# US 2014/0155398 A1 · Heterocyclic compounds as protein kinase inhibitors

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- Number: US 2014/0155398 A1
- Document ID: US20140155398A1
- Status: Published application
- Kind: A1
- Application number: 14/088,093
- Filed: 2013-11-22
- Published: 2014-06-05
- Earliest claimed: 2011-05-26
- Assignees: Daiichi Sankyo Company, Limited
- Applicants: Daiichi Sankyo Company, Limited
- Inventors: Ashwani Kumar Verma; Kumaragurubaran Nagaswamy; Lalima Sharma; Soma Ghosh; Balkrishna Ramchandra Kale; Aniruddha Mondal; Punit Kumar Srivastava; Sunanda Ghosh Dastidar; Rijwan Jaffer Momin; Pradip Balu Wagh; Sonali Nanasaheb Pansare; Pramod Raosaheb Markad; Yogesh Balasaheb Khairnar; Rie Miyauchi; Takeshi Murata; Masayuki Ishizaki; Masatoshi Nagamochi; Shin Iimura
- Web page: https://patentgrep.com/patent/US20140155398A1

## CPC

- A61K 31/437: the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
- A61K 31/506: not condensed and containing further heterocyclic rings
- A61K 31/5377: not condensed and containing further heterocyclic rings, e.g. timolol
- A61P 1/00: Drugs for disorders of the alimentary tract or the digestive system
- A61P 11/00: Drugs for disorders of the respiratory system
- A61P 17/06: Antipsoriatics
- A61P 19/00: Drugs for skeletal disorders
- A61P 19/02: for joint disorders, e.g. arthritis, arthrosis
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 29/00: Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P 35/00: Antineoplastic agents
- A61P 37/00: Drugs for immunological or allergic disorders
- A61P 37/06: Immunosuppressants, e.g. drugs for graft rejection
- A61P 43/00: Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C07D 471/04: Ortho-condensed systems
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention provides a heterocyclic compound of formula (I), a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof, wherein A, A′ B, D, R1, R2 and R3 are as defined herein, a pharmaceutical composition comprising a compound of formula (I) as an active ingredient, methods of production, and methods of use thereof. Particularly, the present invention provides a compound of formula (I) useful for treating or preventing a disease, condition or disorder associated with protein kinases, preferably Janus Kinase family.

## Claims

### Claim 1

A compound having the structure of formula (I),
a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof, wherein:
A and B independently represent N or CR, with the proviso that both A and B are not N;
R, R′ and R″ independently represent H, (C1-C6) alkyl, halogen, —CN, —NRaRb, —NRaCORb or —CONRaRb, with the proviso that R′ represents H, halogen or —NRaCORb when A is N and R″ represents H, halogen or —NRaCORb when B is N;
R1 represents H, (C1-C3) alkyl or —COR4;
R2 represents H, (C1-C3) alkyl, halo or —CN;
R3 represents H, (C1-C3) alkyl, halo, —CN or —COR4;
R4 represents optionally substituted phenyl, with the proviso that R1 represents —COR4 when A is N and R3 represents —COR4 when B is N;
Ra and Rb independently represent H, (C1-C8) alkyl, (C3-C8) cycloalkyl or OR′″;
Ra and Rb are taken together with the N atom to which they are attached to form 3-8 membered heterocyclyl, optionally containing additional heteroatom(s) selected from N, O or S, wherein heterocyclyl is optionally substituted; and
R′″ represents H or (C1-C3) alkyl.

### Claim 2 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein A represents N, R′ represents H or —NRaCORb and R1 represents —COR4.

### Claim 3 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein A represents N, R′ represents —NRaCORb and R1 represents —COR4.

### Claim 4 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein B represents N, R″ represents H or —NRaCORb and R3 represents —COR4.

### Claim 5 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein B represents N, R″ represents —NRaCORb and R3 represents —COR4.

### Claim 6 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein R1 represents H or (C1-C3) alkyl and R3 represents —COR4.

