JP2014532660A5 - - Google Patents
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- JP2014532660A5 JP2014532660A5 JP2014539066A JP2014539066A JP2014532660A5 JP 2014532660 A5 JP2014532660 A5 JP 2014532660A5 JP 2014539066 A JP2014539066 A JP 2014539066A JP 2014539066 A JP2014539066 A JP 2014539066A JP 2014532660 A5 JP2014532660 A5 JP 2014532660A5
- Authority
- JP
- Japan
- Prior art keywords
- oxo
- sulfonamide
- dihydro
- benzoxazole
- thiadiazol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 aralkenyl Chemical group 0.000 claims 44
- 125000000217 alkyl group Chemical group 0.000 claims 39
- 229910052736 halogen Inorganic materials 0.000 claims 36
- 229910052799 carbon Inorganic materials 0.000 claims 33
- 150000002367 halogens Chemical class 0.000 claims 31
- 125000003118 aryl group Chemical group 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 22
- 125000004432 carbon atom Chemical group C* 0.000 claims 20
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 19
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 150000003839 salts Chemical class 0.000 claims 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 13
- 125000005843 halogen group Chemical group 0.000 claims 10
- 125000000623 heterocyclic group Chemical group 0.000 claims 10
- 125000004429 atom Chemical group 0.000 claims 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims 7
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 229940124530 sulfonamide Drugs 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000003386 piperidinyl group Chemical group 0.000 claims 5
- 125000006413 ring segment Chemical group 0.000 claims 5
- 229910052717 sulfur Inorganic materials 0.000 claims 5
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 5
- IEYWAMQEEJSGKK-UHFFFAOYSA-N 4-(thiadiazol-5-yl)-2,3-dihydro-1,3-benzoxazole-6-sulfonamide Chemical compound NS(=O)(=O)C1=CC2=C(NCO2)C(=C1)C1=CN=NS1 IEYWAMQEEJSGKK-UHFFFAOYSA-N 0.000 claims 4
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 125000005110 aryl thio group Chemical group 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 150000001408 amides Chemical class 0.000 claims 3
- 125000004122 cyclic group Chemical group 0.000 claims 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 3
- 229910052757 nitrogen Inorganic materials 0.000 claims 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 3
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims 2
- 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims 2
- ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical group C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 claims 2
- VVZRKTDMSUWVGR-UHFFFAOYSA-N 2-oxo-3-(1-phenylbut-3-enyl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=C(S(=O)(=O)NC=3SN=CN=3)C=C2OC(=O)N1C(CC=C)C1=CC=CC=C1 VVZRKTDMSUWVGR-UHFFFAOYSA-N 0.000 claims 2
- WPLZOHYVBARFAX-GFCCVEGCSA-N 2-oxo-3-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C=4CNCCC=4C=CC=3)C)C2=CC=C1S(=O)(=O)NC1=NC=NS1 WPLZOHYVBARFAX-GFCCVEGCSA-N 0.000 claims 2
- UWQNWXMVIFOIBT-LLVKDONJSA-N 2-oxo-3-[(1r)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=CC=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 UWQNWXMVIFOIBT-LLVKDONJSA-N 0.000 claims 2
- VGNXPEYAJVASMT-GFCCVEGCSA-N 2-oxo-3-[(1r)-1-phenylethyl]-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=CC=C32)S(=O)(=O)NC=2SC=CN=2)=O)=CC=CC=C1 VGNXPEYAJVASMT-GFCCVEGCSA-N 0.000 claims 2
- WPLZOHYVBARFAX-LBPRGKRZSA-N 2-oxo-3-[(1s)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@H](C=3C=4CNCCC=4C=CC=3)C)C2=CC=C1S(=O)(=O)NC1=NC=NS1 WPLZOHYVBARFAX-LBPRGKRZSA-N 0.000 claims 2
- WPLZOHYVBARFAX-UHFFFAOYSA-N 2-oxo-3-[1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=1C=CC=2CCNCC=2C=1C(C)N(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 WPLZOHYVBARFAX-UHFFFAOYSA-N 0.000 claims 2
- OHJAPQBBNJRKMD-UHFFFAOYSA-N 2-oxo-3-[[2-(1,2,3,4-tetrahydroisoquinolin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C(=CC=CC=3)C=3C=4CCNCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 OHJAPQBBNJRKMD-UHFFFAOYSA-N 0.000 claims 2
