JP2019517455A5 - - Google Patents
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- Publication number
- JP2019517455A5 JP2019517455A5 JP2018552704A JP2018552704A JP2019517455A5 JP 2019517455 A5 JP2019517455 A5 JP 2019517455A5 JP 2018552704 A JP2018552704 A JP 2018552704A JP 2018552704 A JP2018552704 A JP 2018552704A JP 2019517455 A5 JP2019517455 A5 JP 2019517455A5
- Authority
- JP
- Japan
- Prior art keywords
- sulfonyl
- benzene
- trifluoromethoxy
- pyridin
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims 43
- 150000003839 salts Chemical class 0.000 claims 23
- 125000005843 halogen group Chemical group 0.000 claims 21
- 125000000217 alkyl group Chemical group 0.000 claims 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 16
- 239000003814 drug Substances 0.000 claims 15
- 229940124597 therapeutic agent Drugs 0.000 claims 13
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 11
- 125000003545 alkoxy group Chemical group 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 11
- 229910052757 nitrogen Inorganic materials 0.000 claims 11
- 229910052760 oxygen Inorganic materials 0.000 claims 11
- 229910052717 sulfur Inorganic materials 0.000 claims 11
- 201000003883 Cystic fibrosis Diseases 0.000 claims 9
- 239000008194 pharmaceutical composition Substances 0.000 claims 8
- 125000001781 1,3,4-oxadiazolyl group Chemical group 0.000 claims 3
- WOXOLLSAICIZNO-UHFFFAOYSA-N [5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)CO WOXOLLSAICIZNO-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000000335 thiazolyl group Chemical group 0.000 claims 3
- 125000004504 1,2,4-oxadiazolyl group Chemical group 0.000 claims 2
- 125000004520 1,3,4-thiadiazolyl group Chemical group 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- RGSUYUQKDFLNQY-SFHVURJKSA-N (1S)-1-[5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]-2-phenylethanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)[C@H](CC1=CC=CC=C1)O RGSUYUQKDFLNQY-SFHVURJKSA-N 0.000 claims 1
- SVIYEFBUSOAYQQ-OAHLLOKOSA-N (2S)-2-[5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-thiadiazol-2-yl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(S1)[C@@](C(F)(F)F)(C)O SVIYEFBUSOAYQQ-OAHLLOKOSA-N 0.000 claims 1
- QPUMSIZJBUZSSL-SFHVURJKSA-N (S)-[5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]-phenylmethanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)[C@@H](O)C1=CC=CC=C1 QPUMSIZJBUZSSL-SFHVURJKSA-N 0.000 claims 1
- LFAWOLKBIDEZBO-UHFFFAOYSA-N 1-[5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]-2,2,2-trifluoroethanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)C(C(F)(F)F)O LFAWOLKBIDEZBO-UHFFFAOYSA-N 0.000 claims 1
- NOCHSTYDJNONRL-UHFFFAOYSA-N 2-(1,3,4-oxadiazol-2-yl)-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1C(=NN=C1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F NOCHSTYDJNONRL-UHFFFAOYSA-N 0.000 claims 1
- QVAWYCHUIQRKMJ-UHFFFAOYSA-N 2-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C1(CC1)C1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F QVAWYCHUIQRKMJ-UHFFFAOYSA-N 0.000 claims 1
- SEWTVVBWCIBCRT-UHFFFAOYSA-N 2-(3-tert-butyl-1,2,4-oxadiazol-5-yl)-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C(C)(C)(C)C1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F SEWTVVBWCIBCRT-UHFFFAOYSA-N 0.000 claims 1
- AHVWESHVIPMZFV-UHFFFAOYSA-N 2-(5-cyclohexyl-1,3,4-oxadiazol-2-yl)-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C1(CCCCC1)C1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F AHVWESHVIPMZFV-UHFFFAOYSA-N 0.000 claims 1
- UBATUHAOKRVMRY-UHFFFAOYSA-N 2-[3-(1-methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COC(C)C1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F UBATUHAOKRVMRY-UHFFFAOYSA-N 0.000 claims 1
- RWANNJNFJWJZRJ-UHFFFAOYSA-N 2-[3-(2-methoxyethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COCCC1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F RWANNJNFJWJZRJ-UHFFFAOYSA-N 0.000 claims 1
- TUPQCDKYEKGCIY-UHFFFAOYSA-N 2-[3-(2-methoxypropan-2-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COC(C)(C)C1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F TUPQCDKYEKGCIY-UHFFFAOYSA-N 0.000 claims 1
- BUMHFKUWKSVQSA-UHFFFAOYSA-N 2-[3-(cyclopropylmethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C1(CC1)CC1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F BUMHFKUWKSVQSA-UHFFFAOYSA-N 0.000 claims 1
- LRNHXRYWRCFIIT-UHFFFAOYSA-N 2-[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COCC1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F LRNHXRYWRCFIIT-UHFFFAOYSA-N 0.000 claims 1
- HGQIDXBJNFJGFS-UHFFFAOYSA-N 2-[3-(oxan-4-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1CCC(CC1)C1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F HGQIDXBJNFJGFS-UHFFFAOYSA-N 0.000 claims 1
- UOCUMVVRLXUYPK-UHFFFAOYSA-N 2-[3-(oxolan-2-ylmethyl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1C(CCC1)CC1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F UOCUMVVRLXUYPK-UHFFFAOYSA-N 0.000 claims 1
- LKFHQKZRUJXMPV-UHFFFAOYSA-N 2-[3-(oxolan-3-yl)-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1CC(CC1)C1=NOC(=N1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F LKFHQKZRUJXMPV-UHFFFAOYSA-N 0.000 claims 1
- ZXXXGUCODUSSIG-UHFFFAOYSA-N 2-[3-[(4-fluorophenoxy)methyl]-1,2,4-oxadiazol-5-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical class FC1=CC=C(OCC2=NOC(=N2)C2=NC=C(C=C2N)S(=O)(=O)C2=CC=C(C=C2)OC(F)(F)F)C=C1 ZXXXGUCODUSSIG-UHFFFAOYSA-N 0.000 claims 1
- UCPNPZINHHQZMN-UHFFFAOYSA-N 2-[5-(1-methoxyethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COC(C)C1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F UCPNPZINHHQZMN-UHFFFAOYSA-N 0.000 claims 1
- AKRJGNVFXMPYSH-UHFFFAOYSA-N 2-[5-(2-methoxyethoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical class COCCOCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F AKRJGNVFXMPYSH-UHFFFAOYSA-N 0.000 claims 1
- GSAJFWCFBNZIML-UHFFFAOYSA-N 2-[5-(2-methoxyethoxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COCCOCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F GSAJFWCFBNZIML-UHFFFAOYSA-N 0.000 claims 1
- POKPEGLINWBQAD-UHFFFAOYSA-N 2-[5-(cyclopentyloxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C1(CCCC1)OCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F POKPEGLINWBQAD-UHFFFAOYSA-N 0.000 claims 1
- FRGNYTVRPHEJRF-UHFFFAOYSA-N 2-[5-(cyclopropylmethoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C1(CC1)COCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F FRGNYTVRPHEJRF-UHFFFAOYSA-N 0.000 claims 1
- VMPDWAQANSTYGC-UHFFFAOYSA-N 2-[5-(cyclopropylmethoxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C1(CC1)COCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F VMPDWAQANSTYGC-UHFFFAOYSA-N 0.000 claims 1
- IBEXDKLPODXXFV-UHFFFAOYSA-N 2-[5-(difluoromethoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound FC(OCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)F IBEXDKLPODXXFV-UHFFFAOYSA-N 0.000 claims 1
- LZKVQYYFICZDPG-UHFFFAOYSA-N 2-[5-(difluoromethoxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound FC(OCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)F LZKVQYYFICZDPG-UHFFFAOYSA-N 0.000 claims 1
- FNEJIYILPURCDR-UHFFFAOYSA-N 2-[5-(ethoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C(C)OCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F FNEJIYILPURCDR-UHFFFAOYSA-N 0.000 claims 1
- BRHOUGDTPGNTNG-UHFFFAOYSA-N 2-[5-(ethoxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound C(C)OCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F BRHOUGDTPGNTNG-UHFFFAOYSA-N 0.000 claims 1
- DJAIUIVMCKEZFW-UHFFFAOYSA-N 2-[5-(methoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F DJAIUIVMCKEZFW-UHFFFAOYSA-N 0.000 claims 1
- TTXUSZZEPMIWNA-UHFFFAOYSA-N 2-[5-(methoxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound COCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F TTXUSZZEPMIWNA-UHFFFAOYSA-N 0.000 claims 1
- YQXUIYMCXKHUGP-UHFFFAOYSA-N 2-[5-(oxolan-3-yloxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1CC(CC1)OCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F YQXUIYMCXKHUGP-UHFFFAOYSA-N 0.000 claims 1
- PJGGPWZLFIHYAP-UHFFFAOYSA-N 2-[5-(oxolan-3-yloxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1CC(CC1)OCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F PJGGPWZLFIHYAP-UHFFFAOYSA-N 0.000 claims 1
- PZJMEMHATZSNGM-UHFFFAOYSA-N 2-[5-(phenoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O(C1=CC=CC=C1)CC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F PZJMEMHATZSNGM-UHFFFAOYSA-N 0.000 claims 1
- GIQYLDYUYDLUEO-UHFFFAOYSA-N 2-[5-(pyridin-3-yloxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound N1=CC(=CC=C1)OCC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F GIQYLDYUYDLUEO-UHFFFAOYSA-N 0.000 claims 1
- JXHWXDVYBQPQMF-UHFFFAOYSA-N 2-[5-(pyridin-3-yloxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound N1=CC(=CC=C1)OCC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F JXHWXDVYBQPQMF-UHFFFAOYSA-N 0.000 claims 1
- GOJAZAKMRYUGBQ-UHFFFAOYSA-N 2-[5-(trifluoromethoxymethyl)-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound FC(OC1=CC=C(C=C1)S(=O)(=O)C=1C=C(C(=NC=1)C=1OC(=NN=1)COC(F)(F)F)N)(F)F GOJAZAKMRYUGBQ-UHFFFAOYSA-N 0.000 claims 1
- BZWLMHFXJAJTNO-UHFFFAOYSA-N 2-[5-(trifluoromethoxymethyl)-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound FC(OC1=CC=C(C=C1)S(=O)(=O)C=1C=C(C(=NC=1)C=1SC(=NN=1)COC(F)(F)F)N)(F)F BZWLMHFXJAJTNO-UHFFFAOYSA-N 0.000 claims 1
- YJJFTJLRAPICTB-SECBINFHSA-N 2-[5-[(1R)-1-methoxyethyl]-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound CO[C@H](C)C1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F YJJFTJLRAPICTB-SECBINFHSA-N 0.000 claims 1
- UCPNPZINHHQZMN-SECBINFHSA-N 2-[5-[(1R)-1-methoxyethyl]-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound CO[C@H](C)C1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F UCPNPZINHHQZMN-SECBINFHSA-N 0.000 claims 1
- YJJFTJLRAPICTB-VIFPVBQESA-N 2-[5-[(1S)-1-methoxyethyl]-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound CO[C@@H](C)C1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F YJJFTJLRAPICTB-VIFPVBQESA-N 0.000 claims 1
- UCPNPZINHHQZMN-VIFPVBQESA-N 2-[5-[(1S)-1-methoxyethyl]-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound CO[C@@H](C)C1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F UCPNPZINHHQZMN-VIFPVBQESA-N 0.000 claims 1
- BUGJLENFQSLSGB-IBGZPJMESA-N 2-[5-[(S)-methoxy(phenyl)methyl]-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound CO[C@H](C1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=CC=CC=C1 BUGJLENFQSLSGB-IBGZPJMESA-N 0.000 claims 1
- OGZGCQWOENEPJW-IBGZPJMESA-N 2-[5-[(S)-methoxy(phenyl)methyl]-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical class CO[C@H](C1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=CC=CC=C1 OGZGCQWOENEPJW-IBGZPJMESA-N 0.000 claims 1
- RJRCXNXWAMTUFE-UHFFFAOYSA-N 2-[5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]-1,1,1-trifluoropropan-2-ol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)C(C(F)(F)F)(C)O RJRCXNXWAMTUFE-UHFFFAOYSA-N 0.000 claims 1
- XNCPIZTZFQCDAR-GFCCVEGCSA-N 2-[5-[[(2R)-oxolan-2-yl]methyl]-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1[C@H](CCC1)CC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F XNCPIZTZFQCDAR-GFCCVEGCSA-N 0.000 claims 1
- HGOMTAXEHIQMMW-GFCCVEGCSA-N 2-[5-[[(2R)-oxolan-2-yl]methyl]-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1[C@H](CCC1)CC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F HGOMTAXEHIQMMW-GFCCVEGCSA-N 0.000 claims 1
- XNCPIZTZFQCDAR-LBPRGKRZSA-N 2-[5-[[(2S)-oxolan-2-yl]methyl]-1,3,4-oxadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1[C@@H](CCC1)CC1=NN=C(O1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F XNCPIZTZFQCDAR-LBPRGKRZSA-N 0.000 claims 1
