Nitrogen-containing aromatic derivatives

1 . A compound (except N1-cyclopropyl-5-((2-(((2-chloroethylamino)carbonyl)amino)-4-pyridyl)oxy)-1H-1-indolecarboxamide) represented by the general formula:

wherein X 1 represents a nitrogen atom or a group represented by the formula —CR 10 ═, X 2 represents a nitrogen atom or a group represented by the formula —CR 11 ═, and X 1 and X 2 do not represent a nitrogen atom at the same time;

Y represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by the formula —NR Y —(wherein R Y represents a hydrogen atom or a C 1-6 alkyl group);

R 1 represents an optionally substituted C 1-6 alkoxy group, an optionally substituted C 6-10 aryloxy group, a group represented by the formula —NR 12a R 12b , a group represented by the formula:

(wherein Y A1 and Y A2 each independently represent a group represented by the formula -A 10 -A 11 -A 12 (wherein A 10 represents a single bond or an optionally substituted C1-6 alkylene; A 11 represents a single bond, an oxygen atom, a carbonyl group or a sulfonyl group; and A 12 represents a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-8 cycloalkyl group, a C 6-10 aryl group, a 5- to 10- membered heteroaryl group, a group represented by the formula —NR A10 R A11 , a group represented by the formula —OR A12 (wherein R A10 , R A11 and R A12 each independently represent a hydrogen atom, a C1-6 alkyl group or C 3-8 cycloalkyl group) or a group represented by the formula:

(wherein e represents 1 or 2; Z represents an oxygen atom, a group represented by the formula —CR X7 R X8 — or a group represented by the formula —NR X9 —; R X7 , R X8 and R X9 each independently represent a hydrogen atom, a hydroxyl group or a C 1-6 alkyl group)); and Y A3 represents a hydrogen atom or an optionally substituted C 1-6 alkyl group) or a group represented by the formula:

(wherein T1 represents an optionally substituted 5- to 10- membered aromatic heterocycle which may have X in the ring or an optionally substituted 3- to 10- membered heterocycle which may have X in the ring);

R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 10 and R 11 each independently represent a hydrogen atom, a halogen atom, a cyano group, an optionally substituted C 1-6 alkyl group, an optionally substituted C 2-6 alkenyl group, an optionally substituted C 2-6 alkynyl group, an optionally substituted C 3-8 cycloalkyl group, a group represented by the formula —CO—R 13 , a group represented by the formula —NR 14 —CO—R 13 , a group represented by the formula —SO 2 —R 15 , a group represented by the formula —NR 14 —SO 2 —R 15 , or a group represented by the formula —NR 16a R 16b ;

R 9 represents a group represented by the formula —NR 16a R 16b or a group represented by the formula:

(wherein T2 represents an optionally substituted 5- to 10- membered aromatic heterocycle or an optionally substituted 3- to 10- membered heterocycle);

R 12a and R 12b each independently represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, an optionally substituted C 3-6 alkenyl group, an optionally substituted C 3-6 alkynyl group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted 3- to 10- membered heterocyclic group, or an optionally substituted C 1-6 alkoxy group;

R 13 represents a hydrogen atom, an optionally substituted C 1-6 alkyl group, an optionally substituted C 2-6 alkenyl group, an optionally substituted C 2-6 alkynyl group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 6-10 aryl group, an optionally substituted 5- to 10- membered heteroaryl group, an optionally substituted 3- to 10- membered heterocyclic group, an optionally substituted C 1-6 alkoxy group, an optionally substituted C 6-10 aryloxy group, a group represented by the formula —NR 12a R 12b , or a group represented by the formula:

(wherein T2 represents an optionally substituted 5- to 10- membered aromatic heterocycle or an optionally substituted 3- to 10- membered heterocycle);

R 2 and R 14 each independently represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, an optionally substituted C 2-6 alkenyl group, an optionally substituted C 2-6 alkynyl group, an optionally substituted C 3-8 cycloalkyl group, or a group represented by the formula —CO—R 13 ;

R 15 represents an optionally substituted C 1-6 alkyl group, an optionally substituted C 2-6 alkenyl group, an optionally substituted C 2-6 alkynyl group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 6-10 aryl group, an optionally substituted 5- to 10- membered heteroaryl group, or an optionally substituted 3- to 10- membered heterocyclic group;

