Claims
- 1. A method for phosphodiesterase inhibition, which uses, as an active ingredient, a carbostyril derivative or salt thereof of formula (1) ##STR240## wherein A is a lower alkylene group; R is a group ##STR241## a group ##STR242## or a group ##STR243## wherein R.sup.1 is a group ##STR244## (wherein l and m independently are 0 or 1, B is a lower alkylene group and each of R.sup.7 and R.sup.8, which may be the same or different, is a hydrogen atom, a lower alkyl group which may have a hydroxyl group, or a lower alkanoyl group or R.sup.7 and R.sup.8 may form a five- or six-membered saturated heterocyclic ring together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom between R.sup.7 and R.sup.8 said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkyl group-substituted or unsubstituted amino group, a lower alkoxy-lower alkoxy group, an oxo group and a lower alkyl group-substituted or unsubstituted aminocarbonyl group or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sup.1 is a lower alkoxycarbonyl group-substituted lower alkyl group; a carboxy group-substituted lower alkyl group; a lower alkyl group having, as a substituent, a lower alkyl group-substituted or unsubstituted aminocarbonyl group; a hydroxyl group-containing lower alkyl group; an imidazolyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group; or a group --SO.sub.2 -D-R.sup.9 (wherein D is a lower alkylene group, and R.sup.9 is a five- or six-memebered saturated or unsaturated heterocyclic ring residue having from 1-3 halogen atoms or nitrogen atoms, said heterocyclic ring may have, as a substituent, a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkoxycarbonyl group, or a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group);
- R.sup.2 is a hydrogen atom; a cycloalkyl-lower alkyl group; a cycloalkyl group; a phenyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, a carboxy group and a lower alkoxy group; a pyridyl-substituted lower alkyl group; a thienyl-substituted lower alkyl group; a cycloalkylcarbonyl group; a benzoyl group; a tetrahydropyranyl-substituted lower alkyl group; a phenyl-lower alkylsulfonyl group; a phenylsulfonyl group; or a cycloalkyl-lower alkylsulfonyl group;
- R.sup.1 and R.sup.2 may form a pyrrolidinyl group together with the nitrogen atom to which they bond, said pyrrolidinyl group having from 1-2 substituents selected from the group consisting of a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkoxycarbonyl group, a piperidinylcarbonyl group and a cycloalkyl-lower alkyl group-substituted or unsubstituted aminocarbonyl group;
- R.sup.3 is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; a carboxy-substituted lower alkyl group; a lower alkoxycarbonyl group-substituted lower alkyl group; a group ##STR245## (wherein E is a lower alkylene group which may have a hydroxyl group, n is 0 or 1, and each of R.sup.10 and R.sup.11, which may be the same or different, is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; or a lower alkanoyl group, or R.sup.10 and R.sup.11 may form a five- or six-membered saturated heterocyclic ring, together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom present between R.sup.10 and R.sup.11, said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, an oxo group, a lower alkoxy-lower alkoxy group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, and a lower alkyl-substituted or unsubstituted amino group, or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sup.3 is a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group;
- R.sup.4 is a hydrogen atom; a cycloalkyl group; a cycloalkyl-lower alkyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; a phenyl group; a thienyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; an imidazolyl-substituted lower alkyl group; or a tetra-hydropyranyl substituted lower alkyl group;
- Y is a group ##STR246## a group ##STR247## or a group ##STR248## each of R.sup.5 and R.sup.6, which may be the same or different, is a hydrogen atom; a lower alkyl group; a cycloalkyl group; a cycloalkyl-lower alkyl group; or a piperidinyl-lower alkyl group which may have, as a substituent on the piperidinyl ring, a lower alkoxy-lower alkoxy group or a hydroxyl group; and
- W is an oxygen atom or a sulfur atom, the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton being a single bond or a double bond.
