US 8,785,481 B2Granted

Ether benzotriazole derivatives

AssigneeMerck Sharp & Dohme Corp.

InventorsDouglas C. Beshore, Vadim Dudkin, Robert M. Garbaccio, Adam W. Johnson, Scott D. Kuduk, Jason W. Skudlarek, Cheng Wang, Mark E. Fraley

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Abstract

The present invention is directed to ether benzotriazole derivatives which are potentiators of metabotropic glutamate receptors, particularly the mGluR2 receptor, and which are useful in the treatment or prevention of neurological and psychiatric disorders associated with glutamate dysfunction and diseases in which metabotropic glutamate receptors are involved. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which metabotropic glutamate receptors are involved.

Claims13

Dependent claims

A compound according to Formula I

or a pharmaceutically acceptable salt thereof, wherein:
R1 is selected from the group consisting of:
(1) C2-8alkyl,
(2) C2-8alkenyl,
(3) C2-8alkynyl,
(4) C3-6cycloalkyl-(CH2)p—, wherein p is 1, 2, 3 or 4, and
(5) benzyl, wherein groups (1) to (5) above are optionally substituted with 1 to 3 Ra groups;
each Ra and R2 is independently selected from the group consisting of:
halo, OH, C1-4alkyl, C1-4alkoxy, CF3, —OCF3 and —CN;
Y is halo, CN or CF3;
X is C1-8alkyl, C3-8cycloalkyl, C2-8alkenyl or C2-8alkynyl, any of which is optionally substituted with up to 4 substituents selected from R3, said C3-8cycloalkyl further optionally substituted with 1 or 2 oxo groups and said C1-8alkyl further optionally substituted with ═N—OH;
each R3 is independently selected from the group consisting of:
halogen, OH, CN, CF3, R5, OR5, SR5, SOR5, SO2R5, SO2N(R4)2, COR4, CO2R5, CON(R4)2, CON(R4)OR5, N(R4)2, NO2, NR4COR5, NR4CO2R5, NR4—C1-4alkyl-CO2R5, —C1-4alkyl-N(R4)2, —C1-4alkyl-NR4COR5 and —C1-4alkyl-NR4CO2R5;
each R4 independently represents:
(1) H, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C3-10cycloalkylC1-4alkyl, C3-10cycloalkenyl or C3-10cycloalkenylC1-4-alkyl, any of which except H optionally bear up to 5 halogen atoms or OH, CN, CF3 and C1-4alkoxy;
(2) phenyl, benzyl or heteroaryl, optionally bridged with a methylene, any of which optionally bear up to 3 substituents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C1-4hydroxyalkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, carbamoyl, CO2—C1-4alkyl, C1-4alkylamino and di(C1-4alkyl)amino;
and (3) Het, optionally bridged with a methylene and said Het optionally bearing up to 3 substituents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C1-4hydroxyalkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, carbamoyl, CO2—C1-4alkyl, C1-4alkylamino and di(C1-4alkyl)amino;
or when two R4 group are attached to the same nitrogen atom, they may be joined together with said nitrogen atom to form a non-aromatic monocyclic, a non-aromatic or partially aromatic bicyclic or a non-aromatic spiro-linked heterocyclic system of up to 12 ring atoms which optionally bears up to 4 substitutents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, C1-4alkylamino and di(C1-4alkyl)amino;
R5 has the same definition as R4 except that R5 is not H;
each “heteroaryl” independently refers to 5- or 6-membered aromatic monocyclic or 9- or 10-membered aromatic bicyclic ring systems, in which at least one ring atom is selected from N or N-oxide, O and S, excluding tetrazolyl;
and
each “Het” independently refers to nonaromatic or partially aromatic mono- or bicyclic heterocyclic systems of up to 10 ring atoms, in which at least one ring atom is selected from N, O and S, where the sulfur atom may be in the form of the S-oxide or S,S-dioxide.

19 more elements

A compound according to Formula I

or a pharmaceutically acceptable salt thereof, wherein:
R1 is selected from the group consisting of:
(1) C2-8alkyl,
(2) C2-8alkenyl,
(3) C2-8alkynyl,
(4) C3-6cycloalkyl-(CH2)p—, wherein p is 1, 2, 3 or 4, and
(5) benzyl, wherein groups (1) to (5) above are optionally substituted with 1 to 3 Ra groups;
each Ra and R2 is independently selected from the group consisting of:
halo, OH, C1-4alkyl, C1-4alkoxy, CF3, —OCF3 and —CN;
Y is halo, CN or CF3;
X is benzyl, benzoylmethyl, heteroaryl-methyl-, heteroaryl-ethyl- or heteroaryl -propyl-, any of which is optionally substituted with up to 4 substituents selected from R3;
each R3 is independently selected from the group consisting of:
halogen, OH, CN, CF3, R5, OR5, SR5, SOR5, SO2R5, SO2N(R4)2, COR4, CO2R5, CON(R4)2, CON(R4)OR5, N(R4)2, NO2, NR4COR5, NR4CO2R5, NR4—C1-4alkyl-CO2R5, —C1-4 alkyl-N(R4)2, —C1-4-alkyl-NR4COR5 and —C1-4alkyl-NR4CO2R5;
each R4 independently represents:
(1) H, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C3-10cycloalkylC1-4alkyl, C3-10cycloalkenyl or C3-10cycloalkenylC1-4alkyl, any of which except H optionally bear up to 5 halogen atoms or OH, CN, CF3 and C1-4alkoxy;
(2) phenyl, benzyl or heteroaryl, optionally bridged with a methylene, any of which optionally bear up to 3 substituents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C1-4hydroxyalkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, carbamoyl, CO2—C1-4alkyl, C1-4alkylamino and di(C1-4alkyl)amino;
and (3) Het, optionally bridged with a methylene and said Het optionally bearing up to 3 substituents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C1-4hydroxyalkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, carbamoyl, CO2—C1-4alkyl, C1-4alkylamino and di(C1-4alkyl)amino;
or when two R4 group are attached to the same nitrogen atom, they may be joined together with said nitrogen atom to form a non-aromatic monocyclic, a non-aromatic or partially aromatic bicyclic or a non-aromatic spiro-linked heterocyclic system of up to 12 ring atoms which optionally bears up to 4 substitutents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, C1-4alkylamino and di(C1-4alkyl)amino;
R5 has the same definition as R4 except that R5 is not H;
each “heteroaryl” independently refers to 5- or 6-membered aromatic monocyclic or 9- or 10-membered aromatic bicyclic ring systems, in which at least one ring atom is selected from N or N-oxide, O and S, excluding tetrazolyl;
and
each “Het” independently refers to nonaromatic or partially aromatic mono- or bicyclic heterocyclic systems of up to 10 ring atoms, in which at least one ring atom is selected from N, O and S, where the sulfur atom may be in the form of the S-oxide or S,S-dioxide.

19 more elements

A compound according to Formula I

or a pharmaceutically acceptable salt thereof, wherein:
R1 is selected from the group consisting of:
(1) C2-8alkyl,
(2) C2-8alkenyl,
(3) C2-8alkynyl,
(4) C3-6cycloalkyl-(CH2)p—, wherein p is 1, 2, 3 or 4, and
(5) benzyl, wherein groups (1) to (5) above are optionally substituted with 1 to 3 Ra groups;
each Ra and R2 is independently selected from the group consisting of:
halo, OH, C1-4alkyl, C1-4alkoxy, CF3, —OCF3 and —CN;
Y is halo, CN or CF3;
X is Het, Het-methyl-, Het-ethyl- or Het-propyl-, any of which is optionally substituted with up to 4 substituents selected from R3, the Het portions thereof further optionally substituted with 1 or 2 oxo groups;
each R3 is independently selected from the group consisting of:
halogen, OH, CN, CF3, R5, OR5, SR5, SOR5, SO2R5, SO2N(R4)2, COR4, CO2R5, CON(R4)2, CON(R4)OR5, N(R4)2, NO2, NR4COR5, NR4CO2R5, NR4—C1-4alkyl-CO2R5, —C1-4alkyl-N(R4)2, —C1-4alkyl-NR4COR5 and —C1-4alkyl-NR4CO2R5;
each R4 independently represents:
(1) H, C1-6alkyl, C2-6alkenyl, C2-6alkynyl, C3-10cycloalkyl, C3-10cycloalkylC1-4alkyl, C3-10cycloalkenyl or C3-10cycloalkenylC1-4alkyl, any of which except H optionally bear up to 5 halogen atoms or OH, CN, CF3 and C1-4alkoxy;
(2) phenyl, benzyl or heteroaryl, optionally bridged with a methylene, any of which optionally bear up to 3 substituents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C1-4hydroxyalkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, carbamoyl, CO2—C1-4alkyl, C1-4alkylamino and di(C1-4alkyl)amino;
and (3) Het, optionally bridged with a methylene and said Het optionally bearing up to 3 substituents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C1-4hydroxyalkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, carbamoyl, CO2—C1-4alkyl, C1-4alkylamino and di(C1-4alkyl)amino;
or when two R4 group are attached to the same nitrogen atom, they may be joined together with said nitrogen atom to form a non-aromatic monocyclic, a non-aromatic or partially aromatic bicyclic or a non-aromatic spiro-linked heterocyclic system of up to 12 ring atoms which optionally bears up to 4 substitutents independently selected from halogen, OH, oxo, CN, CF3, C1-4alkyl, C3-6cycloalkyl, phenyl, heteroaryl, C1-4alkoxy, acetyl, amino, C1-4alkylamino and di(C1-4alkyl)amino;
R5 has the same definition as R4 except that R5 is not H;
each “heteroaryl” independently refers to 5- or 6-membered aromatic monocyclic or 9- or 10-membered aromatic bicyclic ring systems, in which at least one ring atom is selected from N or N-oxide, O and S, excluding tetrazolyl;
and
each “Het” independently refers to nonaromatic or partially aromatic mono- or bicyclic heterocyclic systems of up to 10 ring atoms, in which at least one ring atom is selected from N, O and S, where the sulfur atom may be in the form of the S-oxide or S,S-dioxide.

19 more elements

A compound selected from the following group:

4-bromo-1-(2,2-dimethylpropyl)-5-methoxy-1H-1,2,3-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-ol;
4-bromo-1-(cyclopentylmethyl)-5-methoxy-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-ethoxy-1H-benzotriazole;
4-bromo-1-(cyclohexylmethyl)-5-methoxy-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-methoxy-1H-benzotriazole;
4-bromo-1-butyl-5-methoxy-1H-benzotriazole;
4-chloro-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-ol;
4-chloro-1-(2,2-dimethylpropyl)-5-methoxy-1H-benzotriazole;
4-bromo-1-(4,4,4-trifluorobutyl)-1H-benzotriazol-5-ol;
4-bromo-5-methoxy-1-(4,4,4-trifluorobutyl)-1H-benzotriazole;
4-bromo-1-[(3,3-difluorocyclobutyl)methyl]-5-methoxy-1H-benzotriazole;
5-(benzyloxy)-4-bromo-1-[(3,3-difluoro cyclobutyl)methyl]-1H-benzotriazole;
4,6-dibromo-1-(4,4,4-trifluorobutyl)-1H-benzotriazol-5-ol;
4,6-dibromo-1-[(1R)-1,2,2-trimethylpropyl]-1H-benzotriazol-5-ol;
4-bromo-1-[(1R)-1,2,2-trimethylpropyl]-1H-benzotriazol-5-ol;
4,6-dibromo-1-[(1R)-1,2-dimethylpropyl]-1H-benzotriazol-5-ol;
4-bromo-1-[(1R)-1,2-dimethylpropyl]-1H-benzotriazol-5-ol;
4-bromo-5-(3-bromopropoxy)-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(prop-2-en-1-yloxy)-1H-benzotriazole;
5-{[3,5-bis(trifluoromethyl)benzyl]oxy}-4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazole;
2-{[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}-1-phenylethanone;
5-(benzyloxy)-4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazole;
methyl 4-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)benzoate;
methyl 3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)benzoate;
4-bromo-1-(2,2-dimethylpropyl)-5-(1-phenylethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(2-fluoroethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(trifluoromethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-{[6-(trifluoromethyl)pyridin-3-yl]methoxy}-1H-benzotriazole;
methyl 3′-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)-4-hydroxybiphenyl-3-carboxylate;
3-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyridine-2-carbonitrile;
2-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyridine-3-carbonitrile;
3-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]-5-(1-hydroxy-1-methylethyl)pyridine-2-carbonitrile;
2-{4-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyridin-3-yl}propan-2-ol;
2-{3-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyridin-2-yl}propan-2-ol;
2-{4-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyridin-2-yl}propan-2-ol;
3-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]-5-methylpyridine-2-carbonitrile;
6-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}methyl)phenyl]pyridine-2-carbonitrile;
4-bromo-1-(2,2-dimethylpropyl)-5-({3-[1-(1,1-dioxidothio-morpholin-4-yl)ethyl]pyridin-2-yl}oxy)-1H-benzotriazole;
3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenol;
5-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyrimidine-2-carbonitrile;
5-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyrimidine-2-carboxamide;
5-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]pyrimidin-2-ol;
4-bromo-1-(2,2-dimethylpropyl)-5-{[3-(5-methoxypyridin-2-yl)benzyl]oxy}-1H-benzotriazole;
4-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)phenyl]-1H-pyrazole-3-carbonitrile;
4-bromo-1-(2,2-dimethylpropyl)-5-(pyrazin-2-ylmethoxy)-1H-1,2,3-benzotriazole;
4-bromo-5-[1-(3-bromophenyl)ethoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(1S)-1-pyridin-2-ylethoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(1-pyrazin-2-ylethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(pyrazolo[1,5-a]pyridin-7-ylmethoxy)-1H-benzotriazole;
4-[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]benzonitrile;
4-bromo-1-(2,2-dimethylpropyl)-5-(pyrimidin-2-ylmethoxy)-1H-benzotriazole;
4-bromo-5-[(6-chloropyrazin-2-yl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
Ethyl {[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}(phenyl)acetate;
4-bromo-1-(2,2-dimethylpropyl)-5-(1,3-oxazol-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(1R)-1-pyridin-2-ylethoxy]-1H-benzotriazole;
methyl 6-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridine-3-carboxylate;
methyl 6-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridine-2-carboxylate;
4-bromo-1-(2,2-dimethylpropyl)-5-[(1R)-1-phenylethoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(pyridin-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(1S)-1-phenylethoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(1-phenylpropoxy)-1H-benzotriazole;
4-chloro-1-(2,2-dimethylpropyl)-5-(pyrazin-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(6-fluoropyrazin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[cyclopropyl(4-fluorophenyl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[1-(4-bromophenyl)ethoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(4-methyl-2-phenylpyrimidin-5-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[(6-chloropyridin-3-yl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[(3,5-dimethyl-4-nitropyridin-2-yl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[(4-chloropyridin-2-yl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(6-piperidin-1-ylpyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[(6-bromopyridin-2-yl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[(5-bromopyridin-2-yl)methoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(2-methylpyridin-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(4-methoxy-3,5-dimethylpyridin-2-yl)methoxy]-1H-benzotriazole;