- HGOMTAXEHIQMMW-LBPRGKRZSA-N 2-[5-[[(2S)-oxolan-2-yl]methyl]-1,3,4-thiadiazol-2-yl]-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-3-amine Chemical compound O1[C@@H](CCC1)CC1=NN=C(S1)C1=NC=C(C=C1N)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F HGOMTAXEHIQMMW-LBPRGKRZSA-N 0.000 claims 1
- XCGIKWGGYZTWLG-UHFFFAOYSA-N 5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazole-2-carboxamide Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)C(=O)N XCGIKWGGYZTWLG-UHFFFAOYSA-N 0.000 claims 1
- AMBUCGCQNZDDOC-UHFFFAOYSA-N 5-amino-N-benzyl-6-[5-(hydroxymethyl)-1,3,4-oxadiazol-2-yl]-N-methylpyridine-3-sulfonamide Chemical compound NC=1C=C(C=NC=1C=1OC(=NN=1)CO)S(=O)(=O)N(C)CC1=CC=CC=C1 AMBUCGCQNZDDOC-UHFFFAOYSA-N 0.000 claims 1
- WZUNUMFWLBDZQY-UHFFFAOYSA-N CCC1=NOC(=N1)C2=C(C=C(C=N2)S(=O)(=O)C3=CC=C(C=C3)OC(F)(F)F)N Chemical compound CCC1=NOC(=N1)C2=C(C=C(C=N2)S(=O)(=O)C3=CC=C(C=C3)OC(F)(F)F)N WZUNUMFWLBDZQY-UHFFFAOYSA-N 0.000 claims 1
- XUJHPOBJPUEDIA-UHFFFAOYSA-N N-[[5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-thiadiazol-2-yl]methyl]cyclopropanecarbothioamide Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(S1)CNC(=S)C1CC1 XUJHPOBJPUEDIA-UHFFFAOYSA-N 0.000 claims 1
- QDLWEAFULOKMPL-UHFFFAOYSA-N [2-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3-thiazol-5-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C=1SC(=CN=1)CO QDLWEAFULOKMPL-UHFFFAOYSA-N 0.000 claims 1
- FTKLVTLVDZVGQZ-UHFFFAOYSA-N [5-[3-amino-4-bromo-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1Br)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)CO FTKLVTLVDZVGQZ-UHFFFAOYSA-N 0.000 claims 1
- GYKQLROARLMIRH-UHFFFAOYSA-N [5-[3-amino-4-chloro-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1Cl)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)CO GYKQLROARLMIRH-UHFFFAOYSA-N 0.000 claims 1
- JRTJKHDJHXHEOJ-UHFFFAOYSA-N [5-[3-amino-5-(2-propan-2-ylphenyl)sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=CC=C1)C(C)C)C1=NN=C(O1)CO JRTJKHDJHXHEOJ-UHFFFAOYSA-N 0.000 claims 1
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- GYASKYYQXOMZFG-UHFFFAOYSA-N [5-[3-amino-5-(benzenesulfonyl)pyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=CC=C1)C1=NN=C(O1)CO GYASKYYQXOMZFG-UHFFFAOYSA-N 0.000 claims 1
- DZEOJINSUBCKKO-UHFFFAOYSA-N [5-[3-amino-5-[2-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F)C1=NN=C(O1)CO DZEOJINSUBCKKO-UHFFFAOYSA-N 0.000 claims 1
- WWCUBNPYXAHVDM-UHFFFAOYSA-N [5-[3-amino-5-[3-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC(=CC=C1)OC(F)(F)F)C1=NN=C(O1)CO WWCUBNPYXAHVDM-UHFFFAOYSA-N 0.000 claims 1
- UTHFGDNAWQQTRG-UHFFFAOYSA-N [5-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methyl dihydrogen phosphate Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C1=NN=C(O1)COP(=O)(O)O UTHFGDNAWQQTRG-UHFFFAOYSA-N 0.000 claims 1
- QOBGZADYMZJBMX-UHFFFAOYSA-N [5-[3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C1=NN=C(O1)CO QOBGZADYMZJBMX-UHFFFAOYSA-N 0.000 claims 1
- BWOVMANFDLPAQC-UHFFFAOYSA-N [5-[3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-1,3,4-thiadiazol-2-yl]methanol Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C1=NN=C(S1)CO BWOVMANFDLPAQC-UHFFFAOYSA-N 0.000 claims 1
- KIZHWZGREZYJNC-UHFFFAOYSA-N [5-[3-amino-6-bromo-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC(=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)Br)C1=NN=C(O1)CO KIZHWZGREZYJNC-UHFFFAOYSA-N 0.000 claims 1
- UYZOEJUWGLJKHZ-UHFFFAOYSA-N [5-[3-amino-6-chloro-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-1,3,4-oxadiazol-2-yl]methanol Chemical compound NC=1C(=NC(=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)Cl)C1=NN=C(O1)CO UYZOEJUWGLJKHZ-UHFFFAOYSA-N 0.000 claims 1
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- 125000000623 heterocyclic group Chemical group 0.000 claims 1
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