IP Library Granted Patent US 11,230,541
Granted Patent B2
US 11,230,541 · App. 16/634,402 · Granted Jan 25, 2022

Heterocyclic compound

Inventors: Eiji Kimura (Kanagawa, JP); Masaki Ogino (Kanagawa, JP); Yasuhisa Kohara (Kanagawa, JP); Tomoko Ohashi (Kanagawa, JP); Tomohiro Kaku (Kanagawa, JP); Yuya Oguro (Kanagawa, JP); Shigemitsu Matsumoto (Kanagawa, JP); Takeshi Wakabayashi (Kanagawa, JP); Norihito Tokunaga (Kanagawa, JP); Taku Kamei (Kanagawa, JP); Mitsuhiro Ito (Kanagawa, JP)
Assignee: Takeda Pharmaceutical Company Limited
C07D409/12A61K9/2013A61K9/2018A61K9/2054A61K9/2059A61K9/2095A61K9/4825A61K9/4858A61K9/4866A61P25/06A61P25/24A61P25/28C07D231/56C07D235/06C07D249/18C07D401/12
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Quick Facts
Patent No.
US 11,230,541
App. No.
16/634,402
Granted
Jan 25, 2022
Kind
B2
Abstract

Provided is a heterocyclic compound that can have an antagonistic action on an NMDA receptor containing the NR2B subunit, and is expected to be useful as a prophylactic or therapeutic agent for major depression, bipolar disorder, migraine, pain, peripheral symptoms of dementia and the like. A compound represented by the formula (I): wherein each symbol is as described in the DESCRIPTION, or a salt thereof.

Claims (444)

1. A compound represented by the formula (I):

or a salt thereof, wherein:

X 1 and X 2 are each a carbon atom or a nitrogen atom;

at least one of X 1 and X 2 is a nitrogen atom;

ring A is an imidazole ring, a pyrazole ring, or a triazole ring, each of which is optionally further substituted with 1 or 2 substituents independently selected from a C1-6 alkyl group and a halogen atom;

ring B is a benzene ring optionally further substituted by 1 to 3 substituents selected from:

(1) a halogen atom;

(2) a C1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a halogen atom and a C1-6 alkoxy group;

(3) a C1-6 alkoxy group; and

(4) a C3-6 cycloalkyl group;

R 1 and R 2 are each independently a hydrogen atom or a C1-6 alkyl group optionally substituted by fluorine atom(s);

R 3 is:

R 4 and R 5 are each a substituent selected from substituent group X;

Y is N or CR 6 ;

R 6 is a hydrogen atom or a substituent selected from substituent group A;

ring C 1 is a benzene ring or a pyridine ring, each of which is optionally further substituted with 1 to 3 substituents independently selected from: a halogen atom; a C1-6 alkyl group optionally substituted by 1 to 3 halogen atoms; and a C1-6 alkoxy group;

ring C 2 is a thiophene ring optionally further substituted by a substituent selected from substituent group X;

L 1 is a methylene group, O, or NH;

L 2 is a bond or a methylene group; and

ring C 3 is a benzene ring, a pyridine ring, or a thiophene ring, each of which is optionally further substituted with 1 to 5 substituents independently selected from: a halogen atom; a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms; and a C1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms;

wherein substituent group X is selected from:

(1) an optionally substituted hydrocarbon group;

(2) an optionally substituted C1-6 alkoxy group;

(3) an optionally substituted C3-10 cycloalkyloxy group;

(4) a halogen atom;

(5) a cyano group;

(6) an optionally substituted amino group;

