On October 7, 2021, Cheruvallath, Zacharia; Green, Jason; Johnson, Ben; Jones, Bejamin; Schleicher, Kristin; Sun, Huikai; Tang, Mingnam published a patent.Application In Synthesis of 5-Methylisoquinoline-1-carbonitrile The title of the patent was N-Heteroarylalkyl-2-(heterocyclyl and heterocyclylmethyl) acetamide derivatives as SSTR4 agonists and their preparation. And the patent contained the following:
Disclosed are compounds of formula I, and pharmaceutically acceptable salts thereof. This disclosure also relates to materials and methods for preparing compounds of formula I, to pharmaceutical compositions which contain them, and to their use for treating diseases, disorders, and conditions associated with SSTR4. Compounds of formula I wherein when X3 is NH and derivatives and O, X4 is a single bond, and X5 is N and CR5, and R1R2 are taken together to form (un)substituted benzene ring; when X3 is CR3c, X4 is N and CR4, and X5 is N and CR5, and R1R2 are taken together to form (un)substituted furan, (un)substituted pyrazole or (un)substituted benzene ring; L is O when A is CHR6; L is a bond when n is absent and CHR6; R3c and N are independently H, halo, OH, CN, (un)substituted C3-6 cycloalkyl, etc.; R6 is H; R5R6 can be taken together to form ethane-1,2-diyl bridge; R7 and R8 are independently H and (un)substituted C1-4 alkyl; R9 is H and (un)substituted C1-4 alkyl; R10 is azetidin-1-ylmethyl, pyrrolidin-1-ylmethyl and heterocyclyl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by amidation of 2-(1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid with 2-(1,7-dimethyl-1H-indazol-3-yl)propan-2-amine followed by hydrolysis; the resulting 7-(2-(1,7-dimethyl-1H-indazol-3-yl)propan-2-yl)-2-(pyrrolidin-2- yl)acetamide underwent reductive methylation with formaldehyde to give compound II. The invention compounds were evaluated for their SSTR4 inhibitory activity. From the assay, it was determined that compound II exhibited pEC50 value of 8.2 and pIC50 value of 7.2. The experimental process involved the reaction of 5-Methylisoquinoline-1-carbonitrile(cas: 1367744-24-8).Application In Synthesis of 5-Methylisoquinoline-1-carbonitrile
The Article related to heteroarylalkyl heterocyclylacetamide preparation sstr4 agonist, Heterocyclic Compounds (More Than One Hetero Atom): Pyrazoles and other aspects.Application In Synthesis of 5-Methylisoquinoline-1-carbonitrile
Referemce:
Isoquinoline – Wikipedia,
Isoquinoline | C9H7N – PubChem