Alkanoic acid derivatives process for their production and use thereof
View Patent ↗An alkanoic acid derivative useful as a prophylactic or therapeutic agent of diabetes mellitus, hyperlipidemia, impaired glucose tolerance and the like can be provided by a compound represented by the formula wherein R 1 is an optionally substituted 5-membered aromatic heterocyclic group; X is a bond and the like; Q is a divalent hydrocarbon group having 1 to 20 carbon atoms; Y is a bond and the like; ring A is an aromatic ring optionally further having 1 to 3 substituents; Z is —(CH 2 ) n -Z 1 -(n is an integer of 1 to 8 and Z 1 is an oxygen atom and the like) and the like; ring B is a pyridine ring optionally further having 1 to 3 substituents, and the like; U is a bond and the like; W is a divalent hydrocarbon group having 1 to 20 carbon atoms; and R 3 is —OH and the like, provided that, when ring B is a benzene ring optionally further having 1 to 3 substituents, U should be a bond, or a salt thereof.
1. A compound represented by the formula
wherein
R 1 is an oxazolyl group which may have 1 to 4 substituents selected from the group consisting of
(1) halogen atom,
(2) nitro group,
(3) an aliphatic hydrocarbon group having 1 to 15 carbon atoms,
(4) an alicyclic hydrocarbon group having 3 to 12 carbon atoms,
(5) an aromatic hydrocarbon group having 6 to 14 carbon atoms,
(6) an acyl group which may have 1 to 3 substituents selected from the group consisting of a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, nitro, hydroxy, and amino,
(7) an amino group optionally mono- or di-substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, cycloalkenyl group having 3 to 10 carbon atoms, aryl group having 6 to 14 carbon atoms or acyl group having 1 to 13 carbon atoms,
(8) a hydroxy group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 1 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms, each of which group may have 1 or 2 substituents selected from the group consisting of a halogen atom and an alkoxy group having 1 to 3 carbon atoms, and
(9) a thiol group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 2 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms,
wherein the above (3) may have 1 to 3 substituents selected from the group consisting of
1) a cycloalkyl group having 3 to 10 carbon atoms,
2) an aryl group having 6 to 14 carbon atoms,
3) an aralkyl group having 7 to 9 carbon atoms,
4) an amino group,
5) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
6) an amidino group,
7) an acyl group having 2 to 8 carbon atoms,
8) a carbamoyl group,
9) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
10) a sulfamoyl group,
11) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a carboxyl group,
13) an alkoxycarbonyl group having 2 to 8 carbon atoms,
14) a hydroxy group,
15) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
16) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
17) a cycloalkyloxy group having 3 to 7 carbon atoms,
18) an aralkyloxy group having 7 to 9 carbon atoms,
19) an aryloxy group having 6 to 14 carbon atoms,
20) a thiol group,
21) a C 1-6 alkylthio group optionally substituted by 1 to 3 carbon atoms,
22) an aralkylthio group having 7 to 9 carbon atoms,
23) an arylthio group having 6 to 14 carbon atoms,
24) a sulfo group,
25) a cyano group,
26) an azide group,
27) a nitro group,
28) a nitroso group, and
29) a halogen atom,
wherein the above (4) and (5) may have 1 to 3 substituents selected from the group consisting of
1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms,
2) a C 2-6 alkenyl group optionally substituted by 1 to 3 halogen atoms,
3) a cycloalkyl group having 3 to 10 carbon atoms,
4) an aromatic hydrocarbon group having 6 to 14 carbon atoms,
5) an aralkyl group having 7 to 9 carbon atoms,
6) an amino group,
(7) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
8) an amidino group,
9) an acyl group having 2 to 8 carbon atoms,
10) a carbamoyl group,
11) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a sulfamoyl group,
13) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
14) a carboxyl group,
15) an alkoxycarbonyl group having 2 to 8 carbon atoms,
16) a hydroxy group,
17) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
18) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
19) a cycloalkyloxy group having 3 to 7 carbon atoms,
20) an aralkyloxy group having 7 to 9 carbon atoms,
21) an aryloxy group having 6 to 14 carbon atoms,
22) a thiol group,
23) a C 1-6 alkylthio group optionally substituted by 1 to 3 halogen atoms,
24) an aralkylthio group having 7 to 9 carbon atoms,
25) an arylthio group having 6 to 14 carbon atoms,
26) a sulfo group,
27) a cyano group,
28) an azide group,
29) a nitro group,
30) a nitroso group, and
31) a halogen atom;
X is a bond;
Q is an alkylene group having 1 to 20 carbon atoms;
Y is an oxygen atom;
ring A is a benzene ring optionally further having 1 to 3 substituents selected from the group consisting of
(1) an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have 1 to 3 substituents selected from the group consisting of
1) a cycloalkyl group having 3 to 10 carbon atoms,
2) an aryl group having 6 to 14 carbon atoms,
3) an aralkyl group having 7 to 9 carbon atoms,
4) an amino group,
5) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
6) an amidino group,
7) an acyl group having 2 to 8 carbon atoms,
8) a carbamoyl group,
9) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
10) a sulfamoyl group,
11) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a carboxyl group,
13) an alkoxycarbonyl group having 2 to 8 carbon atoms,
14) a hydroxy group,
15) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
16) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
17) a cycloalkyloxy group having 3 to 7 carbon atoms,
18) an aralkyloxy group having 7 to 9 carbon atoms,
19) an aryloxy group having 6 to 14 carbon atoms,
20) a thiol group,
21) a C 1-6 alkylthio group optionally substituted by 1 to 3 carbon atoms,
22) an aralkylthio group having 7 to 9 carbon atoms,
23) an arylthio group having 6 to 14 carbon atoms,
24) a sulfo group,
25) a cyano group,
26) an azide group,
27) a nitro group,
28) a nitroso group, and
29) a halogen atom,
(2) a hydroxy group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 1 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms, each of which group may have 1 to 2 substituents selected from the group consisting of a halogen atom and an alkoxy group having 1 to 3 carbon atoms,
(3) halogen atom,
(4) an acyl group which may have 1 to 3 substituents selected from the group consisting of a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, nitro, hydroxy, and amino,
(5) nitro group, and
(6) an amino group optionally mono- or di-substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, cycloalkenyl group having 3 to 10 carbon atoms, aryl group having 6 to 14 carbon atoms or acyl group having 1 to 13 carbon atoms;
Z is —(CH 2 ) n —O— (n is an integer of 1 to 8);
ring B is a pyridine ring which optionally further has 1 to 3 substituents selected from the group consisting of
(1) an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have 1 to 3 substituents selected from the group consisting of
1) a cycloalkyl group having 3 to 10 carbon atoms,
2) an aryl group having 6 to 14 carbon atoms,
3) an aralkyl group having 7 to 9 carbon atoms,
4) an amino group,
5) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
6) an amidino group,
7) an acyl group having 2 to 8 carbon atoms,
8) a carbamoyl group,
9) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
10) a sulfamoyl group,
11) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a carboxyl group,
13) an alkoxycarbonyl group having 2 to 8 carbon atoms,
14) a hydroxy group,
15) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
16) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
17) a cycloalkyloxy group having 3 to 7 carbon atoms,
18) an aralkyloxy group having 7 to 9 carbon atoms,
19) an aryloxy group having 6 to 14 carbon atoms,
20) a thiol group,
21) a C 1-6 alkylthio group optionally substituted by 1 to 3 carbon atoms,
22) an aralkylthio group having 7 to 9 carbon atoms,
23) an arylthio group having 6 to 14 carbon atoms,
24) a sulfo group,
25) a cyano group,
26) an azide group,
27) a nitro group,
28) a nitroso group, and
29) a halogen atom,
(2) an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have 1 to 3 substituents selected from the group consisting of
1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms,
