JP2018507234A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2018507234A5 JP2018507234A5 JP2017546185A JP2017546185A JP2018507234A5 JP 2018507234 A5 JP2018507234 A5 JP 2018507234A5 JP 2017546185 A JP2017546185 A JP 2017546185A JP 2017546185 A JP2017546185 A JP 2017546185A JP 2018507234 A5 JP2018507234 A5 JP 2018507234A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- phenyl
- trifluoromethanesulfonamide
- chloro
- linear
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- -1 1-propyl-1H-pyrrolo [2,3-b] pyridin-4-yl Chemical group 0.000 claims description 137
- 150000001875 compounds Chemical class 0.000 claims description 74
- 229910052739 hydrogen Inorganic materials 0.000 claims description 69
- 239000001257 hydrogen Substances 0.000 claims description 69
- 125000000217 alkyl group Chemical group 0.000 claims description 61
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000005843 halogen group Chemical group 0.000 claims description 49
- 229910052736 halogen Inorganic materials 0.000 claims description 43
- 150000002367 halogens Chemical class 0.000 claims description 43
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 27
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims description 24
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 23
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 22
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 20
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 20
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 17
- 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 17
- 206010014476 Elevated cholesterol Diseases 0.000 claims description 16
- 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 16
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 16
- 206010022489 Insulin Resistance Diseases 0.000 claims description 16
- 150000001408 amides Chemical class 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 16
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 16
- 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 15
- 125000000304 alkynyl group Chemical group 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
- 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 14
- 208000019425 cirrhosis of liver Diseases 0.000 claims description 14
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 13
- 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 12
- 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 12
- 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 12
- 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 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 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
- 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 9
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 9
- 239000011734 sodium Substances 0.000 claims description 9
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- PRXNRYRCCJJWJA-UHFFFAOYSA-N Cc1noc(C)c1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Cc1noc(C)c1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl PRXNRYRCCJJWJA-UHFFFAOYSA-N 0.000 claims description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 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 8
- 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 8
- 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 8
- 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 8
- UBZLTIMABBDUSQ-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(NC3CCCC3)c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(NC3CCCC3)c2)c(Cl)c1 UBZLTIMABBDUSQ-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- BEFDVPKBVJWWSW-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cncc3ccccc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2cncc3ccccc23)c(Cl)c1 BEFDVPKBVJWWSW-UHFFFAOYSA-N 0.000 claims description 8
- VUXHOFXQHFESDU-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2csc3ccccc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2csc3ccccc23)c(Cl)c1 VUXHOFXQHFESDU-UHFFFAOYSA-N 0.000 claims description 8
- DMYLMEMGMAHSHD-UHFFFAOYSA-N FC(F)(F)c1ccc(cc1OCc1ccccc1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound FC(F)(F)c1ccc(cc1OCc1ccccc1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl DMYLMEMGMAHSHD-UHFFFAOYSA-N 0.000 claims description 8
- 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 8
- 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 8
- 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 8
- 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 8
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- SXCHDDWMFBETRA-UHFFFAOYSA-N oxazinan-3-one Chemical compound O=C1CCCON1 SXCHDDWMFBETRA-UHFFFAOYSA-N 0.000 claims description 8
- XGYCWCIGCYGQFU-UHFFFAOYSA-N 1,2-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCCN1 XGYCWCIGCYGQFU-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 239000003814 drug Substances 0.000 claims description 7
- VKHFWQBYJLLQEP-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc3ccccc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc3ccccc23)c(Cl)c1 VKHFWQBYJLLQEP-UHFFFAOYSA-N 0.000 claims description 6
- QVVFDNGMCBYQRW-UHFFFAOYSA-N Fc1ccc(-c2nc(cs2)-c2ccc(NS(=O)(=O)C(F)(F)F)cc2Cl)c(c1)C(F)(F)F Chemical compound Fc1ccc(-c2nc(cs2)-c2ccc(NS(=O)(=O)C(F)(F)F)cc2Cl)c(c1)C(F)(F)F QVVFDNGMCBYQRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[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 4
- 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 4
- XWZREOLYQIBHME-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 XWZREOLYQIBHME-UHFFFAOYSA-N 0.000 claims description 4
- JBRYTIGCKDNBFH-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(co1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(co1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl JBRYTIGCKDNBFH-UHFFFAOYSA-N 0.000 claims description 4
- RMPYKFLRNFKZBU-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1Cl Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1Cl RMPYKFLRNFKZBU-UHFFFAOYSA-N 0.000 claims description 4
- KUUCALUUCYULIF-UHFFFAOYSA-N CC(C)Cc1cc(ccc1F)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)Cc1cc(ccc1F)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl KUUCALUUCYULIF-UHFFFAOYSA-N 0.000 claims description 4
- 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 description 4
- KWXWRYKFWMUIPK-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1c(Cl)cc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1c(Cl)cc(NS(=O)(=O)C(F)(F)F)cc1Cl KWXWRYKFWMUIPK-UHFFFAOYSA-N 0.000 claims description 4
- HZLUMXCZROCUKD-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1cc(C)c(NS(=O)(=O)C(F)(F)F)c(Cl)c1 Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1cc(C)c(NS(=O)(=O)C(F)(F)F)c(Cl)c1 HZLUMXCZROCUKD-UHFFFAOYSA-N 0.000 claims description 4
- RMXDULFJLIJTRK-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1cc(Cl)c(NS(=O)(=O)C(F)(F)F)c(Br)c1 Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1cc(Cl)c(NS(=O)(=O)C(F)(F)F)c(Br)c1 RMXDULFJLIJTRK-UHFFFAOYSA-N 0.000 claims description 4
- SUDBHAUPJIKMBA-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)C(F)(F)F)cc1Cl Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)C(F)(F)F)cc1Cl SUDBHAUPJIKMBA-UHFFFAOYSA-N 0.000 claims description 4
- WOPJXKKSYIWWLJ-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 WOPJXKKSYIWWLJ-UHFFFAOYSA-N 0.000 claims description 4
- FFHGYQBZUOSWPN-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1C#C Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1C#C FFHGYQBZUOSWPN-UHFFFAOYSA-N 0.000 claims description 4
- BJGVQGNCIQTDTF-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1Cl Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1Cl BJGVQGNCIQTDTF-UHFFFAOYSA-N 0.000 claims description 4
- WXUPPABRAMFLFL-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C#C Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C#C WXUPPABRAMFLFL-UHFFFAOYSA-N 0.000 claims description 4
- NNYQCFIXPNYKKV-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C1CC1 Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C1CC1 NNYQCFIXPNYKKV-UHFFFAOYSA-N 0.000 claims description 4
- ZXTIYSCMXVXODX-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc2n(c(=O)oc2c1)S(=O)(=O)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc2n(c(=O)oc2c1)S(=O)(=O)C(F)(F)F ZXTIYSCMXVXODX-UHFFFAOYSA-N 0.000 claims description 4
- CKWQZKPBTYPTFV-UHFFFAOYSA-N CC(C)Cc1nc(N)cc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)Cc1nc(N)cc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl CKWQZKPBTYPTFV-UHFFFAOYSA-N 0.000 claims description 4
- WASCWUYBJICKFQ-UHFFFAOYSA-N CCCCN(CCCC)c1nccc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCCN(CCCC)c1nccc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl WASCWUYBJICKFQ-UHFFFAOYSA-N 0.000 claims description 4
- AHYJBEUSFAWCQG-UHFFFAOYSA-N CCCCNc1cc(nc(CC(C)C)n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCCNc1cc(nc(CC(C)C)n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl AHYJBEUSFAWCQG-UHFFFAOYSA-N 0.000 claims description 4
- RCMLYDROVVYDIP-UHFFFAOYSA-N CCCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 Chemical compound CCCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 RCMLYDROVVYDIP-UHFFFAOYSA-N 0.000 claims description 4
- XRCJTKBNOIKCGK-UHFFFAOYSA-N CCCNc1nccc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCNc1nccc(n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl XRCJTKBNOIKCGK-UHFFFAOYSA-N 0.000 claims description 4
- YZYCJDRLBLEFBI-UHFFFAOYSA-N CCCc1cc(CCC)nc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 Chemical compound CCCc1cc(CCC)nc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 YZYCJDRLBLEFBI-UHFFFAOYSA-N 0.000 claims description 4
- VGYMKYLMGZQFKQ-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(c[nH]1)-c1cc(Br)c(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1cc(ccn1)-c1nc(c[nH]1)-c1cc(Br)c(NS(=O)(=O)C(F)(F)F)cc1Cl VGYMKYLMGZQFKQ-UHFFFAOYSA-N 0.000 claims description 4
- COBXGCBLHINYFX-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 Chemical compound CCCc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 COBXGCBLHINYFX-UHFFFAOYSA-N 0.000 claims description 4
- HSWSADJZQDGSRO-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1Cl Chemical compound CCCc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1Cl HSWSADJZQDGSRO-UHFFFAOYSA-N 0.000 claims description 4
- AXHRHZCDDIANHM-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Cl)c1 Chemical compound CCCc1cc(ccn1)-c1nc(c[nH]1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Cl)c1 AXHRHZCDDIANHM-UHFFFAOYSA-N 0.000 claims description 4
- GITRQNPETXTTSJ-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cn1C)-c1cc(Br)c(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1cc(ccn1)-c1nc(cn1C)-c1cc(Br)c(NS(=O)(=O)C(F)(F)F)cc1Cl GITRQNPETXTTSJ-UHFFFAOYSA-N 0.000 claims description 4
- SGDQPQYSDIKGPG-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cn1C)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 Chemical compound CCCc1cc(ccn1)-c1nc(cn1C)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 SGDQPQYSDIKGPG-UHFFFAOYSA-N 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
- ANPZQWPJCBLJHS-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(C)S(=O)(=O)C(F)(F)F Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(C)S(=O)(=O)C(F)(F)F ANPZQWPJCBLJHS-UHFFFAOYSA-N 0.000 claims description 4
- YYUHWTFNRXTPGV-UHFFFAOYSA-N CCCc1cc2c(ccnc2n1CCC)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1cc2c(ccnc2n1CCC)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl YYUHWTFNRXTPGV-UHFFFAOYSA-N 0.000 claims description 4
- DNKSUCXWKGBPRD-UHFFFAOYSA-N CCCc1ccc(-c2nc(cs2)-c2ccc(NS(=O)(=O)C(F)(F)F)cc2)c(CCC)n1 Chemical compound CCCc1ccc(-c2nc(cs2)-c2ccc(NS(=O)(=O)C(F)(F)F)cc2)c(CCC)n1 DNKSUCXWKGBPRD-UHFFFAOYSA-N 0.000 claims description 4
- RVXSFXHNKDEHDW-UHFFFAOYSA-N CCCc1nc(cs1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1nc(cs1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl RVXSFXHNKDEHDW-UHFFFAOYSA-N 0.000 claims description 4
- SOZRDWPYJSIXNY-UHFFFAOYSA-N CCCc1nc(no1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1nc(no1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl SOZRDWPYJSIXNY-UHFFFAOYSA-N 0.000 claims description 4
- CUDDJFGJUIQWAI-UHFFFAOYSA-N CCCc1nc(ns1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1nc(ns1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl CUDDJFGJUIQWAI-UHFFFAOYSA-N 0.000 claims description 4
- PFYCFQQNHMVVOR-UHFFFAOYSA-N CCCc1nc2c(ccnc2[nH]1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1nc2c(ccnc2[nH]1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl PFYCFQQNHMVVOR-UHFFFAOYSA-N 0.000 claims description 4
- GLHSDVDIXQZMPW-UHFFFAOYSA-N CCCc1ncc(s1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1ncc(s1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl GLHSDVDIXQZMPW-UHFFFAOYSA-N 0.000 claims description 4
- HHGVJIVCXHIFCX-UHFFFAOYSA-N CCCc1nnc(o1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1nnc(o1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl HHGVJIVCXHIFCX-UHFFFAOYSA-N 0.000 claims description 4
- QTCDVBYGRGTMPC-UHFFFAOYSA-N CCCc1nnc(s1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCc1nnc(s1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl QTCDVBYGRGTMPC-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- FNXCSUZDPWZWMI-UHFFFAOYSA-N CCN(CC)CCN(c1ccc(-c2csc(n2)-c2ccnc(CC(C)C)c2)c(Cl)c1)S(=O)(=O)C(F)(F)F Chemical compound CCN(CC)CCN(c1ccc(-c2csc(n2)-c2ccnc(CC(C)C)c2)c(Cl)c1)S(=O)(=O)C(F)(F)F FNXCSUZDPWZWMI-UHFFFAOYSA-N 0.000 claims description 4
- YDENHWSZYROYMF-UHFFFAOYSA-N CN(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CN(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl YDENHWSZYROYMF-UHFFFAOYSA-N 0.000 claims description 4
- WPYFUKXBSTVIRG-UHFFFAOYSA-N Cc1cc2c(ccnc2n1C)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Cc1cc2c(ccnc2n1C)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl WPYFUKXBSTVIRG-UHFFFAOYSA-N 0.000 claims description 4
- JVEKTAZFQMPZKI-UHFFFAOYSA-N Cc1nc2c(ccnc2n1C)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound Cc1nc2c(ccnc2n1C)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl JVEKTAZFQMPZKI-UHFFFAOYSA-N 0.000 claims description 4
- RAJAAUBZCFXNJM-UHFFFAOYSA-N Cn1cc(nc1-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl)-c1ccnc(c1)C(C)(C)C Chemical compound Cn1cc(nc1-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl)-c1ccnc(c1)C(C)(C)C RAJAAUBZCFXNJM-UHFFFAOYSA-N 0.000 claims description 4
- HARNXARLWFVHEL-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(Cl)c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc(Cl)c2)c(Cl)c1 HARNXARLWFVHEL-UHFFFAOYSA-N 0.000 claims description 4
- MXVMTFZPLNHYFG-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc3[nH]ccc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc3[nH]ccc23)c(Cl)c1 MXVMTFZPLNHYFG-UHFFFAOYSA-N 0.000 claims description 4
- DJWJEAYOZPZTTD-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc3[nH]cnc23)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccnc3[nH]cnc23)c(Cl)c1 DJWJEAYOZPZTTD-UHFFFAOYSA-N 0.000 claims description 4
- HNVCLXNAADTCHB-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(cc1)-c1csc(n1)-c1ccnc(CC2CCCCC2)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(cc1)-c1csc(n1)-c1ccnc(CC2CCCCC2)c1 HNVCLXNAADTCHB-UHFFFAOYSA-N 0.000 claims description 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- 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 4
- JKQPSITVMHAPMJ-UHFFFAOYSA-M P(=O)(ON(S(=O)(=O)C(F)(F)F)C1=CC(=C(C=C1)C=1N=C(SC=1)C1=CC(=NC=C1)C(C)(C)C)Cl)(OC)[O-].[Na+] Chemical compound P(=O)(ON(S(=O)(=O)C(F)(F)F)C1=CC(=C(C=C1)C=1N=C(SC=1)C1=CC(=NC=C1)C(C)(C)C)Cl)(OC)[O-].[Na+] JKQPSITVMHAPMJ-UHFFFAOYSA-M 0.000 claims description 4
- 125000000814 indol-3-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C([*])C2=C1[H] 0.000 claims description 4
- 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 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 4
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 22
- 206010019668 Hepatic fibrosis Diseases 0.000 claims 2
- 229940124530 sulfonamide Drugs 0.000 claims 2
- 150000003456 sulfonamides Chemical class 0.000 claims 2
- KAKQVSNHTBLJCH-UHFFFAOYSA-N trifluoromethanesulfonimidic acid Chemical compound NS(=O)(=O)C(F)(F)F KAKQVSNHTBLJCH-UHFFFAOYSA-N 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 1
- 0 Cc1c(*)c(*)c(*)c(N(*)*)c1 Chemical compound Cc1c(*)c(*)c(*)c(N(*)*)c1 0.000 description 24
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 16
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 5
- MOOHIXDFNMSRCE-UHFFFAOYSA-N C(C1CCCCC1)c1ncccc1 Chemical compound C(C1CCCCC1)c1ncccc1 MOOHIXDFNMSRCE-UHFFFAOYSA-N 0.000 description 2
- LLSKXGRDUPMXLC-UHFFFAOYSA-N C(CC1)CCN1c1ccccc1 Chemical compound C(CC1)CCN1c1ccccc1 LLSKXGRDUPMXLC-UHFFFAOYSA-N 0.000 description 2
- XHPVOSNOIWGRQQ-UHFFFAOYSA-N C(COCC1)N1c1ccccn1 Chemical compound C(COCC1)N1c1ccccn1 XHPVOSNOIWGRQQ-UHFFFAOYSA-N 0.000 description 2
- PCFUWBOSXMKGIP-UHFFFAOYSA-N C(c1ccccc1)c1ccccn1 Chemical compound C(c1ccccc1)c1ccccn1 PCFUWBOSXMKGIP-UHFFFAOYSA-N 0.000 description 2
- KNDJNVWEKSLWOV-UHFFFAOYSA-N CC(C)(C)Cc1ncccc1 Chemical compound CC(C)(C)Cc1ncccc1 KNDJNVWEKSLWOV-UHFFFAOYSA-N 0.000 description 2
