JP2016510810A5 - - Google Patents
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- JP2016510810A5 JP2016510810A5 JP2015562482A JP2015562482A JP2016510810A5 JP 2016510810 A5 JP2016510810 A5 JP 2016510810A5 JP 2015562482 A JP2015562482 A JP 2015562482A JP 2015562482 A JP2015562482 A JP 2015562482A JP 2016510810 A5 JP2016510810 A5 JP 2016510810A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- methanone
- azetidin
- triazol
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- 125000001424 substituent group Chemical group 0.000 claims 22
- -1 oxadiazole-diyl Chemical group 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- 229910052736 halogen Inorganic materials 0.000 claims 7
- 150000002367 halogens Chemical class 0.000 claims 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 3
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 2
- 239000004480 active ingredient Substances 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000005549 heteroarylene group Chemical group 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- PXTRDUIXBONJAT-INIZCTEOSA-N (2-methyl-5-phenyl-1,3-thiazol-4-yl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2N=C(SC=2C=2C=CC=CC=2)C)=NC=1C1=CC=CC=C1OC(F)(F)F PXTRDUIXBONJAT-INIZCTEOSA-N 0.000 claims 1
- WJAVKAMJLUFNGC-FQEVSTJZSA-N (2-phenylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 WJAVKAMJLUFNGC-FQEVSTJZSA-N 0.000 claims 1
- YOMMAMLAEKBFAP-NRFANRHFSA-N (5-methyl-2-phenylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N1([C@@H](CC1)C=1ON=C(N=1)C=1C(=CC=CC=1)OC(F)(F)F)C(=O)C1=CC(C)=CC=C1C1=CC=CC=C1 YOMMAMLAEKBFAP-NRFANRHFSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000027559 Appetite disease Diseases 0.000 claims 1
- 206010012335 Dependence Diseases 0.000 claims 1
- 208000019454 Feeding and Eating disease Diseases 0.000 claims 1
- 208000019022 Mood disease Diseases 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- JTLJRVQNBMKZDI-FQEVSTJZSA-N [(2s)-2-[3-(2,5-dimethylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC(C)=CC=C1C JTLJRVQNBMKZDI-FQEVSTJZSA-N 0.000 claims 1
- GLQGXTZSKHQCMH-SFHVURJKSA-N [(2s)-2-[3-(2-chlorophenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC=C1Cl GLQGXTZSKHQCMH-SFHVURJKSA-N 0.000 claims 1
- LYYKWNVLVHCKFB-IBGZPJMESA-N [(2s)-2-[3-(2-ethoxy-3-fluorophenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=C(F)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 LYYKWNVLVHCKFB-IBGZPJMESA-N 0.000 claims 1
- WNPVWEYECZTFJN-INIZCTEOSA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-fluoro-5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(F)=C(OC)C=2)N2N=CC=N2)=N1 WNPVWEYECZTFJN-INIZCTEOSA-N 0.000 claims 1
- QEVORAQYJWWNCK-KRWDZBQOSA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=N1 QEVORAQYJWWNCK-KRWDZBQOSA-N 0.000 claims 1
- LQMOSTNDDQUZPY-SFHVURJKSA-N [(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 LQMOSTNDDQUZPY-SFHVURJKSA-N 0.000 claims 1
- SARRGDZBWKLYAF-SFHVURJKSA-N [(2s)-2-[3-(2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=CC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 SARRGDZBWKLYAF-SFHVURJKSA-N 0.000 claims 1
- RTSMIOKUBXCXSN-IBGZPJMESA-N [(2s)-2-[3-(2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC=C1C RTSMIOKUBXCXSN-IBGZPJMESA-N 0.000 claims 1
- UURIGNWNCNVBPD-QFIPXVFZSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-(2-phenylphenyl)methanone Chemical compound CC1=C(Cl)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=CC=2)C=2C=CC=CC=2)=N1 UURIGNWNCNVBPD-QFIPXVFZSA-N 0.000 claims 1
- DCQOXBJPZPFZLC-QHCPKHFHSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-(5-methyl-2-phenylphenyl)methanone Chemical compound N1([C@@H](CC1)C=1ON=C(N=1)C=1C(=C(Cl)C=CC=1)C)C(=O)C1=CC(C)=CC=C1C1=CC=CC=C1 DCQOXBJPZPFZLC-QHCPKHFHSA-N 0.000 claims 1
- JYFGNZSAXLBHMX-SFHVURJKSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[2-(dimethylamino)-5-phenyl-1,3-thiazol-4-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2N=C(SC=2C=2C=CC=CC=2)N(C)C)=NC=1C1=CC=CC(Cl)=C1C JYFGNZSAXLBHMX-SFHVURJKSA-N 0.000 claims 1
- LBFZDWZNFZCFTN-IBGZPJMESA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC(Cl)=C1C LBFZDWZNFZCFTN-IBGZPJMESA-N 0.000 claims 1
- OIGNSHLFYCBDJY-KRWDZBQOSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-chloro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=C(Cl)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=N1 OIGNSHLFYCBDJY-KRWDZBQOSA-N 0.000 claims 1
- PULMNWLUTSSJBJ-KRWDZBQOSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-fluoro-5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)F)OC)=NC=1C1=CC=CC(Cl)=C1C PULMNWLUTSSJBJ-KRWDZBQOSA-N 0.000 claims 1
- MZXQGKTUYBYETL-SFHVURJKSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C2=CC=C(C=C2N2N=CC=N2)C)=NC=1C1=CC=CC(Cl)=C1C MZXQGKTUYBYETL-SFHVURJKSA-N 0.000 claims 1
- HAOGPYPOEIIKFU-SFHVURJKSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-chloro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=C(Cl)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=C(Cl)C=2)N2N=CC=N2)=N1 HAOGPYPOEIIKFU-SFHVURJKSA-N 0.000 claims 1
- OOKVSHJMCQIHFA-SFHVURJKSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-chloro-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C2=C(C=C(C(=C2)Cl)C)N2N=CC=N2)=NC=1C1=CC=CC(Cl)=C1C OOKVSHJMCQIHFA-SFHVURJKSA-N 0.000 claims 1
- XABSGZKQRPNJSC-SFHVURJKSA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC(Cl)=C1C XABSGZKQRPNJSC-SFHVURJKSA-N 0.000 claims 1
- RLHMXBUVBZHSSE-IBGZPJMESA-N [(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC(Cl)=C1C RLHMXBUVBZHSSE-IBGZPJMESA-N 0.000 claims 1
- QUGFWCRVJYFFFS-INIZCTEOSA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-fluoro-5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)F)OC)=NC=1C1=CC=CC(F)=C1OC QUGFWCRVJYFFFS-INIZCTEOSA-N 0.000 claims 1
- HJDKRWJGSBWZFK-KRWDZBQOSA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=N1 HJDKRWJGSBWZFK-KRWDZBQOSA-N 0.000 claims 1
- HQHRHVVXQYRDCR-KRWDZBQOSA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC(F)=C1OC HQHRHVVXQYRDCR-KRWDZBQOSA-N 0.000 claims 1
- LBWZEGBRYDWCLD-SFHVURJKSA-N [(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=N1 LBWZEGBRYDWCLD-SFHVURJKSA-N 0.000 claims 1
- FXCHFTLQCHKYDZ-SFHVURJKSA-N [(2s)-2-[3-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C2=CC=C(C=C2N2N=CC=N2)C)=NC=1C1=CC=CC(F)=C1C FXCHFTLQCHKYDZ-SFHVURJKSA-N 0.000 claims 1
- GVFDXVKQDXCIBM-SFHVURJKSA-N [(2s)-2-[3-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC(F)=C1C GVFDXVKQDXCIBM-SFHVURJKSA-N 0.000 claims 1
- YIGGVJZHZCFJLK-IBGZPJMESA-N [(2s)-2-[3-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC(F)=C1C YIGGVJZHZCFJLK-IBGZPJMESA-N 0.000 claims 1
- DREBVPAPAKBWSB-IBGZPJMESA-N [(2s)-2-[3-(3-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=CC=CC(C=2N=C(ON=2)[C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=C1 DREBVPAPAKBWSB-IBGZPJMESA-N 0.000 claims 1
- NKQZQHLEYPDUFU-IBGZPJMESA-N [(2s)-2-[3-(3-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=CC=CC(C=2N=C(ON=2)[C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=C1 NKQZQHLEYPDUFU-IBGZPJMESA-N 0.000 claims 1
- INUGQCZFOVWYOH-KRWDZBQOSA-N [(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 INUGQCZFOVWYOH-KRWDZBQOSA-N 0.000 claims 1
- ACZVEIWPNAHIKZ-KRWDZBQOSA-N [(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(OC)C=2)N2N=CC=N2)=NO1 ACZVEIWPNAHIKZ-KRWDZBQOSA-N 0.000 claims 1
- VWAPJTCYQBYLJV-SFHVURJKSA-N [(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=NO1 VWAPJTCYQBYLJV-SFHVURJKSA-N 0.000 claims 1
- KRHUCICAAYFNCG-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=NO1 KRHUCICAAYFNCG-SFHVURJKSA-N 0.000 claims 1
- NWUOMBGAQQVYBN-INIZCTEOSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4-chloro-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=NO1 NWUOMBGAQQVYBN-INIZCTEOSA-N 0.000 claims 1
- FVVNULVSBLTYIJ-INIZCTEOSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC=CC(Cl)=C1OC FVVNULVSBLTYIJ-INIZCTEOSA-N 0.000 claims 1
- OEGZSCPWVIHGEV-KRWDZBQOSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=CC=2)N2N=CC=N2)=NO1 OEGZSCPWVIHGEV-KRWDZBQOSA-N 0.000 claims 1
- BDRONGXINZAOHD-KRWDZBQOSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-chloro-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(Cl)C=2)N2N=CC=N2)=NO1 BDRONGXINZAOHD-KRWDZBQOSA-N 0.000 claims 1
- DFTNMZQQCIARPX-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound COC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC=C(C)C=2)N2N=CC=N2)=NO1 DFTNMZQQCIARPX-SFHVURJKSA-N 0.000 claims 1
- PMPLHHCEDONMDL-FQEVSTJZSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-(5-methoxy-4-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2C=2N=CC=CN=2)C)OC)=NOC=1C1=CC=CC(Cl)=C1C PMPLHHCEDONMDL-FQEVSTJZSA-N 0.000 claims 1
- ZYAAECIWBVGBRR-QHCPKHFHSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-(5-methyl-2-phenylphenyl)methanone Chemical compound N1([C@@H](CC1)C=1N=C(ON=1)C=1C(=C(Cl)C=CC=1)C)C(=O)C1=CC(C)=CC=C1C1=CC=CC=C1 ZYAAECIWBVGBRR-QHCPKHFHSA-N 0.000 claims 1
- YUWCCHXLRVUFMI-FQEVSTJZSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-(5-methyl-2-pyrimidin-2-ylphenyl)methanone Chemical compound N1([C@@H](CC1)C=1N=C(ON=1)C=1C(=C(Cl)C=CC=1)C)C(=O)C1=CC(C)=CC=C1C1=NC=CC=N1 YUWCCHXLRVUFMI-FQEVSTJZSA-N 0.000 claims 1
- VGTPHDXDMLGZBB-KRWDZBQOSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[2-(triazol-2-yl)-4-(trifluoromethyl)phenyl]methanone Chemical compound CC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(=CC=2)C(F)(F)F)N2N=CC=N2)=NO1 VGTPHDXDMLGZBB-KRWDZBQOSA-N 0.000 claims 1
- QXNDPXJOGZQXCO-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC=CC=2)N2N=CC=N2)=NO1 QXNDPXJOGZQXCO-SFHVURJKSA-N 0.000 claims 1
- BAWRVITXGCLSQL-IBGZPJMESA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4,5-dimethyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NOC=1C1=CC=CC(Cl)=C1C BAWRVITXGCLSQL-IBGZPJMESA-N 0.000 claims 1
- IQCZVXGNNIRPOI-KRWDZBQOSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4-chloro-2-(triazol-2-yl)phenyl]methanone Chemical compound CC1=C(Cl)C=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=NO1 IQCZVXGNNIRPOI-KRWDZBQOSA-N 0.000 claims 1
- QOBNXSVQORJTRZ-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C2=CC=C(C=C2N2N=CC=N2)C)=NOC=1C1=CC=CC(Cl)=C1C QOBNXSVQORJTRZ-SFHVURJKSA-N 0.000 claims 1
