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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| 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 |
| US9630929B2 (en) | 2011-10-31 | 2017-04-25 | Xenon Pharmaceuticals Inc. | Benzenesulfonamide compounds and their use as therapeutic agents |
| SG11201408284VA (en) | 2012-05-22 | 2015-02-27 | Xenon Pharmaceuticals Inc | N-substituted benzamides and their use in the treatment of pain |
| US10071957B2 (en) | 2012-07-06 | 2018-09-11 | Genentech, Inc. | N-substituted benzamides and methods of use thereof |
| US9550775B2 (en) | 2013-03-14 | 2017-01-24 | Genentech, Inc. | Substituted triazolopyridines and methods of use thereof |
| MX2015010775A (es) | 2013-03-15 | 2016-04-25 | Genentech Inc | Benzoxazoles sustituidos y metodos para usarlos. |
| CR20160296A (es) | 2013-11-27 | 2016-09-20 | Genentech Inc | Benzamidas sustituidas y métodos para usarlas |
| 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 |
| CN106715418A (zh) | 2014-07-07 | 2017-05-24 | 基因泰克公司 | 治疗化合物及其使用方法 |
| EA032928B1 (ru) * | 2015-03-02 | 2019-08-30 | Эмджен Инк. | Бициклические кетосульфонамидные соединения |
| JP2018520107A (ja) | 2015-05-22 | 2018-07-26 | ジェネンテック， インコーポレイテッド | 置換ベンズアミド及びその使用方法 |
| EP3341353A1 (en) | 2015-08-27 | 2018-07-04 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| CN108290881B (zh) | 2015-09-28 | 2021-12-07 | 健泰科生物技术公司 | 治疗性化合物和其使用方法 |
| US10899732B2 (en) | 2015-11-25 | 2021-01-26 | Genentech, Inc. | Substituted benzamides useful as sodium channel blockers |
| EP3390374B1 (en) | 2015-12-18 | 2020-08-26 | Merck Sharp & Dohme Corp. | Hydroxyalkylamine- and hydroxycycloalkylamine-substituted diamine-arylsulfonamide compounds with selective activity in voltage-gated sodium channels |
| EP3854782A1 (en) | 2016-03-30 | 2021-07-28 | Genentech, Inc. | Substituted benzamides and methods of use thereof |
| HRP20250505T1 (hr) | 2016-05-20 | 2025-06-20 | Xenon Pharmaceuticals Inc. | Spojevi benzensulfonamida i njihova uporaba za terapijska sredstva |
| AU2017347549A1 (en) | 2016-10-17 | 2019-05-02 | Genentech, Inc. | Therapeutic compounds and methods of use thereof |
| ES2967410T3 (es) | 2016-12-09 | 2024-04-30 | Xenon Pharmaceuticals Inc | Compuestos de bencenosulfonamida y sus usos en forma de agentes terapéuticos |
| JP2020511511A (ja) | 2017-03-24 | 2020-04-16 | ジェネンテック， インコーポレイテッド | ナトリウムチャネル阻害剤としての４−ピペリジン−ｎ−（ピリミジン−４−イル）クロマン−７−スルホンアミド誘導体 |
| WO2018205948A1 (en) * | 2017-05-11 | 2018-11-15 | Glaxosmithkline Intellectual Property Development Limited | Compounds |
| AR114263A1 (es) | 2018-02-26 | 2020-08-12 | Genentech Inc | Compuestos terapéuticos y métodos para utilizarlos |
| WO2019191702A1 (en) | 2018-03-30 | 2019-10-03 | F. Hoffmann-La Roche Ag | Substituted hydro-pyrido-azines as sodium channel inhibitors |
| WO2019204740A1 (en) * | 2018-04-19 | 2019-10-24 | 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 |
| CN112262142B (zh) | 2018-06-13 | 2023-11-14 | 泽农医药公司 | 苯磺酰胺化合物及其作为治疗剂的用途 |
| MX2021001380A (es) | 2018-08-31 | 2021-05-27 | Xenon Pharmaceuticals Inc | Compuestos de sulfonamida sustituidos con heteroarilo y su uso como agentes terapeuticos. |
| MA53488A (fr) | 2018-08-31 | 2021-12-08 | Xenon Pharmaceuticals Inc | Composés de sulfonamide substitués par hétéroaryle et leur utilisation en tant qu'inhibiteurs de canaux sodiques |
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| CA2349616A1 (en) * | 1998-12-04 | 2000-06-15 | Neurosearch A/S | New benzimidazolone-, benzoxazolone-, or benzothiazolone derivatives as ion channel modulating agents |
| IL158484A0 (en) | 2001-04-18 | 2004-05-12 | Euro Celtique Sa | Nociceptin analogs |
| US7408067B2 (en) | 2002-01-17 | 2008-08-05 | Merck + Co., Inc. | Aza-cyclic compounds as modulators of acetylcholine receptors |
| MX2007014180A (es) * | 2005-05-10 | 2008-01-14 | Vertex Pharma | Derivados biciclicos como moduladores de canales de iones. |
| MX2007015726A (es) | 2005-06-09 | 2008-03-04 | Vertex Pharma | Derivados de indano como moduladores de canales ionicos. |
| EP2316829A1 (en) | 2005-12-21 | 2011-05-04 | Vertex Pharmaceuticals Incorporated | Heterocyclic derivatives as modulators of ion channels |
| US8124610B2 (en) * | 2007-07-13 | 2012-02-28 | Icagen Inc. | Sodium channel inhibitors |
| US20110190347A1 (en) | 2008-08-21 | 2011-08-04 | Richter Gedeon Nyrt. | Methods for treating neuropathic pain |
| PE20120008A1 (es) | 2009-01-12 | 2012-01-24 | Icagen Inc | Derivados de fenoxi bencenosulfonamida |
| DK2427441T3 (en) * | 2009-05-04 | 2017-03-20 | Agios Pharmaceuticals Inc | PKM2 Activators for use in the treatment of cancer |
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