201748-37-0

Upstream product

• 695-96-5 2-bromo-4-chlorophenol 
• 107-30-2 chloromethyl methyl ether 

Downstream Products

• 162269-57-0 (5-Chloro-2-hydroxy-phenyl)-(3-hydroxy-pyridin-2-yl)-methanone 
• 162269-13-8 (5-Chloro-2-hydroxy-phenyl)-(3-hydroxy-pyridin-2-yl)-methanone O-tert-butyl-oxime 
• 1240490-47-4 5-chloro-2-methoxymethoxy-[carboxyl-⁽¹⁴⁾C]benzoic acid 
• 1240289-05-7 3-{[5-chloro-2-(methoxymethoxy)phenyl]ethynyl}-4-methylphenyl propyl sulfone 
• 1240286-81-0 2-{4-chloro-2-[(2-methyl-5-propylsulfonylphenyl)ethynyl]phenoxy}propanoic acid 
• 1240286-78-5 2-{4-chloro-2-[(2-methyl-5-propylsulfonylphenyl)ethynyl]phenoxy}butanoic acid 
• 1240286-79-6 2-{4-chloro-2-[(2-methyl-5-propylsulfonylphenyl)ethynyl]phenoxy}pentanoic acid 
• 1240286-80-9 2-{4-chloro-2-[(2-methyl-5-propylsulfonylphenyl)ethynyl]phenoxy}-4-methylpentanoic acid 
• 1240289-06-8 4-chloro-2-[(2-methyl-5-propylsulfonylphenyl)ethynyl]phenol 
• 1240289-07-9 ethyl 2-(4-chloro-2-{[2-methyl-5-(propylsulfonyl)phenyl]ethynyl}phenoxy)butanoate 
• 1357176-51-2 (2S)-2-((R)-(5-chloro-2-(methoxymethoxy)phenyl)(6-methoxyquinolin-4-yl)methyl)-5-vinylquinuclidine 

Relevant academic research and scientific papers

Synthesis of indole-fused heteroacenes by cascade cyclisation involving rhodium(ii)-catalysed intramolecular C-H amination

Heteroacenes are potentially important materials for organic electronics and their syntheses are of topical interest. Herein we report the development of a catalytic, redox-neutral reaction for the synthesis of the 5,10-dihydroindolo[3,2-b]indole class of

Discovery of potent, selective, and orally bioavailable alkynylphenoxyacetic acid CRTH2 (DP2) receptor antagonists for the treatment of allergic inflammatory diseases

New phenoxyacetic acid antagonists of CRTH2 are described. Following the discovery of a hit compound by a focused screening, high protein binding was identified as its main weakness. Optimization aimed at reducing serum protein binding led to the identification of several compounds that showed not only excellent affinities for the receptor (41 compounds with Ki 50 100 nM; PGD2-induced eosinophil shape change). Additional optimization of the PK characteristics led to the identification of several compounds suitable for in vivo testing. Of these, 19k and 19s were tested in two different pharmacological models (acute FITC-mediated contact hypersensitivity and ovalbumin-induced eosinophilia models) and found to be active after oral dosing (10 and 30 mg/kg).

PHENOXY ACETIC ACID DERIVATIVES

The present invention provides phenoxyacetic acid derivatives of Formula (I) for the treatment of CRTH2 related disorders and disease selected from asthma, atopic dermatitis and inflammatory dermatoses.

Carbon-14 radiosynthesis of 4-(5-chloro-2-hydroxyphenyl)-3-(2-hydroxyethyl) -6-(trifluoromethyl)-[4-14C]quinolin-2(1H)-one (XEN-D0401), a novel BK channel activator

A method has been developed for the carbon-14 radiosynthesis of [ 14C]XEN-D0401, a 4-(2-hydroxyphenyl)quinolin-2(1H)-one derivative. The radiosynthetic route involves a series of ortho-lithiations directed by both 2-methoxymethyl (MOM) and pivaloyl protecting groups. This is demonstrated in the first key radiochemical step between the reaction of 5-chloro-2- methoxymethoxy-[carboxyl-14C]benzoic acid methyl ester [ 14C]-3 and the ortho-lithiated intermediate generated from 2,2-dimethyl-N-(4-trifluoromethylphenyl)-propionamide (2) to afford the protected benzophenone [14C]-4. The other key radiochemical step utilizes a variation of the Friedlaender quinoline synthesis, which involves a base catalysed, one-pot condensation process between (2-amino-5- trifluoromethyl-phenyl)-(5-chloro-2-methoxymethoxy-phenyl)-[14C] methanone [14C]-5 and c-butyrolactone to give MOM-protected [ 14C]-6. On MOM deprotection, [14C]XEN-D0401 was isolated with a radiochemical purity of >97%, with a specific activity of 55 mCi/mmol from seven radiochemical steps, starting from barium [14C]carbonate in a radiochemical yield of 10.5%. Copyright

Synthesis and biological activity of novel 2-(α- alkoxyimino)benzylpyridine derivatives as K+ channel openers

The search for novel K+ channel openers with a non-benzopyran skeleton, unlike cromakalim, led to the discovery of a new series of (Z)-2-(α- alkoxyimino)benzylpyridine derivatives. Synthesis was achieved by using a (Z)-dominant condensation reaction of henzoylpyridines with O- alkylhydroxylamines, followed by m-chloroperhenzoic acid (m-CPBA) oxidation. The compounds were tested for their vasorelaxant activity in tetraethylammonium chloride (TEA) and BaCl2- and high KCl-induced contraction of rat aorta to identify potential K+ channel openers, and also for their effects on the coronary blood flow (CBF) after intracoronary injection in anesthetized dogs. A large number of the 2-(α- alkoxyimino)benzylpyridines strongly inhibited TEA and BaCl2-induced contraction, had no effect on 80 mM KCl-induced contraction, and increased the CBF to more than 200% of the basal flow at 10-30μg/dog. In particular, (Z)-2-[5-bromo-α-(tert-butoxyimino)-4-fluoro-2-hydroxybenzyl]-3- hydroxypyridine 1-oxide (7d) showed highly potent vasorelaxant activity (EC50=0.28μM) comparable to that of levcromakalim (EC50=0.17 μM), and gave a significantly longer-lasting increase (T ( 1/4 ) = 30 min) in the CBF compared to levcromakalim, nicorandil, nitroglycerin, or diltiazem (T( 1/4 )=5.2, 0.9, 0.4, and 2.2 min, respectively). It also exhibited a stable and long-lasting hypotensive effect (over 7h) upon oral administration of 1 mg/kg in spontaneously hypertensive rats (SHRs).