JP2014528446A5 - - Google Patents
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- JP2014528446A5 JP2014528446A5 JP2014534619A JP2014534619A JP2014528446A5 JP 2014528446 A5 JP2014528446 A5 JP 2014528446A5 JP 2014534619 A JP2014534619 A JP 2014534619A JP 2014534619 A JP2014534619 A JP 2014534619A JP 2014528446 A5 JP2014528446 A5 JP 2014528446A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- benzo
- azetidin
- imidazole
- triazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
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- 125000000217 alkyl group Chemical group 0.000 claims 32
- 125000000623 heterocyclic group Chemical group 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 19
- -1 pyrimidinone-yl Chemical group 0.000 claims 18
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 239000003814 drug Substances 0.000 claims 5
- 238000004519 manufacturing process Methods 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 208000020016 psychiatric disease Diseases 0.000 claims 3
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- 208000012902 Nervous system disease Diseases 0.000 claims 2
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 2
- 230000019771 cognition Effects 0.000 claims 2
- 230000004064 dysfunction Effects 0.000 claims 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 230000000926 neurological effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- GRQHRYIFFRNJCF-CYBMUJFWSA-N (2r)-1-[5-methyl-2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]-1,2,4-triazol-3-yl]propan-2-ol Chemical compound C[C@@H](O)CC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 GRQHRYIFFRNJCF-CYBMUJFWSA-N 0.000 claims 1
- GRQHRYIFFRNJCF-ZDUSSCGKSA-N (2s)-1-[5-methyl-2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]-1,2,4-triazol-3-yl]propan-2-ol Chemical compound C[C@H](O)CC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 GRQHRYIFFRNJCF-ZDUSSCGKSA-N 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- RMGUAQRNMIHCIK-UHFFFAOYSA-N 1-[2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]pyridin-4-yl]ethanone Chemical compound CC(=O)C1=CC=NC(C=2N=C(C)N=C(C=2)N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=C1 RMGUAQRNMIHCIK-UHFFFAOYSA-N 0.000 claims 1
- NUFFPUPTXDTLSE-UHFFFAOYSA-N 1-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]pyrazole-4-carbonitrile Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1C=C(C#N)C=N1 NUFFPUPTXDTLSE-UHFFFAOYSA-N 0.000 claims 1
- AJYFGYSUBYSNBJ-UHFFFAOYSA-N 1-[6-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]pyridin-3-yl]ethanone Chemical compound N1=CC(C(=O)C)=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 AJYFGYSUBYSNBJ-UHFFFAOYSA-N 0.000 claims 1
- UVSZVCBDDAXJGW-UHFFFAOYSA-N 1-[[5-methyl-2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]-1,2,4-triazol-3-yl]methyl]pyrrolidin-2-one Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1CN1CCCC1=O UVSZVCBDDAXJGW-UHFFFAOYSA-N 0.000 claims 1
- FPOXZVKIZGKRJY-UHFFFAOYSA-N 1-methyl-2-[1-(2-methyl-6-phenylpyrimidin-4-yl)azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC=C1 FPOXZVKIZGKRJY-UHFFFAOYSA-N 0.000 claims 1
- IADQSRNVKLRKOR-UHFFFAOYSA-N 1-methyl-2-[1-(2-methyl-6-pyrazol-1-ylpyrimidin-4-yl)azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1C=CC=N1 IADQSRNVKLRKOR-UHFFFAOYSA-N 0.000 claims 1
- KUEOYAJBAPAROU-UHFFFAOYSA-N 1-methyl-2-[1-(2-methyl-6-pyridazin-3-ylpyrimidin-4-yl)azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CN=N1 KUEOYAJBAPAROU-UHFFFAOYSA-N 0.000 claims 1
- FDEVSPDWRONDMX-UHFFFAOYSA-N 1-methyl-2-[1-(2-methyl-6-pyridin-2-ylpyrimidin-4-yl)azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC=N1 FDEVSPDWRONDMX-UHFFFAOYSA-N 0.000 claims 1
- AJPFDJKGACBMEW-UHFFFAOYSA-N 1-methyl-2-[1-(2-methyl-6-pyridin-3-ylpyrimidin-4-yl)azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CN=C1 AJPFDJKGACBMEW-UHFFFAOYSA-N 0.000 claims 1
