CA2902135A1 - Azetidine amide derivatives as orexin receptor antagonists - Google Patents
Azetidine amide derivatives as orexin receptor antagonists Download PDFInfo
- Publication number
- CA2902135A1 CA2902135A1 CA2902135A CA2902135A CA2902135A1 CA 2902135 A1 CA2902135 A1 CA 2902135A1 CA 2902135 A CA2902135 A CA 2902135A CA 2902135 A CA2902135 A CA 2902135A CA 2902135 A1 CA2902135 A1 CA 2902135A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- triazol
- azetidin
- methyl
- oxadiazol
- 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.)
- Abandoned
Links
- -1 Azetidine amide Chemical class 0.000 title claims abstract description 92
- 229940123730 Orexin receptor antagonist Drugs 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 169
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims description 80
- 238000000034 method Methods 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 229910052736 halogen Inorganic materials 0.000 claims description 53
- 150000002367 halogens Chemical class 0.000 claims description 53
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 51
- 208000035475 disorder Diseases 0.000 claims description 37
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 35
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 34
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 30
- 125000001072 heteroaryl group Chemical group 0.000 claims description 28
- 208000019901 Anxiety disease Diseases 0.000 claims description 24
- 206010012335 Dependence Diseases 0.000 claims description 24
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 208000019116 sleep disease Diseases 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 15
- 125000004076 pyridyl group Chemical group 0.000 claims description 15
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 14
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 13
- 208000010877 cognitive disease Diseases 0.000 claims description 13
- 201000010099 disease Diseases 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 208000019022 Mood disease Diseases 0.000 claims description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 230000002265 prevention Effects 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 208000027559 Appetite disease Diseases 0.000 claims description 8
- 125000000335 thiazolyl group Chemical group 0.000 claims description 8
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 7
- 125000005549 heteroarylene group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 125000002393 azetidinyl group Chemical group 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 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
- CPFLJHAIJBNXIU-NRFANRHFSA-N (5-methyl-2-phenylphenyl)-[(2s)-2-[3-[2-(trifluoromethoxy)phenyl]-1h-1,2,4-triazol-5-yl]azetidin-1-yl]methanone Chemical compound N1([C@@H](CC1)C=1NN=C(N=1)C=1C(=CC=CC=1)OC(F)(F)F)C(=O)C1=CC(C)=CC=C1C1=CC=CC=C1 CPFLJHAIJBNXIU-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
- 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
- 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
- JTRBZPNNQMWVFP-KRWDZBQOSA-N [(2s)-2-[5-(3-chloro-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(Cl)=C1OC JTRBZPNNQMWVFP-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
- 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
- NVMMJCQLJCPAQZ-KRWDZBQOSA-N [4,5-dimethyl-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)C)=NOC=1C1=CC=CC=C1OC(F)(F)F NVMMJCQLJCPAQZ-KRWDZBQOSA-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
- 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
- 125000004273 azetidin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000004353 pyrazol-1-yl group Chemical group [H]C1=NN(*)C([H])=C1[H] 0.000 claims 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 166
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Classifications
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- A—HUMAN NECESSITIES
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- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
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- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| EP13158791 | 2013-03-12 | ||
| EP13158791.7 | 2013-03-12 | ||
| PCT/IB2014/059628 WO2014141065A1 (en) | 2013-03-12 | 2014-03-11 | Azetidine amide derivatives as orexin receptor antagonists |
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| LT2855453T (lt) | 2012-06-04 | 2017-02-27 | Actelion Pharmaceuticals Ltd. | Benzimidazolo prolino dariniai |
| US9493446B2 (en) | 2012-10-10 | 2016-11-15 | Actelion Pharmaceuticals Ltd. | Orexin receptor antagonists which are [ortho bi-(hetero-)aryl]-[2-(meta bi-(hetero-)aryl)-pyrrolidin-1-yl]-methanone derivatives |
| 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 |
| PT3077389T (pt) | 2013-12-03 | 2017-12-15 | Idorsia Pharmaceuticals Ltd | Forma cristalina de (s)-(2-(6-cloro-7-metil-1hbenzo[d]imidazol-2-il)-2-metilpirrolidin-1-il)(5-metoxi-2-(2h-1,2,3-triazol-2-il)fenil)metanona e a sua utilização como como antagonistas do receptor de orexina |
| SI3077391T1 (sl) | 2013-12-04 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Uporaba benzimidazol-prolinskih derivatov |
| EP3619199B1 (en) | 2017-05-03 | 2021-07-07 | Idorsia Pharmaceuticals Ltd | Preparation of 2-([1,2,3]triazol-2-yl)-benzoic acid derivatives |
| 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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| PT1289955E (pt) | 2000-06-16 | 2005-08-31 | Smithkline Beecham Plc | Piperidinas para utilizacao como antagonistas dos receptores da orexina |
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| EP2079690B1 (en) | 2006-09-29 | 2010-09-15 | Actelion Pharmaceuticals Ltd. | 3-aza-bicyclo[3.1.0]hexane derivatives |
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| LT2855453T (lt) | 2012-06-04 | 2017-02-27 | Actelion Pharmaceuticals Ltd. | Benzimidazolo prolino dariniai |
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2014
- 2014-03-11 EP EP14714392.9A patent/EP2970241A1/en not_active Withdrawn
- 2014-03-11 US US14/775,474 patent/US9403813B2/en not_active Expired - Fee Related
- 2014-03-11 CA CA2902135A patent/CA2902135A1/en not_active Abandoned
- 2014-03-11 JP JP2015562482A patent/JP2016510810A/ja active Pending
- 2014-03-11 CN CN201480015297.7A patent/CN105051040A/zh active Pending
- 2014-03-11 WO PCT/IB2014/059628 patent/WO2014141065A1/en not_active Ceased
- 2014-03-11 KR KR1020157028022A patent/KR20150130413A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JP2016510810A (ja) | 2016-04-11 |
| CN105051040A (zh) | 2015-11-11 |
| US20160024064A1 (en) | 2016-01-28 |
| KR20150130413A (ko) | 2015-11-23 |
| WO2014141065A1 (en) | 2014-09-18 |
| EP2970241A1 (en) | 2016-01-20 |
| US9403813B2 (en) | 2016-08-02 |
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| Date | Code | Title | Description |
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| FZDE | Dead |
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