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- Withdrawn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
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- 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
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| PCT/US2012/058220 WO2013052395A1 (en) | 2011-10-06 | 2012-10-01 | 1,3-substituted azetidine pde10 inhibitors |
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| AU2012313888B2 (en) | 2011-09-27 | 2016-03-31 | Novartis Ag | 3-pyrimidin-4-yl-oxazolidin-2-ones as inhibitors of mutant IDH |
| 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 |
| WO2014078217A1 (en) * | 2012-11-15 | 2014-05-22 | Merck Sharp & Dohme Corp. | Cyclopropyl imidazopyridine pde10 inhibitors |
| EP2919781B1 (en) | 2012-11-15 | 2017-06-28 | Merck Sharp & Dohme Corp. | Cyclobutyl benzimidazoles as pde10 inhibitors |
| 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 |
| US9663513B2 (en) | 2012-11-20 | 2017-05-30 | Merck Sharp & Dohme Corp. | Pyrimidine PDE10 inhibitors |
| EP2922543B1 (en) | 2012-11-20 | 2017-05-24 | Merck Sharp & Dohme Corp. | Substituted pyridone derivatives as 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) |
| KR20150131224A (ko) | 2013-03-14 | 2015-11-24 | 노파르티스 아게 | 돌연변이 idh의 억제제로서의 3-피리미딘-4-일-옥사졸리딘-2-온 |
| 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 |
| WO2019046316A1 (en) * | 2017-08-28 | 2019-03-07 | Acurastem Inc. | PIKFYVE KINASE INHIBITORS |
| PT3860998T (pt) | 2018-10-05 | 2024-04-02 | Annapurna Bio Inc | Compostos e composições para o tratamento de condições associadas à atividade do recetor apj |
| WO2021163727A1 (en) * | 2020-02-11 | 2021-08-19 | 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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| JP4495257B2 (ja) * | 1997-02-19 | 2010-06-30 | バーレツクス ラボラトリーズ インコーポレーテツド | Ｎｏｓ抑制剤としてのｎ−複素環誘導体 |
| EP1499598A1 (en) | 2002-04-18 | 2005-01-26 | Ucb, S.A. | Chemical compounds with dual activity, processes for their preparation and pharmaceutical compositions |
| CN102558155A (zh) * | 2003-01-14 | 2012-07-11 | 阿伦纳药品公司 | 作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗 |
| DE102008020113A1 (de) | 2008-04-23 | 2009-10-29 | Bayer Schering Pharma Aktiengesellschaft | Substituierte Dihydropyrazolone und ihre Verwendung |
| WO2006100461A1 (en) | 2005-03-23 | 2006-09-28 | Astrazeneca Ab | 2-AZETIDINYL-4-(lH-PYRAZOL-3-YLAMINO)PYRIMIDINES AS INHIBITORS OF INSULIN-LIKE GROWTH FACTOR-I RECEPTOR ACTIVITY |
| JP2008540443A (ja) | 2005-05-04 | 2008-11-20 | バーテックス ファーマシューティカルズ インコーポレイテッド | イオンチャネルのモジュレーターとして有用なピリミジンおよびピラジン |
| 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 |
| PT2698062E (pt) * | 2006-12-28 | 2015-10-19 | Abbvie Inc | Inibidores da poli (adp-ribose) polimerase |
| CA2709203A1 (en) * | 2007-12-13 | 2009-06-18 | Siena Biotech S.P.A. | Hedgehog pathway antagonists and therapeutic applications thereof |
| JP2011515462A (ja) | 2008-03-27 | 2011-05-19 | アウククランド ウニセルビセス リミテッド | 置換されたピリミジン、及びトリアジン、並びに癌療法におけるこれらの使用 |
| MX2012013128A (es) * | 2010-05-13 | 2013-03-20 | Amgen Inc | Compuestos heterociclicos de nitrogeno como inhibidores de la fosfodiesterasa 10. |
| WO2012044561A2 (en) | 2010-09-30 | 2012-04-05 | Merck Sharp & Dohme Corp. | 2-alkoxy pyrimidine pde10 inhibitors |
| WO2013028590A1 (en) | 2011-08-25 | 2013-02-28 | Merck Sharp & Dohme Corp. | Pyrimidine pde10 inhibitors |
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- 2012-10-01 EP EP12838133.2A patent/EP2763672B1/en active Active
- 2012-10-01 WO PCT/US2012/058220 patent/WO2013052395A1/en not_active Ceased
- 2012-10-01 AU AU2012318874A patent/AU2012318874A1/en not_active Abandoned
- 2012-10-01 CA CA2851082A patent/CA2851082A1/en not_active Abandoned
- 2012-10-01 US US14/349,041 patent/US9365562B2/en active Active
- 2012-10-05 TW TW101137034A patent/TW201321369A/zh unknown
- 2012-10-05 AR ARP120103729A patent/AR088258A1/es unknown
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