILATORS OF CHEMOKINE RECEPTOR CCR5

Compounds of formula (I) wherein neither R4 nor R5 is hydrogen; compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating CCR5 receptor activity in a warm blooded animal).