- ZKZABYFCGUFHQI-UHFFFAOYSA-N 1-methyl-2-[1-(2-methyl-6-pyridin-4-ylpyrimidin-4-yl)azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=NC=C1 ZKZABYFCGUFHQI-UHFFFAOYSA-N 0.000 claims 1
- IDWKCHLLTPQNRN-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(2-methylpyridin-3-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CN=C1C IDWKCHLLTPQNRN-UHFFFAOYSA-N 0.000 claims 1
- BZORGVJCHQSWLN-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(3-methyl-5-phenyl-1,2,4-triazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=CC=CC=C1 BZORGVJCHQSWLN-UHFFFAOYSA-N 0.000 claims 1
- JQAABLDSEYRCFR-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(3-methyl-5-propan-2-yl-1,2,4-triazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound CC(C)C1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 JQAABLDSEYRCFR-UHFFFAOYSA-N 0.000 claims 1
- TVKSLFXRCSIKOI-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(3-methyl-5-propyl-1,2,4-triazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound CCCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 TVKSLFXRCSIKOI-UHFFFAOYSA-N 0.000 claims 1
- NUTNASHZLIJXDT-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(3-methyl-5-pyridin-3-yl-1,2,4-triazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=CC=CN=C1 NUTNASHZLIJXDT-UHFFFAOYSA-N 0.000 claims 1
- RWJGWWFZFVGTKN-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(3-propan-2-ylpyrazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=C(C(C)C)C=CN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 RWJGWWFZFVGTKN-UHFFFAOYSA-N 0.000 claims 1
- SFXYJQNTPIQCFO-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(4-methylpyrazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C1=C(C)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 SFXYJQNTPIQCFO-UHFFFAOYSA-N 0.000 claims 1
- KDOKQHLWOBCKKW-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(4-methyltriazol-2-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=C(C)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 KDOKQHLWOBCKKW-UHFFFAOYSA-N 0.000 claims 1
- SFKRVRLQTAMDGK-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(5-methylpyridin-2-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=CC(C)=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 SFKRVRLQTAMDGK-UHFFFAOYSA-N 0.000 claims 1
- UMKKADOZDBPPIQ-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(5-methyltriazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound CC1=CN=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 UMKKADOZDBPPIQ-UHFFFAOYSA-N 0.000 claims 1
- OOVVZTHIMXFFIR-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-(6-methylpyridin-2-yl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound CC1=CC=CC(C=2N=C(C)N=C(C=2)N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=N1 OOVVZTHIMXFFIR-UHFFFAOYSA-N 0.000 claims 1
- JOXPFBFNJLVXON-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[3-methyl-5-(5-methylpyrazin-2-yl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=CN=C(C)C=N1 JOXPFBFNJLVXON-UHFFFAOYSA-N 0.000 claims 1
- MBNPHOMXHXZVNK-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[3-methyl-5-(6-methylpyridin-3-yl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=CC=C(C)N=C1 MBNPHOMXHXZVNK-UHFFFAOYSA-N 0.000 claims 1
- VNQRSMLYBMAQTD-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[3-methyl-5-(oxan-4-yl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1CCOCC1 VNQRSMLYBMAQTD-UHFFFAOYSA-N 0.000 claims 1
- ZKZXGJWXUHPGDA-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[3-methyl-5-(phenoxymethyl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1COC1=CC=CC=C1 ZKZXGJWXUHPGDA-UHFFFAOYSA-N 0.000 claims 1
- UNHNEQXZHGKGSX-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[3-methyl-5-(trifluoromethyl)pyrazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=C(C)C=C(C(F)(F)F)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 UNHNEQXZHGKGSX-UHFFFAOYSA-N 0.000 claims 1