5-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)pyrimidine-2,4-diol;
5-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridin-2-amine;
N-[3-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridin-2-yl]-2,2-dimethylpropanamide;
4-bromo-1-(2,2-dimethylpropyl)-5-(1-pyridin-4-ylethoxy)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(1-oxidopyridin-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(1-oxidopyridin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(pyridin-4-ylmethoxy)-1H-benzotriazole;
4-bromo-5-[1-(4-bromophenyl)-2,2,2-trifluoroethoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(3-fluoropyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[(2-bromobenzyl)oxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(2-fluorobenzyl)oxy]-1H-benzotriazole;
4-bromo-5-[(2-chlorobenzyl)oxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[(2,4-dichlorobenzyl)oxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[(2,5-dichlorobenzyl)oxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-{[2-(trifluoromethyl)benzyl]oxy}-1H-benzotriazole;
4-bromo-5-[1-(4-bromophenyl)ethoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-5-[1-(4-bromophenyl)ethoxy]-1-(2,2-dimethylpropyl)-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-[(2-methylpyridin-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(2,2-dimethylpropyl)-5-(1-pyridin-4-ylethoxy)-1H-benzotriazole;
methyl 6-({[4-bromo-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridine-2-carboxylate;
4-bromo-1-(2,2-dimethylpropyl)-5-[(2-methyl-1,3-thiazol-4-yl)methoxy]-1H-benzotriazole;
{[4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}acetonitrile;
4-Bromo-1-(cyclopropylmethyl)-5-[(6-methoxypyridin-2-yl)methoxy]-1H-benzotriazole;
1-{[4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3,3-dimethylbutan-2-one;
1-{[4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3,3-dimethylbutan-2-ol;
1-{[4-Bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N-hydroxy-3,3-dimethylbutan-2-imine;
tert-butyl-4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-hydroxypiperidine-1-carboxylate;
tert-butyl-4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-fluoropiperidine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-{[3-fluoropiperidin-4-yl]oxy}-1-H-benzotriazole;
5-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-1,3-oxazolidin-2-one;
4-bromo-1-(cyclopropylmethyl)-5-(pyridin-4-ylmethoxy)-1H-benzotriazole;
5-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-3-(2,2,2-trifluoroethyl)-1,3-oxazolidin-2-one;
4-bromo-1-(cyclopropylmethyl)-5-{[(3R,4R)-3-fluoro-1-(2,2,2-trifluoroethyl)piperidin-4-yl]oxy}-1H-benzotriazole;
tert-butyl (3S,4R)-4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-fluoropiperidine-1-carboxylate;
tert-butyl 4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-3,6-dihydropyridine-1(2H)-carboxylate;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-morpholin-4-ylpropan-2-ol;
tert-butyl[1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-hydroxypropyl)piperidin-4-yl]carbamate;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-hydroxypropyl)piperidine-4-carbonitrile;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-(4-methoxypiperidin-1-yl)propan-2-ol;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-(4-fluoropiperidin-1-yl)propan-2-ol;
tert-butyl (3S,4S)-3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-4-hydroxypiperidine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2,2-difluoroethyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
5-[(1-acetylpiperidin-4-yl)methoxy]-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2-methylpropanoyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-propanoylpiperidin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(methoxyacetyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-5-{[1-(cyclopropylcarbonyl)piperidin-4-yl]methoxy}-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(trifluoroacetyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2,2,2-trifluoroethyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-pyrrolidin-1-ylpropan-2-ol;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-[4-(methylsulfonyl)piperazin-1-yl]propan-2-ol;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-[4-(ethylsulfonyl)piperazin-1-yl]propan-2-ol;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-[4-(2,2-dimethylpropanoyl)piperazin-1-yl]propan-2-ol;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-hydroxypropyl)piperidin-4-ol;
1-(4-acetylpiperazin-1-yl)-3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propan-2-ol;
benzyl 4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-hydroxypropyl)piperazine-1-carboxylate;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-[4-(phenylcarbonyl)piperazin-1-yl]propan-2-ol;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-[4-(phenylsulfonyl)piperazin-1-yl]propan-2-ol;
tert-butyl 4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-hydroxypropyl)-1,4-diazepane-1-carboxylate;
1-azetidin-1-yl-3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propan-2-ol;
3-[4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)piperidin-1-yl]-3-oxopropanenitrile;
tert-butyl (3S,4S)-4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-3,4-dihydroxypiperidine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-[(1-methylpiperidin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-ethylpiperidin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-propylpiperidin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2,2-dimethylpropyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(1-methylethyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