R 16a and R 16b each independently represent a hydrogen atom, an optionally substituted C 1-6 alkyl group, an optionally substituted C 3-6 alkenyl group, an optionally substituted C 3-6 alkynyl group, an optionally substituted C 3-8 cycloalkyl group, an optionally substituted C 6-10 aryl group, an optionally substituted 5- to 10- membered heteroaryl group, an optionally substituted 3- to 10-membered heterocyclic group, or an optionally substituted C 1-6 alkoxy group; and

X represents an oxygen atom, a sulfur atom, a carbonyl group, a sulfonyl group, a group represented by the formula —CR X1 R X2 —, or a group represented by the formula —NR X3 — (wherein R X1 , R X2 and R X3 each independently represent a hydrogen atom or a group represented by the formula -A 1 -A 2 -A 3 (wherein A 1 and A 2 each independently represent a single bond, an optionally substituted C 1-6 alkylene group or a carbonyl group; and A 3 represents a hydrogen atom, a C 3-8 cycloalkyl group, a group represented by the formula —NR A1 R A2 , or the formula —OR A3 (wherein, R A1 , R A2 and R A3 each independently represent a hydrogen atom or a C 1-6 alkyl group), or an optionally substituted group represented by the formula:

(wherein a represents 1 or 2))),

a salt thereof, or a hydrate of the foregoing.

2 . The compound of claim 1 (except N1-cyclopropyl-5-((2-(((2-chloroethylamino)carbonyl)amino)-4-pyridyl)oxy)-1H-1-indolecarboxamide) represented by the general formula:

wherein X 1 , X 2 , Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 represent the same definitions as X 1 , X 2 , Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 and R 9 in claim 1 , respectively, a salt thereof, or a hydrate of the foregoing.

3 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein Y represents an oxygen atom, a group represented by the formula —NH—, or a group represented by the formula —N(CH 3 )—.

4 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein Y represents an oxygen atom.

5 . The compound according to any of claims 1 , a salt of the compound, or a hydrate of the foregoing, wherein one of X 1 and X 2 represents a group represented by the formula —CH═ and the other represents a nitrogen atom.

6 . The compound according to any of claims 1 a salt of the compound, or a hydrate of the foregoing, wherein both X 1 and X 2 represent a group represented by the formula —CH═.

7 . The compound according to any of claims 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 3 , R 4 , R 5 , R 6 and R 8 each represent a hydrogen atom, and R 7 represents a hydrogen atom, a halogen atom or an optionally substituted C 1-6 alkyl group.

8 . The compound according to any of claims 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 9 represents a group represented by the formula —NHR 17 (wherein R 17 represents an optionally substituted C 1-6 alkyl group, a C 3-6 alkynyl group, a C 3-8 cycloalkyl group, an optionally substituted C 6-10 aryl group or an optionally substituted 5- to 10- membered heteroaryl group).

9 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 9 represents a group represented by the formula —NR 18a R 18b (wherein R 18a and R 18b each independently represent a C 1-6 alkyl group).

10 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 9 represents a group represented by the formula:

(wherein b 1 represents 1 or 2; X represents the same definition as X in claim 1) .

11 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 9 represents a group represented by the formula —NHR 19 (wherein R 19 represents a C 1-6 alkyl group, a C 3-6 alkynyl group, a C 3-8 cycloalkyl group or a C 6-10 aryl group).

12 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 3 , R 4 , R 5 , R 6 , R 7 and R 8 each represent a hydrogen atom.

13 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 2 represents a hydrogen atom.

14 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 9 represents a group represented by the formula —NHR 20 (wherein R 20 represents a methyl group, an ethyl group or a cyclopropyl group).

15 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 9 represents a group represented by the formula —NH(CH 3 ).

16 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a further optionally substituted group represented by the formula:

(wherein b 2 represents 0, 1 or 2; and X represents the same definition as X in claim 1) .

17 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formula:

(wherein X represents the same definition as X in claim 1) .

18 . The compound according to claim 17 , a salt of the compound, or a hydrate of the foregoing, wherein X in the formula (IV) represents an oxygen atom.

