On December 12, 2000, Ankersen, Michael; Stidsen, Carsten Enggaard; Crider, Michael Albert published a patent.Quality Control of N1-(5-Bromopyrid-2-yl)ethane-1,2-diamine The title of the patent was Use of pyridinylaminoalkyl- and imidazolylalkyl-substituted thioureas, isothioureas, and guanidines as somatostatin agonists and antagonists, for treating diseases related to the eye. And the patent contained the following:
The invention relates to the use of somatostatin receptor ligands of nonpeptide origin, e.g., I or II, or a pharmaceutically acceptable salt thereof [wherein: m = 2, 3, 4, 5 or 6; n = 1, 2 or 3; p = 1, 2, 3, 4, 5 or 6; R1, R2 = independently H or C1-6 alkyl optionally substituted with halo, amino, OH, alkoxy, or aryl; X = S, O, NH, NCOPh or N(CN); A = (hetero)aryl optionally substituted with halo, amino, OH, NO2, C1-6 alkyl, C1-6 alkoxy, or aryl, B = (hetero)aryl optionally substituted with halo, amino, OH, C1-6 alkyl, C1-6 alkoxy, or aryl; D = (hetero)aryl or amino, optionally substituted with halo, amino, OH, C1-6 alkyl, C1-6 alkoxy, or aryl]. The compounds have high and/or selective affinity to the somatostatin receptor protein designated SSTR4, and are useful for the preparation of medicaments for treatment of diseases associated with adverse conditions of the retina and/or iris-ciliary body in mammals (no data). Such conditions include high intraocular pressure (IOP) and/or deep ocular infections. The diseases which may be treated are, e.g. glaucoma, stromal keratitis, iritis, retinitis, cataract, and conjunctivitis. Over 40 compounds are claimed for usage, and 27 synthetic examples are given. For instance, propane-1,3-diamine underwent a sequence of: (1) N-arylation with 2-bromopyridine (76%); (2) N-benzylation with NaH and 4-bromobenzyl bromide in DMSO (70%); (3) conversion of the N’-amine to an isothiocyanate using DCC and CS2 (88%); (4) amination of the isothiocyanate with 3-[1-(triphenylmethyl)imidazol-4-yl]propylamine (80%); and (5) deprotection of the trityl group with aqueous HCl in EtOH (99%), to give title compound III.2HCl. The experimental process involved the reaction of N1-(5-Bromopyrid-2-yl)ethane-1,2-diamine(cas: 199522-66-2).Quality Control of N1-(5-Bromopyrid-2-yl)ethane-1,2-diamine
The Article related to thiourea isothiourea guanidine pyridinylaminoalkyl imidazolylalkyl preparation somatostatin agonist antagonist, antiglaucoma somatostatin receptor agonist antagonist thiourea isothiourea guanidine preparation and other aspects.Quality Control of N1-(5-Bromopyrid-2-yl)ethane-1,2-diamine