IP Library Granted Patent US 10,357,481
Granted Patent B2
US 10,357,481 · App. 15/579,878 · Granted Jul 23, 2019

Substituted triazolo bicyclic compounds as PDE2 inhibitors

Inventors: Gregori J. Morriello (Rahway, NJ); Lehua Chang (Rahway, NJ); Ashley Forster (Rahway, NJ); Yili Chen (Rahway, NJ); Michael P. Dwyer (Rahway, NJ); Zack Zhiqiang Guo (Rahway, NJ); Ming Wang (Rahway, NJ); Shimin Xu (Beijing, CN); Yingjian Bo (Beijing, CN); Jianmin Fu (Beijing, CN)
Assignee: Merck Sharp & Dohme Corp.
A61K31/4196A61K31/52A61P25/06A61P25/16A61P25/18A61P25/22A61P25/28C07D471/04C07D487/04
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Quick Facts
Patent No.
US 10,357,481
App. No.
15/579,878
Granted
Jul 23, 2019
Kind
B2
Abstract

The present invention is directed to substituted triazolo bicyclic compounds of formula I which are useful as therapeutic agents for the treatment of central nervous system disorders associated with phosphodiesterase 2 (PDE2). The present invention also relates to the use of such compounds for treating neurological and psychiatric disorders, such as schizophrenia, psychosis, Parkinson's disease, Parkinson's disease dementia (PDD), or Huntington's disease, and those associated with striatal hypofunction or basal ganglia dysfunction.

Claims (307)

1. A compound represented by structural formula Ia

or a pharmaceutically acceptable salt thereof, wherein:

one of R 1 and R 2 is H and the other is C 1-6 alkyl, said alkyl optionally substituted with 1 to 3 groups R a ;

or R 1 and R 2 can combine with the carbon to which they are attached to form C 3-10 cycloalkyl or C 3-10 -heterocycloalkyl selected from the group consisting of cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and oxetanyl, said cycloalkyl and heterocycloalkyl optionally substituted with 1 to 3 groups R a ;

R 4a is selected from the group consisting of H, CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 20 H, C(CH 3 ) 3 , CH 2 CH 3 , CH(CH 3 )OH, (CH 2 ) n OH, CHF 2 , CH 2 F, CF 3 , CF 2 CF 3 , NH 2 , N(CH 3 ) 2 , NHCH 3 , OCH 2 CH 3 , (CH 2 ) n OCH 3 , halo and optionally substituted cyclopropyl;

Rob is hydrogen or CH3;

R a is selected from the group consisting of halo, CN, C 1-6 alkyl, (CH 2 ) n OR, (O) p C 1-4 haloalkyl, NR 2 , SCF 3 , and SF 5 , said alkyl optionally substituted with one to three groups selected from halo, wherein halo is selected from the group consisting of fluorine and chlorine, and C 1-6 alkyl; or

two adjacent R a groups on the phenyl together with the atoms to which they are attached can combine to form a cyclic ring, said ring optionally interrupted by 1 to 2 heteroatoms selected from N, S, and O;

R represents H or C 1-6 alkyl,

n represents 0, 1, 2, 3, or 4;

p represents 0 or 1.

2. The compound according to claim 1 or a pharmaceutically acceptable salt thereof wherein one of R 1 and R 2 is H and the other is selected from the group consisting CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 2 OH, C(CH 3 ) 2 CH 2 OH, C(CH 3 ) 3 , CH 2 CH 3 , CH(CH 3 )OH, (CH 2 ) n OH, C(CH 3 ) 2 NH 2 , C(CH 2 CH 3 ) 2 OH, N(CH 3 ) 2 , NHCH 3 , OCH 2 CH 3 , and (CH 2 ) n OCH 3 .

3. The compound according to claim 1 or a pharmaceutically acceptable salt thereof wherein R a is selected from halo, (CH 2 ) n CF 3 , OCF 3 , C(CH 3 ) 3 , CHF 2 , SF 5 , SCF 3 , OCHF 2 , CH(CH 3 ) 2 , or when two adjacent R a on the phenyl along with the atoms to which they are attached combine the combination of two R a is selected from cyclopropyl or pyridyl, said cyclopropyl and pyridyl optionally substituted with 1 to 3 groups of C 1-6 alkyl,

