JP2018516932A5 - - Google Patents
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- JP2018516932A5 JP2018516932A5 JP2017562678A JP2017562678A JP2018516932A5 JP 2018516932 A5 JP2018516932 A5 JP 2018516932A5 JP 2017562678 A JP2017562678 A JP 2017562678A JP 2017562678 A JP2017562678 A JP 2017562678A JP 2018516932 A5 JP2018516932 A5 JP 2018516932A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- sulfonyl
- phenyl
- pyridine
- carboxamide
- 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.)
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- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 209
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 185
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 114
- -1 One or more -OH Chemical group 0.000 claims 101
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 58
- 125000001153 fluoro group Chemical group F* 0.000 claims 51
- 125000000217 alkyl group Chemical group 0.000 claims 46
- 125000003545 alkoxy group Chemical group 0.000 claims 43
- 150000003839 salts Chemical class 0.000 claims 43
- 150000001875 compounds Chemical class 0.000 claims 42
- 125000005843 halogen group Chemical group 0.000 claims 31
- 229910052757 nitrogen Inorganic materials 0.000 claims 30
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims 27
- 125000005842 heteroatom Chemical group 0.000 claims 25
- 229910052760 oxygen Inorganic materials 0.000 claims 25
- 229910052717 sulfur Inorganic materials 0.000 claims 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 21
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims 20
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 17
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 12
- 125000000623 heterocyclic group Chemical group 0.000 claims 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 9
- 125000002950 monocyclic group Chemical group 0.000 claims 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical group C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims 8
- 125000002393 azetidinyl group Chemical group 0.000 claims 7
- 239000003814 drug Substances 0.000 claims 7
- 238000000034 method Methods 0.000 claims 7
- 239000008194 pharmaceutical composition Substances 0.000 claims 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 229940124597 therapeutic agent Drugs 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 201000003883 Cystic fibrosis Diseases 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000006317 cyclopropyl amino group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims 2
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- NBJLTLGVBUBVLA-UHFFFAOYSA-N 1-[3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridine-2-carbonyl]azetidine-3-carbonitrile Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)C#N NBJLTLGVBUBVLA-UHFFFAOYSA-N 0.000 claims 1
- 125000006432 1-methyl cyclopropyl group Chemical group [H]C([H])([H])C1(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000006509 3,4-difluorobenzyl group Chemical group [H]C1=C(F)C(F)=C([H])C(=C1[H])C([H])([H])* 0.000 claims 1
- XILTWMLLALZONO-VIFPVBQESA-N 3-amino-5-[cyclobutyl(methyl)sulfamoyl]-N-[(2S)-2-hydroxypropyl]pyridine-2-carboxamide Chemical compound NC=1C(=NC=C(C=1)S(N(C)C1CCC1)(=O)=O)C(=O)NC[C@H](C)O XILTWMLLALZONO-VIFPVBQESA-N 0.000 claims 1
- VUECFWYLDITMCU-UHFFFAOYSA-N 3-amino-5-[cyclopropyl(2-methoxyethyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide Chemical compound NC=1C(=NC=C(C=1)S(N(CCOC)C1CC1)(=O)=O)C(=O)NCC(C(F)(F)F)O VUECFWYLDITMCU-UHFFFAOYSA-N 0.000 claims 1
- HDUZWBIERYJQSD-UHFFFAOYSA-N 3-amino-5-[cyclopropyl(methyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide Chemical compound NC=1C(=NC=C(C=1)S(N(C)C1CC1)(=O)=O)C(=O)NCC(C(F)(F)F)O HDUZWBIERYJQSD-UHFFFAOYSA-N 0.000 claims 1
- OAOQQPSJKMYVMN-UHFFFAOYSA-N 3-amino-5-[methyl(3,3,3-trifluoropropyl)sulfamoyl]-N-(3,3,3-trifluoro-2-hydroxypropyl)pyridine-2-carboxamide Chemical compound NC=1C(=NC=C(C=1)S(N(CCC(F)(F)F)C)(=O)=O)C(=O)NCC(C(F)(F)F)O OAOQQPSJKMYVMN-UHFFFAOYSA-N 0.000 claims 1
- QBAFPUXVDIHRPD-UHFFFAOYSA-N 3-amino-N'-(2-hydroxyacetyl)-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridine-2-carbohydrazide Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)NNC(CO)=O QBAFPUXVDIHRPD-UHFFFAOYSA-N 0.000 claims 1
- IQCYMBASMSUAKP-UHFFFAOYSA-N 3-amino-N'-(2-methoxyacetyl)-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridine-2-carbohydrazide Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)NNC(COC)=O IQCYMBASMSUAKP-UHFFFAOYSA-N 0.000 claims 1
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 claims 1
- 125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims 1
- LQXDPBBWNPNZCC-UHFFFAOYSA-N [3-amino-5-(3-fluorophenyl)sulfonylpyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC(=CC=C1)F)C(=O)N1CC(C1)(C(F)(F)F)O LQXDPBBWNPNZCC-UHFFFAOYSA-N 0.000 claims 1
- ZCHBGZYGDTWRDD-UHFFFAOYSA-N [3-amino-5-(4-fluorophenyl)sulfonylpyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)F)C(=O)N1CC(C1)(C(F)(F)F)O ZCHBGZYGDTWRDD-UHFFFAOYSA-N 0.000 claims 1
- XDADNLHUFALPBV-UHFFFAOYSA-N [3-amino-5-(benzenesulfonyl)pyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=CC=C1)C(=O)N1CC(C1)(C(F)(F)F)O XDADNLHUFALPBV-UHFFFAOYSA-N 0.000 claims 1
- BFJMRZZEASICIF-VIFPVBQESA-N [3-amino-5-[(2S)-2-methylpyrrolidin-1-yl]sulfonylpyridin-2-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)N1[C@H](CCC1)C)C(=O)N1CC(C1)O BFJMRZZEASICIF-VIFPVBQESA-N 0.000 claims 1
- JAOBEDWSNMFKSH-UHFFFAOYSA-N [3-amino-5-[2-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3,3-difluoroazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F)C(=O)N1CC(C1)(F)F JAOBEDWSNMFKSH-UHFFFAOYSA-N 0.000 claims 1
- LOTSMTAUTSQGJT-UHFFFAOYSA-N [3-amino-5-[2-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F)C(=O)N1CC(C1)O LOTSMTAUTSQGJT-UHFFFAOYSA-N 0.000 claims 1
- PDUMTJUIZPPPLP-UHFFFAOYSA-N [3-amino-5-[2-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=CC=C1)OC(F)(F)F)C(=O)N1CC(C1)(C(F)(F)F)O PDUMTJUIZPPPLP-UHFFFAOYSA-N 0.000 claims 1
- FVGJJRBYFJEDFO-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3,3-difluoroazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)OC(F)(F)F)F)C(=O)N1CC(C1)(F)F FVGJJRBYFJEDFO-UHFFFAOYSA-N 0.000 claims 1
- RXPRJNXJDMYOQE-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3,3-dimethylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)OC(F)(F)F)F)C(=O)N1CC(C1)(C)C RXPRJNXJDMYOQE-UHFFFAOYSA-N 0.000 claims 1
- AMFVXRKYHFEKMP-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)OC(F)(F)F)F)C(=O)N1CC(C1)O AMFVXRKYHFEKMP-UHFFFAOYSA-N 0.000 claims 1
- MQLGDXNWCIUTIH-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[3-(2-hydroxypropan-2-yl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)OC(F)(F)F)F)C(=O)N1CC(C1)C(C)(C)O MQLGDXNWCIUTIH-UHFFFAOYSA-N 0.000 claims 1
- IUNAQDRQLYAWFM-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)OC(F)(F)F)F)C(=O)N1CC(C1)(C(F)(F)F)O IUNAQDRQLYAWFM-UHFFFAOYSA-N 0.000 claims 1
- NGKHBZRNIPDQNH-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-(3,3-difluoroazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)(F)F NGKHBZRNIPDQNH-UHFFFAOYSA-N 0.000 claims 1
- LLVZTOOPOYYUGO-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-(3,3-dimethylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)(C)C LLVZTOOPOYYUGO-UHFFFAOYSA-N 0.000 claims 1
- BYKIYVPIRUWADX-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-(3-hydroxy-3-propan-2-ylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)(C(C)C)O BYKIYVPIRUWADX-UHFFFAOYSA-N 0.000 claims 1
- BBSJTDWHJSRJBP-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(2-hydroxypropan-2-yl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)C(C)(C)O BBSJTDWHJSRJBP-UHFFFAOYSA-N 0.000 claims 1
- VUNIUDWRMIUGJL-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(difluoromethoxy)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)OC(F)F VUNIUDWRMIUGJL-UHFFFAOYSA-N 0.000 claims 1
