15-PGDH inhibitor
A compound represented by general formula (1) or a pharmacologically acceptable salt thereof for inhibiting 15-PDGH.
1 . A compound of a formula selected from the group consisting of formula A1aa), formula A1ba), formula A2aa), formula A2ba), formula A2ca), formula A2da), formula A2ea), formula A3aa) and formula A3ba)
where Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
Q 5 is a methylene group, an oxygen atom, a sulfur atom or NR 7 group;
Q 6 is a single bond, a methylene group, an oxygen atom, a sulfur atom, a SO group, a SO 2 group, a methyleneoxy group or NR 7 group;
R 1 and R 2 are the same or different, and a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group or a C 3 -C 8 cycloalkyl group;
R 3 is a hydrogen atom, a C 1 -C 3 alkyl group or a C 1 -C 3 alkoxy group;
R 4 is a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group or a C 3 -C 8 cycloalkyl group;
R 7 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 8 and R 9 are the same or different, and a hydrogen atom or a C 1 -C 6 alkyl group optionally having at least one substituent selected from group D1;
when one of R 8 and R 9 is a hydrogen atom, the other is a C 1 -C 6 alkyl group having at least one substituent selected from group D1;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom, or a C 1 -C 3 alkyl group or a C 1 -C 3 alkoxy group, each optionally having at least one substituent selected from group D1;
NR 10 R 11 in —CONR 10 R 11 is a group selected from the group consisting of formulas B1) to B20),
R 14 , R 15 and R 16 are the same or different, and a hydrogen atom, a halogen atom, a hydroxy group, a carbonyl group, a carboxyl group, a C 1 -C 6 alkyl group, a halo C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a halo C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonylamino group, an aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups, or an amino group optionally having one or two C 1 -C 6 alkyl groups;
R 14 and R 15 are substituted optionally in any ring in the formula;
Y is a methylene group, an oxygen atom, a sulfur atom or a N—R 17 group;
R 17 is a hydrogen atom or a C 1 -C 3 alkyl group optionally having at least one substituent selected from group D;
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5;
each of q and r is 0, 1, 2 or 3;
G 1 is a group selected from the group consisting of formula G1a), formula G1b), formula G1c), formula G1d), formula G1e), formula G1f), formula G1g), formula G1h), formula G1i), formula G1j), formula G1k), formula G1l), formula G1m), formula G1n), formula G1o), formula G1p), formula G1q), formula G1r), formula G1s), formula G1t), formula G1u), formula G1v), formula G1w), formula G1x), formula G1y), formula G1z), formula G1A), formula G1B), formula G1C), formula G1D), formula G1E), formula G1F), formula G1G), formula G1H), formula G1I), formula G1J), formula G1K), formula G1L), formula G1M), formula G1N), formula G1O), formula G1P), formula G1Q), formula G1R), formula G1S) and formula G1T),
where R 18 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 19 is a hydrogen atom, a 3- to 8-membered heterocycloalkyl group containing an oxygen atom, or a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a phenyl group, a phenyl C 1 -C 3 alkyl group, a 6-membered aromatic heterocyclic group, a 6-membered aromatic heterocyclic C 1 -C 3 alkyl group, a C 1 -C 3 alkyl group, a halo C 1 -C 3 alkyl group or a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, each optionally having at least one substituent selected from group C;
R 20 is a hydrogen atom, a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a formyl group; or C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonylamino group, a C 1 -C 6 alkylsulfonyl group, a C 3 -C 8 cycloalkyl group, a 3- to 8-membered heterocycloalkylcarbonyl group, a 3- to 8-membered heterocycloalkylamino group or a 3- to 8-membered heterocycloalkylaminocarbonyl group, each optionally having at least one substituent selected from group A3; an aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups optionally having at least one substituent selected from group B1; or a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, each optionally having at least one substituent selected from group B1;
R 21 is a hydrogen atom, a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a formyl group; or a C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonylamino group, a C 1 -C 6 alkylsulfonyl group, a C 3 -C 8 cycloalkyl group, a 3- to 8-membered heterocycloalkylcarbonyl group, a 3- to 8-membered heterocycloalkylamino group or a 3- to 8-membered heterocycloalkylaminocarbonyl group, each optionally having at least one substituent selected from group B1; an amino group or an aminocarbonyl group, each optionally having one or two C 1 -C 6 alkyl groups optionally having, in an amino group, at least one substituent selected from group A3; or a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, each optionally having at least one substituent selected from group B1;
R 20 and R 21 are substituted optionally in any ring in the formula;
R 22 and R 23 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 24 is a hydrogen atom or a substituent selected from group B1;
X is —C(═O)—, —CH(OH)—, —S—, —SO— or —SO 2 —;
group A3 consists of a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a formyl group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group and a C 1 -C 6 alkylsulfonylamino group;
group B1 consists of a halogen atom, a hydroxy group, a carbonyl group, a carboxyl group, a C 1 -C 6 alkyl group, a halo C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a halo C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonylamino group, an aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups, an amino group optionally having one or two C 1 -C 6 alkyl groups, and a 3- to 8-membered heterocycloalkyl group;
group C consists of a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, an aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups, an amino group optionally having one or two C 1 -C 6 alkyl groups, and a 3- to 8-membered heterocycloalkyl group;
group D consists of a halogen atom, a hydroxy group, a carboxyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, an aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups, a C 1 -C 6 alkylsulfonyl group, an aminosulfonyl group optionally having one or two C 1 -C 6 alkyl groups, a C 1 -C 6 alkylsulfonylamino group, an amino group optionally having one or two C 1 -C 6 alkyl groups, and a 3- to 8-membered heterocycloalkyl group; and
group D1 consists of a halogen atom, a hydroxy group, a carboxyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group and a C 1 -C 6 alkoxycarbonyl group,
or a pharmacologically acceptable salt thereof.
