AU2012335194B2 - 2-(1,2,3-triazol-2-yl)benzamide and 3-(1,2,3-triazol-2-yl)picolinamide derivatives as orexin receptor antagonists - Google Patents

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Publication number

AU2012335194B2

AU2012335194B2 AU2012335194A AU2012335194A AU2012335194B2 AU 2012335194 B2 AU2012335194 B2 AU 2012335194B2 AU 2012335194 A AU2012335194 A AU 2012335194A AU 2012335194 A AU2012335194 A AU 2012335194A AU 2012335194 B2 AU2012335194 B2 AU 2012335194B2

Authority

AU

Australia

Prior art keywords

triazol

benzyl

morpholin

phenyl

methanone

Prior art date

2011-11-08

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.)

Ceased

Links

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• TYWGXVSIWUAVQS-UHFFFAOYSA-N 2-(triazol-2-yl)benzamide Chemical compound NC(=O)C1=CC=CC=C1N1N=CC=N1 TYWGXVSIWUAVQS-UHFFFAOYSA-N 0.000 title abstract description 6
• XSQPATTVZNLZJE-UHFFFAOYSA-N 3-(triazol-2-yl)pyridine-2-carboxamide Chemical class NC(=O)C1=NC=CC=C1N1N=CC=N1 XSQPATTVZNLZJE-UHFFFAOYSA-N 0.000 title abstract description 6
• 229940123730 Orexin receptor antagonist Drugs 0.000 title description 8
• 150000001875 compounds Chemical class 0.000 claims description 288
• 238000000034 method Methods 0.000 claims description 118
• 229910052739 hydrogen Inorganic materials 0.000 claims description 58
• 239000001257 hydrogen Substances 0.000 claims description 58
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 55
• -1 methoxy, hydroxy Chemical group 0.000 claims description 44
• 125000000217 alkyl group Chemical group 0.000 claims description 42
• 208000035475 disorder Diseases 0.000 claims description 37
• 150000003839 salts Chemical class 0.000 claims description 37
• 229910052736 halogen Inorganic materials 0.000 claims description 32
• 150000002367 halogens Chemical class 0.000 claims description 32
• 150000002431 hydrogen Chemical group 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 125000001153 fluoro group Chemical group F* 0.000 claims description 27
• 208000019901 Anxiety disease Diseases 0.000 claims description 26
• 206010012335 Dependence Diseases 0.000 claims description 25
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 125000001424 substituent group Chemical group 0.000 claims description 20
• 201000010099 disease Diseases 0.000 claims description 18
• 125000003709 fluoroalkyl group Chemical group 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• 238000002360 preparation method Methods 0.000 claims description 17
• 208000019022 Mood disease Diseases 0.000 claims description 16
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 16
• 239000003814 drug Substances 0.000 claims description 16
• 208000019454 Feeding and Eating disease Diseases 0.000 claims description 15
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 14
• 125000004432 carbon atom Chemical group C* 0.000 claims description 14
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 14
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 13
• 125000001072 heteroaryl group Chemical group 0.000 claims description 12
• 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 11
• 230000002265 prevention Effects 0.000 claims description 11
• 208000027559 Appetite disease Diseases 0.000 claims description 10
• 125000001715 oxadiazolyl group Chemical group 0.000 claims description 10
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 10
• 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 9
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
• 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims description 9
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 9
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
• 125000002971 oxazolyl group Chemical group 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• 125000000335 thiazolyl group Chemical group 0.000 claims description 8
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
• GKPHAIOJCHBZCT-HXUWFJFHSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 GKPHAIOJCHBZCT-HXUWFJFHSA-N 0.000 claims description 4
• 125000004950 trifluoroalkyl group Chemical group 0.000 claims description 4
• SNOAPCQTEZAFRK-VQIMIIECSA-N [(2R,5R)-5-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]-2-methylmorpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=CC=C2)N2N=CC=N2)C)C=C(C=C1)N1N=CC=N1 SNOAPCQTEZAFRK-VQIMIIECSA-N 0.000 claims description 3
• PHEQMGRTEIENAJ-LJQANCHMSA-N [(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound Cc1ccc(C(=O)N2CCOC[C@H]2Cc2cc(ccc2Cl)-n2nccn2)c(c1)-n1nccn1 PHEQMGRTEIENAJ-LJQANCHMSA-N 0.000 claims description 3
• AKVDRUIVHSDXNM-GOSISDBHSA-N [(3r)-3-[(4-chloro-3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2N=CC=CN=2)Cl)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 AKVDRUIVHSDXNM-GOSISDBHSA-N 0.000 claims description 3
• HWCNAOSLUJKVML-LJQANCHMSA-N [(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C(=CC=1)F)=CC=1N1N=CC=N1 HWCNAOSLUJKVML-LJQANCHMSA-N 0.000 claims description 3
• CXGGFUAERWUYLI-GOSISDBHSA-N [(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)-4-(trifluoromethyl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C(F)(F)F)C(C=1)=CC=CC=1C=1N=CON=1 CXGGFUAERWUYLI-GOSISDBHSA-N 0.000 claims description 3
• CSOMRAVZERRDSF-GOSISDBHSA-N [(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C=1N=CON=1 CSOMRAVZERRDSF-GOSISDBHSA-N 0.000 claims description 3
• APWITTXYMQNNTN-LJQANCHMSA-N [(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)-4-(trifluoromethyl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C(F)(F)F)C(C=1)=CC=CC=1N1N=CC=N1 APWITTXYMQNNTN-LJQANCHMSA-N 0.000 claims description 3
• RFRBKJBYJXZXKQ-LJQANCHMSA-N [(3r)-3-[[4-methyl-3-(1,3-thiazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2SC=CN=2)C)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 RFRBKJBYJXZXKQ-LJQANCHMSA-N 0.000 claims description 3
• HCNLIVZSGOZAEH-LJQANCHMSA-N [2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 HCNLIVZSGOZAEH-LJQANCHMSA-N 0.000 claims description 3
• XOKDIMBLNFVNEH-HXUWFJFHSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C(=C1N1N=CC=N1)C)C)C(C(=CC=1)F)=CC=1N1N=CC=N1 XOKDIMBLNFVNEH-HXUWFJFHSA-N 0.000 claims description 3
• QEFAZNLAURABKO-OAQYLSRUSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C(=C1N1N=CC=N1)C)C)C(C=1)=CC=CC=1N1N=CC=N1 QEFAZNLAURABKO-OAQYLSRUSA-N 0.000 claims description 3
• NERGNQKZFUFHEN-HXUWFJFHSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 NERGNQKZFUFHEN-HXUWFJFHSA-N 0.000 claims description 3
• IARRCNRCFRHKHB-GOSISDBHSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)N2N=CC=N2)OCCN1C(=O)C1=CC=C(Cl)C=C1N1N=CC=N1 IARRCNRCFRHKHB-GOSISDBHSA-N 0.000 claims description 3
• ONVKTAGSXCPXIK-LJQANCHMSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)Cl)C(C=1)=CC=CC=1N1N=CC=N1 ONVKTAGSXCPXIK-LJQANCHMSA-N 0.000 claims description 3
• CLOOLVHJLDFMDV-LJQANCHMSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)Cl)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 CLOOLVHJLDFMDV-LJQANCHMSA-N 0.000 claims description 3
• LZAJTUGFVUQFAB-LJQANCHMSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C=1)=CC=CC=1C=1N=CON=1 LZAJTUGFVUQFAB-LJQANCHMSA-N 0.000 claims description 3
• 229910052799 carbon Inorganic materials 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
• BVVSWRIBSPAQPU-HXUWFJFHSA-N 4-(triazol-2-yl)-3-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholine-4-carbonyl]benzonitrile Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C#N)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 BVVSWRIBSPAQPU-HXUWFJFHSA-N 0.000 claims description 2
• RRSNAFVMJVWFGD-NHCUHLMSSA-N [(2R,5R)-2-ethyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC[C@@H]1CN([C@H](Cc2cccc(c2)-n2nccn2)CO1)C(=O)c1ccccc1-n1nccn1 RRSNAFVMJVWFGD-NHCUHLMSSA-N 0.000 claims description 2
• UJDZZHFYTLBQSA-FGZHOGPDSA-N [(2R,5R)-2-ethyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C(C)[C@@H]1CN([C@@H](CO1)CC1=CC(=CC=C1)N1N=CC=N1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1 UJDZZHFYTLBQSA-FGZHOGPDSA-N 0.000 claims description 2
• SBZFLVKAWPYIDI-FGZHOGPDSA-N [(2R,5R)-2-ethyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C(C)[C@@H]1CN([C@@H](CO1)CC1=CC(=CC=C1)N1N=CC=N1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1 SBZFLVKAWPYIDI-FGZHOGPDSA-N 0.000 claims description 2
• GTTJINSRAWFIHD-WIYYLYMNSA-N [(2R,5R)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C[C@@H]1CN([C@@H](CO1)CC1=CC(=CC=C1)C1=NC=CC=N1)C(=O)C1=C(C=CC=C1)N1N=CC=N1 GTTJINSRAWFIHD-WIYYLYMNSA-N 0.000 claims description 2
• QDURYEZFCXJVOM-DENIHFKCSA-N [(2R,5R)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C[C@@H]1CN([C@@H](CO1)CC1=CC(=CC=C1)C1=NC=CC=N1)C(=O)C1=C(C(=CC=C1)C)N1N=CC=N1 QDURYEZFCXJVOM-DENIHFKCSA-N 0.000 claims description 2
• STINWRWRNQHPGO-DENIHFKCSA-N [(2R,5R)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C[C@@H]1CN([C@@H](CO1)CC1=CC(=CC=C1)C1=NC=CC=N1)C(=O)C1=C(C=C(C=C1)C)N1N=CC=N1 STINWRWRNQHPGO-DENIHFKCSA-N 0.000 claims description 2
• ACKAOVNXPNOWIE-DENIHFKCSA-N [(2R,5R)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C[C@@H]1CN([C@H](Cc2cccc(c2)-c2ncccn2)CO1)C(=O)c1cc(C)ccc1-n1nccn1 ACKAOVNXPNOWIE-DENIHFKCSA-N 0.000 claims description 2
• OAHUTLZBMNCBFN-WIYYLYMNSA-N [(2R,5R)-5-[(2-fluoro-5-pyridazin-3-ylphenyl)methyl]-2-methylmorpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=C(C=C2)C)N2N=CC=N2)C)C=C(C=C1)C=1N=NC=CC1 OAHUTLZBMNCBFN-WIYYLYMNSA-N 0.000 claims description 2
• STUGMTDSOKPRBQ-WIYYLYMNSA-N [(2R,5R)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C[C@@H]1CN([C@H](Cc2cc(ccc2F)-c2ncccn2)CO1)C(=O)c1cccc(C)c1-n1nccn1 STUGMTDSOKPRBQ-WIYYLYMNSA-N 0.000 claims description 2
• HYSRABRBUHZYQJ-WIYYLYMNSA-N [(2R,5R)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=C(C=C2)C)N2N=CC=N2)C)C=C(C=C1)C1=NC=CC=N1 HYSRABRBUHZYQJ-WIYYLYMNSA-N 0.000 claims description 2
• AEIDDRZWBROWDG-WIYYLYMNSA-N [(2R,5R)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=CC(=C2)C)N2N=CC=N2)C)C=C(C=C1)C1=NC=CC=N1 AEIDDRZWBROWDG-WIYYLYMNSA-N 0.000 claims description 2
• OSHBRXGINANDJA-YLJYHZDGSA-N [(2R,5R)-5-[[2-fluoro-5-(triazol-1-yl)phenyl]methyl]-2-methylmorpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=CC(=C2)C)N2N=CC=N2)C)C=C(C=C1)N1N=NC=C1 OSHBRXGINANDJA-YLJYHZDGSA-N 0.000 claims description 2
• QOXZYZJSLRTDNB-YLJYHZDGSA-N [(2R,5R)-5-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]-2-methylmorpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C(=CC=C2)C)N2N=CC=N2)C)C=C(C=C1)N1N=CC=N1 QOXZYZJSLRTDNB-YLJYHZDGSA-N 0.000 claims description 2
