ES2367663T3 - Derivados de fenil-{3-(3-(1h-pirrol-2-il)-[1,2,4]oxadiazol-5-il}piperidin-1-il)-metanona y compuestos relacionados como moduladores alostéricos positivos de los receptores de glutamato metabotrópicos. - Google Patents

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Publication number

ES2367663T3

ES2367663T3 ES06779899T ES06779899T ES2367663T3 ES 2367663 T3 ES2367663 T3 ES 2367663T3 ES 06779899 T ES06779899 T ES 06779899T ES 06779899 T ES06779899 T ES 06779899T ES 2367663 T3 ES2367663 T3 ES 2367663T3

Authority

ES

Spain

Prior art keywords

alkyl

oxadiazol

piperidin

methanone

fluoro

Prior art date

2005-05-18

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.)

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• 150000001875 compounds Chemical class 0.000 title claims abstract description 205
• 102000016193 Metabotropic glutamate receptors Human genes 0.000 title claims description 12
• 108010010914 Metabotropic glutamate receptors Proteins 0.000 title claims description 12
• CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 title 1
• 108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 claims abstract description 50
• 102000012777 Metabotropic Glutamate 5 Receptor Human genes 0.000 claims abstract description 50
• 230000002265 prevention Effects 0.000 claims abstract description 21
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 208000015114 central nervous system disease Diseases 0.000 claims abstract 5
• -1 hydroxy, amino Chemical group 0.000 claims description 164
• 239000000203 mixture Substances 0.000 claims description 105
• 125000001072 heteroaryl group Chemical group 0.000 claims description 75
• 125000003118 aryl group Chemical group 0.000 claims description 74
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 45
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 45
• 125000000217 alkyl group Chemical group 0.000 claims description 45
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 36
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 33
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 29
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 29
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 27
• 150000002367 halogens Chemical class 0.000 claims description 26
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 21
• 230000003281 allosteric effect Effects 0.000 claims description 21
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 18
• 150000003839 salts Chemical class 0.000 claims description 17
• 229910052736 halogen Inorganic materials 0.000 claims description 16
• 239000012453 solvate Substances 0.000 claims description 13
• 210000003169 central nervous system Anatomy 0.000 claims description 12
• 208000035475 disorder Diseases 0.000 claims description 12
• 150000004677 hydrates Chemical class 0.000 claims description 12
• 201000000980 schizophrenia Diseases 0.000 claims description 12
• KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims description 11
• 229940025084 amphetamine Drugs 0.000 claims description 11
• 239000003814 drug Substances 0.000 claims description 10
• 125000001424 substituent group Chemical group 0.000 claims description 10
• 229910052799 carbon Inorganic materials 0.000 claims description 9