### Claim 7 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein R1 represents —COR4 and R3 represents H, (C1-C3) alkyl, halo or —CN.

### Claim 8 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein Ra represents H or (C1-C3) alkyl and Rb represents H, (C1-C3) alkyl, (C1-C3) alkoxy or (C3-C5) cycloalkyl.

### Claim 9 (depends on 1)

The compound, a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof according to claim 1, wherein R4 represents a group selected from:
wherein:
R7, R8 and R9 independently represent H, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxy, halo, —NO2, —(CH2)qC(O)NRcRd, —(CH2)qNRcCORd, —(CH2)qNRcCONRcRd, —(CH2)qNRcC(O)ORd, —(CH2)qNRcRd, —(CH═CH)—(CH2)sC(O)ORe, —(CH═CH)—(CH2)sCONRcRd, —(CH═CH)—(CH2)sCN, —(CH═CH)4−CH2)sRe, —(CH2)sC(O)ORe, —(CH)rCN, —(CH2)rORe, —(CH2)rRe, —(CH2)rC(O)ORe, —(CH)rhalo, —S(O)pRe, —S(O)pNRcRd, —NRcS(O)pRd, and wherein alkyl, alkenyl, alkynyl, cycloalkyl, aryl, heteroaryl heterocyclyl are optionally substituted;
Rc and Rd independently represent H, (C1-C8) alkyl, (C3-C8) cycloalkyl, aryl, aralkyl, heteroaryl, heteroarylalkyl, —(CH2)rORe, —(CH2)rSRe, —(CH2)rCN, —(CH2)rhalo, —(CH2)rC(O)ORe, —(CH2)rNRcRd, —CORe, —S(O)pRe or —(CH2)rRe, wherein alkyl, cycloalkyl, aryl and heteroaryl are optionally substituted;
Rc and Rd are taken together with the N atom to which they are attached to form 3-8 membered heterocyclyl, optionally containing additional heteroatom(s) selected from N, O or S, wherein heterocyclyl is optionally substituted;
Re represents H, (C1-C6) alkyl, —CF3, (C3-C8) cycloalkyl, heterocyclyl, aryl or heteroaryl;
wherein alkyl, cycloalkyl, heterocyclyl, aryl and heteroaryl are optionally substituted;
p represents an integer of 1 or 2;
q represents an integer of 0, 1, 2 or 3;
r represents an integer of 0, 1, 2, 3 or 4; and
s represents an integer of 0, 1 or 2.