• MRMSRUZHMOGZGF-YLJYHZDGSA-N [(2R,5R)-5-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]-2-methylmorpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=C(C=C2)C)N2N=CC=N2)C)C=C(C=C1)N1N=CC=N1 MRMSRUZHMOGZGF-YLJYHZDGSA-N 0.000 claims description 2
• IEJDUPAJXHWTNS-YLJYHZDGSA-N [(2R,5R)-5-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]-2-methylmorpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@@H]2CO[C@@H](CN2C(=O)C2=C(C=CC(=C2)C)N2N=CC=N2)C)C=C(C=C1)N1N=CC=N1 IEJDUPAJXHWTNS-YLJYHZDGSA-N 0.000 claims description 2
• QWFXFQGJPGRBQR-YLJYHZDGSA-N [(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 QWFXFQGJPGRBQR-YLJYHZDGSA-N 0.000 claims description 2
• CWXMVKZSRVPZAO-YLJYHZDGSA-N [(2r,5r)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 CWXMVKZSRVPZAO-YLJYHZDGSA-N 0.000 claims description 2
• BLNLRXMYYDRXJH-YLJYHZDGSA-N [(2r,5r)-5-[[2-fluoro-5-(triazol-1-yl)phenyl]methyl]-2-methylmorpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1N1C=CN=N1 BLNLRXMYYDRXJH-YLJYHZDGSA-N 0.000 claims description 2
• OBGUWOPMHXCGQJ-GOSISDBHSA-N [(3R)-3-[(4-hydroxy-3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound Oc1ccc(C[C@@H]2COCCN2C(=O)c2ccccc2-n2nccn2)cc1-c1ncccn1 OBGUWOPMHXCGQJ-GOSISDBHSA-N 0.000 claims description 2
• RDSLXYSTWOTMMZ-HXUWFJFHSA-N [(3R)-3-[(4-methyl-3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=C(C=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=CC=C2)N2N=CC=N2)C=C1)C1=NC=CC=N1 RDSLXYSTWOTMMZ-HXUWFJFHSA-N 0.000 claims description 2
• BAHLPIRZKQNNOE-GOSISDBHSA-N [(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound ClC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=CC=C2)N2N=CC=N2)C=C(C=C1)N1N=CC=N1 BAHLPIRZKQNNOE-GOSISDBHSA-N 0.000 claims description 2
• KJPCUIQPIJYTDA-HXUWFJFHSA-N [(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[3,4-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound Cc1ccc(C(=O)N2CCOC[C@H]2Cc2cc(ccc2Cl)-n2nccn2)c(c1C)-n1nccn1 KJPCUIQPIJYTDA-HXUWFJFHSA-N 0.000 claims description 2
• FIPXBPYXRCPALA-LJQANCHMSA-N [(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound Cc1cccc(C(=O)N2CCOC[C@H]2Cc2cc(ccc2Cl)-n2nccn2)c1-n1nccn1 FIPXBPYXRCPALA-LJQANCHMSA-N 0.000 claims description 2
• HZYFRDSVQFDLHM-LJQANCHMSA-N [(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound ClC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=CC(=C2)C)N2N=CC=N2)C=C(C=C1)N1N=CC=N1 HZYFRDSVQFDLHM-LJQANCHMSA-N 0.000 claims description 2
• YNLXALPSUPUEOW-GOSISDBHSA-N [(3R)-3-[[2-fluoro-3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=C(C=C2)C)N2N=CC=N2)C=CC=C1N1N=CC=N1 YNLXALPSUPUEOW-GOSISDBHSA-N 0.000 claims description 2
• HYFRBSMLWUEXKY-GOSISDBHSA-N [(3R)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)-4-(trifluoromethyl)phenyl]methanone Chemical compound Fc1ccc(cc1C[C@@H]1COCCN1C(=O)c1ccc(cc1-n1nccn1)C(F)(F)F)-n1nccn1 HYFRBSMLWUEXKY-GOSISDBHSA-N 0.000 claims description 2
• IKDFBCDOUXZRDH-LJQANCHMSA-N [(3R)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound Cc1cccc(C(=O)N2CCOC[C@H]2Cc2cc(ccc2F)-n2nccn2)c1-n1nccn1 IKDFBCDOUXZRDH-LJQANCHMSA-N 0.000 claims description 2
• JBGQDYPWYFNNTI-GOSISDBHSA-N [(3R)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound COc1ccc(c(c1)C(=O)N1CCOC[C@H]1Cc1cc(ccc1F)-n1nccn1)-n1nccn1 JBGQDYPWYFNNTI-GOSISDBHSA-N 0.000 claims description 2
• BNXAFMJKKZGLDN-LJQANCHMSA-N [(3R)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COc1cc(C(=O)N2CCOC[C@H]2Cc2cc(ccc2F)-n2nccn2)c(cc1C)-n1nccn1 BNXAFMJKKZGLDN-LJQANCHMSA-N 0.000 claims description 2
• SKTHZCLPOHWFMH-HXUWFJFHSA-N [(3R)-3-[[2-methyl-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=CC=C2)N2N=CC=N2)C=C(C=C1)N1N=CC=N1 SKTHZCLPOHWFMH-HXUWFJFHSA-N 0.000 claims description 2
• KJXCOZMMUXZQGE-GOSISDBHSA-N [(3R)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)-3-(trifluoromethyl)phenyl]methanone Chemical compound FC(F)(F)c1cccc(C(=O)N2CCOC[C@H]2Cc2cccc(c2)-n2nccn2)c1-n1nccn1 KJXCOZMMUXZQGE-GOSISDBHSA-N 0.000 claims description 2
• PNBXBOOTVNVZSH-LJQANCHMSA-N [(3R)-3-[[3-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound FC=1C=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=CC=C2)N2N=CC=N2)C=C(C1)N1N=CC=N1 PNBXBOOTVNVZSH-LJQANCHMSA-N 0.000 claims description 2
• JOKDLAIJHCOJRF-HXUWFJFHSA-N [(3R)-3-[[3-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound FC=1C=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=C(C=C2)C)N2N=CC=N2)C=C(C1)N1N=CC=N1 JOKDLAIJHCOJRF-HXUWFJFHSA-N 0.000 claims description 2
• KDSFEYCWXQWBSK-HXUWFJFHSA-N [(3r)-3-[(2-fluoro-5-pyridazin-3-ylphenyl)methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C(=CC=1)F)=CC=1C1=CC=CN=N1 KDSFEYCWXQWBSK-HXUWFJFHSA-N 0.000 claims description 2
• VLMPYJVCPJRPBH-HXUWFJFHSA-N [(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)C)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 VLMPYJVCPJRPBH-HXUWFJFHSA-N 0.000 claims description 2
• LUSDGIQGCBLNQS-HXUWFJFHSA-N [(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 LUSDGIQGCBLNQS-HXUWFJFHSA-N 0.000 claims description 2
• QIKVTMHZHYXNDE-HXUWFJFHSA-N [(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 QIKVTMHZHYXNDE-HXUWFJFHSA-N 0.000 claims description 2
• LZJVNRGGFLKPHX-JOCHJYFZSA-N [(3r)-3-[(2-methyl-5-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2C)N2N=CC=C2)OCCN1C(=O)C1=CC=CC(C)=C1N1N=CC=N1 LZJVNRGGFLKPHX-JOCHJYFZSA-N 0.000 claims description 2
• ZVAZIIXJYBKGIK-JOCHJYFZSA-N [(3r)-3-[(2-methyl-5-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C(=CC=1)C)=CC=1N1C=CC=N1 ZVAZIIXJYBKGIK-JOCHJYFZSA-N 0.000 claims description 2
• WOWXUSLEOFOYDZ-JOCHJYFZSA-N [(3r)-3-[(2-methyl-5-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C(=CC=1)C)=CC=1N1C=CC=N1 WOWXUSLEOFOYDZ-JOCHJYFZSA-N 0.000 claims description 2
• NSPDBKKKFMEMRB-HXUWFJFHSA-N [(3r)-3-[(3-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1C=CC=N1 NSPDBKKKFMEMRB-HXUWFJFHSA-N 0.000 claims description 2
• FYQCTNQQQSRWPV-HXUWFJFHSA-N [(3r)-3-[(3-pyridazin-3-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=CC=CN=N1 FYQCTNQQQSRWPV-HXUWFJFHSA-N 0.000 claims description 2
• RHBCBAZYIYZIMR-HXUWFJFHSA-N [(3r)-3-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 RHBCBAZYIYZIMR-HXUWFJFHSA-N 0.000 claims description 2
• YHWXLTYWQSZIKW-HXUWFJFHSA-N [(3r)-3-[(3-thiophen-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=CC=CS1 YHWXLTYWQSZIKW-HXUWFJFHSA-N 0.000 claims description 2
• CZERAVZVKNLXOP-LJQANCHMSA-N [(3r)-3-[(4-methoxy-3-pyrazin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2N=CC=NC=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 CZERAVZVKNLXOP-LJQANCHMSA-N 0.000 claims description 2
• HZTIXYMNAITACJ-LJQANCHMSA-N [(3r)-3-[(4-methoxy-3-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)N2N=CC=C2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 HZTIXYMNAITACJ-LJQANCHMSA-N 0.000 claims description 2
• FURKPFKLIIWSMR-LJQANCHMSA-N [(3r)-3-[(4-methoxy-3-pyridazin-3-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2N=NC=CC=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 FURKPFKLIIWSMR-LJQANCHMSA-N 0.000 claims description 2
• KKEOYRYRWVSPJZ-HXUWFJFHSA-N [(3r)-3-[(4-methoxy-3-pyridin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2N=CC=CC=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 KKEOYRYRWVSPJZ-HXUWFJFHSA-N 0.000 claims description 2
• OLMUIMIZDWOYII-OAQYLSRUSA-N [(3r)-3-[(4-methoxy-3-pyridin-3-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2C=NC=CC=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 OLMUIMIZDWOYII-OAQYLSRUSA-N 0.000 claims description 2
• OREIPZHDUFKPTP-LJQANCHMSA-N [(3r)-3-[(4-methoxy-3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2N=CC=CN=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 OREIPZHDUFKPTP-LJQANCHMSA-N 0.000 claims description 2
• PNGWMHMVJINNEB-LJQANCHMSA-N [(3r)-3-[(4-methoxy-3-thiophen-2-ylphenyl)methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2SC=CC=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 PNGWMHMVJINNEB-LJQANCHMSA-N 0.000 claims description 2
• OQWDRLJUBNCFEY-GOSISDBHSA-N [(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)C)C(C(=CC=1)F)=CC=1C=1N=CON=1 OQWDRLJUBNCFEY-GOSISDBHSA-N 0.000 claims description 2
• FJYYNLJIKKPGEW-GOSISDBHSA-N [(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C(=CC=1)F)=CC=1C=1N=CON=1 FJYYNLJIKKPGEW-GOSISDBHSA-N 0.000 claims description 2
• WVPNFJYCRRGGLI-GOSISDBHSA-N [(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C(=CC=1)F)=CC=1C=1N=CON=1 WVPNFJYCRRGGLI-GOSISDBHSA-N 0.000 claims description 2
• HVGUQKUDHLWJBC-GOSISDBHSA-N [(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)N2N=CC=N2)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 HVGUQKUDHLWJBC-GOSISDBHSA-N 0.000 claims description 2
• BUUBXHARNCJISZ-GOSISDBHSA-N [(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)OC)C(C(=CC=1)F)=CC=1N1N=CC=N1 BUUBXHARNCJISZ-GOSISDBHSA-N 0.000 claims description 2
• ORPRTCJZBDNPEM-LJQANCHMSA-N [(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C(=CC=1)F)=CC=1N1N=CC=N1 ORPRTCJZBDNPEM-LJQANCHMSA-N 0.000 claims description 2
• HVSHPQWTNYULCB-LJQANCHMSA-N [(3r)-3-[[3-(1,3-oxazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CO1 HVSHPQWTNYULCB-LJQANCHMSA-N 0.000 claims description 2
• FYEWZQAALXXWSM-LJQANCHMSA-N [(3r)-3-[[3-(1,3-thiazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CS1 FYEWZQAALXXWSM-LJQANCHMSA-N 0.000 claims description 2
• WXVVKTBDFXUAHG-OAQYLSRUSA-N [(3r)-3-[[3-(4-methylpyrimidin-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC=NC(C=2C=C(C[C@H]3N(CCOC3)C(=O)C=3C(=CC=CC=3)N3N=CC=N3)C=CC=2)=N1 WXVVKTBDFXUAHG-OAQYLSRUSA-N 0.000 claims description 2
• OYWUQQROZYATHC-JOCHJYFZSA-N [(3r)-3-[[3-(4-methylpyrimidin-2-yl)phenyl]methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC(C)=N1 OYWUQQROZYATHC-JOCHJYFZSA-N 0.000 claims description 2
• KXYYELXHLGICGL-HXUWFJFHSA-N [(3r)-3-[[3-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[3-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)C)C(C=1)=CC(Cl)=CC=1N1N=CC=N1 KXYYELXHLGICGL-HXUWFJFHSA-N 0.000 claims description 2
• LHHCFJSPYOKYPR-HXUWFJFHSA-N [(3r)-3-[[3-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C=1)=CC(Cl)=CC=1N1N=CC=N1 LHHCFJSPYOKYPR-HXUWFJFHSA-N 0.000 claims description 2
• BQSVOWNLNGKKOQ-MRXNPFEDSA-N [(3r)-3-[[4-chloro-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C2=NOC=N2)Cl)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 BQSVOWNLNGKKOQ-MRXNPFEDSA-N 0.000 claims description 2
• HUPRZYCCDOZRQO-QGZVFWFLSA-N [(3r)-3-[[4-methoxy-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C2=NOC=N2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 HUPRZYCCDOZRQO-QGZVFWFLSA-N 0.000 claims description 2
• UWCQHIQVETWOCJ-GOSISDBHSA-N [(3r)-3-[[4-methoxy-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[2-methyl-6-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C2=NOC=N2)OC)OCCN1C(=O)C1=C(C)C=CC=C1N1N=CC=N1 UWCQHIQVETWOCJ-GOSISDBHSA-N 0.000 claims description 2
• SHBXIINOQJVTRR-GOSISDBHSA-N [(3r)-3-[[4-methoxy-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C2=NOC=N2)OC)OCCN1C(=O)C1=CC=C(C)C=C1N1N=CC=N1 SHBXIINOQJVTRR-GOSISDBHSA-N 0.000 claims description 2
• PNRIERFKCYVVOG-GOSISDBHSA-N [(3r)-3-[[4-methoxy-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C2=NOC=N2)OC)OCCN1C(=O)C1=CC(C)=CC=C1N1N=CC=N1 PNRIERFKCYVVOG-GOSISDBHSA-N 0.000 claims description 2
• GHEMSERNBZGDLL-GOSISDBHSA-N [(3r)-3-[[4-methoxy-3-(1,3-oxazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2OC=CN=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 GHEMSERNBZGDLL-GOSISDBHSA-N 0.000 claims description 2
• CMSWWEXLVMHQNL-GOSISDBHSA-N [(3r)-3-[[4-methoxy-3-(1,3-thiazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C=2SC=CN=2)OC)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 CMSWWEXLVMHQNL-GOSISDBHSA-N 0.000 claims description 2
• XLQIWSDYHVBNIH-LJQANCHMSA-N [(3r)-3-[[4-methyl-3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)N2N=CC=N2)C)OCCN1C(=O)C1=CC=CC=C1N1N=CC=N1 XLQIWSDYHVBNIH-LJQANCHMSA-N 0.000 claims description 2
• MLWGTDLBQDBZDR-YLJYHZDGSA-N [(3r,5r)-3-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound C([C@@H]1COC[C@H](N1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 MLWGTDLBQDBZDR-YLJYHZDGSA-N 0.000 claims description 2
• HCNLIVZSGOZAEH-IBGZPJMESA-N [2-(triazol-2-yl)phenyl]-[(3s)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1COCCN1C(=O)C=1C(=CC=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 HCNLIVZSGOZAEH-IBGZPJMESA-N 0.000 claims description 2
• AHOIUZFUVOTFMM-QGZVFWFLSA-N [2-fluoro-3-methoxy-6-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1F)OC)N1N=CC=N1)C(C(=CC=1)F)=CC=1N1N=CC=N1 AHOIUZFUVOTFMM-QGZVFWFLSA-N 0.000 claims description 2
• VVTLUCANNQJJLA-GOSISDBHSA-N [2-fluoro-3-methoxy-6-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1F)OC)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 VVTLUCANNQJJLA-GOSISDBHSA-N 0.000 claims description 2
• KTJOHPLNNYAVJM-HXUWFJFHSA-N [2-fluoro-3-methyl-6-(triazol-2-yl)phenyl]-[(3r)-3-[(3-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1F)C)N1N=CC=N1)C(C=1)=CC=CC=1N1C=CC=N1 KTJOHPLNNYAVJM-HXUWFJFHSA-N 0.000 claims description 2
• VPQUBVYYWSMYEA-HXUWFJFHSA-N [2-fluoro-3-methyl-6-(triazol-2-yl)phenyl]-[(3r)-3-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1F)C)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 VPQUBVYYWSMYEA-HXUWFJFHSA-N 0.000 claims description 2
• STZDRKWMTBHWJI-GOSISDBHSA-N [2-fluoro-3-methyl-6-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1F)C)N1N=CC=N1)C(C(=CC=1)F)=CC=1N1N=CC=N1 STZDRKWMTBHWJI-GOSISDBHSA-N 0.000 claims description 2
• JNZNQAZDCIXPAH-LJQANCHMSA-N [2-fluoro-3-methyl-6-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1F)C)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 JNZNQAZDCIXPAH-LJQANCHMSA-N 0.000 claims description 2
• LCWVNVDNSNRWAR-QGZVFWFLSA-N [2-fluoro-6-(triazol-2-yl)phenyl]-[(3R)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound Fc1ccc(cc1C[C@@H]1COCCN1C(=O)c1c(F)cccc1-n1nccn1)-n1nccn1 LCWVNVDNSNRWAR-QGZVFWFLSA-N 0.000 claims description 2
• IEHBRXSPEXUDES-AUSIDOKSSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=C(C)C(C)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 IEHBRXSPEXUDES-AUSIDOKSSA-N 0.000 claims description 2
• KZQTUXCCKNLSIX-XMSQKQJNSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=C(C)C(C)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 KZQTUXCCKNLSIX-XMSQKQJNSA-N 0.000 claims description 2
• SWDMQWHTMPUUHA-XMSQKQJNSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=C(C)C(C)=CC=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 SWDMQWHTMPUUHA-XMSQKQJNSA-N 0.000 claims description 2
• DFLPJQGANRAIIM-OAQYLSRUSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C(=C1N1N=CC=N1)C)C)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 DFLPJQGANRAIIM-OAQYLSRUSA-N 0.000 claims description 2
• DADWYMXJDHTELJ-LJQANCHMSA-N [3,4-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C(=C1N1N=CC=N1)C)C)C(C(=CC=1)F)=CC=1C=1N=CON=1 DADWYMXJDHTELJ-LJQANCHMSA-N 0.000 claims description 2
• WBUINJWSFUWINW-HXUWFJFHSA-N [3,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=C(C)C=C(C=1)C)N1N=CC=N1)C(C=1)=CC=CC=1C=1N=CON=1 WBUINJWSFUWINW-HXUWFJFHSA-N 0.000 claims description 2
• PYRHLDRQRCTVES-OAQYLSRUSA-N [3,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=C(C)C=C(C=1)C)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 PYRHLDRQRCTVES-OAQYLSRUSA-N 0.000 claims description 2
• DUUOWDLWEJVCSI-VQIMIIECSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=C(Cl)C=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 DUUOWDLWEJVCSI-VQIMIIECSA-N 0.000 claims description 2
• YLJVEPVMPPEJBJ-VQIMIIECSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=C(Cl)C=CC=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 YLJVEPVMPPEJBJ-VQIMIIECSA-N 0.000 claims description 2
• YGTXKPMZPUBWGV-QGZVFWFLSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound Clc1ccc(cc1C[C@@H]1COCCN1C(=O)c1cccc(Cl)c1-n1nccn1)-n1nccn1 YGTXKPMZPUBWGV-QGZVFWFLSA-N 0.000 claims description 2
• JHVXWNVBCOMNJH-GOSISDBHSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)C=2N=CC=CN=2)OCCN1C(=O)C1=CC=CC(Cl)=C1N1N=CC=N1 JHVXWNVBCOMNJH-GOSISDBHSA-N 0.000 claims description 2
• CGFVLVBFXFGDNF-MRXNPFEDSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)C2=NOC=N2)OCCN1C(=O)C1=CC=CC(Cl)=C1N1N=CC=N1 CGFVLVBFXFGDNF-MRXNPFEDSA-N 0.000 claims description 2
• IVIQQEWOFAIBMX-QGZVFWFLSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)N2N=CC=N2)OCCN1C(=O)C1=CC=CC(Cl)=C1N1N=CC=N1 IVIQQEWOFAIBMX-QGZVFWFLSA-N 0.000 claims description 2
• IGNKAYVYFKMOBL-GOSISDBHSA-N [3-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)Cl)C(C=1)=CC=CC=1N1N=CC=N1 IGNKAYVYFKMOBL-GOSISDBHSA-N 0.000 claims description 2
• MWFCDHIHHZBJPV-QGZVFWFLSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)F)C(C=1)=CC=CC=1C=1N=CON=1 MWFCDHIHHZBJPV-QGZVFWFLSA-N 0.000 claims description 2
• BQVDTYWMMKIXOA-GOSISDBHSA-N [3-fluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)F)C(C=1)=CC=CC=1N1N=CC=N1 BQVDTYWMMKIXOA-GOSISDBHSA-N 0.000 claims description 2
• HMJZZKHOLAJQCJ-PGRDOPGGSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(2S,3R)-2-methyl-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C[C@H]1[C@H](N(CCO1)C(=O)C1=C(C(=CC=C1)C)N1N=CC=N1)CC1=CC(=CC=C1)N1N=CC=N1 HMJZZKHOLAJQCJ-PGRDOPGGSA-N 0.000 claims description 2
• WRLVGTRMEZGZFE-WIYYLYMNSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=C(C)C=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 WRLVGTRMEZGZFE-WIYYLYMNSA-N 0.000 claims description 2
• OQHUOGSZVADTEQ-OAQYLSRUSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(3R)-3-[[2-methyl-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound CC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C(=CC=C2)C)N2N=CC=N2)C=C(C=C1)N1N=CC=N1 OQHUOGSZVADTEQ-OAQYLSRUSA-N 0.000 claims description 2
• UGPJDNRZMHMMDB-LJQANCHMSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=CC=C(C=1N1N=CC=N1)C)C(C=1)=CC=CC=1C=1N=CON=1 UGPJDNRZMHMMDB-LJQANCHMSA-N 0.000 claims description 2
• UFYCDZYJXMCYQI-WIYYLYMNSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(3r,5r)-3-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COC[C@H](N1C(=O)C=1C(=C(C)C=CC=1)N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 UFYCDZYJXMCYQI-WIYYLYMNSA-N 0.000 claims description 2
• UFYCDZYJXMCYQI-GHTZIAJQSA-N [3-methyl-2-(triazol-2-yl)phenyl]-[(3s,5r)-3-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COC[C@@H](N1C(=O)C=1C(=C(C)C=CC=1)N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 UFYCDZYJXMCYQI-GHTZIAJQSA-N 0.000 claims description 2
• HMSWWKWVPAKARQ-MRXNPFEDSA-N [4,5-difluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)F)F)C(C(=CC=1)F)=CC=1N1N=CC=N1 HMSWWKWVPAKARQ-MRXNPFEDSA-N 0.000 claims description 2
• KOVCCWGOMZVONL-MRXNPFEDSA-N [4,5-difluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)F)F)C(C=1)=CC=CC=1C=1N=CON=1 KOVCCWGOMZVONL-MRXNPFEDSA-N 0.000 claims description 2
• DTAVCGIFLPXIFF-QGZVFWFLSA-N [4,5-difluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)F)F)C(C=1)=CC=CC=1N1N=CC=N1 DTAVCGIFLPXIFF-QGZVFWFLSA-N 0.000 claims description 2
• HJRBUDPCLJIXSQ-LJQANCHMSA-N [4,5-dimethoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)OC)OC)C(C=1)=CC=CC=1N1N=CC=N1 HJRBUDPCLJIXSQ-LJQANCHMSA-N 0.000 claims description 2
• QGLAATQFBFNUCL-DENIHFKCSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(C)=C(C)C=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 QGLAATQFBFNUCL-DENIHFKCSA-N 0.000 claims description 2
• PUBPGWFEGLTPSV-LJQANCHMSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)C)C)C(C(=CC=1)F)=CC=1C=1N=CON=1 PUBPGWFEGLTPSV-LJQANCHMSA-N 0.000 claims description 2
• DPAIDVFQHYLKSX-HXUWFJFHSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)C)C)C(C(=CC=1)F)=CC=1N1N=CC=N1 DPAIDVFQHYLKSX-HXUWFJFHSA-N 0.000 claims description 2
• BTNLZELUPKRKLO-HXUWFJFHSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)C)C)C(C=1)=CC=CC=1C=1N=CON=1 BTNLZELUPKRKLO-HXUWFJFHSA-N 0.000 claims description 2
• WWEKFLWFASRPJA-OAQYLSRUSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)C)C)C(C=1)=CC=CC=1N1N=CC=N1 WWEKFLWFASRPJA-OAQYLSRUSA-N 0.000 claims description 2
• DLTFUAAXCYAOLA-HXUWFJFHSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[4-methyl-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)C)C)C(C=1)=CC=C(C)C=1C=1N=CON=1 DLTFUAAXCYAOLA-HXUWFJFHSA-N 0.000 claims description 2
• QBNJEFPDYRBZMY-SIKLNZKXSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(3s,5r)-3-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COC[C@@H](N1C(=O)C=1C(=CC(C)=C(C)C=1)N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 QBNJEFPDYRBZMY-SIKLNZKXSA-N 0.000 claims description 2
• JOAYSRXNJHJJBL-DYESRHJHSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(Cl)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 JOAYSRXNJHJJBL-DYESRHJHSA-N 0.000 claims description 2
• JTIZTURJDNZRRX-OXQOHEQNSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(Cl)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 JTIZTURJDNZRRX-OXQOHEQNSA-N 0.000 claims description 2
• UIELPQGRXTWUBL-OXQOHEQNSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(Cl)=CC=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 UIELPQGRXTWUBL-OXQOHEQNSA-N 0.000 claims description 2
• RYPOYEQLSNWXDC-DNVCBOLYSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]-2-methylmorpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(Cl)=CC=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1N1N=CC=N1 RYPOYEQLSNWXDC-DNVCBOLYSA-N 0.000 claims description 2
• AOIUNCRFTKYDNL-GOSISDBHSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3R)-3-[[2-chloro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound Clc1ccc(C(=O)N2CCOC[C@H]2Cc2cc(ccc2Cl)-n2nccn2)c(c1)-n1nccn1 AOIUNCRFTKYDNL-GOSISDBHSA-N 0.000 claims description 2
• NNBZSPNSBCOMJO-LJQANCHMSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)C=2N=CC=CN=2)OCCN1C(=O)C1=CC=C(Cl)C=C1N1N=CC=N1 NNBZSPNSBCOMJO-LJQANCHMSA-N 0.000 claims description 2
• SBDNJLCIYJRHKZ-QGZVFWFLSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)C2=NOC=N2)OCCN1C(=O)C1=CC=C(Cl)C=C1N1N=CC=N1 SBDNJLCIYJRHKZ-QGZVFWFLSA-N 0.000 claims description 2
• BZOBPULTAMYVQD-HXUWFJFHSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-methyl-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2C)N2N=CC=N2)OCCN1C(=O)C1=CC=C(Cl)C=C1N1N=CC=N1 BZOBPULTAMYVQD-HXUWFJFHSA-N 0.000 claims description 2
• IUBQIPSNLRGHJH-GOSISDBHSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)Cl)C(C=1)=CC=CC=1C=1N=CON=1 IUBQIPSNLRGHJH-GOSISDBHSA-N 0.000 claims description 2
• JRGASLNNEVZZRN-QGZVFWFLSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)Cl)OC)C(C(=CC=1)F)=CC=1N1N=CC=N1 JRGASLNNEVZZRN-QGZVFWFLSA-N 0.000 claims description 2
• XKKKABNXFDRANJ-GOSISDBHSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)Cl)OC)C(C=1)=CC=CC=1N1N=CC=N1 XKKKABNXFDRANJ-GOSISDBHSA-N 0.000 claims description 2
• QCNZPQHXWUCBEP-LJQANCHMSA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)F)C(C=1)=CC=CC=1N1N=CC=N1 QCNZPQHXWUCBEP-LJQANCHMSA-N 0.000 claims description 2
• CZXWCWCRILWJKE-QGZVFWFLSA-N [4-fluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[4-methoxy-3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC=C(C(=C2)C2=NOC=N2)OC)OCCN1C(=O)C1=CC=C(F)C=C1N1N=CC=N1 CZXWCWCRILWJKE-QGZVFWFLSA-N 0.000 claims description 2
• ASCMSCIVNMZFPN-GOSISDBHSA-N [4-fluoro-5-methoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)F)OC)C(C=1)=CC=CC=1N1N=CC=N1 ASCMSCIVNMZFPN-GOSISDBHSA-N 0.000 claims description 2
• MRZOKJFVVJMJLC-LJQANCHMSA-N [4-methoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)OC)C(C=1)=CC=CC=1N1N=CC=N1 MRZOKJFVVJMJLC-LJQANCHMSA-N 0.000 claims description 2
• WOQOCTXBEIMJQF-XMSQKQJNSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(2r,3r)-2-methyl-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(CCO[C@@H]1C)C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 WOQOCTXBEIMJQF-XMSQKQJNSA-N 0.000 claims description 2
• XDAZJJGYLDZHNW-WIYYLYMNSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 XDAZJJGYLDZHNW-WIYYLYMNSA-N 0.000 claims description 2
• WOQOCTXBEIMJQF-PGRDOPGGSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(2s,3r)-2-methyl-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(CCO[C@H]1C)C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 WOQOCTXBEIMJQF-PGRDOPGGSA-N 0.000 claims description 2
• XDAZJJGYLDZHNW-GHTZIAJQSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(2s,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@@H](OC1)C)C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 XDAZJJGYLDZHNW-GHTZIAJQSA-N 0.000 claims description 2
• QRQCKASOXSZLKU-OAQYLSRUSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3R)-3-[[2-methyl-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound CC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=C(C=C2)C)N2N=CC=N2)C=C(C=C1)N1N=CC=N1 QRQCKASOXSZLKU-OAQYLSRUSA-N 0.000 claims description 2
• WYFQHYNFGVNXFG-OAQYLSRUSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[(3-pyrazol-1-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C=1)=CC=CC=1N1C=CC=N1 WYFQHYNFGVNXFG-OAQYLSRUSA-N 0.000 claims description 2
• DCMSTVVYTKCBDX-LJQANCHMSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C=1)=CC=CC=1C=1N=CON=1 DCMSTVVYTKCBDX-LJQANCHMSA-N 0.000 claims description 2
• DSAPJEHSDZGZQP-HXUWFJFHSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[4-methyl-3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C1=CC=C(C=C1N1N=CC=N1)C)C(C=1)=CC=C(C)C=1N1N=CC=N1 DSAPJEHSDZGZQP-HXUWFJFHSA-N 0.000 claims description 2
• FCVGUKJNRFNLDS-WIYYLYMNSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3r,5r)-3-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COC[C@H](N1C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 FCVGUKJNRFNLDS-WIYYLYMNSA-N 0.000 claims description 2
• FCVGUKJNRFNLDS-GHTZIAJQSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(3s,5r)-3-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COC[C@@H](N1C(=O)C=1C(=CC(C)=CC=1)N1N=CC=N1)C)C(C=1)=CC=CC=1N1N=CC=N1 FCVGUKJNRFNLDS-GHTZIAJQSA-N 0.000 claims description 2
• KKGJPPRCCVZKMV-DYESRHJHSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC=C(Cl)C=1)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 KKGJPPRCCVZKMV-DYESRHJHSA-N 0.000 claims description 2
• RWWXBFGEFGPVOA-OXQOHEQNSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-2-methyl-5-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC=C(Cl)C=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 RWWXBFGEFGPVOA-OXQOHEQNSA-N 0.000 claims description 2
• SMVHMTBUOLIQMT-OXQOHEQNSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]-2-methylmorpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC=C(Cl)C=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1C1=NC=CC=N1 SMVHMTBUOLIQMT-OXQOHEQNSA-N 0.000 claims description 2
• VZSCFYBYGCGNNT-DNVCBOLYSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2r,5r)-5-[[2-fluoro-5-(triazol-2-yl)phenyl]methyl]-2-methylmorpholin-4-yl]methanone Chemical compound C([C@H]1N(C[C@H](OC1)C)C(=O)C=1C(=CC=C(Cl)C=1)N1N=CC=N1)C(C(=CC=1)F)=CC=1N1N=CC=N1 VZSCFYBYGCGNNT-DNVCBOLYSA-N 0.000 claims description 2
• LFTFHZCWXHYQAL-LJQANCHMSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[(2-fluoro-5-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1CC2=CC(=CC=C2F)C=2N=CC=CN=2)OCCN1C(=O)C1=CC(Cl)=CC=C1N1N=CC=N1 LFTFHZCWXHYQAL-LJQANCHMSA-N 0.000 claims description 2
• LAINVSFGRYRKDA-HXUWFJFHSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(3r)-3-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)Cl)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 LAINVSFGRYRKDA-HXUWFJFHSA-N 0.000 claims description 2
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• TVALGRAHOLPKKR-GOSISDBHSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(1,2,4-oxadiazol-3-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)F)N1N=CC=N1)C(C=1)=CC=CC=1C=1N=CON=1 TVALGRAHOLPKKR-GOSISDBHSA-N 0.000 claims description 2
• HGBYUIVSHGPNIW-LJQANCHMSA-N [5-fluoro-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)F)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 HGBYUIVSHGPNIW-LJQANCHMSA-N 0.000 claims description 2
• GEVLHZAYQOXANJ-HXUWFJFHSA-N [5-methoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[(3-pyrimidin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)OC)N1N=CC=N1)C(C=1)=CC=CC=1C1=NC=CC=N1 GEVLHZAYQOXANJ-HXUWFJFHSA-N 0.000 claims description 2
• CWBKFZFKBHRMPJ-LJQANCHMSA-N [5-methoxy-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)OC)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 CWBKFZFKBHRMPJ-LJQANCHMSA-N 0.000 claims description 2
• TXOLBWQUYQXATH-HXUWFJFHSA-N [5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C=C(C(=CC=1N1N=CC=N1)C)OC)C(C=1)=CC=CC=1N1N=CC=N1 TXOLBWQUYQXATH-HXUWFJFHSA-N 0.000 claims description 2
• DZMITGRLYMROFK-WZONZLPQSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2r,3r)-2-methyl-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(CCO[C@@H]1C)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 DZMITGRLYMROFK-WZONZLPQSA-N 0.000 claims description 2
• DZMITGRLYMROFK-FDDCHVKYSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2s,3r)-2-methyl-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C([C@H]1N(CCO[C@H]1C)C(=O)C=1C(=CC=C(C)C=1)N1N=CC=N1)C(C=1)=CC=CC=1N1N=CC=N1 DZMITGRLYMROFK-FDDCHVKYSA-N 0.000 claims description 2
• HQLRZRZXOSRCFC-OAQYLSRUSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(3R)-3-[[2-methyl-5-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound CC1=C(C[C@H]2N(CCOC2)C(=O)C2=C(C=CC(=C2)C)N2N=CC=N2)C=C(C=C1)N1N=CC=N1 HQLRZRZXOSRCFC-OAQYLSRUSA-N 0.000 claims description 2
• AOBDPAOQKBBOMZ-XMMPIXPASA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(3R)-3-methyl-3-[[3-(triazol-2-yl)phenyl]methyl]morpholin-4-yl]methanone Chemical compound C[C@@]1(N(CCOC1)C(=O)C1=C(C=CC(=C1)C)N1N=CC=N1)CC1=CC(=CC=C1)N1N=CC=N1 AOBDPAOQKBBOMZ-XMMPIXPASA-N 0.000 claims description 2
• WQKDFCTZXNZINF-OAQYLSRUSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(3r)-3-[(3-pyrazin-2-ylphenyl)methyl]morpholin-4-yl]methanone Chemical compound C([C@@H]1COCCN1C(=O)C=1C(=CC=C(C=1)C)N1N=CC=N1)C(C=1)=CC=CC=1C1=CN=CC=N1 WQKDFCTZXNZINF-OAQYLSRUSA-N 0.000 claims description 2
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• NMYODLKTGUEPAQ-CQSZACIVSA-N tert-butyl (3R)-3-[(3-iodophenyl)methyl]morpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOC[C@H]1Cc1cccc(I)c1 NMYODLKTGUEPAQ-CQSZACIVSA-N 0.000 description 1
• HJYNLENYMULSAS-UHFFFAOYSA-N tert-butyl 3-oxomorpholine-4-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCOCC1=O HJYNLENYMULSAS-UHFFFAOYSA-N 0.000 description 1
• BVJYFSNMLDPCMF-GFCCVEGCSA-N tert-butyl N-[(2R)-1-(3-iodophenyl)-3-oxopropan-2-yl]carbamate Chemical compound CC(C)(C)OC(=O)N[C@H](Cc1cccc(I)c1)C=O BVJYFSNMLDPCMF-GFCCVEGCSA-N 0.000 description 1
• WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
• WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
• 238000002560 therapeutic procedure Methods 0.000 description 1
• 230000000699 topical effect Effects 0.000 description 1
• 230000002103 transcriptional effect Effects 0.000 description 1
• 238000011830 transgenic mouse model Methods 0.000 description 1
• 230000007704 transition Effects 0.000 description 1
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
• 230000002618 waking effect Effects 0.000 description 1
• 230000003313 weakening effect Effects 0.000 description 1
• 230000003936 working memory Effects 0.000 description 1