2 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein G 1 is a group selected from the group consisting of formula G1aa), formula G1ba), formula G1ca), formula G1fa), formula G1ga), formula G1ha), formula G1ia), formula G1la), formula G1oa), formula G1pa), formula G1qa), formula G1va), formula G1wa), formula G1xa), formula G1ya) and formula G1Aa),
where R 19 is a hydrogen atom, a 3- to 8-membered heterocycloalkyl group containing an oxygen atom, or a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a phenyl group, a phenyl C 1 -C 3 alkyl group, a 6-membered aromatic heterocyclic group, a 6-membered aromatic heterocyclic C 1 -C 3 alkyl group, a C 1 -C 3 alkyl group, a halo C 1 -C 3 alkyl group or a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, each optionally having at least one substituent selected from group C;
R 20 is a hydrogen atom, a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a formyl group; or C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonylamino group, a C 1 -C 6 alkylsulfonyl group, a C 3 -C 8 cycloalkyl group, a 3- to 8-membered heterocycloalkylcarbonyl group, a 3- to 8-membered heterocycloalkylamino group or a 3- to 8-membered heterocycloalkylaminocarbonyl group, each optionally having at least one substituent selected from group A3; an aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups optionally having at least one substituent selected from group B1; or a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, each optionally having at least one substituent selected from group B1;
R 21 is a hydrogen atom, a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a formyl group; or a C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group, a C 1 -C 6 alkylsulfonylamino group, a C 1 -C 6 alkylsulfonyl group, a C 3 -C 8 cycloalkyl group, a 3- to 8-membered heterocycloalkylcarbonyl group, a 3- to 8-membered heterocycloalkylamino group or a 3- to 8-membered heterocycloalkylaminocarbonyl group, each optionally having at least one substituent selected from group B1; an amino group or an aminocarbonyl group, each optionally having one or two C 1 -C 6 alkyl groups optionally having, in an amino group, at least one substituent selected from group A3; or a 5-membered aromatic heterocyclic group or a 6-membered aromatic heterocyclic group, each optionally having at least one substituent selected from group B1; and
R 22 is a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group.
3 . The compound according to claim 2 , or a pharmacologically acceptable salt thereof, wherein NR 10 R 11 in —CONR 10 R 11 is a group selected from the group consisting of formula B1a), formula B2a), formula B4a), formula B5a), formula B7a), formula B8a), formula B9a), formula B10a), formula B11a), formula B13a) and formula B16a),
where R 14 and R 15 are the same or different, and a hydrogen atom, a halogen atom, a hydroxy group, a nitrile group, a carboxyl group, a C 1 -C 6 alkyl group, a C 1 -C 6 alkylcarbonyl group, a C 1 -C 6 alkoxy group, a C 1 -C 6 alkoxycarbonyl group or a halo C 1 -C 6 alkyl group;
R 14 and R 15 are substituted optionally in any ring in the formula B1a), formula B2a), formula B4a), formula B5a), formula B7a), formula B8a), formula B9a), formula B10a), formula B11a), formula B13a) and formula B16a); and
each of q and r is 0, 1, 2 or 3.