X, Y and Z, respectively, represents X=N, Y=CR 4a , Z=CR 4b , wherein R 4a and R 4b are selected from the group consisting of H, CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 2 OH, C(CH 3 ) 3 , CH 2 CH 3 , CH(CH 3 )OH, (CH 2 ) n OH, CHF 2 , CH 2 F, CF 3 , CF 2 CF 3 , NH 2 , N(CH 3 ) 2 , NHCH 3 , OCH 2 CH 3 , (CH 2 ) n OCH 3 , halo and optionally substituted cyclopropyl, and

one of R 1 and R 2 is H and the other is selected from the group consisting H, CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 2 OH, C(CH 3 ) 2 CH 2 OH, C(CH 3 ) 3 , CH 2 CH 3 , CH(CH 3 )OH, (CH 2 ) n OH, C(CH 3 ) 2 NH 2 , C(CH 2 CH 3 ) 2 OH, N(CH 3 ) 2 , NHCH 3 , OCH 2 CH 3 , and (CH 2 ) n OCH 3 .

4. The compound according to 36 or a pharmaceutically acceptable salt thereof wherein R a is selected from the group consisting of halo, (CH2)nCF3, and OCF3, one of R 4a and R 4b is hydrogen or CH 3 and the other is selected from the group consisting of H, CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 2 OH, C(CH 3 ) 3 , CH 2 CH 3 , CH(CH 3 )OH, (CH 2 ) n OH, CHF 2 , CH 2 F, CF 3 , CF2CF 3 , NH 2 , N(CH 3 ) 2 , NHCH 3 , OCH 2 CH 3 , (CH 2 ) n OCH 3 , halo and optionally substituted cyclopropyl, and one of R 1 and R 2 is hydrogen and the other is selected from the group consisting of CH 3 , CH(CH 3 ) 2 , C(CH 3 ) 2 OH, C(CH 3 ) 3 , (CH 2 ) n OH, and (CH 2 ) n OCH 3 .

5. The compound according to claim 3 or a pharmaceutically acceptable salt thereof wherein R a is selected from the group consisting of fluorine, chlorine, CF 3 , and OCF 3 , one of R 4a and R 4b is hydrogen and the other is selected from the group consisting of CH 3 , (CH 2 ) n OH, and CF 3 , and one of R 1 and R 2 is hydrogen and the other is CH 3 .

6. The compound according to claim 3 or a pharmaceutically acceptable salt thereof wherein R a is selected from the group consisting of fluorine, chlorine, CF 3 , and OCF 3 , one of R 4a and R 4b is hydrogen and the other is selected from the group consisting of CH 3 , (CH 2 ) n OH, and CF 3 , and R 1 and R 2 combine with the carbon to which they are attached to form optionally substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or oxetanyl.

7. A compound which is:

5-Methyl-N-{(1R)-1-[4-(trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1S)-1-[4-(trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]ethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-1-[4-(2,2,2-trifluoroethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Chloro-4-(trifluoromethyl)phenyl]ethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[2,5-Difluoro-4-(trifluoromethyl)phenyl]ethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-1-[4-(trifluoromethoxy)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]ethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Chloro-4-(trifluoromethoxy)phenyl]ethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-[(1R)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}ethyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[(1R)-1-{3-Fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}ethyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-1-[4-(1-methylethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[(1R)-1-(4-Cyclopropyl-3-fluorophenyl)ethyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-1-[4-(1-methylcyclopropyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]propyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-[(1R)-1-{4-[(trifluoromethyl)sulfanyl]phenyl}propyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[(1R)-1-{3-Fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}propyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-2-methyl-1-[4-(trifluoromethyl)phenyl]propyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl}-2-methylpropyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[(1R)-1-{3-Fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}-2-methylpropyl]-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-2-methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[4-(Difluoromethoxy)phenyl]-2-methylpropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-2-methyl-1-[4-(1-methylcyclopropyl)phenyl]propyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[(1R)-1-(4-Cyclopropyl-3-fluorophenyl)-2-methylpropyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-2,2-Dimethyl-1-[4-(trifluoromethyl)phenyl]propyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2,2-dimethylpropyl}-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

N-[(1R)-2,2-Dimethyl-1-{4-[(trifluoromethyl)sulfanyl]phenyl}propyl]-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

