Phosphonic ester derivatives of quinazolinones

Details Phosphonic ester derivatives of quinazolinones Phosphonic ester derivatives of quinazolinones

1996-09-05

1998-08-25

Shah, Mukund J.

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Phosphorus containing other than solely as part of an...

544243, 544244, A61K 31675, C07F 96512

Patent

active

057983445

DESCRIPTION:

BRIEF SUMMARY
TECHNICAL FIELD

This application is a 371 of PCT/JP95/00303, F.D. Feb. 27, 1995.
The present invention relates to novel phosphonic ester derivatives.


PRIOR ART

The phosphonic ester derivatives of the invention are novel compounds not heretofore described in the literature.
The object of the invention is to provide compounds of value as medicines as will be described hereinafter.


DISCLOSURE OF THE INVENTION

The present invention provides a phosphonic ester derivative of the following formula (1): ##STR2## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.6 are the same or different and each represents a hydrogen atom, a lower alkyl group, a halogen atom, a nitro group, a lower alkoxy group, a cyano group, a phenylsulfonylamino group, a benzoylamino group, an amino group or a halogen-substituted lower alkyl group, R.sup.4 represents a phenyl group, a lower alkyl group, a phenyl(lower)alkyl group optionally substituted by halogen on the phenyl ring, a lower alkenyl group, a carboxy(lower)alkyl group, a (lower)alkoxycarbonyl(lower)alkyl group, a (lower)alkoxy(lower)alkyl group, a lower alkynyl group, a benzoyl(lower)alkyl group, an amino group, a di(lower)alkanoylamino group, a benzylideneamino group optionally having lower alkoxy on the phenyl ring or a pyridylmethylideneamino group, R.sup.5 represents a lower alkyl group, R.sup.7 represents a lower alkoxy group, a hydroxyl group, a phenyl group, a phenyl(lower)alkoxy group optionally having halogen on the phenyl ring or a phenyl(lower)alkylamino group, X.sup.1 and X.sup.2 independently represent an oxygen atom or a sulfur atom, A represents an oxygen atom or a single bond, and Z represents a lower alkylene group.
Each of the groups relevant to the above formula (1) includes the following exemplary species.
The halogen atom includes fluorine, chlorine, bromine and iodine.
The lower alkoxy group includes methoxy, ethoxy, propoxy, isopropoxy, butoxy, tert-butoxy, pentyloxy, hexyloxy and so on.
The lower alkyl group includes methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl and so on.
The phenyl(lower)alkyl group optionally substituted by halogen on the phenyl ring includes benzyl, .alpha.-phenethyl, .beta.-phenethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl, 4-phenylbutyl, 5-phenylpentyl, 6-phenylhexyl, 2-bromobenzyl, 3-bromobenzyl, 4-bromobenzyl, 4-chlorobenzyl, 4-fluorobenzyl, 4-iodobenzyl, 2-bromo-4-fluorobenzyl, 2-fluoro-4-bromobenzyl, 2-chloro-4-fluorobenzyl, 2-fluoro-4-chlorobenzyl, 2-bromo-4-chlorobenzyl, 2-chloro-4-bromobenzyl, 2-iodo-4-bromobenzyl, 3-chloro-5-bromobenzyl, 3-bromo-5-fluorobenzyl, 3-chloro-5-fluorobenzyl, 3-iodo-5-bromobenzyl, 3-chloro-5-iodobenzyl and so on.
The lower alkenyl group includes vinyl, 1-methylvinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 2,2-dimethylvinyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and so on.
The carboxy(lower)alkyl group includes carboxymethyl, 1-carboxyethyl, 2-carboxyethyl, 1-carboxypropyl, 2-carboxypropyl, 3-carboxypropyl, 4-carboxybutyl, 5-carboxypentyl, 6-carboxyhexyl and so on.
The (lower)alkoxycarbonyl(lower)alkyl group includes methoxycarbonylmethyl, ethoxycarbonylmethyl, propoxycarbonylmethyl, isopropoxycarbonylmethyl, butoxycarbonylmethyl, tert-butoxycarbonylmethyl, pentyloxycarbonylmethyl, hexyloxycarbonylmethyl, 1-methoxycarbonylethyl, 2-methoxycarbonylethyl, 1-ethoxycarbonylethyl, 2-ethoxycarbonylethyl, 3-methoxycarbonylpropyl, 3-ethoxycarbonylpropyl, 4-ethoxycarbonylbutyl, 5-ethoxycarbonylpentyl, 6-ethoxycarbonylhexyl and so on.
The halogen-substituted lower alkyl group includes trifluoromethyl, pentafluoroethyl, heptafluoropropyl, nonafluorobutyl, undecafluoropentyl, tridecafluorohexyl and so on.
The (lower)alkoxy(lower)alkyl group includes methoxymethyl, ethoxymethyl, propoxymethyl, butoxymethyl, pentyloxymethyl, hexyloxymethyl, 2-methoxyethyl, 3-methoxypropyl, 4-methoxybutyl, 5-methoxypentyl, 6-methoxyhexyl and so on.
The lower alkynyl group includes ethynyl, 2-propynyl, 3-butynyl, 4-pentyn

REFERENCES:
patent: 5624918 (1997-04-01), Kuroki et al.
Chemical Abstract, "Preparation of quinolines as hypolipemics and antidiabetics" vol. 119: 95360, Aug. 30, 1993.

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