The patent badge is an abbreviated version of the USPTO patent document. The patent badge does contain a link to the full patent document.
The patent badge is an abbreviated version of the USPTO patent document. The patent badge covers the following: Patent number, Date patent was issued, Date patent was filed, Title of the patent, Applicant, Inventor, Assignee, Attorney firm, Primary examiner, Assistant examiner, CPCs, and Abstract. The patent badge does contain a link to the full patent document (in Adobe Acrobat format, aka pdf). To download or print any patent click here.
Patent No.:
Date of Patent:
Jun. 01, 1976
Filed:
Sep. 06, 1974
Peter W Woo, Ann Arbor, MI (US);
Parke, Davis & Company, Detroit, MI (US);
Abstract
O-2,6-Diamino-2,3,4,6-tetradeoxy-.alpha.-D-erythro-hexopyranosyl-(1.fwdarw. 4)-O-[5-amino-5-deoxy-.beta.-D-xylofuranosyl-(1.fwdarw.5)]-N.sup.1 -[(S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxystreptamine, also known as aminotrideoxybutirosin A, and acid-addition salts. They have a wide spectrum of antibacterial activity. The above compounds can be produced from aminodeoxybutirosin A by the sequence of reactions which comprises protecting the five primary amino groups by converting them to arylmethoxycarbonyl derivatives, converting the 3',4'-hydroxyl groups to an acetal, acylating the remaining four hydroxyl groups, and hydrolyzing the acetal to produce a key intermediate which is an O-2,6-dideoxy-2,6-bis[[(arylmethoxy)carbonyl]amino]-.alpha.-D-glucopyranos yl-(1.fwdarw.4)-O-[2,3-di-O-acyl-5-deoxy-5-[[(arylmethoxy)carbonyl]amino]-. beta.-D-xylofuranosyl-(1.fwdarw.5)]-6-O-acyl-N.sup.1 -[(S)-2-acyloxy-1-oxo-4-[[(arylmethoxy)carbonyl]amino]-butyl]-2-deoxy-N.su p.3 -[(arylmethoxy)carbonyl]streptamine, generically also identified as protected 5'-aminodeoxybutirosin A. That compound is reacted with methanesulfonyl chloride in pyridine to introduce 3',4'-methanesulfonyloxy groups which are removed by reaction with zinc and sodium iodide to introduce a double bond at the 3',4' position. The acyl groups are hydrolyzed or cleaved as by reaction with ammonia in methanol and the product is reacted with hydrogen in the presence of a catalyst to remove the arylmethoxycarbonyl groups and hydrogenate the double bond with the formation of aminotrideoxybutirosin A.