tert-butyl 4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}piperidine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(3,3,3-trifluoropropyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2,2,3,3-tetrafluoropropyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(trifluoroacetyl)piperidin-4-yl]oxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2,2-difluoroethyl)piperidin-4-yl]oxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(3,3,3-trifluoropropanoyl)piperidin-4-yl]oxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(2,2,2-trifluoroethyl)piperidin-4-yl]oxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-({1-[(trifluoromethyl)sulfonyl]piperidin-4-yl}methoxy)-1H-benzotriazole;
tert-butyl 3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-4-oxopiperidine-1-carboxylate;
tert-butyl (3R,4R)-4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-hydroxypiperidine-1-carboxylate;
tert-butyl (3R,4R)-4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-3-hydroxypiperidine-1-carboxylate;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}cycloheptanone;
3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl acetate;
methyl 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}butanoate;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-thiazol-4-ylmethoxy)-1H-benzotriazole;
methyl 4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}butanoate;
5-(1H-benzotriazol-1-ylmethoxy)-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(ethoxymethoxy)-1H-benzotriazole;
{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl 2,2-dimethylpropanoate;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N-methoxy-N-methylacetamide;
4-bromo-1-(cyclopropylmethyl)-5-[(3,5-dimethylisoxazol-4-yl)methoxy]-1H-benzotriazole;
5-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}pentan-2-one;
ethyl 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-methylpropanoate;
tert-butyl {[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}acetate;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-dioxolan-2-ylmethoxy)-1H-benzotriazole;
methyl 4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-methylbutanoate;
4-bromo-1-(cyclopropylmethyl)-5-(tetrahydro-2H-pyran-4-yloxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(tetrahydrofuran-3-yloxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(isothiazol-3-ylmethoxy)-1H-benzotriazole;
3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}azepan-2-one;
4-bromo-1-(cyclopropylmethyl)-5-[(1-methyl-1H-1,2,4-triazol-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,4-dioxan-2-ylmethoxy)-1H-benzotriazole;
4-bromo-5-[(6-chloropyridazin-3-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(imidazo[1,2-a]pyrimidin-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(1,3-dioxolan-2-yl)ethoxy]-1H-benzotriazole;
tert-butyl 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propanoate;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N-(1-methylethyl)acetamide;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}cyclohexanone;
4-bromo-1-(cyclopropylmethyl)-5-[(1-ethyl-1H-imidazol-2-yl)methoxy]-1H-benzotriazole;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N,N-diethylacetamide;
4-bromo-1-(cyclopropylmethyl)-5-[(4-methyl-1,3-thiazol-5-yl)methoxy]-1H-benzotriazole;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N-tert-butylacetamide;
4-bromo-1-(cyclopropylmethyl)-5-[2-(1,3-dioxan-2-yl)ethoxy]-1H-benzotriazole;
{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl butanoate;
[6-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridin-2-yl]methanol;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-methylpropanamide;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}cyclopentanone;
ethyl 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3-methylbutanoate;
4-bromo-5-(but-3-en-1-yloxy)-1-(cyclopropylmethyl)-1H-benzotriazole;
4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}butane-1,2-diol;
4-bromo-1-(cyclopropylmethyl)-5-[3-(4,4-difluoropiperidin-1-yl)propoxy]-1H-benzotriazole;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-1-pyridin-2-ylethanone;
4-bromo-1-(cyclopropylmethyl)-5-{[2-(1-methylethyl)-1,3-thiazol-4-yl]methoxy}-1H-benzotriazole;
tert-butyl 4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}butanoate;
4-bromo-1-(cyclopropylmethyl)-5-(3-morpholin-4-ylpropoxy)-1H-benzotriazole;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3,3-dimethylbutan-2-one;
3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propan-1-ol;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-3-methylimidazolidine-2,4-dione;
4-bromo-1-(cyclopropylmethyl)-5-[(5-methylimidazo[1,2-a]pyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[(3-tert-butyl-1,2,4-oxadiazol-5-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-5-[(5-tert-butyl-1,3,4-oxadiazol-2-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N,N-dimethylbutanamide;
4-bromo-1-(cyclopropylmethyl)-5-[(3-methylpyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(5-ethyl-1,3,4-oxadiazol-2-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[2-(1-methylethyl)-1,3-oxazol-4-yl]methoxy}-1H-benzotriazole;
4-bromo-5-[(2-chloro-1,3-thiazol-5-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(4-methyl-1,3-thiazol-2-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[4-(1H-pyrazol-1-yl)benzyl]oxy}-1H-benzotriazole;
N-(4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}cyclohexyl)acetamide;