N-[(1R)-1-(4-Cyclopropylphenyl)-2,2-dimethylpropyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[(1R)-1-(4-Cyclopropyl-3-fluorophenyl)-2,2-dimethylpropyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-2,2-Dimethyl-1-[4-(trifluoromethoxy)phenyl]propyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[4-(Difluoromethoxy)phenyl]-2,2-dimethylpropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-2,2-Dimethyl-1-[4-(2,2,2-trifluoroethyl)phenyl]propyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-2,2-Dimethyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—{(R)-Cyclopropyl[4-(pentafluoro-λ 6 -sulfanyl)phenyl]methyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—[(R)-Cyclopropyl(4-cyclopropyl-3-fluorophenyl)methyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—{(R)-Cyclopropyl[3-fluoro-4-(trifluoromethyl)phenyl]methyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—[(R)-Cyclopropyl{4-[(trifluoromethyl)sulfanyl]phenyl}methyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—[(R)-Cyclopropyl{3-fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}methyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—[(R)-Cyclopropyl(4-cyclopropylphenyl)methyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—[(R)-[3-Fluoro-4-(trifluoromethyl)phenyl](1-methylcyclopropyl)methyl]-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

5-Methyl-N—{(R)-(1-methylcyclopropyl)[4-(pentafluoro-λ 6 -sulfanyl)phenyl]methyl}[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-1-methylethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]-1-methylethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[2-Chloro-4-(trifluoromethyl)phenyl]-1-methylethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[2-Methoxy-4-(trifluoromethyl)phenyl]-1-methylethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-methyl-1-[4-(trifluoromethoxy)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-(1-{3-Fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}-1-methylethyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-1-methylethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[2-Fluoro-4-(trifluoromethyl)phenyl]-1-methylethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-methyl-1-[4-(trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-methyl-1-[2-methyl-4-(trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-(1-methyl-1-{4-[(trifluoromethyl)sulfanyl]phenyl}ethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-[4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-(1-{4-[(trifluoromethyl)sulfanyl]phenyl}cyclopropyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-[1-(4-tert-Butylphenyl)cyclopropyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethoxy)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-(1-{3-Fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}cyclopropyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-[4-(trifluoromethyl)phenyl]cyclobutyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-(1-{4-[(trifluoromethyl)sulfanyl]phenyl}cyclobutyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-(1-{3-Fluoro-4-[(trifluoromethyl)sulfanyl]phenyl}cyclobutyl)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{1-[4-(trifluoromethyl)phenyl]cyclopentyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Ethyl-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Cyclopropyl-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Cyclopropyl-N-{1-[3-fluoro-4-(trifluoromethoxy)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Cyclopropyl-N-{1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-tert-Butyl-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-(pentafluoroethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-(methoxymethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-(methoxymethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]ethyl}-5-(methoxymethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

[7-({1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]methanol,

[7-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}amino)[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]methanol,

[7-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]ethyl}amino)[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]methanol,

5-(Fluoromethyl)-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[4-(Trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[4-(Trifluoromethoxy)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5,6-Dimethyl-N-{(1S)-1-[4-(trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5,6-Dimethyl-N-{(1R)-1-[4-(trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5,6-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

2-[(5-Methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-[4-(trifluoromethyl)phenyl]ethanol,

(1S,2R)-1-[(5-Methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

(1S,2S)-1-[(5-Methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

(1S)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(trifluoromethyl) phenyl]propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(trifluoromethyl) phenyl]propan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(trifluoromethoxy) phenyl]propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(trifluoromethoxy) phenyl]propan-2-ol,

(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[2-Chloro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[2-Chloro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[3-Chloro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[3-Chloro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[2-Chloro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-[2-Chloro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-(4-tert-Butylphenyl)-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-(4-tert-Butylphenyl)-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[4-(Difluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]propan-2-ol,

(1R)-1-[4-(Difluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]propan-2-ol,

(1S)-1-[4-(Difluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-[4-(Difluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-(2,2-Difluoro-1,3-benzodioxol-5-yl)-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-(2,2-Difluoro-1,3-benzodioxol-5-yl)-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(2,2,2-trifluoroethyl)phenyl]propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[4-(2,2,2-trifluoroethyl)phenyl]propan-2-ol,

(1S)-2-Methyl-1-[4-(1-methylcyclopropyl)phenyl]-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-2-Methyl-1-[4-(1-methylcyclopropyl)phenyl]-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-naphthalen-2-yl propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-naphthalen-2-yl propan-2-ol,

(1S)-2-Methyl-1-(1-methyl-1H-indol-2-yl)-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]propan-2-ol,

