393509-05-2

Basic information

• Product Name: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• Synonyms: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid
• CAS NO: 393509-05-2
• Molecular Weight: 436.708
• Mol File: 393509-05-2.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid(393509-05-2)
• EPA Substance Registry System: (R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid(393509-05-2)

Safety Data

• Hazardous Substances Data: 393509-05-2(Hazardous Substances Data)

Usage

General Description

The chemical compound "(R)-2-(5-broMo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid" is a potential pharmaceutical intermediate or active pharmaceutical ingredient (API). It contains a carboxylic acid functional group, making it suitable for drug development. The compound also contains a cyclopenta[b]indol-3-yl core, which suggests potential activity as an agonist or antagonist at various receptors, such as serotonin receptors. The presence of bromine, chlorine, and fluorine atoms in the molecule may also contribute to its pharmacological properties or metabolic stability. Further research and testing would be necessary to fully understand the potential uses and properties of this compound in the context of drug development.

Upstream product

• 393509-23-4 (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid 
• 104-83-6 1-Chloro-4-(chloromethyl)benzene 
• 393509-04-1 [5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 10420-89-0 (S)-1-(1-Naphthyl)ethylamine 
• 393509-24-5 C₁₂H₁₃N*C₂₀H₁₆BrClFNO₂ 
• 869194-37-6 (3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-ol 
• 869194-32-1 5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one 
• 869194-30-9 5-bromo-7-fluoro-1,4-dihydrocyclopenta[b]indol-3(2H)-one 
• 393509-21-2 ethyl (7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate 
• 371-40-4 4-fluoroaniline 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 
• 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 

Downstream Products

• 571170-77-9 laropiprant 
• 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 
• 936337-07-4 methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 
• 794535-36-7 [5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid 
• 571170-92-8 [4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester 
• 1009099-49-3 ((3S)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)methanol 
• 1009099-50-6 1-((3S)-4-(4-chlorobenzyl)-7-fluoro-3-(hydroxymethyl)-1,2,3,4-tetrahydrocyclo-penta[b]indol-5-yl)ethanone 
• 1026032-05-2 acetic acid 5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1009099-48-2 1-((3S)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)ethane-1,2-diol 
• 1026726-96-4 methanesulfonic acid 5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1026405-15-1 acetic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 
• 1027400-35-6 methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester 

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.

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

The present invention relates to niacin receptor agonists of formula: (I); as well as pharmaceutically acceptable salts and solvates. The compounds are useful for treating dyslipidemias, and in particular, reducing serum LDL, VLDL and triglycerides, and raising HDL levels. Pharmaceutical compositions and methods of treatment are also included.