- UXVIUHVJUPVTMN-UHFFFAOYSA-N 2-oxo-3-[[2-(1,2,3,4-tetrahydroisoquinolin-8-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C(=CC=CC=3)C=3C=4CNCCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 UXVIUHVJUPVTMN-UHFFFAOYSA-N 0.000 claims 2
- XJLAMYIBBITSHV-UHFFFAOYSA-N 2-oxo-3-[[2-(1,2,3,6-tetrahydropyridin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC1=CC=CC=C1C1=CCCNC1 XJLAMYIBBITSHV-UHFFFAOYSA-N 0.000 claims 2
- PKXAFOREXLJQNP-UHFFFAOYSA-N 2-oxo-3-[[2-(2,3,4,7-tetrahydro-1h-azepin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC1=CC=CC=C1C1=CCNCCC1 PKXAFOREXLJQNP-UHFFFAOYSA-N 0.000 claims 2
- ONCZUYMMTAZQKX-UHFFFAOYSA-N 2-oxo-3-[[3-(1,2,3,4-tetrahydroisoquinolin-7-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C=C(C=CC=3)C=3C=C4CNCCC4=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 ONCZUYMMTAZQKX-UHFFFAOYSA-N 0.000 claims 2
- FQYYAUZQOQGLCE-UHFFFAOYSA-N 3-(5-amino-1,2,3,4-tetrahydronaphthalen-1-yl)-5-fluoro-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1CCC=2C(N)=CC=CC=2C1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 FQYYAUZQOQGLCE-UHFFFAOYSA-N 0.000 claims 2
- BIMVOEJQXOIUNX-UHFFFAOYSA-N 3-(7-amino-1,2,3,4-tetrahydronaphthalen-1-yl)-5-fluoro-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC(N)=CC=C2CCCC1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 BIMVOEJQXOIUNX-UHFFFAOYSA-N 0.000 claims 2
- VWVWAROPVVMIFI-UHFFFAOYSA-N 3-[(2-methylsulfonyl-3,4-dihydro-1h-isoquinolin-8-yl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=12CN(S(=O)(=O)C)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 VWVWAROPVVMIFI-UHFFFAOYSA-N 0.000 claims 2
- UQWWTYOVGCIIMC-UHFFFAOYSA-N 3-[[2-(8-azabicyclo[3.2.1]oct-3-en-3-yl)phenyl]methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C(=CC=CC=3)C=3CC4CCC(N4)C=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 UQWWTYOVGCIIMC-UHFFFAOYSA-N 0.000 claims 2
- ALANPISCNIRVFD-UHFFFAOYSA-N 3-[[2-(aminomethyl)phenyl]methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound NCC1=CC=CC=C1CN1C(=O)OC2=CC(S(=O)(=O)NC=3SN=CN=3)=CC=C21 ALANPISCNIRVFD-UHFFFAOYSA-N 0.000 claims 2
- HRHKZBCREGDXFE-ZZXKWVIFSA-N 3-[[2-[(e)-3-aminoprop-1-enyl]phenyl]methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound NC\C=C\C1=CC=CC=C1CN1C(=O)OC2=CC(S(=O)(=O)NC=3SN=CN=3)=C(F)C=C21 HRHKZBCREGDXFE-ZZXKWVIFSA-N 0.000 claims 2
- GOBMSLUGEQXILA-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1C(C=1C=CC=CC=1)C1CC1 GOBMSLUGEQXILA-UHFFFAOYSA-N 0.000 claims 2
- MYWZAJHQYKKYCH-UHFFFAOYSA-N 3-benzyl-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC1=CC=CC=C1 MYWZAJHQYKKYCH-UHFFFAOYSA-N 0.000 claims 2
- GUSOQWBTWYLMLQ-UHFFFAOYSA-N 5-fluoro-2-oxo-3-(1,2,3,4-tetrahydroisoquinolin-8-ylmethyl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound FC1=CC=2N(CC=3C=4CNCCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 GUSOQWBTWYLMLQ-UHFFFAOYSA-N 0.000 claims 2
- GHWQAMFFIFODIK-LLVKDONJSA-N 5-fluoro-2-oxo-3-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C=4CNCCC=4C=CC=3)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=NS1 GHWQAMFFIFODIK-LLVKDONJSA-N 0.000 claims 2
- SSRICSLNCPEIOS-SNVBAGLBSA-N 5-fluoro-2-oxo-3-[(1r)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 SSRICSLNCPEIOS-SNVBAGLBSA-N 0.000 claims 2
- RODAEAZPMFDVON-LLVKDONJSA-N 5-fluoro-2-oxo-3-[(1r)-1-phenylethyl]-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SC=CN=2)=O)=CC=CC=C1 RODAEAZPMFDVON-LLVKDONJSA-N 0.000 claims 2
- GHWQAMFFIFODIK-NSHDSACASA-N 5-fluoro-2-oxo-3-[(1s)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@H](C=3C=4CNCCC=4C=CC=3)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=NS1 GHWQAMFFIFODIK-NSHDSACASA-N 0.000 claims 2
- AIQVKWJGIQNCLH-LLVKDONJSA-N 5-fluoro-3-[(1r)-1-[2-(3-hydroxyazetidin-3-yl)phenyl]ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1(O)CNC1 AIQVKWJGIQNCLH-LLVKDONJSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 2
- 125000002252 acyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000003435 aroyl group Chemical group 0.000 claims 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims 2