(7) an optionally substituted C6-14 aryloxy group; and

(8) an optionally substituted C1-6 alkylthio group,

wherein:

each hydrocarbon group, C 1-6 alkoxy group, C3-10 cycloalkyloxy group, C6-14 aryloxy group, and C1-6 alkylthio group is independently optionally substituted with 1 to 3 substituents independently selected from substituent group A; and

each amino group is optionally substituted with 1 or 2 substituents selected from:

a C 1-6 alkyl group, a C 2-6 alkenyl group, a C 3-10 cycloalkyl group, a C 6-14 aryl group, a C 7-16 aralkyl group, a C 1-6 alkyl-carbonyl group, a C 6-14 aryl-carbonyl group, a C 7-16 aralkyl-carbonyl group, a 5- to 14-membered aromatic heterocyclylcarbonyl group, a 3- to 14-membered non-aromatic heterocyclylcarbonyl group, a C 1-6 alkoxy-carbonyl group, a 5- to 14-membered aromatic heterocyclic group, a carbamoyl group, a mono- or di-C 1-6 alkyl-carbamoyl group, a mono- or di-C 7-16 aralkyl-carbamoyl group, a C 1-6 alkylsulfonyl group and a C 6-14 arylsulfonyl group, each of which optionally has 1 to 3 substituents selected from substituent group A;

wherein substituent group A is selected from:

(1) a halogen atom;

(2) a nitro group;

(3) a cyano group;

(4) a hydroxy group;

(5) an optionally halogenated C 1-6 alkoxy group;

(6) a C 6-14 aryloxy group;

(7) a C 7-16 aralkyloxy group;

(8) a 5- to 14-membered aromatic heterocyclyloxy group;

(9) a 3- to 14-membered non-aromatic heterocyclyloxy group;

(10) a C 1-6 alkyl-carbonyloxy group;

(11) a C 6-14 aryl-carbonyloxy group;

(12) a C 1-6 alkoxy-carbonyloxy group;

(13) a mono- or di-C 1-6 alkyl-carbamoyloxy group;

(14) a C 6-14 aryl-carbamoyloxy group;

(15) a 5- to 14-membered aromatic heterocyclylcarbonyloxy group;

(16) a 3- to 14-membered non-aromatic heterocyclylcarbonyloxy group;

(17) an optionally halogenated C 1-6 alkylsulfonyloxy group;

(18) a C 6-14 arylsulfonyloxy group optionally substituted by a C 1-6 alkyl group;

(19) an optionally halogenated C 1-6 alkylthio group;

(20) a 5- to 14-membered aromatic heterocyclic group;

(21) a 3- to 14-membered non-aromatic heterocyclic group;

(22) a formyl group;

(23) a carboxy group;

(24) an optionally halogenated C 1-6 alkyl-carbonyl group;

(25) a C 6-14 aryl-carbonyl group;

(26) a 5- to 14-membered aromatic heterocyclylcarbonyl group;

(27) a 3- to 14-membered non-aromatic heterocyclylcarbonyl group;

(28) a C 1-6 alkoxy-carbonyl group;

(29) a C 6-14 aryloxy-carbonyl group;

(30) a C 7-16 aralkyloxy-carbonyl group;

(31) a carbamoyl group;

(32) a thiocarbamoyl group;

(33) a mono- or di-C 1-6 alkyl-carbamoyl group;

(34) a C 6-14 aryl-carbamoyl group;

(35) a 5- to 14-membered aromatic heterocyclylcarbamoyl group;

(36) a 3- to 14-membered non-aromatic heterocyclylcarbamoyl group;

(37) an optionally halogenated C 1-6 alkylsulfonyl group;

(38) a C 6-14 arylsulfonyl group;

(39) a 5- to 14-membered aromatic heterocyclylsulfonyl group;

(40) an optionally halogenated C 1-6 alkylsulfinyl group;

(41) a C 6-14 arylsulfinyl group;

(42) a 5- to 14-membered aromatic heterocyclylsulfinyl group;

(43) an amino group;

(44) a mono- or di-C 1-6 alkylamino group;

(45) a mono- or di-C 6-14 arylamino group;

(46) a 5- to 14-membered aromatic heterocyclylamino group;

(47) a C 7-16 aralkylamino group;

(48) a formylamino group;

