On October 6, 2016, Jones, Alison; Kemp, Mark; Stockley, Martin; Gibson, Karl; Whitlock, Gavin published a patent.Category: pyrimidines The title of the patent was 1-Cyanopyrrolidine compounds as USP30 inhibitors and their preparation. And the patent contained the following:
The invention relates to compounds of formula I and method for the manufacture of inhibitors of deubiquitylating enzymes. In particular, the invention relates to the inhibition of ubiquitin C-terminal hydrolase 30 (USP30). The invention further relates to the use of DUB inhibitors in the treatment of conditions involving mitochondrial dysfunction and cancer. Compounds of formula I wherein Z is absent and CR6R7; Y is a bond, C0-3 alkylene-NR11-C0-3 alkylene and (un)substituted C1-3 alkylene; R1, R6, R7 and R8 are independently H, F, CN, OH, (un)substituted C1-3 alkyl and (un)substituted C1-3 alkoxy; R2 is H, (un)substituted C1-6 alkyl, (un)substituted C1-6 alkoxy, (un)substituted 4- to 10-membered heteroaryl, etc.; R3, R4 and R5 are independently (un)substituted alkyl and (un)substituted C1-3 alkoxy; R9 is H, CN, OH, (un)substituted C1-6 alkyl, etc.; R10 is H, (un)substituted C1-6 alkyl; R11 is H, (un)substituted C1-6 alkyl, 4- to 10-membered heteroaryl, heterocyclyl, aryl, etc.; R9R10 can be taken together to form (un)substituted heterocyclic ring; R10R11 can be taken together to form (un)substituted (mono/bi)cyclic ring; R12 is (un)substituted (mono/bi/tri)cyclic 3- to 14-membered heteroaryl, heterocyclyl, cycloalkyl and aryl; and pharmaceutically acceptable salts thereof, are claimed. Example compound II was prepared by amidation of 5-phenylpyridine-2-carboxylic acid with (R)-3-amino-1-(tert-butoxycarbonyl)pyrrolidine; the resulting tert-Bu (R)-3-(5-phenylpicolinamido)pyrrolidine-1-carboxylate underwent hydrolysis to give (R)-5-phenyl-N-(pyrrolidin-3-yl)picolinamide TFA, which underwent cyanation to give compound II. The invention compounds were evaluated for their USP30 inhibitory activity (data given). The experimental process involved the reaction of 5-Phenylpyrimidine-2-carboxylic acid(cas: 85386-20-5).Category: pyrimidines
The Article related to cyanopyrrolidine preparation usp30 inhibitor, Heterocyclic Compounds (One Hetero Atom): Pyrroles and Pyrrolizines and other aspects.Category: pyrimidines
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia