KR101840503B1 - 케모카인 수용체 조절제로서의 신규한 1,2-비스-설폰아마이드 유도체 - Google Patents
케모카인 수용체 조절제로서의 신규한 1,2-비스-설폰아마이드 유도체 Download PDFInfo
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- KR101840503B1 KR101840503B1 KR1020137018473A KR20137018473A KR101840503B1 KR 101840503 B1 KR101840503 B1 KR 101840503B1 KR 1020137018473 A KR1020137018473 A KR 1020137018473A KR 20137018473 A KR20137018473 A KR 20137018473A KR 101840503 B1 KR101840503 B1 KR 101840503B1
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- phenyl
- sulfonamide
- sulfonyl
- dichloro
- Prior art date
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- 229940124530 sulfonamide Drugs 0.000 title claims abstract description 34
- 102000009410 Chemokine receptor Human genes 0.000 title abstract description 26
- 108050000299 Chemokine receptor Proteins 0.000 title abstract description 26
- 238000000034 method Methods 0.000 claims abstract description 65
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 15
- -1 phenyl-4-acetamide Chemical group 0.000 claims description 187
- 150000001875 compounds Chemical class 0.000 claims description 113
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 88
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 78
- 239000000460 chlorine Substances 0.000 claims description 57
- 125000000623 heterocyclic group Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims description 24
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 20
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Natural products OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 17
- UNKGLROROYOMAP-UHFFFAOYSA-N n-[3-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]pyridin-2-yl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=NC=CC=2)NS(=O)(=O)C=2SC=CC=2)=C1 UNKGLROROYOMAP-UHFFFAOYSA-N 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- UXGVMFHEKMGWMA-UHFFFAOYSA-N 2-benzofuran Chemical compound C1=CC=CC2=COC=C21 UXGVMFHEKMGWMA-UHFFFAOYSA-N 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- IWKMKEXKTCBKBU-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]furan-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CO1 IWKMKEXKTCBKBU-UHFFFAOYSA-N 0.000 claims description 10
- 150000003456 sulfonamides Chemical class 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- GSNUFIFRDBKVIE-UHFFFAOYSA-N 2,5-dimethylfuran Chemical compound CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 claims description 8
- QERYCTSHXKAMIS-UHFFFAOYSA-M thiophene-2-carboxylate Chemical compound [O-]C(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-M 0.000 claims description 8
- AUIVPJUXCLZULI-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound C=1C=C2NC(=O)CC2=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 AUIVPJUXCLZULI-UHFFFAOYSA-N 0.000 claims description 7
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 6
- JAMUNYLJHUVASZ-UHFFFAOYSA-N n-[4,5-dichloro-2-[(4-pyrazol-1-ylphenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C(N2N=CC=C2)C=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 JAMUNYLJHUVASZ-UHFFFAOYSA-N 0.000 claims description 6
- UOTBUXBRMOIBRF-UHFFFAOYSA-N n-[4,5-dichloro-2-[[4-(2-methyl-1,3-thiazol-4-yl)phenyl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound S1C(C)=NC(C=2C=CC(=CC=2)S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 UOTBUXBRMOIBRF-UHFFFAOYSA-N 0.000 claims description 6
- UXTNDKGCBJPVAP-UHFFFAOYSA-N n-[4-chloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C=1C(Cl)=CC=C(NS(=O)(=O)C=2OC3=CC=CC=C3C=2)C=1NS(=O)(=O)C1=CC=CS1 UXTNDKGCBJPVAP-UHFFFAOYSA-N 0.000 claims description 6
- MOEQTYOILJRYTG-UHFFFAOYSA-N n-[5-chloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C=1C2=CC=CC=C2OC=1S(=O)(=O)NC1=CC(Cl)=CC=C1NS(=O)(=O)C1=CC=CS1 MOEQTYOILJRYTG-UHFFFAOYSA-N 0.000 claims description 6
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
- 125000003944 tolyl group Chemical group 0.000 claims description 6
- NBCXZMCNSBIULL-UHFFFAOYSA-N 6-chloro-n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]pyridine-3-sulfonamide Chemical compound C1=NC(Cl)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 NBCXZMCNSBIULL-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 5
- HNSZSFAGCBWFAE-UHFFFAOYSA-N methyl 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]thiophene-2-carboxylate Chemical compound S1C=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1C(=O)OC HNSZSFAGCBWFAE-UHFFFAOYSA-N 0.000 claims description 5
- KUEMGONZQPTGQF-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1-methylimidazole-4-sulfonamide Chemical compound CN1C=NC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 KUEMGONZQPTGQF-UHFFFAOYSA-N 0.000 claims description 5
- KZLABQSPMHCRTO-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1-methylpyrazole-3-sulfonamide Chemical compound CN1C=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=N1 KZLABQSPMHCRTO-UHFFFAOYSA-N 0.000 claims description 5
- OJKBRNBLMQAFMH-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-3,5-dimethyl-1h-pyrazole-4-sulfonamide Chemical compound CC1=NNC(C)=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 OJKBRNBLMQAFMH-UHFFFAOYSA-N 0.000 claims description 5
- PNISNTXGILJGJJ-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-5-chloro-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 PNISNTXGILJGJJ-UHFFFAOYSA-N 0.000 claims description 5
- NRNTVHBMZYXMTJ-UHFFFAOYSA-N n-[2-[(4-bromo-3-methylphenyl)sulfonylamino]-4,5-dichlorophenyl]thiophene-2-sulfonamide Chemical compound C1=C(Br)C(C)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 NRNTVHBMZYXMTJ-UHFFFAOYSA-N 0.000 claims description 5
- HWFOPKYAZBUHQR-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC(NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1NS(=O)(=O)C1=CC=CS1 HWFOPKYAZBUHQR-UHFFFAOYSA-N 0.000 claims description 5
- JVESWVZNCUVULM-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-benzothiophene-2-sulfonamide Chemical compound C=1C2=CC=CC=C2SC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 JVESWVZNCUVULM-UHFFFAOYSA-N 0.000 claims description 5
- OLRREVPJKLTLGE-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-methyl-2,3-dioxoindole-5-sulfonamide Chemical compound C=1C=C2N(C)C(=O)C(=O)C2=CC=1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 OLRREVPJKLTLGE-UHFFFAOYSA-N 0.000 claims description 5
- TZGZGNZMIAWUHP-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-methylpyrazole-3-sulfonamide Chemical compound CN1C=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=N1 TZGZGNZMIAWUHP-UHFFFAOYSA-N 0.000 claims description 5
- AQOWLXBESAYZSM-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-5-methylfuran-2-sulfonamide Chemical compound O1C(C)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 AQOWLXBESAYZSM-UHFFFAOYSA-N 0.000 claims description 5
- YGPWSXALYCADKC-UHFFFAOYSA-N n-[4,5-dichloro-2-[(2,4-difluorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound FC1=CC(F)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 YGPWSXALYCADKC-UHFFFAOYSA-N 0.000 claims description 5
- HGPXGXHKKPCOEC-UHFFFAOYSA-N n-[4,5-dichloro-2-[(2-chlorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound ClC1=CC=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 HGPXGXHKKPCOEC-UHFFFAOYSA-N 0.000 claims description 5
- SRTBQAGPJOVBAK-UHFFFAOYSA-N n-[4,5-dichloro-2-[(2-fluorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound FC1=CC=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 SRTBQAGPJOVBAK-UHFFFAOYSA-N 0.000 claims description 5
- LVGOYWJEYPMVEE-UHFFFAOYSA-N n-[4,5-dichloro-2-[(3,4-dichlorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(Cl)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 LVGOYWJEYPMVEE-UHFFFAOYSA-N 0.000 claims description 5
- FTVOLBQLIDUANF-UHFFFAOYSA-N n-[4,5-dichloro-2-[(3,5-dichloro-2-hydroxyphenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound OC1=C(Cl)C=C(Cl)C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 FTVOLBQLIDUANF-UHFFFAOYSA-N 0.000 claims description 5
- SHLQEFPZZAVYHO-UHFFFAOYSA-N n-[4,5-dichloro-2-[(3-chloro-2-fluorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound FC1=C(Cl)C=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 SHLQEFPZZAVYHO-UHFFFAOYSA-N 0.000 claims description 5
- FBPDCZSRDOEBQN-UHFFFAOYSA-N n-[4,5-dichloro-2-[(3-chlorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound ClC1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 FBPDCZSRDOEBQN-UHFFFAOYSA-N 0.000 claims description 5
- BUMXKOUEEDLDBE-UHFFFAOYSA-N n-[4,5-dichloro-2-[(4-chloro-2-fluorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound FC1=CC(Cl)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 BUMXKOUEEDLDBE-UHFFFAOYSA-N 0.000 claims description 5
- YXBUMTQXAXKLSM-UHFFFAOYSA-N n-[4,5-dichloro-2-[(4-fluorophenyl)sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 YXBUMTQXAXKLSM-UHFFFAOYSA-N 0.000 claims description 5
- KZGQESHVHUOWIF-UHFFFAOYSA-N n-[4,5-dichloro-2-[[3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 KZGQESHVHUOWIF-UHFFFAOYSA-N 0.000 claims description 5
- KDVJFNNWAOJCQE-UHFFFAOYSA-N n-[4,5-dichloro-2-[[4-fluoro-3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 KDVJFNNWAOJCQE-UHFFFAOYSA-N 0.000 claims description 5
- QIAVTLRHSCMUDO-UHFFFAOYSA-N n-[5-chloro-2-(2-methylpropylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound CC(C)CS(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 QIAVTLRHSCMUDO-UHFFFAOYSA-N 0.000 claims description 5
- CXPZTNPITZJJMO-UHFFFAOYSA-N n-[5-chloro-2-[(2,6-dichlorophenyl)sulfonylamino]phenyl]-1-benzofuran-2-sulfonamide Chemical compound C=1C2=CC=CC=C2OC=1S(=O)(=O)NC1=CC(Cl)=CC=C1NS(=O)(=O)C1=C(Cl)C=CC=C1Cl CXPZTNPITZJJMO-UHFFFAOYSA-N 0.000 claims description 5
- CLIDPBUXRFVZQU-UHFFFAOYSA-N n-[5-chloro-2-[(2,6-difluorophenyl)sulfonylamino]phenyl]-1-benzofuran-2-sulfonamide Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 CLIDPBUXRFVZQU-UHFFFAOYSA-N 0.000 claims description 5
- QNXSIHLBSVDMGT-UHFFFAOYSA-N n-[5-chloro-2-[(3,4-dimethylphenyl)sulfonylamino]phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=C(C)C(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 QNXSIHLBSVDMGT-UHFFFAOYSA-N 0.000 claims description 5
- LDCSCOIEHKMYOL-UHFFFAOYSA-N n-[5-chloro-2-[(5-methylthiophen-2-yl)sulfonylamino]phenyl]-1-benzofuran-2-sulfonamide Chemical compound S1C(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 LDCSCOIEHKMYOL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012453 solvate Substances 0.000 claims description 5
- HRNNHLLBRNZFED-UHFFFAOYSA-N 2,5-dichloro-n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]thiophene-3-sulfonamide Chemical compound S1C(Cl)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1Cl HRNNHLLBRNZFED-UHFFFAOYSA-N 0.000 claims description 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- WTNGKGPALMEFRV-UHFFFAOYSA-N 4-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 WTNGKGPALMEFRV-UHFFFAOYSA-N 0.000 claims description 4
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 claims description 4
- QRAOZQGIUIDZQZ-UHFFFAOYSA-N 4-methyl-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,3-dihydro-1,4-benzoxazine Chemical compound C=1C=C2N(C)CCOC2=CC=1B1OC(C)(C)C(C)(C)O1 QRAOZQGIUIDZQZ-UHFFFAOYSA-N 0.000 claims description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims description 4
- ZCEOISBDNGGFCA-UHFFFAOYSA-N 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-ethoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 ZCEOISBDNGGFCA-UHFFFAOYSA-N 0.000 claims description 4
- ICEIGFRDVCDWFK-UHFFFAOYSA-N 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 ICEIGFRDVCDWFK-UHFFFAOYSA-N 0.000 claims description 4
- FHAIERRISXKJIO-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-methoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OC)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 FHAIERRISXKJIO-UHFFFAOYSA-N 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- FHKWGRBKJXPNDG-UHFFFAOYSA-N ethyl 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]furan-3-carboxylate Chemical compound CCOC(=O)C1=COC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 FHKWGRBKJXPNDG-UHFFFAOYSA-N 0.000 claims description 4
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims description 4
- ZFSQNAREEFPZJL-UHFFFAOYSA-N methyl 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-1-methylpyrrole-2-carboxylate Chemical compound CN1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 ZFSQNAREEFPZJL-UHFFFAOYSA-N 0.000 claims description 4
- FOEBLVGHZUZOQU-UHFFFAOYSA-N methyl 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 FOEBLVGHZUZOQU-UHFFFAOYSA-N 0.000 claims description 4
- NWZGGBGILYYNSW-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1,3-benzodioxole-5-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5OCOC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 NWZGGBGILYYNSW-UHFFFAOYSA-N 0.000 claims description 4
- KGYVCBDKYJUXOY-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1-methylindole-7-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC3=CC(Cl)=CC=C3NS(=O)(=O)C=3C=CC=C4C=CN(C=34)C)=CC2=C1 KGYVCBDKYJUXOY-UHFFFAOYSA-N 0.000 claims description 4
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- WESDUBCJHVEYPE-UHFFFAOYSA-N n-[5-chloro-2-[[3-(difluoromethoxy)phenyl]sulfonylamino]phenyl]-1-benzofuran-2-sulfonamide Chemical compound FC(F)OC1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 WESDUBCJHVEYPE-UHFFFAOYSA-N 0.000 claims description 4
- HEMUZZBQYAMWEF-UHFFFAOYSA-N n-[5-chloro-2-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]-4-methylphenyl]pyridine-3-sulfonamide Chemical compound C=1C=CN=CC=1S(=O)(=O)NC=1C=C(Cl)C(C)=CC=1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 HEMUZZBQYAMWEF-UHFFFAOYSA-N 0.000 claims description 4
- VKMYLBVLRDKLPV-UHFFFAOYSA-N n-[5-chloro-2-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]-4-methylphenyl]thiophene-2-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC=1C=C(Cl)C(C)=CC=1NS(=O)(=O)C1=CC=C(Cl)C(C(F)(F)F)=C1 VKMYLBVLRDKLPV-UHFFFAOYSA-N 0.000 claims description 4
- TVRMYGUDTAPIQJ-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]pyrrole-3-sulfonamide Chemical compound C=1C2=CC=CC=C2OC=1S(=O)(=O)NC1=CC(Cl)=CC=C1NS(=O)(=O)C(=C1)C=CN1S(=O)(=O)C1=CC=CC=C1 TVRMYGUDTAPIQJ-UHFFFAOYSA-N 0.000 claims description 3
- KZXIZVGZXQJCRM-UHFFFAOYSA-N 1-(benzenesulfonyl)-n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]pyrrole-3-sulfonamide Chemical compound C=1C=CSC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C(=C1)C=CN1S(=O)(=O)C1=CC=CC=C1 KZXIZVGZXQJCRM-UHFFFAOYSA-N 0.000 claims description 3
- LEVYJBYXMDTUNR-UHFFFAOYSA-N 1-[3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-ethoxyphenyl]-3-methylurea Chemical compound CCOC1=CC=C(NC(=O)NC)C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 LEVYJBYXMDTUNR-UHFFFAOYSA-N 0.000 claims description 3
- XJWDAZMVMTUUJO-UHFFFAOYSA-N 2,4-dichloro-5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1Cl XJWDAZMVMTUUJO-UHFFFAOYSA-N 0.000 claims description 3
- WFQIMFQFEWNBOY-UHFFFAOYSA-N 2-chloro-5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]benzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 WFQIMFQFEWNBOY-UHFFFAOYSA-N 0.000 claims description 3
- UGAPDINNAHKRAD-UHFFFAOYSA-N 2-chloro-n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1,3-benzothiazole-6-sulfonamide Chemical compound C1=C2SC(Cl)=NC2=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 UGAPDINNAHKRAD-UHFFFAOYSA-N 0.000 claims description 3
- CTTDUEYVVPQPTE-UHFFFAOYSA-N 2h-1,2-benzoxazine-4-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CNOC2=C1 CTTDUEYVVPQPTE-UHFFFAOYSA-N 0.000 claims description 3
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims description 3
- VTSVMLKGQJFYPF-UHFFFAOYSA-N 3-[4-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]phenyl]propanoic acid Chemical compound C1=CC(CCC(=O)O)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 VTSVMLKGQJFYPF-UHFFFAOYSA-N 0.000 claims description 3
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- APJIHDUAUJENTJ-UHFFFAOYSA-N 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 APJIHDUAUJENTJ-UHFFFAOYSA-N 0.000 claims description 3
- QHEKGWAEXQORSV-UHFFFAOYSA-N 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 QHEKGWAEXQORSV-UHFFFAOYSA-N 0.000 claims description 3
- IYRLUGKFRHTATI-UHFFFAOYSA-N 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 IYRLUGKFRHTATI-UHFFFAOYSA-N 0.000 claims description 3
- QTWZJVYTJKDRRP-UHFFFAOYSA-N 3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 QTWZJVYTJKDRRP-UHFFFAOYSA-N 0.000 claims description 3
- PHXFSYXUATWGBF-UHFFFAOYSA-N 3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 PHXFSYXUATWGBF-UHFFFAOYSA-N 0.000 claims description 3
- QFMBMRRZDJVWNE-UHFFFAOYSA-N 3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 QFMBMRRZDJVWNE-UHFFFAOYSA-N 0.000 claims description 3
- NTGVFVPBHYDYPT-UHFFFAOYSA-N 3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 NTGVFVPBHYDYPT-UHFFFAOYSA-N 0.000 claims description 3
- QBCRIUZZUDWNNQ-UHFFFAOYSA-N 4-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 QBCRIUZZUDWNNQ-UHFFFAOYSA-N 0.000 claims description 3
- NIFHAXQONVAFAH-UHFFFAOYSA-N 4-chloro-3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]benzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 NIFHAXQONVAFAH-UHFFFAOYSA-N 0.000 claims description 3
- VQGQVYHPZKXTSC-UHFFFAOYSA-N 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-chloro-4-fluorobenzoic acid Chemical compound C1=C(Cl)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1F VQGQVYHPZKXTSC-UHFFFAOYSA-N 0.000 claims description 3
- UVYYWYNAAGFPLT-UHFFFAOYSA-N 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 UVYYWYNAAGFPLT-UHFFFAOYSA-N 0.000 claims description 3
- DYSBRZHRXVEXNH-UHFFFAOYSA-N 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 DYSBRZHRXVEXNH-UHFFFAOYSA-N 0.000 claims description 3
- JRVMXJUHEVSQOL-UHFFFAOYSA-N 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 JRVMXJUHEVSQOL-UHFFFAOYSA-N 0.000 claims description 3
- JKCKFNZNRLITPB-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-(methylamino)benzoic acid Chemical compound C1=C(C(O)=O)C(NC)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 JKCKFNZNRLITPB-UHFFFAOYSA-N 0.000 claims description 3
- SZDBUEUDQKTVOM-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-ethoxybenzoic acid Chemical compound C1=C(C(O)=O)C(OCC)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 SZDBUEUDQKTVOM-UHFFFAOYSA-N 0.000 claims description 3
- FEPHUAJNJFZAKM-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-fluorobenzoic acid Chemical compound C1=C(F)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 FEPHUAJNJFZAKM-UHFFFAOYSA-N 0.000 claims description 3
- PUARYRGFSYWWHX-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-hydroxybenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 PUARYRGFSYWWHX-UHFFFAOYSA-N 0.000 claims description 3
- LUDALJFKOACNHW-UHFFFAOYSA-N 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-methylbenzoic acid Chemical compound C1=C(C(O)=O)C(C)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 LUDALJFKOACNHW-UHFFFAOYSA-N 0.000 claims description 3
- QVZMGTPXSQIGDA-UHFFFAOYSA-N 5-chloro-n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1,3-dimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(Cl)=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 QVZMGTPXSQIGDA-UHFFFAOYSA-N 0.000 claims description 3
- CREPABVSBRHFGB-UHFFFAOYSA-N 5-chloro-n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-3-methyl-1-benzothiophene-2-sulfonamide Chemical compound S1C2=CC=C(Cl)C=C2C(C)=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 CREPABVSBRHFGB-UHFFFAOYSA-N 0.000 claims description 3
- 239000005711 Benzoic acid Substances 0.000 claims description 3
- PGBFYLVIMDQYMS-UHFFFAOYSA-N Methyl thiophene-2-carboxylate Chemical compound COC(=O)C1=CC=CS1 PGBFYLVIMDQYMS-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 3
- ZKULDADLTIZFIF-UHFFFAOYSA-N ethyl 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]furan-3-carboxylate Chemical compound CCOC(=O)C1=COC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 ZKULDADLTIZFIF-UHFFFAOYSA-N 0.000 claims description 3
- CBUIBEAFEGOPMO-UHFFFAOYSA-N methyl 2-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 CBUIBEAFEGOPMO-UHFFFAOYSA-N 0.000 claims description 3
- MPNXYSYDIDMIFV-UHFFFAOYSA-N methyl 2-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 MPNXYSYDIDMIFV-UHFFFAOYSA-N 0.000 claims description 3
- SNBCBUUDHNCVIH-UHFFFAOYSA-N methyl 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-methylbenzoate Chemical compound COC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1C SNBCBUUDHNCVIH-UHFFFAOYSA-N 0.000 claims description 3
- LKNPPFRESLCCMC-UHFFFAOYSA-N methyl 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 LKNPPFRESLCCMC-UHFFFAOYSA-N 0.000 claims description 3
- UJIOMJIQDGSEAW-UHFFFAOYSA-N methyl 3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-5-chlorothiophene-2-carboxylate Chemical compound S1C(Cl)=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1C(=O)OC UJIOMJIQDGSEAW-UHFFFAOYSA-N 0.000 claims description 3
- XXMBLAXWOMFZQE-UHFFFAOYSA-N methyl 3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-methylbenzoate Chemical compound COC(=O)C1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1C XXMBLAXWOMFZQE-UHFFFAOYSA-N 0.000 claims description 3