- BBVSPSDWPYWMOR-UHFFFAOYSA-N CC(C)Cc1ncccc1 Chemical compound CC(C)Cc1ncccc1 BBVSPSDWPYWMOR-UHFFFAOYSA-N 0.000 description 2
- MLDOXGCWVQXLNA-UHFFFAOYSA-N CC(C=C1)(C=CN=C1N)NC Chemical compound CC(C=C1)(C=CN=C1N)NC MLDOXGCWVQXLNA-UHFFFAOYSA-N 0.000 description 2
- NFUZNLAPCPTNDY-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(Br)c1 NFUZNLAPCPTNDY-UHFFFAOYSA-N 0.000 description 2
- GVSNZBKVNVRUDM-UHFFFAOYSA-N CCCc1cccc(CCC)n1 Chemical compound CCCc1cccc(CCC)n1 GVSNZBKVNVRUDM-UHFFFAOYSA-N 0.000 description 2
- OIALIKXMLIAOSN-UHFFFAOYSA-N CCCc1ncccc1 Chemical compound CCCc1ncccc1 OIALIKXMLIAOSN-UHFFFAOYSA-N 0.000 description 2
- MDHKWAZLVNUABG-UHFFFAOYSA-N CN(CC1)CCN1c1ncccc1 Chemical compound CN(CC1)CCN1c1ncccc1 MDHKWAZLVNUABG-UHFFFAOYSA-N 0.000 description 2
- QDTSINVSGKAPBV-UHFFFAOYSA-N COCc1ncccc1 Chemical compound COCc1ncccc1 QDTSINVSGKAPBV-UHFFFAOYSA-N 0.000 description 2
- OKDGRDCXVWSXDC-UHFFFAOYSA-N Clc1ncccc1 Chemical compound Clc1ncccc1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 description 2
- AJEUJXWLOADTKA-UHFFFAOYSA-N C(CC1)CCN1c1ncccc1 Chemical compound C(CC1)CCN1c1ncccc1 AJEUJXWLOADTKA-UHFFFAOYSA-N 0.000 description 1
- VNHLAVQFKNFAEI-UHFFFAOYSA-N CC(C)(C)c1cc(I)ccn1 Chemical compound CC(C)(C)c1cc(I)ccn1 VNHLAVQFKNFAEI-UHFFFAOYSA-N 0.000 description 1
- KYVAUVHALBXNNH-UHFFFAOYSA-N CC(C)(C)c1ccc(C[I](C)C)cn1 Chemical compound CC(C)(C)c1ccc(C[I](C)C)cn1 KYVAUVHALBXNNH-UHFFFAOYSA-N 0.000 description 1
- UUIMDJFBHNDZOW-UHFFFAOYSA-N CC(C)(C)c1ncccc1 Chemical compound CC(C)(C)c1ncccc1 UUIMDJFBHNDZOW-UHFFFAOYSA-N 0.000 description 1
- GDLBNZRUFWZJLD-UHFFFAOYSA-N CC(C)(C=C1)C=CN=C1NS(C(F)(F)F)(=O)=O Chemical compound CC(C)(C=C1)C=CN=C1NS(C(F)(F)F)(=O)=O GDLBNZRUFWZJLD-UHFFFAOYSA-N 0.000 description 1
- IWKQDQNCBKSTAP-GHXNOFRVSA-N CC(C)CN/N=C\C(C)=C(C)C Chemical compound CC(C)CN/N=C\C(C)=C(C)C IWKQDQNCBKSTAP-GHXNOFRVSA-N 0.000 description 1
- TVTDDTMWXCTKCZ-UHFFFAOYSA-N CC(C)Cc1cc(I)ccn1 Chemical compound CC(C)Cc1cc(I)ccn1 TVTDDTMWXCTKCZ-UHFFFAOYSA-N 0.000 description 1
- UJUVAKOJHXGPJJ-UHFFFAOYSA-N CC(C)Cc1cc(NC)ccn1 Chemical compound CC(C)Cc1cc(NC)ccn1 UJUVAKOJHXGPJJ-UHFFFAOYSA-N 0.000 description 1
- IIIRAIOXRZQGGU-KDAGLMFCSA-N CCC/C(/C=C\C(C)C)=C/C=N Chemical compound CCC/C(/C=C\C(C)C)=C/C=N IIIRAIOXRZQGGU-KDAGLMFCSA-N 0.000 description 1
- MLAXEZHEGARMPE-UHFFFAOYSA-N CCCc1cnccc1 Chemical compound CCCc1cnccc1 MLAXEZHEGARMPE-UHFFFAOYSA-N 0.000 description 1
- PBGNLJCYFXOBRO-UHFFFAOYSA-N CN(C)c1cc(C(F)(F)F)ncc1 Chemical compound CN(C)c1cc(C(F)(F)F)ncc1 PBGNLJCYFXOBRO-UHFFFAOYSA-N 0.000 description 1
- OQEXWNOXWMKQOR-UHFFFAOYSA-N CN(C)c1cc(CCC(F)(F)F)ncc1 Chemical compound CN(C)c1cc(CCC(F)(F)F)ncc1 OQEXWNOXWMKQOR-UHFFFAOYSA-N 0.000 description 1
- YSFQRZUOBNSRBL-UHFFFAOYSA-N CN(C)c1ccc(NS(C)(=O)=O)nc1 Chemical compound CN(C)c1ccc(NS(C)(=O)=O)nc1 YSFQRZUOBNSRBL-UHFFFAOYSA-N 0.000 description 1
- WRXXFCQSCCRKPQ-UHFFFAOYSA-N CN(C)c1ccnc(CC(F)(F)F)c1 Chemical compound CN(C)c1ccnc(CC(F)(F)F)c1 WRXXFCQSCCRKPQ-UHFFFAOYSA-N 0.000 description 1
- HSYQBVWWEUNMDK-UHFFFAOYSA-N FC(CCc1cc(I)ccn1)(F)F Chemical compound FC(CCc1cc(I)ccn1)(F)F HSYQBVWWEUNMDK-UHFFFAOYSA-N 0.000 description 1
- CMRUIGOIRUFXGM-UHFFFAOYSA-N FC(CCc1ccccn1)(F)F Chemical compound FC(CCc1ccccn1)(F)F CMRUIGOIRUFXGM-UHFFFAOYSA-N 0.000 description 1
- MKFDWZKRIACKMS-UHFFFAOYSA-N FC(Cc1ncccc1)(F)F Chemical compound FC(Cc1ncccc1)(F)F MKFDWZKRIACKMS-UHFFFAOYSA-N 0.000 description 1
