US 11,746,114 B2
Thermally sensitive protecting groups for cysteine for peptide cyclization and selective disulfide bond formation
John Frederick Trant, LaSalle (CA); Sarah Nasri, LaSalle (CA); Maryamalsadat Kosar, Windsor (CA); Sanaz Nadimi, Windsor (CA); Mohaddeseh Dashti Nejad Pour, Windsor (CA); Purshotam Sharma, Windsor (CA); and Seyedeh Maryamdokht Taimoory, Montreal (CA)
Filed by University of Windsor, Windsor (CA)
Filed on Feb. 4, 2022, as Appl. No. 17/665,253.
Application 17/665,253 is a continuation in part of application No. 17/468,048, filed on Sep. 7, 2021, granted, now 11,560,387.
Application 17/468,048 is a continuation of application No. 16/985,815, filed on Aug. 5, 2020, abandoned.
Claims priority of provisional application 62/883,332, filed on Aug. 6, 2019.
Prior Publication US 2022/0153749 A1, May 19, 2022
Int. Cl. C07D 491/18 (2006.01); C07K 1/06 (2006.01)
CPC C07D 491/18 (2013.01) [C07K 1/067 (2013.01)] 25 Claims
 
1. A protecting group for protecting a cysteine residue, the protecting group having structural formula 11 or 12:

OG Complex Work Unit Chemistry
wherein
R is an electron withdrawing group or a leaving group;
Ar is optionally substituted aryl or optionally substituted heteroaryl;
X, Y, Z and Z1 are independently of each other oxygen, sulfur, nitrogen or phosphorus;
R1 and R2 are independently of each other hydrogen, hydroxyl, halo, alkyl, alkenyl, alkynyl, cycloalkyl, heterocycloalkyl, aryl, aralkyl, heteroaryl, heteroaralkyl, formyl, haloformyl, carbonyl, carboxyl, alkoxy, alkoxycarbonyl, (alkoxycarbonyl)oxy, carbamoyl, amino, amido, imino, imido, azo, cyanato, isocyanato, cyano, nitro, sulfanyl, thiocyanato or phosphono, each of which is optionally substituted; and
n and n1 are independently of each other an integer between 1 and 12, inclusive.