- 2. A method for platelets adhesion inhibition, which uses, as an active ingredient, a carbostyril derivative or salt thereof of formula (1) ##STR249## wherein A is a lower alkylene group; R is a group ##STR250## a group ##STR251## or a group ##STR252## wherein R.sup.1 is a group ##STR253## (wherein l and m independently are 0 or 1, B is a lower alkylene group and each of R.sup.7 and R.sup.8, which may be the same or different, is a hydrogen atom, a lower alkyl group which may have a hydroxyl group, or a lower alkanoyl group or R.sup.7 and R.sup.8 may form a five- or six-membered saturated heterocyclic ring together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom between R.sup.7 and R.sup.8, said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkyl group-substituted or unsubstituted amino group, a lower alkoxy-lower alkoxy group, an oxo group and a lower alkyl group-substituted or unsubstituted aminocarbonyl group or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sup.1 is a lower alkoxycarbonyl group-substituted lower alkyl group; a carboxy group-substituted lower alkyl group; a lower alkyl group having, as a substituent, a lower alkyl group-substituted or unsubstituted aminocarbonyl group; a hydroxyl group-containing lower alkyl group; an imidazolyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group; or a group --SO.sub.2 -D-R.sup.9 (wherein D is a lower alkylene group, and R.sup.9 is a five- or six-memebered saturated or unsaturated heterocyclic ring residue having from 1-3 halogen atoms or nitrogen atoms, said heterocyclic ring may have, as a substituent, a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkoxycarbonyl group, or a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group);
- R.sup.2 is a hydrogen atom; a cycloalkyl-lower alkyl group; a cycloalkyl group; a phenyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, a carboxy group and a lower alkoxy group; a pyridyl-substituted lower alkyl group; a thienyl-substituted lower alkyl group; a cycloalkylcarbonyl group; a benzoyl group; a tetrahydropyranyl-substituted lower alkyl group; a phenyl-lower alkylsulfonyl group; a phenylsulfonyl group; or a cycloalkyl-lower alkylsulfonyl group;
- R.sup.1 and R.sup.2 may form a pyrrolidinyl group together with the nitrogen atom to which they bond, said pyrrolidinyl group having from 1-2 substituents selected from the group consisting of a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkoxycarbonyl group, a piperidinylcarbonyl group and a cycloalkyl-lower alkyl group-substituted or unsubstituted aminocarbonyl group;
- R.sup.3 is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; a carboxy-substituted lower alkyl group; a lower alkoxycarbonyl group-substituted lower alkyl group; a group ##STR254## (wherein E is a lower alkylene group which may have a hydroxyl group, n is 0 or 1, and each of R.sup.10 and R.sup.11 which may be the same or different is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; or a lower alkanoyl group, or R.sup.10 and R.sup.11 may form a five- or six-membered saturated heterocyclic ring, together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom present between R.sup.10 and R.sup.11, said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, an oxo group, a lower alkoxy-lower alkoxy group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, and a lower alkyl-substituted or unsubstituted amino group, or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sup.3 is a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group;
- R.sup.4 is a hydrogen atom; a cycloalkyl group; a cycloalkyl-lower alkyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; a phenyl group; a thienyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; an imidazolyl-substituted lower alkyl group; or a tetra-hydropyranyl substituted lower alkyl group;
- Y is a group ##STR255## a group ##STR256## or a group ##STR257## each of R.sup.5 and R.sup.6, which may be the same or different, is a hydrogen atom; a lower alkyl group; a cycloalkyl group; a cycloalkyl-lower alkyl group; or a piperidinyl-lower alkyl group which may have, as a substituent on the piperidinyl ring, a lower alkoxy-lower alkoxy group or a hydroxyl group; and
- W is an oxygen atom or a sulfur atom, the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton being a single bond or a double bond.
