JP2018516932A5 - - Google Patents
Download PDFInfo
- Publication number
- 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.)
- Pending
Links
- 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
- OMLFWZZCVXJEAS-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(6-oxa-2-azaspiro[3.4]octan-2-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(C1)COCC2 OMLFWZZCVXJEAS-UHFFFAOYSA-N 0.000 claims 1
- BREHFWWRDWJRNC-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(6-oxa-2-azaspiro[3.5]nonan-2-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(C1)COCCC2 BREHFWWRDWJRNC-UHFFFAOYSA-N 0.000 claims 1
- MLEPOEJQYVNKAV-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-(azetidin-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)N1CCC1 MLEPOEJQYVNKAV-UHFFFAOYSA-N 0.000 claims 1
- LFCREYLRFWPTOE-SNVBAGLBSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[(3R)-3-fluoropyrrolidin-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)N1C[C@@H](CC1)F LFCREYLRFWPTOE-SNVBAGLBSA-N 0.000 claims 1
- LFCREYLRFWPTOE-JTQLQIEISA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[(3S)-3-fluoropyrrolidin-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)N1C[C@H](CC1)F LFCREYLRFWPTOE-JTQLQIEISA-N 0.000 claims 1
- GWWGPISWQNPIJI-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[3-(2,2-difluoroethoxy)azetidin-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)OCC(F)F GWWGPISWQNPIJI-UHFFFAOYSA-N 0.000 claims 1
- YLEVYEAUZVOZQV-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[3-(hydroxymethyl)azetidin-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)CO YLEVYEAUZVOZQV-UHFFFAOYSA-N 0.000 claims 1
- BGBMACPXQQXPJV-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethoxy)phenyl]sulfonylpyridin-2-yl]-[3-(methoxymethyl)-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)COC BGBMACPXQQXPJV-UHFFFAOYSA-N 0.000 claims 1
- KEYKCCFNYGMEFM-UHFFFAOYSA-N [3-amino-5-[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=CC=C(C=C1)OC(F)(F)F)C(=O)N1CC(C1)(C(F)(F)F)O KEYKCCFNYGMEFM-UHFFFAOYSA-N 0.000 claims 1
- WBCWATHSPPPLNB-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)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)C(F)(F)F)C(=O)N1CC(C1)(F)F WBCWATHSPPPLNB-UHFFFAOYSA-N 0.000 claims 1
- UQCFKZCSEZNSKV-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)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)C(F)(F)F)C(=O)N1CC(C1)(C)C UQCFKZCSEZNSKV-UHFFFAOYSA-N 0.000 claims 1
- QRVMQTQRRNVTEF-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-(3-fluoro-3-methylazetidin-1-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)(C)F QRVMQTQRRNVTEF-UHFFFAOYSA-N 0.000 claims 1
- TVHYQDKUQSGJFP-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)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)C(F)(F)F)C(=O)N1CC(C1)(C)O TVHYQDKUQSGJFP-UHFFFAOYSA-N 0.000 claims 1
- QCJRMXDXVFLRTJ-UHFFFAOYSA-N [3-amino-5-[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=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)(C(C)C)O QCJRMXDXVFLRTJ-UHFFFAOYSA-N 0.000 claims 1
- QKYWQNIMWJUHQD-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-(6-oxa-2-azaspiro[3.5]nonan-2-yl)methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1CC2(C1)COCCC2 QKYWQNIMWJUHQD-UHFFFAOYSA-N 0.000 claims 1
- WRISKWZHYBNCLJ-GFCCVEGCSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1[C@H](CCC1)CO WRISKWZHYBNCLJ-GFCCVEGCSA-N 0.000 claims 1
- WRISKWZHYBNCLJ-LBPRGKRZSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1[C@@H](CCC1)CO WRISKWZHYBNCLJ-LBPRGKRZSA-N 0.000 claims 1
