147283-87-2

Usage

Uses

Used in Pharmaceutical Synthesis:
Methyl [3-[[(trifluoromethyl)sulfonyl]oxy]phenyl]-acetate is used as an intermediate in the synthesis of m-Isobutyl Ibuprofen (I780080) for its role in the development of potent noncompetitive interleukin-8 inhibitors. This application is significant due to the compound's ability to contribute to the creation of effective anti-inflammatory agents.
Used in the Study of Ibuprofen Impurities:
In the pharmaceutical industry, methyl [3-[[(trifluoromethyl)sulfonyl]oxy]phenyl]-acetate is utilized in the study of Ibuprofen (I140000) impurities, specifically m-Isobutyl Ibuprofen (Ibuprofen EP Impurity A). This application is essential for ensuring the quality, safety, and efficacy of Ibuprofen-based medications by understanding and controlling the presence of impurities in the final product.

Upstream product

• 37595-74-7 N,N-phenylbistrifluoromethane-sulfonimide 
• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 67-56-1 methanol 
• 621-37-4 m-hydroxyphenylacetic acid 

Downstream Products

• 478375-42-7 methyl 2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetate 
• 859828-49-2 methyl 2-{3-(trifluoromethanesulfonyloxy)phenyl}propanoate 
• 906739-26-2 methyl 3-(trifluoromethanesulfonyloxy)phenyldiazoacetate 
• 1299295-04-7 methyl 2-(3-{[3-methoxy-5-(trifluoromethyl)phenyl]amino}phenyl)propanoate 
• 1299295-19-4 methyl 2-{3-[1-hex-1-en-1-yl]phenyl}propanoate 
• 1299295-05-8 2-(3-{[(trifluoromethyl)sulphonyl]oxy}phenyl)propanoic acid 
• 1299295-03-6 2-(3-{[3-methoxy-5-(trifluoromethyl)phenyl]amino}phenyl)propanoic acid 
• 1056455-02-7 [3-(2'-fluoro-4'-trifluoromethyl-biphenyl-3-sulfonyl)-phenyl]-acetic acid methyl ester 
• 71912-71-5 3-(2-hydroxy-1-ethyl)-1,1'-biphenyl 
• 597584-97-9 methyl 3-cyclobutyl-2-[4'-(4-methylpiperazin-1-yl)-1,1'-biphenyl-3-yl]propanoate 

Relevant academic research and scientific papers

2-ARYL-PROPIONAMIDE DERIVATIVES USEFUL AS BRADYKININ RECEPTOR ANTAGONISTS AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

(R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B 1 pathway.

2-aryl-propionamide derivatives useful as bradykinin receptor antagonists and pharmaceutical compositions containing them

(R,S) 2-aryl-propionamide derivatives, or their single enantiomers (R) and (S) are disclosed useful in the treatment or prevention of symptoms and disorders such as pain and inflammation associated with the bradykinin B1 pathway.

PPAR active compounds

Compounds are described that are active on at least one of PPARα, PPARδ, and PPARγ, which are useful for therapeutic and/or prophylactic methods involving modulation of at least one of PPARα, PPARδ, and PPARγ.

PPAR ACTIVE COMPOUNDS

Compounds are described that are active on at least one of PPARα, PPARδ, and PPARγ, which are useful for therapeutic and/or prophylactic methods involving modulation of at least one of PPARα, PPARδ, and PPARγ.

Diversity synthesis using the complimentary reactivity of rhodium(II)- and palladium(II)-catalyzed reactions

Rhodium(II)-catalyzed reactions of aryldiazoacetates can be conducted in the presence of iodide, triflate, organoboron, and organostannane functionality, resulting in the formation of a variety of cyclopropanes or C-H insertion products with high stereoselectivity. The combination of the rhodium(II)-catalyzed reaction with a subsequent palladium(II)-catalyzed Suzuki coupling offers a novel strategy for diversity synthesis.

