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US 5,688,823 AGranted
Thiazolidine and oxazolidine derivatives their preparation and their medical use
AssigneeSankyo Company, Limited
InventorsTakashi Fujita, Koichi Fujimoto, Takao Yoshioka, Hiroaki Yanagisawa, Toshihiko Fujiwara, Hiroyoshi Horikoshi, Minoru Oguchi, Kunio Wada
Life of this patent
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Abstract
Compounds of formula (I): ##STR1## Z is a group of formula (iii), (iv),: ##STR2## and salts, esters and solvates thereof and pro-drugs therefor are useful for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, glucose tolerance insufficiency, insulin resistance and diabetic complications.
Claims31
A compound of formula (I):
- ##STR39## wherein:
- R.sup.1 and R.sup.2 are the same or different and each represents a hydrogen atom or an alkyl group having from 1 to 8 carbon atoms, or R.sup.1 and R.sup.2 together represent a group of formula --(CH.sub.2).sub.k --
- wherein K represents an integer of from 2 to 6;
- R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxy group having from 1 to 4 carbon atoms, a halogen atom or a hydroxy group;
- A and B are the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, an aralkyl group in which an alkyl group having from 1 to 5 carbon atoms is substituted by an aryl group as defined below, an aliphatic carboxylic acyl group having from 1 to 11 carbon atoms, an aliphatic carboxylic acyl group which has from 2 to 6 carbon atoms and which is substituted by an aryl group as defined below, an aromatic carboxylic acyl group in which the aryl part is as defined below, a carbamoyl group of formula --CONR.sup.6 R.sup.7,
- wherein R.sup.6 and R.sup.7 are the same or different and each represents a hydrogen atom, an alkyl group having from 1 to 1l carbon atoms, an aryl group as defined below or an aralkyl group in which an alkyl group having from 1 to 5 carbon atoms is substituted by an aryl group as defined below;
- or A and B together represent a group of formula >C.dbd.O, a group of formula >C.dbd.S, a group of formula --C(.dbd.O)--C(.dbd.O)--, a group of formula --CH.sub.2 C(.dbd.O)--, a group of formula --CH.sub.2 CH.sub.2 --, a group of formula --SO.sub.2 -- or a group of formula --CH.sub.2 SO.sub.2 --;
- X represents a group of formula:
- W--(CH.sub.2).sub.m --X.sup.1 --
- wherein W represents
- an aryl group as defined below, a heterocyclic group having 5 or 6 ring atoms of which from 1 to 3 are hetero-atoms selected from the group consisting of oxygen, sulfur and nitrogen hetero-atoms and being unsubstituted or being substituted by at least one substituent selected from the group consisting of substituents .alpha. as defined below or such a heterocyclic group which is fused to at least one ring system selected from the group consisting of carbocyclic and heterocyclic rings having 5 or 6 ring atoms and which is unsubstituted or is substituted by at least one substituent selected from the group consisting of substituents .alpha. as defined below,
- X.sup.1 represents a single bond, an oxygen atom, a sulfur atom or a group of formula >NR.sup.4
- wherein R.sup.4 represents a hydrogen atom, an alkyl group having from 1 to 8 carbon atoms, an alkyl group in which an alkyl group having from 1 to 5 carbon atoms is substituted by at least one aryl group as defined below or an aryl group as defined below, and
- m represents 0 or an integer of from 1 to 8;
- Y represents a group of formula:
- --(CH.sub.2).sub.n --Y.sup.1 --
- wherein Y.sup.1 represents a single bond, an oxygen atom or a sulfur atom, and n represents an integer of from 1 to 5;
- Z represents a group of formula (iii) or (iv), (v) or (vi):
- ##STR40## wherein R.sup.5 represents a hydrogen atom, a carboxyalkyl group having from 2 to 5 carbon atoms, an alkanoyloxyalkyl group having a total of from 2 to 12 carbon atoms, a cycloalkyl-substituted alkanoyloxyalkyl group having a total of from 6 to 12 carbon atoms, a cycloalkylcarbonyloxyalkyl group having a total of from 5 to 17 carbon atoms, an alkoxycarbonyloxyalkyl group having a total of from 3 to 17 carbon atoms, a cycloalkyl-substituted alkoxycarbonyloxyalkyl group having a total of from 6 to 17 carbon atoms or a cycloalkyloxycarbonyloxyalkyl group having a total of from 5 to 17 carbon atoms;
- said aryl groups are carbocyclic aromatic groups which have from 6 to 14 ring carbon atoms and which are unsubstituted or are substituted by at least one substituent selected from the group consisting of substituents .alpha., defined below;
- and
- said substituents .alpha. are selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms, hydroxy groups, halogen atoms, phenyl groups, nitro groups and groups of formula --NR.sup.a R.sup.b,
- wherein R.sup.a and R.sup.b are independently selected from the group consisting of hydrogen atoms, alkyl groups having from 1 to 8 carbon atoms, aralkyl groups in which an alkyl group having from 1 to 5 carbon atoms is substituted by an aryl group as defined above, aryl groups as defined above, aliphatic carboxylic acyl groups having from 1 to 11 carbon atoms, aliphatic carboxylic acyl groups which have from 2 to 6 carbon atoms and which are substituted by an aryl group as defined above, and aromatic carboxylic acyl groups in which the aryl part is as defined above, provided that any aryl group represented by or included in a group represented by R.sup.a or R.sup.b is not itself further substituted by a group of formula --NR.sup.a R.sup.b ;
- or a salt or ester thereof.
21 more elements
Dependencies are inferred from the claim text.