393509-22-3

Usage

Chemical class

Acetic acid derivatives

Molecular structure

Contains a fluorine atom and a cyclopenta[b]indol structure

Biological and pharmacological activities

Has potential activities, but specific functions and applications are still being studied

Research and development

Used in the research and development of pharmaceuticals

Unique structure

Suggests potential in drug discovery and medicinal chemistry

Further research

Needed to fully understand the properties and potential uses of the compound

InChI:InChI=1/C13H12FNO2/c14-8-2-4-11-10(6-8)9-3-1-7(5-12(16)17)13(9)15-11/h2,4,6-7,15H,1,3,5H2,(H,16,17)

Upstream product

• 393509-21-2 ethyl (7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate 
• 20826-94-2 ethyl (2-oxocyclopentyl)acetate 
• 61272-76-2 4-fluoro-2-iodoaniline 
• 371-40-4 4-fluoroaniline 
• 1003-98-1 2-bromo-4-fluoroaniline 
• 571170-84-8 [2-(2-bromo-4-fluoro-phenylimino)-cyclopentyl]-acetic acid ethyl ester 

Downstream Products

• 393509-23-4 (5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid 
• 571170-77-9 laropiprant 
• 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 
• 794535-36-7 [5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid 
• 936337-07-4 methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 
• 393509-04-1 [5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid 
• 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 

Relevant academic research and scientific papers

An efficient enzyme-catalyzed kinetic resolution: Large-scale preparation of an enantiomerically pure indole-ethyl ester derivative, a key component for the synthesis of a prostaglandin D2 receptor antagonist, an anti-allergic rhinitis drug can

Three racemic esters including indole-ethyl ester 1 as well as its related derivatives 3 and 4 in Scheme 1, all synthetic intermediates for the preparation of chiral compound 5, were used as substrates to evaluate the catalytic potentials of a panel of co

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.

Method of Treating Pathological Blushing

A method of treating pathological blushing is disclosed wherein the patient is administered a DP receptor antagonist. Compositions containing DP antagonists are also included.

METHOD OF TREATING ATHEROSCLEROSIS, DYSLIPIDEMIAS AND RELATED CONDITIONS

A method of treating atherosclerosis is disclosed wherein nicotinic acid or another nicotinic acid receptor agonist is administered to the patient in combination with a DP receptor antagonist. The DP receptor antagonist is administered to reduce, prevent

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

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.

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 is disclosed wherein nicotinic acid or another nicotinic acid receptor agonist is administered to the patient in combination with a DP receptor antagonist. The DP receptor antagonist is administered to reduce, prevent or eliminate flushing that may otherwise occur.

Fluoro substituted cycloalkanoindoles, compositions containing such compounds and methods of treatment

Fluoro substituted cycloalkanoindole derivatives are antagonists of prostaglandins, and as such are useful for the treatment of prostaglandin mediated diseases.