(1R)-2-Methyl-1-(1-methyl-1H-indol-2-yl)-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]propan-2-ol,

(1S)-1-Biphenyl-4-yl-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-Biphenyl-4-yl-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-methyl-4-(trifluoromethoxy)phenyl]propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-methyl-4-(trifluoromethoxy)phenyl]propan-2-ol,

(1S)-1-[4-fluoro-3-(Trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1R)-1-[4-fluoro-3-(Trifluoromethoxy)phenyl]-2-methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(1S)-1-[(2,5-Dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1R)-1-[(2,5-Dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1S)-1-[(2,5-Dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1R)-1-[(2,5-Dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1S)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1R)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1S)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1R)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1S)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propan-2-ol,

(1R)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propan-2-ol,

(4R)-4-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-4-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]butan-2-ol,

(4S)-4-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-4[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]butan-2-ol,

(3R)-2-Methyl-3-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-3[4-(trifluoromethoxy) phenyl]butan-2-ol,

(3S)-2-Methyl-3-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-3-[4-(trifluoromethoxy) phenyl]butan-2-ol,

(1S)-2-Methyl-1-{[5-(1-methylethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

(1S)-1-[(5-Cyclopropyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-methyl-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

(1S)-1-[(5-tert-Butyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-2-methyl-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

(1S)-1-[2-Chloro-4-(trifluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[2-Chloro-4-(trifluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-(4-tert-Butylphenyl)-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-(4-tert-Butylphenyl)-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[4-(Difluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[4-(Difluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[4-(Difluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[4-(Difluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-(2,2-Difluoro-1,3-benzodioxol-5-yl)-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-(2,2-Difluoro-1,3-benzodioxol-5-yl)-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-2-Methyl-1-[4-(2,2,2-trifluoroethyl)phenyl]-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-2-Methyl-1-[4-(2,2,2-trifluoroethyl)phenyl]-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[2-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-2-Methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-2-Methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-2-Methyl-1-[4-(1-methylcyclopropyl)phenyl]-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-2-Methyl-1-[4-(1-methylcyclopropyl)phenyl]-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(R)-1-[4-(Difluoromethoxy)-2-fluorophenyl]-1-{[5-(difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-2-methylpropan-2-ol,

(S)-1-[4-(Difluoromethoxy)-2-fluorophenyl]-1-{[5-(difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-2-methylpropan-2-ol,

(R)-1-[2-Chloro-4-(difluoromethoxy)phenyl]-1-{[5-(difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-2-methylpropan-2-ol,

(S)-1-[2-Chloro-4-(difluoromethoxy)phenyl]-1-{[5-(difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-2-methylpropan-2-ol,

(R)-1-{[5-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(S)-1-{[5-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(R)-1-{[5-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(S)-1-{[5-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(R)-1-[4-(Difluoromethoxy)-3-fluorophenyl]-1-{[5-(difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-2-methylpropan-2-ol,

(S)-1-[4-(Difluoromethoxy)-3-fluorophenyl]-1-{[5-(difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-2-methylpropan-2-ol,

2-(Fluoromethyl)-N-{(1R)-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-2,5-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

2-Ethyl-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl-2-propyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

2-Cyclopropyl-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

[7-({1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-2-yl]methanol,

2-(Fluoromethyl)-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

N-{3-[3-Fluoro-4-(trifluoromethyl)phenyl]oxetan-3-yl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine

5-Methyl-N-{3 [4-(trifluoromethyl)phenyl]oxetan-3-yl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

2-(Difluoromethyl)-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-2,5-dimethyl[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

2-Ethyl-N-{(1R)-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl-2-propyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

2-Cyclopropyl-N-{(1R)-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

[7-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}amino)-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-2-yl]methanol,

2-(Difluoromethyl)-N-{(1R)-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Chloro-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methoxyethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methoxyethyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1R)-2-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]propyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

5-Methyl-N-{(1S)-2-methyl-1-[5-(trifluoromethyl)pyridin-2-yl]propyl}[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

3-{(S)-[3-Fluoro-4-(trifluoromethyl)phenyl][(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]methyl}pentan-3-ol,

3-{(R)-[3-Fluoro-4-(trifluoromethyl)phenyl][(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]methyl}pentan-3-ol,

