Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1994-06-21
1997-05-20
Peselev, Elli
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 72, C07H 1708
Patent
active
056313543
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to novel derivatives of an antibiotic erythromycin. More particularly, it relates to novel derivatives of 5-O-desosaminylerythronolide derivatives and pharmaceutically acceptable acid addition salts thereof.
BACKGROUND ART
Erythromycin is an antibiotic clinically widely used as an agent for curing infectious diseases caused by Gram-positive bacteria, some Gram-negative bacteria, mycoplasmas, etc. Many derivatives of erythromycin have been produced for improving the biological and/or pharmacodynamic characteristics of erythromycin. As 5-O-desosaminylerythronolide derivatives, 3-O-acyl-5-O-desosaminylerythronolide derivatives, for example, have been disclosed in U.S. Pat. No. 3,923,784. 5-O-desosaminylerythronolide derivatives, however, have been generally considered to be poor in antibacterial activity, and the antibacterial activity of the above-exemplified derivatives is also very weak. An object of the present invention is to provide novel antibiotics having a strong antibacterial activity.
DISCLOSURE OF THE INVENTION
The present inventors conducted various researches on the antibacterial activity of 5-O-desosaminylerythronolide derivatives and consequently found that compounds obtained by introducing a certain substituted carbonyloxy group into 5-O-desosaminylerythronolide derivatives at the 3-position have a very strong antibacterial activity unexpectedly, whereby the present invention has been accomplished.
The present invention is 5-O-desosaminylerythronolide derivatives represented by the formula: ##STR2## [wherein Y is a group represented by the formula: ##STR3## (wherein R.sup.1 is a hydrogen atom, a hydroxyl group, a halogen atom, a C.sub.1 -C.sub.3 alkyl group, a C.sub.1 -C.sub.10 alkylamino group, a C.sub.7 -C.sub.15 aralkylamino group, an amino group, a C.sub.2 -C.sub.10 acylamino group, or a C.sub.2 -C.sub.10 acylamino group containing at least one nitrogen atom or oxygen atom, and n is an integer of 0 to 4), an oxygen atom, a vinylene group, or a group represented by the formula --CH.sub.2 --NH--CO--, R is a hydrogen atom; a C.sub.1 -C.sub.5 alkyl group; a C.sub.1 -C.sub.5 alkyl group containing at least one nitrogen atom, oxygen atom or sulfur atom; a C.sub.7 -C.sub.15 aralkyl group; a C.sub.7 -C.sub.15 aralkyl group containing at least one nitrogen atom, oxygen atom or sulfur atom; a phenyl group; a substituted phenyl group having 1 to 5 substituents selected from halogen atoms, nitro groups, amino groups, C.sub.1 -C.sub.3 alkyl groups, substituted C.sub.1 -C.sub.3 alkyl groups having one or more halogen atoms as the substituent(s), C.sub.1 -C.sub.4 alkylamino groups, C.sub.2 -C.sub.7 acylamino groups and C.sub.1 -C.sub.4 alkoxy groups; a naphthyl group; a thiazolyl group; an imidazolyl group; an aminothiazolyl group; a biphenyl group; a thienyl group; a pyridyl group; a substituted pyridyl group having one or more nitro groups as the substituent(s); a phenylthio group; a substituted phenyloxy group having one or more halogen atoms or nitro groups as the substituent(s); or an indolyl group (but in the case of Y being an oxygen atom, R is not a hydrogen atom), A is a group represented by the formula (i): ##STR4## (wherein Z is an oxygen atom or a group represented by the formula .dbd.N--O--R.sup.4 (wherein R.sup.4 is a hydrogen atom; a C.sub.1 -C.sub.8 alkyl group; a C.sub.2 -C.sub.18 alkyl group containing at least one nitrogen atom, oxygen atom or sulfur atom; a benzyl group; or a substituted benzyl group having 1 to 5 substituents selected from halogen atoms and C.sub.1 -C.sub.4 alkyl groups), V is a hydroxyl group and W is a hydrogen atom or a hydroxyl group, or V and W represent together with the carbon atoms at the 11- and 12-positions a group represented by the formula: ##STR5## or a group represented by the formula: ##STR6## (wherein R.sup.5 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group), a group represented by the formula (ii): ##STR7## (wherein R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group), or a group repr
REFERENCES:
patent: 3923784 (1975-12-01), Kierstead et al.
patent: 4518590 (1985-05-01), Hauske et al.
patent: 4742049 (1988-05-01), Baker et al.
patent: 4921839 (1990-05-01), Brain et al.
Journal of Medicinal Chemistry, 1975, vol. 18 No. 8, pp. 849-851.
Asaka Toshifumi
Hatayama Katsuo
Kashimura Masato
Misawa Yoko
Morimoto Shigeo
Peselev Elli
Taisho Pharmaceutical Co. Ltd.
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