### Claim 10 (depends on 1)

A compound of claim 1 selected from the group consisting of:
(2-Chloro-6-fluorophenyl)(1H-pyrrolo[2,3-c]pyridine-3-yl)methanone,
3,5-Dichloro-N-ethyl-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzamide,
(4-Amino-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone,
[2,6-Dichloro-4-(2-methoxypyrimidin-5-yl)phenyl] (1H-pyrrolo[2,3-c]pyridin-3-yl)methanone,
N-[3-(2,6-Dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
3,5-Dichloro-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzonitrile,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-methylbenzamide,
N-[3-(2-Chloro-6-fluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]acetamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-ethylbenzamide,
(4-Bromo-2,6-dichlorophenyl)(1H-pyrrolo[2,3-c]pyridin-3-yl)methanone,
N-[3-(2-Chloro-6-fluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-methylbenzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-ethylbenzamide,
3,5-Dichloro-N-(2-methoxyethyl)-4-(1H-pyrrolo[2,3-c]pyridin-3-ylcarbonyl)benzamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-propylbenzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(2-methoxyethyl)benzamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-(2-methoxyethyl)benzamide,
N-[3-(2,6-Dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-5-yl]cyclopropanecarboxamide,
N-[3-(2-Chloro-6-fluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-5-yl]cyclopropanecarboxamide,
3,5-Dichloro-4-({5-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-methylbenzamide,
N-[3-(2,6-Dichloro-4-cyanobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]acetamide,
N-[3-(4-Bromo-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
N-{3-[2,6-Dichloro-4-(3,5-dimethyl-1,2-oxazol-4-yl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-[3-(4-Bromo-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]acetamide,
Methyl 3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoate,
N-[3-(4-Amino-2,6-dichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
N-[3-[4-(Acetylamino)-2,6-dichlorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
N-[3-(2-Chloro-6-fluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]propanamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-[2-(2-hydroxyethoxy)ethyl]benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(3-hydroxypropyl)benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-[3-(morpholin-4-yl)propyl]benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(2,3-dihydroxypropyl)benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-[2-(dimethylamino)ethyl]benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-[2-(piperidin-1-yl)ethyl]benzamide,
Methyl N-[3,5-dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoyl]glycinate,
N-[3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzoyl]glycine,
N-[3-(2-Chloro-3,6-difluorobenzo yl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
3,5-Dichloro-N-methyl-4-{[7-(propanoylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}benzamide,
N-[3-(2,6-Dichloro-4-cyanobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-[2-(dimethylamino)ethyl]benzamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-[2-(2-hydroxyethoxy)ethyl]benzamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-[2-(piperidin-1-yl)ethyl]benzamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-[2-(morpholin-4-yl)ethyl]benzamide,
4-{[7-(Acetylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl]carbonyl}-3,5-dichloro-N-[2-(pyrrolidin-1-yl)ethyl]benzamide,
N-[3-(2,4,6-Trichlorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
N-{3-[2,6-Dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)benzo yl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-{3-[2,6-Dichloro-4-(pyrimidin-5-yl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-{3-[2,6-Dichloro-4-(6-methoxypyridin-3-yl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-{3-[2,6-Dichloro-4-(6-fluoropyridin-3-yl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-{3-[2,6-Dichloro-4-(1-methyl-1H-pyrazol-4-yl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-[3-(4-Cyano-2,6-difluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
Methyl 4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-3,5-difluorobenzoate,
N-[3-(4-Cyano-2,6-difluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]acetamide,
3,5-Dichloro-N-cyclopropyl-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(cyclopropylmethyl)benzamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(3-ethoxypropyl)benzamide,
N-Butyl-3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)benzamide,
N-{3-[2,6-Dichloro-4-(hydroxymethyl)benzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
4-({7-[(Cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-3,5-difluoro-N-(2-fluoroethyl)benzamide,
4-({7-[(Cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-ethyl-3,5-difluorobenzamide,
4-({7-[(Cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-3,5-difluoro-N-methylbenzamide,
4-({7-[(Cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-3,5-difluoro-N-(3-hydroxypropyl)benzamide,
4-({7-[(Cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-[2-(dimethylamino)ethyl]-3,5-difluorobenzamide,
