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US20090209580A1 - Antitumor agent for thyroid cancer - Google Patents

Antitumor agent for thyroid cancerDownload PDF

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US20090209580A1
US20090209580A1US12/301,353US30135307AUS2009209580A1US 20090209580 A1US20090209580 A1US 20090209580A1US 30135307 AUS30135307 AUS 30135307AUS 2009209580 A1US2009209580 A1US 2009209580A1
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quinolinecarboxamide
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Junji Matsui
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Eisai R&D Management Co Ltd
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Eisai R&D Management Co Ltd
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Abstract

The objective of the present invention is to provide a pharmaceutical composition and a therapeutic method that are specifically effective against at least one disease selected from multiple endocrine neoplasia, type IIA, multiple endocrine neoplasia, type IIB, familial medullary thyroid carcinoma, thyroid carcinoma, papillary thyroid carcinoma, sporadic medullary thyroid carcinoma, Hirschsprung disease, pheochromocytoma, parathyroid hyperplasia and mucosal neuromas of the gastrointestinal tract.
4-(3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy)-7-methoxy-6-quinolinecarboxamide and analogs thereof are specifically effective against at least one disease selected from multiple endocrine neoplasia, type IIA, multiple endocrine neoplasia, type IIB, familial medullary thyroid carcinoma, thyroid carcinoma, papillary thyroid carcinoma, sporadic medullary thyroid carcinoma, Hirschsprung disease, pheochromocytoma, parathyroid hyperplasia and mucosal neuromas of the gastrointestinal tract.

Description

Claims (106)

Figure US20090209580A1-20090820-C00011
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00012
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
5. The therapeutic agent according toclaim 1, wherein R2represents cyano group or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent).
Figure US20090209580A1-20090820-C00015
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00016
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
25. The therapeutic agent according toclaim 21, wherein R2represents cyano group or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent).
Figure US20090209580A1-20090820-C00019
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00020
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
45. The pharmaceutical composition according toclaim 41, wherein R2represents cyano group or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent).
Figure US20090209580A1-20090820-C00023
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00024
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00025
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00026
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00027
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00028
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00029
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00030
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00031
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00032
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00033
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00034
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00035
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00036
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
Figure US20090209580A1-20090820-C00037
wherein, R1represents a group represented by Formula —V1—V2—V3(wherein, V1represents C1-6alkylene group that may have a substituent; V2represents a single bond, an oxygen atom, a sulfur atom, carbonyl group, sulfinyl group, sulfonyl group, group represented by Formula —CONR6—, group represented by Formula —SO2NR6—, group represented by Formula —NR6SO2—, group represented by Formula —NR6CO— or group represented by Formula —NR6— (wherein, R6represents a hydrogen atom, C1-6alkyl group that may have a substituent or C3-8cycloalkyl group that may have a substituent); V3represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent);
R2represents cyano group, C1-6alkoxy group that may have a substituent, carboxyl group, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent);
Y1represents a group represented by Formula
Figure US20090209580A1-20090820-C00038
(wherein, R7and R8each independently represent a hydrogen atom, a halogen atom, cyano group, nitro group, amino group, C1-6alkyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C1-6alkoxy group that may have a substituent, C1-6alkylthio group that may have a substituent, formyl group, C2-7acyl group that may have a substituent, C2-7alkoxycarbonyl group that may have a substituent or group represented by Formula —CONVd1Vd2(wherein, Vd1and Vd2each independently represent a hydrogen atom or C1-6alkyl group that may have a substituent);
W1and W2each independently represent a carbon atom or a nitrogen atom that may have a substituent);
R3and R4each independently represent a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C2-7acyl group that may have a substituent or C2-7alkoxycarbonyl group that may have a substituent; and
R5represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent,
85. The method according toclaim 81, wherein R2represents cyano group or group represented by Formula —CONVa11Va12(wherein, Va11represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent or 3-10-membered non-aromatic heterocyclic group that may have a substituent; Va12represents a hydrogen atom, C1-6alkyl group that may have a substituent, C2-6alkenyl group that may have a substituent, C2-6alkynyl group that may have a substituent, C3-8cycloalkyl group that may have a substituent, C6-10aryl group that may have a substituent, 5-10-membered heteroaryl group that may have a substituent, 3-10-membered non-aromatic heterocyclic group that may have a substituent, hydroxyl group, C1-6alkoxy group that may have a substituent or C3-8cycloalkoxy group that may have a substituent).
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US9006256B2 (en)2015-04-14
EP2036557B1 (en)2015-10-21
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RU2008149948A (en)2010-06-27
ES2556173T3 (en)2016-01-13
IL195282A (en)2014-11-30
EP2036557A4 (en)2010-06-09
WO2007136103A1 (en)2007-11-29
KR101470653B1 (en)2014-12-08
RU2448708C3 (en)2017-09-28
CN101443009A (en)2009-05-27
KR20090009937A (en)2009-01-23
RU2448708C2 (en)2012-04-27
AU2007252506C1 (en)2012-07-19
JPWO2007136103A1 (en)2009-10-01
US20110207756A1 (en)2011-08-25
IL195282A0 (en)2009-08-03
CA2652442C (en)2014-12-09
AU2007252506A1 (en)2007-11-29
CA2652442A1 (en)2007-11-29
AU2007252506B2 (en)2012-03-29
JP5190361B2 (en)2013-04-24
EP2036557A1 (en)2009-03-18

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