On December 3, 2020, Sebhat, Iyassu; He, Shuwen published a patent.Formula: C8H15NO2 The title of the patent was Preparation of 3-cyclopropyl-3-(3-acyloxyphenyl)propanoic acid derivatives as Gpr40 agonists. And the patent contained the following:
The compounds represented by formula I [Z = C(O)OH, C(O)OR5, C(O)NHR6, C(O)NHS(O)2R5, S(O)2NHC(O)R5, P(O)(R5)OR6, P(O)(OR6)2, S(O)2OR6; or Z = (un)substituted 4- or 5-membered heterocycle; R5 = each (un)substituted C1-6 alkyl, C3-6 cycloalkyl, Ph, or phenyl-C1-6 alkyl; R6 = hydrogen or each (un)substituted C1-6 alkyl, C3-6 cycloalkyl, Ph, or phenyl-C1-6 alkyl; R1, R2, R3, R4 = each independently hydrogen, halogen, OH, or each (un)substituted C1-6 alkyloxy, C1-6 alkyl, C3-6 cycloalkyl, or 3- to 6-membered heterocycloalkyl; Y1, Y2, Y3, or Y4 = each independently N, CH, or CRY; each RY = independently halogen, cyano, OH, NH2, or each (un)substituted C1-6 alkoxy, NH-(C1-6 alkyl), N-(C1-6 alkyl)2, C1-6 alkyl, C3-6 cycloalkyl, or 3- to 6-membered heterocycloalkyl; L1 = *-OC(O)-, or *-C(O)O-, wherein * represents the connection to Ring B; Ring B = each (un)substituted arylene, heteroarylene, C3-10 cycloalkylene, or 3- to 10-membered heterocycloalkylene; L2 = a bond or each (un)substituted C1-6 alkylene, or -(C1-6 alkylene)-O-] or pharmaceutically acceptable salts, solvates, stereoisomers, or prodrugs thereof are prepared The compounds I are gut-restricted compounds and full or partial G protein-coupled receptor 40 (GPR40) agonists and useful for the treatment of conditions or disorders involving the gut-brain axis. The conditions or disorder is (1) a metabolic disorder such as type 2 diabetes, hyperglycemia, metabolic syndrome, obesity, hypercholesterolemia, nonalcoholic steatohepatitis, or hypertension or (2) a nutritional disorder such as short bowel syndrome, intestinal failure, or intestinal insufficiency. Thus, a solution of 0.28 g 3-[(diisopropylamino)methyl]-4-(5-fluoro-2-methoxypyridin-4-yl)benzoic acid and 0.13 g Me (S)-3-cyclopropyl-3-(3-hydroxyphenyl)propanoate in 3 mL CH2Cl2 was treated with 35 mg 4-dimethylaminopyridine and 0.18 g DCC and stirred at 25° for 16 h to give, after workup and purification using preparative TLC, (S)-3-cyclopropyl-3-[3-[[3-[(diisopropylamino)methyl]-4-(5-fluoro-2-methoxypyridin-4-yl)benzoyl]oxy]phenyl]propanoic acid (II). II showed an agonist activity with EC50 of ≤10 nM in a human GPR40 assay. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Formula: C8H15NO2
The Article related to acyloxyphenylcyclopropylpropanoic acid preparation gpr40 agonist, metabolic disorder type 2 diabetes treatment gpr40 agonist preparation, hyperglycemia metabolic syndrome obesity treatment gpr40 agonist preparation, hypercholesterolemia nonalcoholic steatohepatitis hypertension treatment gpr40 agonist preparation and other aspects.Formula: C8H15NO2
Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem