On May 17, 2018, Devasthale, Pratik; Moore, Fang; Zhao, Guohua; Pieniazek, Susan Nicole; Selvakumar, Kumaravel; Dhanusu, Suresh; Panda, Manoranjan; Marcin, Lawrence R. published a patent.Application In Synthesis of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate The title of the patent was Cyclobutane- and azetidine-containing mono- and spirocyclic compounds as alpha v integrin inhibitors and their preparation. And the patent contained the following:
The invention provides compounds of formula I or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds are antagonists to αv- containing integrins. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with dysregulation of av-containing integrins, such as pathol. fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions Compounds of formula I wherein A is a covalent bond, CO, O, C1-3 alkoxy, CONH and derivatives, etc.; E is cyclobutylene, azetidinylene, and [3.3.0]bicyclic moiety; X is C1-5 alkylene and (un)substituted phenylene; Y is a bond, CO, O, NH and derivatives, etc.; R1 is (un)substituted imidazolylamino, (un)substituted pyridinylamino, (un)substituted benzimidazolylamino, guanidino, etc.; R3 is H, C1-6 alkyl, C3-10 cycloalkyl, C6-10 aryl, etc.; R4 is H, halo, C1-6 alkyl, C3-10 carbocyclyl,e tc.; R4a is H, halo and C1-6 alkyl, R5 is H, C1-6 alkyl, Ph, benzyl, etc.; Z is N and CH; and pharmaceutically acceptable salts thereof, are claimed. Example compound II•TFA was prepared by a multistep procedure (procedure given). The invention compounds were evaluated for their αVβ6 inhibitory activity. From the assay, it was determined that compound II exhibited IC50 value of 420 nM. The experimental process involved the reaction of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate(cas: 445490-78-8).Application In Synthesis of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate
The Article related to cyclobutane azetidine containing spirocycle preparation alpha v integrin inhibitor, Heterocyclic Compounds (One Hetero Atom): Spiro Compounds With One Hetero Atom In Each Ring and other aspects.Application In Synthesis of tert-Butyl 7-(2-hydroxyethyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxylate
Referemce:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem