Method for producing diphenyl azetidinone derivatives

Details Method for producing diphenyl azetidinone derivatives Method for producing diphenyl azetidinone derivatives

C - Chemistry, Metallurgy

07

D

C07D 205/08 (2006.01) C07C 233/20 (2006.01) C07C 235/34 (2006.01) C07C 237/20 (2006.01) C07F 7/02 (2006.01)

Patent

CA 2567481

The invention relates to a method for producing diphenyl azetidinone derivatives of general formula (I) or forms protected in the substituents X, R1 and/or R2, wherein the symbols, substituents, and indices have the following designations: X = H, OH; Rl = OH, OCH3; R2 = F, CH2CH3, CH2NHR4; R3 = H, F; R4 = H, CO-(CH2-)nCO-R5, CO-(CH2-)nNHR6; n = whole numbers from 4 to 16; R5 = OH, NH-CH2-[CH(OH)-]mCH2OH; R6 = H, CO-[CH(OH)-]mCH2OH; and m = whole numbers from 1 to 5. According to said method, novel compounds of general formula (II), wherein Y = H, H; H, OH; H, OAc; H, OSi(alkyl)o(aryl)p where o, p = 0, 1, 2 or 3 and o + p = 3; H, OTHP; H, OC(Aryl)3; H, OCH2OAlkyl; H, OCH(OAlkyl)CH3; H, OAlkyl; H, OCH2aryl; Oalkyl, Oalkyl; and cyclic ketone acetyl such as O-(CH2-)q-O where q = 2 or 3, are reacted with imines of general formula (III) wherein R7 = R1 and O protective groups and R8 = e.g. R2.

L'invention concerne un procédé de production de dérivés de diphénylazétidinone de formule générale (I) ou des formes, dans lesquelles les substituants X, R?1¿ et/ou R?2¿ sont protégés, formule dans laquelle les symboles, les substituants et les indices ont la signification suivante : X = H, OH ; R?1¿ = OH, OCH¿3? ; R?2¿ = F, CH¿2?CH¿3?, CH¿2?NHR?4¿ ; R?3¿ = H, F ; R?4¿ = H, CO-(CH¿2?-)¿n?CO-R?5¿, CO-(CH¿2?-)¿n?NHR?6¿ ; n = un nombre entier de 4 à 16 ; R?5¿ = OH, NH-CH¿2?-[CH(OH)-]¿m?CH¿2?OH ; R?6¿ = H, CO-[CH(OH)-]¿m?CH¿2?OH et m = un nombre entier de 1 à 5. Ledit procédé consiste à faire réagir de nouveaux composés de formule générale (II), dans laquelle Y = H, H ; H, OH ; H, OAc ; H, OSi(alkyle)¿o?(aryle)¿p? ; o, p = 0, 1, 2 ou 3 et o + p = 3 ; H, OTHP ; H, OC(aryle)¿3? ; H, OCH¿2?Oalkyle ; H, OCH(Oalkyle)CH¿3? ; H, Oalkyle ; H, OCH¿2?aryle ; OAlkyle, OAlkyle ; un cétal cyclique tel que O-(CH¿2?-)¿q?-O et q = 2 ou 3, avec des imines de formule générale (III), dans laquelle R?7¿ = R?1¿ et un groupe protecteur O et R?8¿ = p. ex. R?2¿.

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