• 125000004429 atom Chemical group 0.000 claims description 8
• 239000000126 substance Substances 0.000 claims description 8
• 208000028017 Psychotic disease Diseases 0.000 claims description 7
• 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims description 7
• OJYIYJOUIBEIFY-AWEZNQCLSA-N (6-fluoropyridin-3-yl)-[(3S)-3-[5-(4-propan-2-yl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC(C)C1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 OJYIYJOUIBEIFY-AWEZNQCLSA-N 0.000 claims description 5
• 208000019901 Anxiety disease Diseases 0.000 claims description 5
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• NRPPKKVRPGCELL-AWEZNQCLSA-N (2,4-difluorophenyl)-[(3S)-3-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC3=CC=CC=C3C=2)CCC1 NRPPKKVRPGCELL-AWEZNQCLSA-N 0.000 claims description 4
• LUWWVGZLSXBKFM-UHFFFAOYSA-N (3,4-difluorophenyl)-[3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CC=2)CCC1 LUWWVGZLSXBKFM-UHFFFAOYSA-N 0.000 claims description 4
• FGFLALOXMGHYSF-UHFFFAOYSA-N (4-fluorophenyl)-[3-[5-(1H-indol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC3=CC=CC=C3C=2)CCC1 FGFLALOXMGHYSF-UHFFFAOYSA-N 0.000 claims description 4
• PPRTYCFGRLGSJU-UHFFFAOYSA-N (4-fluorophenyl)-[3-[5-(1h-pyrazol-5-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NN=CC=2)CCC1 PPRTYCFGRLGSJU-UHFFFAOYSA-N 0.000 claims description 4
• 241000124008 Mammalia Species 0.000 claims description 4
• WHGRYTYIQIILBL-JTQLQIEISA-N [(3S)-3-[5-(4-bromo-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(3-fluoropyridin-4-yl)methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Br)C=2)CCC1 WHGRYTYIQIILBL-JTQLQIEISA-N 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 208000011117 substance-related disease Diseases 0.000 claims description 4
• WBYKZAYKLRWFIQ-UHFFFAOYSA-N (2,4-difluorophenyl)-[3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CC=2)CCC1 WBYKZAYKLRWFIQ-UHFFFAOYSA-N 0.000 claims description 3
• KSXKNDXBIXELCD-NSHDSACASA-N (2-fluoropyridin-4-yl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 KSXKNDXBIXELCD-NSHDSACASA-N 0.000 claims description 3
• QLBRRGDJRUMOKT-NSHDSACASA-N (2-fluoropyridin-4-yl)-[(3S)-3-[5-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 QLBRRGDJRUMOKT-NSHDSACASA-N 0.000 claims description 3
• MENUUDHIISNRIW-HNNXBMFYSA-N (3,4-difluorophenyl)-[(3S)-3-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC3=CC=CC=C3C=2)CCC1 MENUUDHIISNRIW-HNNXBMFYSA-N 0.000 claims description 3
• RANDMAUZUPLZBV-LBPRGKRZSA-N (3,4-difluorophenyl)-[(3S)-3-[3-(5-methyl-1H-imidazol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=N1 RANDMAUZUPLZBV-LBPRGKRZSA-N 0.000 claims description 3
• LUWWVGZLSXBKFM-LBPRGKRZSA-N (3,4-difluorophenyl)-[(3S)-3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=CC=2)CCC1 LUWWVGZLSXBKFM-LBPRGKRZSA-N 0.000 claims description 3
• KIPDNXNSBZJSHW-UHFFFAOYSA-N (3,4-difluorophenyl)-[3-[5-(1h-pyrazol-5-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NN=CC=2)CCC1 KIPDNXNSBZJSHW-UHFFFAOYSA-N 0.000 claims description 3
• ZKBIQSQAINHYDH-JTQLQIEISA-N (3-fluoropyridin-4-yl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C(=CN=CC=2)F)=C1 ZKBIQSQAINHYDH-JTQLQIEISA-N 0.000 claims description 3