2) a C 2-6 alkenyl group optionally substituted by 1 to 3 halogen atoms,
3) a cycloalkyl group having 3 to 10 carbon atoms,
4) an aromatic hydrocarbon group having 6 to 14 carbon atoms,
5) an aralkyl group having 7 to 9 carbon atoms,
6) an amino group,
(7) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
8) an amidino group,
9) an acyl group having 2 to 8 carbon atoms,
10) a carbamoyl group,
11) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a sulfamoyl group,
13) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
14) a carboxyl group,
15) an alkoxycarbonyl group having 2 to 8 carbon atoms,
16) a hydroxy group,
17) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
18) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
19) a cycloalkyloxy group having 3 to 7 carbon atoms,
20) an aralkyloxy group having 7 to 9 carbon atoms,
21) an aryloxy group having 6 to 14 carbon atoms,
22) a thiol group,
23) a C 1-6 alkylthio group optionally substituted by 1 to 3 halogen atoms,
24) an aralkylthio group having 7 to 9 carbon atoms,
25) an arylthio group having 6 to 14 carbon atoms,
26) a sulfo group,
27) a cyano group,
28) an azide group,
29) a nitro group,
30) a nitroso group, and
31) a halogen atom,
(3) a hydroxy group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 1 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms, each of which group may have 1 to 2 substituents selected from the group consisting of a halogen atom and an alkoxy group having 1 to 3 carbon atoms,
(4) halogen atom,
(5) an acyl group which may have 1 to 3 substituents selected from the group consisting of a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, nitro, hydroxy, and amino,
(6) nitro group, and
(7) an amino group optionally mono- or di-substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, cycloalkenyl group having 3 to 10 carbon atoms, aryl group having 6 to 14 carbon atoms or acyl group having 1 to 13 carbon atoms;
U is a bond;
W is an alkylene group having 1 to 20 carbon atoms; and
R 3 is —OR 8 (R 8 is a hydrogen atom, alkyl group having 1 to 4 carbon atoms, or C 6-10 aryl group optionally having 1 to 3 substituents selected from alkyl group having 1 to 4 carbon atoms and halogen atom); or a salt thereof.
2. The compound of claim 1 , wherein Q is C 1-6 alkylene.
3. The compound of claim 1 , wherein n is an integer of 1 to 3.
4. The compound of claim 1 , wherein W is a C 1-6 alkylene.
5. The compound of claim 1 , wherein R 1 is an oxazolyl group which optionally has 1 to 3 substituents selected from
1) a C 1-10 alkyl group optionally having 1 to 3 substituents selected from a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, a nitro group, a hydroxy group and an amino group;
2) a C 3-10 cycloalkyl group optionally having 1 to 3 substituents selected from a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, a nitro group, a hydroxy group and an amino group; and
3) a C 6-14 aromatic hydrocarbon group optionally having 1 to 3 substituents selected from a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, a nitro group, a hydroxy group and an amino group;
Q is a C 1-6 alkylene;
ring A is a benzene ring which optionally further has 1 to 3 substituents selected from an alkyl group having 1 to 4 carbon atoms, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an aralkyloxy group having 7 to 10 carbon atoms and a halogen atom;
Z is —(CH 2 ) n —O— wherein n is an integer of 1 to 3;
ring B is a pyridine ring which optionally further has 1 to 3 substituents selected from an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 14 carbon atoms, a hydroxy group, an alkoxy group having 1 to 4 carbon atoms, an aralkyloxy group having 7 to 10 carbon atoms and a halogen atom;
W is a C 1-6 alkylene; and
R 3 is —OR 8 wherein R 8 is a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
6. The compound of claim 1 , which is 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid or a salt thereof.
7. A pharmaceutical composition comprising the compound of claim 1 or a salt thereof and a pharmacologically acceptable carrier.
8. A method for treating diabetes mellitus in a mammal, which comprises administering an effective amount of the compound of claim 1 or a salt thereof to said mammal.