- NNFZDMYLIQIYOU-UHFFFAOYSA-N methyl 3-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-methoxybenzoate Chemical compound COC(=O)C1=CC=C(OC)C(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 NNFZDMYLIQIYOU-UHFFFAOYSA-N 0.000 claims description 3
- RQRWBKQQLOSBPA-UHFFFAOYSA-N methyl 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-1-methylpyrrole-2-carboxylate Chemical compound CN1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 RQRWBKQQLOSBPA-UHFFFAOYSA-N 0.000 claims description 3
- LDYVRSKVHNTKDM-UHFFFAOYSA-N methyl 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-methylbenzoate Chemical compound C1=C(C)C(C(=O)OC)=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 LDYVRSKVHNTKDM-UHFFFAOYSA-N 0.000 claims description 3
- MTLLFOKMWLBBKP-UHFFFAOYSA-N methyl 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-2-methylfuran-3-carboxylate Chemical compound O1C(C)=C(C(=O)OC)C=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 MTLLFOKMWLBBKP-UHFFFAOYSA-N 0.000 claims description 3
- JUHGLWCGZNQKIJ-UHFFFAOYSA-N methyl 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]-4-methoxythiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1OC JUHGLWCGZNQKIJ-UHFFFAOYSA-N 0.000 claims description 3
- ITLHPRKURFWWBL-UHFFFAOYSA-N methyl 5-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 ITLHPRKURFWWBL-UHFFFAOYSA-N 0.000 claims description 3
- BRUIHUWZLQFXCW-UHFFFAOYSA-N methyl 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-methylfuran-3-carboxylate Chemical compound O1C(C)=C(C(=O)OC)C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 BRUIHUWZLQFXCW-UHFFFAOYSA-N 0.000 claims description 3
- QFQLZKVKBFBGLH-UHFFFAOYSA-N methyl 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-4-methoxythiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1OC QFQLZKVKBFBGLH-UHFFFAOYSA-N 0.000 claims description 3
- UEVWXDAKIXRXMW-UHFFFAOYSA-N methyl 5-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]furan-2-carboxylate Chemical compound O1C(C(=O)OC)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 UEVWXDAKIXRXMW-UHFFFAOYSA-N 0.000 claims description 3
- ARMPQNNQZSHCGU-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1,2-dimethylimidazole-4-sulfonamide Chemical compound CN1C(C)=NC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 ARMPQNNQZSHCGU-UHFFFAOYSA-N 0.000 claims description 3
- FYGLABRUSQKJLH-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1,3,5-trimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(C)=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 FYGLABRUSQKJLH-UHFFFAOYSA-N 0.000 claims description 3
- HQIZGSCMBOBBRA-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1,3-benzothiazole-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5SC=NC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 HQIZGSCMBOBBRA-UHFFFAOYSA-N 0.000 claims description 3
- PPAPVJRRXCNAHG-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1-methylindole-4-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC3=CC(Cl)=CC=C3NS(=O)(=O)C3=C4C=CN(C4=CC=C3)C)=CC2=C1 PPAPVJRRXCNAHG-UHFFFAOYSA-N 0.000 claims description 3
- XXAGDPBMNBTIMV-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-1h-1,2,4-triazole-5-sulfonamide Chemical compound C=1C2=CC=CC=C2OC=1S(=O)(=O)NC1=CC(Cl)=CC=C1NS(=O)(=O)C1=NC=NN1 XXAGDPBMNBTIMV-UHFFFAOYSA-N 0.000 claims description 3
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- SLZUBHPAARCGKL-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2,3-dihydro-1,4-benzodioxine-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5OCCOC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 SLZUBHPAARCGKL-UHFFFAOYSA-N 0.000 claims description 3
- HBBCBVUFBFBHFJ-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2,4-dimethyl-1,3-thiazole-5-sulfonamide Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)NC1=CC=C(Cl)C=C1NS(=O)(=O)C1=CC2=CC=CC=C2O1 HBBCBVUFBFBHFJ-UHFFFAOYSA-N 0.000 claims description 3
- CELQBZLOLDSVJT-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-chloro-1,3-benzothiazole-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC3=CC(Cl)=CC=C3NS(=O)(=O)C3=CC=C4N=C(SC4=C3)Cl)=CC2=C1 CELQBZLOLDSVJT-UHFFFAOYSA-N 0.000 claims description 3
- QQZQLWFWUWHZRZ-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-chloropyridine-3-sulfonamide Chemical compound C=1C2=CC=CC=C2OC=1S(=O)(=O)NC1=CC(Cl)=CC=C1NS(=O)(=O)C1=CC=CN=C1Cl QQZQLWFWUWHZRZ-UHFFFAOYSA-N 0.000 claims description 3
- QCGJGDJMBSAKHN-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-chloroquinoline-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5C=CC(Cl)=NC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 QCGJGDJMBSAKHN-UHFFFAOYSA-N 0.000 claims description 3
- RUTDKWOZOCUJLA-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-methyl-1,3-benzothiazole-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC3=CC(Cl)=CC=C3NS(=O)(=O)C3=CC=C4N=C(SC4=C3)C)=CC2=C1 RUTDKWOZOCUJLA-UHFFFAOYSA-N 0.000 claims description 3
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- QMQHYWXLDYYODL-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-oxo-1,3-dihydroindole-5-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5CC(=O)NC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 QMQHYWXLDYYODL-UHFFFAOYSA-N 0.000 claims description 3
- FALHJCHEJBNBTA-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5CCC(=O)NC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 FALHJCHEJBNBTA-UHFFFAOYSA-N 0.000 claims description 3
- FUYAJTMFFKRZJI-UHFFFAOYSA-N n-[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]-2-oxo-3h-1,3-benzothiazole-6-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5SC(=O)NC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 FUYAJTMFFKRZJI-UHFFFAOYSA-N 0.000 claims description 3
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- FELFPPQRNPOUDK-UHFFFAOYSA-N n-[3-[[2-(1-benzofuran-2-ylsulfonylamino)-4-chlorophenyl]sulfamoyl]phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(S(=O)(=O)NC=2C(=CC(Cl)=CC=2)NS(=O)(=O)C=2OC3=CC=CC=C3C=2)=C1 FELFPPQRNPOUDK-UHFFFAOYSA-N 0.000 claims description 3
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- KDFKLHUJHPUNAU-UHFFFAOYSA-N n-[4,5-dichloro-2-(2,3-dihydro-1h-inden-5-ylsulfonylamino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=C2CCCC2=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 KDFKLHUJHPUNAU-UHFFFAOYSA-N 0.000 claims description 3
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- ZHBNDNLSTKZEDR-UHFFFAOYSA-N n-[4,5-dichloro-2-(naphthalen-1-ylsulfonylamino)phenyl]thiophene-2-sulfonamide Chemical compound C=1C=CC2=CC=CC=C2C=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 ZHBNDNLSTKZEDR-UHFFFAOYSA-N 0.000 claims description 3
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- PYRYCAVGJJOBNT-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1,3,5-trimethylpyrazole-4-sulfonamide Chemical compound CC1=NN(C)C(C)=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 PYRYCAVGJJOBNT-UHFFFAOYSA-N 0.000 claims description 3
- VSNSBLQUBQKWSP-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1,3-benzodioxole-5-sulfonamide Chemical compound C=1C=C2OCOC2=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 VSNSBLQUBQKWSP-UHFFFAOYSA-N 0.000 claims description 3
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- JKQHIJHDRALSAD-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1-methylindole-4-sulfonamide Chemical compound C1=CC=C2N(C)C=CC2=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 JKQHIJHDRALSAD-UHFFFAOYSA-N 0.000 claims description 3
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- MAZDSHXLANAEJI-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-1h-1,2,4-triazole-5-sulfonamide Chemical compound N=1C=NNC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 MAZDSHXLANAEJI-UHFFFAOYSA-N 0.000 claims description 3
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- VWZHCXQCISNLJK-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-2,2-dimethyl-3,4-dihydrochromene-6-sulfonamide Chemical compound C=1C=C2OC(C)(C)CCC2=CC=1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 VWZHCXQCISNLJK-UHFFFAOYSA-N 0.000 claims description 3
- ZPSSIPVJQNDLPJ-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-2,3-dihydro-1-benzofuran-5-sulfonamide Chemical compound C=1C=C2OCCC2=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 ZPSSIPVJQNDLPJ-UHFFFAOYSA-N 0.000 claims description 3
- HOTACAHZZYBLHS-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-2,3-dioxo-1,4-dihydroquinoxaline-6-sulfonamide Chemical compound C=1C=C2NC(=O)C(=O)NC2=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 HOTACAHZZYBLHS-UHFFFAOYSA-N 0.000 claims description 3
- IYKXSVJMCDJDMK-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-2,4-dimethyl-1,3-thiazole-5-sulfonamide Chemical compound S1C(C)=NC(C)=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 IYKXSVJMCDJDMK-UHFFFAOYSA-N 0.000 claims description 3
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- LJMIPTDPGIQPMQ-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-2-oxo-3,4-dihydro-1h-quinoline-6-sulfonamide Chemical compound C=1C=C2NC(=O)CCC2=CC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 LJMIPTDPGIQPMQ-UHFFFAOYSA-N 0.000 claims description 3
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- PQSLWZZYXCODLS-UHFFFAOYSA-N n-[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]-5-(1,2-oxazol-5-yl)thiophene-2-sulfonamide Chemical compound C=1C=C(C=2ON=CC=2)SC=1S(=O)(=O)NC=1C=C(Cl)C(Cl)=CC=1NS(=O)(=O)C1=CC=CS1 PQSLWZZYXCODLS-UHFFFAOYSA-N 0.000 claims description 3
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- LDHHTRNOGZVGNI-UHFFFAOYSA-N n-[4,5-dichloro-2-[[2-(trifluoromethoxy)phenyl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 LDHHTRNOGZVGNI-UHFFFAOYSA-N 0.000 claims description 3
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- WULUTWZWVRVHCQ-UHFFFAOYSA-N n-[4,5-dichloro-2-[[3-(6-methylpyrazin-2-yl)oxyphenyl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound CC1=CN=CC(OC=2C=C(C=CC=2)S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=N1 WULUTWZWVRVHCQ-UHFFFAOYSA-N 0.000 claims description 3
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- ZKYDJUXQXNXGFU-UHFFFAOYSA-N n-[4,5-dichloro-2-[[4-chloro-3-(trifluoromethyl)phenyl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound C1=C(Cl)C(C(F)(F)F)=CC(S(=O)(=O)NC=2C(=CC(Cl)=C(Cl)C=2)NS(=O)(=O)C=2SC=CC=2)=C1 ZKYDJUXQXNXGFU-UHFFFAOYSA-N 0.000 claims description 3
- WDPRDRGFPIMDEP-UHFFFAOYSA-N n-[4,5-dichloro-2-[[6-(dimethylamino)naphthalen-2-yl]sulfonylamino]phenyl]thiophene-2-sulfonamide Chemical compound C1=CC2=CC(N(C)C)=CC=C2C=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 WDPRDRGFPIMDEP-UHFFFAOYSA-N 0.000 claims description 3
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- FQLNQJZUXVXJLN-UHFFFAOYSA-N n-[4-[[4,5-dichloro-2-(thiophen-2-ylsulfonylamino)phenyl]sulfamoyl]-2-methylphenyl]acetamide Chemical compound C1=C(C)C(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC(Cl)=C(Cl)C=C1NS(=O)(=O)C1=CC=CS1 FQLNQJZUXVXJLN-UHFFFAOYSA-N 0.000 claims description 3
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- URSPRUZXWUHFGK-UHFFFAOYSA-N n-[5-chloro-2-(2,3-dihydro-1-benzofuran-5-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5CCOC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 URSPRUZXWUHFGK-UHFFFAOYSA-N 0.000 claims description 3
- CDZLQMUGNCHNNB-UHFFFAOYSA-N n-[5-chloro-2-(2,3-dihydro-1h-inden-5-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5CCCC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 CDZLQMUGNCHNNB-UHFFFAOYSA-N 0.000 claims description 3
- GRGNZPVHUBHGEA-UHFFFAOYSA-N n-[5-chloro-2-(5,6,7,8-tetrahydronaphthalen-2-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5CCCCC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 GRGNZPVHUBHGEA-UHFFFAOYSA-N 0.000 claims description 3
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- NHRYAUGSCCSATD-UHFFFAOYSA-N n-[5-chloro-2-(naphthalen-1-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C5=CC=CC=C5C=CC=4)=CC=C(C=3)Cl)=CC2=C1 NHRYAUGSCCSATD-UHFFFAOYSA-N 0.000 claims description 3
- OPDJAHBAAPKUMM-UHFFFAOYSA-N n-[5-chloro-2-(naphthalen-2-ylsulfonylamino)phenyl]-1-benzofuran-2-sulfonamide Chemical compound C1=CC=C2OC(S(=O)(=O)NC=3C(NS(=O)(=O)C=4C=C5C=CC=CC5=CC=4)=CC=C(C=3)Cl)=CC2=C1 OPDJAHBAAPKUMM-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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Abstract
본 발명은 신규한 비스-설폰아마이드 유도체들, 이들을 제조하는 방법, 이들을 함유하는 약제학적 조성물 및 케모카인 수용체의 조절제로서의 약제로서의 그들의 용도에 관한 것이다.
Description
관련 출원
본 출원은 미국 특허 가출원 제61/423,941호(출원일: 2010년 12월 16일)의 이득을 주장하며, 이 기초 출원의 개시내용은 그의 전문이 본 명세서에 참조로 병합된다.
발명의 기술분야
본 발명은 신규한 1,2-비스-설폰아마이드 유도체들, 이들을 제조하는 방법, 이들을 함유하는 약제학적 조성물 및 케모카인 수용체의 조절제로서의 이들의 용도에 관한 것이다. 본 발명은 구체적으로는 이들 화합물의 용도 및 케모카인 수용체(chemokine receptor: CCR) 조절과 관련된 장애를 치료하는 이들의 약제학적 용도에 관한 것이다.
케모카인류는 염증 동안 백혈구 동원 및 이동을 조정하는데 중요한 역할을 하는 7- 내지 14-kd 펩타이드의 군이므로, 항염증 요법을 위한 중요한 표적을 나타낸다(Wells et al., 2006). 이들은 7-막관통, G 단백질-결합된 수용체인 케모카인 수용체에 결합함으로써 작용한다. 케모카인 시스템은 복잡하며, 약 ~50개의 케모카인과 20개의 케모카인 수용체가 인간에서 확인되었고, 이들은 종종 용장적으로 작용하여, 특정 길항제의 선택을 어렵게 만든다(Gerard and Rollins, 2001). 유전적 넉아웃 전략이 면역 기능의 조정제로서 케모카인의 중요성을 확인하였지만, 특정 케모카인의 결여는 면역 반응에서 단지 특유의 비교적 온화한 결함을 초래하여 상기 시스템의 복잡한 용장성을 더욱 강조한다. 선택성은, 면역 기능에 대해서 미묘하고 특이적인 제어를 가능하게 하기 위하여 대식세포/단핵 시스템이 주된 기능자인 죽상동맥경화증 등에 단일의 케모카인-수용체 시스템이 연루되어 있는 전신 질환에서의 케모카인 수용체 길항제의 이용을 위하여 중요하다(Weisberg et al., 2006; Feria and Diaz Gonzalez et al., 2006).
많은 안구 병태는 안구 구조에 대한 유해 효과를 가진 채 안구 내로 백혈구 및 내피 세포 등의 세포의 부적절한 이동과 침윤을 특징으로 한다(Wallace et al., 2004). 케모카인은 이러한 질환에서 확인된 바 있고, 케모카인 시스템의 잘못된 조절은 각막 이식편 거부, 당뇨 망막병증, 연령 관련 황반 변성(age-related macular degeneration: ARMD), 만성 염증 질환, 예컨대, 포도막염, 안구 건조 등에서 명확하다. CCR2 혹은 MCP-1을 결여하는 마우스는 이 케모카인 및 그의 수용체 신호전달에서 결정적인 역할을 나타내는 광수용체 위축, 맥락막 혈관신생 및 드루젠 침전물(drusen deposit)을 포함하는 연령에 따른 ARMD의 특성을 전개시킨다(Amabati et al., 2003). 이와 같이 해서, CCR2 수용체-특이적 억제제는 ARMD와 같은 안구 질환에서 잠재적인 치료 이득을 지닐 수 있다. 이에 대해서, 다양한 인간 및 동물 연구는, 상주 및 침윤 세포 둘 모두에 의해 생성되는 상이한 형태의 포도막염에서 수개의 케모카인을 확인한 바 있으며, 이는 그의 발병에서 이들 분자에 대한 두드러진 역할을 강력하게 시사하고 있다. 포도막염의 래트 및 마우스 모델의 연구는, 단핵 및 T-세포에 대해서 강력한 화학주성인자인 단핵 화학주성인자 단백질-1(monocyte chemoattractant protein-1: MCP-1), 대식세포 염증 단백질-1(macrophage inflammatory protein-1: MIP-1), RANTES, 기질 유래 인자-1(stromal derived factor-1: SDF-1)의 상향 조절을 입증하고 있다(Fang et al., 2004; Keino et al., 2003). 유사한 결과가 인간 포도막염의 가장 흔한 형태인 급성 전방 포도막염(acute anterior uveitis: AAU)을 가진 환자의 말초 단핵 세포에서 보고된 바 있다(Klitgaard et al., 2004). MCP-1 넉아웃 마우스 및 CCR5 넉아웃 마우스는 저감된 내독소-유발 포도막염을 보이며, 이는 AAU에 대한 동물 모델이다(Takeuchi et al., 2005; Tuallion et al., 2002). 또한, NF-κB 블로커의 사용으로 업스트림의 케모카인 시스템을 차단하는 것은 래트에서 실험적 AAU를 유의하게 감소시키는 것이 입증되었다(Yang et al., 2005). NF-κB의 봉쇄는 다수의 케모카인의 전사 억제를 초래한다. 포도막염의 발병의 복잡성을 고려해볼 때, 단일요법에서의 케모카인 수용체의 선택적 억제가 치료 유익을 제공할 것으로 생각되지 않는다. 다수의 케모카인의 유사한 역할은 당뇨 망막병증 및 안구 건조에서의 질환의 임상적 단계와 상관이 있는 것을 나타내었다(Meleth et al., 2005; Yamagami et al., 2005). 이들 안구 질환에서, 광범위한 케모카인의 기능을 억제하는 광범위 케모카인 수용체 억제제의 이용은 유익할 수 있다.
보고된 1차 광범위 케모카인 억제제(broad spectrum chemokine inhibitor: BSCI)는 펩타이드 3이라고 지칭되며, 이는 인간 케모카인 MCP-1의 서열로부터 유래되어 MCP-1, MIP-1, RANTES 및 SDF-1에 반응하여 단핵의 이동을 차단하는 것으로 판명되었다(Reckless and Grainger. 1999). NR58-3.14.3이라고 불리는, 역순 서열의 D-아미노산으로 구성된 펩타이드 3의 환식 레트로 역전 유사체는, 더욱 강력한 케모카인 억제제인 것으로 관찰되었다(Beech et al., 2001). NR58-3.14.3은 죽상 동맥 경화증, 폐 염증, 과민성 대장 증후군 등의 동물 모델에서 항염증 활성을 위한 테스트에 이용되었다(Beech et al., 2001; Grainger and Reckless. 2003; Tokuyama et al., 2005). 그러나, 이들 BSCI를 장기 치료 전략으로서 이용하는 데는 몇가지 단점이 있다. 비교적 낮은 효능, 불량한 약동학을 지니는 펩타이드인 공지된 BSCI는 생체내에서 불안정하다. 또한, 광범위 케모카인 수용체 억제제의 전신 사용은 그들의 전신의 항염증 활성으로 인해 유해한 부작용으로 잠재적으로 초래할 수 있었다. 그러나, 안구 질환에 있어서, 국부 혹은 국소 적용은 광범위 억제제를 전신에 흡수시키는 것을 방지하였다. 수 개의 케모카인 수용체의 소분자 억제제의 식별은 염증 안구 질환의 치료를 위하여 매우 유용할 수 있었다. 몇 가지 안구 질환에서의 다수의 케모카인의 역할 및 이들 결과에 대한 증거를 고려할 때, 본 발명자들은, 소 및 대 분자 광범위 케모카인 수용체 억제제의 이용이 포도막염, 안구 건조, 당뇨 망막병증, 알레르기성 안 질환 및 증식성 망막증을 포함하지만 이들로 제한되는 것은 아닌 안구 염증 질환의 국소 치료에서의 유용성을 지닐 것을 제안하고 있다. 따라서, 다수의 케모카인의 조정은 안구 질환을 치료하는데 있어서 신규한 치료적 접근법을 나타낸다.
국제 특허 공개 제WO 2001028537호 공보는 데하이드로퀴네이트 신타제 및 제II형 데하이드로퀴나제 효소의 억제제로서의 설폰아마이드 유도체의 제법을 개시하고 있다. 화합물인 N,N'-(4-클로로-1,2-페닐렌)비스-2-티오펜설폰아마이드(CAS 335336-21-5) 및 N,N'-(4-클로로-5-메틸-1,2-페닐렌)비스-)2-티오펜설폰아마이드(CAS 335335-03-0)가 국제 특허 공개 제WO 2001028537호 공보에 개시되어 있다.
국제 특허 공개 제WO 2006047302호 공보는 GalR1의 작용제로서의 비스-설폰아마이드 화합물, 그의 제법, 약제학적 조성물 및 치료에서의 용도를 개시하고 있다. 화합물인 N,N'-(1,2-페닐렌비스-)-2-벤조퓨란설폰아마이드(CAS 885052-53-9) 및 N-[2-[[(4-클로로페닐)설포닐]페닐]-2-벤조퓨란설폰아마이드(CAS 885052-31-3)가 국제 특허 공개 제WO 2006047302호 공보에 개시되어 있다.
미국 특허 제7622583호 공보는 CCR2 수용체의 길항제로서 헤테로아릴 설폰아마이드를 개시하고 있다.
미국 특허 공개 제2008/0293720호 공보는 케모카인 수용체의 피리디닐 설폰아마이드 조절제를 개시하고 있다.
국제 특허 공개 제WO2005004810호 공보는 브라디키닌 B1 길항제 혹은 역 작용제로서의 아릴설폰아마이드 유도체를 개시하고 있다.
국제 특허 공개 제WO03/099773호 공보는 CCR9 억제제 및 그의 이용 방법을 개시하고 있다.
국제 특허 공개 제WO2008008374호 공보는 CCR2 억제제 및 그의 이용 방법을 개시하고 있다.
강력하고 선택적인 케모카인 수용체 조절제인 신규한 1,2-비스-설폰아마이드 유도체의 군이 발견되었다. 이와 같이, 본 명세서에 기재된 화합물은 케모카인 수용체의 조절과 관련된 광범위한 장애를 치료하는데 유용하다. 본 명세서에서 이용되는 바와 같은 "조절제"란 용어는 수용체 작용제, 길항제, 역 작용제, 역 길항제, 부분 작용제, 부분 길항제를 포함하지만, 이들로 제한되는 것은 아니다.
본 발명은 케모카인 수용체 생물학적 활성을 지니는 화학식 I의 화합물을 기재한다. 본 발명에 따른 화합물은, 이와 같이 해서 약물에서, 예를 들어, CCR 조절에 의해 완화되는 질환 및 병태를 지니는 인간의 치료에서 이용된다.
일 양상에 있어서, 본 발명은 하기 화학식 I을 지닌 화합물 또는 그의 약제학적으로 허용가능한 염 또는 그의 입체이성질체 형태, 또는 개별의 기하 이성질체, 거울상이성질체, 부분입체이성질체, 호변이성질체, 쯔비터이온(zwitterion) 및 그의 약제학적으로 허용가능한 염을 제공한다:
[화학식 I]
식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 N 또는 C-R7이고;
R4는 N 또는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-벤조퓨란, 2-티에닐, 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐, 4-클로로-3-메틸페닐 또는 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 N 또는 C-R16이고;
R17은 N 또는 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-6 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-6 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-6 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R19, NR20R21 또는 하이드록실이고;
R18은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-6 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R22, NR23R24 또는 하이드록실이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
이하의 화합물들;
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드; 및
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-쿼텟아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않으며;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소원자가 아니며;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-벤조퓨란, 2-티에닐, 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐, 4-클로로-3-메틸페닐 또는 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R19, NR20R21 또는 하이드록실이고;
R18은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R22, NR23R24 또는 하이드록실이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드; 및
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니고;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 N 또는 C-R7이고;
R4는 N 또는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-벤조퓨란, 2-티에닐, 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐, 4-클로로-3-메틸페닐 또는 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 N 또는 C-R16이고;
R17은 N이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R19, NR20R21 또는 하이드록실이고;
R18은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R22, NR23R24 또는 하이드록실이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니고;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 페닐이고;
R6은 2-벤조퓨란, 2-티에닐, 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐, 4-클로로-3-메틸페닐 또는 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H이고
R18은 H이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니고;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 페닐이고;
R6은 2-벤조퓨란이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H이고;
R18은 H이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-티에닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H이고;
R18은 H이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니다.
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H이고;
R18은 H이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
d). 상기 화합물은 이하의 구조가 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐 또는 4-클로로-3-메틸페닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R9, NR10R11 또는 하이드록실이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬, 할로겐, -OC1-3 알킬, CN, C 2-6 알케닐, C 2-6 알키닐, C(O)R12, NR13R14 또는 하이드록실이며;
R16은 H이고;
R18은 H이며;
R9는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R10은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R11은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R12는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R13은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R14는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R19는 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R20은 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R21은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R22는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R23은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R24는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-벤조퓨란, 2-티에닐, 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐, 4-클로로-3-메틸페닐 또는 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬이며;
R16은 H이고;
R18은 H이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니며;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-벤조퓨란이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬이며;
R16은 H이고;
R18은 H이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 2-티에닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬이며;
R16은 H이고;
R18은 H이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함하되;
단,
a) R6은 R5와 동일하지 않고;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니다.