N-{(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methoxyethyl}-5-(trifluoromethyl) [1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methoxyethyl}-5-(trifluoromethyl) [1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

3-[(S)-[3-Fluoro-4-(trifluoromethyl)phenyl]{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}methyl]pentan-3-ol,

3-[(R)-[3-Fluoro-4-(trifluoromethyl)phenyl]{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}methyl]pentan-3-ol,

(1S)-2-Methyl-1-{4-[(trifluoromethyl)sulfanyl]phenyl}-1-{[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-2-Methyl-1-{4-[(trifluoromethyl)sulfanyl]phenyl}-1-{[5-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyrimidin-7-yl]amino}propan-2-ol,

(1R)-1-[(5-Chloro[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2-methylpropan-2-ol,

(1S)-1-[(5-Chloro[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[3-fluoro-4-(trifluoromethyl) phenyl]-2-methylpropan-2-ol,

(1S)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[6-(trifluoromethyl) pyridin-3-yl]propan-2-ol,

(1R)-2-Methyl-1-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[6-(trifluoromethyl) pyridin-3-yl]propan-2-ol,

(1S)-1-{[5-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2-methylpropan-2-ol,

(1R)-1-{[5-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2-methylpropan-2-ol,

N—[(R)-[3-Fluoro-4-(trifluoromethoxy)phenyl](oxetan-3-yl)methyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

N—[(S)-[3-Fluoro-4-(trifluoromethoxy)phenyl](oxetan-3-yl)methyl]-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

(R)-3-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2,2-dimethyl-3-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-1-ol,

(S)-3-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2,2-dimethyl-3-[(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-1-ol,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-5-methoxy[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

5-Ethoxy-N-{(1R)-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}[1,2,4]triazolo [1,5-a]pyrimidin-7-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methoxy[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-1-[(5-methoxy[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]-2-methylpropan-2-ol,

(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-1-[(5-methoxy[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) amino]-2-methylpropan-2-ol,

7-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}amino)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol,

N 7 -{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-N˜5˜,N˜5˜-dimethyl[1,2,4]triazolo [1,5-a]pyrimidine-5,7-diamine,

N 7 -{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}[1,2,4]triazolo[1,5-a]pyrimidine-5,7-diamine,

N 7 -{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-N 5 -methyl[1,2,4]triazolo [1,5-a]pyrimidine-5,7-diamine,

N 7 -{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-N 5 ,N 5 -dimethyl [1,2,4]triazolo[1,5-a]pyrimidine-5,7-diamine,

(1S)-1-{[5-(Dimethylamino)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2-methylpropan-2-ol,

(1R)-1-{[5-(Dimethylamino)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]amino}-1-[3-fluoro-4-(trifluoromethyl)phenyl]-2-methylpropan-2-ol,

3-[7-({1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]propan-1-01,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-N, 5-dimethyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,

(R)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[methyl(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

(S)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-[methyl(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]propan-2-ol,

3[7-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}amino)-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-2-yl]propan-1-ol,

2-[7-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}amino)-5-methyl [1,2,4]triazolo[1,5-a]pyrimidin-2-yl]ethanol,

2-[7-({1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)[1,2,4]triazolo[1,5-a]pyrimidin-5-yl]ethanol,

1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-M--(5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl) propane-1,2-diamine,

(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-N 1 -[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]propane-1,2-diamine,

(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-N 1 -[5-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-yl]propane-1,2-diamine,

N 7 -{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine-2,7-diamine,

N 7 -{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-N 2 ,N 2 , 5-trimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2,7-diamine,

N 7 -{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-N 2 ,5-dimethyl[1,2,4]triazolo[1,5-a]pyrimidine-2,7-diamine,

(1S)-1-[(2-Amino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)amino]-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

N-{(1R)-1-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]ethyl}[1,2,4]triazolo[5,1-a][1,2,4]triazin-4-amine,

(R)-7-{2,2-Dimethyl-1-[4-(trifluoromethyl)phenyl]propoxy}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine,

(R)-7-{2,2-Dimethyl-1-[4-(trifluoromethyl)phenyl]propoxy}-5-methyl[1,2,4]triazolo[1,5-a]pyrimidine,

5-Methyl-7-({1-[4-(trifluoromethyl)phenyl]cyclopropyl}oxy)[1,2,4]triazolo[1,5-a]pyrimidine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-amine,

N-{(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}-7-methyl[1,2,4]triazolo [1,5-a]pyridin-5-amine,

