Use of Oxugeli and its derivatives

April 13, 2022

Elagolix, CAS number: 834153-87-6, is an oral GNRH antagonist, used in medicine, chemical engineering, experimental research, etc. , through the pituitary GnRH receptor competitive binding to inhibit endogenous GNRH signal transduction, it is used to treat sex hormone mediated diseases such as uterine fibroids and endometriosis. Published August 8,201714,99447.8 a group of methods for deuterated receptor antagonist derivatives, known as GNRH, have been developed for the treatment of sex hormone related disorders in men and women.

PCT PATENT WO2005007165A reported the synthetic method of Oxaliplatin, using 2-fluoro-6-trifluoromethylbenzonitrile as raw material, cyanide was reduced by Borane and then condensed with urea in the presence of hydrochloric acid to obtain 1-(2-fluoro-6-trifluoromethylphenylethyl) urea intermediate, the Intermediate 1-[2-fluoro-6-(trifluoromethyl) Benzyl ]-6-methylpyrimidine-2,4(1h, 3h)-diketone was obtained by cyclization with diketene, after bromination, alkylation with Amine, Suzuki coupling reaction with 2-fluoro-3-methoxyphenylboric acid and acid decomposition to remove the BOC protective group, the final product was obtained by condensation and hydrolysis with 4-bromobutyric acid.

This route has a long linear step, a complicated process, and a low total yield and a high cost for Suzuki coupling reaction of phenylboronic acid with Tetrakis(triphenylphosphine)Palladium(0) .

US patent US8765948B reports a new method for the synthesis of oxlargol from Ethyl 2-(2-fluoro-3-methoxyphenyl) formate via sodium borohydride reduction and bromination with Acetonitrile in the presence of zinc powder, the Amino Group was protected by phenyl carbonate and then reacted with (r)-tert-butyl (2-amino-1-phenylethyl) Amino carbonic acid and Ester in the presence of base to obtain the mother ring molecule, n-alkylation of benzyl bromide with benzyl bromide intermediate was carried out to obtain Oxalgoritrin, a key intermediate.

Although this route greatly simplifies the reaction steps, the starting materials and intermediates are special and the cost of raw materials is high, we still need to find a simple process, high yield, low cost, suitable for industrial production method synthesis of oxacillin.

(the above information comes from the Internet.)

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