(49) a C 1-6 alkyl-carbonylamino group;

(50) a (C 1-6 alkyl)(C 1-6 alkyl-carbonyl)amino group;

(51) a C 6-14 aryl-carbonylamino group;

(52) a C 1-6 alkoxy-carbonylamino group;

(53) a C 7-16 aralkyloxy-carbonylamino group;

(54) a C 1-6 alkylsulfonylamino group;

(55) a C 6-14 arylsulfonylamino group optionally substituted by a C 1-6 alkyl group;

(56) an optionally halogenated C 1-6 alkyl group;

(57) a C 2-6 alkenyl group;

(58) a C 2-6 alkynyl group;

(59) a C 3-10 cycloalkyl group;

(60) a C 3-10 cycloalkenyl group; and

(61) a C 6-14 aryl group.

2. The compound according to claim 1 , or a salt thereof, wherein:

ring A is an imidazole ring (that is, X 1 is a carbon atom, and X 2 is a nitrogen atom), a pyrazole ring (that is, X 1 is a nitrogen atom, and X 2 is a carbon atom), or a triazole ring (that is, X 1 and X 2 are both nitrogen atoms), each of which is optionally further substituted by 1 or 2 substituents selected from a C 1-6 alkyl group and a halogen atom;

ring B is a benzene ring optionally further substituted by 1 to 3 substituents selected from:

(1) a halogen atom:

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 substituents selected from a halogen atom and a C 1-6 alkoxy group;

(3) a C 1-6 alkoxy group; and

(4) a C 3-6 cycloalkyl group;

R 1 and R 2 are both hydrogen atoms;

R 3 is:

R 4 is:

(1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;

(2) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms; or

(3) a halogen atom;

R 5 is:

(1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;

(2) a C 3-6 cycloalkyl group;

(3) a C 1-6 alkoxy group; or

(4) a halogen atom;

ring C 1 is a benzene ring (that is, Y is CR 6 ) or a pyridine ring (that is, Y is N), each of which is optionally further substituted by 1 to 3 substituents selected from:

(1) a halogen atom;

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms; and

(3) a C 1-6 alkoxy group;

R 6 is:

(1) a hydrogen atom;

(2) a halogen atom; or

(3) a C 1-6 alkyl group;

ring C 2 is a thiophene ring optionally further substituted by 1 or 2 halogen atoms;

L 1 is a methylene group or NH;

L 2 is a bond; and

ring C 3 is a thiophene ring or a benzene ring, each of which is optionally further substituted by 1 to 5 substituents selected from:

(1) a halogen atom;

(2) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms; and

(3) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms.

3. The compound according to claim 1 , or a salt thereof, wherein:

ring A is an imidazole ring (that is, X 1 is a carbon atom, and X 2 is a nitrogen atom) optionally further substituted by 1 or 2 substituents selected from a C 1-6 alkyl group;

ring B is a benzene ring optionally further substituted by 1 to 3 substituents selected from a C 1-6 alkyl group and a C 1-6 alkoxy group;

R 1 and R 2 are both hydrogen atoms;

R 3 is:

R 4 is:

(1) a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms; or

(2) a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms;

R 5 is a C 1-6 alkyl group optionally substituted by 1 to 3 halogen atoms;

ring C 1 is a benzene ring (that is, Y is CR 6 ) or a pyridine ring (that is, Y is N), each of which is optionally further substituted by 1 to 3 halogen atoms;

R 6 is:

(1) a hydrogen atom; or

(2) a halogen atom; and

ring C 2 is a thiophene ring not further substituted.

4. The compound according to claim 1 , or a salt thereof, wherein:

ring A is an imidazole ring (that is, X 1 is a carbon atom, and X 2 is a nitrogen atom) optionally further substituted by 1 or 2 substituents selected from a C 1-6 alkyl group;

ring B is a benzene ring optionally further substituted by 1 to 3 substituents selected from a C 1-6 alkyl group and a C 1-6 alkoxy group;

R 1 and R 2 are both hydrogen atoms;

R 3 is

R 4 is a C 1-6 alkoxy group optionally substituted by 1 to 3 halogen atoms;

ring C 1 is a benzene ring (that is, Y is CR 6 ) or a pyridine ring (that is, Y is N), each of which is optionally further substituted by 1 to 3 halogen atoms; and

R 6 is:

(1) a hydrogen atom; or

(2) a halogen atom.

5. A compound which is 3,5-difluoro-4-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzamide or a salt thereof.

6. A compound which is 6-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-5-fluoronicotinamide or a salt thereof.

7. A compound which is N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethoxy)benzamide or a salt thereof.

8. A medicament comprising the compound according to claim 1 or a salt thereof.

9. The medicament according to claim 8 , further comprising a pharmaceutically acceptable carrier.

10. A method for antagonizing an NMDA receptor containing an NR2B subunit in a mammal, comprising administering an effective amount of the compound according to claim 1 or a salt thereof to the mammal.

11. A method for treating major depression, bipolar disorder, migraine, pain or peripheral symptoms of dementia in a mammal, comprising administering an effective amount of the compound according to claim 1 or a salt thereof to the mammal.

12. The compound according to claim 1 , which is selected from:

N-((2,5-dimethyl-2H-indazol-4-yl)methyl)-4-(trifluoromethoxy)benzamide;

N-((5-methyl-1H-indazol-4-yl)methyl)-4-(trifluoromethoxy)benzam ide;

N-((5-methyl-1H-benzimidazol-4-yl)methyl)-4-(trifluoromethoxy)benzam ide;

N-((5-iodo-1H-indazol-4-yl)methyl)-4-(trifluoromethoxy)benzam ide;

4-(trifluoromethoxy)-N-((5-(trifluoromethyl)-1H-indazol-4-yl)methyl)benzam ide;

N-((5-methoxy-1H-indazol-4-yl)methyl)-4-(trifluoromethoxy)benzam ide;

N-(1H-indazol-4-ylmethyl)-4-(trifluoromethoxy)benzam ide;

3,5-difluoro-4-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3,5-difluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methylbenzamide;

5-fluoro-6-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

3-fluoro-4-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethoxy)benzam ide;

3-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)benzam ide;

3-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methylbenzamide;

4-chloro-3,5-difluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((5-ethyl-1H-indazol-4-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

3-chloro-4,5-difluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-5-fluoro-6-methoxynicotinamide;

N-((6-cyclopropyl-1-methyl-1H-benzimidazol-7-yl)methyl)-5-fluoro-6-methoxynicotinamide;

N-((6-cyclopropyl-1-methyl-1H-benzimidazol-7-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-5-fluoro-6-methoxynicotinamide;

N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

3,5-difluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)benzam ide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3,5-difluoro-4-(trifluoromethyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-5-methylthiophene-3-carboxamide;

5-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

5-ethyl-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3-fluoro-4-(trifluoromethoxy)benzamide;

3-chloro-4-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-5-methylthiophene-2-carboxamide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-2-(2-thienyl)acetamide;

3-chloro-4-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3,5-dimethylbenzamide;

5-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

3-chloro-4-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methylbenzamide;

4-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-methylbenzamide;

4-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(trifluoromethyl)benzam ide;

3,4,5-trifluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzamide;

4-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methylthiophene-2-carboxamide;

4-chloro-3-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-chloro-3-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-fluoro-3-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methyl-3-(trifluoromethyl)benzamide;

5-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

3,5-dichloro-4-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-5-(trifluoromethyl)thiophene-2-carboxamide;

3-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)benzam ide;

3-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethoxy)benzam ide;

4,5-dichloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

3,4-difluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-5-methylbenzamide;

3,4-dichloro-5-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-6-(trifluoromethoxy)-nicotinamide;

5-chloro-6-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

5-chloro-6-ethoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

6-(difluoromethoxy)-5-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

3-chloro-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethoxy)-benzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(trifluoromethyl)benzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(trifluoromethoxy)benzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methylthiophene-2-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-methylthiophene-2-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-2-(2-thienyl)acetamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-methylthiophene-3-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-methoxythiophene-2-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methoxythiophene-2-carboxamide;

5-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)thiophene-3-carboxamide;

4-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)thiophene-2-carboxamide;

5-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)thiophene-2-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-fluoro-3-methoxybenzamide;

4-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-methylbenzamide;

3-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methylbenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-fluoro-3-methylbenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3,4-difluoro-5-methylbenzamide;

3-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-fluorobenzamide;

4-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-fluorobenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3,4,5-trifluorobenzamide;

3-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methoxybenzamide;

4-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-methoxybenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-(trifluoromethyl)thiophene-2-carboxamide;

4,5-dichloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)thiophene-2-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methyl-3-(trifluoromethyl)benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-fluoro-3-(trifluoromethyl)benzam ide;

3,5-dichloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-fluorobenzamide;

3,4-dichloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-fluorobenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-fluoro-4-(trifluoromethoxy)benzam ide;

3-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(trifluoromethyl)benzam ide;

4-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3,5-difluorobenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3,5-difluoro-4-(trifluoromethyl)benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-fluoro-4-(trifluoromethyl)benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-fluoro-4-methylbenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3-fluoro-4-methoxybenzamide;

3-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4,5-difluorobenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-fluoro-6-methoxynicotinamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-3,5-difluoro-4-methylbenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethyl)benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methylbenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethoxy)benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-methoxybenzamide;

4-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)benzam ide;

5-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-6-methoxynicotinamide;

5-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-6-ethoxynicotinamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-6-(difluoromethoxy)-5-fluoronicotinamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-6-(trifluoromethoxy)-nicotinamide;

3-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethoxy)-benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethyl)-3,5-difluorobenzamide;

4-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3-fluorobenzamide;

5-(difluoromethyl)-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

3-chloro-5-fluoro-4-methoxy-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3-chloro-4-(difluoromethyl)-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

5-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-6-(trifluoromethyl)-nicotinamide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methylbenzamide;

5-cyclopropyl-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

4-chloro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethyl)-3-fluorobenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-6-ethoxy-5-fluoronicotinamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethoxy)-3-fluorobenzamide;

5-chloro-N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-6-(difluoromethoxy)-nicotinamide;

5-ethyl-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

4-(difluoromethyl)-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-(difluoromethyl)-3-fluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

5-(difluoromethyl)-N-((6-ethoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

5-(difluoromethyl)-N-((6-ethoxy-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

N-((6-ethoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

N-((6-ethoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)-benzam ide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3-fluoro-4-methoxybenzamide;

N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-3-fluoro-4-methoxybenzamide;

4-(difluoromethoxy)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-3,5-difluorobenzamide;

5-(difluoromethyl)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

4-(difluoromethyl)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)benzamide;

6-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-5-fluoronicotinamide;

4-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)benzamide;

4-(difluoromethyl)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3-fluorobenzamide;

5-(difluoromethyl)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-6-(trifluoromethoxy)-nicotinamide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-5-(trifluoromethyl)-thiophene-3-carboxamide;

4-(difluoromethyl)-N-((6-ethoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-(difluoromethyl)-N-((6-ethoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-fluorobenzamide;

5-(difluoromethyl)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

6-(difluoromethoxy)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-5-fluoronicotinamide;

5-cyclopropyl-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methoxybenzamide;

4-(difluoromethyl)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-3-fluorobenzamide;

5-chloro-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

4-(difluoromethoxy)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)-6-(trifluoromethoxy)-nicotinamide;

N-((1-ethyl-6-methoxy-1H-benzimidazol-7-yl)methyl)-5-fluoro-6-methoxynicotinamide;