(1S)-2-Methyl-1-[(7-methyl[1,2,4]triazolo[1,5-a]pyridin-5-yl)amino]-1-[4-(trifluoromethyl) phenyl]propan-2-ol,

[5-({1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

[5-({(1R)-1-[4-(Trifluoromethyl)phenyl]ethyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

[5-({(1S)-1-[4-(Trifluoromethyl)phenyl]ethyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

[5-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]propyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

[5-({1-[2-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

[5-({(1R)-1-[4-(Trifluoromethoxy)phenyl]ethyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

[5-({(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]ethyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]methanol,

(1S)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-1-{[7-(hydroxymethyl) [1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}-2-methylpropan-2-ol,

7-(Difluoromethyl)-N-{1-[3-fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyridin-5-amine,

1-[5-({1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}amino)[1,2,4]triazolo[1,5-a]pyridin-7-yl]ethanol,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-amine,

(1S)-2-Methyl-1-[4-(trifluoromethyl)phenyl]-1-{[7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}propan-2-ol,

(1S)-1-[2-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-{[7-(trifluoromethyl)[1,2,4]triazolo [1,5-a]pyridin-5-yl]amino}propan-2-ol,

(1S)-1-{[7-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}-1-[3-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1S)-1-{[7-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}-2-methyl-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

(1S)-1-{[7-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}-1-[2-fluoro-4-(trifluoromethoxy)phenyl]-2-methylpropan-2-ol,

(1S)-1-{[7-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}-2-methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propan-2-ol,

(1R)-1-{[7-(Difluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino}-2-methyl-1-[4-(pentafluoro-λ 6 -sulfanyl)phenyl]propan-2-ol,

N{-(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2,2-dimethylpropyl}[1,2,4]triazolo[1,5-a]pyrazin-5-amine,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrazin-5-amine,

(1S)-1-[3-Fluoro-4-(trifluoromethoxy)phenyl]-2-methyl-1-([1,2,4]triazolo[1,5-a]pyrazin-5-ylamino)propan-2-ol,

(1S)-2-Methyl-1-([1,2,4]triazolo[1,5-a]pyrazin-5-ylamino)-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

N-{(1R)-1-[4-(Trifluoromethyl)phenyl]ethyl}[1,2,4]triazolo[1,5-a]pyrazin-5-amine,

N-{1-[4-(Pentafluoro-λ 6 -sulfanyl)phenyl]cyclopropyl}[1,2,4]triazolo[1,5-a]pyrazin-5-amine,

(1S)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(7-methyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)amino]propan-2-ol,

(1R)-1-[3-Fluoro-4-(trifluoromethyl)phenyl]-2-methyl-1-[(7-methyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)amino]propan-2-ol,

N-{1-[3-Fluoro-4-(trifluoromethyl)phenyl]cyclopropyl}-7-methyl[1,2,4]triazolo[1,5-a]pyrimidin-5-amine,

(1S)-14 [2-Amino-7-(trifluoromethyl)[1,2,4]triazolo[1,5-a]pyridin-5-yl]amino-2-methyl-1-[4-(trifluoromethyl)phenyl]propan-2-ol,

or a pharmaceutically acceptable salt thereof.

8. A pharmaceutical composition which comprises a pharmaceutically acceptable carrier and a compound of claim 1 or a pharmaceutically acceptable salt thereof.

Assignments (4)
MERGER Recorded Aug 8, 2022
From: MERCK SHARP & DOHME CORP.
To: MERCK SHARP & DOHME LLC
Reel/Frame 061102/0145 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2017
From: FORSTER, ASHLEY; CHANG, LEHUA; MORRIELLO, GREGORI J.; CHEN, YILI; DWYER, MICHAEL P.; GUO, ZACK ZHIQIANG; WANG, MING
To: MERCK SHARP & DOHME CORP.
Reel/Frame 044304/0679 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2017
From: XU, SHIMIN; FU, JIANMIN; BO, YINGJIAN
To: PHARMARON BEIJING CO. LTD.
Reel/Frame 044304/0736 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Dec 5, 2017
From: PHARMARON BEIJING CO. LTD.
To: MERCK SHARP & DOHME CORP.
Reel/Frame 044304/0780 →
Priority Claims (1)
WO PCT/CN2015/083060 · Jul 1, 2015 · international
Continuity (1)
Related Publication 20180169072A1 · Jun 21, 2018