4-bromo-1-(cyclopropylmethyl)-5-{[(2S)-2-methoxycyclohexyl]oxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[3-(1,1-dioxidothiomorpholin-4-yl)propoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(4-methoxypyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[3-(4-bromo-1H-pyrazol-1-yl)propoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(6-methoxypyridin-2-yl)methoxy]-1H-benzotriazole;
N-[5-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridin-2-yl]-2,2-dimethylpropanamide;
4-bromo-5-[(2-chloro-5-fluoropyridin-3-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[6-(1H-pyrazol-1-yl)pyridin-3-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(prop-2-en-1-yloxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-methoxyethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(tetrahydro-2H-pyran-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(pyridin-4-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(2-methylpyridin-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(thiophen-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-methyl-1H-pyrazol-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1H-imidazol-4-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(tetrahydro-2H-pyran-3-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,4-dioxan-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-oxazol-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-oxazol-5-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-methyl-1H-imidazol-2-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(thiophen-3-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-fluoro-1-(fluoromethyl)ethoxy]-1H-benzotriazole;
3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propane-1,2-diol;
4-bromo-1-(cyclopropylmethyl)-5-(2-ethoxyethoxy)-1H-benzotriazole;
2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl acetate;
ethyl 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}butanoate;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-thiazol-2-ylmethoxy)-1H-benzotriazole;
4-bromo-5-(cyclobutylmethoxy)-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(3-methoxypropoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(furan-3-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(3,4-dihydro-2H-pyran-2-ylmethoxy)-1H-benzotriazole;
methyl 3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2,2-dimethylpropanoate;
4-bromo-1-(cyclopropylmethyl)-5-[2-(1H-imidazol-1-yl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(4-methyl-1,3-thiazol-5-yl)ethoxy]-1H-benzotriazole;
methyl 2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propanoate;
4-bromo-5-[(6-chloropyridin-3-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(5-methyl-1,3-dioxan-5-yl)methoxy]-1H-benzotriazole;
methyl (2S)-3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-2-methylpropanoate;
4-bromo-1-(cyclopropylmethyl)-5-[(6-methylpyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-5-[(2-chloropyridin-3-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-morpholin-4-ylpropoxy)-1H-benzotriazole;
(5S)-5-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)dihydrofuran-2(3H)-one;
4-bromo-1-(cyclopropylmethyl)-5-(1-pyridin-2-ylethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(1-methylethoxy)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(1-methylpyrrolidin-2-yl)ethoxy]-1H-benzotriazole;
ethyl {[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}acetate;
4-bromo-1-(cyclopropylmethyl)-5-(2,2-dimethoxyethoxy)-1H-benzotriazole;
5-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}pentan-2-one;
4-bromo-1-(cyclopropylmethyl)-5-[(1-propyl-1H-1,2,4-triazol-5-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(isoxazol-3-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(isoxazol-4-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{3-[(2S)-tetrahydrofuran-2-yl]propoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-isoxazol-4-ylethoxy)-1H-benzotriazole;
3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}pyrrolidin-2-one;
4-bromo-1-(cyclopropylmethyl)-5-(oxetan-3-yloxy)-1H-benzotriazole;
3-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}pyrrolidin-1-yl)propanenitrile;
4-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)morpholin-3-one;
4-bromo-1-(cyclopropylmethyl)-5-[(3-prop-2-en-1-yloxetan-3-yl)methoxy]-1H-benzotriazole;
7-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}Spiro[2.5]octan-4-one;
4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}cyclohexanecarbonitrile;
4-bromo-1-(cyclopropylmethyl)-5-(imidazo[1,2-a]pyridin-3-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(3-ethylisoxazol-5-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(tetrahydro-2H-pyran-4-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2,2-difluoroethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(3-ethyloxetan-3-yl)methoxy]-1H-benzotriazole;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)pyrrolidine-2,5-dione;
4-bromo-1-(cyclopropylmethyl)-5-[(3R)-tetrahydro-2H-pyran-3-ylmethoxy]-1H-benzotriazole;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)imidazolidine-2,4-dione;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)-3-methylimidazolidine-2,4-dione;
ethyl N-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)glycinate;
4-bromo-1-(cyclopropylmethyl)-5-[2-(methylsulfanyl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(3-methyloxetan-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2,3-dimethoxypropoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{[(3S)-3-methoxybutyl]oxy}-1H-benzotriazole;
methyl {[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}acetate;
4-bromo-1-(cyclopropylmethyl)-5-(pyridin-2-ylmethoxy)-1H-benzotriazole;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)imidazolidin-2-one;