- ZNWYWQNASHEVMR-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-chloro-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C2=C(C=C(C(=C2)Cl)C)N2N=CC=N2)=NOC=1C1=CC=CC(Cl)=C1C ZNWYWQNASHEVMR-SFHVURJKSA-N 0.000 claims 1
- ZBWQCFJDDIQKRB-SFHVURJKSA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NOC=1C1=CC=CC(Cl)=C1C ZBWQCFJDDIQKRB-SFHVURJKSA-N 0.000 claims 1
- FLQDYYVTSHSWMA-IBGZPJMESA-N [(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NOC=1C1=CC=CC(Cl)=C1C FLQDYYVTSHSWMA-IBGZPJMESA-N 0.000 claims 1
- ZLLNKWYYCZAOMM-KRWDZBQOSA-N [(2s)-2-[5-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NOC=1C1=CC=CC(F)=C1OC ZLLNKWYYCZAOMM-KRWDZBQOSA-N 0.000 claims 1
- XODWTMJEFQLUSV-IBGZPJMESA-N [(2s)-2-[5-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]-[5-methyl-2-(triazol-2-yl)phenyl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NOC=1C1=CC=CC(F)=C1C XODWTMJEFQLUSV-IBGZPJMESA-N 0.000 claims 1
- UCPSBKJOZPIGET-INIZCTEOSA-N [2-(dimethylamino)-5-phenyl-1,3-thiazol-4-yl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2N=C(SC=2C=2C=CC=CC=2)N(C)C)=NC=1C1=CC=CC=C1OC(F)(F)F UCPSBKJOZPIGET-INIZCTEOSA-N 0.000 claims 1
- DXOIVXMYAPKKGN-HNNXBMFYSA-N [2-(triazol-2-yl)-4-(trifluoromethyl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=NNC([C@H]2N(CC2)C(=O)C=2C(=CC(=CC=2)C(F)(F)F)N2N=CC=N2)=N1 DXOIVXMYAPKKGN-HNNXBMFYSA-N 0.000 claims 1
- AZUOKLYRZOAHGG-SFHVURJKSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound CCOC1=NC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=N1 AZUOKLYRZOAHGG-SFHVURJKSA-N 0.000 claims 1
- WJWLJCVPRGJCKV-SFHVURJKSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(3-fluoro-2-methoxyphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound COC1=C(F)C=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=N1 WJWLJCVPRGJCKV-SFHVURJKSA-N 0.000 claims 1
- YJLVUGVRJGAYCT-IBGZPJMESA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC(F)=C1C YJLVUGVRJGAYCT-IBGZPJMESA-N 0.000 claims 1
- MAGHQKODSAVJCO-KRWDZBQOSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC=C1OC(F)(F)F MAGHQKODSAVJCO-KRWDZBQOSA-N 0.000 claims 1
- BAWCOWUDXWBFRL-KRWDZBQOSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1NC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NC=1C1=CC=CC=C1OC(F)(F)F BAWCOWUDXWBFRL-KRWDZBQOSA-N 0.000 claims 1
- XLYJJZDMAYDCNN-SFHVURJKSA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(C)C=2)N2N=CC=N2)=NO1 XLYJJZDMAYDCNN-SFHVURJKSA-N 0.000 claims 1
- RCEJXBQPZVAORI-IBGZPJMESA-N [4,5-dimethyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)C)=NOC=1C1=CC=CC(F)=C1C RCEJXBQPZVAORI-IBGZPJMESA-N 0.000 claims 1
- UTROGYBGAXJJHW-HNNXBMFYSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=N1 UTROGYBGAXJJHW-HNNXBMFYSA-N 0.000 claims 1
- WAFPJAJOSTZPHL-HNNXBMFYSA-N [4-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=NNC([C@H]2N(CC2)C(=O)C=2C(=CC(Cl)=CC=2)N2N=CC=N2)=N1 WAFPJAJOSTZPHL-HNNXBMFYSA-N 0.000 claims 1
- TWOGTHWXONLTPL-KRWDZBQOSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NC=1C1=CC=CC(Cl)=C1C TWOGTHWXONLTPL-KRWDZBQOSA-N 0.000 claims 1
- NFWMNFOBAJJBIB-HNNXBMFYSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NC=1C1=CC=CC=C1OC(F)(F)F NFWMNFOBAJJBIB-HNNXBMFYSA-N 0.000 claims 1
- VMOMVQOYYDQOCJ-HNNXBMFYSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1NC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NC=1C1=CC=CC=C1OC(F)(F)F VMOMVQOYYDQOCJ-HNNXBMFYSA-N 0.000 claims 1
- MWJLXCJLYMSCEX-INIZCTEOSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(Cl)=C(OC)C=2)N2N=CC=N2)=NO1 MWJLXCJLYMSCEX-INIZCTEOSA-N 0.000 claims 1
- PYSYNIPKARHMJB-KRWDZBQOSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(3-chloro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC=CC(Cl)=C1C PYSYNIPKARHMJB-KRWDZBQOSA-N 0.000 claims 1
- DCCVKITYDJJUIE-KRWDZBQOSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC=CC(F)=C1C DCCVKITYDJJUIE-KRWDZBQOSA-N 0.000 claims 1
- CXSOMSKKVALFEI-HNNXBMFYSA-N [4-chloro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)Cl)OC)=NOC=1C1=CC=CC=C1OC(F)(F)F CXSOMSKKVALFEI-HNNXBMFYSA-N 0.000 claims 1
- MJIDNGCQJQMYMY-KRWDZBQOSA-N [4-fluoro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-(3-fluoro-2-methylphenyl)-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)F)OC)=NC=1C1=CC=CC(F)=C1C MJIDNGCQJQMYMY-KRWDZBQOSA-N 0.000 claims 1
- FLEPWMSNJHLEST-HNNXBMFYSA-N [4-fluoro-5-methoxy-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)F)OC)=NC=1C1=CC=CC=C1OC(F)(F)F FLEPWMSNJHLEST-HNNXBMFYSA-N 0.000 claims 1
- RQIZDINFFVTDAT-INIZCTEOSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C2=CC=C(C=C2N2N=CC=N2)C)=NC=1C1=CC=CC=C1OC(F)(F)F RQIZDINFFVTDAT-INIZCTEOSA-N 0.000 claims 1
- BTIVAWUUKLYCEZ-INIZCTEOSA-N [4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1NC([C@@H]2CCN2C(=O)C2=CC=C(C=C2N2N=CC=N2)C)=NC=1C1=CC=CC=C1OC(F)(F)F BTIVAWUUKLYCEZ-INIZCTEOSA-N 0.000 claims 1
- XMZZFGIXZKGXJC-INIZCTEOSA-N [5-chloro-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound FC(F)(F)OC1=CC=CC=C1C1=NOC([C@H]2N(CC2)C(=O)C=2C(=CC=C(Cl)C=2)N2N=CC=N2)=N1 XMZZFGIXZKGXJC-INIZCTEOSA-N 0.000 claims 1
- FYXHSPBAUOZDFS-INIZCTEOSA-N [5-chloro-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C2=C(C=C(C(=C2)Cl)C)N2N=CC=N2)=NC=1C1=CC=CC=C1OC(F)(F)F FYXHSPBAUOZDFS-INIZCTEOSA-N 0.000 claims 1
- QTOBFNXXJGXRBN-INIZCTEOSA-N [5-chloro-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1NC([C@@H]2CCN2C(=O)C2=C(C=C(C(=C2)Cl)C)N2N=CC=N2)=NC=1C1=CC=CC=C1OC(F)(F)F QTOBFNXXJGXRBN-INIZCTEOSA-N 0.000 claims 1
- KYNVYTOEXFMNLS-KRWDZBQOSA-N [5-chloro-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-(2-ethoxypyridin-3-yl)-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound CCOC1=NC=CC=C1C1=NC([C@H]2N(CC2)C(=O)C=2C(=CC(C)=C(Cl)C=2)N2N=CC=N2)=NO1 KYNVYTOEXFMNLS-KRWDZBQOSA-N 0.000 claims 1
- OGUYVKJUECVEBN-INIZCTEOSA-N [5-chloro-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C2=C(C=C(C(=C2)Cl)C)N2N=CC=N2)=NOC=1C1=CC=CC=C1OC(F)(F)F OGUYVKJUECVEBN-INIZCTEOSA-N 0.000 claims 1
- CTKBFWJKMMLDTD-INIZCTEOSA-N [5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC=C1OC(F)(F)F CTKBFWJKMMLDTD-INIZCTEOSA-N 0.000 claims 1
- BTUQEMRGQGEBRH-INIZCTEOSA-N [5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1NC([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NC=1C1=CC=CC=C1OC(F)(F)F BTUQEMRGQGEBRH-INIZCTEOSA-N 0.000 claims 1
- LUOTWXJCSHQCCF-INIZCTEOSA-N [5-methoxy-4-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C=C(C(=CC=2N2N=CC=N2)C)OC)=NOC=1C1=CC=CC=C1OC(F)(F)F LUOTWXJCSHQCCF-INIZCTEOSA-N 0.000 claims 1
- LILXODMUYCRFOF-KRWDZBQOSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]azetidin-1-yl]methanone Chemical compound N=1OC([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NC=1C1=CC=CC=C1OC(F)(F)F LILXODMUYCRFOF-KRWDZBQOSA-N 0.000 claims 1