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H 또는 치환 혹은 비치환된 C1-6 알킬이고;
R2는 H 또는 치환 혹은 비치환된 C1-6 알킬이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 치환 혹은 비치환된 C1-6 알킬, 치환 혹은 비치환된 헤테로사이클, 치환 혹은 비치환된 C3-8 사이클로알킬, 치환 혹은 비치환된 C3-8 사이클로알케닐이거나 또는 치환 혹은 비치환된 C6-10 아릴이고;
R6은 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 C-R16이고;
R17은 C-R18이며;
R7은 H, 치환 혹은 비치환된 C1-6 알킬이고;
R8은 H, 치환 혹은 비치환된 C1-6 알킬이며;
R16은 H이고;
R18은 H이며;
이하의 화합물들:
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드를 포함함되;
단,
a). R6은 R5와 동일하지 않고;
d). 상기 화합물은 이하의 구조들이 아니다:
다른 양상에 있어서, 본 발명은 화학식 I을 지닌 화합물을 제공하되, 식 중,
R1은 H이고;
R2는 H이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 2-티에닐, 페닐, 페닐-4-아세트아마이드, 4-클로로-3-트라이플루오로메틸페닐, -1-메틸-1H-이미다졸, 3-피리딘, 2 아미노페닐, 1,3-다이메틸-1H-피라졸, 1-메틸-1H-피라졸, 1-메틸-1H-이미다졸, 4-(1H-피라졸-1-일)페닐, 1,3-티아졸-4-일)페닐, 4-(1,3-옥사졸-5-일)페닐, 2-(메틸아미노)벤조에이트, 1-메틸-1H-인돌, 2-옥소인돌린, 1-메틸-2,3-다이옥소인돌린, 1-메틸-2-옥소인돌린, 2-퓨란, 4-바이페닐, 3,5-다이플루오로페닐, 3,5-다이클로로페닐, -3,5-다이메틸아이소옥사졸, 4-클로로-2,5-다이플루오로페닐, 4-(2-메틸페녹시)페닐, 5-아이소옥사졸-3-일티오펜, 2,6-다이클로로페닐, 4-(메틸설포닐)페닐, 3,4-다이플루오로페닐, 4-클로로-3-메틸페닐, 2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸, 4-벤조산, 2-메톡시벤조산, 3-사이아노페닐, 4-tert-뷰틸페닐, 1,3-벤조티아졸, 1H-1,2,4-트라이아졸, 2-클로로-1,3-벤조티아졸, 2,4-다이메톡시페닐, 2,5-다이클로로-3-티에닐, 3-메톡시페닐, 3-(메틸설포닐)페닐, 3-클로로-2-메틸페닐, 4페닐프로판산, 2-에톡시벤조산, 2-메틸페닐}아세트아마이드, 3,5-비스(트라이플루오로메틸)페닐, 1H-피라졸, 4-(트라이플루오로메톡시)페닐, 4-(벤질옥시)페닐, 2-클로로-4-플루오로벤조산, 티오펜-2-카복실레이트, 4-플루오로벤조산, 2-클로로-퀴놀린, 2,3-다이하이드로-1H-인덴, 1-나프틸, 1,3-벤조다이옥솔, 3,5-다이클로로-2-하이드록시페닐, 2-벤조퓨란, 퀴놀린, 4-메틸벤조에이트, 2,4-다이메틸-1,3-티아졸, 4-메틸-1,3-티아졸-2-일}아세트아마이드, 5-클로로-8-퀴놀린, 2,4,5-트라이플루오로페닐, 3,4-다이메톡시페닐, 3,5-다이메틸-1H-피라졸, 1-(페닐설포닐)-1H-피롤, N-아세틸인돌린, 1,3,4-옥사아디아졸-2-일-페닐, 3-(1-메틸-1H-피라졸-3-일)페닐, 2-티에닐설포닐)아미노]페닐-4-메틸, 2-옥소-2H-크로멘, 6-페닐-3-피리딘, 2-클로로-4-(트라이플루오로메틸)페닐, 6-페녹시피리딘, 5-페닐티오펜, 2,5-다이메틸-3-티에닐, 2-클로로페닐-4-아세트아마이드, (5-클로로-2,4-다이플루오로페닐, 4-(1-메틸-1H-피라졸-3-일)페닐, 5-메틸-1-벤조티오펜, 2,5-다이메틸퓨란, 4-(피롤리딘-1-일설포닐)페닐, 메틸-2-메틸-3-퓨로에이트, 3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진, 2,4-다이클로로-벤조산, 5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐, 2-메톡시페닐}아세트아마이드, 2-이미다조[2,1-b][1,3]티아졸, 6-몰폴린-4-일피리딘, 3-[(6-메틸피라진-2-일)옥시]페닐, 5-피리딘-2-일티오펜, 3-피리미딘-2-일페닐, 4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진, 6-(다이메틸아미노)-2-나프틸, 2-(메틸설포닐)페닐, 3-메틸-8-퀴놀린, 5-아이소옥사졸-5-일티오펜, 5-(다이메틸아미노)-1-나프틸, 2-클로로-티에닐, 메틸, 에틸, 벤질, 아이소-뷰틸, 2,2-다이메틸크로만, 2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀, 4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진, 4-아세틸-3,4-다이하이드로-2H-1,4-벤즈옥사진, 4-(벤질옥시)페닐, 2,4-다이메틸-1,3-티아졸, 3,5-다이메틸아이소옥사졸, 5-클로로-3-메틸-1-벤조티엔-2-일, 2-클로로-4-플루오로벤조산, 4-메틸-1,3-티아졸-2-일}아세트아마이드, 1H-1,2,4-트라이아졸, 페닐}프로판산, 5-클로로티오펜-2-카복실레이트, 3-페닐아세트아마이드, 2-옥소인돌린, 2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸, 5-아이소옥사졸-3-일-2-티에닐, 2-클로로퀴놀린, 1-(페닐설포닐)-1H-피롤, 2,5-다이클로로-3-티에닐, 5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐, 6-몰폴린-4-일피리딘, 4-메톡시티오펜, 3-퓨릴, 1-메틸-1H-피라졸, 6-클로로이미다조[2,1-b][1,3]티아졸, 3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐, 3-피리미딘-2-일페닐, 1-아세틸-인돌린, 아이소니코티네이트, 3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐, 4-(3,5-다이메틸-1H-피라졸-1-일)페닐, 3,5-다이메틸-1-페닐-1H-피라졸, 4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진, 3,4-다이하이드로-2H-1,5-벤조다이옥세핀, 2,2-다이메틸크로만, 4-메틸-2-페닐-1,3-티아졸, 5-피리딘-2-일-2-티에닐, 4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진, 3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진, 5,6-다이클로로-3-피리딘, 2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린 또는 4-아세틸-3,4-다이하이드로-2H-1,4-벤즈옥사진이고;
R6은 2-벤조퓨란 또는 2-티에닐이며;
R15는 C-R16이고;
R17은 N 또는 C-R18이며;
R7은 H, 메틸 또는 염소이고;
R8은 H 또는 염소이며;
R16은 H이고;
R18은 H이되;
단,
a) R6은 R5와 동일하지 않으며;
b). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니다.
본 명세서에 이용되는 바와 같은 "알킬"이란 용어는 직쇄형 또는 분지쇄형 모이어티들 또는 그들의 조합을 갖고 1 내지 6개의 탄소 원자를 함유하는 포화된 1가 또는 2가의 탄화수소 모이어티를 지칭한다. 알킬 중의 하나의 메틸렌(-CH2-)기는 산소, 황, 설폭사이드, 질소, 카보닐, 카복실, 설포닐에 의해, 또는 2가의 C3-6 사이클로알킬에 의해 치환될 수 있다. 알킬기 상의 수소 원자는 할로겐, -OH, C 3-8 사이클로알킬, 비방향족 헤테로사이클, 방향족 헤테로사이클, -OC1-6 알킬, -NH2, -NO2, 아마이드, 에터, 에스터, 알데하이드, 케톤, 설폰아마이드기, 아릴, 카복실산, 및 에스터와 아마이드의 유도체, 포스폰산기, 설폰산기, 인산기 등을 포함하지만, 이들로 제한되는 것은 아닌 기에 의해 치환될 수 있다.
본 명세서에 이용되는 바와 같은 "사이클로알킬"이란 용어는, 포화 환식 탄화수소로부터 유래된 3 내지 12개의 탄소 원자의 1가 또는 2가의 기를 지칭한다. 사이클로알킬기는 단환식 혹은 다환식일 수 있다. 사이클로알킬은 할로겐, -OH, C 3-8 사이클로알킬, 비방향족 헤테로사이클, 방향족 헤테로사이클, -OC 1-6 알킬, -NH2, -NO2, 아마이드, 에터, 에스터, 알데하이드, 설폰아마이드기, 아릴, 카복실산 및 에스터와 아마이드의 유도체, 포스폰산기, 설폰산기, 인산기를 포함하지만, 이들로 제한되는 것은 아닌 기에 의해 치환될 수 있다.
명세서에서 이용되는 바와 같은 "사이클로알케닐"이란 용어는, 1개 이상의 이중 결합을 지니는 포화된 사이클로알킬로부터 유래된, 3 내지 12개의 탄소 원자의 1가 혹은 2가기를 지칭한다. 사이클로알케닐기는 단환식 혹은 다환식일 수 있다. 사이클로알케닐기는 할로겐, -OH, C 3-8 사이클로알킬, 비방향족 헤테로사이클, 방향족 헤테로사이클, -OC 1-6 알킬, -NH2, -NO2, 아마이드, 에터, 에스터, 알데하이드, 설폰아마이드기, 아릴, 카복실산 및 에스터와 아마이드의 유도체, 포스폰산기, 설폰산기, 인산기를 포함하지만, 이들로 제한되는 것은 아닌 기에 의해 치환될 수 있다. 명세서에서 이용되는 바와 같은 "할로겐"이란 용어는 염소, 브롬, 불소, 요오드의 원자를 지칭한다.
본 명세서에서 이용되는 바와 같은 "알케닐"이란 용어는, 포화 알킬로부터 유래된, 적어도 하나의 이중 결합을 가지는, 2 내지 6개의 탄소 원자를 지니는 1가 혹은 2가의 탄화수소 라디칼을 지칭한다. C 2-6 알케닐은 E 또는 Z 입체 배치일 수 있다. 알케닐기는 할로겐, -OH, C 3-8 사이클로알킬, 비방향족 헤테로사이클, 방향족 헤테로사이클, -OC 1-6 알킬, -NH2, -NO2, 아마이드, 에터, 에스터, 알데하이드, 설폰아마이드기, 아릴, 카복실산 및 에스터와 아마이드의 유도체, 포스폰산기, 설폰산기, 인산기를 포함하지만, 이들로 제한되는 것은 아닌 기에 의해 치환될 수 있다. 본 명세서에서 이용되는 바와 같은 "알키닐"이란 용어는 적어도 하나의 3중 결합을 지니는, 포화된 알킬로부터 유래된, 2 내지 6개의 탄소 원자를 지니는 1가 또는 2가의 탄화수소 라디칼을 지칭한다.
본 명세서에 이용되는 바와 같은 "헤테로사이클"이란 용어는, 탄소환 고리 구조를 중단(interrupting)시키는 O 혹은 N 혹은 S로부터 선택된 적어도 하나의 헤테로원자 또는 이들 중 적어도 2개의 조합을 함유하는, 방향족 혹은 비방향족, 포화 혹은 비포화되어 있을 수 있는 3 내지 12원(membered) 고리를 지칭한다. 헤테로사이클 고리는 C=O에 의해 중단될 수 있고; S 헤테로원자는 산화될 수 있다. 헤테로사이클은 단환식 혹은 다환식일 수 있다. 헤테로사이클 고리 모이어티는 할로겐, -OH, C 3-8 사이클로알킬, 비방향족 헤테로사이클, 방향족 헤테로사이클, -OC1-6 알킬, -NH2, -NO2, 아마이드, 에터, 에스터, 알데하이드, 케톤, 설폰아마이드기, 카복실산 및 에스터와 아마이드의 유도체, 포스폰산기, 설폰산기, 인산기를 포함하지만, 이들로 제한되는 것은 아닌 기에 의해 치환될 수 있다.
통상, 본 경우에, 헤테로사이클 고리는, 피리딘, 퓨란, 아제티딘, 티아졸, 티오펜, 옥사졸, 피라졸, 벤조퓨란, 아이소옥사졸, 2-옥소인돌린, 2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸, 2-옥소-2H-크로멘, 이미다졸[2,1-b]티아졸1-H-피라졸, 인돌, 이미다졸, 퀴놀린이다.
본 명세서에 이용되는 바와 같은 "아릴"이란 용어는, 6 내지 10개의 탄소 원자를 함유하는 고리로 이루어진 방향족 탄화수소로부터 유래된 유기 모이어티를 지칭한다. 1개의 수소의 제거에 의해, 아릴은 할로겐, -OH, C 3-8 사이클로알킬, 비방향족 헤테로사이클, 방향족 헤테로사이클, -OC1-6 알킬, -NH2, -NO2, 아마이드, 에터, 에스터, 알데하이드, 케톤, 설폰아마이드기, 아릴, 카복실산 및 에스터와 아마이드의 유도체, 포스폰산기, 설폰산기, 인산기를 포함하지만, 이들로 제한되는 것은 아닌 기에 의해 치환될 수 있다. 아릴은 단환식 또는 이환식일 수 있다.
본 명세서에서 이용되는 바와 같은 "케톤"이란 용어는, 식 "-C(O)Rx"의 기를 나타내되, 여기서 Rx는 C 1-6 알킬이다.
본 명세서에 이용되는 바와 같은 "하이드록실"이란 용어는 식 "-OH"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "아미노"란 용어는 식 "-NH2"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "카보닐"이란 용어는 식 "-C(O)"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "카복실"이란 용어는 식 "-C(O)O-"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "설포닐"이란 용어는 식 "-SO2"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "설페이트"란 용어는 식 "-O-S(O)2-O-"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "카복실산"이란 용어는 식 "-C(O)OH"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "설폭사이드"란 용어는 식 "-S=O"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "포스폰산"이란 용어는 식 "-P(O)(OH)2"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "인산"이란 용어는 식 "-(O)P(O)(OH)2"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 "설폰산"이란 용어는 식 "-S(O)2OH"의 기를 나타낸다.
본 명세서에 이용되는 바와 같은 식 "H"는 수소 원자를 나타낸다.
본 명세서에 이용되는 바와 같은 식 "O"는 산소 원자를 나타낸다.
본 명세서에 이용되는 바와 같은 식 "N"은 질소 원자를 나타낸다.
본 명세서에 이용되는 바와 같은 식 "S"는 황 원자를 나타낸다.
본 명세서에서 이용되는 바와 같은 "아민"이란 용어는, 식 "-NRxRy"의 기를 나타내되, 여기서 Rx 및 Ry는 동일할 수 있거나 또는 독립적으로 H, 위에서 정의된 바와 같은 알킬, 아릴, 사이클로알킬, 사이클로알케닐, 헤테로사이클일 수 있다.
본 명세서에서 이용되는 바와 같은 "아마이드"란 용어는, 식 "-C(O)NRxRy" 또는 "-C(O)N(Rx)(Ry)" 또는 "NRxC(O)Ry"의 기를 나타내되, 여기서 Rx 및 Ry는 동일할 수 있거나 또는 독립적으로 H, 위에서 정의된 바와 같은 알킬, 아릴, 사이클로알킬, 사이클로알케닐, 헤테로사이클일 수 있다.
본 명세서에서 이용되는 바와 같은 "설폰아마이드"란 용어는, 식 "-S(O)2NRxRy" 또는 "NRxRyS(O)2" 또는 "-NRxS(O)2Ry"를 나타내되, 여기서 Rx 및 Ry는 동일할 수 있거나 또는 독립적으로 H, 위에서 정의된 바와 같은 알킬, 아릴, 사이클로알킬, 사이클로알케닐, 헤테로사이클일 수 있다.
본 명세서에서 이용되는 바와 같은 "에스터"란 용어는, "-C(O)O(Rx)"의 기를 나타내되, 여기서 Rx는 위에서 정의된 바와 같은 알킬, 아릴, 사이클로알킬, 사이클로알케닐, 헤테로사이클이다.
본 명세서에서 이용되는 바와 같은 "알데하이드"란 용어는 식 "-C(O)H"의 기를 나타낸다.
본 발명의 몇몇 화합물은 다음과 같다:
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(페닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]피리딘-3-설폰아마이드;
N-(2-{[(4-아미노페닐)설포닐]아미노}-5-클로로페닐)-4-클로로-3-(트라이플루오로메틸)벤젠설폰아마이드;
5-클로로-N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
4-클로로-N-{4-클로로-5-메틸-2-[(페닐설포닐)아미노]페닐}-3-(트라이플루오로메틸)벤젠설폰아마이드;
4-클로로-N-{5-클로로-2-[(페닐설포닐)아미노]페닐}-3-(트라이플루오로메틸)벤젠설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1,3-옥사졸-5-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-(메틸아미노)벤조에이트;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-(메틸아미노)벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2,3-다이옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-2-설폰아마이드;
N-{2-[(바이페닐-4-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸페녹시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-아이소옥사졸-3-일티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸-1-벤조티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드;
4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시벤조산;
N-(4,5-다이클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-tert-뷰틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1H-1,2,4-트라이아졸-5-설폰아마이드;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4--(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
3-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}프로판산;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-에톡시벤조산;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸페닐}아세트아마이드;
N-[2-({[3,5-비스(트라이플루오로메틸)페닐]설포닐}아미노)-4,5-다이클로로페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[2-({[4-(벤질옥시)페닐]설포닐}아미노)-4,5-다이클로로페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
2-클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-플루오로벤조산;
메틸 5-클로로-3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-플루오로벤조산;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2,3-다이하이드로-1H-인덴-5-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(1-나프틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-[4,5-다이클로로-2-({[2-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-2-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,4-다이메틸-1,3-티아졸-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸-1,3-티아졸-2-일}아세트아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아이소퀴놀린-5-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-(4,5-다이클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-(페닐설포닐)-1H-피롤-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메톡시-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-5-설폰아마이드;
1-아세틸-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}인돌린-5-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-2-페닐-1,3-티아졸-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-1,2,3,4-테트라하이드로퀴놀린-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2H-크로멘-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-페닐피리딘-3-설폰아마이드;
에틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]아이소니코티네이트;
N-[4,5-다이클로로-2-({[2-클로로-4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-페녹시피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-페닐티오펜-2-설폰아마이드;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸벤조산;
N-(4,5-다이클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-클로로-4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸-1-벤조티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,5-다이메틸퓨란-3-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(피롤리딘-1-일설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸-3-퓨로에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
2,4-다이클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[4-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시페닐}아세트아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(1-메틸-1H-피라졸-5-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸퓨란-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(페녹시메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-페녹시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5,6-다이클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-에톡시-5-{[(메틸아미노)카보닐]아미노}페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-몰폴린-4-일피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[({3-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}크로만-6-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸티오펜-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-하이드록시벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시티오펜-3-카복실레이트;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-퓨로에이트;
N-(4,5-다이클로로-2-{[(2-클로로-4-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-피리딘-2-일티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4'-플루오로바이페닐-4-일)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로-4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤조티아졸-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-3-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
에틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-3-퓨로에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,4-다이하이드로-2H-1,5-벤조다이옥세핀-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1,3-티아졸-2-일}아세트아마이드;
N-{4,5-다이클로로-2-[({4-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-피리미딘-2-일페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진-7-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-나프틸)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-[(바이페닐-3-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
4-클로로-3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조산;
N-[4,5-다이클로로-2-({[4-(피리딘-2-일옥시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-나프틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[6-(다이메틸아미노)-2-나프틸]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(4'-클로로바이페닐-4-일)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린-6-설폰아마이드;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤질}아세트아마이드;
N-[4,5-다이클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸퀴놀린-8-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-메톡시피리딘-3-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-(4,5-다이클로로-2-{[(2,5-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-아이소옥사졸-5-일티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-(1,3-옥사졸-5-일)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[5-(다이메틸아미노)-1-나프틸]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 2-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조에이트;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-피리미딘-2-일페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(메틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-4-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
2-클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[4-(피리딘-3-일옥시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(에틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-플루오로벤조산;
N-{2-[(바이페닐-2-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-{3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸페닐}아세트아마이드;
N-(2-{[(5-tert-뷰틸-2-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{2-[(벤질설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(아이소뷰틸설포닐)아미노]페닐}티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,2-다이메틸크로만-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀-7-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-사이클로헥실페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
4-클로로-N~1~-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}벤젠-1,3-다이설폰아마이드;
N-(4,5-다이클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-4-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-클로로페녹시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
2-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페녹시}아세트아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸-1-페닐-1H-피라졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
4-아세틸-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(메틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{2-[(벤질설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-나프틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-8-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-4-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(1-나프틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(4-tert-뷰틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[2-({[4-(벤질옥시)페닐]설포닐}아미노)-5-클로로페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,4-다이메틸-1,3-티아졸-5-설폰아마이드;
N-[5-클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조티엔-3-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-[5-클로로-2-({[3-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-{5-클로로-2-[(에틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-3-메틸-1-벤조티엔-2-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(아이소뷰틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로-4-플루오로벤조산;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸-1,3-티아졸-2-일}아세트아마이드;
N-(5-클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1H-1,2,4-트라이아졸-5-설폰아마이드;
3-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페닐}프로판산;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-5-클로로티오펜-2-카복실레이트;
N-{2-[(1-벤조퓨란-5-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소인돌린-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-(2-메틸페녹시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로-1,3-벤조티아졸-6-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-에톡시벤조산;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-플루오로벤조산;
N-(5-클로로-2-{[(2,6-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아이소퀴놀린-5-설폰아마이드;
N-(5-클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-아이소옥사졸-3-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조산;
N-(5-클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조산;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로퀴놀린-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로퀴놀린-8-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-6-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시벤조산;
N-(5-클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[2-({[3,5-비스(트라이플루오로메틸)페닐]설포닐}아미노)-5-클로로페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드
N-(5-클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-(페닐설포닐)-1H-피롤-3-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1H-피라졸-4-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1H-인덴-5-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
메틸 4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조에이트;
N-(5-클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메톡시-3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-1,2,3,4-테트라하이드로퀴놀린-6-설폰아마이드;
N-(5-클로로-2-{[(5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-에톡시-5-{[(메틸아미노)카보닐]아미노}페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(4-아세틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조에이트;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3-다이하이드로-1,3-벤조티아졸-6-설폰아마이드;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-1,3-티아졸-2-일}아세트아마이드;
N-(5-클로로-2-{[(3-클로로-4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2H-크로멘-6-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-몰폴린-4-일피리딘-3-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시티오펜-3-카복실레이트;
N-{5-클로로-2-[(3-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[({4-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-페닐피리딘-3-설폰아마이드;
N-[5-클로로-2-({[4-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-{5-클로로-2-[({3-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-퓨로에이트;
N-[5-클로로-2-({[3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-피리미딘-2-일페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
1-아세틸-N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}인돌린-5-설폰아마이드;
에틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]아이소니코티네이트;
N-(5-클로로-2-{[(5-메틸-1-벤조티엔-2-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(1-메틸-1H-피라졸-5-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}크로만-6-설폰아마이드;
N-(5-클로로-2-{[(2-클로로-4-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
에틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-3-퓨로에이트;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조에이트;
N-(5-클로로-2-{[(4-피리미딘-2-일페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-클로로-4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메틸-3-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-[5-클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1-페닐-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,4-다이하이드로-2H-1,5-벤조다이옥세핀-7-설폰아마이드;
N-[5-클로로-2-({[3-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-5-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(피롤리딘-1-일설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-7-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,2-다이메틸크로만-6-설폰아마이드;
N-[5-클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-2-페닐-1,3-티아졸-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-페녹시피리딘-3-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸-3-퓨로에이트;
N-[5-클로로-2-({[4-(페녹시메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-하이드록시벤조산;
N-(5-클로로-2-{[(5-피리딘-2-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진-7-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-4-설폰아마이드;
N-(5-클로로-2-{[(5-페닐-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-(5-클로로-2-{[(4-페녹시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조티엔-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4'-플루오로바이페닐-4-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
2-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페녹시}아세트아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조산;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸벤조산;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2,4-다이클로로벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5,6-다이클로로피리딘-3-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이클로로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-플루오로-4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로-4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-사이아노-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-나프틸)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-3-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로피리딘-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}피리딘-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-(5-클로로-2-{[(5-아이소옥사졸-5-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이클로로-4-하이드록시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-플루오로벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4'-클로로바이페닐-4-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[5-(1,3-옥사졸-5-일)-2-티에닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀-7-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-클로로벤조산;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로피리딘-3-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로벤조산;
N-{3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸페닐}아세트아마이드;
N-(5-클로로-2-{[(4-사이클로헥실페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-메톡시피리딘-3-설폰아마이드;
4-아세틸-N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-[5-클로로-2-({[5-(다이메틸아미노)-1-나프틸]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로페닐}아세트아마이드;
N-[5-클로로-2-({[4-(피리딘-3-일옥시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(5-tert-뷰틸-2-메틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N~1~-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-클로로벤젠-1,3-다이설폰아마이드;
N-[5-클로로-2-({[4-(2-클로로페녹시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(피리딘-2-일옥시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤질}아세트아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조에이트;
메틸 2-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조에이트;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3-메틸퀴놀린-8-설폰아마이드;
N-[5-클로로-2-({[6-(다이메틸아미노)-2-나프틸]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[5-클로로-3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드.
본 발명의 바람직한 화합물은 다음과 같다:
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-(5-클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-7-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{5-클로로-2-[(메틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸퓨란-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(페닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{4,5-다이클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2,3-다이옥소인돌린-5-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-(4,5-다이클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
N-(4,5-다이클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-(5-클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-{5-클로로-2-[(아이소뷰틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-8-설폰아마이드;
N-(5-클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-2-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(5-클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5,6-다이클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]티오펜-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-[4-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{5-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N,N'-1,2-페닐렌다이티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(3-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-3-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-7-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-메톡시피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드.
본 발명의 더욱 바람직한 화합물은 다음과 같다:
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]티오펜-2-카복실레이트;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-2-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2,3-다이옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸퓨란-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-2-설폰아마이드;
N-{4-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드.
화학식 I의 몇몇 화합물 및 그들의 중간생성물은 그들의 구조에 적어도 하나의 입체생성 중심(stereogenic center)을 지닌다. 이 입체생성 중심은 R 또는 S 입체 배치로 존재할 수 있고, 상기 R 및 S 표기는 문헌[Pure Appli. Chem. (1976), 45, 11-13]에 기재된 규칙에 대응하여 이용된다.
