JP2018507234A5 - - Google Patents
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- 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- Withdrawn
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- -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
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- 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
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| PCT/US2016/020644 WO2016141159A1 (en) | 2015-03-04 | 2016-03-03 | Srebp blockers for use in treating liver fibrosis, elevated cholesterol and insulin resistance |
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| US10328064B2 (en) | 2014-12-23 | 2019-06-25 | Fgh Biotech, Inc. | Compositions of fatostatin based heterocyclic compounds and uses thereof |
| EP3265457A1 (en) | 2015-03-04 | 2018-01-10 | Medivation Technologies LLC | Sterol regulatory element-binding proteins (srebps) inhibitors |
| JP6931695B2 (ja) | 2016-04-29 | 2021-09-08 | エフジーエイチ バイオテック，インコーポレーテッド | 疾患の治療のための二置換ピラゾール化合物 |
| WO2018049080A1 (en) | 2016-09-07 | 2018-03-15 | Fgh Biotech, Inc. | Di-substituted pyrazole compounds for the treatment of diseases |
| CA3089134A1 (en) | 2018-01-29 | 2019-08-01 | Capulus Therapeutics, Llc | Srebp inhibitors comprising a 6-membered central ring |
| EP3917513A4 (en) * | 2019-01-28 | 2022-11-09 | Capulus Therapeutics, LLC | SREBP INHIBITORS WITH A THIOPHENE CENTER RING |
| US11331332B2 (en) * | 2019-03-20 | 2022-05-17 | Regeneron Pharmaceuticals, Inc. | Treatment of increased lipid levels with sterol regulatory element binding protein cleavage-activating protein (SCAP) inhibitors |
| TW202128676A (zh) * | 2019-11-13 | 2021-08-01 | 美商卡普勒斯療法有限責任公司 | 具有環醯胺的噻吩化合物及其用途 |
| AU2020381462A1 (en) * | 2019-11-13 | 2022-06-02 | Capulus Therapeutics, Llc | SREBP inhibitor comprising a thiophene central ring |
| WO2021154735A1 (en) * | 2020-01-27 | 2021-08-05 | Capulus Therapeutics, Llc | Srebp inhibitors comprising a thiophene central ring |
| EP4185584A1 (en) * | 2020-07-24 | 2023-05-31 | Capulus Therapeutics, LLC | Srebp inhibitors comprising a thiophene central ring |
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| IL96891A0 (en) | 1990-01-17 | 1992-03-29 | Merck Sharp & Dohme | Indole-substituted five-membered heteroaromatic compounds,their preparation and pharmaceutical compositions containing them |
| 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 |
| ATE223408T1 (de) | 1998-02-09 | 2002-09-15 | Dimensional Pharm Inc | Heteroaryl-amidinen,-methylamidinen und - guanidinen als protease inhibitoren, insbesondere als urokinase inhibitoren |
| IL149872A0 (en) | 1999-12-16 | 2002-11-10 | Schering Corp | Substituted imidazole neuropeptide y y5 receptor antagonists |
| AR029686A1 (es) | 2000-06-22 | 2003-07-10 | Dow Agrosciences Llc | Compuestos de 2-(3,5-disustituido-4-piridil)-4-(tienilo, tiazolilo o arilfenil)-1,3-oxazolina, composiciones y metodos para el control de insectos o acaros y/o plantas utilizando dichos compuestos |
| 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 |
| JP2008545788A (ja) | 2005-06-09 | 2008-12-18 | シェーリング−プラウ・リミテッド | Ｎ−［（フェニルオキシ）フェニル］−１，１，１−トリフルオロメタンスルホンアミドおよびｎ−［（フェニルスルファニル）フェニル）］−１，１，１−トリフルオロメタンスルホンアミド誘導体による動物中の寄生生物の制御 |
| DK1907382T3 (en) | 2005-07-26 | 2015-08-31 | Bial Portela & Ca Sa | Nitrocatecholderivater comt inhibitors as |
| US7615569B2 (en) | 2005-08-16 | 2009-11-10 | Icagen, Inc. | Inhibitors of ion 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 |
| AU2008214095B2 (en) * | 2007-02-02 | 2014-07-10 | 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 |
| AU2008227979B2 (en) | 2007-03-16 | 2014-02-06 | Actelion Pharmaceuticals Ltd | Amino- pyridine derivatives as S1P1 /EDG1 receptor agonists |
| CA2710345C (en) | 2007-12-21 | 2016-11-15 | Merck Serono S.A. | Triazole oxadiazoles derivatives |
| US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
| CA2786424A1 (en) | 2010-01-08 | 2011-07-14 | Ruga Corporation | 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 |
| TW201332989A (zh) | 2011-12-23 | 2013-08-16 | Millennium Pharm Inc | 雜芳基化合物及其用途 |
| US20140364460A1 (en) | 2012-01-18 | 2014-12-11 | 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 |
| EP3038622B1 (en) | 2013-08-28 | 2018-05-30 | Medivation Technologies LLC | Heterocyclic compounds and methods of use |
| EP3265457A1 (en) | 2015-03-04 | 2018-01-10 | Medivation Technologies LLC | Sterol regulatory element-binding proteins (srebps) inhibitors |
-
2016
- 2016-03-03 CA CA2978627A patent/CA2978627A1/en not_active Abandoned
- 2016-03-03 EP EP16716719.6A patent/EP3265088A1/en not_active Withdrawn
- 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 WO PCT/US2016/020644 patent/WO2016141159A1/en not_active Ceased
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