- OBAXUAJKPKQQSB-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[5-methyl-3-(trifluoromethyl)-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound CC1=NC(C(F)(F)F)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 OBAXUAJKPKQQSB-UHFFFAOYSA-N 0.000 claims 1
- AGWOHPRXXKREGR-UHFFFAOYSA-N 1-methyl-2-[1-[2-methyl-6-[6-(trifluoromethyl)pyridin-2-yl]pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC(C(F)(F)F)=N1 AGWOHPRXXKREGR-UHFFFAOYSA-N 0.000 claims 1
- WILDGFBADLMDSK-UHFFFAOYSA-N 1-methyl-2-[1-[6-(4-methyltriazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=NC(C)=CN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=N1 WILDGFBADLMDSK-UHFFFAOYSA-N 0.000 claims 1
- NHXQCQOMEZDOFV-UHFFFAOYSA-N 1-methyl-2-[1-[6-(4-methyltriazol-2-yl)-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=C(C)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=N1 NHXQCQOMEZDOFV-UHFFFAOYSA-N 0.000 claims 1
- WBBMFHIALBRYNM-UHFFFAOYSA-N 1-methyl-2-[1-[6-(5-methylpyridin-2-yl)-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound N1=CC(C)=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=N1 WBBMFHIALBRYNM-UHFFFAOYSA-N 0.000 claims 1
- OQJVLFORMZFLFY-UHFFFAOYSA-N 1-methyl-2-[1-[6-[3-methyl-5-(oxan-4-yl)-1,2,4-triazol-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]benzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=NC=1N1N=C(C)N=C1C1CCOCC1 OQJVLFORMZFLFY-UHFFFAOYSA-N 0.000 claims 1
- MRPZUZQCBHAAAY-UHFFFAOYSA-N 1-methyl-4-[5-methyl-2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]-1,2,4-triazol-3-yl]pyrrolidin-2-one Chemical compound C1C(=O)N(C)CC1C1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 MRPZUZQCBHAAAY-UHFFFAOYSA-N 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
- ARZOFWVNVGJVDJ-UHFFFAOYSA-N 2-[1-[2-cyclopropyl-6-(3,5-dimethyl-1,2,4-triazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C2CC2)=N1 ARZOFWVNVGJVDJ-UHFFFAOYSA-N 0.000 claims 1
- DIVNTGKXJPVIIX-UHFFFAOYSA-N 2-[1-[2-cyclopropyl-6-(4-methylpyrazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C1=C(C)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C2CC2)=N1 DIVNTGKXJPVIIX-UHFFFAOYSA-N 0.000 claims 1
- QHHUEFOVSJJGOE-UHFFFAOYSA-N 2-[1-[2-cyclopropyl-6-(4-methyltriazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=NC(C)=CN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C2CC2)=N1 QHHUEFOVSJJGOE-UHFFFAOYSA-N 0.000 claims 1
- SETRSHIBWOZCAE-UHFFFAOYSA-N 2-[1-[2-cyclopropyl-6-(4-methyltriazol-2-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C2CC2)=N1 SETRSHIBWOZCAE-UHFFFAOYSA-N 0.000 claims 1
- ABYJZXNZLUMTFP-UHFFFAOYSA-N 2-[1-[2-cyclopropyl-6-[5-(methoxymethyl)-3-methyl-1,2,4-triazol-1-yl]pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C2CC2)=N1 ABYJZXNZLUMTFP-UHFFFAOYSA-N 0.000 claims 1
- PDLTYNGCJLJHOB-UHFFFAOYSA-N 2-[1-[2-methoxy-6-(4-methylpyrazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(OC)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1C=C(C)C=N1 PDLTYNGCJLJHOB-UHFFFAOYSA-N 0.000 claims 1
- SUJBGYYFYLKDMC-UHFFFAOYSA-N 2-[1-[2-methoxy-6-(4-methyltriazol-2-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(OC)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1N=CC(C)=N1 SUJBGYYFYLKDMC-UHFFFAOYSA-N 0.000 claims 1
- PHLPYHSRYTXKKL-UHFFFAOYSA-N 2-[1-[2-methoxy-6-(5-methylpyridin-2-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(OC)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=C(C)C=N1 PHLPYHSRYTXKKL-UHFFFAOYSA-N 0.000 claims 1
- RUWRDHSXYISSAK-UHFFFAOYSA-N 2-[1-[6-(2-fluoro-6-methylpyridin-3-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound FC1=NC(C)=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 RUWRDHSXYISSAK-UHFFFAOYSA-N 0.000 claims 1
- IWPZXPSJTFYGSE-UHFFFAOYSA-N 2-[1-[6-(2-fluorophenyl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC=C1F IWPZXPSJTFYGSE-UHFFFAOYSA-N 0.000 claims 1
- WVFUVSVTBHWSKN-UHFFFAOYSA-N 2-[1-[6-(2-methoxy-6-methylpyridin-3-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COC1=NC(C)=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 WVFUVSVTBHWSKN-UHFFFAOYSA-N 0.000 claims 1
- MIQSTHUCYUNULC-UHFFFAOYSA-N 2-[1-[6-(2-methoxyphenyl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COC1=CC=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 MIQSTHUCYUNULC-UHFFFAOYSA-N 0.000 claims 1
- SYCVTASSMBJNSD-UHFFFAOYSA-N 2-[1-[6-(2-methoxypyridin-3-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COC1=NC=CC=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 SYCVTASSMBJNSD-UHFFFAOYSA-N 0.000 claims 1
- AGISGMLDAXPKQB-UHFFFAOYSA-N 2-[1-[6-(3,4-dimethylpyrazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)C(C)=CN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 AGISGMLDAXPKQB-UHFFFAOYSA-N 0.000 claims 1
- ZFCQPMZWTXNQBG-UHFFFAOYSA-N 2-[1-[6-(3,5-diethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(CC)N=C(CC)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 ZFCQPMZWTXNQBG-UHFFFAOYSA-N 0.000 claims 1
- ZJQACEHBAXTQEC-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-(2-methylimidazol-1-yl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(N2C(=NC=C2)C)=N1 ZJQACEHBAXTQEC-UHFFFAOYSA-N 0.000 claims 1
- DRSHSXSLVMNWRW-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=N1 DRSHSXSLVMNWRW-UHFFFAOYSA-N 0.000 claims 1
- DJDHLSMOQPPTSV-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-[(2-methylpyrazol-3-yl)methoxy]pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(OCC=2N(N=CC=2)C)=N1 DJDHLSMOQPPTSV-UHFFFAOYSA-N 0.000 claims 1
- SGATVSJIEYCDOZ-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methoxypyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(OC)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1N=C(C)N=C1C SGATVSJIEYCDOZ-UHFFFAOYSA-N 0.000 claims 1
- QGQJBVKKPPTMLU-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1,4-dimethylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC(C)=C3N=2)C)=NC(C)=N1 QGQJBVKKPPTMLU-UHFFFAOYSA-N 0.000 claims 1
- YCUKEQMJIZDJQK-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-(2-ethoxyethyl)benzimidazole Chemical compound N=1C2=CC=CC=C2N(CCOCC)C=1C(C1)CN1C(N=C(C)N=1)=CC=1N1N=C(C)N=C1C YCUKEQMJIZDJQK-UHFFFAOYSA-N 0.000 claims 1
- AQXWGWMGWNWVFB-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-(2-fluoroethyl)benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)CCF)=NC(C)=N1 AQXWGWMGWNWVFB-UHFFFAOYSA-N 0.000 claims 1
- IFFIRHPUTCUZLY-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-ethylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(CC)C=1C(C1)CN1C(N=C(C)N=1)=CC=1N1N=C(C)N=C1C IFFIRHPUTCUZLY-UHFFFAOYSA-N 0.000 claims 1
- LRGBBJWLJGKDPB-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methyl-4-(trifluoromethyl)benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC(=C3N=2)C(F)(F)F)C)=NC(C)=N1 LRGBBJWLJGKDPB-UHFFFAOYSA-N 0.000 claims 1
- KSHVNQSJBRMRDI-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 KSHVNQSJBRMRDI-UHFFFAOYSA-N 0.000 claims 1
- GVQOHJBCSUVZFN-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-propylbenzimidazole Chemical compound N=1C2=CC=CC=C2N(CCC)C=1C(C1)CN1C(N=C(C)N=1)=CC=1N1N=C(C)N=C1C GVQOHJBCSUVZFN-UHFFFAOYSA-N 0.000 claims 1
- AEPMADCGUZBTIY-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1h-benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2NC3=CC=CC=C3N=2)=NC(C)=N1 AEPMADCGUZBTIY-UHFFFAOYSA-N 0.000 claims 1
- HYSGUXIEJMDSOE-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-4-(trifluoromethyl)-1h-benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2NC3=C(C=CC=C3N=2)C(F)(F)F)=NC(C)=N1 HYSGUXIEJMDSOE-UHFFFAOYSA-N 0.000 claims 1
- XICXHHHEQUMRIG-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-4-fluoro-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC(F)=C3N=2)C)=NC(C)=N1 XICXHHHEQUMRIG-UHFFFAOYSA-N 0.000 claims 1
- IUVNLRUSBDVKKG-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-4-fluoro-1h-benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2NC3=C(F)C=CC=C3N=2)=NC(C)=N1 IUVNLRUSBDVKKG-UHFFFAOYSA-N 0.000 claims 1