4 . The compound according to claim 3 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of a formula selected from the group consisting of formula A2aa), formula A2ba) and formula A3ba),
where Q 6 is a single bond, a methylene group, an oxygen atom, a methyleneoxy group or NR 7 group;
Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group or a halo C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
5 . The compound according to claim 4 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of a formula selected from the group consisting of formula A2aaa), formula A2baa), formula A2caa) and formula A2daa),
where G 1 is a group selected from the group consisting of formula G1aa), formula G1fa), formula G1ga), formula G1ia), formula G1pa), formula G1qa) and formula G1ya),
where Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
Q 6 is a single bond, a methylene group, an oxygen atom, or NR 7 group;
R 1 and R 2 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 3 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 4 is a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 14 and R 15 are the same or different, and a hydrogen atom, a fluorine atom, a chlorine atom, a C 1 -C 3 alkyl group or a halo C 1 -C 3 alkyl group;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 7 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 19 is a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a halo C 1 -C 3 alkyl group, a C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl group or a 3- to 8-membered heterocycloalkyl C 1 -C 3 alkyl group;
R 20 is a hydrogen atom, a halogen atom, a nitrile group, a carboxyl group, formyl group, a hydroxy C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group or a aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups;
R 21 is a hydrogen atom or a halogen atom;
R 22 is a hydrogen atom or a C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
6 . A method for treating at least one of fibrosis, cardiovascular diseases, and autoimmune diseases, comprising:
administering the compound of claim 1 or a pharmacologically acceptable salt thereof to a patient in need thereof.
7 . A method for treating at least one of fibrosis, cardiovascular diseases, and autoimmune diseases, comprising:
administering an effective amount of the compound of claim 2 or a pharmacologically acceptable salt thereof to a patient in need thereof.
8 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound having a structure selected from
9 . The compound according to claim 3 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of formula A2aa),
where Q 6 is a single bond, a methylene group, an oxygen atom, a methyleneoxy group or NR 7 group;
Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group or a halo C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
10 . The compound according to claim 3 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of formula A2ba),
where Q 6 is a single bond, a methylene group, an oxygen atom, a methyleneoxy group or NR 7 group;
Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy group or a halo C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
11 . The compound according to claim 4 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of formula A2aaa),
where G 1 is a group selected from the group consisting of formula G1aa), formula G1fa), formula G1ga), formula G1ia), formula G1pa), formula G1qa) and formula G1ya),
where Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
Q 6 is a single bond, a methylene group, an oxygen atom, or NR 7 group;
R 1 and R 2 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 3 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 4 is a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 14 and R 15 are the same or different, and a hydrogen atom, a fluorine atom, a chlorine atom, a C 1 -C 3 alkyl group or a halo C 1 -C 3 alkyl group;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 7 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 19 is a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a halo C 1 -C 3 alkyl group, a C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl group or a 3- to 8-membered heterocycloalkyl C 1 -C 3 alkyl group;
R 20 is a hydrogen atom, a halogen atom, a nitrile group, a carboxyl group, formyl group, a hydroxy C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group or a aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups;
R 21 is a hydrogen atom or a halogen atom;
R 2 is a hydrogen atom or a C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
12 . The compound according to claim 4 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of formula A2baa),
where G 1 is a group selected from the group consisting of formula G1aa), formula G1fa), formula G1ga), formula G1ia), formula G1pa), formula G1qa) and formula G1ya),
where Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
Q 6 is a single bond, a methylene group, an oxygen atom, or NR 7 group;
R 1 and R 2 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 3 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 4 is a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 14 and R 15 are the same or different, and a hydrogen atom, a fluorine atom, a chlorine atom, a C 1 -C 3 alkyl group or a halo C 1 -C 3 alkyl group;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 7 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 19 is a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a halo C 1 -C 3 alkyl group, a C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl group or a 3- to 8-membered heterocycloalkyl C 1 -C 3 alkyl group;
R 20 is a hydrogen atom, a halogen atom, a nitrile group, a carboxyl group, formyl group, a hydroxy C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group or a aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups;
R 21 is a hydrogen atom or a halogen atom;
