NO315607B1 - Tienyl-, furyl-, pyrrolyl- og bifenylsulfonamider, farmasöytiske preparaterog fremstilte gjenstander omfattende slike forbindelser, oganvendelser av slike forbindelser - Google Patents

Info

Publication number

NO315607B1

NO315607B1 NO19974577A NO974577A NO315607B1 NO 315607 B1 NO315607 B1 NO 315607B1 NO 19974577 A NO19974577 A NO 19974577A NO 974577 A NO974577 A NO 974577A NO 315607 B1 NO315607 B1 NO 315607B1

Authority

NO

Norway

Prior art keywords

isoxazolyl

methyl

thiophene

sulfonamide

chloro

Prior art date

1995-04-04

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• 150000001875 compounds Chemical class 0.000 title claims description 249
• 125000001544 thienyl group Chemical group 0.000 title claims description 29
• 125000002541 furyl group Chemical group 0.000 title claims description 22
• 125000000168 pyrrolyl group Chemical group 0.000 title claims description 22
• 239000000825 pharmaceutical preparation Substances 0.000 title claims description 15
• SBXDENYROQKXBE-UHFFFAOYSA-N 2-phenylbenzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1C1=CC=CC=C1 SBXDENYROQKXBE-UHFFFAOYSA-N 0.000 title description 4
• 108050009340 Endothelin Proteins 0.000 claims abstract description 153
• 102000002045 Endothelin Human genes 0.000 claims abstract description 132
• ZUBDGKVDJUIMQQ-UBFCDGJISA-N endothelin-1 Chemical compound C([C@@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(O)=O)NC(=O)[C@H]1NC(=O)[C@H](CC=2C=CC=CC=2)NC(=O)[C@@H](CC=2C=CC(O)=CC=2)NC(=O)[C@H](C(C)C)NC(=O)[C@H]2CSSC[C@@H](C(N[C@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CCSC)C(=O)N[C@H](CC(O)=O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCC(O)=O)C(=O)N2)=O)NC(=O)[C@@H](CO)NC(=O)[C@H](N)CSSC1)C1=CNC=N1 ZUBDGKVDJUIMQQ-UBFCDGJISA-N 0.000 claims abstract description 120
• 230000000694 effects Effects 0.000 claims abstract description 64
• 229940124530 sulfonamide Drugs 0.000 claims abstract description 62
• 102000005962 receptors Human genes 0.000 claims abstract description 57
• 108020003175 receptors Proteins 0.000 claims abstract description 57
• 150000003456 sulfonamides Chemical class 0.000 claims abstract description 49
• 230000027455 binding Effects 0.000 claims abstract description 36
• 150000003839 salts Chemical class 0.000 claims abstract description 36
• 102000010180 Endothelin receptor Human genes 0.000 claims abstract description 24
• 108050001739 Endothelin receptor Proteins 0.000 claims abstract description 24
• BWJZHYWAXLWLTB-UHFFFAOYSA-N thiophene-3-sulfonamide Chemical compound NS(=O)(=O)C=1C=CSC=1 BWJZHYWAXLWLTB-UHFFFAOYSA-N 0.000 claims description 124
• -1 phenoxy, naphthyl Chemical group 0.000 claims description 116
• 239000000203 mixture Substances 0.000 claims description 96
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 64
• 125000001424 substituent group Chemical group 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 61
• 229910052739 hydrogen Inorganic materials 0.000 claims description 61
• 229910052736 halogen Inorganic materials 0.000 claims description 39
• 150000002367 halogens Chemical class 0.000 claims description 39
• 230000001404 mediated effect Effects 0.000 claims description 39