- ZZUDCPFQNOBDHK-ZIAGYGMSSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[(3R,4R)-3,4-dihydroxypyrrolidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1C[C@H]([C@@H](C1)O)O ZZUDCPFQNOBDHK-ZIAGYGMSSA-N 0.000 claims 1
- MEYNAHUAJYTGII-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(2,2-difluoroethoxy)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)OCC(F)F MEYNAHUAJYTGII-UHFFFAOYSA-N 0.000 claims 1
- XETMAANFOXSVDX-UHFFFAOYSA-N [3-amino-5-[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=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)C(C)(C)O XETMAANFOXSVDX-UHFFFAOYSA-N 0.000 claims 1
- PDQJUEPYBASBNF-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(difluoromethoxy)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)OC(F)F PDQJUEPYBASBNF-UHFFFAOYSA-N 0.000 claims 1
- SWRLQASNXOZKIM-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(methoxymethyl)-3-methylazetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)(C)COC SWRLQASNXOZKIM-UHFFFAOYSA-N 0.000 claims 1
- NJADIFQWGCQIFR-UHFFFAOYSA-N [3-amino-5-[4-(trifluoromethyl)phenyl]sulfonylpyridin-2-yl]-[3-(trifluoromethyl)azetidin-1-yl]methanone Chemical compound NC=1C(=NC=C(C=1)S(=O)(=O)C1=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)C(F)(F)F NJADIFQWGCQIFR-UHFFFAOYSA-N 0.000 claims 1
- YOJMXLZULJYADS-UHFFFAOYSA-N [3-amino-5-[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=CC=C(C=C1)C(F)(F)F)C(=O)N1CC(C1)(C(F)(F)F)O YOJMXLZULJYADS-UHFFFAOYSA-N 0.000 claims 1
- VEQOALNAAJBPNY-UHFFFAOYSA-N antipyrine Chemical class CN1C(C)=CC(=O)N1C1=CC=CC=C1 VEQOALNAAJBPNY-UHFFFAOYSA-N 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 125000002912 morpholin-4-ylsulfonyl group Chemical group O1C([H])([H])C([H])([H])N(S(=O)(=O)[*])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 238000006386 neutralization reaction Methods 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 125000006299 oxetan-3-yl group Chemical group [H]C1([H])OC([H])([H])C1([H])* 0.000 claims 1
- 125000003566 oxetanyl group Chemical group 0.000 claims 1
- 229960005222 phenazone Drugs 0.000 claims 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562169881P | 2015-06-02 | 2015-06-02 | |
| US62/169,881 | 2015-06-02 | ||
| PCT/IB2016/000821 WO2016193812A1 (en) | 2015-06-02 | 2016-05-25 | Substituted pyridines and method of use |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018516932A JP2018516932A (ja) | 2018-06-28 |
| JP2018516932A5 true JP2018516932A5 (cg-RX-API-DMAC7.html) | 2019-06-27 |
Family
ID=57440295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017562678A Pending JP2018516932A (ja) | 2015-06-02 | 2016-05-25 | 置換ピリジンおよび使用方法 |
Country Status (23)
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20210401869A1 (en) * | 2015-02-20 | 2021-12-30 | Rosalind Franklin University Of Medicine And Science | Antisense Compounds Targeting Genes Associated with Cystic Fibrosis |
| US10138227B2 (en) * | 2016-06-03 | 2018-11-27 | Abbvie S.Á.R.L. | Heteroaryl substituted pyridines and methods of use |
| TW201811766A (zh) | 2016-08-29 | 2018-04-01 | 瑞士商諾華公司 | N-(吡啶-2-基)吡啶-磺醯胺衍生物及其用於疾病治療之用途 |
| US10399940B2 (en) | 2016-10-07 | 2019-09-03 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| US9981910B2 (en) | 2016-10-07 | 2018-05-29 | Abbvie S.Á.R.L. | Substituted pyrrolidines and methods of use |
| EP3558982A1 (en) | 2016-12-20 | 2019-10-30 | AbbVie S.À.R.L. | Deuterated cftr modulators and methods of use |
| TW201831471A (zh) | 2017-02-24 | 2018-09-01 | 盧森堡商艾伯維公司 | 囊腫纖化症跨膜傳導調節蛋白的調節劑及其使用方法 |
| US10988454B2 (en) | 2017-09-14 | 2021-04-27 | Abbvie Overseas S.À.R.L. | Modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| WO2019193062A1 (en) | 2018-04-03 | 2019-10-10 | Abbvie S.Á.R.L | Substituted pyrrolidines and their use |
| US20220127247A1 (en) * | 2019-02-06 | 2022-04-28 | Novartis Ag | N-(pyridin-2-yl)pyridine-sulfonamide derivatives and their use in the treatment of disease |
| EP3747882A1 (en) | 2019-06-03 | 2020-12-09 | AbbVie Overseas S.à r.l. | Prodrug modulators of the cystic fibrosis transmembrane conductance regulator protein and methods of use |
| TW202115014A (zh) | 2019-07-12 | 2021-04-16 | 美商奧佛麥德公司 | 用於治療囊腫纖維化之化合物 |
| US20220211692A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| US20220213041A1 (en) | 2021-01-06 | 2022-07-07 | AbbVie Global Enterprises Ltd. | Modulators of the Cystic Fibrosis Transmembrane Conductance Regulator Protein and Methods of Use |
| EP4387449A1 (en) | 2021-08-19 | 2024-06-26 | Syngenta Crop Protection AG | Method for controlling diamide resistant pests & compounds therefor |
| WO2023034946A1 (en) * | 2021-09-03 | 2023-03-09 | Genzyme Corporation | Indole compounds and uses thereof in the treatement of cystic fibrosis |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7939558B2 (en) | 2004-06-04 | 2011-05-10 | The Regents Of The University Of California | Compounds having activity in increasing ion transport by mutant-CFTR and uses thereof |
| US8354427B2 (en) | 2004-06-24 | 2013-01-15 | Vertex Pharmaceutical Incorporated | Modulators of ATP-binding cassette transporters |
| ME02799B (me) | 2004-06-24 | 2018-01-20 | Vertex Pharma | Modulatori ATP-vezujućih kasetnih transportera |
| NZ581419A (en) | 2007-05-25 | 2012-05-25 | Vertex Pharma | Modulators of cystic fibrosis transmembrane conductance regulator |
| NZ585789A (en) | 2007-12-10 | 2012-03-30 | Novartis Ag | Pyrazine-2-carboxamide derivatives to treat diseases mediated by blockade of the epithelial sodium channel |
| ES2422741T3 (es) | 2007-12-13 | 2013-09-13 | Vertex Pharma | Moduladores del regulador de la conductancia transmembrana de la fibrosis quística |
| US8436014B2 (en) | 2008-10-23 | 2013-05-07 | Vertex Pharmaceutical Incorporated | Solid forms of N-(4-(7-azabicyclo[2.2.1]heptan-7-yl)-2-(trifluorormethyl)phenyl)-4-oxo-5-(trifluoromethyl)-1,4-dihyroquinoline-3-carboxamide |
| JP5699090B2 (ja) | 2008-12-30 | 2015-04-08 | バーテックス ファーマシューティカルズ インコーポレイテッドＶｅｒｔｅｘ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | 嚢胞性線維症膜コンダクタンス調節因子のモジュレーター |
| US8247436B2 (en) * | 2010-03-19 | 2012-08-21 | Novartis Ag | Pyridine and pyrazine derivative for the treatment of CF |
| US9034879B2 (en) | 2011-09-16 | 2015-05-19 | Novartis Ag | Heterocyclic compounds for the treatment of CF |
| ES2882807T3 (es) | 2011-09-16 | 2021-12-02 | Novartis Ag | Heterociclil carboxamidas N-sustituidas |
| WO2013038378A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038373A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine amide derivatives |
| WO2013038381A1 (en) | 2011-09-16 | 2013-03-21 | Novartis Ag | Pyridine/pyrazine amide derivatives |
| EP2760463B1 (en) | 2011-09-20 | 2018-11-21 | The University of North Carolina At Chapel Hill | Regulation of sodium channels by plunc proteins |
| US9382254B2 (en) * | 2013-05-07 | 2016-07-05 | Galapagos Nv | Compounds and pharmaceutical compositions thereof for the treatment of cystic fibrosis |
| ES2691944T3 (es) | 2013-08-08 | 2018-11-29 | Galapagos Nv | Tieno[2,3-c]piranos como moduladores CFTR |