- 3. A process for producing a carbostyril compound of the formula (1A) ##STR258## wherein A is a lower alkylene group; W is an oxygen or sulfur atom; R.sup.A is a group ##STR259## wherein R.sub.1 is a group ##STR260## (wherein l and m independently are 0 or 1, B is a lower alkylene group, and each of R.sup.7 and R.sup.8, which may be the same or different, is a hydrogen atom, a lower alkyl group which may have a hydroxyl group, or a lower alkanoyl group or R.sup.7 and R.sup.8 may form a five- or six-membered saturated heterocyclic ring together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom between R.sup.7 and R.sup.8, said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkyl group-subsituted or unsubstituted amino group, a lower alkoxy-lower alkoxy group, an oxo group and a lower alkyl group-substituted or unsubstituted aminocarbonyl group or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sup.1 is a lower alkoxycarbonyl group-substituted lower alkyl group; a carboxy group-substituted lower alkyl group; a lower alkyl group having, as a substituent, a lower alkyl group-substituted or unsubstituted aminocarbonyl group; a hydroxyl group-containing lower alkyl group; an imidazolyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group; or a group --SO.sub.2 -D-R.sup.9 (wherein D is a lower alkylene group and R.sup.9 is a five- or six-membered saturated or unsaturated heterocyclic ring residue having from 1-3 halogen atoms or nitrogen atoms, said heterocyclic ring may have, as a substituent, a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkoxy-carbonyl group, or a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group);
- R.sup.2 is a hydrogen atom; a cycloalkyl-lower alkyl group; a cycloalkyl group; a phenyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, a carboxy group and a lower alkoxy group; a pyridyl-substituted lower alkyl group; a thienyl-substituted lower alkyl group; a cycloalkylcarbonyl group; a benzoyl group; a tetrahydropyranyl-substituted lower alkyl group; a phenyl-lower alkylsulfonyl group; a phenyl-sulfonyl group; or a cycloalkyl-lower alkylsulfonyl group; or
- R.sup.1 and R.sup.2 may form a pyrrolidinyl group together with the nitrogen atom to which they bond, said pyrrolidinyl group having from 1-2 substituents selected from the group consisting of a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkyl group having a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkoxycarbonyl group, a piperidinylcarbonyl group and a cycloalkyl-lower alkyl group-substituted or unsubstituted aminocarbonyl group; and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a single or double bond comprising reacting a compound (2) represented by general formula (2) ##STR261## (wherein A, W and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton have the same definitions as given above; and X represents a halogen atom, a lower alkanesulfonyloxy group, and arylsulfonyloxy group or an aralkylsulfonyloxy group) with a compound (3) represented by general formula (3)
- (wherein R.sup.A has the same definition as given above) in an appropriate solvent or in the absence of any solvent in the presence or absence of a basic compound.
- 4. A process for producing a carbostyril compound of the formula 1(b) ##STR262## wherein A is an alkylene group; W is an oxygen or sulfur atom; R.sup.3 is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; a carboxy-substituted lower alkyl group; a lower alkoxycarbonyl group-substituted lower alkyl group; a ##STR263## (wherein E is a lower alkylene group which may have a hydroxyl group, n is 0 or 1, and each of R.sup.10 and R.sup.11, which may be the same or different, is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; or a lower alkanoyl group, or R.sup.10 and R.sup.11 may form a five- or six-membered saturated heterocyclic ring together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom present between R.sup.10 or R.sup.11, said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, an oxo group, a lower alkoxy-lower alkoxy group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group and a lower alkyl substituted or unsubstituted amino group or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sub.3 is a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group;
- R.sup.4 is a hydrogen atom; a cycloalkyl group; a cycloalkyl-lower alkyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; a phenyl group; a thienyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; an imidazolyl-substituted lower alkyl group; or a tetra-hydropyranyl-substituted lower alkyl group; and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a single or double bond comprising reacting a compound (6) represented by general formula (6) ##STR264## (wherein A, W and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton have the same definitions as give above; and X.sup.1 represents a halogen atom.) with a compound (7) represented by general formula (7) ##STR265## (wherein R.sup.3 and R.sup.4 have the same definitions as given above) in an appropriate solvent or in the absence of any solvent in the presence or absence of a basic compound.
- 5. A process for producing a carbostyril compound of the formula (1c). ##STR266## wherein A is an alkylene group; W is an oxygen or sulfur atom; each of R.sup.5 and R.sup.6, which may be the same or different, is a hydrogen atom; a lower alkyl group; a cycloalkyl group; a cycloalkyl-lower alkyl group; or a piperidinyl-lower alkyl group which may have, as a substituent on the piperidinyl ring, a lower alkoxy-lower alkoxy group or a hydroxyl group; and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a single bond or a double bond; comprising reacting a compound (8) represented by general formula (8) ##STR267## (wherein A, W and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton have the same definitions as given above) with a compound (9) represented by general formula (9) ##STR268## (wherein R.sup.5 and R.sup.6 have the same definitions as given above) in an appropriate solvent.
