JP2018507234A

JP2018507234A - 肝臓線維症、コレステロールの上昇およびインスリン抵抗性を処置する際における使用のためのｓｒｅｂｐ遮断薬

肝臓線維症、コレステロールの上昇およびインスリン抵抗性を処置する際における使用のためのｓｒｅｂｐ遮断薬 Download PDF

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Publication number: JP2018507234A
Authority: JP; Japan
Prior art keywords: thiazol; phenyl; trifluoromethanesulfonamide; chloro; linear
Prior art date: 2015-03-04
Legal status : Withdrawn

Application number

JP2017546185A

Other languages

English (en)

Japanese (ja)

Other versions

JP2018507234A5 (https=

Inventor

ベルナレス，セバスチャン

リンドキスト，ジェフリー

グハ，モウスミー

Original Assignee

メディベイションテクノロジーズエルエルシー

Priority date

2015-03-04

Filing date

2016-03-03

Publication date

2018-03-15

2016-03-03 Application filed by メディベイションテクノロジーズエルエルシー, メディベイションテクノロジーズエルエルシー filed Critical メディベイションテクノロジーズエルエルシー

2018-03-15 Publication of JP2018507234A publication Critical patent/JP2018507234A/ja

2019-04-18 Publication of JP2018507234A5 publication Critical patent/JP2018507234A5/ja

Status Withdrawn legal-status Critical Current

Links

208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 34
208000019425 cirrhosis of liver Diseases 0.000 title claims abstract description 33
206010022489 Insulin Resistance Diseases 0.000 title claims abstract description 32
206010014476 Elevated cholesterol Diseases 0.000 title claims abstract description 21
208000035150 Hypercholesterolemia Diseases 0.000 title claims abstract description 21
102000009822 Sterol Regulatory Element Binding Proteins Human genes 0.000 title description 37
108010020396 Sterol Regulatory Element Binding Proteins Proteins 0.000 title description 37
150000001875 compounds Chemical class 0.000 claims abstract description 382
238000000034 method Methods 0.000 claims abstract description 55
208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims abstract description 47
206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims abstract description 39
-1 n- propyl Chemical group 0.000 claims description 135
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 120
125000000217 alkyl group Chemical group 0.000 claims description 89
229910052739 hydrogen Inorganic materials 0.000 claims description 89
125000005843 halogen group Chemical group 0.000 claims description 87
239000001257 hydrogen Substances 0.000 claims description 87
150000003839 salts Chemical class 0.000 claims description 56
229910052736 halogen Inorganic materials 0.000 claims description 47
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 46
150000002367 halogens Chemical class 0.000 claims description 46
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
150000002431 hydrogen Chemical class 0.000 claims description 39
125000003342 alkenyl group Chemical group 0.000 claims description 38
125000000753 cycloalkyl group Chemical group 0.000 claims description 37
125000003118 aryl group Chemical group 0.000 claims description 34
125000000392 cycloalkenyl group Chemical group 0.000 claims description 31
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 27
125000003545 alkoxy group Chemical group 0.000 claims description 27
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 26
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 26
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 21
125000005842 heteroatom Chemical group 0.000 claims description 21
125000001072 heteroaryl group Chemical group 0.000 claims description 19
150000001408 amides Chemical class 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 17
208000035475 disorder Diseases 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 15
UNOPLLVTUGSYOC-UHFFFAOYSA-N n-[3-chloro-4-[2-[2-(2-methylpropyl)pyridin-4-yl]-1,3-thiazol-4-yl]phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound C1=NC(CC(C)C)=CC(C=2SC=C(N=2)C=2C(=CC(NS(=O)(=O)C(F)(F)F)=CC=2)Cl)=C1 UNOPLLVTUGSYOC-UHFFFAOYSA-N 0.000 claims description 15
ODANWQNFUOCUJK-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(c2)N2CCCCC2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(c2)N2CCCCC2)c(Cl)c1 ODANWQNFUOCUJK-UHFFFAOYSA-N 0.000 claims description 13
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 13
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 claims description 12
NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 12
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 12
YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 12
238000004519 manufacturing process Methods 0.000 claims description 12
239000011734 sodium Substances 0.000 claims description 12
DJIDUBBYFBGOOP-UHFFFAOYSA-N 1,1,1-trifluoro-N-[2-hydroxy-4-[2-(2-propylpyridin-4-yl)-1,3-thiazol-4-yl]phenyl]methanesulfonamide Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(O)c1 DJIDUBBYFBGOOP-UHFFFAOYSA-N 0.000 claims description 11
SWWBFHDVGYKSIC-UHFFFAOYSA-N COc1cc(ccc1NS(=O)(=O)C(F)(F)F)-c1csc(n1)-c1ccnc(c1)C(C)(C)C Chemical compound COc1cc(ccc1NS(=O)(=O)C(F)(F)F)-c1csc(n1)-c1ccnc(c1)C(C)(C)C SWWBFHDVGYKSIC-UHFFFAOYSA-N 0.000 claims description 11
LNLTWJZKKZIRNP-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cccc(c2)N2CCCCC2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cccc(c2)N2CCCCC2)c(Cl)c1 LNLTWJZKKZIRNP-UHFFFAOYSA-N 0.000 claims description 11
SXCHDDWMFBETRA-UHFFFAOYSA-N oxazinan-3-one Chemical compound O=C1CCCON1 SXCHDDWMFBETRA-UHFFFAOYSA-N 0.000 claims description 11
URKKWJVHFWMZKH-UHFFFAOYSA-N FC(F)(F)CCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound FC(F)(F)CCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl URKKWJVHFWMZKH-UHFFFAOYSA-N 0.000 claims description 10
AHUAGCKFDFIMIG-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cccc3[nH]ccc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cccc3[nH]ccc23)c(Cl)c1 AHUAGCKFDFIMIG-UHFFFAOYSA-N 0.000 claims description 10
ZFAHMEQVEFTWSO-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(Cc3ccccc3)c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(Cc3ccccc3)c2)c(Cl)c1 ZFAHMEQVEFTWSO-UHFFFAOYSA-N 0.000 claims description 10
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 10
BVDTTZBONAAQKG-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1cc(cs1)-c1ccc(NS(C)(=O)=O)cc1Cl Chemical compound CC(C)(C)c1cc(ccn1)-c1cc(cs1)-c1ccc(NS(C)(=O)=O)cc1Cl BVDTTZBONAAQKG-UHFFFAOYSA-N 0.000 claims description 9
ZJDMKNJQTRBDAM-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl ZJDMKNJQTRBDAM-UHFFFAOYSA-N 0.000 claims description 9
JSMKSEHKSJYCEL-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl JSMKSEHKSJYCEL-UHFFFAOYSA-N 0.000 claims description 9
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 9
UAKOGGPGLWSGGR-UHFFFAOYSA-N CN1CCN(CC1)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CN1CCN(CC1)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl UAKOGGPGLWSGGR-UHFFFAOYSA-N 0.000 claims description 7
BVWJTQHRWMMOBM-UHFFFAOYSA-N COc1ccc(cc1OC)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound COc1ccc(cc1OC)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl BVWJTQHRWMMOBM-UHFFFAOYSA-N 0.000 claims description 7
LNJVDALLKQEFED-UHFFFAOYSA-N Cc1ccc(cc1)S(=O)(=O)Nc1cccc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Cc1ccc(cc1)S(=O)(=O)Nc1cccc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl LNJVDALLKQEFED-UHFFFAOYSA-N 0.000 claims description 7
ANQHXMUASRENER-UHFFFAOYSA-N Cc1cnccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Cc1cnccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl ANQHXMUASRENER-UHFFFAOYSA-N 0.000 claims description 7
