Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB2047/60A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by American Cyanamid CofiledCriticalAmerican Cyanamid Co
Publication of GB887754ApublicationCriticalpatent/GB887754A/en
Organic Low-Molecular-Weight Compounds And Preparation Thereof
(AREA)
Abstract
The invention comprises dedimethylamino-6-demethyl-12a-deoxyanhydro-chlorotetracycline of the formula <FORM:0887754/IV (b)/1> and a process for the preparation of tetracycline amides of the formula R1CONR2R3 where R1 is a tetracycline radical and R2 and R3 are hydrogen atoms or alkyl radicals by reacting an ester of the formula R1COOY with ammonium formate or a formate salt of the formula H.COO(-) (+)NH2R2R3 where Y is an ester-forming organic radical. In the example the novel amide described above is prepared by reacting ethyl 10-benzyloxy-7-chloro-11-methoxy-1, 3, 12 - trioxo - 1, 2, 3, 4, 4a, 5, 12, 12a - octahydro-naphthacene-2-carboxylate with ammonium formate in boiling xylene. An outline synthesis of the ester starting from 2-chloro-5-methoxy-toluene is described.