MX2014005068A - Compuestos de benzoxazolinona con actividad selectiva en canales de sodio activados por voltaje. - Google Patents

Info

Publication number

MX2014005068A

MX2014005068A MX2014005068A MX2014005068A MX2014005068A MX 2014005068 A MX2014005068 A MX 2014005068A MX 2014005068 A MX2014005068 A MX 2014005068A MX 2014005068 A MX2014005068 A MX 2014005068A MX 2014005068 A MX2014005068 A MX 2014005068A

Authority

MX

Mexico

Prior art keywords

oxo

sulfonamide

dihydro

benzoxazole

fluoro

Prior art date

2011-10-28

Links

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• Global Dossier
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• 230000000694 effects Effects 0.000 title claims description 20
• ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 title claims description 10
• 108010053752 Voltage-Gated Sodium Channels Proteins 0.000 title description 2
• 102000016913 Voltage-Gated Sodium Channels Human genes 0.000 title description 2
• 150000001875 compounds Chemical class 0.000 claims abstract description 265
• 150000003839 salts Chemical class 0.000 claims abstract description 53
• 208000004296 neuralgia Diseases 0.000 claims abstract description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 16
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
• 208000021722 neuropathic pain Diseases 0.000 claims abstract description 14
• 230000000903 blocking effect Effects 0.000 claims abstract description 8
• 208000035475 disorder Diseases 0.000 claims abstract description 7
• -1 heteroaryl radical Chemical class 0.000 claims description 432
• 229910052739 hydrogen Inorganic materials 0.000 claims description 181
• 229940124530 sulfonamide Drugs 0.000 claims description 155
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 139
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 129
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 102
• 150000003254 radicals Chemical class 0.000 claims description 89
• 125000000217 alkyl group Chemical group 0.000 claims description 83
• 229910052736 halogen Inorganic materials 0.000 claims description 79
• 150000002367 halogens Chemical class 0.000 claims description 74
• 125000003118 aryl group Chemical group 0.000 claims description 69
• CBEHYNBKRUICOR-UHFFFAOYSA-N 1,3-benzoxazole-6-sulfonamide Chemical compound NS(=O)(=O)C1=CC=C2N=COC2=C1 CBEHYNBKRUICOR-UHFFFAOYSA-N 0.000 claims description 61
• 229910052799 carbon Inorganic materials 0.000 claims description 52
• 125000004432 carbon atom Chemical group C* 0.000 claims description 41
• 150000001721 carbon Chemical group 0.000 claims description 36
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 34
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 33
• 125000004516 1,2,4-thiadiazol-5-yl group Chemical group S1N=CN=C1* 0.000 claims description 32
• 125000003545 alkoxy group Chemical group 0.000 claims description 31
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 28
• 125000004429 atom Chemical group 0.000 claims description 27
• 229910052757 nitrogen Inorganic materials 0.000 claims description 27
• 108010052164 Sodium Channels Proteins 0.000 claims description 26
• 102000018674 Sodium Channels Human genes 0.000 claims description 26
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 25
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 22
• 229910052717 sulfur Inorganic materials 0.000 claims description 22
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
• 125000000623 heterocyclic group Chemical group 0.000 claims description 20
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
• 125000006413 ring segment Chemical group 0.000 claims description 18
• LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000004122 cyclic group Chemical group 0.000 claims description 17
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 16
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 16
• 239000001257 hydrogen Substances 0.000 claims description 16
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
• 125000005843 halogen group Chemical group 0.000 claims description 14
• 239000003814 drug Substances 0.000 claims description 13
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 13
• NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 13
• SGDGUNVZAQYYLO-UHFFFAOYSA-N 2,3-dihydro-1,3-benzoxazole-6-sulfonamide Chemical compound NS(=O)(=O)C1=CC=C2NCOC2=C1 SGDGUNVZAQYYLO-UHFFFAOYSA-N 0.000 claims description 12
• 150000005840 aryl radicals Chemical class 0.000 claims description 12
• UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 12
• ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
• 125000005842 heteroatom Chemical group 0.000 claims description 11
• 229910052760 oxygen Inorganic materials 0.000 claims description 11
• AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 10
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
• 125000003342 alkenyl group Chemical group 0.000 claims description 9
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 9
• 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 9
• RLSSLKRGSUZGIB-UHFFFAOYSA-N 3-(1,3-thiazol-2-yl)-2H-1,3-benzoxazole-6-sulfonamide Chemical compound S1C(=NC=C1)N1COC2=C1C=CC(=C2)S(=O)(=O)N RLSSLKRGSUZGIB-UHFFFAOYSA-N 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 101100092284 Mus musculus Rragd gene Proteins 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims description 8
• 241000251737 Raja Species 0.000 claims description 6
• 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 150000001412 amines Chemical class 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 125000003386 piperidinyl group Chemical group 0.000 claims description 5
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 4
• HDQYQGSMPMOTSC-CYBMUJFWSA-N 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=C1S(=O)(=O)NC1=NC=CS1 HDQYQGSMPMOTSC-CYBMUJFWSA-N 0.000 claims description 4
• 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 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 3
• 125000006304 2-iodophenyl group Chemical group [H]C1=C([H])C(I)=C(*)C([H])=C1[H] 0.000 claims description 3
• KYSFPLZZMUVJBW-UHFFFAOYSA-N 3-[[7-(methylamino)-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(NC)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 KYSFPLZZMUVJBW-UHFFFAOYSA-N 0.000 claims description 3
• 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 description 3
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 3
• 125000004414 alkyl thio group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
• 125000005110 aryl thio group Chemical group 0.000 claims description 3
• 125000002619 bicyclic group Chemical group 0.000 claims description 3
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
• 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 3
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
• 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 description 3
• 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 2
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
• KWTKZSURMOQRLX-UHFFFAOYSA-N 2-(1,2,3,6-tetrahydropyridin-4-yl)phenol Chemical compound OC1=CC=CC=C1C1=CCNCC1 KWTKZSURMOQRLX-UHFFFAOYSA-N 0.000 claims description 2
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
• 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 description 2
• 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 description 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 description 2
• XBQPAZJVFCROBN-UHFFFAOYSA-N 3-(2,3-dihydro-1h-isoindol-4-ylmethyl)-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C=4CNCC=4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 XBQPAZJVFCROBN-UHFFFAOYSA-N 0.000 claims description 2
• DNVIMYOABMBTTD-UHFFFAOYSA-N 3-(2-chloro-5,6,7,8-tetrahydroquinolin-8-yl)-5-fluoro-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound FC1=CC=2N(C3C4=NC(Cl)=CC=C4CCC3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=CS1 DNVIMYOABMBTTD-UHFFFAOYSA-N 0.000 claims description 2
• DLPPPGKGUMYFTQ-UHFFFAOYSA-N 3-(3,4-dihydro-2h-chromen-4-yl)-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound FC1=CC=2N(C3C4=CC=CC=C4OCC3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 DLPPPGKGUMYFTQ-UHFFFAOYSA-N 0.000 claims description 2
