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US 5,470,851 AGranted
Thiazolidinecarboxylic acid amide derivatives and their therapeutic uses
AssigneeSankyo Company, Limited
InventorsHiroshi Fukumi, Toshiaki Sakamoto, Mitsuo Sugiyama, Takeshi Yamaguchi, Takeshi Oshima, Fumitoshi Asai, Yasuteru Iijima
Life of this patent
Estimating the term…
Abstract
Thiazolidinecarboxylic acid amides having combined antiallergic and antiasthmatic activities with an antagonist activity against platelet Activating Factor and having the following general formula (I) ##STR1##
Claims90
A compound of formula (I):
- ##STR65## wherein:
- R.sup.1 represents a pyridyl group which is unsubstituted or is substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms and alkoxy groups having from 1 to 4 carbon atoms;
- R.sup.2 represents a hydrogen atom, or a pyridyl group which is unsubstituted or is substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms and alkoxy groups having from 1 to 4 carbon atoms;
- R.sup.3 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
- R.sup.4 represents a group of formula (II), (III), (IV), (V) or (VI):
- ##STR66## wherein:
- R.sup.5 represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
- R.sup.6 and R.sup.7 are independently selected from the group consisting of:
- unsubstituted phenyl groups,
- substituted phenyl groups which are substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having 1 to 4 carbon atoms and having at least one halogen atom, alkoxy groups having from 1 to 4 carbon atoms and halogen atoms,
- cycloalkyl groups having from 3 to 6 ring carbon atoms, and
- aromatic heterocyclic groups having 5 or 6 ring atoms of which from 1 to 3 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur atoms and the remainder are carbon atoms;
- R.sup.8 and R.sup.9 are independently from the group consisting of hydrogen atoms, alkyl groups having from 1 to 4 carbon atoms, haloalkyl groups having from 1 to 4 carbon atoms and having at least one halogen atom, alkoxy groups having from 1 to 4 carbon atoms, hydroxy groups and halogen atoms;
- A.sup.1 represents a group of formula (VII) or (VIII):
- ##STR67## where:
- R.sup.1 and R.sup.11 are independently selected from the group consisting of hydrogen atoms and alkyl groups having from 1 to 4 carbon atoms;
- D represents an alkylene or alkylidene group having from 2 to 5 carbon atoms;
- and
- n is 2 or 3;
- A.sup.2 represents a group of formula (VIII), above, or (IX):
- ##STR68## where R.sup.10 is as defined above;
- and B represents an alkylene or alkylidene group having from 2 to 4 carbon atoms;
- or
- --A.sup.2 --B--represents a single bond;
- or a pharmaceutically acceptable salt thereof.
22 more elements
Compounds of formula (I):
- ##STR75## wherein:
- R.sup.1 represents a pyridyl group which is unsubstituted or is substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms and alkoxy groups having from 1 to 4 carbon atoms;
- R.sup.2 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, or a pyridyl group which is unsubstituted or which is substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms and alkoxy groups having from 1 to 4 carbon atoms;
- R.sup.3 represents a hydrogen atom, an alkyl group having from 1 to 4 carbon atoms, an alkoxycarbonyl group having from 2 to 5 carbon atoms, an aralkyloxycarbonyl group in which the alkyl part has from 1 to 4 carbon atoms and the aryl part is as defined below, an aryloxycarbonyl group in which the aryl part is as defined below, an aliphatic carboxylic acyl group having from 1 to 5 carbon atoms, an aliphatic carboxylic acyl group which has from 2 to 5 carbon atoms and which is substituted by at least one halogen atom, an arylcarbonyl group in which the aryl part is as defined below, an alkylsulfonyl group having from 1 to 4 carbon atoms, an arylsulfonyl group in which the aryl part is as defined below, or a group formula -B'-NR.sup.5' R.sup.6', in which
- B' represents an alkylene or alkylidene group having from 2 to 4 carbon atoms;
- and
- R.sup.5' and R.sup.6' are independently selected from the group consisting of hydrogen atoms and alkyl groups having from 1 to 4 carbon atoms;
- said aryl groups have from 6 to 10 ring atoms and are unsubstituted or are substituted by at least one substituent selected from the group consisting of alkyl groups having from 1 to 4 carbon atoms, alkoxy groups having from 1 to 4 carbon atoms and halogen atoms;
- R.sup.4 represents a group of formula (VI)':
- ##STR76## R.sup.4' represents a hydrogen atom or an alkyl group having from 1 to 4 carbon atoms;
- A' represents an alkylene or alkylidene group having from 2 to 7 carbon atoms;
- and
- Z' represents a group of formula:
- ##STR77## or a group of formulae (II)', (III)', (IV)' or (V)' in which one or more of the ring atoms is substituted by an alkyl group having from 1 to 4 carbon atoms;
- in which:
- R.sup.7' and R.sup.8' are independently selected from the group consisting of unsubstituted phenyl groups, substituted phenyl groups which are substituted by at least one substituent selected from the group consisting of substituents (a), defined below, and aromatic heterocyclic groups which have 5 or 6 ring atoms of which 1 or 2 are hetero-atoms selected from the group consisting of nitrogen, oxygen and sulfur hetero-atoms, said aromatic heterocyclic groups being unsubstituted or being substituted by at least one substituent selected from the group consisting of substituents (a), defined below;
- said substituents (a) 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, halogen atoms and haloalkyl groups having from 1 to 4 carbon atoms;
- E' represents a direct carbon-carbon single bond or an oxygen atom;
- and
- m is 2 or 3;
- or a pharmaceutically acceptable salt thereof.
18 more elements
Dependencies are inferred from the claim text.