N-((1-ethyl-6-methoxy-1H-benzimidazol-7-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethoxy)-benzam ide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-4-(difluoromethoxy)-3,5-difluorobenzamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-(difluoromethyl)-thiophene-3-carboxamide;

N-((5-cyclopropyl-1H-indazol-4-yl)methyl)-5-(difluoromethyl)-thiophene-2-carboxamide;

5-chloro-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

4-(difluoromethyl)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)benzamide;

4-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-3,5-difluorobenzamide;

6-(difluoromethoxy)-N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

3,5-difluoro-4-methoxy-N-((1-methyl-1H-benzimidazol-7-yl)methyl)benzamide;

4-(difluoromethoxy)-3,5-difluoro-N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)benzam ide;

N-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-5-(trifluoromethyl)-thiophene-2-carboxamide hydrochloride;

N-((1,6-dimethyl-1H-benzimidazol-7-yl)methyl)-5-(trifluoromethyl)-thiophene-3-carboxamide;

6-(difluoromethoxy)-N-((6-ethyl-1-methyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

N-((5-cyclopropyl-1H-benzotriazol-4-yl)methyl)-5-fluoro-6-methoxynicotinamide;

5-chloro-N-(1H-indazol-4-ylmethyl)thiophene-3-carboxamide;

N-(1H-indazol-4-ylmethyl)-5-(trifluoromethyl)-thiophene-2-carboxamide;

4,5-dichloro-N-(1H-indazol-4-ylmethyl)thiophene-2-carboxamide;

5-chloro-N-(1H-indazol-4-ylmethyl)-6-methoxynicotinamide;

N-(1H-indazol-4-ylmethyl)-6-(trifluoromethoxy)-nicotinamide;

6-ethoxy-5-fluoro-N-(1H-indazol-4-ylmethyl)nicotinamide;

5-fluoro-N-(1H-indazol-4-ylmethyl)-6-methoxynicotinamide;

3,5-difluoro-N-(1H-indazol-4-ylmethyl)-4-(trifluoromethyl)-benzamide;

3-fluoro-N-(1H-indazol-4-ylmethyl)-4-(trifluoromethyl)-benzamide;

N-(1H-indazol-4-ylmethyl)-4-(trifluoromethyl)-benzamide;

3-fluoro-N-(1H-indazol-4-ylmethyl)-4-methylbenzamide;

4-(difluoromethyl)-N-(1H-indazol-4-ylmethyl)benzamide;

4-(difluoromethyl)-3-fluoro-N-(1H-indazol-4-ylmethyl)benzamide;

3-fluoro-N-(1H-indazol-4-ylmethyl)-4-(trifluoromethoxy)-benzamide;

3,5-difluoro-N-(1H-indazol-4-ylmethyl)-4-methoxybenzamide;

3-fluoro-N-(1H-indazol-4-ylmethyl)-4-methoxybenzamide;

3-chloro-4-(difluoromethoxy)-N-(1H-indazol-4-ylmethyl)benzamide;

4-(difluoromethoxy)-N-(1H-indazol-4-ylmethyl)benzamide;

4-(difluoromethoxy)-3,5-difluoro-N-(1H-indazol-4-ylmethyl)benzamide;

3-chloro-N-(1H-indazol-4-ylmethyl)-4-methylbenzamide;

3-chloro-4-fluoro-N-(1H-indazol-4-ylmethyl)benzamide;

4-chloro-3-fluoro-N-(1H-indazol-4-ylmethyl)benzamide;

3-chloro-4,5-difluoro-N-(1H-indazol-4-ylmethyl)benzamide;

4-chloro-3,5-difluoro-N-(1H-indazol-4-ylmethyl)benzamide;

3-chloro-4-(difluoromethyl)-N-(1H-indazol-4-ylmethyl)benzamide;

6-(difluoromethoxy)-5-fluoro-N-(1H-indazol-4-ylmethyl)nicotinamide;

4-(difluoromethoxy)-3-fluoro-N-(1H-indazol-4-ylmethyl)benzamide;

5-fluoro-6-methoxy-N-((5-methyl-1H-benzotriazol-4-yl)methyl)nicotinamide;

N-((5-methyl-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethoxy)-benzamide;

3,5-difluoro-N-((5-methyl-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethyl)-benzam ide;

3,5-difluoro-4-methyl-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

3,5-difluoro-4-methoxy-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

4-chloro-3,5-difluoro-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

3-fluoro-N-((5-methyl-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethyl)-benzamide;

3-fluoro-4-methyl-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

3-fluoro-4-methoxy-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

3-chloro-4,5-difluoro-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

N-((5-cyclopropyl-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethoxy)-benzamide;

N-((5-cyclopropyl-1H-benzotriazol-4-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

N-((5-ethyl-1H-benzotriazol-4-yl)methyl)-3,5-difluoro-4-(trifluoromethyl)-benzamide;

N-((5-ethyl-1H-benzotriazol-4-yl)methyl)-3,5-difluoro-4-methoxybenzamide;

3,5-difluoro-4-methoxy-N-((5-methoxy-1H-benzotriazol-4-yl)methyl)benzamide;

N-((5-ethyl-1H-benzotriazol-4-yl)methyl)-5-fluoro-6-methoxynicotinamide;

N-((5-ethyl-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethoxy)-benzamide;

3,5-difluoro-N-((6-fluoro-1-methyl-1H-benzimidazol-7-yl)methyl)-4-methoxybenzamide;

N-(1H-benzotriazol-4-yl methyl)-3,5-difluoro-4-methoxybenzamide;

N-((5-cyclopropyl-1H-benzotriazol-4-yl)methyl)-4-(difluoromethoxy)-3-fluorobenzamide;

N-((5-methoxy-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethoxy)-benzamide;

3,5-difluoro-4-methoxy-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(3-methylphenyl)urea;

1-(3-fluorophenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(4-fluoro-3-methylphenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(3-fluoro-4-methylphenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(3-chlorophenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(3,4,5-trifluorophenyl)urea;

1-(4-(difluoromethoxy)-phenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(3-(trifluoromethyl)-phenyl)urea;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(4-(trifluoromethoxy)-phenyl)urea;

1-(4-fluorophenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(3-fluoro-4-methoxyphenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

N-((5-cyclopropyl-1H-benzotriazol-4-yl)methyl)-6-(difluoromethoxy)-5-fluoronicotinamide;

3-fluoro-N-((5-methoxy-1H-benzotriazol-4-yl)methyl)-4-(trifluoromethoxy)-benzamide;

5-chloro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

5-chloro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-2-carboxamide;

N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-5-(trifluoromethyl)-thiophene-3-carboxamide;

N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-5-(trifluoromethyl)-thiophene-2-carboxamide;

5-(difluoromethyl)-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)thiophene-3-carboxamide;

N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-6-(trifluoromethoxy)-nicotinamide;

6-ethoxy-5-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

5-fluoro-6-methoxy-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

3-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)-benzam ide;

N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethyl)-benzam ide;

3-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-4-methylbenzamide;

3,5-difluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-4-methylbenzamide;

4-(difluoromethyl)-3,5-difluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-(difluoromethyl)-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-(difluoromethyl)-3-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3-fluoro-4-methoxy-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3-chloro-4-(difluoromethoxy)-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-(difluoromethoxy)-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-(difluoromethoxy)-3,5-difluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3-chloro-4-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-chloro-3-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

4-chloro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

3-chloro-4-(difluoromethyl)-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

6-(difluoromethoxy)-5-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)-4-(trifluoromethoxy)-benzam ide;

4-(difluoromethoxy)-3-fluoro-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)benzam ide;

6-(difluoromethoxy)-N-((6-methoxy-1,2-dimethyl-1H-benzimidazol-7-yl)methyl)nicotinamide;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-phenylurea;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(4-methylphenyl)urea;