"약제학적으로 허용가능한 염"이란 상기 확인된 화합물의 소망의 생물학적 활성을 유지하고 독성학 효과를 최소로 혹은 원치않는 것이 없도록 발현하는 염 혹은 복합체를 지칭한다. 본 발명에 따른 "약제학적으로 허용가능한 염"은 치료적으로 활성이고 비독성인 염기 혹은 산 염 형태를 포함하며, 이는 화학식 I의 화합물을 형성하는 것이 가능하다.
염기로서 유리 형태로 생성되는 화학식 I의 화합물의 산 부가염 형태는 무기산, 예를 들어, 염화수소산, 브롬화수소산, 황산, 인산, 질산 등; 또는 유기 산, 예를 들어, 아세트산, 하이드록시아세트산, 프로판산, 락트산, 피루브산, 말론산, 푸마르산, 말레산, 옥살산, 타르타르산, 숙신산, 말산, 아스코르브산, 벤조산, 탄닌산, 파모산, 시트르산, 메틸설폰산, 에탄설폰산, 벤젠설폰산, 포름산 등과 같은 적절한 산으로 유리 염기를 처리함으로써 얻어질 수 있다(Handbook of Pharmaceutical Salts, P.Heinrich Stahal& Camille G. Wermuth (Eds), Verlag Helvetica Chemica Acta-, 2002, 329-345).
산 형태로 생기는 화학식 I의 화합물의 염기 부가염 형태는 무기 염기, 예를 들어, 수산화나트륨, 수산화마그네슘, 수산화칼륨, 수산화칼슘, 암모니아 등; 또는 유기 염기, 예를 들어, L-아르기닌, 에탄올아민, 베타인, 벤자틴, 몰폴린 등과 같은 적절한 염기로 상기 산을 처리함으로써 얻어질 수 있다(Handbook of Pharmaceutical Salts, P.Heinrich Stahal& Camille G. Wermuth (Eds), Verlag Helvetica Chemica Acta-, 2002, 329-345).
화학식 I의 화합물들 및 그들의 염은 본 발명의 범위 내에 포함된 용매화물의 형태일 수 있다. 이러한 용매화물은 예를 들어 수소화물, 알콜레이트 등을 포함한다.
본 발명에 관하여 화합물 또는 화합물들이란, 특정 이성질체 형태가 구체적으로 지칭되지 않는 한 그의 가능한 이성질체 형태 및 그의 혼합물의 각각의 그 화합물을 망라하도록 의도된다.
본 발명에 따른 화합물은 상이한 다형체 형태로 존재할 수 있다. 상기 화학식에 명시적으로 표시되지는 않았지만, 이러한 형태는 본 발명의 범위 내에 포함되도록 의도된다.
본 발명의 화합물은 케모카인 수용체와 연관된 성분이 있는 것으로 여겨질 수 있는 병태를 치료 혹은 예방하는데 이용하기 위하여 표시된다.
다른 실시형태에 있어서, 약제학적으로 허용가능한 담체 중에 본 발명의 적어도 하나의 화합물을 포함하는 약제학적 조성물이 제공된다.
본 발명의 추가의 실시형태에 있어서, 케모카인 수용체의 조절과 연관된 장애를 치료하는 방법이 제공된다. 이러한 방법은, 예를 들어, 치료적 유효량의 적어도 1종의 본 발명의 화합물을 함유하는 약제학적 조성물을 이를 필요로 하는 대상체에게 투여함으로써 수행될 수 있다.
이들 화합물은 CCR 조절에 의해 완화되는 병태 및 질환의 범위를 지니는 인간을 비롯한 포유동물의 치료에 유용하다. CCR 조절제의 치료적 유용성은, 예를 들어, 이하의 것들 포함하지만 이들로 제한되는 것은 아닌 피부 염증 질환 및 병태이다: 주사(rosacea)(피부 바로 아래의 혈관의 팽창), 햇볕으로 인한 화상, 만성 태양광 손상, 신중한 홍반(discreet erythemas), 건선, 아토피성 피부염, 폐경관련 안면홍조, 고환적출술아토피성 피부염으로부터 초래된 안면홍조, 광노화, 지루성 피부염, 여드름, 알레르기성 피부염, 자극성 피부염, 안면의 모세혈관확장증(이미 존재하는 소혈관의 팽창), 비류(rhinophyma)(소낭 팽창을 지니는 코의 비대), 적색 주먹코, 여드름-유사 피부 발진(스며나오거나 딱지가 앉을 수 있음), 안면의 작열감 혹은 자통 감각, 자극적이고 충혈되며 수양성의 눈, 피부의 혈관의 팽창을 지니는 피부 과민반응, 리엘 증후군(Lyell's syndrome), 스티븐스-존슨 증후군, 가벼운 다형홍반, 심한 다형홍반 및 기타 염증성 피부 질환, 광선 각화증, 비소 각질증, 염증성 및 비염증성 여드름, 어린선 및 기타 피부의 각질화 및 과다증식성 장애, 습진, 상처 치유.
CCR 조절제의 치료적 유용성은 이하의 것들을 포함하지만 이들로 제한되는 것은 아닌 안구 염증 질환이다: 포도막염, 안구 건조, 각막염, 눈의 후방 부분에 유발되는 알레르기성 안 질환 및 병태, 예컨대, 황반증 및 망막 변성, 예를 들어, 비삼출성 연령 관련 황반변성, 삼출성 연령 관련 황반변성, 맥락막 혈관신생, 당뇨 망막병증, 급성 황반 신경망막병증, 중심성 장액 맥락망막병증, 낭종성 황반부종 및 당뇨병성 황반부종 등; 포도막염, 망막염, 및 맥락막염, 예컨대, 급성 다발성 판형상 색소 상피증, 베제트병, 버드샷 망막맥락막증, 전염병(매독, 라임, 결핵, 톡소플라스마증), 중간 포도막염(평면 부염(pars planitis)), 다발성 맥락막염, 다발성 소실성 백반증후군(multiple evanescent white dot syndrome: mewds), 눈의 사르코이드증, 후공막염, 사행성 맥락막염, 안저 섬유증 및 포도막염 증후군, 포크트-코야나기-하라다 증후군(Vogt-Koyanagi-and Harada syndrome); 혈관 질환/삼출성 질환, 예컨대, 망막 동맥 폐색 질환, 중심성 망막 정맥 폐색, 파종성 혈관내 응고증, 분지성 망막 정맥 폐색, 고혈압성 안저 변화, 안허혈 증후군, 망막 동맥성 미세동맥류, 코츠병(Coat's disease), 중심오목부근 모세혈관확장증, 반구 망막 정맥 폐쇄, 유두정맥염, 망막 중심 동맥 폐쇄, 분지 망막 동맥 폐쇄, 경동맥 질환(carotid artery disease: CAD), 서리 가지 동맥염, 겸상 적혈구망막병증 및 기타 이상혈색소증, 망막색소선조, 가족성 삼출 유리체망막병증, 및 이일즈병(Eales disease); 외상성/수술적 병태, 예컨대, 교감성 안염, 포도막염성 망막 질환(uveitic glaucoma), 망막 박리, 외상, 레이저에 의해 초래된 병태, 광역동 치료에 의해 초래된 병태, 광응고화, 수술 중의 관류저하, 방사선 망막병증, 및 골수 이식 망막병증; 증식성 장애, 예컨대, 증식성 유리체 망막병증 및 망막 전막(epiretinal membrane), 및 증식성 당뇨 망막병증; 감염 질환, 예컨대, 안구 히스토플라스마증, 안구 톡소카라증, 추정된 안구 히스토플라스마증 증후군(presumed ocular histoplasmosis syndrome: POHS), 안구내막염, 톡소플라스마증, HIV 감염과 관련된 망막 질환, HIV 감염과 관련된 맥락막 질환, HIV 감염과 관련된 포도막 질환, 바이러스 망막염, 급성 망막 괴사, 진행성 외망막 괴사, 진균 망막 질환, 안구 매독, 안구 결핵, 광범위 일측 아급성 신경망막염, 및 구더기증; 유전자 질환, 예컨대, 망막염 색소변성증, 망막 이영양증, 선천성 야맹증, 추체 이영양증, 스타가르트병 및 황반 안저와 관련된 전신 장애, 베스트병, 망막 색소 상피의 패턴 이영양증(pattern dystrophy), X-연관성 망막층간분리, 솔스비 안저 이상증, 양성 동심성 황반병증, 비티 결정 이영양증(Bietti's crystalline dystrophy), 및 탄력섬유성 가황색종; 망막 열공/구멍, 예컨대, 망막 박리, 황반 천공 및 거대 망막 열공; 종양, 예컨대, 종양과 관련된 망막 질환, 망막 색소 상피의 선천성 비대증, 후방 포도막 흑색종, 맥락막 혈관종, 맥락막 골종, 맥락막 전이, 망막 및 망막 색소 상피의 동반된 과오종, 망막모세포종, 안저의 혈관증식성 종양, 망막 별아교세포종, 및 안구내 림프 종양; 및 안구의 후방 부분에 유발되는 여러 종류의 기타 질환, 예컨대, 점상 내층 맥락막병증, 급성 후부 다발성 판형상 색소 상피증, 근시성 망막 변성 및 급성 망막 색소 상피염.
본 발명의 또 다른 실시형태에 있어서, 케모카인 수용체의 조절과 연관된 장애를 치료하는 방법이 제공된다. 이러한 방법은, 예를 들어, 치료적 유효량의 본 발명의 적어도 1종의 화합물 또는 그의 임의의 조합물, 또는 약제학적으로 허용가능한 염, 수소화물, 용매화물, 결정 형태 및 개별의 이성질체, 거울상이성질체, 및 그의 부분입체이성질체를 이를 필요로 하는 대상체에 투여함으로써 수행될 수 있다.
본 발명은, 포도막염, 안구 건조, 각막염, 눈의 후방 부분에 유발되는 알레르기성 안 질환 및 병태, 예컨대, 황반증 및 망막 변성, 예를 들어, 비삼출성 연령 관련 황반변성, 삼출성 연령 관련 황반변성, 맥락막 혈관신생, 당뇨 망막병증, 급성 황반 신경망막병증, 중심성 장액 맥락망막병증, 낭종성 황반부종, 및 당뇨병성 황반부종; 포도막염, 망막염, 및 맥락막염, 예컨대, 급성 다발성 판형상 색소 상피증, 베제트병, 버드샷 망막맥락막증, 전염병(매독, 라임, 결핵, 톡소플라스마증), 중간 포도막염(평면 부염), 다발성 맥락막염, 다발성 소실성 백반증후군(mewds), 눈의 사르코이드증, 후공막염, 사행성 맥락막염, 안저 섬유증 및 포도막염 증후군, 포크트-코야나기-하라다증후군; 혈관 질환/삼출성 질환, 예컨대, 망막 동맥 폐색 질환, 중심성 망막 정맥 폐색, 파종성 혈관내 응고증, 분지성 망막 정맥 폐색, 고혈압성 안저 변화, 안허혈 증후군, 망막 동맥성 미세동맥류, 코츠병, 중심오목부근 모세혈관확장증, 반구 망막 정맥 폐쇄, 유두정맥염, 망막 중심 동맥 폐쇄, 분지 망막 동맥 폐쇄, 경동맥 질환(CAD), 서리 가지 동맥염, 겸상 적혈구망막병증 및 기타 이상혈색소증, 망막색소선조, 가족성 삼출 유리체망막병증 및 이일즈병; 외상성/수술적 병태, 예컨대, 교감성 안염, 포도막염성 망막 질환, 망막 박리, 외상, 레이저에 의해 초래된 병태, 광역동 치료에 의해 초래된 병태, 광응고화, 수술 중의 관류저하, 방사선 망막병증, 및 골수 이식 망막병증; 증식성 장애, 예컨대, 증식성 유리체 망막병증 및 망막 전막, 및 증식성 당뇨 망막병증; 감염 질환, 예컨대, 안구 히스토플라스마증, 안구 톡소카라증, 추정된 안구 히스토플라스마증 증후군(POHS), 안구내막염, 톡소플라스마증, HIV 감염과 관련된 망막 질환, HIV 감염과 관련된 맥락막 질환, HIV 감염과 관련된 포도막 질환, 바이러스 망막염, 급성 망막 괴사, 진행성 외망막 괴사, 진균 망막 질환, 안구 매독, 안구 결핵, 광범위 일측 아급성 신경망막염, 및 구더기증; 유전자 질환, 예컨대, 망막염 색증소변성, 망막 이영양증, 선천성 야맹증, 추체 이영양증, 스타가르트병 및 황반안저와 관련된 전신 장애, 베스트병, 망막 색소 상피의 패턴 이영양증, X-연관성 망막층간분리, 솔스비 안저 이상증, 양성 동심성 황반병증, 비티 결정 이영양증, 및 탄력섬유성 가황색종; 망막 열공/구멍, 예컨대, 망막 박리, 황반 천공 및 거대 망막 열공; 종양, 예컨대, 종양과 관련된 망막 질환, 망막 색소 상피의 선천성 비대증, 후방 포도막 흑색종, 맥락막 혈관종, 맥락막 골종, 맥락막 전이, 망막 및 망막 색소 상피의 동반된 과오종, 망막모세포종, 안저의 혈관증식성 종양, 망막 별아교세포종, 및 안구내 림프 종양; 및 눈의 후방 부분에 유발되는 여러 종류의 기타 질환, 예컨대, 점상 내층 맥락막병증, 급성 후부 다발성 판형상 색소 상피증, 근시성 망막 변성 및 급성 망막 색소 상피염을 포함하지만 이들로 제한되는 것은 아닌 안구 염증 질환의 치료용의 약제의 제조를 위한, 화학식 I의 화합물 또는 그의 약제학적으로 허용가능한 염의 용도에 관한 것이다.
임의의 주어진 경우에서 투여될 화합물의 실제량은 관련된 환경, 예컨대, 병태의 중증도, 환자의 연령과 체중, 환자의 일반적 신체 상태, 병태의 원인 및 투여 경로를 고려해서 의사에 의해 결정될 것이다.
환자는 정제, 액체, 캡슐, 분말 등과 같은 임의의 허용가능한 형태로 상기 화합물을 투여받을 것이거나, 또는 특히 환자가 구역질을 겪는다면 다른 경로가 바람직하거나 필요할 수 있다. 그러한 다른 경로는, 예외 없이, 경피, 비경구, 피하, 비강내, 이식 스텐트(implant stent)를 통하여, 척추관내, 유리체내, 안구에 대한 국소투여, 안구 후방 투여, 근육내, 정맥내, 및 직장내 전달 모드를 포함할 수 있다. 또한, 제형들은 상기 활성 화합물을 소정 기간의 시간에 걸쳐 지연 방출하도록 고안되거나, 또는 치료 과정 동안 주어진 시간에 방출되는 약물의 양을 세심하게 제어하도록 설계될 수 있다.
본 발명의 다른 실시형태에 있어서, 약제학적으로 허용가능한 담체 내에 적어도 1종의 본 발명의 화합물을 포함하는 약제학적 조성물이 제공된다. "약제학적으로 허용가능한"이라는 구절은 담체, 희석제 또는 부형제가 제형의 다른 성분과 상용성(compatible)이어야 하고 그의 수용자에게 유해하지 않아야 함을 의미한다.
본 발명의 약제학적 조성물은 고체, 용액, 에멀전, 분산액, 패치, 마이셀(micelle), 리포좀 등의 형태로 사용될 수 있고, 얻어진 조성물은 장관내 또는 비경구 적용에 적합한 유기 또는 무기 담체 또는 부형제와 혼합된 활성성분으로서 하나 이상의 본 발명의 화합물을 함유한다. 본 발명의 화합물은 정제, 팰릿, 캡슐, 좌약, 용액, 에멀전, 현탁액, 및 사용하기에 적합한 임의의 다른 형태에 대한 통상의 비독성, 약제학적으로 허용가능한 담체와 조합될 수 있다. 사용될 수 있는 담체는 글루코스, 락토스, 아카시아 검, 젤라틴, 만니톨, 전분 페이스트, 삼규산 마그네슘, 탤크, 옥수수 전분, 케라틴, 콜로이드성 실리카, 감자 전분, 유레아, 중간 사슬 길이의 트라이글라이세라이드, 덱스트란, 및 제조하는 제제에 사용하기에 적합한 고체, 반고체, 또는 액체 형태의 다른 담체를 포함한다. 또한 보조제, 안정화제, 증점제 및 착색제와 향수가 사용될 수 있다. 본 발명의 화합물은 공정 또는 질환 상태에 대해서 목적으로 하는 효과를 내기에 충분한 양으로 약제학적 조성물에 포함된다.
본 발명의 화합물을 함유하는 약제학적 조성물은, 예를 들어, 정제, 트로키제(troche), 로젠지(lozenge), 수성 또는 오일성 현탁액, 분산성 분말 또는 과립, 에멀전, 경질 또는 연질 캡슐, 또는 시럽 또는 엘릭서(elixir)와 같은 경구 사용에 적합한 형태일 수 있다. 경구 사용을 위해 의도된 조성물은 약제학적 조성물의 제조를 위해 당업계에 공지된 임의의 방법에 따라 제조될 수 있으며, 이러한 조성물은 약제학적으로 적합하고(pharmaceutically elegant) 또 맛이 좋은(palatable) 제제를 제공하기 위하여 수크로스, 락토스, 또는 사카린과 같은 감미제, 페퍼민트, 윈터그린 또는 체리의 오일과 같은 향미제, 착색제 및 방부제로 이루어진 군으로부터 선택된 하나 이상의 물질을 함유할 수 있다. 비독성의 약제학적으로 허용가능한 부형제와 혼합된 본 발명의 화합물을 함유하는 정제는 공지된 방법에 의해 또한 제조될 수 있다. 사용된 부형제는 예를 들어, (1) 탄산칼슘, 락토스, 인산칼슘 또는 인산나트륨과 같은 불활성 희석제; (2) 옥수수 전분, 감자 전분 또는 알긴산과 같은 과립제 및 붕해제; (3) 트래거캔트 검, 옥수수 전분, 젤라틴 또는 아카시아와 같은 결합제 및 (4) 스테아르산 마그네슘, 스테아르산 또는 탤크와 같은 윤활제일 수 있다. 상기 정제는 코팅되지 않거나 또는 이들은 위장관에서 붕해 및 흡수를 지연시키기 위해 공지 수법에 의해 코팅되어 장기간에 걸쳐 서방 활성을 제공할 수 있다. 예를 들어, 글라이세릴 모노스테아레이트 또는 글라이세릴 다이스테아레이트와 같은 시간 지연 물질이 이용될 수 있다.
몇몇 경우에 있어서, 경구 사용을 위한 제형은 경질 젤라틴 캡슐 형태일 수 있고, 이때 본 발명의 화합물은 예를 들어, 탄산칼슘, 인산칼슘 또는 카올린과 같은 불활성 고체 희석제와 혼합된다. 이들은 연질 젤라틴 캡슐 형태일 수 있고, 이때 본 발명의 화합물은 물 또는 예를 들어 땅콩유, 액체 파라핀, 또는 올리브유와 같은 오일 매질과 혼합된다.
약제학적 조성물은 멸균의 주사가능한 현탁액 형태일 수 있다. 이 현탁액은 적합한 분산제 또는 습윤제 및 현탁제를 사용하여 공지 방법에 따라 제형화될 수 있다. 멸균의 주사가능한 제제는 비독성의 비경구적으로 허용되는 희석제 또는 용매 중의 멸균 주사가능한 용액 또는 현탁액, 예를 들어, 1,3-뷰탄다이올 중의 용액일 수 있다. 멸균, 고정유(fixed oil)가 통상적으로 용매 또는 현탁 매질로서 사용된다. 이 목적을 위하여 합성 모노- 또는 다이글라이세라이드, 지방산(올레산 포함), 참기름, 코코넛유, 땅콩유, 면실유 등과 같은 천연 유래 식물유, 또는 올레산 에틸 등과 같은 합성 지방 비히클(vehicle)을 비롯한 임의의 완하성 지방유(bland fixed oil)가 사용될 수 있다. 필요에 따라 완충액, 방부제, 산화방지제 등이 포함될 수 있다.
본 발명의 화합물은 또한 약물의 직장 투여를 위해 좌약 형태로 투여될 수 있다. 이들 조성물은 본 발명의 화합물을 통상의 온도에서 고체이지만 직장 강에서 액화 및/또는 용해시켜 약물을 방출하는, 코코아 버터, 폴리에틸렌 글라이콜의 합성 글라이세라이드 에스터와 같은 적합한 비자극성 부형제와 혼합함으로써 제조될 수 있다.
본 발명의 화합물 및 그의 약제학적으로 허용가능한 염은 국소 점안액, 직접 주입, 눈의 뒤쪽에서의 적용, 또는 서방형 팰릿, 현탁제, 겔 또는 지속 전달 장치, 예컨대, 당업계에 공지된 임의의 적절한 약물 전달 시스템(drug delivery system: DDS) 등과 같은 장기간 작용을 더욱 증대시킬 수 있는 제형을 포함하지만 이들로 제한되는 것은 아닌 상이한 경로를 통해서 투여될 수있다. 국소 투여가 바람직하지만, 이 화합물은 미국 특허 제7,931,909호에 기재된 바와 같은 안구내 이식물에 이용될 수도 있다.
개별 대상체는 증상의 중증도에서 큰 폭의 변화를 제공할 수 있고 각 약물은 그의 독특한 치료 특징을 지니기 때문에, 각 대상체에 대하여 이용되는 정확한 투여 모드 및 투여량은 의사의 재량에 따른다.
본 명세서에 기재된 화합물 및 약제학적 조성물은 케모카인 수용체의 효능제 또는 기능적 길항제에 의한 치료에 반응하는 질환의 치료 및/또는 상태의 완화를 위한 인간을 비롯한 포유동물에서 의약으로서 유용하다. 따라서, 본 발명의 추가의 실시형태에서, 케모카인 수용체의 조절과 관련된 장애를 치료하는 방법이 제공된다. 이러한 방법은 예를 들어 치료를 필요로 하는 대상체에게 적어도 1종의 본 발명의 화합물을 함유하는 약제학적 조성물을 치료적 유효량 투여함으로써 수행될 수 있다. 본 명세서에 기재된 바와 같이, "치료적 유효량"이란 용어는 연구자, 수의과 의사, 의사 또는 기타 임상의들이 찾고 있는, 치료를 필요로 하는 대상체의 생물학적 또는 의료적 반응을 유발하는 약제학적 조성물의 양을 의미한다. 몇몇 실시형태에서, 치료를 필요로 하는 상기 대상체는 포유동물이다. 몇몇 실시형태에서, 상기 포유동물은 인간이다.
본 발명은 또한 화학식 I의 화합물을 제조하는 방법에 관한 것이다. 본 발명에 따른 화학식 I의 화합물은 합성 유기 화학의 분야에서 당업자가 이해하고 있는 바와 같은 통상의 방법과 마찬가지로 제조될 수 있다. 이하에 기재된 합성 반응식은 본 발명에 따른 화합물이 어떻게 제조되는지를 예시하고 있다. 당업자라면 화학식 I로 커버되는 본 발명의 임의의 화합물을 합성하기 위하여 반응식 1 또는 반응식 2를 통상적으로 변형 및/또는 적응시킬 수 있을 것이다.
이하의 약어가 일반적인 반응식들 및 구체적인 실시예들에서 이용된다:
NH4HCO3 중탄산 암모늄
CH3CN 아세토나이트릴
CH2Cl2 다이클로로메탄
DMF N,N-다이메틸포름아마이드
NaOH 수산화나트륨
MeOH 메탄올
CD3OD 중수소화 메탄올
NH3 암모니아
HCl 염화수소산(염산)
Na2SO4 황산나트륨
NaHCO3 중탄산나트륨
EtOH 에탄올
MgSO4 황산 마그네슘
EtOAc 에틸 아세테이트
CDCl3 중수소화 클로로포름
CHCl3 클로로포름
DMSO-d6 중수소화 다이메틸 설폭사이드
Et3N 트라이에틸아민
DIPEA N,N-다이아이소프로필에틸아민
TFA 트라이플루오로아세트산
THF 테트라하이드로퓨란
NaH 수소화나트륨
HOAc 아세트산
DMAP 4-다이메틸아미노피리딘
NH4Cl 염화암모늄
Et2O 다이에틸에터
MeLi 메틸리튬
H2 수소(기체)
Pd-C 탄소 상의 팔라듐
Zn 아연
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설폰아마이드 중간생성물 A는 적절하게 치환된 페닐렌 다이아민에서 출발하여 제조되었다. 설폰아마이드 중간생성물 D는 적절하게 치환된 2-나이트로아닐린에서 출발하여 제조되었다. THF 및 메탄올 중 아연 더스트 및 포화 수성 염화암모늄 용액을 이용한 중간생성물 D의 환원에 의해 중간생성물 E 유형을 수득하였다. 화학식 I의 비스-설폰아마이드는 100℃(방향족 설포닐 클로라이드에 대해서 방법 A; 또는 카복실산기를 포함하는 방향족 설포닐 클로라이드에 대해서 변성 워크업에 의한 방법 B)에서, 또는 실온(rt)(방법 C)에서 피리딘 중 중간생성물 A 또는 중간생성물 E로부터 제조되었다.
