US 5,631,354 AGranted

5-O-desosaminylerythronolide derivatives

AssigneeTaisho Pharmaceutical Co., Ltd.

InventorsToshifumi Asaka, Yoko Misawa, Masato Kashimura, Shigeo Morimoto, Katsuo Hatayama

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Abstract

Object: Provision of novel macrolide antibiotics having a strong antibacterial activity. Construction: Compounds represented by the formula: ##STR1## which are obtained by introducing a certain substituted carbonyloxy group into 5-O-desosaminylerythronolide derivatives at the 3-position; and pharmaceutically acceptable acid addition salts thereof.

Claims13

Dependent claims

A 5-0-desosaminylerythronolide derivative represented by the formula:

##STR37## wherein:
Y is a group represented by the formula:
##STR38## (wherein R.sup.1 is a hydrogen atom, a hydroxyl group, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or an amino group, 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 C.sub.7 -C.sub.15 aralkyl group;
a C.sub.7 -C.sub.15 aralkyl group substituted by at least one member selected from the group consisting of a nitro group, a methoxy group, a methoxythio group, a methoxycarbonyl group, a carboxy group, a methylene group, a halogen atom, a trifluoromethyl group, an amino group and a demethylamino group;
a phenyl group;
a phenyl group having 1 to 5 substituents selected from the group consisting of halogen atoms, nitro groups, amino groups, C.sub.1 -C.sub.3 alkyl groups, C.sub.1 -C.sub.3 alkyl groups substituted by one or more halogen atoms, 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 amino-thiazolyl group;
a biphenyl group;
a thienyl group;
a pyridyl group;
a pyridyl group substituted by one or more nitro groups;
a phenylthio group;
a phenyloxy group substituted by one or more halogen atoms or nitro groups;
or an indolyl group,
A is a group represented by:
the formula (i):
##STR39## 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;
--CH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 SCH.sub.3 ;
--CH.sub.2 CH.sub.2 (NH)CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 ;
--CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 ;
--CH.sub.2 CH.sub.2 N(CH.sub.2)(CH.sub.2 Ph;
a benzyl group;
or a benzyl group having 1 to 5 substituents selected from the group consisting of 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:
##STR40## a group represented by the formula:
##STR41## (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):
##STR42## (wherein R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group), or a group represented by the formula (iii):
##STR43## (wherein R.sup.7 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or C.sub.3 -C.sub.5 alkynyl group, and V and W are as defined above),
R' is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, a carbamoyl group or an acetyl group,
R" is a hydrogen atom, a C.sub.2 -C.sub.15 alkoxycarbonyl group, 2-[2-(2-methoxyethyoxy) ethoxy]ethoxycarbonyl group, 2-[2-(2-ethoxyethoxy)ethoxy]ethoxycarbonyl group, a C.sub.2 -C.sub.15 acyl group, an ethylsuccinyl group, or a pyridylcarbonyl group or
a pharmaceutically acceptable acid addition salt thereof.

37 more elements

Dependencies are inferred from the claim text.

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Abstract

A 5-0-desosaminylerythronolide derivative represented by the formula:

##STR37## wherein:
Y is a group represented by the formula:
##STR38## (wherein R.sup.1 is a hydrogen atom, a hydroxyl group, a halogen atom, a C.sub.1 -C.sub.3 alkyl group or an amino group, 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 C.sub.7 -C.sub.15 aralkyl group;
a C.sub.7 -C.sub.15 aralkyl group substituted by at least one member selected from the group consisting of a nitro group, a methoxy group, a methoxythio group, a methoxycarbonyl group, a carboxy group, a methylene group, a halogen atom, a trifluoromethyl group, an amino group and a demethylamino group;
a phenyl group;
a phenyl group having 1 to 5 substituents selected from the group consisting of halogen atoms, nitro groups, amino groups, C.sub.1 -C.sub.3 alkyl groups, C.sub.1 -C.sub.3 alkyl groups substituted by one or more halogen atoms, 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 amino-thiazolyl group;
a biphenyl group;
a thienyl group;
a pyridyl group;
a pyridyl group substituted by one or more nitro groups;
a phenylthio group;
a phenyloxy group substituted by one or more halogen atoms or nitro groups;
or an indolyl group,
A is a group represented by:
the formula (i):
##STR39## 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;
--CH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 SCH.sub.3 ;
--CH.sub.2 CH.sub.2 (NH)CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 ;
--CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.3 ;
--CH.sub.2 CH.sub.2 N(CH.sub.3).sub.2 ;
--CH.sub.2 CH.sub.2 N(CH.sub.2)(CH.sub.2 Ph;
a benzyl group;
or a benzyl group having 1 to 5 substituents selected from the group consisting of 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:
##STR40## a group represented by the formula:
##STR41## (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):
##STR42## (wherein R.sup.6 is a hydrogen atom or a C.sub.1 -C.sub.3 alkyl group), or a group represented by the formula (iii):
##STR43## (wherein R.sup.7 is a hydrogen atom, a C.sub.1 -C.sub.4 alkyl group, a C.sub.3 -C.sub.5 alkenyl group or C.sub.3 -C.sub.5 alkynyl group, and V and W are as defined above),
R' is a hydrogen atom, a C.sub.1 -C.sub.5 alkyl group, a carbamoyl group or an acetyl group,
R" is a hydrogen atom, a C.sub.2 -C.sub.15 alkoxycarbonyl group, 2-[2-(2-methoxyethyoxy) ethoxy]ethoxycarbonyl group, 2-[2-(2-ethoxyethoxy)ethoxy]ethoxycarbonyl group, a C.sub.2 -C.sub.15 acyl group, an ethylsuccinyl group, or a pyridylcarbonyl group or
a pharmaceutically acceptable acid addition salt thereof.

37 more elements