Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Carbohydrate doai
Patent
1999-08-05
2000-12-26
Peselev, Elli
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Carbohydrate doai
536 74, A61K 3170
Patent
active
06165986&
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to antibiotic erythromycin A derivatives.
BACKGROUND ART
Erythromycin A is an antibiotic clinically widely used as an agent for treating infectious diseases caused by Gram-positive bacteria, mycoplasmas, etc. However, erythromycin A is decomposed by the gastric acid due to instability to acids, and thereby has a drawback of no constancy of movement in the body. Hitherto many erythromycin A derivatives have been prepared for the purpose of the improvement of the biological or pharmacological properties. For example, it is reported that 6-O-methylerythromycin A derivatives have an improved stability to acids and have a superior in vivo antibacterial activity in comparison with erythromycin A when administered orally (U.S. Pat. No. 4,331,803). Recently, it is also reported that 11,12-cyclic carbamate derivatives are prepared with the aim of expansion of antibacterial spectrum as well as stability to acids (EP. patent. No. 487411, U.S. Pat. No. 4,742,049, EP. Patent No. 676409 and ibid. 638584).
An object of the present invention is to provide a novel antibiotic erythromycin A derivative or a salt thereof having a strong antibacterial activity against not only known erythromycin-sensitive bacteria but also Haemophilus influenzae and erythromycin-resistant bacteria which recently are showing a tendency to increase, and a composition comprising the same as an effective component. Other objects of the present invention are to provide a method for the treatment of a bacterially infectious disease which comprises administering a pharmaceutically effective amount of the above-mentioned erythromycin A derivative or salt thereof to a patient, and use of the above-mentioned erythromycin A derivative or salt thereof for the treatment of a bacterially infectious disease.
The present inventors have variously researched on erythromycin A derivatives, in particular, their 11,12-cyclic carbamate compounds which have a certain substituted amino group on the nitrogen atom of the carbamate group at the 11-position, a methoxy group at the 6-position and a carbonyl group at the 3-position. As a result, compounds having the benzyl group substituted by an alkyl group, an alkoxy group (particularly, a methoxy group) or an amino group on the benzene ring have been found to have a stronger antibacterial activity against erythromycin-resistant bacteria than the compounds of which substituent on the nitrogen atom forming the carbamate group at the 11-position is a 2-(N-benzyl-N-methylamino)ethyl group (EP Patent No. 487411), and compounds having a pyridylmethyl group or a quinolylmethyl group other than the benzyl group have also been found to similarly have a strong activity. The present invention has been accomplished on the basis of the finds.
The present invention relates to an erythromycin A derivative represented by Formula (I): ##STR2## (wherein n is an integer of 2 to 4, R.sup.1 is a pyridylmethyl group, a furylmethyl group, a thienylmethyl group, a quinolylmethyl group or a benzyl group having 1 to 3 substituents selected from the group consisting of an alkyl group having 1 to 5 carbon atoms, a nitro group, an alkoxy group having 1 to 5 carbon atoms, an amino group and an amino group substituted by 1 or 2 alkyl groups having 1 to 5 carbon atoms, R.sup.2 is the same group as defined for R.sup.1, a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an acetyl group or a pyridylacetyl group, and R.sup.3 is an alkyl group having 1 to 5 carbon atoms or a cinnamyl group) or a pharmaceutically acceptable salt thereof.
In the above-mentioned formula, n is preferably 2 or 3. The alkyl group having 1 to 5 carbon atoms in the definition for R.sup.1 refers to a straight or branched alkyl group, and is preferably a methyl group. The alkoxy group having 1 to 5 carbon atoms refers to a straight or branched alkoxy group, and is preferably a methoxy group, and the amino group substituted by 1 or 2 alkyl groups having 1 to 5 carbon atoms is preferably a dimethylamino group. The alkyl group
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Asaka Toshifumi
Ishii Takaaki
Kashimura Masato
Matsuura Akiko
Sugimoto Tomohiro
Peselev Elli
Taisho Pharmaceutical Co. Ltd.
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