3,4,5-Trisubstituted isoxazoles as novel PPARδ agonists. Part 2

A series of PPARδ-selective agonists was investigated and optimized for a favorable in vivo pharmacokinetic profile. Isoxazole LCI765 (17d) was found to be a potent and selective PPARδ agonist with good in vivo PK properties in mouse (Cmax = 5.1 μM, t1/2 = 3.1 h). LCI765 regulated expression of genes involved in energy homeostasis in relevant tissues when dosed orally in C57BL6 mice. A co-crystal structure of compound LCI765 and the LBD of PPARδ is discussed.

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.

2-Arylpropionic CXC chemokine receptor 1 (CXCR1) ligands as novel noncompetitive CXCL8 inhibitors

The CXC chemokine CXCL8/IL-8 plays a major role in the activation and recruitment of polymorphonuclear (PMN) cells at inflammatory sites. CXCL8 activates PMNs by binding the seven-transmembrane (7-TM) G-protein-coupled receptors CXC chemokine receptor 1 (CXCR1) and CXC chemokine receptor 2 (CXCR2). (R)-Ketoprofen (1) was previously reported to be a potent and specific noncompetitive inhibitor of CXCLS-induced human PMNs chemotaxis. We report here molecular modeling studies showing a putative interaction site of 1 in the TM region of CXCR1. The binding model was confirmed by alanine scanning mutagenesis and photoaffinity labeling experiments. The molecular model driven medicinal chemistry optimization of 1 led to a new class of potent and specific inhibitors of CXCL8 biological activity. Among these, repertaxin (13) was selected as a clinical candidate drug for prevention of post-ischemia reperfusion injury.

AMINOALCOHOL DERIVATIVES

The present invention relates to a compound formula [I]: wherein Y is bond,--O--(CH2)n--(in which n is 1, 2, 3 or 4), etc., Z is cyano, tetrazolyl, etc., R1 is hydrogen, lower alkyl, etc., R2 is hydrogen or an amino protective group, R3 is hydrogen or lower alkyl, R4 is hydrogen or lower alkyl, R5 and R8 are each independently hydrogen, halogen, hydroxy, lower alkyl, etc., R6 is hydrogen, lower alkyl, etc., R9 is hydrogen or lower alkyl, and i is 1 or 2, or a salt thereof. The compound [I] of the present invention and pharmaceutically acceptable salts thereof are useful for the prophylactic and/or the therapeutic treatment of pollakiurea or urinary incontinence.

A novel class of nonpeptidic biaryl inhibitors of human cathepsin K

A novel series of nonpeptidic biaryl compounds was identified as potent and reversible inhibitors of cathepsin K. The P2-P3 amide bond of a known amino acetonitrile dipeptide 1 was replaced with a phenyl ring, thereby giving rise to this biaryl series that retained potency vs cathepsin K and showed an improved selectivity profile against other cathepsins. Structural modification within this series resulted in the identification of compound (R)-2, a potent human cathepsin K inhibitor (IC50 = 3 nM) that is selective versus cathepsins B (IC50 = 3950 nM), L (IC50 = 3725 nM), and S (IC50 = 2010 nM). In an in vitro assay involving rabbit osteoclasts and bovine bone, compound (R)-2 inhibited bone resorption with an IC 50 of 95 nM. It was shown that, unlike some peptidic nitrile inhibitors of cysteine proteases, the nitrile moiety of (R)-2 is not converted to the corresponding amide 3 by cathepsin K. This indicates that this class of nonpeptidic nitrile inhibitors is unlikely to be hydrolyzed by cysteine proteases. Furthermore, the inhibition of cathepsin K by compound (R)-2 was shown to be fully reversible and not observably time-dependent. To demonstrate the efficacy of compound (R)-2 in vivo, it was administered to ovariectomized (OVX) rhesus monkeys at 20 mg/kg, po once daily for 8 days, and a urinary marker of bone turnover, N-telopeptide of type I collagen (uNTx), was measured. During the eight-day dosing period, the mean reduction by compound (R)-2 in uNTx was 80% (p 0.001). This demonstrates that inhibition of cathepsin K leads to an inhibition of this bone resorption marker in OVX rhesus monkeys and strongly suggests that inhibition of cathepsin K is a viable therapeutic approach for the treatment of osteoporosis.