专利号:US-5856500-A 优先权日:1997-03-11 标题:Synthesis of thiazole derivatives 发明人:MATTHEWS MICHAEL D; MALCOLM ARCELIO J 权利人:ALBEMARLE CORP 摘要:N- 4-(Cyanoethylthiomethyl)-2-thiazolyl!guanidine, is prepared by (a) mixing 1,3-dihaloacetone and 2-imino-4-thiobiuret in a suitable polar organic solvent at initial temperatures of about -10° to about 25° C., and agitating the mixture at about -10° to about 60° C. for at least about 1 hour; (b) heating the resultant mixture at about 40° to about 60° C. for at least about 0.5 hour; (c) mixing with the mixture from (b), thiourea and then water at about 40° to about 60° C. for a period of at least about 1 hour; (d) removing liquid polar solvent from the mixture of (c); and (e) mixing with the mixture from (d), 3-halopropionitrile and water-soluble alcohol, ether, or ether-alcohol, followed by aqueous alkali metal hydroxide while maintaining the temperature at below about 20° C., to form N- 4-(cyanoethylthiomethyl)-2-thiazolyl!guanidine. The process avoids isolating and purifying any of the intermediates, and can be conducted in the same vessel, as a 'one-pot' synthesis.
专利号:US-5856501-A 优先权日:1997-03-11 标题 :Synthesis of thiazole derivatives 发明人:MALCOLM ARCELIO J; WU TSE-CHONG 权利人:ALBEMARLE CORP 摘要:N- 4-(cyanoethylthiomethyl)-2-thiazolyl!guanidine--a key intermediate for preparing the pharmaceutical, famotidine--is produced by mixing in a liquid medium formed from a chemically indifferent organic solvent and water, and under an inert atmosphere, (i) a 2-guanidino-4-halomethylthiazole or a hydrohalide complex thereof, (ii) an S-(2-cyanoethyl)isothiourea or a hydrohalide complex thereof, and (iii) a strong alkali metal base. In lieu of (ii), an alkali metal salt of 2-cyanoethyl-1-thiol can be used, and in such case use of (iii) is optional, but preferable.
专利号:US-4656291-A 优先权日:1985-03-15 标 题 :Process for producing amidine sulfonic acids 发明人:MARYANOFF CYNTHIA A; PLAMPIN JAMES N; STANZIONE ROBIN C 权利人:MCNEILAB INC 摘要:An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): with H2O2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.
专利号:US-4781866-A 优先权日:1985-03-15 标题 :Process for producing amidine sulfonic acid intermediates for guanidines 发明人:MARYANOFF CYNTHIA A; PLAMPIN JAMES N; STANZIONE ROBIN C 权利人:MCNEILAB INC 摘要:An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): with H2O2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.
专利号:WO-9840367-A1 优先权日:1997-03-11 标题:Novel thiazole derivatives and their preparation 发明人:RAMACHANDRAN VENKATARAMAN; MALCOLM ARCELIO J 权利人:ALBEMARLE CORP 摘要:1-(4-Bromomethyl-2-thiazolyl)guanidine, and its acid addition salts, especially 1-(4-bromomethyl-2-thiazolyl)guanidine hydrobromide are novel compounds useful as starting materials for the synthesis of famotidine. These compounds can be produced without need for prolonged reaction periods at extremely low temperatures by mixing 1,3-dibromoacetone and 2-imino-4-thiobiuret in a suitable reaction medium. Moreover, the novel compounds can be selectively synthesized in good yield and purity from a raw material containing a combination of structurally similar analogs of 1,3-dibromoacetone.
专利号:US-4851094-A 优先权日:1985-03-15 标 题:Process for producing amidine sulfonic acid intermediates for guanidines 发明人:MARYANOFF CYNTHIA A; PLAMPIN JAMES N; STANZIONE ROBIN C 权利人:MCNEILAB INC 摘要:An efficient synthesis of quanidines, e.g. of the formula (III), by oxidizing a thiourea, e.g. of the following formula (II): (III) (II) with H2O2 and a molybdenum catalyst to yield an aminoiminomethane sulfonic acid which can then be reacted with an amine followed by optional transamination steps.
摘要:National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review., 5(46), 1953 摘要:Tang, R.-Y., Science of Synthesis: Knowledge Updates, (2024) 1, 356. 摘要:Chesnokova NP, Kuliash GIu. [Possibilities of pharmacologic correction of Na, K-ATPase activity in the spinal cord in botulism]. Biull Eksp Biol Med. 1985 Oct;100(10):442–4. 参考文献:10.1107/s0108270108013504 摘要:Janczak J, Perpétuo GJ. Hydrogen-bonded networks in crystals of 1-(diaminomethylene)thiouron-1-ium perchlorate, hydrogen sulfate, dihydrogen phosphate and dihydrogen arsenate. Acta Crystallogr C Cryst Struct Commun. 2008 May 21;64(6):o330–4. doi: 10.1107/s0108270108013504.