- ATRQECRSCHYSNP-UHFFFAOYSA-N FC(c1ncccc1)(F)F Chemical compound FC(c1ncccc1)(F)F ATRQECRSCHYSNP-UHFFFAOYSA-N 0.000 description 1
- LGZRYKBLSRMSCJ-UHFFFAOYSA-N Ic1cc(N2CCCCC2)ccc1 Chemical compound Ic1cc(N2CCCCC2)ccc1 LGZRYKBLSRMSCJ-UHFFFAOYSA-N 0.000 description 1
- UBFRXHNATRZWSV-UHFFFAOYSA-N Ic1ccnc(N2CCCCC2)c1 Chemical compound Ic1ccnc(N2CCCCC2)c1 UBFRXHNATRZWSV-UHFFFAOYSA-N 0.000 description 1
- SIKJAQJRHWYJAI-UHFFFAOYSA-N c1c[nH]c2c1cccc2 Chemical compound c1c[nH]c2c1cccc2 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 1
- OZQGLZFAWYKKLQ-UHFFFAOYSA-N oxazinane Chemical compound C1CCONC1 OZQGLZFAWYKKLQ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562128251P | 2015-03-04 | 2015-03-04 | |
| US62/128,251 | 2015-03-04 | ||
| PCT/US2016/020644 WO2016141159A1 (en) | 2015-03-04 | 2016-03-03 | Srebp blockers for use in treating liver fibrosis, elevated cholesterol and insulin resistance |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2018507234A JP2018507234A (ja) | 2018-03-15 |
| JP2018507234A5 true JP2018507234A5 (enExample) | 2019-04-18 |
Family
ID=55754401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017546185A Withdrawn JP2018507234A (ja) | 2015-03-04 | 2016-03-03 | 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 |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US10183015B2 (enExample) |
| EP (1) | EP3265088A1 (enExample) |
| JP (1) | JP2018507234A (enExample) |
| CA (1) | CA2978627A1 (enExample) |
| WO (1) | WO2016141159A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016105491A1 (en) | 2014-12-23 | 2016-06-30 | Fgh Biotech | Compositions of fatostatin based heterocyclic compounds and uses thereof |
| WO2016141258A1 (en) | 2015-03-04 | 2016-09-09 | Medivation Technologies, Inc. | Sterol regulatory element-binding proteins (srebps) inhibitors |
| WO2017190086A1 (en) | 2016-04-29 | 2017-11-02 | Fgh Biotech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| CA3036195A1 (en) | 2016-09-07 | 2018-03-15 | Fgh Biotech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| JP2021512160A (ja) * | 2018-01-29 | 2021-05-13 | カピュラス セラピューティクス リミテッド ライアビリティ カンパニー | ６員の中央環を含むｓｒｅｂｐ阻害剤 |
| CN113631163A (zh) * | 2019-01-28 | 2021-11-09 | 卡普勒斯疗法有限责任公司 | 包括噻吩中心环的srebp抑制剂 |
| WO2020191163A1 (en) * | 2019-03-20 | 2020-09-24 | Regeneron Pharmaceuticals, Inc. | Treatment of increased lipid levels with sterol regulatory element binding protein cleavage-activating protein (scap) inhibitors |
| CA3157442A1 (en) * | 2019-11-13 | 2021-05-20 | Capulus Therapeutics, Llc | Srebp inhibitor comprising a thiophene central ring |
| JP2023502603A (ja) * | 2019-11-13 | 2023-01-25 | カピュラス セラピューティクス リミテッド ライアビリティ カンパニー | 環状アミドを有するチオフェン化合物およびそれらの使用 |
| WO2021154735A1 (en) * | 2020-01-27 | 2021-08-05 | Capulus Therapeutics, Llc | Srebp inhibitors comprising a thiophene central ring |
| WO2022020738A1 (en) * | 2020-07-24 | 2022-01-27 | Capulus Therapeutics, Llc | Srebp inhibitors comprising a thiophene central ring |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL96891A0 (en) | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| DE69902754T2 (de) | 1998-02-09 | 2003-08-07 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl-amidinen,-methylamidinen und -guanidinen als protease inhibitoren, insbesondere als urokinase inhibitoren |
| US6291514B1 (en) | 1998-02-09 | 2001-09-18 | 3-Dimensional Pharmaceuticals, Inc. | Heteroaryl amidines, methylamidines and guanidines, preparation thereof, and use thereof as protease inhibitors |