방법 A, B 또는 C를 이용해서 실패한 지방족 설포닐 클로라이드에 대해서 그리고 방향족 설포닐 클로라이드에 대해서, 합성은 중간생성물 B 및 중간생성물 C를 통해서 변형시켰다. 1-클로로메틸 에틸 에터를 이용해서 중간생성물 A의 설폰아마이드 질소를 보호하여 헤미아미날 에터 중간생성물 B를 수득하였다.
메틸 리튬(MeLi)을 이용한 중간생성물 B의 탈프로톤화 및 방향족 설포닐 클로라이드에 의한 후속의 반응에 의해 중간생성물 C 유형의 화합물을 얻었고, 이것은 에탄올의 존재 하에 4M 염산(HCl)/다이옥산을 이용해서 화학식 I의 비스-설폰아마이드로 탈보호되었다(두 단계 조합: 방법 D).
지방족 설포닐 클로라이드와의 중간생성물 B의 반응은 50℃에서 클로로포름(CHCl3)/아세톤 중 트라이에틸아민 및 4-다이메틸아미노피리딘(DMAP)의 존재 하에 수행되어 중간생성물 C 유형의 화합물을 얻었고, 이것은 에탄올의 존재 하에 4M 염산(HCl)/다이옥산을 이용해서 화학식 I의 비스-설폰아마이드로 탈보호되었다(두 단계 조합: 방법 E).
전술한 일반적인 설명 및 이하의 상세한 설명은 모두 예시적으로 설명하기 위한 것일 뿐 청구된 본 발명을 제한하려는 것이 아님을 이해해야 한다. 본 명세서에 사용된 바와 같이, 단수의 이용은 특별히 다르게 기술되지 않는 한 복수도 포함한다.
본 발명의 몇몇 화합물은 하나 이상의 비대칭 중심을 함유할 수 있어, 상기 화합물이 거울상 이성질체 형태뿐만 아니라 부분입체이성질체 형태로 존재할 수 있다는 것은 당업자에게 명백할 것이다. 특별하게 달리 언급되지 않는 한, 본 발명의 범위는 모든 거울상 이성질체, 부분입체이성질체 및 라세미 혼합물을 포함한다. 본 발명의 몇몇 화합물은 약제학적으로 허용가능한 산 또는 염기와 함께 염을 형성할 수 있고, 본 명세서에 기재된 화합물의 이러한 약제학적으로 허용가능한 염은 또한 본 발명의 범위 내이다.
본 발명은 모든 약제학적으로 허용가능한 동위원소 농축(isotopically enriched) 화합물을 포함한다. 본 발명의 임의의 화합물은 농축되거나 또는 프로튬 1H(또는 H) 대신 중수소 2H(또는 D)와 같이 천연 비율과는 상이한 하나 이상의 동위원소성 원자를 함유할 수 있거나 또는 12C 대신 13C 농축 물질을 사용할 수 있다. 유사한 치환기가 N, O 및 S에 대해서 이용될 수 있다. 동위원소의 사용은 본 발명의 분석적 양상뿐만 아니라 치료적 양상에서 도움을 줄 수 있다. 예를 들어, 중수소의 사용은 본 발명의 화합물의 대사(속도)를 변경함으로써 생체내 반감기를 증가시킬 수 있다. 이들 화합물은 동위원소적으로 농축된 시약을 사용하여 제법에 따라서 제조될 수 있다.
당업자에게 명백한 바와 같이, 개별적 이성질체 형태는 통상의 방식으로 그의 혼합물의 분리에 의해 얻어질 수 있다. 예를 들어, 부분입체 이성질체성 이성질체의 경우, 크로마토그래피 분리가 이용될 수 있다.
실시예에 언급된 화합물의 IUPAC 명칭은 ACD 버전 8에 따라 생성되었고, 실시예에 이용된 중간생성물 및 시약 명명은 MDL ISIS Draw 2.5 SP1로부터의 Auto Nom 2000 또는 켐 바이오 드로 울트라 버전 12.0(Chem Bio Draw Ultra version 12.0) 등과 같은 소프트웨어로 생성되었다.
일반적으로, 화합물의 특성규명은 핵자기 공명 및/또는 질량 분광법에 의해 수행된다. 부르커 어드밴스(Bruker Avance) 300 상에 기록된 NMR 스펙트럼, 주위 온도에서 표시된 용매 중에서의 1H-NMR(300 ㎒); 화학적 이동(ppm), 결합 상수(㎐). HPLC-MS: HPLC-시스템: 아질런트(Agilent) 1100 시리즈, MS: 써모 디오넥스 서베이어(Thermo dionex Surveyor) MSQ 플러스. 칼럼 제미니엔엑스(GeminiNX) C18, 3㎛, 2.1×50㎜, 구배: 97% A(산성: 수중 0.1% TFA; 염기성: 수중 1mM NH4HCO3 pH 10) 및 3% B(산성: CH3CN 중 0.085% TFA; 염기성: CH3CN) 0.1분 동안, 이어서 2.1분에 3% A 및 97% B로, 그 후 3% A 및 97% B 0.3분 동안(유량: 0.8㎖/분); 또는 칼럼 아스센티스 익스프레스(Ascentis express) C18, 2.7㎛, 3×50㎜, 구배: 97% A(산성: 수중 0.1% TFA; 염기성: 수중 1mM NH4(CO3)2 pH 10) 및 3% B(산성: CH3CN 중 0.085% TFA; 염기성: CH3CN) 0.05분 동안, 이어서 2.9분에 3% A 및 97% B로, 그 후 3% A 및 97% B 0.2분 동안(유량: 1.3㎖/분); 체류 시간 tR[분]; 254 및 220㎚에서 UV 검출; 표시된 바와 같은 이온화 방법.
합성이 기재되지 않은 모든 시약, 용매, 촉매는 시그마 알드리치(Sigma Aldrich), 플루카(Fluka), 바이오-블록스(Bio-Blocks), 콤비-블록스(Combi-blocks), TCI, VWR, 란캐스터(Lancaster), 오크우드(Oakwood), 트랜스 월드 케미컬(Trans World Chemical), 알파(Alfa), 피셔(Fisher), 메이브리지(Maybridge), 프론티어(Frontier), 매트릭스(Matrix), 우크로그신스(Ukrorgsynth), 토론토(Toronto), 리얀 사이언티픽(Ryan Scientific), 실리사이클(SiliCycle), 아나스펙(Anaspec), 신 켐(Syn Chem), 켐-임펙스(Chem-Impex), MIC-사이언티픽 리미티드(MIC-scientific, Ltd)와 같은 화학약품 판매상으로부터 구입되지만; 몇몇 기지의 중간생성물은 공개된 절차에 따라서 제조되었다. 용매는 적절한 품질로 상업적 공급원으로부터 구입하고 입수한 그대로 사용되었다. 공기 및/또는 수분 민감성 반응은 아르곤 또는 질소 분위기 하에 수행되었다.
통상 본 발명의 화합물은 크로마토그래피에 의해 정제되었다:
TLC: 머크(Merck)(실리카겔 60 F254, 0.25㎜);
플래시 크로마토그래피: 플루카(Fluka) 실리카겔 60(0.04-0.063㎜) 및 인터킴 푸리플래시(Interchim Puriflash) IR 60 실리카겔(0.04-0.063㎜);
MPLC 순상(Normal Phase): 용매계 헥산(A)/EtOAc(B), 칼럼 D: YMC*Gel 실리카 SL06S50(0.006-50㎛), 60×200㎜, 유량 175㎖/분, 프로그램 3(7% B에서 시작하여, 그 후 12분에 100% B, 이어서 5분 동안 100% B), 프로그램 7(25% B에서 시작하여, 12분에 100% B, 이어서 5.5.분 동안 100%);
순상 분취 HPLC: 마세리-나겔(Macherey-Nagel) VP100/21 누클레오실(Nucleosil) 50Å-10㎛, 헥산/EtOAc/MeOH 구배.
역상 분취 HPLC: 워터스 엑스브리지(Waters Xbridge) C18 150×30㎜, 5㎛ 또는 페노메넥스 제미니엔엑스(Phenomenex GeminiNX) C18 액시아 팩(axia pack) 100×30㎜, 5㎛, 0.1% TFA 또는 10mM NH4HCO3(pH 10)와 함께 물/CH3CN 구배.
이하의 실시예는 단지 예시적인 목적을 위한 것으로 어떠한 방식으로도 본 발명을 제한하는 것으로 의도된 것으로 아니고 그와 같이 해석되어서도 안 된다. 당업자라면 본 발명의 정신이나 범위를 넘는 일 없이 이하의 실시예의 변화와 변경이 행해질 수 있다는 것을 이해할 수 있을 것이다.
화학식 I의 비스-설폰아마이드의 합성
방법 A
방법 A는 R5가 카복실산기를 지니지 않는 경우에 적용된다. 피리딘(1㎖) 중 중간생성물 A(50㎎, 0.155m㏖)의 용액에 설포닐 클로라이드(1.5당량)를 실온에서 첨가하였다. 이 혼합물을 수용하는 스크류 캡 튜브(screw cap tube)를 신속하에 100℃ 고온 가열 블록으로 옮기고, 이 혼합물을 100℃에서 30분 동안 교반하였다. 이 반응이 TLC 분석(또는 의심스러울 경우엔 HPLC 분석)에 따라 실패한 경우, 방법 C를 적용하였다. TLC 분석(또는 의심스러울 경우엔 HPLC 분석)이 출발 물질의 주된 양의 존재를 나타낸다면, 추가의 설포닐 클로라이드(1.5당량)를 첨가하고, 100℃에서의 교반을 더욱 30분 동안 지속시켰다.
절반 포화된 수성 NaHCO3 용액을 실온에서 첨가하고 나서, CH2Cl2에 의해 추출하였다. 유기층을 실리카겔 및 MgSO4의 패드를 통해서 여과시키고, 해당 패드를 CH2Cl2/MeOH 9:1로 헹구고 나서, 그 여과액을 농축시켰다. 분취 순상 HPLC(보통보다 큰 크기의 칼럼: 마세리-나겔(Machery-Nagel) VP 150/32 누클레오실(Nucleosil) 50-10, 헥산/EtOAc/MeOH 구배)에 의한 정제에 의해 화학식 I의 화합물을 얻었다. 추가의 정제가 필요하다면, Et2O를 이용한 세척 혹은 역상 분취에 의한 추가의 정제, 또는 물질의 속성에 따라서 Et2O/CH2Cl2를 이용한 세척 절차를 수행하였다.
방법 B
방법 B는 R5가 카복실산기를 포함할 경우 적용된다. 이 반응은 방법 A에 기재된 바와 같이 수행되었고, 워크업(workup)은 변경하였다: 절반 포화된 수성 NaHCO3 용액을 실온에서 첨가하고 CH2Cl2에 의한 추출을 수행하였다. 수층에 4M 수성 HCl 용액을 첨가함으로써 pH를 2로 조정하였다. 이 혼합물을 CH2Cl2로 추출하였고, 생성물은 비혼화성 오일로서 생성된다. 이 경우에, 수층을 제거하고, 오일을 유기층에 용해시키기 위하여 MeOH를 첨가하고, 이 유기층을 실리카겔 및 MgSO4의 패드를 통해서 여과시키고 나서, 해당 패드를 CH2Cl2/MeOH 8:2로 헹구고, 그 여과액을 농축시켰다. 분취용 역상 HPLC(산성 이동상)에 의한 정제를 실시하여 화학식 I의 화합물을 얻었다. 추가의 정제가 필요하다면, Et2O(초음파 욕)를 이용한 세척 절차 혹은 역상 분취 HPLC(산성 이동상)에 의해서 추가의 정제를 수행하였다.
방법 C
피리딘(1㎖) 중 중간생성물 A(80㎎, 0.248m㏖)의 용액에 설포닐 클로라이드(1.5당량)를 실온에서(스크류 캡 튜브) 첨가하였다. 이 혼합물을 실온에서 2시간 동안 교반하였다. 이 반응이 TLC 분석(또는 의심스러울 경우엔 HPLC 분석)에 따라 실패한 경우, 방법 D를 적용하였다. TLC 분석(또는 의심스러울 경우엔 HPLC 분석)이 주된 양의 출발 물질의 존재를 나타낼 경우, 추가의 설포닐 클로라이드(1.5당량)를 첨가하고 실온에서의 교반을 1시간 동안 지속하였다. 방법 A에 기재된 바와 같이 워크업과 정제를 수행하였다.
방법 D
중간생성물 B의 메틸 리튬에 의한 탈프로톤화에 이어서 방향족 설포닐 클로라이드와의 반응에 의해 중간생성물 C 유형 화합물을 얻었고, 이것을 에탄올의 존재 하에 4M 염산/다이옥산을 이용해서 탈보호하여 화학식 I의 화합물을 수득하였다.
방법 E
방법 E는 R5가 지방족기를 지니지 않는 경우에 적용된다. 중간생성물 B의 지방족 설포닐 클로라이드와의 반응을 클로로포름(CHCl3)/아세톤 중 트라이에틸아민 및 4-다이메틸아미노피리딘(DMAP)의 존재 하에 50℃에서 수행하여 중간생성물 C 화합물을 얻었고, 이것을 에탄올의 존재 하에 4M 염산/다이옥산을 이용해서 탈보호하여, 화학식 I의 화합물을 수득하였다.
중간생성물들의 제조
중간생성물 1
N-(2-아미노-4,5-다이클로로페닐)티오펜-2-설폰아마이드
CH2Cl2(185㎖) 및 피리딘(45㎖) 중 4,5-다이클로로-o-페닐렌다이아민(CAS RN: 5348-42-5)(15.78g, 89.14m㏖)의 빙냉 용액에 CH2Cl2(40㎖) 중 2-티오펜설포닐 클로라이드(17.1g, 93.62m㏖, 1.05당량)의 용액을 첨가하였다. 이 혼합물(흑색 용액)을 교반하고, 실온까지 하룻밤(냉각욕을 제거하지 않고) 가온시키고 나서, EtOAc에 첨가하고, 포화 수성 NaHCO3 용액으로 세척하였다. 수층을 EtOAc로 2회 추출하고, 유기층을 합하여 건조(Na2SO4)시키고 나서 농축시켰다. 조질의 생성물을 10g 규모의 시도를 유사하게 수행된 조질의 생성물과 배합하여, 실리카겔(헥산/EtOAc 8:2 내지 6:4, 크로마토그래피는 동일한 용리액을 이용한 혼합 분획으로 반복함) 상에서의 크로마토그래피에 의해 중간생성물 1(31.5g, 67%)을 갈색 고체로서 수득하였다.
C10H8Cl2N2O2S2 (323.22). MS (ESI+): 325/323 [M+H]+. 1H-NMR (DMSO-d6): δ ppm 9.8-9.5 (br. 신호, 1H); 7.95 (dd, J = 1.4, 5.0, 1H); 7.50 (dd, J = 1.4, 3.7, 1H); 7.16 (dd, J = 3.8, 5.0, 1H); 6.87, 6.85 (2s, 2×1H); 5.5-5.25 (br. s, 2H).
중간생성물 2
N-(2-아미노-4,5-다이클로로페닐)-N-(에톡시메틸)티오펜-2-설폰아마이드
THF(90㎖) 및 DMF(30㎖) 중 중간생성물 1(3.24g, 10.02m㏖)의 빙냉 용액에 NaH(미네랄 오일 중 약 60%, 0.6g, 약 15m㏖, 1.5당량, 가스 방출, 갈색 용액)를 첨가하였다. 이 혼합물을 0℃에서 30분 동안 교반하고(5분 후 암흑색으로 됨) 나서, 1-클로로메틸 에틸 에터(1.02㎖, 약 1.04g, 11m㏖, 1.1당량)의 용액을 0℃에서 적가하였다. 갈색을 띤 담녹색 혼합물을 0℃에서 1시간 동안 교반하고 나서, 포화 수성 NaHCO3 용액(약 10㎖)을 0℃에서 첨가하였다. 이 혼합물을 농축(회전 증발기)시키고, 물을 첨가하고 나서, EtOAc로 추출하였다. 유기층을 물(2×) 및 염수로 세척하고, 건조(Na2SO4) 후 농축시켰다. 조질의 생성물을 실리카겔(CH2Cl2/MeOH) 상에 흡수시키고, 실리카겔(헥산/아세톤 90:10 내지 88:12 내지 86:14 내지 84:16 내지 82:18 내지 80:20) 상에서의 크로마토그래피에 의해 중간생성물 2(2.4g, 63%)를 갈색 고체로서 수득하였다.
C13H14Cl2N2O3S2 (381.30). MS (ESI+): 383/381 [M+H]+. 1H-NMR (DMSO-d6): δ ppm 8.05 (dd, J = 0.5, 4.9, 1H); 7.65 (dd, J = 0.5, 3.7, 1H); 7.24 (dd, J = 3.8, 5.0, 1H); 6.92, 6.72 (2s, 2×1H); 5.60 (br. s, 2H, D2O에 의한 처리 시 교환됨); 5.20-5.05 (br. 신호, 1H); 4.78-4.62 (br. 신호, 1H); 3.54 (q, J = 7.0, 2H); 1.09 (t, J = 7.0, 3H).
중간생성물
3
N-(4,5-다이클로로-2-(3-클로로-4-플루오로페닐설폰아마이도)페닐)-N-(에톡시메틸)티오펜-2-설폰아마이드
방법 D에 따른 설폰아마이드 형성: THF(1㎖) 중 중간생성물 2(70㎎, 0.184m㏖)의 빙냉 용액에 MeLi(Et2O 중 1.6M, 0.25㎖, 약 0.4m㏖, 2.2당량)를 적가하였다. 암녹색 혼합물을 0℃에서 15분 동안 교반하고 나서, 방향족 설포닐 클로라이드의 용액, 예를 들어: THF(1㎖) 중 3-클로로-4-플루오로벤젠설포닐 클로라이드(63.1㎎, 0.275m㏖, 1.5당량)를 0℃에서 적가하였다. 오렌지색 용액을 0℃에서 40분, 그리고 실온에서 하룻밤 교반하였다. MeOH를 실온에서 첨가하고, 이 혼합물을 농축시켰다. 역상 분취 HPLC(산성 이동상)에 의해 정제시켜 중간생성물 3(37㎎, 35%)을 담황색 고체로서 수득하였다.
1H-NMR (DMSO-d6): δ ppm 10.6-10.35 (br. 신호, 1H); 8.14 (dd, J = 2.1, 6.7, 1H); 8.08 (dd, J = 1.3, 5.0, 1H); 7.94-7.89 (m, 1H); 7.67 (t, J = 8.9, 1H); 7.60 (s, 1H); 7.56 (dd, J = 1.3, 3.8, 1H); 7.23 (dd, J = 3.9, 4.9, 1H); 6.86 (s, 1H); 5.4-5.0 (br. 신호, 1H); 4.5-4.1 (br. 신호, 1H); 3.41 (부분적으로 가리워지고, 부분적으로 분해된 q, J = 7.0, 2H); 1.04 (t, J = 7.0, 3H).
중간생성물 4
벤조퓨란-2-설폰산 (5-클로로-2-나이트로-페닐)-아마이드
건조 DMF(130㎖) 중 5-클로로-2-나이트로아닐린(8.00g, 46.36m㏖)의 -10℃ 냉각된 황색 용액에 Ar 하에 수소화나트륨 60%(9.27g, 231.79m㏖)를 첨가하였다. 얻어진 적색 현탁액을 -10℃에서 10분 동안 교반하였다. 건조 DMF(50㎖) 중 1-벤조퓨란-2-설포닐 클로라이드(12.05g, 55.63m㏖)의 용액을 적가 깔때기를 이용해서 -10℃에서 (10분의 첨가, 발열 반응, 최대 온도의 첨가는 0℃였고, DMF 5㎖로 상기 깔때기를 헹굼) 적가하였다. 얻어진 오렌지색 현탁액을 -10℃에서 30분 동안 교반하였다(갈색으로 변색). 이 반응 혼합물을 절반 포화된 NaHCO3 용액(400㎖)으로 반응중지시키고(quenched), 생성물을 EtOAc(1×650㎖ 및 4×300㎖)로 5회 추출하였다. 유기층을 합하여 Na2SO4 상에서 건조시키고, 여과 후, 그 여과액을 증발시켜 건조시켰다. 조질의 생성물을 합하여 해당 조질의 생성물을 8g 규모의 시도로 마찬가지로 수행하여 오렌지색 오일 61.82g을 얻었고, 이것을 MPLC(조질물을 CH2Cl2/MeOH 중에 용해시키고, 실리카겔, 칼럼 D, 프로그램 3 상에서 5회 예비흡착시킴)에 의해 정제시켜 중간생성물 4(28.91g, 출발 물질을 합한 것에 의거한 수율 88%)를 황색 고체로서 수득하였다.
C14H9ClN2O5S (352.75). HPLC-MS (염기성 이동상, ESI-): tR = 1.31분, 350.7 [M-H]-. 1H-NMR (DMSO-d6): 7.70 (ddd, J = 0.6, 1.3, 7.8, 1H); 7.60 (dd, J = 0.8, 8.3, 1H); 7.52-7.47 (m, 2H); 7.39 (m, 1H); 7.28 (m, 1H); 7.18 (s, 1H); 6.75 (d, J = 8.3, 1H).
중간생성물 5
벤조퓨란-2-설폰산 (2-아미노-5-클로로-페닐)-아마이드
THF(55㎖) 및 MeOH(285㎖) 중 중간생성물 4(14.41g, 40.85m㏖)의 오렌지색 용액에 포화 수성 NH4Cl 용액(285㎖, 출발 물질의 석출)에 이어서 냉수욕(20℃) 중에서 아연(20.03g, 306.38m㏖)을 첨가하였다. 얻어진 현택액을 20분 동안 실온에서 교반하였다(갈색에서 암녹색으로 변하였다). EtOAc(400㎖) 및 포화 수성 NH4Cl 용액(400㎖)을 첨가하였다. 현탁액 중의 고체를 셀라이트의 패드를 통해서 여과시키고 EtOAc(3×250㎖)로 세척하고 나서, 포화 수성 NH4Cl 용액(3×200㎖)으로 세척하였다. 그 여과액을 진탕시키고 유기층을 합하여 Na2SO4 상에서 건조시키고 증발시켜 건조시켰다. 잔류물을 CH2Cl2 중에 용해시키고, 실리카의 패드를 통해 여과시킨 후, CH2Cl2/MeOH 9/1로 3회 세척하고 나서 증발시켜 건조시켰다. 조질의 생성물을 합하여, 해당 조질의 생성물을 14.41g 규모의 시도로 마찬가지로 수행하여 적색 발포체 27.23g을 남겼다. 조질의 발포체를 CH2Cl2/MeOH 99/1에 용해시키자, 고체가 석출되었다. 이 혼합물을 증발시켜 건조시키고, EtOAc/MeOH의 혼합물에 재용해시켰다. 나머지 고체를 여과 제거하였다. 그 여과액을 실리카겔 상에 예비흡착시키고, 99/1 내지 97/3의 CH2Cl2/MeOH로 용리시키는 실리카겔 상에서의 플래시 크로마토그래피에 의해 정제시켜 불순한 갈색 고체 20.25g을 얻었다. 이 생성물을 MPLC(조질물을 CH2Cl2/MeOH에 용해시키고, 실리카겔, 칼럼 D, 프로그램 7 상에서 5회 예비 흡착시킴)에 의해 재정제시켜 중간생성물 5(18.18g, 출발 물질을 합한 것에 의거한 수율 69%)를 베이지색 고체로서 수득하였다.
C14H11ClN2O3S (322.76). HPLC-MS (산성 이동상, ESI+): tR = 1.93분, 323/325 [M+H]+. 1H-NMR (DMSO-d6): 10.7-9.3 (br. 신호, 약 1H); 7.75 (m, 2H); 7.60-7.50 (m, 2H); 7.39 (m, 1H); 6.96 (dd, J = 2.5, 8.7, 1H); 6.81 (d, J = 2.5, 1H); 6.62 (d, J = 8.7, 1H), 6.9-5.4 (br. 신호, 약 2H).
중간생성물 6
벤조퓨란-2-설폰산 (4-클로로-2-나이트로-페닐)-아마이드
피리딘(3.0㎖) 중 4-클로로-2-나이트로아닐린(CAS RN: 89-63-4)(0.52g, 3.0m㏖)의 용액에 벤조퓨란-2-설포닐 클로라이드(0.65g, 3.0m㏖)를 첨가하고, 이 혼합물을 실온에서 64시간 동안 교반하였다. 더욱 벤조퓨란-2-설포닐 클로라이드(0.65g, 3.0m㏖) 및 피리딘(3.0㎖)을 첨가하고, 이 반응물을 100℃까지 4시간 동안 가열하고, 실온까지 냉각시키고 나서, 얼음과 6M HCl(20㎖)의 혼합물 상에 부었다. 얻어진 현택액을 여과시키고 H2O로 세척 후, 얻어진 케이크를 EtOAc에 용해시키고, 염수로 세척하고 나서, Na2SO4 상에서 건조시키고, 농축시켜 갈색 고체 1.28g을 얻었다. 이 고체를 MeOH/THF(40㎖/10㎖)에 용해시키고, 4M NaOH(4㎖)로 100℃에서 15분 동안 처리하고 나서, 진공 중 농축시켰다. 잔류물을 냉 1M HCl로 반응중지시키고 나서, EtOAc(×2)로 추출하였다. 유기층을 합하여 염수로 세척하고, Na2SO4 상에서 건조 후, 농축시켰다. 뜨거운 EtOH로부터 재결정시켜 중간생성물 6을 0.68g(64%) 수득하였다.
1H-NMR (600 ㎒, CDCl3) δ ppm 10.00 (s, 1 H), 8.13 (d, J=2.3 ㎐, 1 H), 7.93 (d, J=9.1 ㎐, 1 H), 7.64 - 7.68 (m, 1 H), 7.58 (dd, J=9.0, 2.5 ㎐, 1 H), 7.45 - 7.53 (m, 3 H), 7.34 (ddd, J=7.9, 6.9, 1.0 ㎐, 1 H).
중간생성물 7
벤조퓨란-2-설폰산 (2-아미노-4-클로로-페닐)-아마이드
MeOH(25㎖) 및 포화 수성 NH4Cl(25㎖) 중 중간생성물 6(217㎎, 0.61m㏖)의 현탁액에 아연 더스트(1.0g, 15.4m㏖)를 첨가하였다. 이 반응물을 45분 동안 실온에서 교반하였다. HOAc(1.0㎖) 및 아연 더스트(1.0g, 15.4m㏖)를 첨가하고 나서, 이 반응물을 더욱 45분 동안 교반하고 여과시켰다. 그 여과액을 EtOAc(×2)로 추출하였다. 유기층을 합하여 염수로 세척하고, Na2SO4 상에서 건조 후 농축시켰다. 조질의 생성물을 실리카겔(25% EtOAc-헥산) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 중간생성물 7을 158㎎(79%) 수득하였다.
1H-NMR (600 ㎒, CDCl3) δ ppm 7.65 (dt, J=7.4, 0.8 ㎐, 1 H), 7.57 - 7.61 (m, 1 H), 7.50 (ddd, J=8.4, 7.1, 1.2 ㎐, 1 H), 7.35 (ddd, J=8.0, 7.3, 0.9 ㎐, 1 H), 7.30 (d, J=0.9 ㎐, 1 H), 6.70 (d, J=2.3 ㎐, 1 H), 6.59 (d, J=8.5 ㎐, 1 H), 6.45 - 6.48 (m, 1 H), 6.32 (s, 1 H), 4.17 (br. s., 2 H).
중간생성물 8
티오펜-2-설폰산 (3-나이트로-피리딘-2-일)-아마이드
DMSO(4㎖) 중 2-클로로-3-나이트로-피리딘(CAS RN: 5470-18-8, 0.64g, 4.0m㏖)의 용액에 티오펜-2-설폰산 아마이드(CAS RN: 6339-87-3, 0.33g, 2.0m㏖) 및 K2CO3(0.55g, 4.0m㏖)를 첨가하였다. 이 혼합물을 60℃에서 24시간 동안 교반하고, EtOAc로 희석 후, 1M HCl, 염수로 추출하고, Na2SO4 상에서 건조시키고 나서 진공 중 농축시켰다. 조질의 생성물을 실리카겔(헥산류 중 25%-40% EtOAc) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 중간생성물 8(0.50g, 87%)을 황색 분말로서 수득하였다.
1H NMR (클로로포름-d) δ ppm: 10.27 (br. s, 1H), 8.63 (dd, J = 4.5, 1.6 ㎐, 1H), 8.53 (dd, J = 8.2, 1.8 ㎐, 1H), 8.00 (dd, J = 3.8, 1.5 ㎐, 1H), 7.67 (dd, J = 5.0, 1.5 ㎐, 1H), 7.13 - 7.19 (m, 1H), 7.08 - 7.12 (m, 1H).
중간생성물 9
티오펜-2-설폰산 (5-클로로-3-나이트로-피리딘-2-일)-아마이드
DMSO(2㎖) 중 2-브로모-5-클로로-3-나이트로-피리딘(CAS RN: 75806-86-9, 360㎎, 1.5m㏖)의 용액에 티오펜-2-설폰산 아마이드(CAS RN: 6339-87-3, 165㎎, 1.0m㏖) 및 K2CO3(276㎎, 2.0m㏖)를 첨가하였다. 이 혼합물을 60℃에서 24시간 동안 교반하고, EtOAc로 희석하고 나서, 1M HCl, 염수로 추출하고, Na2SO4, 상에서 건조시킨 후, 진공 중 농축시켰다. 조질의 생성물을 실리카겔(헥산류 중 0%-100% EtOAc) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 중간생성물 9(245㎎, 77%)를 담갈색 고체로서 수득하였다.
1H NMR (메탄올-d4) δ 8.57 - 8.63 (m, 2H), 7.95 (dd, J = 4.0, 1.3 ㎐, 1H), 7.86 (dd, J = 5.0, 1.5 ㎐, 1H), 7.14 (dd, J = 5.1, 4.0 ㎐, 1H).
중간생성물 10
티오펜-2-설폰산 (3-아미노-피리딘-2-일)-아마이드
MeOH(30㎖) 및 1M HCl(2㎖) 중 중간생성물 8(175㎎, 0.61m㏖)의 용액에 Pd-C(10%, 65㎎, 0.061m㏖)를 첨가하였다. 이 반응물을 파(Parr) 장치를 이용해서 45 psi H2 하에 3시간 동안 가압하고, 여과 후, 그 여과액을 진공 중 농축시켰다. 조질의 생성물을 실리카겔(헥산류 중 50%-100% EtOAc에 이어서, 2:98 Et3N:EtOAc, 그 후 2:20:80 Et3N:MeOH:CH2Cl2) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 중간생성물 10(157㎎, 84%)을 회백색 고체로서 수득하였다.
1H NMR (클로로포름-d) δ 7.61 (dd, J = 3.7, 1.3 ㎐, 1H), 7.44 (dd, J = 5.0, 1.2 ㎐, 1H), 6.96 - 7.03 (m, 2H), 6.83 (dd, J = 7.6, 1.5 ㎐, 1H), 6.56 (dd, J = 7.6, 6.2 ㎐, 1H).
중간생성물 11
티오펜-2-설폰산 (3-아미노-5-클로로-피리딘-2-일)-아마이드
MeOH(15㎖) 중 중간생성물 9(111㎎, 0.35m㏖)의 용액에 수성 NH4Cl(15㎖) 및 아연 더스트(0.56g, 8.7m㏖)를 첨가하였다. 이 혼합물을 실온에서 2시간 동안 교반하고, 여과 후, EtOAc로 추출하였다. 유기층을 염수로 세척하고, Na2SO4 상에서 건조시킨 후, 진공 중 농축시켰다. 조질의 생성물을 실리카겔(헥산류 중 30%-100% EtOAc, 이어서 CH2Cl2 중 10% MeOH) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 중간생성물 11(75㎎, 75%)을 수득하였다. C9H8ClN3O2S2 (289.8). MS (ESI-): 288/290/ [M-H]-.
중간생성물 12
N-(4,5-다이클로로-2-(2-메틸프로필설폰아마이도)페닐)-N-(에톡시메틸)
티오펜-2-설폰아마이드
설폰아마이드 형성: CHCl3(0.8㎖) 및 아세톤(0.8㎖) 중 중간생성물 2(80㎎, 0.21m㏖) 및 DMAP(5.1㎎, 0.042m㏖, 0.2당량)의 용액에 아이소뷰탄설포닐 클로라이드(32.9㎕, 약 39㎎, 0.25m㏖, 1.2당량)를 실온에서 첨가하고 나서, Et3N(87.2㎕, 약 63㎎, 0.62m㏖, 3당량)를 첨가하였다. 얻어진 오렌지색-갈색 용액을 50℃에서 하룻밤 교반하였다. 물 및 EtOAc를 실온에서 첨가하고 나서, EtOAc에 의해 추출하였다. 유기층을 건조(Na2SO4)시키고, 여과 후, 농축시켰다. 실리카겔(헥산/CH2Cl2/Et2O 5:5:0.5 내지 5:5:1) 상에서의 크로마토그래피에 의해 대응하는 유형의 중간생성물 12 생성물(43㎎, 41%)을 담황색 오일로서 수득하였다.
1H-NMR (CDCl3): δ ppm 7.85 (s, 1H); 약 7.85-7.84 (부분적으로 가리워진 신호, 1H); 7.74 (dd, J = 1.3, 5.0, 1H); 7.54 (dd, J = 1.3, 3.8, 1H); 7.15 (dd, J = 3.8, 5.0, 1H); 7.00 (s, 1H); 5.05-4.88 (br. 신호, 2H); 3.75-3.60 (br. 신호, 2H); 3.04 (d, J = 6.6, 2H); 2.43-2.30 (헵텟(heptet), 1H); 1.28 (t, J = 7.0, 3H); 1.14 (d, J = 6.7, 6H).
본 발명의 구체적인 화합물들의 제조:
화합물 1
N-(4,5-다이클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)
티오펜-2-설폰아마이드
중간생성물 3(47㎎, 0.082m㏖) 및 EtOH(0.2㎖)에 4M HCl/다이옥산(1㎖)을 실온에서 첨가하였다. 이 용액을 실온에서 42시간 동안 교반하고 나서 농축시켰다. 실리카겔(CH2Cl2/MeOH 9:1) 상에서의 크로마토그래피에 의해 화합물 1(24.9㎎, 59%)을 회백색 고체로서 수득하였다.
C16H10Cl3FN2O4S3 (515.81). HPLC-MS (산성 이동상, ESI-): tR = 2.14분, 517/515/513 [M-H]-. 1H-NMR (DMSO-d6): δ ppm 약 10.5-약 9 (br. 신호, 약 1H); 7.99-7.95 (m, 2H); 7.74-7.69 (m, 1H); 7.63 (d, J = 8.9, 1H); 7.58-7.55 (m, 1H); 7.30 (s, 1H); 7.17 (dd, J = 3.8, 5.0, 1H); 7.15 (s, 1H).
화합물 2
N-{4,5-다이클로로-2-[(아이소뷰틸설포닐)아미노]페닐}티오펜-2-설폰아마이드
EtOH(0.2㎖) 중 중간생성물 12(42㎎, 0.084m㏖)에 4M HCl/다이옥산(2㎖)을 실온에서 첨가하였다. 이 용액을 실온에서 72시간 동안 교반하고 나서 농축시켰다. 실리카겔(CH2Cl2/MeOH 95:5 내지 9:1) 상의 크로마토그래피에 의해 화합물 2(29.8㎎, 80%)를 백색 고체로서 수득하였다.
C14H16Cl2N2O4S3 (443.39). HPLC-MS (염기성 이동상, ESI-): tR = 1.66분, 443/441 [M-H]-. 1H-NMR (CDCl3): δ ppm 7.71 (dd, J = 1.3, 5.0, 1H); 7.65 (s, 1H); 7.55 (dd, J = 1.3, 3.8, 1H); 7.14 (dd, J = 3.8, 5.0, 1H); 7.05 (s, 1H); 6.97, 6.96 (2 부분적으로 분리된 s, 2×1H); 3.02 (d, J = 6.6, 2H); 2.42-2.28 (헵텟, 1H); 1.14 (d, J = 6.6, 6H).
화합물 3
N-(4,5-다이클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)
티오펜-2-설폰아마이드
중간생성물 1로부터의 방법 C(수율 18%)에 다른 제조
C16H10Cl2F2N2O4S3 (499.36).
HPLC-MS (산성 이동상, ESI-): tR = 2.16분, 499/497 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.4-약 9.3 (br. 신호, 약 2H); 8.00 (dd, J = 1.3, 5.0, 1H); 7.68 (tt, J = 2.3, 9.2, 1H); 7.59 (dd, J = 1.3, 3.8, 1H); 7.54-7.43 (m, 2H); 7.31 (s, 1H); 7.18 (dd, J = 3.8, 5.0, 1H); 7.13 (s, 1H).
화합물 4
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,4-다이메틸-
1,3-티아졸-5-설폰아마이드
중간생성물 1로부터의 방법 A(수율 10%)에 따른 제조
C15H13Cl2N3O4S4 (498.45).
HPLC-MS (산성 이동상, ESI-): tR = 1.98분, 498/496 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.3-9.3 (br. 신호, 약 2H); 7.99 (dd, J = 1.3, 5.0, 1H); 7.60 (dd, J = 1.3, 3.8, 1H); 7.31, 7.27 (2s, 2×1H); 7.18 (dd, J = 3.8, 5.0, 1H); 2.62, 2.33 (2s, 2×3H).
화합물 5
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드
중간생성물 1로부터의 방법 A(수율 18%)에 따른 제조
C15H13Cl2N3O5S3 (482.38).
HPLC-MS (산성 이동상, ESI-): tR = 2.01분, 482/480 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.3-약 9.5 (br. 신호, 약 2H); 8.00 (dd, J = 1.2, 4.9, 1H); 7.61 (dd, J = 1.3, 3.8, 1H); 7.31, 7.21 (2s, 2×1H); 7.19 (dd, J = 3.9, 5.0, 1H); 2.40, 2.19 (2s, 2×3H).
화합물 6
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드
중간생성물 1로부터의 방법 A(수율 24%)에 따른 제조.
C18H13Cl2N3O5S3 (518.41).
HPLC-MS (산성 이동상, ESI-): tR = 1.88분, 518/516 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.84 (s, 1H); 약 10.1-약 10.65 (br. 신호, 약 1H); 약 10.65-약 9.3 (br. 신호, 약 1H); 7.99 (신호가 d로서 나타남, "J" = 4.9, 1H); 7.60-7.55 (m, 3H); 7.28, 7.19 (2s, 2×1H); 7.17 (dd, J = 3.8, 4.9, 1H); 6.93 (d, J = 8.7, 1H); 3.55 (s, 2H).
화합물 7
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드
중간생성물 1로부터의 방법 A(수율 31%)에 따른 제조.
C17H11Cl2N3O6S3 (520.39).
HPLC-MS (염기성 이동상, ESI-): tR = 1.21분, 520/518 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 12.4-약 11.95 (br. 신호, 1H); 약 10.1-약 9.3 (br. 신호, 2H); 7.98 (dd, J = 1.3, 5.0, 1H); 7.65 (d, J = 1.6, 1H); 7.56-7.52 (m, 2H); 7.31 (s, 1H); 7.23 (d, J = 8.3, 1H); 7.16 (dd, J = 3.7, 4.9, 1H); 7.15 (s, 1H).
화합물 8
4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산
중간생성물 1로부터의 방법 A(수율 26%)에 따른 제조.
C17H12Cl2N2O6S3 (507.39).
HPLC-MS (산성 이동상, ESI-): tR = 1.78분, 507/505 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.3-10.05 (br. 신호, 1H); 9.58 (s, 1H); 8.06 (s, 1H); 7.88 (부분적으로 분해된 dd, J = 0.9, 5.0, 1H); 7.75 (s, 4H); 7.46-7.45 (m, 2H); 7.06-7.03 (t-유사 신호, 1H).
화합물 9
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시벤조산
중간생성물 1로부터의 방법 B(수율 31%)에 따른 제조.
C18H14Cl2N2O7S3 (537.41).
HPLC-MS (염기성 이동상, ESI-): tR = 1.16분, 537/535 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.80 (s, 1H); 10.4-10.15 (br. 신호, 1H); 8.73 (s, 1H); 8.30 (d, J = 2.3, 1H); 8.05 (dd, J = 1.4, 5.0, 1H); 7.81 (dd, J = 2.3, 8.6, 1H); 7.55 (dd, J = 1.4, 3.8, 1H); 7.26-7.21 (m, 2H); 6.71 (s, 1H); 4.14 (s, 3H).
화합물 10
N-(4,5-다이클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드
중간생성물 1로부터의 방법 A(수율 40%)에 따른 제조.
C18H16Cl2N2O6S3 (523.43).
HPLC-MS (염기성 이동상, ESI-): tR = 1.58분, 523/521 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.1-약 9.7 (br. 신호, 약 1H); 9.16 (br. s, 1H); 7.99 (신호가 부분적으로 분해된 d로서 나타남, "J" = 4.2, 1H); 7.62 (d, J = 8.8, 1H); 7.54 (신호가 부분적으로 분해된 d로서 나타남, "J" = 2.5, 1H); 7.39 (s, 1H); 7.17 (t-유사 신호, "J" = 4.3, 1H); 7.04 (s, 1H); 6.73 (d, J = 2.3, 1H); 6.61 (dd, J = 2.3, 8.8, 1H); 3.91, 3.83 (2s, 2×3H).
화합물 11
N-[4,5-다이클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
제법: 중간생성물 1로부터의 DIPEA(3당량), CH2Cl2, 실온(수율 76%).
C17H14Cl2N2O6S4 (541.47).
HPLC-MS (산성 이동상, ESI-): tR = 1.99분, 541/539 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.1-약 9 (2 br. 신호들, 약 2H); 8.27 (부분적으로 분해된 dd, J = 1.2, 7.9, 1H); 8.02-7.94 (m, 3H); 7.89-7.84 (m, 1H); 7.63 (s, 1H); 7.44 (dd, J = 1.4, 3.8, 1H); 7.16 (dd, J = 3.8, 5.0, 1H); 6.68 (br. s, 1H); 3.51 (s, 3H).
화합물 12
메틸 4-[({4,5-다이클로로-[(2티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트
중간생성물 1로부터의 방법 A(수율 33%)에 따른 제조.
C18H14Cl2N2O6S3 (521.42).
HPLC-MS (염기성 이동상, ESI-): tR = 1.58분, 521/519 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.2-약 9.5 (br. 신호, 약 2H); 8.12 (d, J = 8.6, 2H); 7.98 (dd, J = 1.3, 5.0, 1H); 7.87 (d, J = 8.7, 2H); 7.55 (dd, J = 1.4, 3.8, 1H); 7.24, 7.20 (2s, 2×1H); 7.16 (dd, J = 3.8, 5.0, 1H); 3.90 (s, 3H).
화합물 13
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2H-크로멘-6-설폰아마이드
중간생성물 1로부터의 방법 A(수율 51%)에 따른 제조.
C19H12Cl2N2O6S3 (531.41).
HPLC-MS (산성 이동상, ESI-): tR = 2.04분, 531/529 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.1-9.5 (br. 신호, 2H); 8.21 (d, J = 2.3, 1H); 8.18 (d, J = 9.7, 1H); 7.98 (dd, J = 1.3, 5.0, 1H); 7.89 (dd, J = 2.3, 8.8, 1H); 7.59-7.55 (m, 2H); 7.33 (s, 1H); 7.16 (dd, J = 3.8, 5.0, 1H); 7.15 (s, 1H); 6.64 (d, J = 9.6, 1H).
화합물 14
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}이미다조[2,1-b][1,3]티아졸-5-설폰아마이드
중간생성물 1로부터의 방법 C(수율 8%)에 따른 제조.
C15H9Cl3N4O4S4 (543.88).
HPLC-MS (산성 이동상, ESI-): tR = 1.99분, 545/543/ 541 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.4-약 9.3 (br. 신호, 약 1H); 7.98 (dd, J = 1.2, 5.0, 1H); 7.91, 7.63 (2d, J = 4.5, 2×1H); 7.56 (dd, J = 1.3, 3.8, 1H); 7.31 (s, 1H); 7.16 (dd, J = 3.9, 4.9, 1H); 7.12 (s, 1H).
화합물 15
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,5-다이메틸퓨란-3-설폰아마이드
중간생성물 1로부터의 방법 A(수율 40%)에 따른 제조.
C16H14Cl2N2O5S3 (481.39).
HPLC-MS (산성 이동상, ESI-): tR = 2.15분, 481/479 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.1-약 9.7 (br. 신호, 약 1H); 약 9.7-약 9.4 (br. 신호, 1H); 8.01 (dd, J = 1.4, 5.0, 1H); 7.59 (dd, J = 1.4, 3.8, 1H); 7.30, 7.28 (2s, 2×1H); 7.18 (dd, J = 3.8, 5.0, 1H); 6.15 (신호가 부분적으로 분해된 d로서 나타남, "J" = 1.0, 1H); 2.28, 2.21 (2s, 2×3H).
화합물 16
N-[4,5-다이클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드
중간생성물 1로부터의 방법 A(수율 51%)에 따른 제조.
C21H18Cl2N4O4S3 (557.49).
HPLC-MS (염기성 이동상, ESI-): tR = 1.61분, 557/555 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10-약 9.5 (br. 신호, 2H); 7.97 (dd, J = 1.3, 5.0, 1H); 7.81, 7.75 (2d, J = 9.0, 2×2H); 7.56 (dd, J = 1.3, 3.8, 1H); 7.27, 7.22 (2s, 2×1H); 7.16 (dd, J = 3.8, 5.0, 1H); 6.15 (s, 1H); 2.38, 2.19 (2s, 2×3H).
화합물 17
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-3-설폰아마이드
중간생성물 1로부터의 방법 A(수율 57%)에 따른 제조.
C14H12Cl2N4O4S3 (467.37).
HPLC-MS (염기성 이동상, ESI-): tR = 1.41분, 467/465 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10-9.6 (br. 신호, 2H); 7.99 (dd, J = 1.3, 5.0, 1H); 7.91 (d, J = 2.3, 1H); 7.60 (dd, J = 1.3, 3.8, 1H); 7.47, 7.32 (2s, 2×1H); 7.17 (dd, J = 3.8, 5.0, 1H); 6.64 (d, J = 2.3, 1H); 3.93 (s, 3H).
화합물 18
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-4-설폰아마이드
중간생성물 1로부터의 방법 A, 15분(수율 45%)에 따른 제조.
C19H15Cl2N3O4S3 (516.44).
HPLC-MS (산성 이동상, ESI-): tR = 2.04분, 516/514 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10-약 9.5 (br. 신호, 약 2H); 7.96 (dd, J = 1.2, 5.0, 1H); 7.82 (d, J = 7.8, 1H); 7.59 (d, J = 3.1, 1H); 7.52 (부분적으로 분해된 dd, J = 0.8, 7.5, 1H); 7.49 (부분적으로 분해된 dd, J = 1.2, 3.9, 1H); 7.30 (t, J = 7.3, 1H); 7.21 (s, 1H); 7.14 (dd, J = 3.8, 5.0, 1H); 7.10 (s, 1H); 6.74 (부분적으로 분해된 dd, J = 0.7, 3.1, 1H); 3.86 (s, 3H).
화합물 19
N-(4,5-다이클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드
중간생성물 1로부터의 방법 A(수율 44%)에 따른 제조.
C16H14Cl2N2O4S4 (497.46).
HPLC-MS (산성 이동상, ESI-): tR = 2.20분, 497/495 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.2-약 9.3 (2 br. 신호들, 약 2H); 8.00 (신호가 부분적으로 분해된 d로서 나타남, "J" = 4.0, 1H); 7.60 (신호가 부분적으로 분해된 d로서 나타남, "J" = 2.7, 1H); 7.28 (s, 1H); 7.18 (부분적으로 가리워진 dd, J = 3.8, 5.0, 1H); 약 7.16 (s, 1H); 6.84 (신호가 부분적으로 분해된 d로서 나타남, "J" = 1.1, 1H); 2.38, 2.35 (2s, 2×3H).
화합물 20
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드
중간생성물 1로부터의 방법 A(수율 33%)에 따른 제조.
C15H11Cl2N3O4S3 (464.37).
HPLC-MS (산성 이동상, ESI-): tR = 1.94분, 464/462 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.4-약 9.2 (br. 신호, 약 1H); 8.88 (d, J = 1.8, 1H); 8.84 (dd, J = 1.5, 4.8, 1H); 8.11 (ddd, J = 1.7, 2.5, 8.1, 1H); 7.98 (dd, J = 1.3, 5.0, 1H); 7.62 (dd, J = 4.5, 7.8, 1H); 7.54 (dd, J = 1.4, 3.8, 1H); 7.29 (s, 1H); 7.17 (s, 1H); 7.167 (부분적으로 가리워진 dd, J 3.8, 5.0, 1H).
화합물 21
N-{(4,5-다이클로로-2-[(3,5-다이클로로-4-하이드록시페닐)설포닐]
아미노}페닐)티오펜-2-설폰아마이드
중간생성물 1로부터의 방법 A(수율 19%)에 따른 제조.
C16H10Cl4N2O5S3 (548.27).
HPLC-MS (염기성 이동상, ESI-): tR = 1.21분, 549/547/545 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10.8-약 9.1 (br. 신호, 약 2H); 7.99 (dd, J = 1.3, 5.0, 1H); 7.69 (s, 2H); 7.56 (dd, J = 1.4, 3.8, 1H); 7.30 (s, 1H); 7.17 (dd, J = 3.9, 5.0, 1H); 7.15 (s, 1H).
