Erythromycin derivatives

Claim 2

A compond of the general formula IA or IB or a pharmaceutically acceptable ester or acid addition salt thereof: wherein R¹ denotes hydrogen, an unsubstituted or substituted hydrocarbon group, a heterocyclyl group, or an acyl group; R³ denotes hydrogen or hydroxy; R⁶ denotes hydrogen or methyl; one of R⁷ and R⁸ denotes hydrogen, hydroxy, alkoxy, alkanoyloxy, amino, substituted amino, or a group of the formula R⁹-SO₂-O-, and the other or R⁷ and R⁸ denotes hydrogen, or R⁷ and R⁸ together denote an oxo group, an oxime group, or a substituted oxime group; and R⁹ denotes an organic group.

Claim 3

A compound as claimed in claim 1, wherein R¹ denotes an unsubstituted or a substituted alkyl, alkylene, cycloalkyl or aryl group.

Claim 4

A compound as claimed in claim 1, wherein R¹ denotes an unsubstituted or a substituted (C₁₋₆) alkyl, (C₁₋₆) alkylene, cyclohexyl, phenyl, furyl, thienyl, pyridyl, triazolyl or (C₁₋₆) alkanoyl group.

Claim 5

A compound as claimed in any one of claims 1 to 3, wherein R³ denotes a hydroxyl group and R⁶ denotes a methyl group.

Claim 6

A compound selected from the group consisting of: (i) 9,11- N , O -benzylideneerythromycin A 9-imine (ii) 9,11- N , O -methyleneerythromycin A 9-imine (iii) 9,11- N , O -ethylideneerythromycin A 9-imine (iv) 9,11- N , O -(2-thienylmethylene)erythromycin A 9-imine (v) 9,11, N - O -cyclohexylmethyleneerythromycin A 9-imine (vi) 9,11- N , O -propylideneerythromycin A 9-imine (vii) 9,11- N , O - p -methylbenzylideneerythromycin A 9-imine (viii) 9,11- N , O -furfurylideneerythromycin A 9-imine (ix) 9,11- N , O - p -chlorobenzylideneerythromycin A 9-imine (x) 9,11- N , O -(2-oxapropylidene)erythromycin A 9-imine (xi) 9,11- N , O -(3-ethoxypropylidene)erythromycin A 9-imine (xii) 9,11- N , O - p -nitrobenzylideneerythromycin A 9-imine (xiii) 9,11- N , O - p -methoxybenzylideneerythromycin A 9-imine (xiv) 9,11-N, O -butylideneerythromycin A 9-imine (xv) 9,11-N, O -pentylideneerythromycin A 9-imine (xvi) 9,11-N, O -(2,2,2-trimethylethylidene)­erythromycin A 9-imine (xvii) 9,11-N, O -(2-phenylethylidene)erthyromycin A 9-imine (xviii) 9,11-N, O - p -fluorobenzylideneerthyromycin A 9-imine (xix) 9,11-N, O - p -acetamidobenzylidene A erythromycin-9-imine (xx) 9,11-N, O -(3-phenylprop-2-enylidene)­erythromycin A 9-imine (xxi) 9,11-N, O -(pyridine-4-yl)methyleneerythromycin A 9-imine (xxii) 9,11-N, O -(1-methyl-1,2,3-triazol-4-yl)­methyleneerythromycin A 9-imine (xxiii) 9,11-N, O -(2-hydroxyethylidene)erythromycin A 9-imine (xxiv) 9,11-N, O -(2-azidoethylidene)erythromycin A 9-imine (xxv) 9,11-N, O -(2-aminoethylidene)erythromycin A 9-imine as well as the corresponding isomers in the form of formula IB, as given in claim 1, and pharmaceutically acceptable esters and acid addition salts of such compounds.

Claim 7

A process for the preparation of a compound of the general formula IA or IB as given in claim 1, or a pharmaceutically acceptable ester or acid addition salt thereof, which comprises reacting a compound of the general formula IIIA or IIIB: wherein R³, R⁶, R⁷ and R⁸ are defined as in claim 1 and, in which compound of the general formula IIIA or IIIB, any reactive group (other than the 9-imino and 11-hydroxy groups) may optionally be protected, with a compound of the general formula IV, VI or VII: wherein R¹ is defined as in claim 1 and each of R¹¹ and R¹², which may be identical or different, denotes a hydrocarbon group, and thereafter removing any protecting group that may be present; and optionally (a) converting either or both of groups R⁷ and R⁸ to another such group; and/or (b) forming a pharmaceutically acceptable ester or acid addition salt.

Claim 8

A compound of the general formula VA or VB wherein R³ and R⁶ are defined as in claim 1; one of R 7A and R 8A denotes H, OH, OZ, NZ₂, NH₂, NHZ, substituted NH₂, substituted NHZ, alkanoyloxy, or R⁹-SO₂-O- (in which R⁹ denotes an organic group), and the other of R 7A and R 8A denotes H, or R 7A and R 8A together denote oxo; R¹⁰ denotes H or Z; and Z denotes a protecting group,

Claim 9

A pharmaceutical composition which comprises a compound as claimed in any one of claims 1 to 5 together with a pharmaceutically acceptable carrier or excpient.

Claim 10

A compound as claimed in any one of claims 1 to 5 or a composition as claimed in claim 8 for use in the treatment of bacterial infection.

Claim 11

The use of a compound as claimed in any one of claims 1 to 5 for the manufacture of a medicament.