• 150000002431 hydrogen Chemical class 0.000 claims description 36
• 125000000217 alkyl group Chemical group 0.000 claims description 33
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 29
• 201000010099 disease Diseases 0.000 claims description 29
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
• 238000011282 treatment Methods 0.000 claims description 24
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
• 208000024891 symptom Diseases 0.000 claims description 20
• 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 14
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 13
• 239000005022 packaging material Substances 0.000 claims description 13
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
• 239000003814 drug Substances 0.000 claims description 12
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 229910052801 chlorine Inorganic materials 0.000 claims description 11
• 239000003937 drug carrier Substances 0.000 claims description 11
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 11
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 10
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
• 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 8
• 125000004432 carbon atom Chemical group C* 0.000 claims description 8
• 238000009472 formulation Methods 0.000 claims description 8
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
• 125000005842 heteroatom Chemical group 0.000 claims description 7
• 125000004076 pyridyl group Chemical group 0.000 claims description 7
• 125000001113 thiadiazolyl group Chemical group 0.000 claims description 7
• 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 6
• 125000001624 naphthyl group Chemical group 0.000 claims description 6
• 229910052760 oxygen Inorganic materials 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• LONCVVCONRXSBM-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-(4-methylphenyl)thiophene-2-carboxamide Chemical group CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C=CC(C)=CC=2)=C1Cl LONCVVCONRXSBM-UHFFFAOYSA-N 0.000 claims description 5
• OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 claims description 5
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 5
• 125000003545 alkoxy group Chemical group 0.000 claims description 4
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 4
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
• 125000001475 halogen functional group Chemical group 0.000 claims description 4
• LYXCSZFDWCMVQS-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-[(3,4-dimethoxyphenyl)methyl]-1-benzothiophene-3-sulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1CC1=C(S(=O)(=O)NC2=C(C(C)=NO2)Br)C2=CC=CC=C2S1 LYXCSZFDWCMVQS-UHFFFAOYSA-N 0.000 claims description 4
• IPZBJXVEBUKSJF-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-[(4-ethylphenyl)methyl]-1-benzothiophene-3-sulfonamide Chemical compound C1=CC(CC)=CC=C1CC1=C(S(=O)(=O)NC2=C(C(C)=NO2)Br)C2=CC=CC=C2S1 IPZBJXVEBUKSJF-UHFFFAOYSA-N 0.000 claims description 4
• UYVGNOOFQBHJQC-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-[(4-methoxyphenyl)methyl]-1-benzothiophene-3-sulfonamide Chemical compound C1=CC(OC)=CC=C1CC1=C(S(=O)(=O)NC2=C(C(C)=NO2)Br)C2=CC=CC=C2S1 UYVGNOOFQBHJQC-UHFFFAOYSA-N 0.000 claims description 4
• SOVAQDYTHJXDHM-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-butyl-1-benzothiophene-3-sulfonamide Chemical compound CCCCC=1SC2=CC=CC=C2C=1S(=O)(=O)NC=1ON=C(C)C=1Br SOVAQDYTHJXDHM-UHFFFAOYSA-N 0.000 claims description 4
• GMEWGELDOLVRLF-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-propan-2-yl-1-benzothiophene-3-sulfonamide Chemical compound CC(C)C=1SC2=CC=CC=C2C=1S(=O)(=O)NC=1ON=C(C)C=1Br GMEWGELDOLVRLF-UHFFFAOYSA-N 0.000 claims description 4
• YHAPZJJWLZFXDR-UHFFFAOYSA-N n-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[[4-(dimethylamino)phenyl]methyl]-1-benzothiophene-3-sulfonamide Chemical compound C1=CC(N(C)C)=CC=C1CC1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C2=CC=CC=C2S1 YHAPZJJWLZFXDR-UHFFFAOYSA-N 0.000 claims description 4
• 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 3
• JQBUPYPWHBIMNX-UHFFFAOYSA-N 1,3-benzodioxol-5-yl 3-[(4-bromo-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carboxylate Chemical group CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)OC=2C=C3OCOC3=CC=2)=C1Br JQBUPYPWHBIMNX-UHFFFAOYSA-N 0.000 claims description 3
• LFJWGKAUSUIRQH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-1-benzothiophene-3-sulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C3=CC=CC=C3SC=2CC=2C=C3OCOC3=CC=2)=C1Br LFJWGKAUSUIRQH-UHFFFAOYSA-N 0.000 claims description 3
• HQLOXYYRUBWVRA-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-n-(4-chloro-3-methyl-1,2-oxazol-5-yl)-1-benzothiophene-3-sulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C3=CC=CC=C3SC=2CC=2C=C3OCOC3=CC=2)=C1Cl HQLOXYYRUBWVRA-UHFFFAOYSA-N 0.000 claims description 3
• BJHMFFQWKWFBJL-UHFFFAOYSA-N 2-[(4-chlorophenyl)methyl]-n-(3,4-dimethyl-1,2-oxazol-5-yl)-1-benzothiophene-3-sulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C3=CC=CC=C3SC=2CC=2C=CC(Cl)=CC=2)=C1C BJHMFFQWKWFBJL-UHFFFAOYSA-N 0.000 claims description 3
• JXTUMHYPNSZHJD-UHFFFAOYSA-N BrC=1C(=NOC=1NS(=O)(=O)C1=CC(=C(C=C1)C1=CC=C(C=C1)C)C1=CC=CC=C1)C Chemical group BrC=1C(=NOC=1NS(=O)(=O)C1=CC(=C(C=C1)C1=CC=C(C=C1)C)C1=CC=CC=C1)C JXTUMHYPNSZHJD-UHFFFAOYSA-N 0.000 claims description 3
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
• 125000001041 indolyl group Chemical group 0.000 claims description 3
• NLOJCHDRSIJGOX-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-ethyl-5-methyl-1-benzothiophene-3-sulfonamide Chemical compound CCC=1SC2=CC=C(C)C=C2C=1S(=O)(=O)NC=1ON=C(C)C=1Br NLOJCHDRSIJGOX-UHFFFAOYSA-N 0.000 claims description 3
• PKOUZADLIGOYGU-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-propyl-1-benzothiophene-3-sulfonamide Chemical compound CCCC=1SC2=CC=CC=C2C=1S(=O)(=O)NC=1ON=C(C)C=1Br PKOUZADLIGOYGU-UHFFFAOYSA-N 0.000 claims description 3
• RGWWCSLENLYGRC-UHFFFAOYSA-N n-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-ethyl-1-benzofuran-3-sulfonamide Chemical compound CCC=1OC2=CC=CC=C2C=1S(=O)(=O)NC=1ON=C(C)C=1Cl RGWWCSLENLYGRC-UHFFFAOYSA-N 0.000 claims description 3
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
