571170-77-9

Basic information

• Product Name: MK 0524
• Synonyms: Cyclopent[b]indole-3-acetic acid, 4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)-, (3R)-Laropiprant;MK 0524;Laropiprant;MK-0524(Laropiprant)/;Laropiprant(MK0524);(3R)-4-[(4-Chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-5-(methylsulfonyl)cyclopent[b]indole-3-acetic acid;[(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(Methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid;(R)-2-(4-(4-chlorobenzyl)-7-fluoro-5-(Methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• CAS NO: 571170-77-9
• Molecular Formula: C₂₁H₁₉ClFNO₄S
• Molecular Weight: 435.901
• EINECS: 1312995-182-4
• Mol File: 571170-77-9.mol
• Article Data: 11

Chemical Properties

• Melting Point: 175∶C
• Boiling Point: 710.014 °C at 760 mmHg
• Flash Point: 383.203 °C
• Appearance: /
• Density: 1.48
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 4.54±0.10(Predicted)
• CAS DataBase Reference: MK 0524(CAS DataBase Reference)
• NIST Chemistry Reference: MK 0524(571170-77-9)
• EPA Substance Registry System: MK 0524(571170-77-9)

Safety Data

• Hazardous Substances Data: 571170-77-9(Hazardous Substances Data)

Usage

General Description

MK 0524, also known as Rimegepant, is a small molecule drug that functions as a calcitonin gene-related peptide receptor antagonist. It is primarily used for the treatment of acute migraine attacks and is part of a class of drugs known as gepants. By blocking the action of calcitonin gene-related peptide, MK 0524 helps to alleviate migraine symptoms such as headache, nausea, and sensitivity to light and sound. Clinical trials have shown that Rimegepant is effective in reducing the frequency and severity of migraines, and it has been approved for use in several countries around the world. Overall, MK 0524 has demonstrated promising potential as a treatment for migraines and is a focus of ongoing research and development.

Upstream product

• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 
• 828932-45-2 [(3S,3aS,8bS)-5-bromo-7-fluoro-3,3a,4,8b-tetrahydro-cyclopenta[b]indol-3-yl]acetic acid 
• 828932-44-1 (2aS,9bS,9cS)-6-bromo-8-fluoro-2a,3,9b,9c-tetrahydro-4H-benzo[b]cyclopenta[gh]pyrrolizin-4-one 
• 828932-38-3 (S)-2-Cyclopent-2-enyl-malonic acid 
• 800377-03-1 ethyl (3R)-(7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate 
• 371-40-4 4-fluoroaniline 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 393509-04-1 [5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 571170-85-9 (5-bromo-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl)-acetic acid methyl ester 
• 571170-84-8 [2-(2-bromo-4-fluoro-phenylimino)-cyclopentyl]-acetic acid ethyl ester 
• 571170-89-3 [5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester 
• 393509-05-2 [(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 393509-23-4 (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid 

Relevant articles and documents

Discovery of a potent and selective prostaglandin D2 receptor antagonist, [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-(methylsulfonyl)-1,2,3,4- tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (MK-0524)

The discovery of the potent and selective prostaglandin D2 (PGD2) receptor (DP) antagonist [(3R)-4-(4-chlorobenzyl)-7-fluoro-5- (methylsulfonyl)-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]-acetic acid (13) is presented. Initial lead antagonists 6 and 7 were found to be potent and selective DP antagonists (DP Ki = 2.0 nM for each); however, they both suffered from poor pharmacokinetic profiles, short half-lives and high clearance rates in rats. Rat bile duct cannulation studies revealed that high concentrations of parent drug were present in the biliary fluid (Cmax = 1100 μM for 6 and 3900 μM for 7). This pharmacokinetic liability was circumvented by replacing the 7-methylsulfone substituent present in 6 and 7 with a fluorine atom resulting in antagonists with diminished propensity for biliary excretion and with superior pharmacokinetic profiles. Further optimization led to the discovery of the potent and selective DP antagonist 13.

NIACIN RECEPTOR AGONISTS, COMPOSITIONS CONTAINING SUCH COMPOUNDS AND METHODS OF TREATMENT

The present invention encompasses compounds of Formula (I); as well as pharmaceutically acceptable salts and hydrates thereof, that are useful for treating dyslipidemias. Pharmaceutical compositions and methods of use are also included.

METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS

A method of treating atherosclerosis, dyslipidemia and related conditions is disclosed wherein a compound of formula I: or a pharmaceutically acceptable salt or solvate thereof is administered to the patient in combination with a DP receptor antagonist. T