화합물 22
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드
중간생성물 1로부터의 방법 C(수율 32%)에 따른 제조.
C15H14Cl2N4O4S3 (481.40).
HPLC-MS (염기성 이동상, ESI-): tR = 1.44분, 481/479 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 11-약 10 (br. 신호, 약 1H); 9.8-9.5 (br. 신호, 1H); 7.98 (신호가 d로서 나타남, "J" = 5.0, 1H); 7.81 (s, 1H); 7.61 (신호가 d로서 나타남, "J" = 3.7, 1H); 7.53, 7.41 (2s, 2×1H); 7.16 (신호가 t로서 나타남, "J" 4.4, 1H); 3.60, 2.36 (2s, 2×3H).
화합물 23
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸퀴놀린-8-설폰아마이드
중간생성물 1로부터의 방법 A(수율 30%)에 따른 제조.
C20H15Cl2N3O4S3 (528.45).
HPLC-MS (산성 이동상, ESI-): tR = 2.14분, 528/526 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 약 10-약 9.6 (br. 신호, 2H); 9.04 (부분적으로 분해된 d, J = 1.7, 1H); 8.37 (신호가 s로서 나타남, 1H); 8.25 (신호가 t로서 나타남, J = 8.5, 2H); 7.95 (신호가 부분적으로 분해된 d로서 나타남, "J" = 5.2, 1H); 7.73-7.68 (t-유사 신호, "J" 7.7, 1H); 7.58 (s, 1H); 7.43 (미분해된 "d", "J" = 2.5, 1H); 7.14-7.11 (부분적으로 분해된 t-유사 신호, "J" 4.3, 1H); 6.79 (s, 1H); 2.57 (s, 3H).
화합물 24
N-{5-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드
피리딘(2.5㎖) 중 N-(2-아미노-4-클로로페닐)티오펜-2-설폰아마이드(CAS RN: 926205-90-5)(140㎎, ~0.47m㏖)의 용액에 벤조퓨란-2-설포닐 클로라이드(102㎎, 0.47m㏖)를 첨가하고, 이 혼합물을 실온에서 16시간 동안 교반하였다. 더욱 벤조퓨란-2-설포닐 클로라이드(51㎎, 0.24m㏖)를 첨가하고, 이 반응물을 더욱 24시간 동안 교반하고, 진공 중 농축시켜 용매의 대부분을 제거하였다. 잔류하는 걸쭉한 시럽을 6M HCl로 반응중지시키고, H2O로 희석시켰다. 얻어진 현탁액을 여과시키고 H2O(×3)로 세척하였다. 조질의 생성물을 실리카겔(25-50% EtOAc-헥산) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 불순물로 다소 오염된 생성물 43㎎을 얻었다. 이 물질을 CH2Cl2와 함께 분쇄하여 모래색깔 고체를 얻었으며, 이것을 여과시키고 최소량의 CH2Cl2로 헹구어 화합물 24를 23㎎(10%) 수득하였다.
1H-NMR (600 ㎒, CD3OD) δ ppm 7.73 (dd, J=5.0, 1.5 ㎐, 1 H), 7.70 - 7.72 (m, 1 H), 7.60 - 7.63 (m, 1 H), 7.51 (ddd, J=8.5, 7.2, 1.3 ㎐, 1 H), 7.41 (dd, J=3.8, 1.2 ㎐, 1 H), 7.37 (dd, J=1.9, 0.7 ㎐, 1 H), 7.34 - 7.36 (m, 1 H), 7.29 (d, J=2.3 ㎐, 1 H), 7.07 (dd, J=8.8, 2.3 ㎐, 1 H), 7.05 (dd, J=5.0, 3.8 ㎐, 1 H), 6.95 (d, J=8.5 ㎐, 1 H), 4.57 (br. s., 2 H).
화합물 25
N-{4-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드
피리딘(3.0㎖) 중 중간생성물 7(158㎎, 0.49m㏖)의 용액에 티오펜-2-설포닐 클로라이드(90㎎, 0.49m㏖)를 첨가하고, 실온에서 16시간 동안 교반하였다. 용매를 진공 중 제거하고, 잔류물을 실리카겔(25-50% EtOAc-헥산) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 불순물로 다소 오염된 목적으로 하는 생성물 64㎎를 수득하였다. 분취 TLC(50% EtOAc-헥산)에 의한 추가의 정제에 의해 화합물 25를 52㎎(23%) 수득하였다.
1H-NMR (600 ㎒, CD3OD) δ ppm 7.76 (dd, J=5.0, 1.2 ㎐, 1 H), 7.69 (dd, J=7.9, 1.2 ㎐, 1 H), 7.62 (dd, J=8.5, 0.6 ㎐, 1 H), 7.51 (ddd, J=8.4, 7.3, 1.3 ㎐, 1 H), 7.46 (dd, J=3.8, 1.5 ㎐, 1 H), 7.32 - 7.37 (m, 2 H), 7.13 - 7.16 (m, 1 H), 7.06 - 7.11 (m, 3 H).
화합물 26
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,2-다이메틸크로만-6-설폰아마이드
제법: 중간생성물 5로부터의 방법 A(수율 63%)
C25H23ClN2O6S2 (547.04).
HPLC-MS (염기성 이동상, ESI-): tR = 1.55분, 547/545 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.5-9.8 (br. 신호, 약 1H); 9.28 (s, 1H); 7.79 (부분적으로 분해된 dd, J = 0.4, 7.6, 1H); 7.72 (dd, J = 0.8, 8.4, 1H); 7.66 (s, 1H); 7.56 (m, 1H); 7.50 (d, J= 2.3, 1H); 7.41 (m, 1H); 7.32 (dd, J = 2.4, 8.7, 1H); 7.20-7.10 (m, 2H); 7.08 (부분적으로 분해된 dd, J = 0.4, 8.7, 1H); 6.75 (d, J = 8.7, 1H); 2.74 (t, J = 6.6, 2H); 1.76 (t, J = 6.6, 2H); 1.27 (s, 6H).
화합물 27
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드
제법: 중간생성물 5로부터의 방법 A(수율 60%)
C22H16ClN3O5S3 (534.03).
HPLC-MS (염기성 이동상, ESI-): tR = 1.36분, 532/534 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.4-9.8 (br. 신호, 약 1H); 9.8-9.6 (브로드한 신호, 약 1H); 9.59 (s, 1H); 8.50 (d, J = 1.6, 1H); 7.98 (d, J = 8.6, 1H); 7.80-7.70 (m, 3H); 7.62 (s, 1H); 7.56 (m, 1H); 7.40 (m, 1H); 7.14-7.10 (m, 2H); 7.00 (dd, 부분적으로 분해된, J = 1.3, 8.5, 1H); 2.84 (s, 3H).
화합물 28
N-[5-클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드
제법: 중간생성물 5로부터의 방법 A(수율 20%).
C25H19ClN4O5S2 (555.03).
HPLC-MS (산성 이동상, ESI+): tR = 2.11분, 555/557 [M+H]+.
1H-NMR (DMSO-d6): δ ppm 10.6-9.8 (br. 신호, 약 1H); 9.8-9.5 (br. 신호, 약 1H); 8.81 (d, J = 5.3, 1H); 8.56 (t, J = 1.6, 1H); 8.40 (d, J = 7.9, 1H); 7.89 (d, J = 5.3, 1H); 7.82 (m, 1H); 7.76 (d, J = 7.6, 1H); 7.68 (m, 2H); 7.62 (s, 1H); 7.54 (m, 1H); 7.39 (m, 1H); 7.18-7.14 (m, 2H); 7.06 (d, J = 9.1, 1H); 2.70 (s, 3H).
화합물 29
N-{5-클로로-2-[(아이소뷰틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드
제법: 중간생성물 5로부터의 방법 A(수율 11%).
C18H19ClN2O5S2 (442.94).
HPLC-MS (염기성 이동상, ESI-): tR = 1.86분, 441/443 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.8-9.8 (br. 신호, 약 1H); 8.91 (s, 1H); 7.78 (d, J = 7.7, 1H); 7.72 (d, J = 8.4, 1H); 7.66 (s, 1H); 7.56 (m, 1H); 7.44-7.36 (m, 2H); 7.27 (d, J = 8.9, 1H); 7.23 (d, J = 2.4, 1H); 2.84 (d, J = 6.5, 2H); 2.04 (셉투플렛(septuplet), J = 6.7, 1H); 0.91 (d, J = 6.7, 6H).
화합물 30
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아이소퀴놀린-5-설폰아마이드
제법: 중간생성물 5로부터의 방법 A(수율 51%).
C23H16ClN3O5S2 (513.97).
HPLC-MS (산성 이동상, ESI+): tR = 1.86분, 514/516 [M+H]+.
1H-NMR (DMSO-d6): δ ppm 10.4-9.6 (br. 신호, 약 2H); 9.47 (d, J = 0.7, 1H); 8.65 (d, J = 6.2, 1H); 8.45 (d, J = 8.2, 1H); 8.37 (d, J = 6.1, 1H); 8.25 (dd, J = 1.2, 7.4, 1H); 7.76 (m, 2H); 7.69 (dd, J = 0.7, 8.4, 1H); 7.59 (s, 1H); 7.54 (m, 1H); 7.39 (m, 1H); 7.08-7.03 (m, 2H); 6.87 (d, J = 8.7, 1H).
화합물 31
N-(5-클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드
제법: 중간생성물 5로부터의 방법 A(수율 54%)에 따른 제조.
C22H19ClN2O7S2 (522.98).
MS (ESI+): 523 [M+H]+.
1H-NMR (DMSO-d6): δ ppm 10.6-9.8 (br. 신호, 약 1H); 9.02 (s, 1H); 7.78 (d, J = 7.6, 1H); 7.71 (d, J = 8.4, 1H); 7.65 (s, 1H); 7.55 (m, 2H); 7.40 (t, J = 7.5, 1H); 7.15 (s, 2H); 7.01 (부분적으로 분해된 t, J = 1.2, 1H); 6.71 (d, J = 2.2, 1H); 6.56 (dd, J = 2.3, 8.8, 1H); 3.91 (s, 3H); 3.81 (s, 3H).
화합물 32
에틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-3-퓨로에이트
제법: 중간생성물 5로부터의 방법 C(수율 16%).
C21H17ClN2O8S2 (524.95).
HPLC-MS (산성 이동상, ESI-): tR = 2.30분, 523/525 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.9-9.5 (br. 신호, 약 2H); 8.61 (d, J = 0.9, 1H); 7.79 (d, J = 7.4, 1H); 1.71 (dd, J = 0.7, 8.4, 1H); 7.67 (s, 1H); 7.55 (m, 1H); 7.40 (m, 1H); 7.26-7.21 (m, 2H); 7.19 (d, J = 2.2, 1H); 7.13 (d, J = 8.6, 1H); 4.25 (쿼텟(quartet), J = 7.1, 2H); 1.27 (t, J = 7.1, 3H).
화합물 33
N-(5-클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드
제법: 중간생성물 5로부터의 방법 C(수율 30%).
C18H11Cl3N2O5S3 (537.84).
HPLC-MS (염기성 이동상, ESI-): tR = 1.70분, 535/537 [M-H]-.
1H-NMR (DMSO-d6): δ ppm 10.6-9.4 (br. 신호, 약 2H); 7.80 (dd, J = 0.7, 7.8, 1H); 7.73-7.69 (m, 2H); 7.55 (m, 1H); 7.40 (m, 1H); 7.33-7.20 (m, 3H); 7.09 (d, J = 8.7, 1H).
화합물 34
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5,6-다이클로로피리딘-3-설폰아마이드
제법: 중간생성물 5로부터의 방법 C(수율 28%)로부터의 방법 C.
C19H12Cl3N3O5S2 (532.80).
HPLC-MS (산성 이동상, ESI+): tR = 2.36분, 532/534 [M+H]+.
1H-NMR (DMSO-d6): δ ppm 10.7-9.5 (br. 신호, 약 2H); 8.60 (d, J = 2.2, 1H); 8.37 (d, J = 2.2, 1H); 7.80 (d, J = 7.4, 1H); 7.72 (dd, J = 0.7, 8.4, 1H); 7.67 (s, 1H); 7.56 (m, 1H); 7.40 (m, 1H); 7.22 (m, 2H); 7.04 (부분적으로 분해된 dd, J = 0.5, 2.3, 1H).
화합물 35
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시벤조산
제법: 중간생성물 5로부터의 방법 B(수율 17%).
C22H17ClN2O8S2 (536.96).
HPLC-MS (산성 이동상, ESI+): tR = 1.68분, 537/539 [M+H]+.
1H-NMR (DMSO-d6): δ ppm 11.0-10.7 (br. 신호, 약 1H); 10.67 (s, 1H); 8.42 (d, J = 8.9, 1H); 8.29 (d, J = 2.3, 1H); 7.78 (m, 2H); 7.66-7.62 (m, 2H); 1.53 (m, 1H); 7.44-7.36 (m, 2H); 7.23 (d, J = 8.7, 1H); 6.77 (d, J = 2.5, 1H); 4.14 (s, 3H).
화합물 36
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-에톡시벤조산
제법: 중간생성물 5로부터의 방법 B(수율 27%).
C23H19ClN2O8S2 (550.99).
HPLC-MS (산성 이동상, ESI+): tR = 1.77분, 551/553 [M+H]+.
1H-NMR (DMSO-d6): δ ppm 10.9-10.6 (br. 신호, 약 1H); 10.48 (s, 1H); 8.31 (d, J = 8.9, 1H); 8.25 (d, J = 2.3, 1H); 7.79-7.75 (m, 2H); 7.66-7.59 (m, 2H); 7.53 (m, 1H); 7.43-7.36 (m, 2H); 7.22 (d, J = 8.7, 1H); 6.78 (d, J = 2.5, 1H); 4.44 (쿼텟, J = 7.0, 2H); 1.47 (t, J = 6.9, 3H).
화합물 37
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드
피리딘(2㎖) 중 중간생성물 10(72㎎, 0.28m㏖) 용액에 4-클로로-3-트라이플루오로메틸-벤젠설포닐 클로라이드(49㎕, 0.28m㏖)를 첨가하고, 이 반응물을 실온에서 3일 동안 교반하고, 진공 중 농축시켰다. 조질의 생성물을 실리카겔(헥산류 중 50%-75% EtOAc) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시켜 화합물 37(26㎎, 18%)을 수득하였다.
1H NMR (아세톤-d6) δ ppm: 8.27 (d, J = 2.1 ㎐, 1H), 8.14 (dd, J = 8.4, 2.2 ㎐, 1H), 7.97 (dd, J = 7.6, 1.5 ㎐, 1H), 7.83 (dd, J = 6.4, 1.5 ㎐, 1H), 7.78 (d, J = 8.2 ㎐, 1H), 7.71 (dd, J = 5.0, 1.5 ㎐, 1H), 7.51 (dd, J = 3.7, 1.3 ㎐, 1H), 7.05 (dd, J = 5.0, 3.5 ㎐, 1H), 6.88 (dd, J = 7.8, 6.3 ㎐, 1H).
화합물 38
N-[5-클로로-3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드
피리딘(2㎖) 중 중간생성물 11(75㎎, 0.26m㏖)의 용액에 4-클로로-3-트라이플루오로메틸-벤젠설포닐 클로라이드(143㎎, 0.52m㏖)를 첨가하고, 이 반응물을 100℃에서 6시간 동안 교반하고 나서, 진공 중 농축시켰다. 조질의 생성물을 실리카겔(헥산류 중 50%-100% EtOAc) 상에서의 플래시 칼럼 크로마토그래피에 의해 정제시키고 나서 PTLC(EtOAc)에 의해 정제시켜 화합물 38(24㎎, 17%)을 수득하였다.
1H NMR (아세톤-d6) δ ppm: 8.52 (d, J = 8.5 ㎐, 1H), 8.47 (s, 1H), 7.88 - 8.01 (m, 1H), 7.69 (d, J = 8.2 ㎐, 1H), 7.58 (d, J = 4.7 ㎐, 1H), 7.42 - 7.51 (m, 1H), 7.17 - 7.28 (m, 1H), 6.91 - 7.01 (m, 1H).
본 발명의 다른 화합물의 제조에 이용되는 합성 방법이 표 1에 요약되어 있다. 화합물 39 내지 261은 중간생성물 1로부터 출발하여 제조되었다. 화합물 262는 중간생성물 7로부터 제조되었다. 화합물 263 내지 484는 중간생성물 5로부터 출발하여 제조되었다.
생물학적 데이터
CCR2을 안정적으로 발현하는 HEK-Gqi5 세포를 (DMEM 고농도 글루코스, 10% FBS, 1% PSA, 400 ㎍/㎖ 제네티신(geneticin) 및 50 ㎍/㎖ 하이그로마이신 중에서 배양하였다. 적절한 양성 대조군인 케모카인(MCP-1, MIP1A 또는 RANTES)을 FLIPRTetra 상에서 검정된 화합물-유발 칼슘 활성을 선별하기 위한 양성 대조군 작용제로서 이용하였다. EP3 및 멀티프로브(MultiPROBE) 로봇 액체 취급 시스템을 이용해서 384-웰 마이크로플레이트에 약물 플레이트를 준비하였다. 화합물을 합성하고 CCR2 활성에 대해서 테스트하였다.
표 2는 CCR2 수용체에 대한 활성 (IC50) nM을 나타낸다.
Claims (14)
- 하기 화학식 I을 가진 화합물, 그의 거울상이성질체, 부분입체이성질체, 수소화물, 용매화물, 결정 형태, 개별의 이성질체, 호변이성질체 또는 그의 약제학적으로 허용가능한 염:
[화학식 I]
식 중,
R1은 H이고;
R2는 H이며;
R3은 C-R7이고;
R4는 C-R8이며;
R5는 2 티에닐, 페닐, 페닐-4-아세트아마이드, 4-클로로-3-트라이플루오로메틸페닐, -1-메틸-1H-이미다졸, 3-피리딘, 2 아미노페닐, 1,3-다이메틸-1H-피라졸, 1-메틸-1H-피라졸, 1-메틸-1H-이미다졸, 4-(1H-피라졸-1-일)페닐, 1,3-티아졸-4-일)페닐, 4-(1,3-옥사졸-5-일)페닐, 2-(메틸아미노)벤조에이트, 1-메틸-1H-인돌, 2-옥소인돌린, 1-메틸-2,3-다이옥소인돌린, 1-메틸-2-옥소인돌린, 2-퓨란, 4-바이페닐, 3,5-다이플루오로페닐, 3,5-다이클로로페닐, -3,5-다이메틸아이소옥사졸, 4-클로로-2,5-다이플루오로페닐, 4-(2-메틸페녹시)페닐, 5-아이소옥사졸-3-일티오펜, 2,6-다이클로로페닐, 4-(메틸설포닐)페닐, 3,4-다이플루오로페닐, 4-클로로-3-메틸페닐, 2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸, 4-벤조산, 2-메톡시벤조산, 3-사이아노페닐, 4-tert-뷰틸페닐, 1,3-벤조티아졸, 1H-1,2,4-트라이아졸, 2-클로로-1,3-벤조티아졸, 2,4-다이메톡시페닐, 2,5-다이클로로-3-티에닐, 3-메톡시페닐, 3-(메틸설포닐)페닐, 3-클로로-2-메틸페닐, 4페닐프로판산, 2-에톡시벤조산, 2-메틸페닐}아세트아마이드, 3,5-비스(트라이플루오로메틸)페닐, 1H-피라졸, 4-(트라이플루오로메톡시)페닐, 4-(벤질옥시)페닐, 2-클로로-4-플루오로벤조산, 티오펜-2-카복실레이트, 4-플루오로벤조산, 2-클로로-퀴놀린, 2,3-다이하이드로-1H-인덴, 1-나프틸, 1,3-벤조다이옥솔, 3,5-다이클로로-2-하이드록시페닐, 2-벤조퓨란, 퀴놀린, 4-메틸벤조에이트, 2,4-다이메틸-1,3-티아졸, 4-메틸-1,3-티아졸-2-일}아세트아마이드, 5-클로로-8-퀴놀린, 2,4,5-트라이플루오로페닐, 3,4-다이메톡시페닐, 3,5-다이메틸-1H-피라졸, 1-(페닐설포닐)-1H-피롤, N-아세틸인돌린, 1,3,4-옥사아디아졸-2-일-페닐, 3-(1-메틸-1H-피라졸-3-일)페닐, 2-티에닐설포닐)아미노]페닐-4-메틸, 2-옥소-2H-크로멘, 6-페닐-3-피리딘, 2-클로로-4-(트라이플루오로메틸)페닐, 6-페녹시피리딘, 5-페닐티오펜, 2,5-다이메틸-3-티에닐, 2-클로로페닐-4-아세트아마이드, (5-클로로-2,4-다이플루오로페닐, 4-(1-메틸-1H-피라졸-3-일)페닐, 5-메틸-1-벤조티오펜, 2,5-다이메틸퓨란, 4-(피롤리딘-1-일설포닐)페닐, 메틸-2-메틸-3-퓨로에이트, 3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진, 2,4-다이클로로-벤조산, 5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐, 2-메톡시페닐}아세트아마이드, 2-이미다조[2,1-b][1,3]티아졸, 6-몰폴린-4-일피리딘, 3-[(6-메틸피라진-2-일)옥시]페닐, 5-피리딘-2-일티오펜, 3-피리미딘-2-일페닐, 4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진, 6-(다이메틸아미노)-2-나프틸, 2-(메틸설포닐)페닐, 3-메틸-8-퀴놀린, 5-아이소옥사졸-5-일티오펜, 5-(다이메틸아미노)-1-나프틸, 2-클로로-티에닐, 메틸, 에틸, 벤질, 아이소-뷰틸, 2,2-다이메틸크로만, 2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀, 4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진, 4-아세틸-3,4-다이하이드로-2H-1,4-벤즈옥사진, 4-(벤질옥시)페닐, 2,4-다이메틸-1,3-티아졸, 3,5-다이메틸아이소옥사졸, 5-클로로-3-메틸-1-벤조티엔-2-일, 2-클로로-4-플루오로벤조산, 4-메틸-1,3-티아졸-2-일}아세트아마이드, 1H-1,2,4-트라이아졸, 페닐}프로판산, 5-클로로티오펜-2-카복실레이트, 3-페닐아세트아마이드, 2-옥소인돌린, 2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸, 5-아이소옥사졸-3-일-2-티에닐, 2-클로로퀴놀린, 1-(페닐설포닐)-1H-피롤, 2,5-다이클로로-3-티에닐, 5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐, 6-몰폴린-4-일피리딘, 4-메톡시티오펜, 3-퓨릴, 1-메틸-1H-피라졸, 6-클로로이미다조[2,1-b][1,3]티아졸, 3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐, 3-피리미딘-2-일페닐, 1-아세틸-인돌린, 아이소니코티네이트, 3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐, 4-(3,5-다이메틸-1H-피라졸-1-일)페닐, 3,5-다이메틸-1-페닐-1H-피라졸, 4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진, 3,4-다이하이드로-2H-1,5-벤조다이옥세핀, 2,2-다이메틸크로만, 4-메틸-2-페닐-1,3-티아졸, 5-피리딘-2-일-2-티에닐, 4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진, 3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진, 5,6-다이클로로-3-피리딘, 2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린 또는 4-아세틸-3,4-다이하이드로-2H-1,4-벤즈옥사진이고;
R6은 2-벤조퓨란, 2-티에닐, 5-클로로-2-티에닐, 4,5-다이클로로-2-티에닐, 4-클로로-3-메틸페닐 또는 4-클로로-3-트라이플루오로메틸페닐이며;
R15는 C-R16이고;
R17은 N 또는 C-R18이며;
R7은 H, 메틸 또는 염소이고;
R8은 H, 또는 염소이며;
R16은 H이고;
R18은 H이며;
단,
a). R6은 R5와 동일하지 않고;
b). R5가 치환된 헤테로사이클인 경우, 이 아니며;
c). R6이 2-티에닐인 경우, R7, R8, R16 및 R18은 동시에 모두 수소는 아니고;
d). 상기 화합물은 이하의 구조들이 아니다:
. - 제1항에 있어서,
N-{4,5-다이클로로-2-[(페닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]피리딘-3-설폰아마이드;
N-(2-{[(4-아미노페닐)설포닐]아미노}-5-클로로페닐)-4-클로로-3-(트라이플루오로메틸)벤젠설폰아마이드;
5-클로로-N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
4-클로로-N-{4-클로로-5-메틸-2-[(페닐설포닐)아미노]페닐}-3-(트라이플루오로메틸)벤젠설폰아마이드;
4-클로로-N-{5-클로로-2-[(페닐설포닐)아미노]페닐}-3-(트라이플루오로메틸)벤젠설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1,3-옥사졸-5-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-(메틸아미노)벤조에이트;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-(메틸아미노)벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2,3-다이옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-2-설폰아마이드;
N-{2-[(바이페닐-4-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸페녹시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-아이소옥사졸-3-일티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸-1-벤조티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드;
4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시벤조산;
N-(4,5-다이클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-tert-뷰틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1H-1,2,4-트라이아졸-5-설폰아마이드;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
3-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}프로판산;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-에톡시벤조산;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸페닐}아세트아마이드;
N-[2-({[3,5-비스(트라이플루오로메틸)페닐]설포닐}아미노)-4,5-다이클로로페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[2-({[4-(벤질옥시)페닐]설포닐}아미노)-4,5-다이클로로페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
2-클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-플루오로벤조산;
메틸 5-클로로-3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-플루오로벤조산;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2,3-다이하이드로-1H-인덴-5-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(1-나프틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-[4,5-다이클로로-2-({[2-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-2-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,4-다이메틸-1,3-티아졸-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸-1,3-티아졸-2-일}아세트아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아이소퀴놀린-5-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-(4,5-다이클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-(페닐설포닐)-1H-피롤-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메톡시-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-5-설폰아마이드;
1-아세틸-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}인돌린-5-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-2-페닐-1,3-티아졸-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-1,2,3,4-테트라하이드로퀴놀린-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2H-크로멘-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-페닐피리딘-3-설폰아마이드;
에틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]아이소니코티네이트;
N-[4,5-다이클로로-2-({[2-클로로-4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-페녹시피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-페닐티오펜-2-설폰아마이드;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸벤조산;
N-(4,5-다이클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-클로로-4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸-1-벤조티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,5-다이메틸퓨란-3-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(피롤리딘-1-일설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸-3-퓨로에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
2,4-다이클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[4-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시페닐}아세트아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(1-메틸-1H-피라졸-5-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸퓨란-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(페녹시메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-페녹시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5,6-다이클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-에톡시-5-{[(메틸아미노)카보닐]아미노}페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-몰폴린-4-일피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[({3-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}크로만-6-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸티오펜-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-하이드록시벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시티오펜-3-카복실레이트;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-퓨로에이트;
N-(4,5-다이클로로-2-{[(2-클로로-4-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-피리딘-2-일티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4'-플루오로바이페닐-4-일)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로-4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤조티아졸-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-3-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
에틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-3-퓨로에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,4-다이하이드로-2H-1,5-벤조다이옥세핀-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1,3-티아졸-2-일}아세트아마이드;
N-{4,5-다이클로로-2-[({4-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-피리미딘-2-일페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진-7-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-나프틸)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-[(바이페닐-3-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
4-클로로-3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조산;
N-[4,5-다이클로로-2-({[4-(피리딘-2-일옥시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-나프틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[6-(다이메틸아미노)-2-나프틸]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(4'-클로로바이페닐-4-일)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린-6-설폰아마이드;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤질}아세트아마이드;
N-[4,5-다이클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸퀴놀린-8-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-메톡시피리딘-3-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-(4,5-다이클로로-2-{[(2,5-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-아이소옥사졸-5-일티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-(1,3-옥사졸-5-일)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[5-(다이메틸아미노)-1-나프틸]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 2-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조에이트;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-피리미딘-2-일페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(메틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-4-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
2-클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[4-(피리딘-3-일옥시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(에틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-플루오로벤조산;
N-{2-[(바이페닐-2-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-{3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸페닐}아세트아마이드;
N-(2-{[(5-tert-뷰틸-2-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{2-[(벤질설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(아이소뷰틸설포닐)아미노]페닐}티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,2-다이메틸크로만-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀-7-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-사이클로헥실페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
4-클로로-N~1~-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}벤젠-1,3-다이설폰아마이드;
N-(4,5-다이클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-4-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-클로로페녹시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
2-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페녹시}아세트아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸-1-페닐-1H-피라졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
4-아세틸-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(메틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{2-[(벤질설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-나프틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-8-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-4-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(1-나프틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(4-tert-뷰틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[2-({[4-(벤질옥시)페닐]설포닐}아미노)-5-클로로페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,4-다이메틸-1,3-티아졸-5-설폰아마이드;
N-[5-클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조티엔-3-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-[5-클로로-2-({[3-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-{5-클로로-2-[(에틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-3-메틸-1-벤조티엔-2-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(아이소뷰틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로-4-플루오로벤조산;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸-1,3-티아졸-2-일}아세트아마이드;
N-(5-클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1H-1,2,4-트라이아졸-5-설폰아마이드;
3-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페닐}프로판산;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-5-클로로티오펜-2-카복실레이트;
N-{2-[(1-벤조퓨란-5-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소인돌린-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-(2-메틸페녹시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로-1,3-벤조티아졸-6-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-에톡시벤조산;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-플루오로벤조산;
N-(5-클로로-2-{[(2,6-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아이소퀴놀린-5-설폰아마이드;
N-(5-클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-아이소옥사졸-3-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조산;
N-(5-클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조산;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로퀴놀린-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로퀴놀린-8-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-6-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시벤조산;
N-(5-클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[2-({[3,5-비스(트라이플루오로메틸)페닐]설포닐}아미노)-5-클로로페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드
N-(5-클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-(페닐설포닐)-1H-피롤-3-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1H-피라졸-4-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1H-인덴-5-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
메틸 4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조에이트;
N-(5-클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메톡시-3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-1,2,3,4-테트라하이드로퀴놀린-6-설폰아마이드;
N-(5-클로로-2-{[(5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-에톡시-5-{[(메틸아미노)카보닐]아미노}페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(4-아세틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조에이트;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3-다이하이드로-1,3-벤조티아졸-6-설폰아마이드;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-1,3-티아졸-2-일}아세트아마이드;
N-(5-클로로-2-{[(3-클로로-4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2H-크로멘-6-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-몰폴린-4-일피리딘-3-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시티오펜-3-카복실레이트;
N-{5-클로로-2-[(3-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[({4-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-페닐피리딘-3-설폰아마이드;
N-[5-클로로-2-({[4-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-{5-클로로-2-[({3-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-퓨로에이트;
N-[5-클로로-2-({[3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-피리미딘-2-일페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
1-아세틸-N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}인돌린-5-설폰아마이드;
에틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]아이소니코티네이트;
N-(5-클로로-2-{[(5-메틸-1-벤조티엔-2-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(1-메틸-1H-피라졸-5-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}크로만-6-설폰아마이드;
N-(5-클로로-2-{[(2-클로로-4-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
에틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-3-퓨로에이트;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조에이트;
N-(5-클로로-2-{[(4-피리미딘-2-일페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-클로로-4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메틸-3-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-[5-클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1-페닐-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,4-다이하이드로-2H-1,5-벤조다이옥세핀-7-설폰아마이드;
N-[5-클로로-2-({[3-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-5-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(피롤리딘-1-일설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-7-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,2-다이메틸크로만-6-설폰아마이드;