- PFWMZEJCZWZAII-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-4-methyl-1h-benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2NC3=C(C)C=CC=C3N=2)=NC(C)=N1 PFWMZEJCZWZAII-UHFFFAOYSA-N 0.000 claims 1
- YSPOJELCWXRLEB-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-6-(trifluoromethyl)-1h-benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2NC3=CC(=CC=C3N=2)C(F)(F)F)=NC(C)=N1 YSPOJELCWXRLEB-UHFFFAOYSA-N 0.000 claims 1
- YOMMHDSJZADDAJ-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-6-methyl-1h-benzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2NC3=CC(C)=CC=C3N=2)=NC(C)=N1 YOMMHDSJZADDAJ-UHFFFAOYSA-N 0.000 claims 1
- OSJZXDKBZKYGKO-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-7-fluoro-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=C(F)C=CC=C3N=2)C)=NC(C)=N1 OSJZXDKBZKYGKO-UHFFFAOYSA-N 0.000 claims 1
- ZGSNAIJVRWPEAX-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylsulfanylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(SC)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1N=C(C)N=C1C ZGSNAIJVRWPEAX-UHFFFAOYSA-N 0.000 claims 1
- YNUPOXUYOLBVIL-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-propan-2-yloxypyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(OC(C)C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1N=C(C)N=C1C YNUPOXUYOLBVIL-UHFFFAOYSA-N 0.000 claims 1
- YEAKOKCXGLUHSM-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-pyrazol-1-ylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(N2N=CC=C2)=N1 YEAKOKCXGLUHSM-UHFFFAOYSA-N 0.000 claims 1
- SGNPVBGWJKYZTI-UHFFFAOYSA-N 2-[1-[6-(3,5-dimethylpyrazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(C)C=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 SGNPVBGWJKYZTI-UHFFFAOYSA-N 0.000 claims 1
- LHJJYOBPERUMEO-UHFFFAOYSA-N 2-[1-[6-(3-cyclopropylpyrazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N(N=1)C=CC=1C1CC1 LHJJYOBPERUMEO-UHFFFAOYSA-N 0.000 claims 1
- JEUPXKGTRVHMKD-UHFFFAOYSA-N 2-[1-[6-(3-methoxypyrazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N1=C(OC)C=CN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 JEUPXKGTRVHMKD-UHFFFAOYSA-N 0.000 claims 1
- QWLWWNLXWBCAPA-UHFFFAOYSA-N 2-[1-[6-(3-methoxypyridin-2-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COC1=CC=CN=C1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 QWLWWNLXWBCAPA-UHFFFAOYSA-N 0.000 claims 1
- PLRHWOWBKXRNJH-UHFFFAOYSA-N 2-[1-[6-(4-ethylpyrazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C1=C(CC)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 PLRHWOWBKXRNJH-UHFFFAOYSA-N 0.000 claims 1
- AAPZDXYYOLSIDO-UHFFFAOYSA-N 2-[1-[6-(4-methoxypyrazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C1=C(OC)C=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 AAPZDXYYOLSIDO-UHFFFAOYSA-N 0.000 claims 1
- VJRHPRNZDBNXNZ-UHFFFAOYSA-N 2-[1-[6-(5-chloropyridin-2-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=C(Cl)C=N1 VJRHPRNZDBNXNZ-UHFFFAOYSA-N 0.000 claims 1
- NSOJZFXPDYJGLR-UHFFFAOYSA-N 2-[1-[6-(5-cyclohexyl-3-methyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1CCCCC1 NSOJZFXPDYJGLR-UHFFFAOYSA-N 0.000 claims 1
- FXBMJPQJSWVJSV-UHFFFAOYSA-N 2-[1-[6-(5-cyclopropyl-3-methyl-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=NC=1N1N=C(C)N=C1C1CC1 FXBMJPQJSWVJSV-UHFFFAOYSA-N 0.000 claims 1
- MUMLPFVTCVZAEX-UHFFFAOYSA-N 2-[1-[6-(5-cyclopropyl-3-methyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1CC1 MUMLPFVTCVZAEX-UHFFFAOYSA-N 0.000 claims 1
- ZDUZDTUVQBCOOL-UHFFFAOYSA-N 2-[1-[6-(5-ethyl-3-methyl-1,2,4-triazol-1-yl)-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound CCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=N1 ZDUZDTUVQBCOOL-UHFFFAOYSA-N 0.000 claims 1
- ANUOCEVAFFTNAY-UHFFFAOYSA-N 2-[1-[6-(5-ethyl-3-methyl-1,2,4-triazol-1-yl)-2-methoxypyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound CCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(OC)=N1 ANUOCEVAFFTNAY-UHFFFAOYSA-N 0.000 claims 1
