164992-12-5

Upstream product

• 186581-53-3 diazomethane 
• 16859-59-9 3-hydroxy-1(3H)-isobenzofuranone 
• 119-67-5 o-carboxybenzaldehyde 

Downstream Products

• 23206-20-4 4-hydroxy-3,4-dihydroisoquinolin-1(2H)-one 

Relevant academic research and scientific papers

BRIDGED AND FUSED HETEROCYCLIC ANTIDIABETIC COMPOUNDS

This invention provides for certain bridged and fused heterocyclic compounds of the formula (I) or a pharmaceutically acceptable salt, ester solvate or prodrug thereof wherein: L is: (II) and the other variables are defined herein; the inventive compounds are agonists of the G-protein coupled receptor 40 (GPR40, also known as free fatty acid receptor FFAR). This invention further relates to pharmaceutical compositions containing these compounds, and the use of these compounds to regulate insulin levels in a mammal. The compounds may be used, for example in the prevention and treatment of Type 2 diabetes mellitus and in the prevention and treatment of conditions related to Type 2 diabetes mellitus, such as insulin resistance, obesity and lipid disorders.

Aromatic Spiranes XXI [1]: Syntheses of Methyl Substituted Phthalaldehydic Acids and their Ethyl and Methyl Esters as Synthones for Syntheses of Methylated 2,2′-Spirobiindandiones

The isomeric methyl phthalaldehydic acids 11 were obtained from phthalides 4 by bromation (NBS) to the 3-bromo derivatives 7 and subsequent hydrolysis with water. 4 in turn were accessible from dimethyl methyl benzoates 1 by dibromination with NBS and subsequent thermical cyclization to the bromo derivatives 3 which, on catalytic dehalogenation, afforded the phthalides 4. Reaction of 11 with methanol or ethanol gave the pseudo-esters 13 and 14, resp. Short treatment of 11 with diazomethane on the other hand yielded the methyl formyl benzoates 15b to 15e. Prolonged reaction (several hours) gave the oxiranyl compounds 17; in addition, the acetonyl derivatives 18 were also found, obviously formed by a double methylene insertion into 15. All reactions proceeded with good to excellent yields.

A new synthetic route to isoquinolin-1(2H)-one derivatives from 3-hydroxyphthalides

A new synthetic route for the conversion of substituted 3-hydroxyphthalides into the corresponding isoquinolin-1(2H)-one was established. This method can be applied to the preparation of isoquinolin-1(2H)-ones with electron-withdrawing groups that are relatively difficult to synthesize by conventional procedures.