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims 2
- 125000005135 aryl sulfinyl group Chemical group 0.000 claims 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims 2
- 125000004104 aryloxy group Chemical group 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 2
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 2
- 208000004296 neuralgia Diseases 0.000 claims 2
- 208000021722 neuropathic pain Diseases 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 2
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims 2
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 1
- MKUSHAQSNWAEBN-UHFFFAOYSA-N 2-oxo-3-(1,2,3,4-tetrahydroisoquinolin-5-ylmethyl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C=4CCNCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 MKUSHAQSNWAEBN-UHFFFAOYSA-N 0.000 claims 1
- UWQNWXMVIFOIBT-UHFFFAOYSA-N 2-oxo-3-(1-phenylethyl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=C(S(=O)(=O)NC=3SN=CN=3)C=C2OC(=O)N1C(C)C1=CC=CC=C1 UWQNWXMVIFOIBT-UHFFFAOYSA-N 0.000 claims 1
- VGNXPEYAJVASMT-UHFFFAOYSA-N 2-oxo-3-(1-phenylethyl)-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=C(S(=O)(=O)NC=3SC=CN=3)C=C2OC(=O)N1C(C)C1=CC=CC=C1 VGNXPEYAJVASMT-UHFFFAOYSA-N 0.000 claims 1
- SOPCEYMWSZYBKO-UHFFFAOYSA-N 2-oxo-3-(1-phenylpropyl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=C(S(=O)(=O)NC=3SN=CN=3)C=C2OC(=O)N1C(CC)C1=CC=CC=C1 SOPCEYMWSZYBKO-UHFFFAOYSA-N 0.000 claims 1
- BBQDKTQFGDVNAX-UHFFFAOYSA-N 2-oxo-3-(4-phenylbutan-2-yl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=C(S(=O)(=O)NC=3SN=CN=3)C=C2OC(=O)N1C(C)CCC1=CC=CC=C1 BBQDKTQFGDVNAX-UHFFFAOYSA-N 0.000 claims 1
- UWQNWXMVIFOIBT-NSHDSACASA-N 2-oxo-3-[(1s)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@H](C)N2C(OC3=CC(=CC=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 UWQNWXMVIFOIBT-NSHDSACASA-N 0.000 claims 1
- RYHCXCSIDGYDPI-UHFFFAOYSA-N 2-oxo-3-[(2-propyl-3,4-dihydro-1h-isoquinolin-8-yl)methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=12CN(CCC)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 RYHCXCSIDGYDPI-UHFFFAOYSA-N 0.000 claims 1
- XBGGWKKJVBAMOU-UHFFFAOYSA-N 2-oxo-3-[[2-(2-piperazin-1-ylphenyl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC1=CC=CC=C1C1=CC=CC=C1N1CCNCC1 XBGGWKKJVBAMOU-UHFFFAOYSA-N 0.000 claims 1
- MOJUSORLFLPWEN-UHFFFAOYSA-N 2-oxo-3-[[2-[2-(piperidin-1-ylmethyl)pyridin-4-yl]phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC1=CC=CC=C1C(C=1)=CC=NC=1CN1CCCCC1 MOJUSORLFLPWEN-UHFFFAOYSA-N 0.000 claims 1
- ZOSRSZBULXDBGN-UHFFFAOYSA-N 2-oxo-3-[[3-(1,2,3,4-tetrahydroisoquinolin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C=C(C=CC=3)C=3C=4CCNCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 ZOSRSZBULXDBGN-UHFFFAOYSA-N 0.000 claims 1
- XRHGVAVPKZTFSD-UHFFFAOYSA-N 2-oxo-3-[[3-(1,2,3,4-tetrahydroisoquinolin-8-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C=C(C=CC=3)C=3C=4CNCCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 XRHGVAVPKZTFSD-UHFFFAOYSA-N 0.000 claims 1
- CNZYIRLNDXCOOF-UHFFFAOYSA-N 2-oxo-3-[[3-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC(C=1)=CC=CC=1C1=CCNCC1 CNZYIRLNDXCOOF-UHFFFAOYSA-N 0.000 claims 1
- LIPQLZTUJJIZNF-UHFFFAOYSA-N 2-oxo-3-[[3-(1,2,3,6-tetrahydropyridin-5-yl)phenyl]methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC(C=1)=CC=CC=1C1=CCCNC1 LIPQLZTUJJIZNF-UHFFFAOYSA-N 0.000 claims 1
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- QNPDAUKAAIHDGF-ZZXKWVIFSA-N 3-[[2-[(e)-3-aminoprop-1-enyl]phenyl]methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound NC\C=C\C1=CC=CC=C1CN1C(=O)OC2=CC(S(=O)(=O)NC=3SN=CN=3)=CC=C21 QNPDAUKAAIHDGF-ZZXKWVIFSA-N 0.000 claims 1
- AAVOBVLYBAODJE-UHFFFAOYSA-N 3-[[3-(8-azabicyclo[3.2.1]oct-3-en-3-yl)phenyl]methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C=C(C=CC=3)C=3CC4CCC(N4)C=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 AAVOBVLYBAODJE-UHFFFAOYSA-N 0.000 claims 1
- PAEJBCJKJNXOEG-UHFFFAOYSA-N 3-[[7-(3,3-difluoroazetidin-1-yl)-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide;hydrochloride Chemical compound Cl.O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC(C=1C2)=CC=CC=1CCC2N1CC(F)(F)C1 PAEJBCJKJNXOEG-UHFFFAOYSA-N 0.000 claims 1
- PSIPRNWCGIUIOK-UHFFFAOYSA-N 3-[cyclopropyl(phenyl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1C(C=1C=CC=CC=1)C1CC1 PSIPRNWCGIUIOK-UHFFFAOYSA-N 0.000 claims 1
- OZXXFTCTSNMOGT-UHFFFAOYSA-N 3-benzhydryl-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1C(C=1C=CC=CC=1)C1=CC=CC=C1 OZXXFTCTSNMOGT-UHFFFAOYSA-N 0.000 claims 1
- HMJMQGPOPAKICS-UHFFFAOYSA-N 3-benzyl-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C=CC=2N1CC1=CC=CC=C1 HMJMQGPOPAKICS-UHFFFAOYSA-N 0.000 claims 1
- OCAQLUWWNZIYHI-CYBMUJFWSA-N 5-(2-methylpyrazol-3-yl)-2-oxo-3-[(1r)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(C=4N(N=CC=4)C)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 OCAQLUWWNZIYHI-CYBMUJFWSA-N 0.000 claims 1
- OSOXNNWCUNIVCU-LLVKDONJSA-N 5-bromo-2-oxo-3-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C=4CNCCC=4C=CC=3)C)C2=CC(Br)=C1S(=O)(=O)NC1=NC=NS1 OSOXNNWCUNIVCU-LLVKDONJSA-N 0.000 claims 1
- SHJDCINHZVHSDL-CYBMUJFWSA-N 5-bromo-3-[(1r)-1-[2-[3-(methanesulfonamido)prop-1-ynyl]phenyl]ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(Br)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C#CCNS(C)(=O)=O SHJDCINHZVHSDL-CYBMUJFWSA-N 0.000 claims 1
- ZZFYQJNNDLEBNT-BTQNPOSSSA-N 5-chloro-2-oxo-3-[(1r)-1-[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide;hydrochloride Chemical compound Cl.C1([C@@H](C)N2C(OC3=CC(=C(Cl)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1=CCNCC1 ZZFYQJNNDLEBNT-BTQNPOSSSA-N 0.000 claims 1
- MCFAXCBNXAUNMR-CQSZACIVSA-N 5-chloro-3-[(1R)-1-[2-(1-methylsulfonyl-3,6-dihydro-2H-pyridin-4-yl)phenyl]ethyl]-2-oxo-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(Cl)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1=CCN(S(C)(=O)=O)CC1 MCFAXCBNXAUNMR-CQSZACIVSA-N 0.000 claims 1
- NFKDLPYBACBUKO-GFCCVEGCSA-N 5-ethyl-2-oxo-3-[(1R)-1-phenylethyl]-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C=3C=C(C(=CC=3OC2=O)S(=O)(=O)NC=2SN=CN=2)CC)=CC=CC=C1 NFKDLPYBACBUKO-GFCCVEGCSA-N 0.000 claims 1
- SKSPHKZMYWRQKV-UHFFFAOYSA-N 5-fluoro-2-oxo-3-(1,2,3,4-tetrahydronaphthalen-1-yl)-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound FC1=CC=2N(C3C4=CC=CC=C4CCC3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 SKSPHKZMYWRQKV-UHFFFAOYSA-N 0.000 claims 1
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- LHQIMCCHVSLSLB-UHFFFAOYSA-N 5-fluoro-2-oxo-3-(5,6,7,8-tetrahydroquinolin-8-yl)-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound FC1=CC=2N(C3C4=NC=CC=C4CCC3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=CS1 LHQIMCCHVSLSLB-UHFFFAOYSA-N 0.000 claims 1
- RNYRPBVZEUWHJE-LDCVWXEPSA-N 5-fluoro-2-oxo-3-[(1R)-1-[2-(2-piperidin-2-ylethynyl)phenyl]ethyl]-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C#CC1CCCCN1 RNYRPBVZEUWHJE-LDCVWXEPSA-N 0.000 claims 1
- GHVGAZZDCCWCAT-GICMACPYSA-N 5-fluoro-2-oxo-3-[(1R)-1-[2-(2-pyrrolidin-3-ylethynyl)phenyl]ethyl]-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C#CC1CCNC1 GHVGAZZDCCWCAT-GICMACPYSA-N 0.000 claims 1
- VJJBPUMOVGUJEG-GDBMZVCRSA-N 5-fluoro-2-oxo-3-[(1R)-1-[2-[2-[(2R)-pyrrolidin-2-yl]ethynyl]phenyl]ethyl]-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C[C@H](c1ccccc1C#C[C@H]1CCCN1)n1c2cc(F)c(cc2oc1=O)S(=O)(=O)Nc1ncns1 VJJBPUMOVGUJEG-GDBMZVCRSA-N 0.000 claims 1
- XWQWXQVTZBSHEL-GFCCVEGCSA-N 5-fluoro-2-oxo-3-[(1r)-1-(1,2,3,4-tetrahydroisoquinolin-8-yl)ethyl]-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C=4CNCCC=4C=CC=3)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=CS1 XWQWXQVTZBSHEL-GFCCVEGCSA-N 0.000 claims 1
- BTTIZPISHYKREM-CYBMUJFWSA-N 5-fluoro-2-oxo-3-[(1r)-1-[2-(1,2,3,6-tetrahydropyridin-4-yl)phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1=CCNCC1 BTTIZPISHYKREM-CYBMUJFWSA-N 0.000 claims 1
- JDDWJFFCJKCHRS-CYBMUJFWSA-N 5-fluoro-2-oxo-3-[(1r)-1-[2-(1,2,3,6-tetrahydropyridin-5-yl)phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1=CCCNC1 JDDWJFFCJKCHRS-CYBMUJFWSA-N 0.000 claims 1
- VPXSDHXHCCPXJW-CQSZACIVSA-N 5-fluoro-2-oxo-3-[(1r)-1-[2-(2,3,4,7-tetrahydro-1h-azepin-5-yl)phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1=CCNCCC1 VPXSDHXHCCPXJW-CQSZACIVSA-N 0.000 claims 1
- FSYUSIGCCVFSDE-CQSZACIVSA-N 5-fluoro-2-oxo-3-[(1r)-1-[2-(pyrrolidin-1-ylmethyl)phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1CN1CCCC1 FSYUSIGCCVFSDE-CQSZACIVSA-N 0.000 claims 1
- VJJBPUMOVGUJEG-ZBFHGGJFSA-N 5-fluoro-2-oxo-3-[(1r)-1-[2-[2-[(2s)-pyrrolidin-2-yl]ethynyl]phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C#C[C@@H]1CCCN1 VJJBPUMOVGUJEG-ZBFHGGJFSA-N 0.000 claims 1
- KVIVBZSSPGMSHS-GFCCVEGCSA-N 5-fluoro-2-oxo-3-[(1r)-1-[3-(6-oxo-1h-pyridin-3-yl)phenyl]ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=1C([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=1C1=CC=C(O)N=C1 KVIVBZSSPGMSHS-GFCCVEGCSA-N 0.000 claims 1
- SSRICSLNCPEIOS-JTQLQIEISA-N 5-fluoro-2-oxo-3-[(1s)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 SSRICSLNCPEIOS-JTQLQIEISA-N 0.000 claims 1
- RAFYTIQRGHHECR-UHFFFAOYSA-N 5-fluoro-2-oxo-3-[(2-phenylcyclopropyl)methyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC1CC1C1=CC=CC=C1 RAFYTIQRGHHECR-UHFFFAOYSA-N 0.000 claims 1
- NNMGXZZWAYOZPY-XLIONFOSSA-N 5-fluoro-2-oxo-3-[(2s,4r)-2-phenyl-3,4-dihydro-2h-chromen-4-yl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H]2C[C@H](C3=CC=CC=C3O2)N2C=3C=C(C(=CC=3OC2=O)S(=O)(=O)NC=2SN=CN=2)F)=CC=CC=C1 NNMGXZZWAYOZPY-XLIONFOSSA-N 0.000 claims 1
- JAWHYYIOUNLPAI-HNNXBMFYSA-N 5-fluoro-2-oxo-3-[(4S)-spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C([C@@H](C1=CC=CC=C1O1)N2C=3C=C(C(=CC=3OC2=O)S(=O)(=O)NC=2SN=CN=2)F)C21CCC2 JAWHYYIOUNLPAI-HNNXBMFYSA-N 0.000 claims 1
- JAWHYYIOUNLPAI-OAHLLOKOSA-N 5-fluoro-2-oxo-3-[(4r)-spiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C([C@H](C1=CC=CC=C1O1)N2C=3C=C(C(=CC=3OC2=O)S(=O)(=O)NC=2SN=CN=2)F)C21CCC2 JAWHYYIOUNLPAI-OAHLLOKOSA-N 0.000 claims 1
- JHBQDLGMAVWFHQ-UHFFFAOYSA-N 5-fluoro-2-oxo-3-[1-(3-pyridin-3-ylphenyl)ethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC(F)=C(S(=O)(=O)NC=3SN=CN=3)C=C2OC(=O)N1C(C)C(C=1)=CC=CC=1C1=CC=CN=C1 JHBQDLGMAVWFHQ-UHFFFAOYSA-N 0.000 claims 1
- RAFYTIQRGHHECR-CHWSQXEVSA-N 5-fluoro-2-oxo-3-[[(1S,2S)-2-phenylcyclopropyl]methyl]-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@H]2C[C@@H]2CN2C=3C=C(C(=CC=3OC2=O)S(=O)(=O)NC=2SN=CN=2)F)=CC=CC=C1 RAFYTIQRGHHECR-CHWSQXEVSA-N 0.000 claims 1
- HFOSISRCKHKJNC-UHFFFAOYSA-N 5-fluoro-2-oxo-3-spiro[3,4-dihydrochromene-2,3'-oxetane]-4-yl-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1C(C1=CC=CC=C1O1)CC21COC2 HFOSISRCKHKJNC-UHFFFAOYSA-N 0.000 claims 1
- IUKMTZMGQOFRHD-UHFFFAOYSA-N 5-fluoro-3-(5-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1CCC=2C(F)=CC=CC=2C1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 IUKMTZMGQOFRHD-UHFFFAOYSA-N 0.000 claims 1
- ONRNKILAAPUCTN-UHFFFAOYSA-N 5-fluoro-3-(5-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1CCC=2C(C)=CC=CC=2C1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 ONRNKILAAPUCTN-UHFFFAOYSA-N 0.000 claims 1
- RICZNNZICCGKNK-UHFFFAOYSA-N 5-fluoro-3-(6-fluoro-3,4-dihydro-2h-chromen-4-yl)-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC(F)=CC=C2OCCC1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 RICZNNZICCGKNK-UHFFFAOYSA-N 0.000 claims 1
- COYDVCJMGWAARY-UHFFFAOYSA-N 5-fluoro-3-(6-fluorospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1C(N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SC=CN=2)=O)C2=CC(F)=CC=C2OC21CCC2 COYDVCJMGWAARY-UHFFFAOYSA-N 0.000 claims 1
- UNDIVHOGUWEGSX-UHFFFAOYSA-N 5-fluoro-3-(7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC(F)=CC=C2CCCC1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 UNDIVHOGUWEGSX-UHFFFAOYSA-N 0.000 claims 1
- VLPNKLSFUKIGQT-UHFFFAOYSA-N 5-fluoro-3-(7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC(C)=CC=C2CCCC1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 VLPNKLSFUKIGQT-UHFFFAOYSA-N 0.000 claims 1
- IEXFBQNDUJBRLK-GFCCVEGCSA-N 5-fluoro-3-[(1R)-1-[2-(3-hydroxyazetidin-3-yl)phenyl]ethyl]-2-oxo-N-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SC=CN=2)=O)=CC=CC=C1C1(O)CNC1 IEXFBQNDUJBRLK-GFCCVEGCSA-N 0.000 claims 1
- ZSDNGJFWKYWGFZ-CQSZACIVSA-N 5-fluoro-3-[(1R)-1-[2-[2-(3-methylimidazol-4-yl)ethynyl]phenyl]ethyl]-2-oxo-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C#CC1=CN=CN1C ZSDNGJFWKYWGFZ-CQSZACIVSA-N 0.000 claims 1
- RBSBLKBIYJQWPH-GFCCVEGCSA-N 5-fluoro-3-[(1r)-1-(2-methylsulfonyl-3,4-dihydro-1h-isoquinolin-8-yl)ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C=4CN(CCC=4C=CC=3)S(C)(=O)=O)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=NS1 RBSBLKBIYJQWPH-GFCCVEGCSA-N 0.000 claims 1
- OJROGLKNFMINHG-CQSZACIVSA-N 5-fluoro-3-[(1r)-1-[2-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)phenyl]ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C1=CCN(S(C)(=O)=O)CC1 OJROGLKNFMINHG-CQSZACIVSA-N 0.000 claims 1
- ZKZDNBWTRLMQSH-GFCCVEGCSA-N 5-fluoro-3-[(1r)-1-[2-(3-fluoroazetidin-3-yl)phenyl]ethyl]-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SC=CN=2)=O)=CC=CC=C1C1(F)CNC1 ZKZDNBWTRLMQSH-GFCCVEGCSA-N 0.000 claims 1
- DYLTUBRLDWYTEJ-OAHLLOKOSA-N 5-fluoro-3-[(1r)-1-[2-[2-(1-hydroxycyclopentyl)ethynyl]phenyl]ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1C#CC1(O)CCCC1 DYLTUBRLDWYTEJ-OAHLLOKOSA-N 0.000 claims 1
- LUQBNAZKOCBIFZ-GFCCVEGCSA-N 5-fluoro-3-[(1r)-1-[3-(1-methylpyrazol-3-yl)phenyl]ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=1C([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=1C=1C=CN(C)N=1 LUQBNAZKOCBIFZ-GFCCVEGCSA-N 0.000 claims 1
- KOZAPRAEPWVDHK-CYBMUJFWSA-N 5-fluoro-3-[(1r)-1-[3-(1-methylpyrazol-3-yl)phenyl]ethyl]-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=1C([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SC=CN=2)=O)=CC=CC=1C=1C=CN(C)N=1 KOZAPRAEPWVDHK-CYBMUJFWSA-N 0.000 claims 1
- GSGZGXBBQWAXIS-CYBMUJFWSA-N 5-fluoro-3-[(1r)-1-[3-(5-methyl-1h-pyrazol-4-yl)phenyl]ethyl]-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=1C([C@@H](C)N2C(OC3=CC(=C(F)C=C32)S(=O)(=O)NC=2SC=CN=2)=O)=CC=CC=1C1=CNN=C1C GSGZGXBBQWAXIS-CYBMUJFWSA-N 0.000 claims 1
- CAIHBLFVGQWMDJ-PUODRLBUSA-N 5-fluoro-3-[(1r)-1-[7-(methanesulfonamido)-5,6,7,8-tetrahydronaphthalen-1-yl]ethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C=4CC(CCC=4C=CC=3)NS(C)(=O)=O)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=NS1 CAIHBLFVGQWMDJ-PUODRLBUSA-N 0.000 claims 1
- UNMHOFFMUJIHMT-LLVKDONJSA-N 5-fluoro-3-[(1r)-1-isoquinolin-8-ylethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@@H](C=3C4=CN=CC=C4C=CC=3)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=NS1 UNMHOFFMUJIHMT-LLVKDONJSA-N 0.000 claims 1
- UNMHOFFMUJIHMT-NSHDSACASA-N 5-fluoro-3-[(1s)-1-isoquinolin-8-ylethyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=C2OC(=O)N([C@H](C=3C4=CN=CC=C4C=CC=3)C)C2=CC(F)=C1S(=O)(=O)NC1=NC=NS1 UNMHOFFMUJIHMT-NSHDSACASA-N 0.000 claims 1
- LZPBWVNRGDZBGL-UHFFFAOYSA-N 5-fluoro-3-[(2-iodophenyl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC1=CC=CC=C1I LZPBWVNRGDZBGL-UHFFFAOYSA-N 0.000 claims 1
- NMOVBSZCANSTMM-UHFFFAOYSA-N 5-fluoro-3-[(2-methylindazol-7-yl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=NN(C)C=C2C=CC=C1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 NMOVBSZCANSTMM-UHFFFAOYSA-N 0.000 claims 1
- LKMLOLFKDYQBNU-UHFFFAOYSA-N 5-fluoro-3-[(4-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide;hydrochloride Chemical compound Cl.C1=CC=C2C(F)CNCC2=C1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 LKMLOLFKDYQBNU-UHFFFAOYSA-N 0.000 claims 1
- SHCUXLDQYXFBCS-HNNXBMFYSA-N 5-fluoro-3-[(4s)-6-fluorospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@H](C2)N3C(OC4=CC(=C(F)C=C43)S(=O)(=O)NC=3SN=CN=3)=O)=CC(F)=CC=C1OC12CCC1 SHCUXLDQYXFBCS-HNNXBMFYSA-N 0.000 claims 1
- NNYOJPZASIDULS-UHFFFAOYSA-N 5-fluoro-3-[(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=12CC(O)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 NNYOJPZASIDULS-UHFFFAOYSA-N 0.000 claims 1