4-({7-[(Cyclopropylcarbonyl)amino]-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-(3-ethoxypropyl)-3,5-difluorobenzamide,
N-{3-[4-(3,5-Dimethyl-1,2-oxazol-4-yl)-2,6-difluorobenzoyl]-1H-pyrrolo[2,3-c]pyridin-7-yl}cyclopropanecarboxamide,
N-(3-{2,6-Dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropanecarboxamide,
N-(3-{2,6-Dichloro-4-[(ethylamino)methyl]benzoyl}-1H-pyrrolo[2,3-c]pyridin-7-yl)cyclopropanecarboxamide,
N-[3-(2,6-Dichlorobenzoyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
N-[3-(4-Bromo-2,6-difluorobenzoyl)-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
N-[3-(2,6-Difluorobenzoyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]cyclopropanecarboxamide,
3,5-Dichloro-4-({7-[(cyclopropylcarbonyl)amino]-2-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl}carbonyl)-N-methylbenzamide,
3,5-Dichloro-N-methyl-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)benzamide,
3,5-Dichloro-N-ethyl-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)benzamide,
Methyl [1-(2,6-dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]carbamate,
3,5-Dichloro-N-(2-hydroxyethyl)-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)benzamide,
3,5-Dichloro-N-(cyanomethyl)-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)benzamide,
N-[1-(2,6-Dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide,
1-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]-3-ethylurea,
Methyl [3,5-dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]carbamate,
1-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]-3-(2-hydroxyethyl)urea,
3-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]-1,1-dimethylurea,
2-Cyano-N-[3,5-dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]acetamide,
(2E)-3-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]prop-2-enamide,
(2E)-3-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]prop-2-enenitrile,
N-(Cyclopropylcarbonyl)-N-[1-(2,6-dichloro-4-cyanobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide,
N-{1-(2,6-Dichloro-4-cyanobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-{1-[2,6-Dichloro-4-(3,5-dimethyl-1,2-oxazol-4-yl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-{1-[2,6-Dichloro-4-(3,5-dimethyl-1H-pyrazol-4-yl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-{1-[2,6-Dichloro-4-(pyrimidin-5-yl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
[2,6-Dichloro-4-(hydroxymethyl)phenyl](1H-pyrrolo[3,2-c]pyridin-1-yl)methanone,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(2-hydroxyethyl)benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-ethylbenzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-ethylbenzamide,
N-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]-2-fluoroacetamide,
3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)benzonitrile,
N-{1-[2,6-Dichloro-4-(hydroxymethyl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-{1-[2,6-Dichloro-4-(hydroxymethyl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}acetamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(2-methoxyethyl)benzamide,
N-[1-(2,6-Dichloro-4-cyanobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]acetamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-(2-methoxyethyl)benzamide,
Methyl [1-(2-chloro-6-fluorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]carbamate,
N-(1-{2,6-Dichloro-4-[(ethylcarbamoyl)amino]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide,
1-[3,5-Dichloro-4-(1H-pyrrolo[3,2-c]pyridin-1-ylcarbonyl)phenyl]-3-(2-methoxyethyl)urea,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-methylbenzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-methylbenzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(propan-2-yl)benzamide,
Methyl {1-[2,6-dichloro-4-(ethylcarbamoyl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}carbamate,
N-(1-{2,6-Dichloro-4-[(cyclopropylcarbonyl)amino]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide,
N-{1-[4-(Acetylamino)-2,6-dichlorobenzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-[1-(2,6-Dichloro-4-{[(2-methoxyethyl)carbamoyl]amino}benzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide,
N-[1-(2,6-Dichloro-4-{[(2-hydroxyethyl)(methyl)carbamoyl]amino}benzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide,
N-(1-{2,6-Dichloro-4-[(cyclopropylcarbamoyl)amino]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide,
N-(1-{2,6-Dichloro-4-[(cyclopropylcarbamoyl)amino]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)acetamide,
N-[1-(2,6-Dichloro-4-{[(2-hydroxyethyl)carbamoyl]amino}benzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide,
N-[1-(2,6-Dichloro-4-{[(2-hydroxyethyl)carbamoyl]amino}benzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]acetamide,
N-(1-{2,6-Dichloro-4-[(ethylcarbamoyl)amino]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)acetamide,
3,5-Dichloro-4-[(3-chloro-1H-pyrrolo[3,2-c]pyridin-1-yl)carbonyl]-N-ethylbenzamide,
3,5-Dichloro-4-[(3-chloro-1H-pyrrolo[3,2-c]pyridin-1-yl)carbonyl]benzonitrile,
N-[1-(2,6-Dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-6-yl]cyclopropanecarboxamide,