- RLJALUXXCIPPJR-UHFFFAOYSA-N 2-[1-[6-(5-ethyl-3-methyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound CCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 RLJALUXXCIPPJR-UHFFFAOYSA-N 0.000 claims 1
- QQPBPJZOMFCMJP-UHFFFAOYSA-N 2-[1-[6-[2-(difluoromethoxy)phenyl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC=C1OC(F)F QQPBPJZOMFCMJP-UHFFFAOYSA-N 0.000 claims 1
- QOKYUCIKRDCXNZ-UHFFFAOYSA-N 2-[1-[6-[5-(2,6-difluorophenyl)-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=C(F)C=CC=C1F QOKYUCIKRDCXNZ-UHFFFAOYSA-N 0.000 claims 1
- PHBGAHMRTUHBJH-UHFFFAOYSA-N 2-[1-[6-[5-(2-chlorophenyl)-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=CC=CC=C1Cl PHBGAHMRTUHBJH-UHFFFAOYSA-N 0.000 claims 1
- WSCCUZFQVFVRJW-UHFFFAOYSA-N 2-[1-[6-[5-(2-fluorophenyl)-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1C1=CC=CC=C1F WSCCUZFQVFVRJW-UHFFFAOYSA-N 0.000 claims 1
- SZPRZHHZVAPNTF-UHFFFAOYSA-N 2-[1-[6-[5-(2-methoxyethyl)-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COCCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 SZPRZHHZVAPNTF-UHFFFAOYSA-N 0.000 claims 1
- ARZUAUVSUQBJBO-UHFFFAOYSA-N 2-[1-[6-[5-(methoxymethyl)-3-methyl-1,2,4-triazol-1-yl]-2-(trifluoromethyl)pyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C(F)(F)F)=N1 ARZUAUVSUQBJBO-UHFFFAOYSA-N 0.000 claims 1
- QSBBADSHNYTSGO-UHFFFAOYSA-N 2-[1-[6-[5-(methoxymethyl)-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound COCC1=NC(C)=NN1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=N1 QSBBADSHNYTSGO-UHFFFAOYSA-N 0.000 claims 1
- BTLSKORSWWANTC-UHFFFAOYSA-N 2-[1-[6-[5-[(2,5-difluorophenyl)methyl]-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1CC1=CC(F)=CC=C1F BTLSKORSWWANTC-UHFFFAOYSA-N 0.000 claims 1
- HBMJHPVHFJRLTG-UHFFFAOYSA-N 2-[1-[6-[5-[(4-fluorophenyl)methyl]-3-methyl-1,2,4-triazol-1-yl]-2-methylpyrimidin-4-yl]azetidin-3-yl]-1-methylbenzimidazole Chemical compound C=1C(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C)=NC=1N1N=C(C)N=C1CC1=CC=C(F)C=C1 HBMJHPVHFJRLTG-UHFFFAOYSA-N 0.000 claims 1
- HNXWDDKSPXMVPQ-UHFFFAOYSA-N 2-[2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]benzimidazol-1-yl]acetonitrile Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)CC#N)=NC(C)=N1 HNXWDDKSPXMVPQ-UHFFFAOYSA-N 0.000 claims 1
- UTEHRXCFEXDRMZ-UHFFFAOYSA-N 2-[2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]benzimidazol-1-yl]ethanol Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)CCO)=NC(C)=N1 UTEHRXCFEXDRMZ-UHFFFAOYSA-N 0.000 claims 1
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- ZVEWWKXWUCEKRJ-UHFFFAOYSA-N 2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]-1,3-thiazole Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=NC=CS1 ZVEWWKXWUCEKRJ-UHFFFAOYSA-N 0.000 claims 1
- GVMLDPFAZSPUMG-UHFFFAOYSA-N 2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]benzoic acid Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC=C1C(O)=O GVMLDPFAZSPUMG-UHFFFAOYSA-N 0.000 claims 1
- RUYMWZGTVJYYNK-UHFFFAOYSA-N 2-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]phenol Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=CC=C1O RUYMWZGTVJYYNK-UHFFFAOYSA-N 0.000 claims 1
- RRAZXEKNBSXFSU-UHFFFAOYSA-N 2-[4-(3,5-dimethyl-1,2,4-triazol-1-yl)-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-2-yl]acetonitrile Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(CC#N)=N1 RRAZXEKNBSXFSU-UHFFFAOYSA-N 0.000 claims 1
- MXDSMAKZLMOQFO-UHFFFAOYSA-N 2-[[4-(3,5-dimethyl-1,2,4-triazol-1-yl)-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-2-yl]oxymethyl]-1,3-thiazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(OCC=2SC=CN=2)=N1 MXDSMAKZLMOQFO-UHFFFAOYSA-N 0.000 claims 1
- GIMXPJMZRJTNJI-UHFFFAOYSA-N 3-[2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]benzimidazol-1-yl]propanenitrile Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)CCC#N)=NC(C)=N1 GIMXPJMZRJTNJI-UHFFFAOYSA-N 0.000 claims 1