19 . The compound according to claim 17 , a salt of the compound, or a hydrate of the foregoing, wherein X in the formula (IV) represents a group represented by the formula:

(wherein R X4 represents a hydrogen atom or a group represented by the formula -A 4 -A 5 -A 6 (wherein A 4 and A 5 each independently represent a single bond, an optionally substituted C 1-6 alkylene or a carbonyl group; and A, represents a hydrogen atom, a C 3-8 cycloalkyl group or a group represented by the formula —NR A4 R A5 or the formula —OR A6 (wherein R A4 , R A5 and R A6 each independently represent a hydrogen atom or a C 1-6 alkyl group))).

20 . The compound according to claim 17 , a salt of the compound, or a hydrate of the foregoing, wherein X in the formula (IV) represents a group represented by the formula:

(wherein R X5 and R X6 each independently represent a hydrogen atom or a group represented by the formula -A 7 -A 8 -A 9 (wherein A 7 and A 8 each independently represent a single bond, an optionally substituted C 1-6 alkylene group or a carbonyl group; and A 9 represents a hydrogen atom, a C 3-8 cycloalkyl group, a group represented by the formula —NR A7 R A8 , or the formula —OR A9 (wherein R A7 , R A8 , and R A9 each independently represent a hydrogen atom or a C 1-6 alkyl group), or a group represented by the formula:

(wherein c 1 represents 0, 1 or 2))).

21 . The compound according to claim 20 , a salt of the compound, or a hydrate of the foregoing, wherein one of R X5 and R X6 in the formula (VI) represents a hydroxyl group and the other represents a hydrogen atom or a C 1-6 alkyl group.

22 . The compound according to claim 20 , a salt of the compound, or a hydrate of the foregoing, wherein one of R X5 or R X6 in the formula (VI) represents a hydrogen atom and the other represents a group represented by the formula:

(wherein c 2 represents 1 or 2).

23 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formula:

(wherein R X51 and R X61 each independently represent a hydrogen atom or a group represented by the formula -A 71 -A 81 -A 91 (wherein A 71 and A 81 each independently represent a single bond, an optionally substituted C 1-6 alkylene group or a carbonyl group; and A 91 represents a hydrogen atom, a C 3-8 cycloalkyl group, a group represented by the formula —NR A71 R A81 , or the formula —OR A91 (wherein R A71 , R A81 , and R A91 each independently represent a hydrogen atom or a C 1-6 alkyl group), or a group represented by the formula:

(wherein c 11 represents 0, 1 or 2))).

24 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formula:

(wherein Y A1 and Y A2 each independently represent a group represented by the formula -A 10 -A 11 -A 12 (wherein A 10 represents a single bond or an optionally substituted C 1-6 alkylene group; A 11 represents a single bond, an oxygen atom, a carbonyl group, or a sulfonyl group; and A 12 represents a hydrogen atom, a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 2-6 alkynyl group, a C 3-8 cycloalkyl group, a C 6-10 aryl group, a 5- to 10- membered heteroaryl group, a group represented by the formula —NR A10 R A11 , or the formula —OR A12 (wherein, R A10 , R A11 and R A12 each independently represent a hydrogen atom, a C 1-6 alkyl group or a C 3-8 cycloalkyl group), or a group represented by the formula:

(wherein e represents 1 or 2; and Z represents an oxygen atom or a group represented by the formula —CR X7 R X8 — or the formula —NR X9 — (wherein R X7 , R X8 and R X9 each independently represent a hydrogen atom, a hydroxyl group or a C 1-6 alkyl group))); and Y A3 represents a hydrogen atom or an optionally substituted C 1-6 alkyl group).

25 . The compound according to claim 24 , a salt of the compound, or a hydrate of the foregoing, wherein one of Y A1 and Y A2 in the formula (VIII) represents a hydrogen atom and the other represents a group represented by the formula —(CH 2 ) 2 -A 13 -A 14 (wherein A 13 represents a single bond, a carbonyl group or a sulfonyl group; and A 14 represents a C 1-6 alkyl group, a group represented by the formula —NR A13 R A14 (wherein R A13 and R A14 each independently represent a hydrogen atom, a C 1-6 alkyl group or a C 3-8 cycloalkyl group), or a group represented by the formula:

(wherein e and Z represent the same definitions as e and Z in claim 24 , respectively)); and Y A3 in the formula (VIII) represents a hydrogen atom.