N-[5-클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-2-페닐-1,3-티아졸-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-페녹시피리딘-3-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸-3-퓨로에이트;
N-[5-클로로-2-({[4-(페녹시메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-하이드록시벤조산;
N-(5-클로로-2-{[(5-피리딘-2-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진-7-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-4-설폰아마이드;
N-(5-클로로-2-{[(5-페닐-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-(5-클로로-2-{[(4-페녹시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조티엔-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4'-플루오로바이페닐-4-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
2-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페녹시}아세트아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조산;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸벤조산;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2,4-다이클로로벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5,6-다이클로로피리딘-3-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이클로로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-플루오로-4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로-4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-사이아노-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-나프틸)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-3-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로피리딘-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}피리딘-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-(5-클로로-2-{[(5-아이소옥사졸-5-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이클로로-4-하이드록시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-플루오로벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4'-클로로바이페닐-4-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[5-(1,3-옥사졸-5-일)-2-티에닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀-7-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-클로로벤조산;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로피리딘-3-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로벤조산;
N-{3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸페닐}아세트아마이드;
N-(5-클로로-2-{[(4-사이클로헥실페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-메톡시피리딘-3-설폰아마이드;
4-아세틸-N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-[5-클로로-2-({[5-(다이메틸아미노)-1-나프틸]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로페닐}아세트아마이드;
N-[5-클로로-2-({[4-(피리딘-3-일옥시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(5-tert-뷰틸-2-메틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N~1~-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-클로로벤젠-1,3-다이설폰아마이드;
N-[5-클로로-2-({[4-(2-클로로페녹시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(피리딘-2-일옥시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤질}아세트아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조에이트;
메틸 2-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조에이트;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3-메틸퀴놀린-8-설폰아마이드;
N-[5-클로로-2-({[6-(다이메틸아미노)-2-나프틸]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드; 및
N-[5-클로로-3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드로부터 선택되는 것인 화합물. - 제1항 또는 제2항에 따른 화합물을 포함하는 눈염증 질환 또는 피부염증 질환의 치료에 사용하기 위한 약제학적 조성물.
- 제3항에 있어서, 상기 화합물은
N-{4,5-다이클로로-2-[(페닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]티오펜-2-설폰아마이드;
N-[2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]피리딘-3-설폰아마이드;
N-(2-{[(4-아미노페닐)설포닐]아미노}-5-클로로페닐)-4-클로로-3-(트라이플루오로메틸)벤젠설폰아마이드;
5-클로로-N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)-4-메틸페닐]-1-메틸-1H-이미다졸-4-설폰아마이드;
4-클로로-N-{4-클로로-5-메틸-2-[(페닐설포닐)아미노]페닐}-3-(트라이플루오로메틸)벤젠설폰아마이드;
4-클로로-N-{5-클로로-2-[(페닐설포닐)아미노]페닐}-3-(트라이플루오로메틸)벤젠설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1,3-옥사졸-5-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-(메틸아미노)벤조에이트;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-(메틸아미노)벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2,3-다이옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-2-옥소인돌린-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-2-설폰아마이드;
N-{2-[(바이페닐-4-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-메틸페녹시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-아이소옥사졸-3-일티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸-1-벤조티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드;
4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시벤조산;
N-(4,5-다이클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-tert-뷰틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1H-1,2,4-트라이아졸-5-설폰아마이드;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
3-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}프로판산;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-에톡시벤조산;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸페닐}아세트아마이드;
N-[2-({[3,5-비스(트라이플루오로메틸)페닐]설포닐}아미노)-4,5-다이클로로페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[2-({[4-(벤질옥시)페닐]설포닐}아미노)-4,5-다이클로로페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
2-클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-플루오로벤조산;
메틸 5-클로로-3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-플루오로벤조산;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2,3-다이하이드로-1H-인덴-5-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(1-나프틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-[4,5-다이클로로-2-({[2-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-2-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,4-다이메틸-1,3-티아졸-5-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸-1,3-티아졸-2-일}아세트아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아이소퀴놀린-5-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-8-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,5-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,4-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-(4,5-다이클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퀴놀린-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-(페닐설포닐)-1H-피롤-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메톡시-3-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-5-설폰아마이드;
1-아세틸-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}인돌린-5-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-2-페닐-1,3-티아졸-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-1,2,3,4-테트라하이드로퀴놀린-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2H-크로멘-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-페닐피리딘-3-설폰아마이드;
에틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]아이소니코티네이트;
N-[4,5-다이클로로-2-({[2-클로로-4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-5-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-페녹시피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-페닐티오펜-2-설폰아마이드;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸벤조산;
N-(4,5-다이클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-클로로-4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2,4-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸-1-벤조티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,5-다이메틸퓨란-3-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(피롤리딘-1-일설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸-3-퓨로에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
2,4-다이클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[4-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메톡시페닐}아세트아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(1-메틸-1H-피라졸-5-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸퓨란-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(페녹시메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-페녹시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5,6-다이클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-4-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-에톡시-5-{[(메틸아미노)카보닐]아미노}페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-몰폴린-4-일피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[({3-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}크로만-6-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-메틸티오펜-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-하이드록시벤조산;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조에이트;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시티오펜-3-카복실레이트;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-퓨로에이트;
N-(4,5-다이클로로-2-{[(2-클로로-4-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-피리딘-2-일티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4'-플루오로바이페닐-4-일)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-플루오로-4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3-다이하이드로-1,3-벤조티아졸-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}퓨란-3-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
에틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-3-퓨로에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,4-다이하이드로-2H-1,5-벤조다이옥세핀-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1-벤조퓨란-7-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-사이아노-4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-1,3-티아졸-2-일}아세트아마이드;
N-{4,5-다이클로로-2-[({4-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-피리미딘-2-일페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조티오펜-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진-7-설폰아마이드;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-나프틸)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{2-[(바이페닐-3-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
4-클로로-3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조산;
N-[4,5-다이클로로-2-({[4-(피리딘-2-일옥시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-나프틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[6-(다이메틸아미노)-2-나프틸]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-(4,5-다이클로로-2-{[(4'-클로로바이페닐-4-일)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린-6-설폰아마이드;
N-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤질}아세트아마이드;
N-[4,5-다이클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3-메틸퀴놀린-8-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-[4,5-다이클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
6-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-6-메톡시피리딘-3-설폰아마이드;
메틸 5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-(4,5-다이클로로-2-{[(2,5-다이메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(2-{[(4-아세틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
메틸 3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-아이소옥사졸-5-일티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-5-(1,3-옥사졸-5-일)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(5-클로로-2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[5-(다이메틸아미노)-1-나프틸]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
메틸 2-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메톡시벤조에이트;
5-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-피리미딘-2-일페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(메틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3,5-다이클로로-4-하이드록시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
2-클로로-5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]벤조산;
N-[4,5-다이클로로-2-({[4-(피리딘-3-일옥시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(에틸설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
5-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-2-플루오로벤조산;
N-{2-[(바이페닐-2-일설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드;
N-{3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]-4-메틸페닐}아세트아마이드;
N-(2-{[(5-tert-뷰틸-2-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-{2-[(벤질설포닐)아미노]-4,5-다이클로로페닐}티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(아이소뷰틸설포닐)아미노]페닐}티오펜-2-설폰아마이드
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2,2-다이메틸크로만-6-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀-7-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-사이클로헥실페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
4-클로로-N~1~-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}벤젠-1,3-다이설폰아마이드;
N-(4,5-다이클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{3-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페닐}아세트아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-메틸-1H-인돌-4-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-4,5-다이클로로페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(3-클로로-4-사이아노페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}티오펜-2-설폰아마이드;
N-[4,5-다이클로로-2-({[4-(2-클로로페녹시)페닐]설포닐}아미노)페닐]티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(4-메톡시페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-(4,5-다이클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
2-{4-[({4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}아미노)설포닐]페녹시}아세트아마이드;
N-(4,5-다이클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,5-다이메틸-1-페닐-1H-피라졸-4-설폰아마이드;
N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
2-클로로-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}피리딘-3-설폰아마이드;
4-아세틸-N-{4,5-다이클로로-2-[(2-티에닐설포닐)아미노]페닐}-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-(4,5-다이클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)티오펜-2-설폰아마이드;
N-{5-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{4-클로로-2-[(2-티에닐설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(메틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-이미다졸-4-설폰아마이드;
N-{2-[(벤질설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-나프틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-8-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-4-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(1-나프틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(4-tert-뷰틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,4-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[2-({[4-(벤질옥시)페닐]설포닐}아미노)-5-클로로페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조다이옥솔-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,4-다이메틸-1,3-티아졸-5-설폰아마이드;
N-[5-클로로-2-({[3-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조티엔-3-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3-벤조티아졸-6-설폰아마이드;
N-[5-클로로-2-({[3-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-(트라이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]티오펜-2-카복실레이트;
N-{5-클로로-2-[(에틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸아이소옥사졸-4-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-3-메틸-1-벤조티엔-2-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-클로로-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(아이소뷰틸설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로-4-플루오로벤조산;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸-1,3-티아졸-2-일}아세트아마이드;
N-(5-클로로-2-{[(2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2,5-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1H-1,2,4-트라이아졸-5-설폰아마이드;
3-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페닐}프로판산;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-5-클로로티오펜-2-카복실레이트;
N-{2-[(1-벤조퓨란-5-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소인돌린-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1H-피라졸-4-설폰아마이드;
N-[5-클로로-2-({[4-(2-메틸페녹시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3-다이하이드로-1,3-벤즈옥사졸-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로-1,3-벤조티아졸-6-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-에톡시벤조산;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-플루오로벤조산;
N-(5-클로로-2-{[(2,6-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아이소퀴놀린-5-설폰아마이드;
N-(5-클로로-2-{[(2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-아이소옥사졸-3-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조산;
N-(5-클로로-2-{[(3,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조산;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로퀴놀린-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로퀴놀린-8-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}퀴놀린-6-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시벤조산;
N-(5-클로로-2-{[(2,4-다이메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[2-({[3,5-비스(트라이플루오로메틸)페닐]설포닐}아미노)-5-클로로페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드
N-(5-클로로-2-{[(2,3-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-(페닐설포닐)-1H-피롤-3-설폰아마이드;
N-(5-클로로-2-{[(2,6-다이클로로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-(메틸설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이클로로-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1H-피라졸-4-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1H-인덴-5-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
메틸 4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조에이트;
N-(5-클로로-2-{[(2,4,5-트라이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-메톡시-3-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-1,2,3,4-테트라하이드로퀴놀린-6-설폰아마이드;
N-(5-클로로-2-{[(5-{[(다이메틸아미노)카보닐]아미노}-2-에톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-에톡시-5-{[(메틸아미노)카보닐]아미노}페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(4-아세틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤조에이트;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3-다이하이드로-1,3-벤조티아졸-6-설폰아마이드;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-1,3-티아졸-2-일}아세트아마이드;
N-(5-클로로-2-{[(3-클로로-4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2H-크로멘-6-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2,4-다이플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메톡시페닐}아세트아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-몰폴린-4-일피리딘-3-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시티오펜-3-카복실레이트;
N-{5-클로로-2-[(3-퓨릴설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[({4-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-페닐피리딘-3-설폰아마이드;
N-[5-클로로-2-({[4-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로이미다조[2,1-b][1,3]티아졸-5-설폰아마이드;
N-{5-클로로-2-[({3-[(6-메틸피라진-2-일)옥시]페닐}설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-퓨로에이트;
N-[5-클로로-2-({[3-(5-메틸-1,2,4-옥사아디아졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-피리미딘-2-일페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
1-아세틸-N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}인돌린-5-설폰아마이드;
에틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]아이소니코티네이트;
N-(5-클로로-2-{[(5-메틸-1-벤조티엔-2-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(1-메틸-1H-피라졸-5-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}크로만-6-설폰아마이드;
N-(5-클로로-2-{[(2-클로로-4-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
에틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-3-퓨로에이트;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조에이트;
N-(5-클로로-2-{[(4-피리미딘-2-일페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(5-메틸-1,3,4-옥사아디아졸-2-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[2-클로로-4-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메틸-3-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-1-메틸-1H-피롤-2-카복실레이트;
N-[5-클로로-2-({[4-(3,5-다이메틸-1H-피라졸-1-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2-플루오로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-피라졸-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,5-다이메틸-1-페닐-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,4-다이하이드로-2H-1,5-벤조다이옥세핀-7-설폰아마이드;
N-[5-클로로-2-({[3-(1-메틸-1H-피라졸-3-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-5-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(피롤리딘-1-일설포닐)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-퓨릴)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-메틸-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-7-설폰아마이드;
N-{5-클로로-2-[(2,3-다이하이드로-1-벤조퓨란-7-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,2-다이메틸크로만-6-설폰아마이드;
N-[5-클로로-2-({[4-(2-메틸-1,3-티아졸-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-2-페닐-1,3-티아졸-5-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-페녹시피리딘-3-설폰아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸-3-퓨로에이트;
N-[5-클로로-2-({[4-(페녹시메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-하이드록시벤조산;
N-(5-클로로-2-{[(5-피리딘-2-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-메틸-1,3-벤조티아졸-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-메틸-3,4-다이하이드로-2H-피리도[3,2-b][1,4]옥사진-7-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1-메틸-1H-인돌-4-설폰아마이드;
N-(5-클로로-2-{[(5-페닐-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3-옥소-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-(5-클로로-2-{[(4-페녹시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조티엔-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4'-플루오로바이페닐-4-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,3,5-트라이메틸-1H-피라졸-4-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5-클로로-1,3-다이메틸-1H-피라졸-4-설폰아마이드;
2-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]페녹시}아세트아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조산;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸벤조산;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2,4-다이클로로벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-5,6-다이클로로피리딘-3-설폰아마이드;
N-(5-클로로-2-{[(2,4-다이클로로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-플루오로-4-메톡시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(1H-피라졸-1-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2,5-다이메틸-3-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(다이플루오로메톡시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로-4-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-플루오로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-2-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3-사이아노-4-플루오로페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-나프틸)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-3-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-클로로피리딘-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}피리딘-3-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,3-다이하이드로-1,4-벤조다이옥신-6-설폰아마이드;
N-(5-클로로-2-{[(5-아이소옥사졸-5-일-2-티에닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(3,5-다이클로로-4-하이드록시페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-플루오로벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-1,2-다이메틸-1H-이미다졸-4-설폰아마이드;
N-(2-{[(4-브로모-3-메틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(2-플루오로-5-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-(5-클로로-2-{[(4'-클로로바이페닐-4-일)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[3-(2-메틸피리미딘-4-일)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[5-(1,3-옥사졸-5-일)-2-티에닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{2-[(바이페닐-2-일설포닐)아미노]-5-클로로페닐}-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2-옥소-2,3,4,5-테트라하이드로-1H-1-벤즈아제핀-7-설폰아마이드;
N-(5-클로로-2-{[(3-클로로-4-사이아노페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-클로로벤조산;
N-(2-{[(3-아세틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-클로로피리딘-3-설폰아마이드;
N-(5-클로로-2-{[(5-클로로-2-메틸페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로벤조산;
N-{3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메틸페닐}아세트아마이드;
N-(5-클로로-2-{[(4-사이클로헥실페닐)설포닐]아미노}페닐)-1-벤조퓨란-2-설폰아마이드;
N-{5-클로로-2-[(5,6,7,8-테트라하이드로나프탈렌-2-일설포닐)아미노]페닐}-1-벤조퓨란-2-설폰아마이드;
3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조산;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-2,3-다이옥소-1,2,3,4-테트라하이드로퀴녹살린-6-설폰아마이드;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-6-메톡시피리딘-3-설폰아마이드;
4-아세틸-N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3,4-다이하이드로-2H-1,4-벤즈옥사진-6-설폰아마이드;
N-[5-클로로-2-({[5-(다이메틸아미노)-1-나프틸]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-클로로페닐}아세트아마이드;
N-[5-클로로-2-({[4-(피리딘-3-일옥시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-(2-{[(5-tert-뷰틸-2-메틸페닐)설포닐]아미노}-5-클로로페닐)-1-벤조퓨란-2-설폰아마이드;
N~1~-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-4-클로로벤젠-1,3-다이설폰아마이드;
N-[5-클로로-2-({[4-(2-클로로페녹시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[5-클로로-2-({[4-(피리딘-2-일옥시)페닐]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-{4-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]벤질}아세트아마이드;
메틸 5-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조에이트;
메틸 2-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-4-메톡시벤조에이트;
메틸 3-[({2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}아미노)설포닐]-2-메틸벤조에이트;
N-{2-[(1-벤조퓨란-2-일설포닐)아미노]-4-클로로페닐}-3-메틸퀴놀린-8-설폰아마이드;
N-[5-클로로-2-({[6-(다이메틸아미노)-2-나프틸]설포닐}아미노)페닐]-1-벤조퓨란-2-설폰아마이드;
N-[3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드; 및
N-[5-클로로-3-({[4-클로로-3-(트라이플루오로메틸)페닐]설포닐}아미노)피리딘-2-일]티오펜-2-설폰아마이드로부터 선택된 것인 약제학적 조성물.
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US20120157444A1 (en) | 2012-06-21 |
CN103384662A (zh) | 2013-11-06 |
WO2012082633A1 (en) | 2012-06-21 |
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US20160228407A1 (en) | 2016-08-11 |
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AU2011344125A1 (en) | 2013-07-25 |
JP2013545807A (ja) | 2013-12-26 |
US9603834B2 (en) | 2017-03-28 |
HK1218910A1 (zh) | 2017-03-17 |
RU2654213C9 (ru) | 2018-06-25 |
CA2822044C (en) | 2021-12-21 |
EP2955173B1 (en) | 2017-10-04 |
RU2654213C2 (ru) | 2018-05-17 |
EP2955173A1 (en) | 2015-12-16 |
BR112013015223A2 (pt) | 2016-09-13 |
JP6030568B2 (ja) | 2016-11-24 |
HK1259248A1 (zh) | 2019-11-29 |
EP2651901B1 (en) | 2015-05-27 |
CN108383828A (zh) | 2018-08-10 |
BR112013015223B1 (pt) | 2021-12-14 |
KR20130132541A (ko) | 2013-12-04 |
US20140221351A1 (en) | 2014-08-07 |
CA2822044A1 (en) | 2012-06-21 |
US8729066B2 (en) | 2014-05-20 |
AU2011344125B2 (en) | 2017-04-20 |
US8580779B2 (en) | 2013-11-12 |
ES2655090T3 (es) | 2018-02-16 |
HK1189890A1 (en) | 2014-06-20 |
EP2651901A1 (en) | 2013-10-23 |
RU2013132649A (ru) | 2015-01-27 |
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