Methyl 3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoate,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(dimethylamino)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(3-hydroxypropyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(2-hydroxyethoxy)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(morpholin-4-yl)ethyl]benzamide,
Ethyl N-[3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoyl]-b-alaninate,
N-(2-Aminoethyl)-3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-[2-(dimethylamino)ethyl]benzamide,
Ethyl N-(4-{[4-(acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichlorobenzoyl)-b-alaninate,
3,5-Dichloro-4-({6-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-ethylbenzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(3-methoxypropyl)benzamide,
3,5-Dichloro-N-cyclobutyl-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-propylbenzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-(3-methoxypropyl)benzamide,
N-[3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoyl]-b-alanine,
3,5-Dichloro-4-({3-chloro-4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-ethylbenzamide,
N-[1-(2,6-dichloro-4-cyanobenzoyl)-1H-pyrrolo[3,2-c]pyridin-6-yl]cyclopropanecarboxamide,
3,5-Dichloro-N-ethyl-4-{[4-(propanoylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(1H-indol-3-yl)ethyl]benzamide,
3,5-Dichloro-N-methyl-4-{[4-(propanoylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}benzamide,
Ethyl N-[3,5-dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoyl]alaninate,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(2-oxoimidazolidin-1-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(2,3-dihydroxypropyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(thiophen-2-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(pyridin-4-yl)ethyl]benzamide,
3,5-Dichloro-N-cyclopropyl-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(pyridin-2-ylmethyl)benz amide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(pyrrolidin-1-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[3-(morpholin-4-yl)propyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(piperidin-1-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(1-hydroxypropan-2-yl)benzamide,
N-[3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)benzoyl]-L-alanine,
3,5-Dichloro-4-({3-chloro-4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-methylbenzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(2-fluoroethyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(2,2,2-trifluoroethyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(3-ethoxypropyl)benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-(2-fluoroethyl)benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-[2-(1H-indol-3-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[(2R)-1-methoxypropan-2-yl]benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-(pyridin-2-ylmethyl)benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-[2-(pyridin-2-yl)ethyl]benzamide,
4-{[4-(Acetylamino)-1H-pyrrolo[3,2-c]pyridin-1-yl]carbonyl}-3,5-dichloro-N-[3-(morpholin-4-yl)propyl]benzamide,
N-(1-{2,6-Dichloro-4-[(methylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide,
N-(1-{2,6-Dichloro-4-[(ethylamino)methyl]benzoyl}-1H-pyrrolo[3,2-c]pyridin-4-yl)cyclopropanecarboxamide,
N-{1-[2,6-Dichloro-4-({[2-(2-oxoimidazolidin-1-yl)ethyl]amino}methyl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-{1-[2,6-Dichloro-4-({[3-(morpholin-4-yl)propyl]amino}methyl)benzoyl]-1H-pyrrolo[3,2-c]pyridin-4-yl}cyclopropanecarboxamide,
N-[1-(2,6-Dichloro-4-{[(3-hydroxypropyl)amino]methyl}benzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]cyclopropanecarboxamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(1H-pyrrol-1-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-[2-(pyridin-3-yl)ethyl]benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(cyclopropylmethyl)benzamide,
3,5-Dichloro-4-({4-[(cyclopropylcarbonyl)amino]-1H-pyrrolo[3,2-c]pyridin-1-yl}carbonyl)-N-(piperidin-3-ylmethyl)benzamide,
N-[1-(2,6-Dichlorobenzoyl)-1H-pyrrolo[3,2-c]pyridin-4-yl]acetamide,
or a pharmaceutically acceptable salt thereof, a prodrug thereof or a hydrate thereof.

### Claim 11 (depends on 1)

A pharmaceutical composition comprising a compound, a pharmaceutically acceptable salt thereof, a prodrug thereof, a hydrate thereof according to claim 1 as its active ingredient.

### Claim 12

(canceled)

### Claim 13 (depends on 1)

A method for treating or preventing a disease responsive to the inhibition of signal transduction pathway mediated at least in part by protein kinase activity, comprises administering a compound, a pharmaceutically acceptable salt thereof, a prodrug thereof, a hydrate thereof according to claim 1.

### Claim 14 (depends on 13)

The method according to claim 13, wherein protein kinase is Janus kinase.

### Claim 15 (depends on 14)

The method according to claim 14, wherein Janus Kinase is selected from JAK1, JAK2, JAK3, TYK2 or combination thereof.

### Claim 16 (depends on 13)

The method according to claim 13, wherein the disease is auto-immune and/or inflammatory disease selected from asthma, rheumatoid arthritis, psoriasis, multiple sclerosis, chronic obstructive pulmonary disease, inflammatory bowel disease or cancer.