9. A production method of a compound represented by the formula
wherein
R 1 is an oxazolyl group which may have 1 to 4 substituents selected from the group consisting of
(1) halogen atom,
(2) nitro group,
(3) an aliphatic hydrocarbon group having 1 to 15 carbon atoms,
(4) an alicyclic hydrocarbon group having 3 to 12 carbon atoms,
(5) an aromatic hydrocarbon group having 6 to 14 carbon atoms,
(6) an acyl group which may have 1 to 3 substituents selected from the group consisting of a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, nitro, hydroxy, and amino,
(7) an amino group optionally mono- or di-substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, cycloalkenyl group having 3 to 10 carbon atoms, aryl group having 6 to 14 carbon atoms or acyl group having 1 to 13 carbon atoms,
(8) a hydroxy group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 1 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms, each of which group may have 1 or 2 substituents selected from the group consisting of a halogen atom and an alkoxy group having 1 to 3 carbon atoms, and
(9) a thiol group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 2 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms,
wherein the above (3) may have 1 to 3 substituents selected from the group consisting of
1) a cycloalkyl group having 3 to 10 carbon atoms,
2) an aryl group having 6 to 14 carbon atoms,
3) an aralkyl group having 7 to 9 carbon atoms,
4) an amino group,
5) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
6) an amidino group,
7) an acyl group having 2 to 8 carbon atoms,
8) a carbamoyl group,
9) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
10) a sulfamoyl group,
11) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a carboxyl group,
13) an alkoxycarbonyl group having 2 to 8 carbon atoms,
14) a hydroxy group,
15) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
16) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
17) a cycloalkyloxy group having 3 to 7 carbon atoms,
18) an aralkyloxy group having 7 to 9 carbon atoms,
19) an aryloxy group having 6 to 14 carbon atoms,
20) a thiol group,
21) a C 1-6 alkylthio group optionally substituted by 1 to 3 carbon atoms,
22) an aralkylthio group having 7 to 9 carbon atoms,
23) an arylthio group having 6 to 14 carbon atoms,
24) a sulfo group,
25) a cyano group,
26) an azide group,
27) a nitro group,
28) a nitroso group, and
29) a halogen atom,
wherein the above (4) and (5) may have 1 to 3 substituents selected from the group consisting of
1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms,
2) a C 2-6 alkenyl group optionally substituted by 1 to 3 halogen atoms,
3) a cycloalkyl group having 3 to 10 carbon atoms,
4) an aromatic hydrocarbon group having 6 to 14 carbon atoms,
5) an aralkyl group having 7 to 9 carbon atoms,
6) an amino group,
(7) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
8) an amidino group,
9) an acyl group having 2 to 8 carbon atoms,
10) a carbamoyl group,
11) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a sulfamoyl group,
13) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
14) a carboxyl group,
15) an alkoxycarbonyl group having 2 to 8 carbon atoms,
16) a hydroxy group,
17) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
18) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
19) a cycloalkyloxy group having 3 to 7 carbon atoms,
20) an aralkyloxy group having 7 to 9 carbon atoms,
21) an aryloxy group having 6 to 14 carbon atoms,
22) a thiol group,
23) a C 1-6 alkylthio group optionally substituted by 1 to 3 halogen atoms,
24) an aralkylthio group having 7 to 9 carbon atoms,
25) an arylthio group having 6 to 14 carbon atoms,
26) a sulfo group,
27) a cyano group,
28) an azide group,
29) a nitro group,
30) a nitroso group, and
31) a halogen atom;
X is a bond;
Q is an alkylene group having 1 to 20 carbon atoms;
Y is an oxygen atom;
ring A is a benzene ring optionally further having 1 to 3 substituents selected from the group consisting of
(1) an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have 1 to 3 substituents selected from the group consisting of
1) a cycloalkyl group having 3 to 10 carbon atoms,
2) an aryl group having 6 to 14 carbon atoms,
3) an aralkyl group having 7 to 9 carbon atoms,
4) an amino group,
5) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
6) an amidino group,
7) an acyl group having 2 to 8 carbon atoms,
8) a carbamoyl group,
9) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
10) a sulfamoyl group,
11) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a carboxyl group,
13) an alkoxycarbonyl group having 2 to 8 carbon atoms,
14) a hydroxy group,
15) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
16) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
17) a cycloalkyloxy group having 3 to 7 carbon atoms,
18) an aralkyloxy group having 7 to 9 carbon atoms,
19) an aryloxy group having 6 to 14 carbon atoms,
20) a thiol group,
21) a C 1-6 alkylthio group optionally substituted by 1 to 3 carbon atoms,
22) an aralkylthio group having 7 to 9 carbon atoms,
23) an arylthio group having 6 to 14 carbon atoms,