26 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formulas:

(each of the foregoing members being optionally substituted with a group selected from Substituent Group Alpha,

wherein Substituent Group Alpha is a group consisting of a halogen atom, a hydroxyl group, a thiol group, a nitro group, a cyano group, a carboxyl group, an amino group, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, and a group represented by the formulas:

(wherein R N1 and R N2 each independently represent a hydrogen atom or a C 1-6 alkyl group)).

27 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formulas:

28 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formulas:

29 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein R 1 represents a group represented by the formulas:

30 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein the compound is represented by the general formula:

(wherein R 1 represents a group represented by the formulas:

(each of the foregoing members being optionally substituted with a group selected from Substituent Group Beta,

wherein Substituent Group Beta is a group consisting of a hydroxyl group, a C 1-6 alkyl group, a C 3-8 cycloalkyl group, and a group represented by the formulas:

(wherein R N1 and R N2 each independently represent a hydrogen atom or a C 1-6 alkyl group)); and

R 9 represents a group represented by the formula —NHR 20 (wherein R 20 represents a methyl group, an ethyl group or a cyclopropyl group)).

31 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein the compound is a compound selected from a group consisting of

(1) N1-ethyl-5-(2-((methoxylamino)carbonyl)amino-4-pyrimidyl)oxy-1H-indolecarboxamide;

(2) 5-(6-(3-(3-diethylaminopropylamino)ureido)pyrimidin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(3) 5-(6-(((4-hydroxypiperidin-1-yl)carbonyl)amino)-pyrimidin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(4) 5-(6-((4-pyrrolidin-1-yl)piperidin-1-yl)carbonylamino)pyrimidin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(5) 5-(2-(3-((1R)-1-carbamoyl-2-phenylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(6) 5-(2-(3-((1S)-1-carbamoyl-2-phenylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(7) 5-(2-(3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(8) 5-(2-(3-(2-(4-hydroxy-4-methylpiperidin-1-yl)-2-oxoethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(9) 5-(2-(3-((1S)-1-carbamoylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methyl amide;

(10) 5-(2-(3-((1S)-1-carbamoyl-3-methylbutyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(11) 5-(2-(3-carbamoylmethylureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methyl amide;

(12) 5-(2-(3-cyclopropylcarbamoylmethylureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(13) 5-(2-(3-((1 S)-1-carbamoyl-2-hydroxyethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(14) 5-(2-(3-((1R)-1-carbamoyl-2-hydroxyethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(15) (2S)-2-(3-(4-(1-methylcarbamoyl-1H-indol-5-yloxy)pyridin-2-yl)ureido)-1,5-pentanedicarboxylic acid diamide;

(16) (2S)-2-(3-(4-(1-methylcarbamoyl-1H-indol-5-yloxy)pyridin-2-yl)ureido)succinamide;