- BEUNQUHXGZMYJQ-UHFFFAOYSA-N 3-[[4-(3,5-dimethyl-1,2,4-triazol-1-yl)-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-2-yl]oxymethyl]-1,2-oxazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(OCC2=NOC=C2)=N1 BEUNQUHXGZMYJQ-UHFFFAOYSA-N 0.000 claims 1
- SEUCCTPZMKLCGK-UHFFFAOYSA-N 4-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methyl-6-[3-(5-methylpyridin-2-yl)azetidin-1-yl]pyrimidine Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N=CC(C)=CC=2)=NC(C)=N1 SEUCCTPZMKLCGK-UHFFFAOYSA-N 0.000 claims 1
- JHWJUQRHBKVMCQ-UHFFFAOYSA-N 4-(3,5-dimethyl-1,2,4-triazol-1-yl)-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidine-2-carbonitrile Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(C#N)=N1 JHWJUQRHBKVMCQ-UHFFFAOYSA-N 0.000 claims 1
- SSLDCLNEUNGLQX-UHFFFAOYSA-N 4-[2-[1-[6-(3,5-dimethyl-1,2,4-triazol-1-yl)-2-methylpyrimidin-4-yl]azetidin-3-yl]benzimidazol-1-yl]butanenitrile Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)CCCC#N)=NC(C)=N1 SSLDCLNEUNGLQX-UHFFFAOYSA-N 0.000 claims 1
- OLEAHVIUBWTTHY-UHFFFAOYSA-N 5-[[4-(3,5-dimethyl-1,2,4-triazol-1-yl)-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-2-yl]oxymethyl]-1,2-oxazole Chemical compound N1=C(C)N=C(C)N1C1=CC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=NC(OCC=2ON=CC=2)=N1 OLEAHVIUBWTTHY-UHFFFAOYSA-N 0.000 claims 1
- JWAVODAVGPUXMA-UHFFFAOYSA-N 5-[[4-(3,5-dimethyl-1,2,4-triazol-1-yl)-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-2-yl]oxymethyl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(COC=2N=C(C=C(N=2)N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)N2C(=NC(C)=N2)C)=N1 JWAVODAVGPUXMA-UHFFFAOYSA-N 0.000 claims 1
- FCKGSFOWBFWMTB-UHFFFAOYSA-N 6-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]pyridine-3-carbonitrile Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1C1=CC=C(C#N)C=N1 FCKGSFOWBFWMTB-UHFFFAOYSA-N 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000024254 Delusional disease Diseases 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
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- 208000016285 Movement disease Diseases 0.000 claims 1
- 208000011963 Substance-induced psychotic disease Diseases 0.000 claims 1
- 231100000393 Substance-induced psychotic disorder Toxicity 0.000 claims 1
- XSBPICOXPCLVAY-UHFFFAOYSA-N [1-[2-methyl-6-[3-(1-methylbenzimidazol-2-yl)azetidin-1-yl]pyrimidin-4-yl]pyrazol-4-yl]methanol Chemical compound N=1C(C)=NC(N2CC(C2)C=2N(C3=CC=CC=C3N=2)C)=CC=1N1C=C(CO)C=N1 XSBPICOXPCLVAY-UHFFFAOYSA-N 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 125000004566 azetidin-1-yl group Chemical group N1(CCC1)* 0.000 claims 1
- 210000004227 basal ganglia Anatomy 0.000 claims 1
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- 239000003795 chemical substances by application Substances 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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- 229940017219 methyl propionate Drugs 0.000 claims 1
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| US201161544065P | 2011-10-06 | 2011-10-06 | |
| US61/544,065 | 2011-10-06 | ||
| PCT/US2012/058220 WO2013052395A1 (en) | 2011-10-06 | 2012-10-01 | 1,3-substituted azetidine pde10 inhibitors |
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| JP2014528446A JP2014528446A (ja) | 2014-10-27 |
| JP2014528446A5 true JP2014528446A5 (OSRAM) | 2015-11-19 |
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| JP6026544B2 (ja) | 2011-09-27 | 2016-11-16 | ノバルティス アーゲー | 変異体ｉｄｈの阻害剤としての３−ピリミジン−４−イル−オキサゾリジン−２−オン類 |
| UY34632A (es) | 2012-02-24 | 2013-05-31 | Novartis Ag | Compuestos de oxazolidin- 2- ona y usos de los mismos |
| US9296733B2 (en) | 2012-11-12 | 2016-03-29 | Novartis Ag | Oxazolidin-2-one-pyrimidine derivative and use thereof for the treatment of conditions, diseases and disorders dependent upon PI3 kinases |
| TW201422610A (zh) * | 2012-11-15 | 2014-06-16 | Merck Sharp & Dohme | 作爲ｐｄｅ１０抑制劑之經二級醇取代之三唑 |
