On June 16, 2011, Bollu, Venkataiah; Boren, Brant Clayton; Dalgard, Jackline; Flatt, Brenton T.; Haq, Nadia; Hudson, Sarah; Mohan, Raju; Morrissey, Michael; Pratt, Benjamin published a patent.Safety of Ethyl 3-fluoro-4-methylbenzoate The title of the patent was Azole compounds as TGR5 agonists and their preparation. And the patent contained the following:
The invention relates to TGR5 agonists of structural formula I, pharmaceutically acceptable salts thereof, compositions thereof, and use of the compounds and compositions for treating diseases. The invention also comprises use of the compounds in and for the manufacture of medicaments, particularly for treating diseases. Compounds of formula I wherein X is N and CR4; R1 is Rc; X can be CRc when R1 is (un)substituted phenyl; Rc is (un)substituted Ph, C5-6 cycloalkyl, CH2-Ph, heteroaryl, etc.; R2 is (CR2)p-Y-(CR2)q-Rd; p and q are independently 0 and 1; each R is independently H, C1-3 alkyl, halo, OH and CH2OH; Y is bond, S, SO2, CHOH, O, etc.; Rd is (un)substituted C6-10 aryl, (un)substituted NH-Ph, (un)substituted cycloalkyl, etc.; R5 is C(R8)2-Ph, C(R8)2-naphthalenyl, (un)substituted C(R8)2-heteroaryl; each R8 is independently H, halo and Me; both R8 is taken together to form C3-6 cycloalkyl and 3- to 6-membered heterocycloalkyl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by amidation of 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorobenzoic acid with (2-aminoethyl)trimethylammonium chloride hydrochloride. All the invention compounds were evaluated for their TGR5 agonistic activity. From the assay, it was determined that compound II exhibited EC50 values of < 100 nM. The experimental process involved the reaction of Ethyl 3-fluoro-4-methylbenzoate(cas: 86239-00-1).Safety of Ethyl 3-fluoro-4-methylbenzoate
The Article related to azole preparation tgr5 agonist, Heterocyclic Compounds (More Than One Hetero Atom): Imidazoles and other aspects.Safety of Ethyl 3-fluoro-4-methylbenzoate
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