(17) 5-(2-(3-((1S)-1-cyclopropylcarbamoyl-2-hydroxyethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(18) 5-(2-(3-((1S)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(19) 5-(2-(3-((1R)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(20) 5-(2-(3-((1S)-1-hydroxymethyl-2-oxo-2-piperidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(21) 5-(2-(3-((1R)-1-hydroxymethyl-2-oxo-2-piperidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(22) 5-(2-(3-((1S)-1-hydroxymethyl-2-(4-hydroxypiperidin-1-yl)-2-oxoethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(23) 5-(2-(3-((1S)-1-hydroxymethyl-2-(morpholin-4-yl)-2-oxoethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(24) 5-(2-(3-(2-cyclopropylcarbamoylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(25) 5-(2-(3-(3-oxo-3-(pyrrolidin-1-yl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(26) 5-(2-(3-(3-(4-hydroxy-4-methylpiperidin-1-yl)-3-oxopropyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(27) N1-ethyl-5-(2-(((2-ethoxyethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(28) N1-methyl-5-(2-((4-(2-hydroxy-2-methylpropionyl)piperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(29) N1-methyl-5-(2-((3-(diethylamino)propylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(30) N1-methyl-5-(2-(((3-(4-hydroxypiperidino)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(31) N1-methyl-5-(2-(((3-(4-methylpiperazin-1-yl)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(32) 5-(2-(3-(4-oxo-4-(pyrrolidin-1-yl)butyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(33) 5-(2-(3-(3-(cyclopropylcarbamoyl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(34) 5-(2-(3-(4-(4-hydroxy-4-methylpiperidin-1-yl)-4-oxobutyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(35) 5-(2-(3-(3-(diethylcarbamoyl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(36) 5-(2-(3-(3-(methylcarbamoyl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(37) N1-methyl-5-(2-(pyrrolidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(38) N1-methyl-5-(2-(piperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(39) N1-methyl-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(40) N1-methyl-5-(2-(4-oxopiperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(41) 5-(2-(((4-hydroxy-4-methylpiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(42) N1-methyl-5-(2-((4-(1-hydroxy-1-methylethyl)piperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(43) 5-(2-(((4-(3-methylcarbamoylpropyl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(44) 5-(2-(((4-(3-carbamoylpropyl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(45) 5-(2-((4-((pyrrolidin-1-yl)carbonyl)piperidin-1-yl)carbonylamino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(46) N 1-methyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(47) N1-methyl-5-(2-(((4-(piperidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(48) N1-methyl-5-(2-((4-ethylpiperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(49) N1-methyl-5-(2-((4-(2-hydroxyethyl)piperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(50) N1-methyl-5-(2-((3-methylsulfonylpropylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(51) N1-methyl-5-(2-((4-(2-dimethylaminoacetyl)piperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(52) N1-methyl-5-(2-((4-cyclohexylpiperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(53) N4-(4-(1-(methylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(54) N1-methyl-5-(2-((1,1-dioxothiomorpholin-4-ylcarbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(55) 5-(2-(3-((1R)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(56) 5-(2-(3-((1S)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(57) 5-(2-(3-((1R)-1-hydroxymethyl-2-oxo-2-piperidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(58) 5-(2-(3-((1S)-1-hydroxymethyl-2-oxo-2-piperidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(59) 5-(2-(3-(2-(4-hydroxy-4-methylpiperidin-1-yl)-2-oxoethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(60) N 1-ethyl-5-(2-((((1-methyl-4-piperidyl)methyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(61) N1-ethyl-5-(2-(((2-diethylamino)ethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(62) N1-ethyl-5-(2-(((2-(morpholin-4-yl)ethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(63) N1-ethyl-5-(2-(((2-(4-hydroxypiperidino)ethyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(64) N1-methyl-5-(2-(((2-(4-hydroxypiperidino)ethyl)amino)carbonyl)amino-4-pyridyl)oxy-H-1-indolecarboxamide;

(65) N1-ethyl-5-(2-((3-(diethylamino)propylamino)carbonyl)amino-4-pyridyl)oxy-1-indolecarboxamide;

(66) N1-ethyl-5-(2-(((3-(morpholin-4-yl)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(67) N1-ethyl-5-(2-(((3-(4-methylpiperazin-1-yl)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(68) N 1-cyclopropyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(69) 5-(2-(3-((1R)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopropylamide;

(70) 5-(2-(3-((1S)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopropylamide;

(71) 5-(2-(3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopropylamide;

(72) 5-(2-(3-(3-oxo-3-(pyrrolidin-1-yl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopropylamide;

(73) 5-(2-(3-((1R)-1-hydroxymethyl-2-oxo-2-piperidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopropylamide;

(74) 5-(2-(3-((1 S)-1-hydroxymethyl-2-oxo-2-piperidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopropylamide;

(75) N1-phenyl-5-(2-(((3-(diethylamino)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(76) N1-phenyl-5-(2-(((3-(4-methylpiperazin-1-yl)propyl)amino)carbonyl)amino-4-pyridyl)oxy- 1H-1-indolecarboxamide;

(77) N1-ethyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(78) 5-(2-(((4-hydroxy-4-methylpiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(79) N1-ethyl-5-(2-((4-hydroxypiperidin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(80) N1-ethyl-5-(2-(piperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(81) N1-ethyl-5-((2-((pyrrolidin-1-ylcarbonyl)amino)-4-pyridyl)oxy)-1H-1-indolecarboxamide;

(82) N4-(4-((1-(ethylamino)carbonyl-1H-5-indolyl)oxy)-2-pyridyl)-4-morpholinecarboxamide;