(5R)-5-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyrrolidin-2-one;
4-bromo-1-(cyclopropylmethyl)-5-[(3-methoxybenzyl)oxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-oxidopyridin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-pyridin-2-ylethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(pyrimidin-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(3-fluoropyridin-2-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(isoxazol-5-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(tetrahydrofuran-2-ylmethoxy)-1H-benzotriazole;
4-bromo-5-[(2-chloropyridin-4-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-5-[(2-chloro-1,3-thiazol-5-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(5-methylisoxazol-3-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-methyl-1H-imidazol-5-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(methylsulfonyl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(methylsulfinyl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-ethoxy-1-methylethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(4H-1,2,4-triazol-4-yl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-methyl-1H-1,2,4-triazol-5-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(1-ethyl-1H-imidazol-5-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-thiazol-5-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,3-dioxolan-4-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(furan-2-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-methoxy-1-methylethoxy)-1H-benzotriazole;
4-bromo-5-[(4-chloropyridin-2-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(4,4-difluoropiperidin-1-yl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{2-[4-(trifluoromethyl)piperidin-1-yl]ethoxy}-1H-benzotriazole;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)piperidine-4-carbonitrile;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)-4-fluoropiperidine-4-carbonitrile;
4-bromo-1-(cyclopropylmethyl)-5-[2-(3,3-difluoropyrrolidin-1-yl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{2-[(3R,4R)-3,4-difluoropyrrolidin-1-yl]ethoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{2-[4-(2,2,2-trifluoroethyl)piperazin-1-yl]ethoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{2-[2-(trifluoromethyl)piperidin-1-yl]ethoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(3,3-difluoropiperidin-1-yl)ethoxy]-1H-benzotriazole;
5-[2-(4-benzyl-4-fluoropiperidin-1-yl)ethoxy]-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)-4-phenylpiperidine-4-carbonitrile;
ethyl 1-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)-4-fluoropiperidine-4-carboxylate;
5-[2-(4-acetylpiperazin-1-yl)ethoxy]-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
4-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)piperazin-2-one;
4-bromo-1-(cyclopropylmethyl)-5-(2-morpholin-4-ylethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{2-[4-(methylsulfonyl)piperazin-1-yl]ethoxy}-1H-benzotriazole;
4-bromo-5-(2-tert-butoxyethoxy)-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[2-(cyclopropyloxy)ethoxy]-1H-benzotriazole;
4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-N,N-dimethylbutanamide;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-4,4-dimethylpentan-2-one;
N-[4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-1,3-thiazol-2-yl]acetamide;
4-bromo-1-(cyclopropylmethyl)-5-{[3-(trifluoromethoxy)benzyl]oxy}-1H-benzotriazole;
tert-butyl (2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)carbamate;
4-bromo-1-(cyclopropylmethyl)-5-[(1,3-dimethyl-1H-pyrazol-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(3-methylpyridin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(pyridin-3-ylmethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[(2,6-dichloropyridin-4-yl)methoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-pyridin-4-ylethoxy)-1H-benzotriazole;
methyl 5-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)-1H-imidazole-4-carboxylate;
ethyl 4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}cyclohexanecarboxylate;
4-bromo-1-(cyclopropylmethyl)-5-[(5,6-dichloropyridin-3-yl)methoxy]-1H-benzotriazole;
5-[(1-benzyl-1H-imidazol-5-yl)methoxy]-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
4-bromo-5-[(5-bromopyridin-3-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
tert-butyl (2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)methylcarbamate;
4-bromo-5-[(6-bromopyridin-2-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
tert-butyl 3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}piperidine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-{[5-(trifluoromethyl)pyridin-2-yl]methoxy}-1H-benzotriazole;
methyl 6-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyridine-2-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-[(tetrahydro-2H-pyran-2-ylmethoxy)methyl]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-ethoxy-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[3-(4,4-difluoropiperidin-1-yl)propoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{3-[(3S)-3-fluoropyrrolidin-1-yl]propoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(3-piperidin-1-ylpropoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{3-[(3S,4S)-3,4-difluoropyrrolidin-1-yl]propoxy}-1H-benzotriazole;
4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)piperazin-2-one;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-4-phenylpiperidine-4-carbonitrile;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)piperidine-4-carbonitrile;
4-bromo-1-(cyclopropylmethyl)-5-[3-(3-fluoropiperidin-1-yl)propoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{3-[3-(fluoromethyl)pyrrolidin-1-yl]propoxy}-1H-benzotriazole;
