On November 25, 1997, Berryman, Kent Alan; Doherty, Annette Marian; Edmunds, Jeremy John; Patt, William Chester; Plummer, Mark Stephen; Repine, Joseph Thomas published a patent.Quality Control of Methyl 2-(3-formylphenyl)acetate The title of the patent was Preparation of 3,5-diphenyl-2(5H)-furanone derivatives as nonpeptide endothelin I antagonists. And the patent contained the following:
Novel nonpeptide antagonists of endothelin I represented by formula [I; R1 = (un)substituted C3-12 cycloalkyl, Ph substituted with 1-5 substituents, naphthyl or heteroaryl optionally substituted with 1-5 substituents; R2 = C1-12 linear or branched alkyl, C3-12 linear or branched cycloalkyl, aryl optionally substituted with 1-5 substituents, heteroaryl optionally substituted with 1-3 substituents; R3 = (un)substituted C1-12 linear or branched alkyl, (un)substituted C3-12 cycloalkyl, aryl optionally substituted with 1-5 substituents, heteroaryl optionally substituted with 1-3 substituents; R4 = OH, OR5, (CH2)nOR5; wherein R5 = (un)substituted C1-7 alkyl; X = O, S] or tautomeric open chain keto-acids forms thereof or pharmaceutically acceptable salt thereof are prepared Also described are pharmaceutical compositions of the above compounds, which are useful in treating elevated levels of endothelin, acute and chronic renal failure, hypertension, myocardial infarction, myocardial ischemia, cerebral vasospasm, cerebral ischemia, cerebral infarction, cirrhosis, septic shock, congestive heart failure, endotoxic shock, subarachnoid hemorrhage, arrhythmia, asthma, preeclampsia, atherosclerotic disorders including Raynaud’s disease and restenosis, angina, cancer, pulmonary hypertension, ischemic disease, gastric mucosal damage, hemorrhagic shock, ischemic bowel disease, stroke, benign prostatic hyperplasia (BPH), and diabetes. Thus, Me 2-benzoyl-2-phenylacetate derivative (II) and 3,4,5-trimethoxybenzladehyde were refluxed in the presence of NaOMe in MeOH for 18 h and the solution was treated with AcOH and refluxed an addnl. 72 h, followed by saponification of the product with 1N aqueous NaOH and acidification to give 28% I (X = O, R1 = Q, R2 = 3,4,5-trimethoxyphenyl, R3 = 4-methoxyphenyl, R4 = OH). The latter compound in vitro showed an antagonism of endothelin I-stimulated vasoconstriction in the rabbit femoral artery and sarafotoxin 6c-stimulated vasoconstriction in the rabbit pulmonary artery with pA2 values of 0.00025 and 0.34, resp. The experimental process involved the reaction of Methyl 2-(3-formylphenyl)acetate(cas: 142327-44-4).Quality Control of Methyl 2-(3-formylphenyl)acetate
The Article related to acute renal failure, angina pectoris, antiarrhythmics, antiasthmatics, antiatherosclerotics, antidiabetic agents, antihypertensives, antitumor agents, benign prostatic hyperplasia, brain infarction, brain ischemia, cerebral artery spasm, chronic renal failure, cirrhosis, coronary restenosis, gastric mucosa (damage), heart failure and other aspects.Quality Control of Methyl 2-(3-formylphenyl)acetate
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