YU46777B

YU46777B - PROCEDURE FOR OBTAINING NEW MACROLIDE COMPOUNDS

Info

Publication number: YU46777B
Application number: YU218687A
Authority: YU
Inventors: D.R. Sutherland; O.Z. Pereira; H.M. Noble; M.V.J. Ramsay; J.B. Ward; R.A. Fletton; E.P. Tiley; N. Porter; D. Noble
Original assignee: American Cynamid Co.
Priority date: 1987-04-08
Filing date: 1987-12-04
Publication date: 1994-05-10
Also published as: YU148788A; HRP920589B1; YU46713B; YU46714B; YU106689A; YU46712B; YU47126B; GB8708423D0; SI8712186A; YU148988A; YU148888A; YU218687A; HRP920589A2

Abstract

POSTUPAK ZA DOBIJANJE NOVIH MAKROLIDNIH JEDINJENJA, opšte formule u kojoj: R1 pretstavlja metil, etil ili izopropil grupu; R2 vodonikov atom, C1-4alkil grupu ili alil grupu i grupa = NOR2 je u E-konfiguraciji; i OR3 je hidroksilna grupa ili - OR4, - OCOR4 ili - OCOOR4, gde je R4 C1-4alkil ili -OCOR8R9, gde su R8 i R9 nezavisno vodonik ili C1-4 alkil, naznačen time, što obuhvata reakciju jedinjenja formule sa reagensom formule H2NOR2, pri čemu u formulama R1R2 i OR3 imaju ista značenja kao što su definisana ranije, pri čemu se reakcija oksidacije vrši u vodenim ili nevodenim reakcionim sredinama i na temperaturi u intervalu od -20 do +100В°C, najpoželjnije -10 do 50В°C, posle čega se, po potrebi, za pravljenje jedinjenja formule (I) u kojoj je R2 C1-4 alkil ili alil grupa i OR3 supstituisana hidroksilna grupa, vrši reakcija jedinjenja formule (I) u kojoj je OR3 hidroksilna grupa sa reagensom za konverziju hidroksilne grupe u supstituisanu hidroksilnu grupu, ili se za pravljenje jedinjenja formule (I) u kojoj je R2 C1-4 alkil ili alil, vrši reakcija jedinjenja formule (I) u kojoj je R2 atom vodonika i OR3 supstituisana hidroksilna grupa, sa sredstvom za eterifikaciju formule R2Y u kojoj je R2 C1-4 alkil ili alil a Y je odlazeća grupa i onda se, ako je potrebno, uklanja zaštitna grupa sa OR3 zaštićene hidroksilne grupe u jedinjenju formule (I). Prijava sadrži još 3 zavisna zahteva.A process for the preparation of novel macrolide compounds of the general formula in which: R 1 represents a methyl, ethyl or isopropyl group; R2 is a hydrogen atom, a C1-4alkyl group or an allyl group and the group = NOR2 is in the E-configuration; and OR3 is a hydroxyl group or - OR4, - OCOR4 or - OCOOR4, wherein R4 is C1-4alkyl or -OCOR8R9, wherein R8 and R9 are independently hydrogen or C1-4 alkyl, comprising reacting a compound of formula with a reagent of formula H2NOR2 , wherein in formulas R1R2 and OR3 have the same meanings as previously defined, wherein the oxidation reaction is carried out in aqueous or non-aqueous reaction media and at a temperature in the range from -20 to + 100V ° C, most preferably -10 to 50V ° C , after which, if necessary, to prepare a compound of formula (I) in which R 2 is a C 1-4 alkyl or allyl group and an OR 3 substituted hydroxyl group, a reaction of a compound of formula (I) in which OR 3 is a hydroxyl group with a hydroxyl conversion reagent groups to a substituted hydroxyl group, or to form a compound of formula (I) in which R 2 is C 1-4 alkyl or allyl, a reaction of a compound of formula (I) in which R 2 is a hydrogen atom and OR 3 is a substituted hydroxyl group, with an esterifying agent of formula R2Y wherein R 2 is C 1-4 alkyl or allyl and Y is a leaving group and then, if necessary, the protecting group is removed from the OR 3 protected hydroxyl group in the compound of formula (I). The application contains 3 more dependent requests.