1-(4-chlorophenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(3,4-difluorophenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(2,3-difluoro-4-methoxyphenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(2-fluoro-4-(trifluoromethyl)-phenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-(3-fluoro-4-(trifluoromethyl)-phenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(4-(trifluoromethyl)-phenyl)urea;

4-(difluoromethoxy)-3-fluoro-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzam ide;

4-methoxy-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

4-(difluoromethoxy)-N-((5-methyl-1H-benzotriazol-4-yl)methyl)benzamide;

1-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)-3-(4-methoxyphenyl)urea;

1-(4-fluoro-3-(trifluoromethyl)-phenyl)-3-((6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl)urea;

6-(difluoromethoxy)-5-fluoro-N-((5-methyl-1H-benzotriazol-4-yl)methyl)nicotinamide;

3-fluoro-N-((3-methyl-1H-indazol-4-yl)methyl)-4-(trifluoromethoxy)-benzamide;

3,5-difluoro-4-methoxy-N-((3-methyl-1H-indazol-4-yl)methyl)benzamide;

6-(difluoromethoxy)-5-fluoro-N-((3-methyl-1H-indazol-4-yl)methyl)nicotinamide;

N-[(3-bromo-1H-indazol-4-yl)methyl]-3-fluoro-4-(trifluoromethoxy)-benzamide;

N-[(5-fluoro-1H-indazol-4-yl)methyl]-4-(trifluoromethoxy)-benzamide;

3-fluoro-N-[(1-methyl-1H-benzotriazol-7-yl)methyl]-4-(trifluoromethoxy)-benzamide;

6-(difluoromethoxy)-5-fluoro-N-[(1-methyl-1H-benzotriazol-7-yl)methyl]pyridine-3-carboxamide;

6-(difluoromethoxy)-N-[(6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl]pyridine-3-carboxamide;

4-(difluoromethoxy)-2-fluoro-N-[(6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl]benzamide;

N-[(6-methoxy-1-methyl-1H-benzimidazol-7-yl)methyl]-4-(2,2,2-trifluoroethyl)-benzamide;

3,5-difluoro-4-methoxy-N-{[6-(methoxymethyl)-1-methyl-1H-benzimidazol-7-yl]methyl}benzamide;

N-{[6-(methoxymethyl)-1-methyl-1H-benzimidazol-7-yl]methyl}-4-(trifluoromethyl)-benzamide;

6-(difluoromethoxy)-5-fluoro-N-{[6-(methoxymethyl)-1-methyl-1H-benzimidazol-7-yl]methyl}pyridine-3-carboxamide;

N-{[6-(methoxymethyl)-1-methyl-1H-benzimidazol-7-yl]methyl}-5-(trifluoromethyl)-thiophene-3-carboxamide;

3-chloro-4-(difluoromethoxy)-N-{[6-(methoxymethyl)-1-methyl-1H-benzimidazol-7-yl]methyl}benzamide; and

3-fluoro-N-{[6-(methoxymethyl)-1-methyl-1H-benzimidazol-7-yl]methyl}-4-(trifluoromethoxy)-benzam ide, or a salt thereof.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 18, 2020
From: KIMURA, EIJI; OGINO, MASAKI; KOHARA, YASUHISA; OHASHI, TOMOKO; KAKU, TOMOHIRO; OGURO, YUYA; MATSUMOTO, SHIGEMITSU; WAKABAYASHI, TAKESHI; TOKUNAGA, NORIHITO; KAMEI, TAKU; ITO, MITSUHIRO
To: TAKEDA PHARMACEUTICAL COMPANY LIMITED
Reel/Frame 052686/0584 →
Priority Claims (1)
JP JP2017-146744 · Jul 28, 2017 · national
Continuity (1)
Related Publication 20200231579A1 · Jul 23, 2020
Cited By (2)
US 12,630,509 US 12,637,418