• RPGLFLADGRRVLZ-UHFFFAOYSA-N 1-(furan-2-yl)-2-phenylethanone Chemical compound C=1C=COC=1C(=O)CC1=CC=CC=C1 RPGLFLADGRRVLZ-UHFFFAOYSA-N 0.000 claims description 2
• STFMKWCNBOPACP-UHFFFAOYSA-N 2-phenyl-1-(1h-pyrrol-2-yl)ethanone Chemical compound C=1C=CNC=1C(=O)CC1=CC=CC=C1 STFMKWCNBOPACP-UHFFFAOYSA-N 0.000 claims description 2
• HXMVINSKZVYIDI-UHFFFAOYSA-N 2-phenyl-1-thiophen-2-ylethanone Chemical compound C=1C=CSC=1C(=O)CC1=CC=CC=C1 HXMVINSKZVYIDI-UHFFFAOYSA-N 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• AMZDQGOJRQATPU-UHFFFAOYSA-N n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-2-[(3,4,5-trimethoxyphenyl)methyl]-1-benzothiophene-3-sulfonamide Chemical compound COC1=C(OC)C(OC)=CC(CC2=C(C3=CC=CC=C3S2)S(=O)(=O)NC2=C(C(C)=NO2)Br)=C1 AMZDQGOJRQATPU-UHFFFAOYSA-N 0.000 claims description 2
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• VMRGBLIETYGKNV-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-(2,4,6-trimethylphenyl)thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=CC(C)=CC=2C)C)=C1Cl VMRGBLIETYGKNV-UHFFFAOYSA-N 0.000 claims 2
• 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
• NOKYQBAYRCEAFO-UHFFFAOYSA-N n-(4-chloro-3-methyl-1,2-oxazol-5-yl)-2-[2-(2,4,6-trimethylphenyl)acetyl]thiophene-3-sulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC(C)=CC=2C)C)=C1Cl NOKYQBAYRCEAFO-UHFFFAOYSA-N 0.000 claims 2
• RTKXFSZKGFZASV-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-n-(4-chloro-3-methyl-1,2-oxazol-5-yl)-6-methoxy-1-benzothiophene-3-sulfonamide Chemical compound C=1C=C2OCOC2=CC=1CC=1SC2=CC(OC)=CC=C2C=1S(=O)(=O)NC=1ON=C(C)C=1Cl RTKXFSZKGFZASV-UHFFFAOYSA-N 0.000 claims 1
• NCDLLSUBNRSBTH-UHFFFAOYSA-N 2-(1,3-benzodioxol-5-ylmethyl)-n-(4-chloro-5-methyl-1,2-oxazol-3-yl)-1-benzothiophene-3-sulfonamide Chemical compound ClC1=C(C)ON=C1NS(=O)(=O)C(C1=CC=CC=C1S1)=C1CC1=CC=C(OCO2)C2=C1 NCDLLSUBNRSBTH-UHFFFAOYSA-N 0.000 claims 1
• GQABMKHWSKPQNS-UHFFFAOYSA-N 2-[2-(1,3-benzodioxol-5-yl)acetyl]-n-(4-chloro-3-methyl-1,2-oxazol-5-yl)thiophene-3-sulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C=C3OCOC3=CC=2)=C1Cl GQABMKHWSKPQNS-UHFFFAOYSA-N 0.000 claims 1
• ZDUSCRASOMLKNJ-UHFFFAOYSA-N 2-[2-(6-acetyl-2,3,4-trimethoxyphenyl)acetyl]-n-(4-chloro-3-methyl-1,2-oxazol-5-yl)thiophene-3-sulfonamide Chemical compound COC1=C(OC)C(OC)=CC(C(C)=O)=C1CC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 ZDUSCRASOMLKNJ-UHFFFAOYSA-N 0.000 claims 1
• CRYCIDMYIUCTGO-UHFFFAOYSA-N 2-[2-[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophen-2-yl]-2-oxoethyl]-3,4,5-trimethoxybenzoic acid Chemical compound COC1=C(OC)C(OC)=CC(C(O)=O)=C1CC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 CRYCIDMYIUCTGO-UHFFFAOYSA-N 0.000 claims 1
• QGSDTRZFMSQTGY-UHFFFAOYSA-N 2-[3-[2-[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophen-2-yl]-2-oxoethyl]-2,4,6-trimethylphenyl]acetic acid Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=C(CC(O)=O)C(C)=CC=2C)C)=C1Cl QGSDTRZFMSQTGY-UHFFFAOYSA-N 0.000 claims 1
• NUYSJKGYSZVXDM-UHFFFAOYSA-N 2-[3-[[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carbonyl]amino]-2,4,6-trimethylphenyl]acetic acid Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=C(CC(O)=O)C(C)=CC=2C)C)=C1Cl NUYSJKGYSZVXDM-UHFFFAOYSA-N 0.000 claims 1