- WBZDMZRGDRRDCR-KRWDZBQOSA-N [5-methyl-2-(triazol-2-yl)phenyl]-[(2s)-2-[5-[2-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-3-yl]azetidin-1-yl]methanone Chemical compound N=1C([C@@H]2CCN2C(=O)C=2C(=CC=C(C=2)C)N2N=CC=N2)=NOC=1C1=CC=CC=C1OC(F)(F)F WBZDMZRGDRRDCR-KRWDZBQOSA-N 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000002393 azetidinyl group Chemical group 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000035475 disorder Diseases 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000002971 oxazolyl group Chemical group 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 230000000069 prophylactic effect Effects 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP13158791.7 | 2013-03-12 | ||
| EP13158791 | 2013-03-12 | ||
| PCT/IB2014/059628 WO2014141065A1 (en) | 2013-03-12 | 2014-03-11 | Azetidine amide derivatives as orexin receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2016510810A JP2016510810A (ja) | 2016-04-11 |
| JP2016510810A5 true JP2016510810A5 (https=) | 2017-04-06 |
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| JP2015562482A Pending JP2016510810A (ja) | 2013-03-12 | 2014-03-11 | オレキシン受容体アンタゴニストとしてのアゼチジンアミド誘導体 |
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| EP (1) | EP2970241A1 (https=) |
| JP (1) | JP2016510810A (https=) |
| KR (1) | KR20150130413A (https=) |
| CN (1) | CN105051040A (https=) |
| CA (1) | CA2902135A1 (https=) |
| WO (1) | WO2014141065A1 (https=) |
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| ES2617863T3 (es) | 2012-06-04 | 2017-06-20 | Actelion Pharmaceuticals Ltd. | Derivados de bencimidazol-prolina |
| EA201500399A1 (ru) | 2012-10-10 | 2015-09-30 | Актелион Фармасьютиклз Лтд. | Антагонисты рецептора орексина, которые представляют собой производные [орто-би-(гетеро)арил]-[2-(мета-би-(гетеро)арил)пирролидин-1-ил]метанона |
| MY179862A (en) | 2013-12-03 | 2020-11-18 | Idorsia Pharmaceuticals Ltd | Crystalline form of (s)-(2-(6-chloro-7-methyl-1h-benzo[d]imidazol-2-yl)-2-methylpyrrolidin-1 -yl)(5-methoxy-2-(2h-1,2,3-triazol-2-yl)phenyl)methanone and its use as orexin receptor antagonists |
| UA119151C2 (uk) | 2013-12-03 | 2019-05-10 | Ідорсія Фармасьютікалз Лтд | КРИСТАЛІЧНА СОЛЬОВА ФОРМА (S)-(2-(6-ХЛОР-7-МЕТИЛ-1H-БЕНЗО[d]ІМІДАЗОЛ-2-ІЛ)-2-МЕТИЛПІРОЛІДИН-1-ІЛ)(5-МЕТОКСИ-2-(2H-1,2,3-ТРИАЗОЛ-2-ІЛ)ФЕНІЛ)МЕТАНОНУ ЯК АНТАГОНІСТ ОРЕКСИНОВОГО РЕЦЕПТОРА |
| SI3077391T1 (sl) | 2013-12-04 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Uporaba benzimidazol-prolinskih derivatov |
| LT3619199T (lt) | 2017-05-03 | 2021-09-27 | Idorsia Pharmaceuticals Ltd | 2-([1,2,3]triazol-2-il)-benzenkarboksirūgšties darinių gamyba |
| CN109810067B (zh) * | 2017-11-20 | 2022-05-20 | 扬子江药业集团有限公司 | 一种苏沃雷生中间体的制备方法 |
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-
2014
- 2014-03-11 CA CA2902135A patent/CA2902135A1/en not_active Abandoned
- 2014-03-11 EP EP14714392.9A patent/EP2970241A1/en not_active Withdrawn
- 2014-03-11 CN CN201480015297.7A patent/CN105051040A/zh active Pending
- 2014-03-11 US US14/775,474 patent/US9403813B2/en not_active Expired - Fee Related
- 2014-03-11 KR KR1020157028022A patent/KR20150130413A/ko not_active Withdrawn
- 2014-03-11 JP JP2015562482A patent/JP2016510810A/ja active Pending
- 2014-03-11 WO PCT/IB2014/059628 patent/WO2014141065A1/en not_active Ceased
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