24) a sulfo group,
25) a cyano group,
26) an azide group,
27) a nitro group,
28) a nitroso group, and
29) a halogen atom,
(2) a hydroxy group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 1 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms, each of which group may have 1 to 2 substituents selected from the group consisting of a halogen atom and an alkoxy group having 1 to 3 carbon atoms,
(3) halogen atom,
(4) an acyl group which may have 1 to 3 substituents selected from the group consisting of a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, nitro, hydroxy, and amino,
(5) nitro group, and
(6) an amino group optionally mono- or di-substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, cycloalkenyl group having 3 to 10 carbon atoms, aryl group having 6 to 14 carbon atoms or acyl group having 1 to 13 carbon atoms;
Z is —(CH 2 ) n —O— (n is an integer of 1 to 8);
ring B is a pyridine ring which optionally further has 1 to 3 substituents selected from the group consisting of
(1) an aliphatic hydrocarbon group having 1 to 15 carbon atoms which may have 1 to 3 substituents selected from the group consisting of
1) a cycloalkyl group having 3 to 10 carbon atoms,
2) an aryl group having 6 to 14 carbon atoms,
3) an aralkyl group having 7 to 9 carbon atoms,
4) an amino group,
5) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
6) an amidino group,
7) an acyl group having 2 to 8 carbon atoms,
8) a carbamoyl group,
9) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
10) a sulfamoyl group,
11) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a carboxyl group,
13) an alkoxycarbonyl group having 2 to 8 carbon atoms,
14) a hydroxy group,
15) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
16) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
17) a cycloalkyloxy group having 3 to 7 carbon atoms,
18) an aralkyloxy group having 7 to 9 carbon atoms,
19) an aryloxy group having 6 to 14 carbon atoms,
20) a thiol group,
21) a C 1-6 alkylthio group optionally substituted by 1 to 3 carbon atoms,
22) an aralkylthio group having 7 to 9 carbon atoms,
23) an arylthio group having 6 to 14 carbon atoms,
24) a sulfo group,
25) a cyano group,
26) an azide group,
27) a nitro group,
28) a nitroso group, and
29) a halogen atom,
(2) an aromatic hydrocarbon group having 6 to 14 carbon atoms which may have 1 to 3 substituents selected from the group consisting of
1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms,
2) a C 2-6 alkenyl group optionally substituted by 1 to 3 halogen atoms,
3) a cycloalkyl group having 3 to 10 carbon atoms,
4) an aromatic hydrocarbon group having 6 to 14 carbon atoms,
5) an aralkyl group having 7 to 9 carbon atoms,
6) an amino group,
(7) an amino group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms or acyl group having 2 to 8 carbon atoms,
8) an amidino group,
9) an acyl group having 2 to 8 carbon atoms,
10) a carbamoyl group,
11) a carbamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
12) a sulfamoyl group,
13) a sulfamoyl group mono- or di-substituted by alkyl group having 1 to 4 carbon atoms,
14) a carboxyl group,
15) an alkoxycarbonyl group having 2 to 8 carbon atoms,
16) a hydroxy group,
17) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms,
18) a C 2-5 alkenyloxy group optionally substituted by 1 to 3 halogen atoms,
19) a cycloalkyloxy group having 3 to 7 carbon atoms,
20) an aralkyloxy group having 7 to 9 carbon atoms,
21) an aryloxy group having 6 to 14 carbon atoms,
22) a thiol group,
23) a C 1-6 alkylthio group optionally substituted by 1 to 3 halogen atoms,
24) an aralkylthio group having 7 to 9 carbon atoms,
25) an arylthio group having 6 to 14 carbon atoms,
26) a sulfo group,
27) a cyano group,
28) an azide group,
29) a nitro group,
30) a nitroso group, and
31) a halogen atom,
(3) a hydroxy group which is optionally substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, aralkyl group having 7 to 13 carbon atoms, acyl group having 1 to 13 carbon atoms or aryl group having 6 to 14 carbon atoms, each of which group may have 1 to 2 substituents selected from the group consisting of a halogen atom and an alkoxy group having 1 to 3 carbon atoms,
(4) halogen atom,
(5) an acyl group which may have 1 to 3 substituents selected from the group consisting of a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms, a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms, a halogen atom, nitro, hydroxy, and amino,
(6) nitro group, and
(7) an amino group optionally mono- or di-substituted by alkyl group having 1 to 10 carbon atoms, alkenyl group having 2 to 10 carbon atoms, cycloalkyl group having 3 to 10 carbon atoms, cycloalkenyl group having 3 to 10 carbon atoms, aryl group having 6 to 14 carbon atoms or acyl group having 1 to 13 carbon atoms;
U is a bond; and
W is an alkylene group having 1 to 20 carbon atoms;
or a salt thereof, which comprises subjecting a compound represented by the formula
wherein each symbol is as defined above, or a salt thereof, to a hydrolysis reaction in the presence of an acid or a base in an aqueous solvent.