• GYLZIHOGODNVFM-LBPRGKRZSA-N (3-fluoropyridin-4-yl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C(=CN=CC=2)F)=C1 GYLZIHOGODNVFM-LBPRGKRZSA-N 0.000 claims description 3
• BWUIIXZUPYXCHA-UHFFFAOYSA-N (4-fluoro-2-methylphenyl)-[3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound CC1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CC=2)CCC1 BWUIIXZUPYXCHA-UHFFFAOYSA-N 0.000 claims description 3
• BOYOGJRLPORQHQ-CYBMUJFWSA-N (4-fluorophenyl)-[(3R)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@H](C=2ON=C(N=2)C=2NC=CC=2)CCC1 BOYOGJRLPORQHQ-CYBMUJFWSA-N 0.000 claims description 3
• SQMDCGNVPLTEKC-INIZCTEOSA-N (4-fluorophenyl)-[(3S)-3-[3-(1H-indol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC3=CC=CC=C3C=2)CCC1 SQMDCGNVPLTEKC-INIZCTEOSA-N 0.000 claims description 3
• PEJDLTDYANPRBU-AWEZNQCLSA-N (4-fluorophenyl)-[(3S)-3-[5-(1H-pyrrol-2-yl)tetrazol-2-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](N2N=C(N=N2)C=2NC=CC=2)CCC1 PEJDLTDYANPRBU-AWEZNQCLSA-N 0.000 claims description 3
• LEYCRBLXWJCRJH-NSHDSACASA-N (4-fluorophenyl)-[(3S)-3-[5-[5-(trifluoromethyl)-1H-imidazol-2-yl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(N=2)C(F)(F)F)CCC1 LEYCRBLXWJCRJH-NSHDSACASA-N 0.000 claims description 3
• UURXMBRSMGNNJJ-UHFFFAOYSA-N (4-fluorophenyl)-[3-[5-(1H-imidazol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CN=2)CCC1 UURXMBRSMGNNJJ-UHFFFAOYSA-N 0.000 claims description 3
• CASDWRSPIJRATR-UHFFFAOYSA-N (4-fluorophenyl)-[3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CC=2)CCC1 CASDWRSPIJRATR-UHFFFAOYSA-N 0.000 claims description 3
• RIYADNUXTBLENX-LBPRGKRZSA-N (6-fluoropyridin-3-yl)-[(3S)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=CC=2)CCC1 RIYADNUXTBLENX-LBPRGKRZSA-N 0.000 claims description 3
• KIIWYGFIAGRWCK-NSHDSACASA-N (6-fluoropyridin-3-yl)-[(3S)-3-[3-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=NC(F)=CC=2)=C1 KIIWYGFIAGRWCK-NSHDSACASA-N 0.000 claims description 3
• NPBWXMYQFSITMF-NSHDSACASA-N (6-fluoropyridin-3-yl)-[(3S)-3-[3-[4-(trifluoromethyl)-1H-pyrrol-2-yl]-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(C=2)C(F)(F)F)CCC1 NPBWXMYQFSITMF-NSHDSACASA-N 0.000 claims description 3
• NPNMZYZWXVIMHP-UHFFFAOYSA-N (6-fluoropyridin-3-yl)-[3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CC=2)CCC1 NPNMZYZWXVIMHP-UHFFFAOYSA-N 0.000 claims description 3
• 208000028698 Cognitive impairment Diseases 0.000 claims description 3
• QVXOZSLTORWKSR-NSHDSACASA-N [(3S)-3-[3-(4-bromo-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Br)C=2)CCC1 QVXOZSLTORWKSR-NSHDSACASA-N 0.000 claims description 3
• DHPFMOYDVDUNHK-JTQLQIEISA-N [(3S)-3-[3-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(3-fluoropyridin-4-yl)methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=C(Cl)C=2)CCC1 DHPFMOYDVDUNHK-JTQLQIEISA-N 0.000 claims description 3
• NVSAVHVPXFTLOY-JTQLQIEISA-N [(3S)-3-[3-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(5-methyl-1,2-oxazol-4-yl)methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2NC=C(Cl)C=2)=C1C NVSAVHVPXFTLOY-JTQLQIEISA-N 0.000 claims description 3
• ABRKSVQEXBIEIL-JTQLQIEISA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(3-fluoropyridin-4-yl)methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Cl)C=2)CCC1 ABRKSVQEXBIEIL-JTQLQIEISA-N 0.000 claims description 3
• FUZQYPIJFKDVBA-LBPRGKRZSA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Cl)C=2)CCC1 FUZQYPIJFKDVBA-LBPRGKRZSA-N 0.000 claims description 3
• DPCQYPIHDBOVBS-NSHDSACASA-N [(3S)-3-[5-(4-chloro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]-(6-fluoropyridin-3-yl)methanone Chemical compound C1=NC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(Cl)C=2)CCC1 DPCQYPIHDBOVBS-NSHDSACASA-N 0.000 claims description 3
• XVAABGNNUKIUAY-UHFFFAOYSA-N [3,3-dimethyl-5-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]-(4-fluorophenyl)methanone Chemical compound C1C(C)(C)CC(C=2ON=C(N=2)C=2NC=CC=2)CN1C(=O)C1=CC=C(F)C=C1 XVAABGNNUKIUAY-UHFFFAOYSA-N 0.000 claims description 3
• 230000003227 neuromodulating effect Effects 0.000 claims description 3
• IKIBDZSIUXXBPN-ZDUSSCGKSA-N (2-fluoropyridin-4-yl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)N=CC=2)=C1 IKIBDZSIUXXBPN-ZDUSSCGKSA-N 0.000 claims description 2
• SEYRJKFTKMQBRG-NSHDSACASA-N (3,4-difluorophenyl)-[(3S)-3-[3-(1H-imidazol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1C[C@@H](C=2ON=C(N=2)C=2NC=CN=2)CCC1 SEYRJKFTKMQBRG-NSHDSACASA-N 0.000 claims description 2
• YJCUKJKFBXZCNP-ZDUSSCGKSA-N (3,4-difluorophenyl)-[(3S)-3-[3-(4-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound CC1=CNC(C=2N=C(ON=2)[C@@H]2CN(CCC2)C(=O)C=2C=C(F)C(F)=CC=2)=C1 YJCUKJKFBXZCNP-ZDUSSCGKSA-N 0.000 claims description 2
• NYWQJTBZFYWELR-UHFFFAOYSA-N (3,4-difluorophenyl)-[3-[5-(1H-imidazol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=C(F)C(F)=CC=C1C(=O)N1CC(C=2N=C(ON=2)C=2NC=CN=2)CCC1 NYWQJTBZFYWELR-UHFFFAOYSA-N 0.000 claims description 2
• LXEQUBBUBQQIMY-JTQLQIEISA-N (3-fluoropyridin-4-yl)-[(3S)-3-[5-[4-(trifluoromethyl)-1H-pyrrol-2-yl]-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CN=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=C(C=2)C(F)(F)F)CCC1 LXEQUBBUBQQIMY-JTQLQIEISA-N 0.000 claims description 2
• CASDWRSPIJRATR-ZDUSSCGKSA-N (4-fluorophenyl)-[(3S)-3-[5-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound C1=CC(F)=CC=C1C(=O)N1C[C@@H](C=2N=C(ON=2)C=2NC=CC=2)CCC1 CASDWRSPIJRATR-ZDUSSCGKSA-N 0.000 claims description 2
• XHAISXHBWKOVNQ-LBPRGKRZSA-N (4-fluorophenyl)-[(3S)-3-[5-(4-fluoro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound FC1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=C1 XHAISXHBWKOVNQ-LBPRGKRZSA-N 0.000 claims description 2
• YXDHTPMKZWXQJY-LBPRGKRZSA-N (4-fluorophenyl)-[(3S)-3-[5-(4-nitro-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound [O-][N+](=O)C1=CNC(C=2ON=C(N=2)[C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=C1 YXDHTPMKZWXQJY-LBPRGKRZSA-N 0.000 claims description 2
• OPJOCZBZZGEFQF-AWEZNQCLSA-N (4-fluorophenyl)-[(3S)-3-[5-(5-methyl-1H-pyrrol-2-yl)-1,2,4-oxadiazol-3-yl]piperidin-1-yl]methanone Chemical compound N1C(C)=CC=C1C1=NC([C@@H]2CN(CCC2)C(=O)C=2C=CC(F)=CC=2)=NO1 OPJOCZBZZGEFQF-AWEZNQCLSA-N 0.000 claims description 2
• UKVAXKVWSLHODI-NSHDSACASA-N (5-methyl-1,2-oxazol-4-yl)-[(3S)-3-[3-(1H-pyrrol-2-yl)-1,2,4-oxadiazol-5-yl]piperidin-1-yl]methanone Chemical compound O1N=CC(C(=O)N2C[C@H](CCC2)C=2ON=C(N=2)C=2NC=CC=2)=C1C UKVAXKVWSLHODI-NSHDSACASA-N 0.000 claims description 2
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