• WHPJZFGIOBCWBN-UHFFFAOYSA-N 2-[4-[2-[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophen-2-yl]-2-oxoethyl]-3,5-dimethylphenyl]acetic acid Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=CC(CC(O)=O)=CC=2C)C)=C1Cl WHPJZFGIOBCWBN-UHFFFAOYSA-N 0.000 claims 1
• DMHFTSLCVHGVMN-UHFFFAOYSA-N 2-[4-[[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophene-2-carbonyl]amino]-3,5-dimethylphenyl]acetic acid Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=CC(CC(O)=O)=CC=2C)C)=C1Cl DMHFTSLCVHGVMN-UHFFFAOYSA-N 0.000 claims 1
• DUEIITTVOKNJCM-UHFFFAOYSA-N 3-(2-phenylacetyl)thiophene-2-sulfonamide Chemical group S1C=CC(C(=O)CC=2C=CC=CC=2)=C1S(=O)(=O)N DUEIITTVOKNJCM-UHFFFAOYSA-N 0.000 claims 1
• ZSYOIVJFFZOOAD-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-(2,3,4-trimethoxy-6-methylphenyl)thiophene-2-carboxamide Chemical group COC1=C(OC)C(OC)=CC(C)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 ZSYOIVJFFZOOAD-UHFFFAOYSA-N 0.000 claims 1
• KSYPAJUESNOIRB-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-(2,6-dimethyl-4-methylsulfonylphenyl)thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=CC(=CC=2C)S(C)(=O)=O)C)=C1Cl KSYPAJUESNOIRB-UHFFFAOYSA-N 0.000 claims 1
• OKPZFLUWPURGTK-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-(4-cyano-2,6-dimethylphenyl)thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=CC(=CC=2C)C#N)C)=C1Cl OKPZFLUWPURGTK-UHFFFAOYSA-N 0.000 claims 1
• UXNJXSWMWFYCEM-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[3-(hydroxymethyl)-2,4,6-trimethylphenyl]thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=C(CO)C(C)=CC=2C)C)=C1Cl UXNJXSWMWFYCEM-UHFFFAOYSA-N 0.000 claims 1
• YPOZZADFWSQCLS-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[4-(2-hydroxyethyl)-2,6-dimethylphenyl]thiophene-2-carboxamide Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)NC=2C(=CC(CCO)=CC=2C)C)=C1Cl YPOZZADFWSQCLS-UHFFFAOYSA-N 0.000 claims 1
• NMPPTEVJVBUHMV-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[6-(2-hydroxyethyl)-2,3,4-trimethoxyphenyl]thiophene-2-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(CCO)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 NMPPTEVJVBUHMV-UHFFFAOYSA-N 0.000 claims 1
• LBLNVNWKVVEBTE-UHFFFAOYSA-N 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-n-[6-(cyanomethyl)-2,3,4-trimethoxyphenyl]thiophene-2-carboxamide Chemical compound COC1=C(OC)C(OC)=CC(CC#N)=C1NC(=O)C1=C(S(=O)(=O)NC2=C(C(C)=NO2)Cl)C=CS1 LBLNVNWKVVEBTE-UHFFFAOYSA-N 0.000 claims 1
• UJHRKXOVJCRXFK-UHFFFAOYSA-N 3-[2-[3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]thiophen-2-yl]-2-oxoethyl]-2,4,6-trimethylbenzoic acid Chemical compound CC1=NOC(NS(=O)(=O)C2=C(SC=C2)C(=O)CC=2C(=C(C(O)=O)C(C)=CC=2C)C)=C1Cl UJHRKXOVJCRXFK-UHFFFAOYSA-N 0.000 claims 1
• NOGNMEFFMUXIKX-UHFFFAOYSA-N 3-phenoxythiophene-2-sulfonamide Chemical group S1C=CC(OC=2C=CC=CC=2)=C1S(=O)(=O)N NOGNMEFFMUXIKX-UHFFFAOYSA-N 0.000 claims 1
• HQTVKQZDWNYRJH-UHFFFAOYSA-N 4-(1,3-benzodioxol-5-yl)-n-(4-bromo-3-methyl-1,2-oxazol-5-yl)-3-phenylbenzenesulfonamide Chemical compound CC1=NOC(NS(=O)(=O)C=2C=C(C(C=3C=C4OCOC4=CC=3)=CC=2)C=2C=CC=CC=2)=C1Br HQTVKQZDWNYRJH-UHFFFAOYSA-N 0.000 claims 1
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