| JP4180276B2 (ja) | 1999-12-16 | 2008-11-12 | シェーリング コーポレイション | 置換イミダゾール神経ペプチドｙｙ５レセプタアンタゴニスト |
| TWI275589B (en) | 2000-06-22 | 2007-03-11 | Dow Agrosciences Llc | 2-(3,5-disubstituted-4-pyridyl)-4-(thienyl, thiazolyl or arylphenyl)-1,3-oxazoline compounds |
| WO2004110350A2 (en) | 2003-05-14 | 2004-12-23 | Torreypines Therapeutics, Inc. | Compouds and uses thereof in modulating amyloid beta |
| BRPI0612028A2 (pt) | 2005-06-08 | 2010-10-13 | Novartis Ag | oxadiazóis ou isodiazóis policìclicos e uso dos mesmos como ligantes de receptor s1p |
| MX2007015729A (es) | 2005-06-09 | 2008-02-21 | Schering Plough Ltd | Control de parasitos en animales con derivados de n-[(feniloxi)fenil]-1,1,1-trifluorometansulfonamida y de n[(fenilsulfanil)fenil]-1,1,1-trifluorometansulfonamida. |
| SI1907382T1 (sl) | 2005-07-26 | 2015-10-30 | Bial-Portela & Ca S.A., | Nitrokateholni derivati kot inhibitorji COMT |
| WO2007021941A2 (en) | 2005-08-16 | 2007-02-22 | Icagen, Inc. | Inhibitors of voltage-gated sodium channels |
| US8229106B2 (en) | 2007-01-22 | 2012-07-24 | D.S.P. Group, Ltd. | Apparatus and methods for enhancement of speech |
| US9187485B2 (en) | 2007-02-02 | 2015-11-17 | Baylor College Of Medicine | Methods and compositions for the treatment of cancer and related hyperproliferative disorders |
| CA2677264C (en) | 2007-02-02 | 2021-11-30 | Baylor College Of Medicine | Compositions and methods for the treatment of metabolic disorders |
| US9212179B2 (en) | 2007-02-02 | 2015-12-15 | Baylor College Of Medicine | Compositions and methods for the treatment of metabolic disorders |
| DK2125797T3 (da) | 2007-03-16 | 2014-02-10 | Actelion Pharmaceuticals Ltd | Aminopyridinderivater som s1p1/edg1-receptoragonister |
| KR20100110834A (ko) | 2007-12-21 | 2010-10-13 | 메르크 세로노 에스. 에이. | 트리아졸 옥사다이아졸 유도체 |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| WO2011085269A1 (en) | 2010-01-08 | 2011-07-14 | Selexagen Therapeutics, Inc. | Raf kinase inhibitors |
| WO2012084678A1 (en) | 2010-12-23 | 2012-06-28 | Syngenta Participations Ag | Novel imidazoles useful as plant fungicides |
| JP2014062047A (ja) | 2011-01-21 | 2014-04-10 | Taisho Pharmaceutical Co Ltd | ピラゾール誘導体 |
| GB201116017D0 (en) | 2011-09-16 | 2011-10-26 | Univ Surrey | Bi-aromatic and tri-aromatic compounds as nadph oxidase inhibitors |
| US20130165472A1 (en) | 2011-12-23 | 2013-06-27 | Millennium Pharmaceuticals, Inc. | Heteroaryls and uses thereof |
| WO2013110007A1 (en) | 2012-01-18 | 2013-07-25 | The Trustees Of Columbia University In The City Of New York | USE OF FATOSTATIN FOR TREATING CANCER HAVING A p53 MUTATION |
| WO2014199164A1 (en) | 2013-06-12 | 2014-12-18 | Ampla Pharmaceuticals, Inc. | Diaryl substituted heteroaromatic compounds |
| KR20160037169A (ko) | 2013-06-26 | 2016-04-05 | 레트 신드롬 리서치 트러스트 | 레트 증후군 및 그를 위한 치료 |
| DK3038622T3 (en) | 2013-08-28 | 2018-07-16 | Medivation Tech Llc | HETEROCYCLIC RELATIONS AND PROCEDURES FOR USE |
| WO2016141258A1 (en) | 2015-03-04 | 2016-09-09 | Medivation Technologies, Inc. | Sterol regulatory element-binding proteins (srebps) inhibitors |
-
2016
- 2016-03-03 EP EP16716719.6A patent/EP3265088A1/en not_active Withdrawn
- 2016-03-03 WO PCT/US2016/020644 patent/WO2016141159A1/en not_active Ceased
- 2016-03-03 JP JP2017546185A patent/JP2018507234A/ja not_active Withdrawn
- 2016-03-03 US US15/553,589 patent/US10183015B2/en not_active Expired - Fee Related
- 2016-03-03 CA CA2978627A patent/CA2978627A1/en not_active Abandoned