(83) N1-ethyl-5-(2-((1,1-dioxothiomorpholin-4-ylcarbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(84) N1-ethyl-5-(2-((methoxylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(85) N1-cyclopropyl-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(86) N1-cyclopropyl-5-(2-(((4-hydroxy-4-methylpiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarbox-amide;

(87) N4-(4-(1-(cyclopropylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(88) N1-cyclopropyl-5-(2-((pyrrolidin-1-ylcarbonyl)amino)-4-pyridyl)oxy-1H-1-indolecarboxamide;

(89) N1-cyclopropyl-5-(2-(piperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(90) N4-(4-(1-(cyclopentylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(91) 5-(2-(((4-hydroxypiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid cyclopentylamide;

(92) N1-cyclopentyl-5-(2-((4-(pyrrolidin-1-yl)piperidin-1-ylcarbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(93) N1-(3-methylbutyl)-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(94) N -(3-methylbutyl)-5-(2-((4-(hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(95) N4-(4-(1-((3-methylbutyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(96) N1-(1-ethylpropyl)-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(97) N1-(1-ethylpropyl)-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(98) N4-(4-(1-((1-ethylpropyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl) 4 -morpholinecarboxamide;

(99) N4-(4-(1-((1-pentyl)amino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(100) N1-(1-pentyl)-5-(2-(((4-hydroxypiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(101) N1-(1-pentyl)-5-(2-((4-(pyrrolidin-1-yl)piperidin-1-ylcarbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(102) N1-methyl-3-chloro-5-(2-(((3-(diethylamino)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(103) N1-methyl-3-chloro-5-(2-((4-(pyrrolidin-1-yl)piperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(104) N1-methyl-3-chloro-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(105) N1-methyl-3-chloro-5-(2-(((3-(4-hydroxypiperidino)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(106) N1-methyl-3-chloro-5-(2-((4-(2-hydroxyethyl)piperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(107) N4-(4-(3-chloro-1-(methylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(108) N1-methyl-3-chloro-5-(2-((4-(ethylpiperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(109) N1-ethyl-3-chloro-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(110) N1-ethyl-3-chloro-5-(2-(((3-(4-hydroxypiperidino)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(111) N1-ethyl-3-chloro-5-(2-(((3-(diethylamino)propyl)amino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(112) N1,3-dimethyl-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(113) N1,3-dimethyl-5-(2-((4-(pyrrolidin-1-yl)piperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(114) N1-cylopropyl-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-3-methyl-1H-1-indolecarboxamide;

(115) N1-cylopropyl-5-(2-((4-(2-hydroxyethyl)piperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-3-methyl-1H-1-indolecarboxamide;

(116) N1-methyl-5-(2-((methylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(117) N1-methyl-5-(2-((diethylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(118) N1-(2-propynyl)-5-(2-((pyrrolidin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(119) N1-methyl-5-(2-(azetidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(120) N1-ethyl-5-(2-(azetidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(121) N1-cyclopropyl-5-(2-(azetidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(122) N1-methyl-5-(2-(((4-(morpholin-4-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(123) N1-methyl-5-(2-(((4-(azetidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(124) N1-methyl-5-(2-(((4-(diethylamino)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(125) N1-methyl-5-(2-(((4-(4-hydroxypiperidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide; and

(126) N1-propyl-5-(2-(pyrrolidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide.

32 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein the compound is a compound selected from a group consisting of

(1) 5-(2-(3-(2-oxo-2-(pyrrolidin-1-yl)ethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(2) 5-(2-(3-carbamoylmethylureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(3) 5-(2-(3-((1S)-1-hydroxymethyl-2-oxo-2-pyrrolidin-1-ylethyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(4) N1-methyl-5-(2-((4-(2-hydroxy-2-methylpropionyl)piperazin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(5) 5-(2-(3-(4-oxo-4-(pyrrolidin-1-yl)butyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(6) 5-(2-(3-(3-(cyclopropylcarbamoyl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(7) 5-(2-(3-(4-(4-hydroxy-4-methylpiperidin-1-yl)-4-oxobutyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(8) 5-(2-(3-(3-(methylcarbamoyl)propyl)ureido)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(9) N1-methyl-5-(2-(pyrrolidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(10) N1-methyl-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(11) N1-methyl-5-(2-(4-oxopiperidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(12) 5-(2-(((4-hydroxy-4-methylpiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(13) 5-(2-(((4-(3-methylcarbamoylpropyl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(14) 5-(2-(((4-(3-carbamoylpropyl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(15) N1-methyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(16) N1-methyl-5-(2-(((4-(piperidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(17) N 1-methyl-5-(2-((3-methylsulfonylpropylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(18) N4-(4-(1-(methylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide;

