Patent GB-1118306-A (GB)
Title: Improvements in or relating to lincomycin derivatives and the manufacture thereof
IPC: C08G73/10
Filed: 1965-07-14
Abstract: The invention comprises a compound having the general formula <FORM:1118306/C2/1> wherein R is an alkylidene group of not more than 20 carbon atoms, cycloalkylidene of 3 to not more than 8 carbon atoms, or aralkylidene of not more than 12 carbon atoms, R2 and R3 are hydrogen or alkyl of not more than 12 carbon atoms, and Z is a protective hydrocarbyl-oxycarbonyl group removable by hydrogenolysis or trityl (triphenylmethyl), diphenyl-(p-methoxyphenyl) methyl, bis - (p - methoxyphenyl) phenylmethyl, benzyl, or p-nitrobenzyl and W is H, -S-alkyl of not more than 12 carbon atoms or -SCH2CH2OR4, wherein R4 is alkyl of not more than 12 carbon atoms, a compound having the gzneral formula <FORM:1118306/C2/2> wherein R, R2, R3 and W are as defined above, T is H or Z as defined above, and the acid addition salt form of these compounds wherein T represents hydrogen provided that when T, R2 and R3 represent hydrogen and W represents -S-alkyl in the b -position, RH does not represent trans-propyl, the free base and acid-addition salt forms of a compound of the formula <FORM:1118306/C2/3> wherein R, R2 and R3 are as defined above, R1 is alkyl of not more than 20 carbon atoms, cycloalkyl of not more than 8 carbon atoms, or aralkyl of not more than 12 carbon atoms, and alkyl is of not more than 12 carbon atoms, the free base and acid addition salt forms of a compound of the formula <FORM:1118306/C2/4> wherein R, R1, R2 and R3 are as defined above and V is H or -SCH2CH2OR4, wherein R4 is as defined above, the free base and acid addition salt forms of the formula <FORM:1118306/C2/5> wherein R, R1, R2, R3 and alkyl are as defined above, a compound of the formula <FORM:1118306/C2/6> wherein R, R2, R3, Y and Z are as defined above, a compound of the formula <FORM:1118306/C2/7> wherein R, R2, R3 and Y are as defined above, M is H or Z as defined above, or alkyl of not more than 20 carbon atoms, cycloalkyl of not more than 8 carbon atoms or aralkyl of not more than 12 carbon atoms and acid addition salt forms of the compounds wherein M is hydrogen or alkyl of not more than 20 carbon atoms, cycloalkyl of not more than 8 carbon atoms or aralkyl of not more than 12 carbon atoms, a compound of the formula <FORM:1118306/C2/8> wherein Ac is acyl of the formula <FORM:1118306/C2/9> wherein R, R1, R3 and Y are as defined above, the free base and acid addition salt forms of a compound of the formula <FORM:1118306/C2/100> and a process which comprises reacting a compound of the formula <FORM:1118306/C2/111> wherein Z is as defined above with a Wittig reagent of the formula R = P(C6H5)3 wherein R is as defined above, to form a compound of the formula <FORM:1118306/C2/122> hydrogenating this compound over a platinum catalyst to form a compound of the formula <FORM:1118306/C2/133> and with this compound N-acylating a compound of the formula <FORM:1118306/C2/144> wherein R, R3, R4 and Y are as defined above, to form a compound of the formula <FORM:1118306/C2/155> hydrogenating this compound over a palladium catalyst to remove the Z group and alkylating the thus obtained compound to give a compound of the formula <FORM:1118306/C2/166> wherein R, R2, R3, Y and R1 are as define above.  Antibacterial compositions comprise the above compounds as the active ingredient together with a pharmaceutically acceptable carrier.