Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1995-07-13
1997-02-11
Peselev, Elli
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 71, 536 72, 536 73, C07H 1708
Patent
active
056022395
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel derivatives of an antibacterial erythromycin, and more particularly relates to novel derivatives of 5-O-desosaminylerythronolide and pharmaceutically acceptable acid addition salts thereof.
BACKGROUND OF ART
Erythromycins are antibiotics clinically widely used as agents for treating infectious diseases caused by Gram-positive bacteria, some Gram-negative bacteria, mycoplasmas, etc. Many erythromycin derivatives have been prepared for the improvement of biological and/or pharmacological properties of erythromycins. Examples of prior art 5-O-desosaminylerythronolide derivative are 3-O-acyl-5-O-desosaminylerythronolide derivatives described in U.S. Pat. No. 3,923,784. However, prior art 5-O-desosaminylerythronolide derivatives are generally considered as inferior in the antibacterial properties, and actually, the above-mentioned derivatives have extremely weak antibacterial activity. An object of the present invention is to provide novel antibiotics having a strong antibacterial activity.
DISCLOSURE OF THE INVENTION
As a result of various researches on the antibacterial activity of novel 5-O-desosaminylerythronolide derivatives, the present inventors have found that the compounds wherein a specific aryloxy group or an alkoxy group is introduced at the 3-position of 5-O-desosaminylerythronolide derivatives have unexpectedly an extremely strong antibacterial activity, and the present invention has been accomplished.
The present invention relates to a 5-O-desosaminylerythronolide derivative represented by the formula: ##STR2## [wherein A is a group represented by the formula: ##STR3## (wherein V is a hydroxyl group, W is a hydrogen atom or a hydroxyl group, or V and W together with the carbon atoms at the 11- and 12-positions form a cyclic carbonate group) or a group represented by the formula: ##STR4## (wherein W' is a hydrogen atom or a hydroxyl group), B is a hydroxyl group or a methoxy group, U is a hydrogen atom or a C.sub.2 -C.sub.8 alkanoyl group, Y is a C.sub.4 -C.sub.6 cyclic alkyl group containing an oxygen atom, a phenyl group, a phenyl group substituted by one to 5 members selected from the group consisting of halogen atoms, nitro groups, trifluoromethyl groups and amino groups, a glucopyranosyl group, a ribopyranosyl group, a glucopyranosyl group substituted by an acetyl group or a benzyl group on the hydroxyl group, a ribopyranosyl group substituted by an acetyl group or a benzyl group on the hydroxyl group, a benzyl group, a benzyl group substituted by a C.sub.1 -C.sub.3 alkyl group; or methyl group, Z is an oxygen atom or a group represented by the formula: .dbd.N-O-R.sup.1 (wherein R.sup.1 is a hydrogen atom, a C.sub.2 -C.sub.8 alkanoyl group, a benzyl group or a benzyl group substituted by one to 5 members selected from the group consisting of halogen atoms and C.sub.1 -C.sub.4 alkyl groups)] or a pharmaceutically acceptable acid addition salt thereof.
In the present invention, the alkanoyl group refers to, for example, an acetyl group, a propionyl group or benzoyl group. The cyclic alkyl group containing an oxygen atom refers to, for example, a tetrahydropyranyl group or a tetrahydrofuranyl group. The halogen atom refers to a fluorine atom, a chlorine atom, a bromine atom or an iodine atom. The alkyl group refers to a straight or branched chain alkyl group. The pharmaceutically acceptable acid addition salt refers to, for example, acetate, propionate, butyrate, formate, trifluoroacetate, maleate, tartrate, citrate, stearate, succinate, ethylsuccinate, lactobionate, gluconate, glucoheptonate, benzoate, methanesulfonate, ethanesulfonate, 2-hydroxyethanesulfonate, benzenesulfonate, p-toluenesulfonate, laurylsulfate, malate, aspartate, glutaminate, adipate, cysteine salt, hydrochloride, hydrobromide, phosphate, sulfate, hydroiodide, nicotinate, oxalate, picrate, thiocyanate, undecanoate, polyacrylate or carboxyvinyl polymer salt.
The compounds of the invention are those in which the configurations at the 3-position include both of a nat
REFERENCES:
patent: 3923784 (1975-12-01), Kierstead et al.
patent: 5444051 (1995-08-01), Agouridar et al.
Asaka Toshifumi
Hatayama Katsuo
Kashimura Masato
Misawa Yoko
Morimoto Shigeo
Peselev Elli
Taisho Pharmaceutical Co. Ltd.
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