HRP20120240T1 - Piridil piperidin antagonisti receptora za oreksin - Google Patents
Piridil piperidin antagonisti receptora za oreksin Download PDFInfo
- Publication number
- HRP20120240T1 HRP20120240T1 HR20120240T HRP20120240T HRP20120240T1 HR P20120240 T1 HRP20120240 T1 HR P20120240T1 HR 20120240 T HR20120240 T HR 20120240T HR P20120240 T HRP20120240 T HR P20120240T HR P20120240 T1 HRP20120240 T1 HR P20120240T1
- Authority
- HR
- Croatia
- Prior art keywords
- methyl
- methoxy
- pyridine
- piperidin
- methylpiperidin
- Prior art date
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- -1 Pyridyl piperidine Chemical compound 0.000 title abstract 2
- 229940123730 Orexin receptor antagonist Drugs 0.000 title 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 19
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims 22
- 150000002367 halogens Chemical class 0.000 claims 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 21
- 125000001424 substituent group Chemical group 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 9
- 239000001257 hydrogen Substances 0.000 claims 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 8
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000001624 naphthyl group Chemical group 0.000 claims 6
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 125000000623 heterocyclic group Chemical group 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 125000000304 alkynyl group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- NPFDWHQSDBWQLH-QZTJIDSGSA-N filorexant Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NPFDWHQSDBWQLH-QZTJIDSGSA-N 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001041 indolyl group Chemical group 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- QGSQYXJYCQQUOQ-HZPDHXFCSA-N (2-ethoxyphenyl)-[(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound CCOC1=CC=CC=C1C(=O)N1[C@H](C)CC[C@@H](COC=2N=CC(F)=CC=2)C1 QGSQYXJYCQQUOQ-HZPDHXFCSA-N 0.000 claims 1
- QGSQYXJYCQQUOQ-UHFFFAOYSA-N (2-ethoxyphenyl)-[5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound CCOC1=CC=CC=C1C(=O)N1C(C)CCC(COC=2N=CC(F)=CC=2)C1 QGSQYXJYCQQUOQ-UHFFFAOYSA-N 0.000 claims 1
- WLIOWIQYUCIZIF-HZPDHXFCSA-N (5-chloro-2-pyrimidin-2-ylphenyl)-[(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(Cl)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 WLIOWIQYUCIZIF-HZPDHXFCSA-N 0.000 claims 1
- WLIOWIQYUCIZIF-UHFFFAOYSA-N (5-chloro-2-pyrimidin-2-ylphenyl)-[5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(Cl)C=2)C=2N=CC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 WLIOWIQYUCIZIF-UHFFFAOYSA-N 0.000 claims 1
- GQCGSCPIPUSUBF-HUUCEWRRSA-N 3-[(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-(triazol-2-yl)benzoic acid Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)N1N=CC=N1)C)OC1=CC=C(F)C=N1 GQCGSCPIPUSUBF-HUUCEWRRSA-N 0.000 claims 1
- NAEPLEBEZUHESC-HZPDHXFCSA-N 3-[(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-pyrimidin-2-ylbenzoic acid Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NAEPLEBEZUHESC-HZPDHXFCSA-N 0.000 claims 1
- GQCGSCPIPUSUBF-CABCVRRESA-N 3-[(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-(triazol-2-yl)benzoic acid Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)N1N=CC=N1)C)OC1=CC=C(F)C=N1 GQCGSCPIPUSUBF-CABCVRRESA-N 0.000 claims 1
- NAEPLEBEZUHESC-CVEARBPZSA-N 3-[(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-pyrimidin-2-ylbenzoic acid Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NAEPLEBEZUHESC-CVEARBPZSA-N 0.000 claims 1
- GQCGSCPIPUSUBF-LSDHHAIUSA-N 3-[(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-(triazol-2-yl)benzoic acid Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)N1N=CC=N1)C)OC1=CC=C(F)C=N1 GQCGSCPIPUSUBF-LSDHHAIUSA-N 0.000 claims 1
- NAEPLEBEZUHESC-JKSUJKDBSA-N 3-[(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-pyrimidin-2-ylbenzoic acid Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NAEPLEBEZUHESC-JKSUJKDBSA-N 0.000 claims 1
- GQCGSCPIPUSUBF-GJZGRUSLSA-N 3-[(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-(triazol-2-yl)benzoic acid Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)N1N=CC=N1)C)OC1=CC=C(F)C=N1 GQCGSCPIPUSUBF-GJZGRUSLSA-N 0.000 claims 1
- NAEPLEBEZUHESC-HOTGVXAUSA-N 3-[(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-pyrimidin-2-ylbenzoic acid Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C=1)C(O)=O)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NAEPLEBEZUHESC-HOTGVXAUSA-N 0.000 claims 1
- GQCGSCPIPUSUBF-UHFFFAOYSA-N 3-[5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-(triazol-2-yl)benzoic acid Chemical compound C1N(C(=O)C=2C(=CC=C(C=2)C(O)=O)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 GQCGSCPIPUSUBF-UHFFFAOYSA-N 0.000 claims 1
- NAEPLEBEZUHESC-UHFFFAOYSA-N 3-[5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidine-1-carbonyl]-4-pyrimidin-2-ylbenzoic acid Chemical compound C1N(C(=O)C=2C(=CC=C(C=2)C(O)=O)C=2N=CC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 NAEPLEBEZUHESC-UHFFFAOYSA-N 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- BUKZOCXLRRIYGO-QZTJIDSGSA-N [(2r,5r)-2-methyl-5-(pyridin-2-yloxymethyl)piperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=CC=N1 BUKZOCXLRRIYGO-QZTJIDSGSA-N 0.000 claims 1
- PRMMHHDEYHWXHN-SJLPKXTDSA-N [(2r,5r)-2-methyl-5-[(3-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)C=1ON=C(C)N=1)C)OC1=NC=CC=C1C PRMMHHDEYHWXHN-SJLPKXTDSA-N 0.000 claims 1
- ULHPPVRNPDKLHF-RTBURBONSA-N [(2r,5r)-2-methyl-5-[(5-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(C)C=N1 ULHPPVRNPDKLHF-RTBURBONSA-N 0.000 claims 1
- RAGJBUUPALHONH-QZTJIDSGSA-N [(2r,5r)-2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=CC(C)=N1 RAGJBUUPALHONH-QZTJIDSGSA-N 0.000 claims 1
- DWAIQBVIUBRLON-RTBURBONSA-N [(2r,5r)-2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=CC(C)=N1 DWAIQBVIUBRLON-RTBURBONSA-N 0.000 claims 1
- KSTMILLDVYYLMO-WOJBJXKFSA-N [(2r,5r)-2-methyl-5-[(6-propan-2-ylpyridin-2-yl)oxymethyl]piperidin-1-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound CC(C)C1=CC=CC(OC[C@H]2CN([C@H](C)CC2)C(=O)C=2C(=CC=CC=2)C=2N=CC=CN=2)=N1 KSTMILLDVYYLMO-WOJBJXKFSA-N 0.000 claims 1
- ZAUJCYRLVOCYSI-RTBURBONSA-N [(2r,5r)-2-methyl-5-[[6-(1,3-oxazol-2-yl)pyridin-2-yl]oxymethyl]piperidin-1-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)C=1N=CC=CN=1)C)OC(N=1)=CC=CC=1C1=NC=CO1 ZAUJCYRLVOCYSI-RTBURBONSA-N 0.000 claims 1
- MFCVYFXYQDQCEB-HZPDHXFCSA-N [(2r,5r)-5-[(2-chloropyridin-3-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=CN=C1Cl MFCVYFXYQDQCEB-HZPDHXFCSA-N 0.000 claims 1
- GQLRTQAQSNZOGW-HZPDHXFCSA-N [(2r,5r)-5-[(2-chloropyridin-4-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=NC(Cl)=C1 GQLRTQAQSNZOGW-HZPDHXFCSA-N 0.000 claims 1
- OUORYKNVLOLCRN-HZPDHXFCSA-N [(2r,5r)-5-[(3-chloropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=NC=CC=C1Cl OUORYKNVLOLCRN-HZPDHXFCSA-N 0.000 claims 1
- LJTACBIQDXHUPX-IAGOWNOFSA-N [(2r,5r)-5-[(5-chloropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(Cl)C=N1 LJTACBIQDXHUPX-IAGOWNOFSA-N 0.000 claims 1
- GEVBXICJSKZXBY-QZTJIDSGSA-N [(2r,5r)-5-[(5-fluoro-4-methylpyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC(C)=C(F)C=N1 GEVBXICJSKZXBY-QZTJIDSGSA-N 0.000 claims 1
- MFIMQRPVKNJNCZ-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(1-methyl-4-phenylpyrazol-3-yl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CN(C)N=1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 MFIMQRPVKNJNCZ-IAGOWNOFSA-N 0.000 claims 1
- AZVRNCHGYXJASK-HUUCEWRRSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(1h-indol-7-yl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C=2NC=CC=2C=CC=1)C)OC1=CC=C(F)C=N1 AZVRNCHGYXJASK-HUUCEWRRSA-N 0.000 claims 1
- OYFDBWSFFPTFSO-HZPDHXFCSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-fluoro-6-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1F)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 OYFDBWSFFPTFSO-HZPDHXFCSA-N 0.000 claims 1
- ZPGQDOQESJVZOA-NVXWUHKLSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-methyl-5-phenyl-1,3-thiazol-4-yl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C1=C(SC(C)=N1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 ZPGQDOQESJVZOA-NVXWUHKLSA-N 0.000 claims 1
- OEJUMLBCJYKCGZ-RTBURBONSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-phenylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 OEJUMLBCJYKCGZ-RTBURBONSA-N 0.000 claims 1
- BOPQAOQVLBMURO-QZTJIDSGSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-phenylpyridin-3-yl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=NC=CC=1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 BOPQAOQVLBMURO-QZTJIDSGSA-N 0.000 claims 1
- JZFNVTJQHXSBPW-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-pyrazol-1-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=C1)C)OC1=CC=C(F)C=N1 JZFNVTJQHXSBPW-IAGOWNOFSA-N 0.000 claims 1
- NHPFQONZHFJUNT-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NHPFQONZHFJUNT-IAGOWNOFSA-N 0.000 claims 1
- SRNAGDGPIQRAFX-QZTJIDSGSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(3-phenylpyridin-2-yl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CN=1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 SRNAGDGPIQRAFX-QZTJIDSGSA-N 0.000 claims 1
- APHOGECNTJFIHX-QZTJIDSGSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(4-phenylpyridin-3-yl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=NC=1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 APHOGECNTJFIHX-QZTJIDSGSA-N 0.000 claims 1
- ADNQCBKNFSDDHY-HZPDHXFCSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(F)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 ADNQCBKNFSDDHY-HZPDHXFCSA-N 0.000 claims 1
- UCTJPSCONMENMI-WOJBJXKFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-phenylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 UCTJPSCONMENMI-WOJBJXKFSA-N 0.000 claims 1
- FXCKYYUAELZRMB-QZTJIDSGSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrazin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=NC=1)C)OC1=CC=C(F)C=N1 FXCKYYUAELZRMB-QZTJIDSGSA-N 0.000 claims 1
- DOEPPGGZCKVLIC-QZTJIDSGSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrazol-1-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=C1)C)OC1=CC=C(F)C=N1 DOEPPGGZCKVLIC-QZTJIDSGSA-N 0.000 claims 1
- HVWHSVKRUBHDPE-RTBURBONSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyridin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=CC=1)C)OC1=CC=C(F)C=N1 HVWHSVKRUBHDPE-RTBURBONSA-N 0.000 claims 1
- MRCBWUFLEJUWRT-RTBURBONSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyridin-3-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1C=NC=CC=1)C)OC1=CC=C(F)C=N1 MRCBWUFLEJUWRT-RTBURBONSA-N 0.000 claims 1
- OXEHRSNUHXWFQG-HUUCEWRRSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(1h-1,2,4-triazol-5-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)C=1NN=CN=1)C)OC1=CC=C(F)C=N1 OXEHRSNUHXWFQG-HUUCEWRRSA-N 0.000 claims 1
- CEUWCOPGMSWESG-IFMALSPDSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(2-phenylethyl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)CCC=1C=CC=CC=1)C)OC1=CC=C(F)C=N1 CEUWCOPGMSWESG-IFMALSPDSA-N 0.000 claims 1
- GRALYLLGLCRICT-HZPDHXFCSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 GRALYLLGLCRICT-HZPDHXFCSA-N 0.000 claims 1
- FXZLQVXTCQJPSD-HUUCEWRRSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1F)N1N=CC=N1)C)OC1=CC=C(F)C=N1 FXZLQVXTCQJPSD-HUUCEWRRSA-N 0.000 claims 1
- SGRJQSJLOQZHRN-NVXWUHKLSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SGRJQSJLOQZHRN-NVXWUHKLSA-N 0.000 claims 1
- NSZSJQFDRRSYLH-SJLPKXTDSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-pyrimidin-2-ylphenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NSZSJQFDRRSYLH-SJLPKXTDSA-N 0.000 claims 1
- PGLITYXHMZQGDR-HUUCEWRRSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(F)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 PGLITYXHMZQGDR-HUUCEWRRSA-N 0.000 claims 1
- GAEOPOYFGWGPHD-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1,3-oxazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1OC=CN=1)C)OC1=CC=C(F)C=N1 GAEOPOYFGWGPHD-IAGOWNOFSA-N 0.000 claims 1
- UHNNEXBYILYIFC-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1,3-thiazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1SC=CN=1)C)OC1=CC=C(F)C=N1 UHNNEXBYILYIFC-IAGOWNOFSA-N 0.000 claims 1
- ZPSIPDLVEBVHHA-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1,3-thiazol-4-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CSC=1)C)OC1=CC=C(F)C=N1 ZPSIPDLVEBVHHA-IAGOWNOFSA-N 0.000 claims 1
- HZMUAGSAWQJPQK-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1h-pyrazol-4-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C1=CNN=C1)C)OC1=CC=C(F)C=N1 HZMUAGSAWQJPQK-IAGOWNOFSA-N 0.000 claims 1
- BZKKCIGGJWLNNA-HZPDHXFCSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(tetrazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=NC=N1)C)OC1=CC=C(F)C=N1 BZKKCIGGJWLNNA-HZPDHXFCSA-N 0.000 claims 1
- SWJLISCOLSUHGG-IAGOWNOFSA-N [(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SWJLISCOLSUHGG-IAGOWNOFSA-N 0.000 claims 1
- VLYUROCUAUDRFJ-HZPDHXFCSA-N [(2r,5r)-5-[(6-bromopyridin-3-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=C(Br)N=C1 VLYUROCUAUDRFJ-HZPDHXFCSA-N 0.000 claims 1
- RAGJBUUPALHONH-MSOLQXFVSA-N [(2r,5s)-2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=CC(C)=N1 RAGJBUUPALHONH-MSOLQXFVSA-N 0.000 claims 1
- FXCKYYUAELZRMB-MSOLQXFVSA-N [(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrazin-2-ylphenyl)methanone Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=NC=1)C)OC1=CC=C(F)C=N1 FXCKYYUAELZRMB-MSOLQXFVSA-N 0.000 claims 1
- NPFDWHQSDBWQLH-MSOLQXFVSA-N [(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NPFDWHQSDBWQLH-MSOLQXFVSA-N 0.000 claims 1
- SGRJQSJLOQZHRN-WBVHZDCISA-N [(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SGRJQSJLOQZHRN-WBVHZDCISA-N 0.000 claims 1
- NSZSJQFDRRSYLH-AEFFLSMTSA-N [(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-pyrimidin-2-ylphenyl]methanone Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NSZSJQFDRRSYLH-AEFFLSMTSA-N 0.000 claims 1
- SWJLISCOLSUHGG-SJORKVTESA-N [(2r,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SWJLISCOLSUHGG-SJORKVTESA-N 0.000 claims 1
- RAGJBUUPALHONH-ZWKOTPCHSA-N [(2s,5r)-2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=CC(C)=N1 RAGJBUUPALHONH-ZWKOTPCHSA-N 0.000 claims 1
- FXCKYYUAELZRMB-ZWKOTPCHSA-N [(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrazin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=NC=1)C)OC1=CC=C(F)C=N1 FXCKYYUAELZRMB-ZWKOTPCHSA-N 0.000 claims 1
- NPFDWHQSDBWQLH-ZWKOTPCHSA-N [(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NPFDWHQSDBWQLH-ZWKOTPCHSA-N 0.000 claims 1
- SGRJQSJLOQZHRN-DOTOQJQBSA-N [(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SGRJQSJLOQZHRN-DOTOQJQBSA-N 0.000 claims 1
- NSZSJQFDRRSYLH-FUHWJXTLSA-N [(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-pyrimidin-2-ylphenyl]methanone Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NSZSJQFDRRSYLH-FUHWJXTLSA-N 0.000 claims 1
- SWJLISCOLSUHGG-DLBZAZTESA-N [(2s,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SWJLISCOLSUHGG-DLBZAZTESA-N 0.000 claims 1
- RAGJBUUPALHONH-ROUUACIJSA-N [(2s,5s)-2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)OC1=CC=CC(C)=N1 RAGJBUUPALHONH-ROUUACIJSA-N 0.000 claims 1
- FXCKYYUAELZRMB-ROUUACIJSA-N [(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrazin-2-ylphenyl)methanone Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=NC=1)C)OC1=CC=C(F)C=N1 FXCKYYUAELZRMB-ROUUACIJSA-N 0.000 claims 1
- NPFDWHQSDBWQLH-ROUUACIJSA-N [(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NPFDWHQSDBWQLH-ROUUACIJSA-N 0.000 claims 1
- SGRJQSJLOQZHRN-RDJZCZTQSA-N [(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SGRJQSJLOQZHRN-RDJZCZTQSA-N 0.000 claims 1
- NSZSJQFDRRSYLH-WMZOPIPTSA-N [(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-pyrimidin-2-ylphenyl]methanone Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(CO)C=1)C=1N=CC=CN=1)C)OC1=CC=C(F)C=N1 NSZSJQFDRRSYLH-WMZOPIPTSA-N 0.000 claims 1
- SWJLISCOLSUHGG-IRXDYDNUSA-N [(2s,5s)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC[C@@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 SWJLISCOLSUHGG-IRXDYDNUSA-N 0.000 claims 1
- FXMYGMSKBUUJHW-IAGOWNOFSA-N [2-(2-amino-1,3-thiazol-4-yl)phenyl]-[(2r,5r)-2-methyl-5-[(3-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=CC=1)C=1N=C(N)SC=1)C)OC1=NC=CC=C1C FXMYGMSKBUUJHW-IAGOWNOFSA-N 0.000 claims 1
- FXMYGMSKBUUJHW-UHFFFAOYSA-N [2-(2-amino-1,3-thiazol-4-yl)phenyl]-[2-methyl-5-[(3-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)C=2N=C(N)SC=2)C(C)CCC1COC1=NC=CC=C1C FXMYGMSKBUUJHW-UHFFFAOYSA-N 0.000 claims 1
- QICBTCGYWJLAKV-QZTJIDSGSA-N [2-(5-fluoropyridin-2-yl)-5-methylphenyl]-[(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)C=1N=CC(F)=CC=1)C)OC1=CC=C(F)C=N1 QICBTCGYWJLAKV-QZTJIDSGSA-N 0.000 claims 1
- QICBTCGYWJLAKV-UHFFFAOYSA-N [2-(5-fluoropyridin-2-yl)-5-methylphenyl]-[5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2N=CC(F)=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 QICBTCGYWJLAKV-UHFFFAOYSA-N 0.000 claims 1
- BUKZOCXLRRIYGO-UHFFFAOYSA-N [2-methyl-5-(pyridin-2-yloxymethyl)piperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=CC=N1 BUKZOCXLRRIYGO-UHFFFAOYSA-N 0.000 claims 1
- PRMMHHDEYHWXHN-UHFFFAOYSA-N [2-methyl-5-[(3-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(3-methyl-1,2,4-oxadiazol-5-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)C=2ON=C(C)N=2)C(C)CCC1COC1=NC=CC=C1C PRMMHHDEYHWXHN-UHFFFAOYSA-N 0.000 claims 1
- ULHPPVRNPDKLHF-UHFFFAOYSA-N [2-methyl-5-[(5-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(C)C=N1 ULHPPVRNPDKLHF-UHFFFAOYSA-N 0.000 claims 1
- RAGJBUUPALHONH-UHFFFAOYSA-N [2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=N2)C(C)CCC1COC1=CC=CC(C)=N1 RAGJBUUPALHONH-UHFFFAOYSA-N 0.000 claims 1
- DWAIQBVIUBRLON-UHFFFAOYSA-N [2-methyl-5-[(6-methylpyridin-2-yl)oxymethyl]piperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=CC(C)=N1 DWAIQBVIUBRLON-UHFFFAOYSA-N 0.000 claims 1
- KSTMILLDVYYLMO-UHFFFAOYSA-N [2-methyl-5-[(6-propan-2-ylpyridin-2-yl)oxymethyl]piperidin-1-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound CC(C)C1=CC=CC(OCC2CN(C(C)CC2)C(=O)C=2C(=CC=CC=2)C=2N=CC=CN=2)=N1 KSTMILLDVYYLMO-UHFFFAOYSA-N 0.000 claims 1
- ZAUJCYRLVOCYSI-UHFFFAOYSA-N [2-methyl-5-[[6-(1,3-oxazol-2-yl)pyridin-2-yl]oxymethyl]piperidin-1-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)C=2N=CC=CN=2)C(C)CCC1COC(N=1)=CC=CC=1C1=NC=CO1 ZAUJCYRLVOCYSI-UHFFFAOYSA-N 0.000 claims 1
- MFCVYFXYQDQCEB-UHFFFAOYSA-N [5-[(2-chloropyridin-3-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=N2)C(C)CCC1COC1=CC=CN=C1Cl MFCVYFXYQDQCEB-UHFFFAOYSA-N 0.000 claims 1
- GQLRTQAQSNZOGW-UHFFFAOYSA-N [5-[(2-chloropyridin-4-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=N2)C(C)CCC1COC1=CC=NC(Cl)=C1 GQLRTQAQSNZOGW-UHFFFAOYSA-N 0.000 claims 1
- OUORYKNVLOLCRN-UHFFFAOYSA-N [5-[(3-chloropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=N2)C(C)CCC1COC1=NC=CC=C1Cl OUORYKNVLOLCRN-UHFFFAOYSA-N 0.000 claims 1
- GEVBXICJSKZXBY-UHFFFAOYSA-N [5-[(5-fluoro-4-methylpyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)C(C)CCC1COC1=CC(C)=C(F)C=N1 GEVBXICJSKZXBY-UHFFFAOYSA-N 0.000 claims 1
- MFIMQRPVKNJNCZ-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(1-methyl-4-phenylpyrazol-3-yl)methanone Chemical compound C1N(C(=O)C=2C(=CN(C)N=2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 MFIMQRPVKNJNCZ-UHFFFAOYSA-N 0.000 claims 1
- AZVRNCHGYXJASK-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(1h-indol-7-yl)methanone Chemical compound C1N(C(=O)C=2C=3NC=CC=3C=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 AZVRNCHGYXJASK-UHFFFAOYSA-N 0.000 claims 1
- OYFDBWSFFPTFSO-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-fluoro-6-pyrimidin-2-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2F)C=2N=CC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 OYFDBWSFFPTFSO-UHFFFAOYSA-N 0.000 claims 1
- ZPGQDOQESJVZOA-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-methyl-5-phenyl-1,3-thiazol-4-yl)methanone Chemical compound C1N(C(=O)C2=C(SC(C)=N2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 ZPGQDOQESJVZOA-UHFFFAOYSA-N 0.000 claims 1
- OEJUMLBCJYKCGZ-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-phenylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 OEJUMLBCJYKCGZ-UHFFFAOYSA-N 0.000 claims 1
- BOPQAOQVLBMURO-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-phenylpyridin-3-yl)methanone Chemical compound C1N(C(=O)C=2C(=NC=CC=2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 BOPQAOQVLBMURO-UHFFFAOYSA-N 0.000 claims 1
- JZFNVTJQHXSBPW-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-pyrazol-1-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=C2)C(C)CCC1COC1=CC=C(F)C=N1 JZFNVTJQHXSBPW-UHFFFAOYSA-N 0.000 claims 1
- NHPFQONZHFJUNT-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(2-pyrimidin-2-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)C=2N=CC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 NHPFQONZHFJUNT-UHFFFAOYSA-N 0.000 claims 1
- SRNAGDGPIQRAFX-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(3-phenylpyridin-2-yl)methanone Chemical compound C1N(C(=O)C=2C(=CC=CN=2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 SRNAGDGPIQRAFX-UHFFFAOYSA-N 0.000 claims 1
- APHOGECNTJFIHX-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(4-phenylpyridin-3-yl)methanone Chemical compound C1N(C(=O)C=2C(=CC=NC=2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 APHOGECNTJFIHX-UHFFFAOYSA-N 0.000 claims 1
- ADNQCBKNFSDDHY-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-fluoro-2-pyrimidin-2-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=C(F)C=2)C=2N=CC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 ADNQCBKNFSDDHY-UHFFFAOYSA-N 0.000 claims 1
- UCTJPSCONMENMI-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-phenylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 UCTJPSCONMENMI-UHFFFAOYSA-N 0.000 claims 1
- FXCKYYUAELZRMB-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyrazin-2-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2N=CC=NC=2)C(C)CCC1COC1=CC=C(F)C=N1 FXCKYYUAELZRMB-UHFFFAOYSA-N 0.000 claims 1
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- HVWHSVKRUBHDPE-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-(5-methyl-2-pyridin-2-ylphenyl)methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2N=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 HVWHSVKRUBHDPE-UHFFFAOYSA-N 0.000 claims 1
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- CEUWCOPGMSWESG-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(2-phenylethyl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)CCC=2C=CC=CC=2)C(C)CCC1COC1=CC=C(F)C=N1 CEUWCOPGMSWESG-UHFFFAOYSA-N 0.000 claims 1
- GRALYLLGLCRICT-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 GRALYLLGLCRICT-UHFFFAOYSA-N 0.000 claims 1
- FXZLQVXTCQJPSD-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-fluoro-6-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2F)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 FXZLQVXTCQJPSD-UHFFFAOYSA-N 0.000 claims 1
- SGRJQSJLOQZHRN-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(CO)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 SGRJQSJLOQZHRN-UHFFFAOYSA-N 0.000 claims 1
- NSZSJQFDRRSYLH-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-(hydroxymethyl)-2-pyrimidin-2-ylphenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(CO)C=2)C=2N=CC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 NSZSJQFDRRSYLH-UHFFFAOYSA-N 0.000 claims 1
- PGLITYXHMZQGDR-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-fluoro-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(F)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 PGLITYXHMZQGDR-UHFFFAOYSA-N 0.000 claims 1
- GAEOPOYFGWGPHD-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1,3-oxazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2OC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 GAEOPOYFGWGPHD-UHFFFAOYSA-N 0.000 claims 1
- UHNNEXBYILYIFC-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1,3-thiazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2SC=CN=2)C(C)CCC1COC1=CC=C(F)C=N1 UHNNEXBYILYIFC-UHFFFAOYSA-N 0.000 claims 1
- ZPSIPDLVEBVHHA-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1,3-thiazol-4-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C=2N=CSC=2)C(C)CCC1COC1=CC=C(F)C=N1 ZPSIPDLVEBVHHA-UHFFFAOYSA-N 0.000 claims 1
- HZMUAGSAWQJPQK-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(1h-pyrazol-4-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)C2=CNN=C2)C(C)CCC1COC1=CC=C(F)C=N1 HZMUAGSAWQJPQK-UHFFFAOYSA-N 0.000 claims 1
- SWJLISCOLSUHGG-UHFFFAOYSA-N [5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 SWJLISCOLSUHGG-UHFFFAOYSA-N 0.000 claims 1
- VLYUROCUAUDRFJ-UHFFFAOYSA-N [5-[(6-bromopyridin-3-yl)oxymethyl]-2-methylpiperidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C1N(C(=O)C=2C(=CC=CC=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(Br)N=C1 VLYUROCUAUDRFJ-UHFFFAOYSA-N 0.000 claims 1
- DCQTZBWDNFZCPC-HUUCEWRRSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(Cl)C=1)N1N=CC=N1)C)OC1=CC=C(F)C=N1 DCQTZBWDNFZCPC-HUUCEWRRSA-N 0.000 claims 1
- DCQTZBWDNFZCPC-UHFFFAOYSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[5-[(5-fluoropyridin-2-yl)oxymethyl]-2-methylpiperidin-1-yl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(Cl)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(F)C=N1 DCQTZBWDNFZCPC-UHFFFAOYSA-N 0.000 claims 1
- FOHPFJVZGXQQAX-IAGOWNOFSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[5-(trifluoromethyl)pyridin-2-yl]oxymethyl]piperidin-1-yl]methanone Chemical compound C([C@@H]1CC[C@H](N(C1)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C)OC1=CC=C(C(F)(F)F)C=N1 FOHPFJVZGXQQAX-IAGOWNOFSA-N 0.000 claims 1
- FOHPFJVZGXQQAX-UHFFFAOYSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[2-methyl-5-[[5-(trifluoromethyl)pyridin-2-yl]oxymethyl]piperidin-1-yl]methanone Chemical compound C1N(C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)C(C)CCC1COC1=CC=C(C(F)(F)F)C=N1 FOHPFJVZGXQQAX-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims 1
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 208000019116 sleep disease Diseases 0.000 claims 1
- 208000020685 sleep-wake disease Diseases 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 108050000742 Orexin Receptor Proteins 0.000 abstract 3
- 102000008834 Orexin receptor Human genes 0.000 abstract 3
- 201000010099 disease Diseases 0.000 abstract 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 2
- 230000002265 prevention Effects 0.000 abstract 2
- 208000012902 Nervous system disease Diseases 0.000 abstract 1
- 208000025966 Neurological disease Diseases 0.000 abstract 1
- 239000005557 antagonist Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 230000000926 neurological effect Effects 0.000 abstract 1
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Classifications
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