(19) N1-cyclopropyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(20) 5-(2-(((4-hydroxy-4-methylpiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid ethylamide;

(21) N1-ethyl-5-(2-((4-hydroxypiperidin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(22) N1-ethyl-5-((2-((pyrrolidin-1-ylcarbonyl)amino)-4-pyridyl)oxy)-1H-1-indolecarboxamide;

(23) N4-(4-((1-(ethylamino)carbonyl-1H-5-indolyl)oxy)-2-pyridyl)-4-morpholinecarboxamide;

(24) N1-cyclopropyl-5-(2-((pyrrolidin-1-ylcarbonyl)amino)-4-pyridyl)oxy-1H-1-indolecarboxamide;

(25) N1-methyl-3-chloro-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(26) N1-methyl-5-(2-((methylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(27) N1-methyl-5-(2-((diethylamino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(28) N1-(2-propynyl)-5-(2-((pyrrolidin-1-yl)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(29) N1-methyl-5-(2-(azetidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(30) N1-ethyl-5-(2-(azetidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(31) N1-cyclopropyl-5-(2-(azetidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(32) N1-methyl-5-(2-(((4-(morpholin-4-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(33) N1-methyl-5-(2-(((4-(azetidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(34) N1-methyl-5-(2-(((4-(diethylamino)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(35) N1-methyl-5-(2-(((4-(4-hydroxypiperidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide; and

(36) N1-propyl-5-(2-(pyrrolidin-1-ylcarbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide.

33 . The compound according to claim 1 , a salt of the compound, or a hydrate of the foregoing, wherein the compound is a compound selected from a group consisting of

(1) 5-(2-(((4-hydroxy-4-methylpiperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-indole-1-carboxylic acid methylamide;

(2) N1-methyl-5-(2-((4-hydroxypiperidino)carbonyl)amino-4-pyridyl)oxy-1H-1-indolecarboxamide;

(3) N1-methyl-5-(2-(((4-(pyrrolidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide;

(4) N1-methyl-5-(2-(((4-(piperidin-1-yl)piperidin-1-yl)carbonyl)amino)pyridin-4-yloxy)-1H-1-indolecarboxamide; and

(5) N4-(4-(1-(methylamino)carbonyl-1H-5-indolyl)oxy-2-pyridyl)-4-morpholinecarboxamide.

34 . A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutical adjuvant.

35 . A prophylactic or therapeutic agent for a disease for which angiogenesis inhibition is effective, comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

36 . An angiogenesis inhibitor comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

37 . An antitumor agent comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

38 . The antitumor agent according to claim 37 , wherein the tumor is a pancreatic cancer, a gastric cancer, a colon cancer, a breast cancer, a prostate cancer, a lung cancer, a renal cancer, a brain tumor, a blood cancer or an ovarian cancer.

39 . A therapeutic agent for hemangioma comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

40 . A cancer metastasis inhibitor comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

41 . A therapeutic agent for retinal neovascularization or diabetic retinopathy comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

42 . A therapeutic agent for an inflammatory disease comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

43 . The therapeutic agent for an inflammatory disease according to claim 42 , wherein the inflammatory disease is deformant arthritis, rheumatoid arthritis, psoriasis or delayed hypersensitivity reaction.

44 . A therapeutic agent for atherosclerosis comprising as an active ingredient, a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

45 . A prophylactic or therapeutic method for a disease for which angiogenesis inhibition is effective, comprising administering to a patient, a pharmacologically effective dose of a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing.

46 . Use of a compound according to claim 1 , a salt thereof, or a hydrate of the foregoing for the manufacture of a prophylactic or therapeutic agent for a disease for which angiogenesis inhibition is effective.