- 6. A process for producing a carbostyril compound of the formula (1m) ##STR269## wherein A is an alkylene group; W is an oxygen or sulfur atom; R.sup.2 is a hydrogen atom; a cycloalkyl-lower alkyl group; a cycloalkyl group; a phenyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, a carboxy group and a lower alkoxy group; a pyridyl-substituted lower alkyl group; a thienyl-substituted lower alkyl group; a cycloalkylcarbonyl group; a benzoyl group; a tetrahydropyranyl-substituted lower alkyl group; a phenyl-lower alkylsulfonyl group; a phenylsulfonyl group; or a cycloalkyl-lower alkylsulfonyl group; D is a lower alkylene group; and R.sup.9b is a five- or six-membered saturated or unsaturated heterocyclic ring residue containing 1-3 nitrogen atoms, which residue may have one or more substituents selected from a hydroxyl group; a lower alkoxy-lower alkoxy group; a lower alkoxycarbonyl group or a lower alkyl group which may be substituted with a lower alkoxy-lower alkoxy group or a hydroxyl group; and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a single or double bond; comprising reacting a compound (24) represented by general formula (24) ##STR270## (wherein A, R.sup.2, D and the carbon-to-carbon bond between the 3+and 4-positions of the carbostyril skeleton have the same definitions as given above; and R.sup.9a represents a halogen atom) with a compound (25) represented by general formula (25)
- R.sup.9b --H (25)
- (wherein R.sup.9b has the same definition as given above) in an appropriate solvent or in the absence of any solvent in the presence or absence of a basic compound.
- 7. A process for producing a carbostyril compound of the formula (1o) ##STR271## wherein A is an alkylene group; R is a group ##STR272## a group ##STR273## or a group ##STR274## wherein R.sup.1 is a group ##STR275## (wherein l and m independently are 0 or 1, B is a lower alkylene group and each of R.sup.7 and R.sup.8, which may be the same or different, is a hydrogen atom, a lower alkyl group which may have a hydroxyl group, or a lower alkanoyl group or R.sup.7 and R.sup.8 may form a five- or six-membered saturated heterocyclic ring together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom between R.sup.7 and R.sup.8 said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkyl group-substituted or unsubstituted amino group, a lower alkoxy-lower alkoxy group, an oxo group and a lower alkyl group-substituted or unsubstituted aminocarbonyl group or said heterocyclic ring may-also have a lower alkylenedioxy group as a substituent); or R.sup.1 is a lower alkoxycarbonyl group-substituted lower alkyl group; a carboxy group-substituted lower alkyl group; a lower alkyl group having, as a substituent, a lower alkyl group-substituted or unsubstituted aminocarbonyl group; a hydroxyl group-containing lower alkyl group; an imidazolyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group; or a group --So.sub.2 -D-R.sup.9 (wherein D is a lower alkylene group, and R.sup.9 is a five- or six-memebered saturated or unsaturated heterocyclic ring residue having from 1-3 halogen atoms or nitrogen atoms, said heterocyclic ring may have, as a substituent, a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkoxycarbonyl group, or a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group);
- R.sup.2 is a hydrogen atom; a cycloalkyl-lower alkyl group; a cycloalkyl group; a phenyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group, a cyano group, a carboxy group and a lower alkoxy group; a pyridyl-substituted lower alkyl group; a thienyl-substituted lower alkyl group; a cycloalkylcarbonyl group; a benzoyl group; a tetrahydropyranyl-substituted lower alkyl group; a phenyl-lower alkylsulfonyl group; a phenylsulfonyl group; or a cycloalkyl-lower alkylsulfonyl group;
- R.sup.1 and R.sup.2 may form a pyrrolidinyl group together with the nitrogen atom to which they bond, said pyrrolidinyl group having from 1-2 substituents selected from the group consisting of a hydroxyl group, a lower alkoxy-lower alkoxy group, a lower alkyl group having a lower alkoxy-lower alkoxy group or a hydroxyl group, a lower alkoxycarbonyl group, a piperidinylcarbonyl group and a cycloalkyl-lower alkyl group-substituted or unsubstituted aminocarbonyl group;