R 22 is a hydrogen atom or a C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
13 . The compound according to claim 4 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of formula A2caa),
where G 1 is a group selected from the group consisting of formula G1 aa), formula G1fa), formula G1ga), formula G1ia), formula G1pa), formula G1qa) and formula G1ya),
where Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
Q 6 is a single bond, a methylene group, an oxygen atom, or NR 7 group;
R 1 and R 2 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 3 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 4 is a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 14 and R 15 are the same or different, and a hydrogen atom, a fluorine atom, a chlorine atom, a C 1 -C 3 alkyl group or a halo C 1 -C 3 alkyl group;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 7 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 19 is a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a halo C 1 -C 3 alkyl group, a C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl group or a 3- to 8-membered heterocycloalkyl C 1 -C 3 alkyl group;
R 20 is a hydrogen atom, a halogen atom, a nitrile group, a carboxyl group, formyl group, a hydroxy C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group or a aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups;
R 21 is a hydrogen atom or a halogen atom;
R 22 is a hydrogen atom or a C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
14 . The compound according to claim 4 , or a pharmacologically acceptable salt thereof, wherein the compound is a compound of formula A2daa),
where G 1 is a group selected from the group consisting of formula G1aa), formula G1fa), formula G1ga), formula G1ia), formula G1pa), formula G1qa) and formula G1ya),
where Q 3 is —(CH 2 ) m —(CR 5 R 6 ) n —(CH 2 ) p —;
Q 6 is a single bond, a methylene group, an oxygen atom, or NR 7 group;
R 1 and R 2 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 3 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 4 is a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 14 and R 15 are the same or different, and a hydrogen atom, a fluorine atom, a chlorine atom, a C 1 -C 3 alkyl group or a halo C 1 -C 3 alkyl group;
R 5 and R 6 are the same or different, and a hydrogen atom, a halogen atom or a C 1 -C 3 alkyl group;
R 7 is a hydrogen atom or a C 1 -C 3 alkyl group;
R 19 is a hydrogen atom, a C 1 -C 3 alkyl group, a C 1 -C 3 alkoxy C 1 -C 3 alkyl group, a C 3 -C 8 cycloalkyl group, a hydroxyl C 1 -C 6 alkyl group, a halo C 1 -C 3 alkyl group, a C 1 -C 6 alkoxycarbonyl C 1 -C 3 alkyl group or a 3- to 8-membered heterocycloalkyl C 1 -C 3 alkyl group;
R 20 is a hydrogen atom, a halogen atom, a nitrile group, a carboxyl group, formyl group, a hydroxy C 1 -C 6 alkyl group, a C 1 -C 6 alkoxycarbonyl group or a aminocarbonyl group optionally having one or two C 1 -C 6 alkyl groups;
R 21 is a hydrogen atom or a halogen atom;
R 22 is a hydrogen atom or a C 1 -C 3 alkyl group; and
each of m, n and p is 0, 1 or 2, and m+n+p is an integer of 2 to 5.
15 . A pharmaceutical composition for treating at least one of fibrosis, cardiovascular diseases, and autoimmune diseases, comprising:
the compound of claim 1 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
16 . A pharmaceutical composition for treating wounds, comprising:
the compound of claim 1 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
17 . A pharmaceutical composition for treating at least one of inflammatory diseases, graft-versus-host disease, hair growth, osteoporosis, hearing loss, tinnitus, dizziness, disequilibrium, glaucoma, dry eye, neutropenia, diabetes, underactive bladder, promotion of engraftment in stem cell or bone marrow transplantation or organ transplantation, neurogenesis and nerve cell death, muscle regeneration and cervical ripening, comprising:
the compound of claim 1 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
18 . A pharmaceutical composition for treating at least one of fibrosis, cardiovascular diseases and autoimmune diseases, comprising:
the compound of claim 2 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
19 . A pharmaceutical composition for treating wounds, comprising:
the compound of claim 2 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
20 . A pharmaceutical composition for treating at least one of inflammatory diseases, graft-versus-host disease, hair growth, osteoporosis, hearing loss, tinnitus, dizziness, disequilibrium, glaucoma, dry eye, neutropenia, diabetes, underactive bladder, promotion of engraftment in stem cell or bone marrow transplantation or organ transplantation, neurogenesis and nerve cell death, muscle regeneration and cervical ripening, comprising:
the compound of claim 2 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
21 . The compound according to claim 1 , or a pharmacologically acceptable salt thereof,
wherein the compound is a compound having a structure selected from the following structures:
22 . A pharmaceutical composition for treating at least one of fibrosis, cardiovascular diseases and autoimmune diseases, comprising:
the compound of claim 21 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
23 . A pharmaceutical composition for treating wounds, comprising:
the compound of claim 21 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.
24 . A pharmaceutical composition for treating at least one of inflammatory diseases, graft-versus-host disease, hair growth, osteoporosis, hearing loss, tinnitus, dizziness, disequilibrium, glaucoma, dry eye, neutropenia, diabetes, underactive bladder, promotion of engraftment in stem cell or bone marrow transplantation or organ transplantation, neurogenesis and nerve cell death, muscle regeneration and cervical ripening, comprising:
the compound of claim 21 or a pharmacologically acceptable salt thereof; and
a pharmacologically acceptable carrier.