| US9284302B2 (en) | 2012-11-15 | 2016-03-15 | Merck Sharp & Dohme Corp. | Cyclobutyl benzimidazoles as PDE 10 inhibitors |
| US9359348B2 (en) | 2012-11-15 | 2016-06-07 | Merck Sharp & Dohme Corp. | Cyclopropyl imidazopyridine PDE10 inhibitors |
| EP2922543B1 (en) | 2012-11-20 | 2017-05-24 | Merck Sharp & Dohme Corp. | Substituted pyridone derivatives as pde10 inhibitors |
| WO2014081619A1 (en) | 2012-11-20 | 2014-05-30 | Merck Sharp & Dohme Corp. | Pyrimidine pde10 inhibitors |
| ES2480341B1 (es) * | 2013-01-24 | 2015-01-22 | Palobiofarma S.L | Nuevos derivados de pirimidina como inhibidores de la fosfodiesterasa 10 (PDE-10) |
| HK1213251A1 (zh) | 2013-03-14 | 2016-06-30 | Novartis Ag | 作为突变idh抑制剂的3-嘧啶-4-基-恶唑烷-2-酮化合物 |
| FR3040057A1 (fr) * | 2015-08-13 | 2017-02-17 | Inventiva | Composes de type azetidine carboxylique |
| US10583269B2 (en) | 2016-06-01 | 2020-03-10 | Becton, Dickinson And Company | Magnetized catheters, devices, uses and methods of using magnetized catheters |
| EP3676264A1 (en) * | 2017-08-28 | 2020-07-08 | Acurastem Inc. | Pikfyve kinase inhibitors |
| CN120365272A (zh) | 2018-10-05 | 2025-07-25 | 安娜普尔纳生物股份有限公司 | 用于治疗与apj受体活性有关的疾病的化合物和组合物 |
| US20230135152A1 (en) * | 2020-02-11 | 2023-05-04 | AcuraStem Incorporated | Pikfyve kinase inhibitors |
| WO2025049402A1 (en) * | 2023-08-28 | 2025-03-06 | Quanta Therapeutics, Inc. | Kras modulators and uses thereof |
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| DK0968206T3 (da) * | 1997-02-19 | 2007-03-26 | Berlex Inc | N-heterocykliske derivater som NOS-inhibitorer |
| EP1499598A1 (en) * | 2002-04-18 | 2005-01-26 | Ucb, S.A. | Chemical compounds with dual activity, processes for their preparation and pharmaceutical compositions |
| HRP20050696B1 (en) * | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| DE102008020113A1 (de) | 2008-04-23 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dihydropyrazolone und ihre Verwendung |
| JP2008534481A (ja) * | 2005-03-23 | 2008-08-28 | アストラゼネカ アクチボラグ | インスリン様増殖因子−１受容体活性の阻害剤としての２−アゼチジニル−４−（１ｈ−ピラゾール−３−イルアミノ）ピリミジン |
| EP1877385A1 (en) * | 2005-05-04 | 2008-01-16 | Vertex Pharmaceuticals Incorporated | Pyrimidines and pyrazines useful as modulators of ion channels |
| CA2654792A1 (en) * | 2006-06-12 | 2007-12-21 | Merck Frosst Canada Ltd. | Azetidine derivatives as inhibitors of stearoyl-coenzyme a delta-9 desaturase |
| DE102006050513A1 (de) * | 2006-10-26 | 2008-04-30 | Bayer Healthcare Ag | Substitiuierte Dihydropyrazolone und ihre Verwendung |
| UA97506C2 (xx) * | 2006-12-28 | 2012-02-27 | Эбботт Лаборетриз | Інгібітори полі(adp-рибозо)полімерази$ингибиторы поли(adp-рибозо)полимеразы |
| CN101896472A (zh) | 2007-12-13 | 2010-11-24 | 锡耶纳生物技术股份公司 | Hedgehog途径拮抗剂及其治疗应用 |
| EP2276750A2 (en) * | 2008-03-27 | 2011-01-26 | Auckland Uniservices Limited | Substituted pyrimidines and triazines and their use in cancer therapy |
| MX2012013128A (es) * | 2010-05-13 | 2013-03-20 | Amgen Inc | Compuestos heterociclicos de nitrogeno como inhibidores de la fosfodiesterasa 10. |
| US8785467B2 (en) | 2010-09-30 | 2014-07-22 | Merck Sharp & Dohme Corp. | Alkoxy pyrimidine PDE10 inhibitors |
| MY157301A (en) | 2011-08-25 | 2016-05-31 | Merck Sharp & Dohme | Pyrimidine pde10 inhibitors |
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2012
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- 2012-10-01 CA CA2851082A patent/CA2851082A1/en not_active Abandoned
- 2012-10-01 EP EP12838133.2A patent/EP2763672B1/en active Active
- 2012-10-01 US US14/349,041 patent/US9365562B2/en active Active
- 2012-10-01 AU AU2012318874A patent/AU2012318874A1/en not_active Abandoned
- 2012-10-01 WO PCT/US2012/058220 patent/WO2013052395A1/en not_active Ceased
- 2012-10-05 TW TW101137034A patent/TW201321369A/zh unknown
- 2012-10-05 AR ARP120103729A patent/AR088258A1/es unknown
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