- WPAKRDQIIHLOAG-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)C(F)(F)F WPAKRDQIIHLOAG-UHFFFAOYSA-N 0.000 claims 1
- AISWTXFOFQYKIO-UHFFFAOYSA-N [3-amino-5-[2-fluoro-4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-hydroxy-3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=C(C=C(C=C1)C(F)(F)F)F)C(=O)N1CC(C1)(C(F)(F)F)O AISWTXFOFQYKIO-UHFFFAOYSA-N 0.000 claims 1
- GIQTYQUBLIRQBU-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(2-oxa-6-azaspiro[3.3]heptan-6-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC2(COC2)C1 GIQTYQUBLIRQBU-UHFFFAOYSA-N 0.000 claims 1
- QTAGZTFIFSKHRU-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3,3-difluoroazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)(F)F QTAGZTFIFSKHRU-UHFFFAOYSA-N 0.000 claims 1
- OTPCPSZQNKTJTL-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3,3-difluoropyrrolidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(CC1)(F)F OTPCPSZQNKTJTL-UHFFFAOYSA-N 0.000 claims 1
- KZKAXUGPEJBPKS-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3,3-dimethylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)(C)C KZKAXUGPEJBPKS-UHFFFAOYSA-N 0.000 claims 1
- YOSZXSLQQAARFX-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-cyclopropyl-3-hydroxyazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)(O)C1CC1 YOSZXSLQQAARFX-UHFFFAOYSA-N 0.000 claims 1
- SUKBWPIPJJKQNG-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-ethyl-3-fluoroazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)(F)CC SUKBWPIPJJKQNG-UHFFFAOYSA-N 0.000 claims 1
- YUKZQFUVNQVEKI-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-fluoroazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)F YUKZQFUVNQVEKI-UHFFFAOYSA-N 0.000 claims 1
- ZMKIJMGIYWEDHA-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-hydroxy-3-methylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)(C)O ZMKIJMGIYWEDHA-UHFFFAOYSA-N 0.000 claims 1
- HGCACXFIBVYVCN-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-hydroxyazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)O HGCACXFIBVYVCN-UHFFFAOYSA-N 0.000 claims 1
- PSPNKTCMQOEXIF-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-hydroxypyrrolidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(CC1)O PSPNKTCMQOEXIF-UHFFFAOYSA-N 0.000 claims 1
- YVHMLBFGBNPACU-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-methoxyazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)OC YVHMLBFGBNPACU-UHFFFAOYSA-N 0.000 claims 1
- NBFVNHQZCJPOFJ-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-methylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)C NBFVNHQZCJPOFJ-UHFFFAOYSA-N 0.000 claims 1
- DRAVIGYHAYWPFZ-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(3-morpholin-4-ylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)N1CCOCC1 DRAVIGYHAYWPFZ-UHFFFAOYSA-N 0.000 claims 1
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- 2016-05-25 CA CA2988046A patent/CA2988046A1/en not_active Abandoned
- 2016-05-25 PE PE2017002509A patent/PE20180457A1/es unknown
- 2016-05-25 EP EP16736610.3A patent/EP3303294A1/en not_active Withdrawn
- 2016-05-25 WO PCT/IB2016/000821 patent/WO2016193812A1/en not_active Ceased
- 2016-05-25 BR BR112017026132A patent/BR112017026132A2/pt not_active Application Discontinuation
- 2016-05-25 HK HK18112786.3A patent/HK1253581A1/zh unknown
- 2016-06-02 UY UY0001036702A patent/UY36702A/es not_active Application Discontinuation
- 2016-06-02 TW TW105117470A patent/TW201713621A/zh unknown
- 2016-06-02 AR ARP160101620A patent/AR106865A1/es unknown
-
2017
- 2017-11-30 IL IL256032A patent/IL256032A/en unknown
- 2017-12-01 PH PH12017502201A patent/PH12017502201A1/en unknown
- 2017-12-01 DO DO2017000278A patent/DOP2017000278A/es unknown
- 2017-12-01 CL CL2017003067A patent/CL2017003067A1/es unknown
- 2017-12-06 CO CONC2017/0012566A patent/CO2017012566A2/es unknown
- 2017-12-28 EC ECIEPI201785494A patent/ECSP17085494A/es unknown
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