• LKZILEICQGLWMT-UHFFFAOYSA-N 3-(5,7-difluoro-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(F)=CC(F)=C2CCCC1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=CS1 LKZILEICQGLWMT-UHFFFAOYSA-N 0.000 claims description 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 description 2
• FSJNLNOKMPUFNJ-UHFFFAOYSA-N 3-(6-bromospiro[3,4-dihydrochromene-2,1'-cyclobutane]-4-yl)-5-fluoro-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SC=CN=3)C(F)=CC=2N1C(C1=CC(Br)=CC=C1O1)CC21CCC2 FSJNLNOKMPUFNJ-UHFFFAOYSA-N 0.000 claims description 2
• XRCQNQYABKKKOJ-UHFFFAOYSA-N 3-(isoquinolin-8-ylmethyl)-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=2N(CC=3C4=CN=CC=C4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 XRCQNQYABKKKOJ-UHFFFAOYSA-N 0.000 claims description 2
• ZPGFANZLTDXOMH-LBPRGKRZSA-N 3-[(1S)-1-[2-(3-aminopropyl)phenyl]ethyl]-5-fluoro-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=C1CCCN ZPGFANZLTDXOMH-LBPRGKRZSA-N 0.000 claims description 2
• NEYAIJNNTOGVRX-CYBMUJFWSA-N 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(=CC=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=1C=1C=CN(C)N=1 NEYAIJNNTOGVRX-CYBMUJFWSA-N 0.000 claims description 2
• HLHIGROOBCDZPJ-GFCCVEGCSA-N 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=C1S(=O)(=O)NC1=NC=NS1 HLHIGROOBCDZPJ-GFCCVEGCSA-N 0.000 claims description 2
• LXFYWBJDUPDTRH-CQSZACIVSA-N 3-[(1r)-3-fluoro-1-phenylpropyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1([C@@H](CCF)N2C(OC3=CC(=CC=C32)S(=O)(=O)NC=2SN=CN=2)=O)=CC=CC=C1 LXFYWBJDUPDTRH-CQSZACIVSA-N 0.000 claims description 2
• KUYIUIJMYJHOJT-UHFFFAOYSA-N 3-[(3-aminoisoquinolin-5-yl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=C2C=NC(N)=CC2=C1CN(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 KUYIUIJMYJHOJT-UHFFFAOYSA-N 0.000 claims description 2
• OBHCYJSATLTMIR-UHFFFAOYSA-N 3-[(3-aminoisoquinolin-5-yl)methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC=C2C=NC(N)=CC2=C1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 OBHCYJSATLTMIR-UHFFFAOYSA-N 0.000 claims description 2
• PUYJRJNBXTWRFI-UHFFFAOYSA-N 3-[(3-aminoisoquinolin-8-yl)methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=12C=NC(N)=CC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 PUYJRJNBXTWRFI-UHFFFAOYSA-N 0.000 claims description 2
• ORRWBHXQPYKUOH-UHFFFAOYSA-N 3-[(3-bromophenyl)methyl]-5-fluoro-2-oxo-n-(1,3-thiazol-2-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SC=CN=3)C(F)=CC=2N1CC1=CC=CC(Br)=C1 ORRWBHXQPYKUOH-UHFFFAOYSA-N 0.000 claims description 2
• SDMRRXUKIYKVLF-UHFFFAOYSA-N 3-[(3-chloroisoquinolin-8-yl)methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound FC1=CC=2N(CC=3C4=CN=C(Cl)C=C4C=CC=3)C(=O)OC=2C=C1S(=O)(=O)NC1=NC=NS1 SDMRRXUKIYKVLF-UHFFFAOYSA-N 0.000 claims description 2
• PAHPKYAJLHCBGH-UHFFFAOYSA-N 3-[1-[7-(3,3-difluoroazetidin-1-yl)-5,6,7,8-tetrahydronaphthalen-1-yl]ethyl]-5-fluoro-2-oxo-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=1C2)=CC=CC=1CCC2N1CC(F)(F)C1 PAHPKYAJLHCBGH-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• CWSFYGIJIYEZFO-UHFFFAOYSA-N 3-[[7-(3,3-difluoropyrrolidin-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 Chemical compound O=C1OC=2C=C(S(=O)(=O)NC=3SN=CN=3)C(F)=CC=2N1CC(C=1C2)=CC=CC=1CCC2N1CCC(F)(F)C1 CWSFYGIJIYEZFO-UHFFFAOYSA-N 0.000 claims description 2
• QOUKCDACXGDXFK-UHFFFAOYSA-N 3-[[7-(benzylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]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=2N1CC(C=1C2)=CC=CC=1CCC2NCC1=CC=CC=C1 QOUKCDACXGDXFK-UHFFFAOYSA-N 0.000 claims description 2
• KKQUBTODISKIRZ-UHFFFAOYSA-N 3-[[7-(dimethylamino)-5,6,7,8-tetrahydronaphthalen-1-yl]methyl]-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C=12CC(N(C)C)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 KKQUBTODISKIRZ-UHFFFAOYSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• PQXMVRPDJJJDKJ-LLVKDONJSA-N 5-fluoro-3-[(1r)-1-[2-(3-fluoroazetidin-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(F)CNC1 PQXMVRPDJJJDKJ-LLVKDONJSA-N 0.000 claims description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 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 description 2
