专利号:US-4314066-A 优先权日:1976-11-08 标题 :Synthesis of tetramisole, levamisole and their derivatives 发明人:RAGHU SIVARAMAN; HOFFMANN ARTHUR K; SINGH BALWANT 权利人:AMERICAN CYANAMID CO 摘要:A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives, and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of the anthelmintic levamisole, (-)-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives through conventional resolution procedures. The new process also permits the direct manufacture of optically active 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidone and their 3-acylated derivatives, optically active 1-(2-alkoxyethyl)-4-phenylimidazolidine-2-thiones, and levamisole, the levorotatory isomer of tetramisole, using catalytic amounts of a chiral reducing agent, with the elimination of conventional resolution procedures.
专利号:US-4370482-A 优先权日:1978-02-15 标题:Synthesis of tetramisole, levamisole and their derivatives 发明人:RAGHU SIVARAMAN; HOFFMANN ARTHUR K; SINGH BALWANT 权利人:AMERICAN CYANAMID CO 摘要:A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives, and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of the anthelmintic levamisole, (-)-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazols, and its derivatives through conventional resolution procedures. The new process also permits the direct manufacture of optically active 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidone and their 3-acylated derivatives, optically active 1-(2-alkoxyethyl)-4-phenylimidazolidine-2-thiones, and levamisole, the levorotatory isomer of tetramisole, using catalytic amounts of a chiral reducing agent, with the elimination of conventional resolution procedures.
专利号:US-4310672-A 优先权日:1976-04-26 标题 :Synthesis of intermediates for tetramisole, levamisole and their derivatives 发明人:RAGHU SIVARAMAN; HOFFMANN ARTHUR K; SINGH BALWANT 权利人:AMERICAN CYANAMID CO 摘要:A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of tetramisole, di-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.
专利号:US-4620009-A 优先权日:1980-03-17 标 题 :Synthesis of intermediates for tetramisole, levamisole and their derivatives 发明人:RAGHU SIVARAMAN; HOFFMANN ARTHUR K; SINGH BALWANT 权利人:CYANAMID AGRICULTURAL DE PUERT 摘要:A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of tetramisole, dl-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.
专利号:US-4139707-A 优先权日:1976-11-08 标题 :Intermediates for synthesis of tetramisole, levamisole and their derivatives 发明人:RAGHU SIVARAMAN; HOFFMANN ARTHUR K; SINGH BALWANT 权利人:AMERICAN CYANAMID CO 摘要:A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of tetramisole, dl-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.
专利号:US-4090025-A 优先权日:1976-04-26 标题 :Intermediates for synthesis of tetramisole, levamisole and their derivatives 发明人:RAGHU SIVARAMAN; HOFFMANN ARTHUR KENTARO; SINGH BALWANT 权利人:AMERICAN CYANAMID CO 摘要:A process for the manufacture of 1-(2-alkoxyethyl)-4-phenyl-4-imidazolin-2-ones, 1-(2-alkoxyethyl)-4-phenyl-2-imidazolidones, 1-(2-alkoxyethyl)-4-phenyl-imidazolidine-2-thiones, certain of the corresponding 1-(2-hydroxyethyl) derivatives and their 3-acylated derivatives, and certain related compounds which are all useful as intermediates in a new process for the manufacture of tetramisole, dl-2,3,5,6-tetrahydro-6-phenylimidazo-[2,1-b]thiazole, and its derivatives. The compound tetramisole is useful as an anthelmintic.
1: Vaezi Z, Amini A. Cocaine- and Levamisole-Induced Vasculitis (CLIV). Cureus. 2025 Sep 19;17(9):e92701. doi: 10.7759/cureus.92701. 2: Amaral PEM, Beane SO, Albarouki A, Tan MJ, Schoenberger MJ, Yao Y, Liu L, Uljon SN, Zhu Y, Hall DC Jr, Qiu Y. Rising illicit drug Adulterants: Xylazine and levamisole. Clin Biochem. 2025 Jun;137:110912. doi: 10.1016/j.clinbiochem.2025.110912. Epub 2025 Mar 11. 13(17):5116. doi: 10.3390/jcm13175116. 4: Gholami MH, Rassouli A, Mirzaei S, Hashemi F. The potential immunomodulatory effect of levamisole in humans and farm animals. J Adv Vet Anim Res. 2023 Dec 31;10(4):620-629. doi: 10.5455/javar.2023.j717.
合成参考文献
参考文献:10.1186/2046-0481-63-8-498 摘要:Gutierrez J, Eisenberg RL, Koval NJ, Armstrong ER, Tharappel J, Hughes CG, Tobin T. Pemoline and tetramisole 'positives' in English racehorses following levamisole administration. Irish Veterinary Journal. 2010 Aug 01;63(8):498. doi: 10.1186/2046-0481-63-8-498.