- R.sup.3 is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; a carboxy-substituted lower alkyl group; a lower alkoxycarbonyl group-substituted lower alkyl group; a group ##STR276## (wherein E is a lower alkylene group which may have a hydroxyl group, n is 0 or 1, and each of R.sup.10 and R.sup.11 which may be the same or different is a hydrogen atom; a lower alkyl group which may have a hydroxyl group; or a lower alkanoyl group, or R.sup.10 and R.sup.11 may form a five- or six-membered saturated heterocyclic ring, together with the nitrogen atom to which they bond and further with or without a nitrogen, oxygen or sulfur atom present between R.sup.10 and R.sup.11, said heterocyclic ring may have from 1-3 substituents selected from the group consisting of a hydroxyl group, an oxo group, a lower alkoxy-lower alkoxy group, a lower alkyl group which may have a lower alkoxy-lower alkoxy group or a hydroxyl group, and a lower alkyl-substituted or unsubstituted amino group, or said heterocyclic ring may also have a lower alkylenedioxy group as a substituent); or R.sup.3 is a pyrrolidinyl-lower alkyl group which may have, as substituents on the pyrrolidine ring, from 1-3 groups selected from the group consisting of a lower alkyl group, a lower alkoxy-lower alkoxy group and a hydroxyl group;
- R.sup.4 is a hydrogen atom; a cycloalkyl group; a cycloalkyl-lower alkyl group; a phenyl-lower alkyl group which may have, as substituents on the phenyl ring, from 1-3 groups selected from the group consisting of a halogen atom, a lower alkyl group and a lower alkoxy group; a phenyl group; a thienyl-substituted lower alkyl group; a pyridyl-substituted lower alkyl group; an imidazolyl-substituted lower alkyl group; or a tetra-hydropyranyl substituted lower alkyl group;
- Y is a group ##STR277## a group ##STR278## or a group ##STR279## each of R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom; a lower alkyl group; a cycloalkyl group; a cycloalkyl-lower alkyl group; or a piperidinyl-lower alkyl group which may have, as a substituent on the piperidinyl ring, a lower alkoxy-lower alkoxy group or a hydroxyl group; and
- the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a single bond or a double bond; comprising reacting a compound (1n) represented by general formula (1n) ##STR280## (wherein A, R, and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton have the same definitions as given above) with P.sub.2 S.sub.5 or a Lawesson's reagent.
- 8. A process for producing a carbostyril compound of formula (1s) ##STR281## wherein A is an alkylene group, W is an oxygen or sulfur atom; each of R.sup.5 and R.sup.6, which may be the same or different, is a hydrogen atom; a lower alkyl group; a cycloalkyl group; a cycloalkyl-lower alkyl group; or a piperidinyl-lower alkyl group which may have, as a substituent on the piperidinyl ring, a lower alkoxy-lower alkoxy group or a hydroxyl group; and
- the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton is a single bond or a double bond; comprising reacting a compound (76) represented by general formula (76) ##STR282## (wherein A, R.sup.5 and R.sup.6 and the carbon-to-carbon bond between the 3- and 4-positions of the carbostyril skeleton have the same definitions as given above) with P.sub.2 S.sub.5 or a Lawesson's reagent.
Priority Claims (1)
Number |
Date |
Country |
Kind |
3-211268 |
Aug 1991 |
JPX |
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Parent Case Info
This is a division of application Ser. No. 08/039,301, filed as PCT/JP92/01041, Aug. 18, 1992, now U.S. Pat. No. 5,506,239.
US Referenced Citations (10)
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Divisions (1)
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Number |
Date |
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Parent |
39301 |
Apr 1993 |
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