- DPMDCRUNAVTTLR-SVRRBLITSA-N 5-fluoro-3-[[(1R,2S)-2-iodocyclopropyl]methyl]-2-oxo-N-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1C[C@H]1C[C@@H]1I DPMDCRUNAVTTLR-SVRRBLITSA-N 0.000 claims 1
- WLUFSIVJYRWNPV-HNNXBMFYSA-N 5-fluoro-3-[[(4r)-4-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl]methyl]-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C([C@@H](C1=CC=C2)F)NCC1=C2CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 WLUFSIVJYRWNPV-HNNXBMFYSA-N 0.000 claims 1
- WLUFSIVJYRWNPV-OAHLLOKOSA-N 5-fluoro-3-[[(4s)-4-fluoro-1,2,3,4-tetrahydroisoquinolin-8-yl]methyl]-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C([C@H](C1=CC=C2)F)NCC1=C2CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 WLUFSIVJYRWNPV-OAHLLOKOSA-N 0.000 claims 1
- UPJRZLLMVYGGBF-GFCCVEGCSA-N 5-methyl-2-oxo-3-[(1r)-1-phenylethyl]-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](C)N2C(OC3=CC(=C(C)C=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 UPJRZLLMVYGGBF-GFCCVEGCSA-N 0.000 claims 1
- SJBGKCMICITIKT-UHFFFAOYSA-N C(N)(OC1CC2=C(C=CC=C2CC1)CN1C(OC2=C1C=C(C(=C2)S(NC2=NC=NS2)(=O)=O)F)=O)=O Chemical compound C(N)(OC1CC2=C(C=CC=C2CC1)CN1C(OC2=C1C=C(C(=C2)S(NC2=NC=NS2)(=O)=O)F)=O)=O SJBGKCMICITIKT-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- YTFNSOLGJDBTSV-INIZCTEOSA-N [2-[[(2S)-8-[[5-fluoro-2-oxo-6-(1,2,4-thiadiazol-5-ylsulfamoyl)-1,3-benzoxazol-3-yl]methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]amino]-2-oxoethyl] acetate Chemical compound C([C@@H](CC1=2)NC(=O)COC(=O)C)CC1=CC=CC=2CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 YTFNSOLGJDBTSV-INIZCTEOSA-N 0.000 claims 1
- YTFNSOLGJDBTSV-MRXNPFEDSA-N [2-[[(2r)-8-[[5-fluoro-2-oxo-6-(1,2,4-thiadiazol-5-ylsulfamoyl)-1,3-benzoxazol-3-yl]methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]amino]-2-oxoethyl] acetate Chemical compound C([C@H](CC1=2)NC(=O)COC(=O)C)CC1=CC=CC=2CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 YTFNSOLGJDBTSV-MRXNPFEDSA-N 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims 1
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 239000003292 glue Substances 0.000 claims 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- ZJNRSFIYZBVTTL-UHFFFAOYSA-N n-(4-methyl-1,3-thiazol-2-yl)-2-oxo-3-(1-phenylethyl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=C(S(=O)(=O)NC=3SC=C(C)N=3)C=C2OC(=O)N1C(C)C1=CC=CC=C1 ZJNRSFIYZBVTTL-UHFFFAOYSA-N 0.000 claims 1
- NGPSRPPGSWNVAH-UHFFFAOYSA-N n-[8-[[5-fluoro-2-oxo-6-(1,2,4-thiadiazol-5-ylsulfamoyl)-1,3-benzoxazol-3-yl]methyl]-1,2,3,4-tetrahydronaphthalen-2-yl]acetamide Chemical compound C=12CC(NC(=O)C)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 NGPSRPPGSWNVAH-UHFFFAOYSA-N 0.000 claims 1
- 229910017464 nitrogen compound Inorganic materials 0.000 claims 1
- 150000002830 nitrogen compounds Chemical class 0.000 claims 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 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
- 238000002560 therapeutic procedure Methods 0.000 claims 1
- 0 *c(c(S(N*)(=O)=O)c1)cc(N2*)c1OC2=O Chemical compound *c(c(S(N*)(=O)=O)c1)cc(N2*)c1OC2=O 0.000 description 3
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- LOCFEBZCHQFGKQ-UHFFFAOYSA-N CSc1ncn[s]1 Chemical compound CSc1ncn[s]1 LOCFEBZCHQFGKQ-UHFFFAOYSA-N 0.000 description 1
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| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| JP6014155B2 (ja) | 2011-10-31 | 2016-10-25 | ゼノン・ファーマシューティカルズ・インコーポレイテッドＸｅｎｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｉｎｃ． | ビアリールエーテルスルホンアミドおよび治療剤としてのそれらの使用 |
| KR101719893B1 (ko) | 2012-05-22 | 2017-03-24 | 제넨테크, 인크. | Ｎ-치환된 벤즈아미드 및 통증의 치료에서 이들의 용도 |
| JP6309519B2 (ja) | 2012-07-06 | 2018-04-11 | ジェネンテック， インコーポレイテッド | Ｎ置換ベンズアミド及びその使用方法 |
| WO2014153037A1 (en) | 2013-03-14 | 2014-09-25 | Genentech, Inc. | Substituted triazolopyridines and methods of use thereof |
| EP2970156B1 (en) | 2013-03-15 | 2018-07-25 | Genentech, Inc. | Substituted benzoxazoles and methods of use thereof |
| AU2014356967A1 (en) | 2013-11-27 | 2016-07-07 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| TW201623264A (zh) | 2014-03-29 | 2016-07-01 | 魯賓有限公司 | 作為電位閘控鈉通道調節劑之磺胺化合物 |