ethyl 1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-4-fluoropiperidine-4-carboxylate;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-4-fluoropyrrolidin-3-ol;
4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-1-methylpiperazin-2-one;
4-bromo-1-(cyclopropylmethyl)-5-[3-(4,4-dimethylpiperidin-1-yl)propoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[3-(3,3-difluoropiperidin-1-yl)propoxy]-1H-benzotriazole;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-4-pyridin-2-ylpiperidine-4-carbonitrile;
1-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)-4-fluoropiperidine-4-carbonitrile;
4-bromo-1-(cyclopropylmethyl)-5-{3-[4-(trifluoromethyl)piperidin-1-yl]propoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-1H-benzotriazole;
5-[3-(4-acetylpiperazin-1-yl)propoxy]-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
(2Z)-1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3,3-dimethylbutan-2-one oxime;
1-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}-3,3-dimethylbutan-2-ol;
4-bromo-1-(cyclopropylmethyl)-5-[2-(1H-pyrazol-1-yl)ethoxy]-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(2-methoxybutoxy)-1H-benzotriazole;
1-methylethyl {[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}acetate;
4-bromo-1-(cyclopropylmethyl)-5-(3-pyridin-2-ylpropoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1-methyl-2-morpholin-4-ylethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(3-pyridin-3-ylpropoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-(1,4-dioxaspiro[4.5]dec-8-yloxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-[3-(1H-imidazol-1-yl)propoxy]-1H-benzotriazole;
4-bromo-5-[(2-bromo-1,3-thiazol-4-yl)methoxy]-1-(cyclopropylmethyl)-1H-benzotriazole;
5-(benzyloxy)-1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazole;
1-(2,2-dimethylpropyl)-5-(pyrazin-2-ylmethoxy)-1H-benzotriazole-4-carbonitrile;
3′-({[4-cyano-1-(2,2-dimethylpropyl)-1H-benzotriazol-5-yl]oxy}methyl)-4-hydroxybiphenyl-3-carboxylic acid;
5-{[3-(2-cyanopyrimidin-5-yl)benzyl]oxy}-1-(2,2-dimethylpropyl)-1H-benzotriazole-4-carbonitrile;
1-(cyclopropylmethyl)-5-methoxy-1H-benzotriazole-4-carbonitrile;
4-bromo-1-(cyclopropylmethyl)-5-(3-piperazin-1-ylpropoxy)-1H-benzotriazole;
(2S)-1-[4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)piperazin-1-yl]-1-oxopropan-2-ol;
4-bromo-1-(cyclopropylmethyl)-5-{3-[4-(methylsulfonyl)piperazin-1-yl]propoxy}-1H-benzotriazole;
5-[3-(4-acetylpiperazin-1-yl)propoxy]-4-bromo-1-(cyclopropylmethyl)-1H-benzotriazole;
tert-butyl 4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)piperazine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-(2-piperazin-1-ylethoxy)-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{2-[4-(methylsulfonyl)piperazin-1-yl]ethoxy}-1H-benzotriazole;
tert-butyl 4-({[4-chloro-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)piperidine-1-carboxylate;
4-bromo-1-(cyclopropylmethyl)-5-{[1-(isoxazol-3-ylcarbonyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
(2S)-1-[4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)piperidin-1-yl]-1-oxopropan-2-ol;
tert-butyl 3-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)piperidine-1-carboxylate;
tert-butyl 3-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyrrolidine-1-carboxylate;
tert-butyl (2R)-2-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyrrolidine-1-carboxylate;
tert-butyl 3-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)azetidine-1-carboxylate;
tert-butyl 4-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)piperidine-1-carboxylate;
4-chloro-1-(cyclopropylmethyl)-5-{[1-(isoxazol-3-ylcarbonyl)piperidin-4-yl]methoxy}-1H-benzotriazole;
4-bromo-1-(cyclopropylmethyl)-5-{3-[4-(isoxazol-3-ylcarbonyl)piperazin-1-yl]propoxy}-1H-benzotriazole;
4-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}butan-2-ol;
tert-butyl (2S)-2-({[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}methyl)pyrrolidine-1-carboxylate;
tert-butyl 4-(2-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}ethyl)piperazine-1-carboxylate;
tert-butyl 4-(3-{[4-bromo-1-(cyclopropylmethyl)-1H-benzotriazol-5-yl]oxy}propyl)piperazine-1-carboxylate;
4-chloro-1-(cyclopropylmethyl)-5-{[1-(isoxazol-3-ylcarbonyl)-4-methylpiperidin-4-yl]methoxy}-1H-benzotriazole;
1-[4-({[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]oxy}methyl)-4-methylpiperidin-1-yl]-1-oxopropan-2-ol;
2-[4-({[1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazol-5-yl]oxy}methyl)-4-methylpiperidin-1-yl]-2-oxoethanol;
and
5-(Benzyloxy)-1-(cyclopropylmethyl)-4-(trifluoromethyl)-1H-benzotriazole
or a pharmaceutically acceptable salt of any of the foregoing compounds.

413 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/247,009Filed 28 Sep 2011 · us provisional application
Priority: 29 Sep 2010
Published: US 2012/0135977 A131 May 2012
Granted: 22 Jul 2014
Term ends: Not estimatedThe source records don’t support an estimate.

Classification10 codes

C07D 249/18
Condensed with carbocyclic rings or ring systems: benzotriazoles
A61P 25/00
Drugs for disorders of the nervous system
A61P 25/18
Drugs for disorders of the nervous system: antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
C07D 401/12
Containing two hetero rings: linked by a chain containing hetero atoms as chain links

Family

Application61/387,688Us provisional application · filed 29 Sep 2010
US 2012/0135977 A1Pre-grant publication · published 31 May 2012
US 8,785,481 B2This patent

From the US filing history. Foreign family members aren’t listed.

Timeline

Citations

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