| CA2942387A1 (en) | 2014-03-13 | 2015-09-17 | Proteostasis Therapeutics, Inc. | Compounds, compositions and methods of increasing cftr actvity |
| EP3116501A1 (en) | 2014-03-13 | 2017-01-18 | Proteostasis Therapeutics, Inc. | Compounds, compositions, and methods for increasing cftr activity |
| WO2017196843A1 (en) * | 2016-05-09 | 2017-11-16 | Proteostasis Therapeutics, Inc. | Methods of identifying cftr modulators |
-
2016
- 2016-05-25 RU RU2017146661A patent/RU2017146661A/ru not_active Application Discontinuation
- 2016-05-25 CR CR20170595A patent/CR20170595A/es unknown
- 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 JP JP2017562678A patent/JP2018516932A/ja active Pending
- 2016-05-25 AU AU2016272702A patent/AU2016272702A1/en not_active Abandoned
- 2016-05-25 CA CA2988046A patent/CA2988046A1/en not_active Abandoned
- 2016-05-25 KR KR1020177037457A patent/KR20180029204A/ko not_active Withdrawn
- 2016-05-25 HK HK18112786.3A patent/HK1253581A1/zh unknown
- 2016-05-25 MX MX2017015591A patent/MX2017015591A/es unknown
- 2016-05-25 US US15/164,317 patent/US10047051B2/en active Active
- 2016-05-25 CN CN201680043914.3A patent/CN107922338A/zh active Pending
- 2016-05-25 BR BR112017026132A patent/BR112017026132A2/pt not_active Application Discontinuation
- 2016-06-02 TW TW105117470A patent/TW201713621A/zh unknown
- 2016-06-02 UY UY0001036702A patent/UY36702A/es not_active Application Discontinuation
- 2016-06-02 AR ARP160101620A patent/AR106865A1/es unknown
-
2017
- 2017-11-30 IL IL256032A patent/IL256032A/en unknown
- 2017-12-01 DO DO2017000278A patent/DOP2017000278A/es unknown
- 2017-12-01 CL CL2017003067A patent/CL2017003067A1/es unknown
- 2017-12-01 PH PH12017502201A patent/PH12017502201A1/en unknown
- 2017-12-06 CO CONC2017/0012566A patent/CO2017012566A2/es unknown
- 2017-12-28 EC ECIEPI201785494A patent/ECSP17085494A/es unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2018516932A5 (cg-RX-API-DMAC7.html) | ||
| RU2017146661A (ru) | Замещенные пиридины и способ их применения | |
| RU2015143917A (ru) | Индуцирующие апоптоз средства для лечения злокачественной опухоли и иммунологических и аутоиммунных заболеваний | |
| JP2014521696A5 (cg-RX-API-DMAC7.html) | ||
| JP2017530999A5 (cg-RX-API-DMAC7.html) | ||
| RU2011127402A (ru) | Селективные к bcl-2 агенты, вызывающие апоптоз, для лечения рака и иммунных заболеваний | |
| CN1902196B (zh) | 噻唑衍生物 | |
| RU2017116598A (ru) | Соединения и композиции для модуляции киназной активности мутантов egfr | |
| JP5518838B2 (ja) | ピロリジノングルコキナーゼアクチベーター | |
| RU2347777C2 (ru) | Двойные агонисты nk1/nk3 для лечения шизофрении | |
| JP2015529192A5 (cg-RX-API-DMAC7.html) | ||
| AU2014291711B2 (en) | Autotaxin inhibitors comprising a heteroaromatic ring-benzyl-amide-cycle core | |
| JP2018524343A5 (cg-RX-API-DMAC7.html) | ||
| JP2005523901A5 (cg-RX-API-DMAC7.html) | ||
| RU2011127232A (ru) | Апоптоз-индуцирующие средства для лечения рака и иммунных и аутоиммунных заболеваний | |
| HRP20230294T1 (hr) | Modulatori tmem16a | |
| RU2001126337A (ru) | Соединения, пригодные в качестве противовоспалительных агентов | |
| JP2012532888A5 (cg-RX-API-DMAC7.html) | ||
| JP6074043B2 (ja) | 新規なモルホリン誘導体またはその塩 | |
| HRP20240297T1 (hr) | Derivati alfa-d-galaktopiranozida | |
| CN109923113A (zh) | 作为GABA A α5 PAM的新型异噁唑基醚衍生物 | |
| JP2018512408A5 (cg-RX-API-DMAC7.html) | ||
| JP2018505145A5 (cg-RX-API-DMAC7.html) | ||
| JPWO2021081375A5 (cg-RX-API-DMAC7.html) | ||
| JP2017512806A5 (cg-RX-API-DMAC7.html) |