| JP2017525677A (ja) | 2014-07-07 | 2017-09-07 | ジェネンテック， インコーポレイテッド | 治療用化合物及びその使用方法 |
| KR102649836B1 (ko) * | 2015-03-02 | 2024-03-22 | 암젠 인크 | 비시클릭 케톤 술폰아마이드 화합물 |
| MA42118A (fr) | 2015-05-22 | 2018-03-28 | Genentech Inc | Benzamides substitués et leurs méthodes d'utilisation |
| WO2017035271A1 (en) | 2015-08-27 | 2017-03-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| MX386501B (es) | 2015-09-28 | 2025-03-19 | Genentech Inc | Compuestos terapeuticos y sus metodos de uso |
| EP3380466A1 (en) | 2015-11-25 | 2018-10-03 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| CN108699015A (zh) | 2015-12-18 | 2018-10-23 | 默沙东公司 | 对电压门控性钠通道具有选择性活性的羟基烷基胺-和羟基环烷基胺-取代的二胺-芳基磺胺化合物 |
| US10766858B2 (en) | 2016-03-30 | 2020-09-08 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| HUE071358T2 (hu) | 2016-05-20 | 2025-08-28 | Xenon Pharmaceuticals Inc | Benzolszulfonamid vegyületek és terápiás szerként való alkalmazásuk |
| JP2019532077A (ja) | 2016-10-17 | 2019-11-07 | ジェネンテック， インコーポレイテッド | 治療用化合物及びその使用方法 |
| JP7022751B2 (ja) | 2016-12-09 | 2022-02-18 | ゼノン・ファーマシューティカルズ・インコーポレイテッド | ベンゼンスルホンアミド化合物および治療剤としてのそれらの使用 |
| CN110546148A (zh) | 2017-03-24 | 2019-12-06 | 基因泰克公司 | 作为钠通道抑制剂的4-哌啶-n-(嘧啶-4-基)色满-7-磺酰胺衍生物 |
| TW201908310A (zh) * | 2017-05-11 | 2019-03-01 | 英商葛蘭素史克智慧財產發展有限公司 | 化合物 |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| EP3774801A1 (en) | 2018-03-30 | 2021-02-17 | F. Hoffmann-La Roche AG | Fused ring hydro-pyrido compounds as sodium channel inhibitors |
| US11512072B2 (en) | 2018-04-19 | 2022-11-29 | University Of Virginia Patent Foundation | Compositions and methods for preparing and using azetidines |
| TW202003490A (zh) | 2018-05-22 | 2020-01-16 | 瑞士商赫孚孟拉羅股份公司 | 治療性化合物及其使用方法 |
| SG11202011862PA (en) | 2018-06-13 | 2020-12-30 | Xenon Pharmaceuticals Inc | Benzenesulfonamide compounds and their use as therapeutic agents |
| CN112638898B (zh) | 2018-08-31 | 2024-04-09 | 泽农医药公司 | 杂芳基取代的磺酰胺化合物及其作为钠通道抑制剂的用途 |
| MX2021001380A (es) | 2018-08-31 | 2021-05-27 | Xenon Pharmaceuticals Inc | Compuestos de sulfonamida sustituidos con heteroarilo y su uso como agentes terapeuticos. |
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| JPH09124620A (ja) | 1995-10-11 | 1997-05-13 | Bristol Myers Squibb Co | 置換ビフェニルスルホンアミドエンドセリン拮抗剤 |
| AU760250B2 (en) | 1998-12-04 | 2003-05-08 | Neurosearch A/S | New benzimidazolone-, benzoxazolone-, or benzothiazolone derivatives as ion channel modulating agents |
| ES2323876T3 (es) * | 2001-04-18 | 2009-07-27 | Euro-Celtique S.A. | Derivados de 1-(4-piperidinil)-1,3-dihidro-2h-benzoxazol-2-ona y compuestos relacionados como analogos de la nociceptina y ligandos de orl1 para el tratamiento del dolor. |
| EP1467986A1 (en) * | 2002-01-17 | 2004-10-20 | Eli Lilly And Company | Aza-cyclic compounds as modulators of acetylcholine receptors |
| RU2007145434A (ru) * | 2005-05-10 | 2009-06-20 | Вертекс Фармасьютикалз Инкорпорейтед (Us) | Бициклические производные в качестве модуляторов ионных каналов |
| ZA200800191B (en) * | 2005-06-09 | 2009-04-29 | Vertex Pharmaceuicals Inc | Indane derivatives as modulators of ion channels |
| WO2007075895A2 (en) * | 2005-12-21 | 2007-07-05 | Vertex Pharmaceuticals Incorporated | Heterocyclic derivatives as modulators of ion channels |
| US8124610B2 (en) * | 2007-07-13 | 2012-02-28 | Icagen Inc. | Sodium channel inhibitors |
| CN102159077A (zh) * | 2008-08-21 | 2011-08-17 | 吉瑞工厂 | 用于治疗神经性疼痛的方法 |
| HRP20150355T1 (hr) | 2009-01-12 | 2015-06-19 | Pfizer Limited | Sulfonamidni derivati |
| DK2427441T3 (en) * | 2009-05-04 | 2017-03-20 | Agios Pharmaceuticals Inc | PKM2 Activators for use in the treatment of cancer |
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- 2012-10-26 US US14/353,488 patent/US9273040B2/en active Active
- 2012-10-26 CN CN201280052937.2A patent/CN103889419A/zh active Pending
- 2012-10-26 JP JP2014539066A patent/JP2014532660A/ja active Pending
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