• 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 2
• 125000003435 aroyl group Chemical group 0.000 claims description 2
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
• 125000004475 heteroaralkyl group Chemical group 0.000 claims description 2
• 125000005150 heteroarylsulfinyl group Chemical group 0.000 claims description 2
• 125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 2
• 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
• DXASQZJWWGZNSF-UHFFFAOYSA-N n,n-dimethylmethanamine;sulfur trioxide Chemical group CN(C)C.O=S(=O)=O DXASQZJWWGZNSF-UHFFFAOYSA-N 0.000 claims description 2
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
• IPBVNPXQWQGGJP-UHFFFAOYSA-N phenyl acetate Chemical compound CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 claims description 2
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 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
• VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-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
• ITBIBSKLXTXEPR-AWEZNQCLSA-N 3-[[(7s)-7-amino-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([C@@H](CC1=2)N)CC1=CC=CC=2CN(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 ITBIBSKLXTXEPR-AWEZNQCLSA-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
• 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
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
• UILTZWLIHNDMDA-UHFFFAOYSA-N 2-(2,2,2-trifluoroethyl)-3,4-dihydro-1H-isoquinoline Chemical compound FC(CN1CC2=CC=CC=C2CC1)(F)F UILTZWLIHNDMDA-UHFFFAOYSA-N 0.000 claims 1
• 125000006481 2-iodobenzyl group Chemical group [H]C1=C([H])C(I)=C(C([H])=C1[H])C([H])([H])* 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
• 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 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
• 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
• 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 1
• 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 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
• UULFBWMKYCYMIK-UHFFFAOYSA-N 2-oxo-3-[[3-(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=2N1CC(C=1)=CC=CC=1C1=CCNCCC1 UULFBWMKYCYMIK-UHFFFAOYSA-N 0.000 claims 1
• BESVQLJVMUXYCZ-UHFFFAOYSA-N 3-(4,4-dimethyl-2,3-dihydro-1h-naphthalen-1-yl)-5-fluoro-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C12=CC=CC=C2C(C)(C)CCC1N(C(OC1=C2)=O)C1=CC(F)=C2S(=O)(=O)NC1=NC=NS1 BESVQLJVMUXYCZ-UHFFFAOYSA-N 0.000 claims 1
• XBIWJAJZBLWLSD-LBPRGKRZSA-N 3-[(1S)-1-[2-(azetidin-3-yl)phenyl]ethyl]-5-fluoro-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=C1C1CNC1 XBIWJAJZBLWLSD-LBPRGKRZSA-N 0.000 claims 1
• ZPGFANZLTDXOMH-GFCCVEGCSA-N 3-[(1r)-1-[2-(3-aminopropyl)phenyl]ethyl]-5-fluoro-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=C1CCCN ZPGFANZLTDXOMH-GFCCVEGCSA-N 0.000 claims 1
• XUXAMQYTNTXJQG-LLVKDONJSA-N 3-[(1r)-1-[2-(azetidin-3-yl)phenyl]ethyl]-5-fluoro-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=C1C1CNC1 XUXAMQYTNTXJQG-LLVKDONJSA-N 0.000 claims 1
• FOHGHYYKTOULOL-UHFFFAOYSA-N 3-[(2-chlorophenyl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound ClC1=CC=CC=C1CN1C(=O)OC2=CC(S(=O)(=O)NC=3SN=CN=3)=CC=C21 FOHGHYYKTOULOL-UHFFFAOYSA-N 0.000 claims 1
• CVJIONIZVZAXKC-UHFFFAOYSA-N 3-[(2-ethyl-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(CC)CCC2=CC=CC=1CN(C(OC1=C2)=O)C1=CC=C2S(=O)(=O)NC1=NC=NS1 CVJIONIZVZAXKC-UHFFFAOYSA-N 0.000 claims 1
• WWIBYNJIUUFFEX-UHFFFAOYSA-N 3-[(3-chlorophenyl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound ClC1=CC=CC(CN2C(OC3=CC(=CC=C32)S(=O)(=O)NC=2SN=CN=2)=O)=C1 WWIBYNJIUUFFEX-UHFFFAOYSA-N 0.000 claims 1
• QZZRWMKVMGKCBZ-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-2-oxo-n-(1,2,4-thiadiazol-5-yl)-1,3-benzoxazole-6-sulfonamide Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)OC2=CC(S(=O)(=O)NC=3SN=CN=3)=CC=C21 QZZRWMKVMGKCBZ-UHFFFAOYSA-N 0.000 claims 1
• CRZBEBRDFGHXBG-UHFFFAOYSA-N 3-[1,3-oxazol-2-yl(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)C1=NC=CO1 CRZBEBRDFGHXBG-UHFFFAOYSA-N 0.000 claims 1
• 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 1
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