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DXRDAEXRJRCNBM-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccc3cc[nH]c3c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccc3cc[nH]c3c2)c(Cl)c1 DXRDAEXRJRCNBM-UHFFFAOYSA-N 0.000 claims description 7
CZNYTGGHEPIPTD-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cccc3ccccc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cccc3ccccc23)c(Cl)c1 CZNYTGGHEPIPTD-UHFFFAOYSA-N 0.000 claims description 7
NPFZGDGBLYBWGU-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccccc2-c2ccccc2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccccc2-c2ccccc2)c(Cl)c1 NPFZGDGBLYBWGU-UHFFFAOYSA-N 0.000 claims description 7
BBFODUJPSOVNMA-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(CC3CCCCC3)c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(CC3CCCCC3)c2)c(Cl)c1 BBFODUJPSOVNMA-UHFFFAOYSA-N 0.000 claims description 7
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NDPAJCXXGDZROA-UHFFFAOYSA-N Fc1ccc(-c2nc(cs2)-c2ccc(NS(=O)(=O)C(F)(F)F)cc2Cl)c(CN2CCCC2)c1 Chemical compound Fc1ccc(-c2nc(cs2)-c2ccc(NS(=O)(=O)C(F)(F)F)cc2Cl)c(CN2CCCC2)c1 NDPAJCXXGDZROA-UHFFFAOYSA-N 0.000 claims description 7
XDMJBGYXZBTZFN-UHFFFAOYSA-N N-[3-chloro-4-[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]phenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2c[nH]c3ccccc23)c(Cl)c1 XDMJBGYXZBTZFN-UHFFFAOYSA-N 0.000 claims description 7
MEYDTVNYAVMTBP-UHFFFAOYSA-N Nc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Nc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl MEYDTVNYAVMTBP-UHFFFAOYSA-N 0.000 claims description 7
RDVUFHKRBVVCBV-UHFFFAOYSA-N OCc1cccc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound OCc1cccc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl RDVUFHKRBVVCBV-UHFFFAOYSA-N 0.000 claims description 7
XAZYKQZJHBNDIG-UHFFFAOYSA-N OCc1ccccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound OCc1ccccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl XAZYKQZJHBNDIG-UHFFFAOYSA-N 0.000 claims description 7
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 7
RZNMDTUUTDSKEY-UHFFFAOYSA-N CC(C)Cn1nccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)Cn1nccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl RZNMDTUUTDSKEY-UHFFFAOYSA-N 0.000 claims description 6
GEPBXJOWWZLAIG-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 GEPBXJOWWZLAIG-UHFFFAOYSA-N 0.000 claims description 6
YJNJSSGEQFXGSF-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1cccc(NS(=O)(=O)C(F)(F)F)c1 Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1cccc(NS(=O)(=O)C(F)(F)F)c1 YJNJSSGEQFXGSF-UHFFFAOYSA-N 0.000 claims description 6
XJMNVUFRIBZOBD-UHFFFAOYSA-N COc1cc(ccc1NS(=O)(=O)C(F)(F)F)-c1csc(n1)-c1ccnc(CC(C)C)c1 Chemical compound COc1cc(ccc1NS(=O)(=O)C(F)(F)F)-c1csc(n1)-c1ccnc(CC(C)C)c1 XJMNVUFRIBZOBD-UHFFFAOYSA-N 0.000 claims description 6
YIVDKLRLGXPAAW-UHFFFAOYSA-N CS(=O)(=O)Nc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CS(=O)(=O)Nc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl YIVDKLRLGXPAAW-UHFFFAOYSA-N 0.000 claims description 6
ULMAWMLEXMEKAB-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccc(cc2)C(=O)N2CCCCC2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccc(cc2)C(=O)N2CCCCC2)c(Cl)c1 ULMAWMLEXMEKAB-UHFFFAOYSA-N 0.000 claims description 6
VYXASUWXEUTULH-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(NS(=O)(=O)C(F)(F)F)c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(NS(=O)(=O)C(F)(F)F)c2)c(Cl)c1 VYXASUWXEUTULH-UHFFFAOYSA-N 0.000 claims description 6
VMICVFBKNJAKCG-UHFFFAOYSA-N Fc1cnc2[nH]ccc2c1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Fc1cnc2[nH]ccc2c1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl VMICVFBKNJAKCG-UHFFFAOYSA-N 0.000 claims description 6
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
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125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
KKHZGRDVHRWOFN-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(OC)c1 Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(OC)c1 KKHZGRDVHRWOFN-UHFFFAOYSA-N 0.000 claims description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
230000008569 process Effects 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
RONJAUBGKUZIIA-UHFFFAOYSA-N CC(C)(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl RONJAUBGKUZIIA-UHFFFAOYSA-N 0.000 claims description 3
SYPNOKMGJNRXRN-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1coc(n1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)(C)c1cc(ccn1)-c1coc(n1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl SYPNOKMGJNRXRN-UHFFFAOYSA-N 0.000 claims description 3
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LXPSIIKTISUHHA-UHFFFAOYSA-N CCCn1cnc2c(ccnc12)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCn1cnc2c(ccnc12)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl LXPSIIKTISUHHA-UHFFFAOYSA-N 0.000 claims description 3
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ATWYBVFFIAVOJB-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(cc1Br)-c1c[nH]c(n1)-c1ccnc(c1)N1CCCCC1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(cc1Br)-c1c[nH]c(n1)-c1ccnc(c1)N1CCCCC1 ATWYBVFFIAVOJB-UHFFFAOYSA-N 0.000 claims description 3
VXFVFUMFDXZRRQ-UHFFFAOYSA-N Fc1ccc(cc1C(=O)NC1CC1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Fc1ccc(cc1C(=O)NC1CC1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl VXFVFUMFDXZRRQ-UHFFFAOYSA-N 0.000 claims description 3
VMUDMXBCBDQDSU-UHFFFAOYSA-N Fc1ccc(cc1C(=O)NC1CCCCC1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Fc1ccc(cc1C(=O)NC1CCCCC1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl VMUDMXBCBDQDSU-UHFFFAOYSA-N 0.000 claims description 3
HKYUIJUHVBFMAP-UHFFFAOYSA-N N-[4-[2-(2-tert-butylpyridin-4-yl)-1,3-thiazol-4-yl]-2-hydroxyphenyl]-1,1,1-trifluoromethanesulfonamide Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(O)c1 HKYUIJUHVBFMAP-UHFFFAOYSA-N 0.000 claims description 3
ZDPGBIVLDCUWGD-UHFFFAOYSA-N Nc1nccc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Nc1nccc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl ZDPGBIVLDCUWGD-UHFFFAOYSA-N 0.000 claims description 3
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125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 3
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 3
229940124530 sulfonamide Drugs 0.000 claims description 3
150000003456 sulfonamides Chemical class 0.000 claims description 3
KPMLEDOPCIUYAZ-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)Cc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl KPMLEDOPCIUYAZ-UHFFFAOYSA-N 0.000 claims 2
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