CA2978627A1

CA2978627A1 - Srebp blockers for use in treating liver fibrosis, elevated cholesterol and insulin resistance

Srebp blockers for use in treating liver fibrosis, elevated cholesterol and insulin resistance Download PDF

Info

Publication number: CA2978627A1
Authority: CA; Canada
Prior art keywords: thiazol; phenyl; trifluoromethanesulfonamide; chloro; linear
Prior art date: 2015-03-04
Legal status : Abandoned

Application number

CA2978627A

Other languages

English (en)

French (fr)

Inventor

Sebastian Bernales

Jeffrey Lindquist

Mausumee Guha

Current Assignee

Medivation Technologies LLC

Original Assignee

Medivation Technologies LLC

Priority date

2015-03-04

Filing date

2016-03-03

Publication date

2016-09-09

2016-03-03 Application filed by Medivation Technologies LLC filed Critical Medivation Technologies LLC

2016-09-09 Publication of CA2978627A1 publication Critical patent/CA2978627A1/en

Status Abandoned legal-status Critical Current

Links

208000019425 cirrhosis of liver Diseases 0.000 title claims abstract description 35
208000001072 type 2 diabetes mellitus Diseases 0.000 title claims abstract description 35
206010022489 Insulin Resistance Diseases 0.000 title claims abstract description 33
206010014476 Elevated cholesterol Diseases 0.000 title claims abstract description 23
208000035150 Hypercholesterolemia Diseases 0.000 title claims abstract description 23
150000001875 compounds Chemical class 0.000 claims abstract description 402
208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims abstract description 53
238000000034 method Methods 0.000 claims abstract description 52
206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims abstract description 43
229910052739 hydrogen Inorganic materials 0.000 claims description 90
125000005843 halogen group Chemical group 0.000 claims description 89
239000001257 hydrogen Substances 0.000 claims description 87
125000000217 alkyl group Chemical group 0.000 claims description 84
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 82
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 65
150000003839 salts Chemical class 0.000 claims description 58
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 54
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 47
150000002431 hydrogen Chemical class 0.000 claims description 47
229910052736 halogen Inorganic materials 0.000 claims description 46
150000002367 halogens Chemical group 0.000 claims description 44
125000000392 cycloalkenyl group Chemical group 0.000 claims description 41
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
125000003118 aryl group Chemical group 0.000 claims description 35
-1 4- [2-(2-tert-butylpyridin-4-yl)- 1,3 -thiazol -4-yl] -3 -chlorophenyl Chemical group 0.000 claims description 29
125000003342 alkenyl group Chemical group 0.000 claims description 29
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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
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 20
125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims description 18
125000000304 alkynyl group Chemical group 0.000 claims description 17
208000035475 disorder Diseases 0.000 claims description 17
125000000623 heterocyclic group Chemical group 0.000 claims description 17
239000003814 drug Substances 0.000 claims description 14
229910052717 sulfur Inorganic materials 0.000 claims description 14
XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
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
SXCHDDWMFBETRA-UHFFFAOYSA-N oxazinan-3-one Chemical compound O=C1CCCON1 SXCHDDWMFBETRA-UHFFFAOYSA-N 0.000 claims description 12
229910052760 oxygen Inorganic materials 0.000 claims description 12
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 12
125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 10
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
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 7
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 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
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
KWXNXSCLFKXCEZ-UHFFFAOYSA-N COc1cc(ccc1NS(=O)(=O)C(F)(F)F)-c1csc(n1)-c1ccnc(CC(C)(C)C)c1 Chemical compound COc1cc(ccc1NS(=O)(=O)C(F)(F)F)-c1csc(n1)-c1ccnc(CC(C)(C)C)c1 KWXNXSCLFKXCEZ-UHFFFAOYSA-N 0.000 claims description 4
125000001495 ethyl group Chemical group [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
125000004108 n-butyl group Chemical group [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
YKMDGHUTQJXGEZ-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1cccc(NS(=O)(=O)C(F)(F)F)c1 Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1cccc(NS(=O)(=O)C(F)(F)F)c1 YKMDGHUTQJXGEZ-UHFFFAOYSA-N 0.000 claims description 3
IDUBYTNNGQVFKK-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1F Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1F IDUBYTNNGQVFKK-UHFFFAOYSA-N 0.000 claims description 3
ZRADFIFIKXLRKS-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1)N(C)S(=O)(=O)C(F)(F)F Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1)N(C)S(=O)(=O)C(F)(F)F ZRADFIFIKXLRKS-UHFFFAOYSA-N 0.000 claims description 3
PLJGAHOSSCDPNJ-UHFFFAOYSA-N CCCc1ccnc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 Chemical compound CCCc1ccnc(c1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 PLJGAHOSSCDPNJ-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
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
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 3
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 8
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 8
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 8
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 8
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 7
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 6
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 6
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 5
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 5
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 5
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 4
ONOAWJARGDBBHQ-UHFFFAOYSA-N CC(C)CCn1nccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CC(C)CCn1nccc1-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl ONOAWJARGDBBHQ-UHFFFAOYSA-N 0.000 claims 4
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 4
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 4
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 4
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 4
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 4
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 4
OBXAVNFSPXSGEI-UHFFFAOYSA-N FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccc3OCCc3c2)c(Cl)c1 Chemical compound FC(F)(F)S(=O)(=O)Nc1ccc(-c2csc(n2)-c2ccc3OCCc3c2)c(Cl)c1 OBXAVNFSPXSGEI-UHFFFAOYSA-N 0.000 claims 4
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 4
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 4
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 4
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 4
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 4
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 4
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 4
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 4
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 4
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 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 4
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 4
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 4
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 4
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 3
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 3
HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 claims 3
AIEAPNQMTZOCCM-UHFFFAOYSA-N CC(=O)OCCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F Chemical compound CC(=O)OCCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F AIEAPNQMTZOCCM-UHFFFAOYSA-N 0.000 claims 2
FGKMAVOOCYQELS-UHFFFAOYSA-N CC(=O)OCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F Chemical compound CC(=O)OCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F FGKMAVOOCYQELS-UHFFFAOYSA-N 0.000 claims 2
YLDOXGOXQFRYAF-UHFFFAOYSA-N CC(=O)OCOCCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F Chemical compound CC(=O)OCOCCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F YLDOXGOXQFRYAF-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
HBBQEINCHIYDDJ-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(N(CCO)S(=O)(=O)C(F)(F)F)c(Br)c1Cl Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(N(CCO)S(=O)(=O)C(F)(F)F)c(Br)c1Cl HBBQEINCHIYDDJ-UHFFFAOYSA-N 0.000 claims 2
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 2
DJVVWPCQFYBSAP-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCCC1=O)S(=O)(=O)C(F)(F)F Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCCC1=O)S(=O)(=O)C(F)(F)F DJVVWPCQFYBSAP-UHFFFAOYSA-N 0.000 claims 2
JZZUBFXUHGLHBP-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCNC1=O)S(=O)(=O)C(F)(F)F Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCNC1=O)S(=O)(=O)C(F)(F)F JZZUBFXUHGLHBP-UHFFFAOYSA-N 0.000 claims 2
NGEZWAKFMJYUHZ-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCOC1=O)S(=O)(=O)C(F)(F)F Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCOC1=O)S(=O)(=O)C(F)(F)F NGEZWAKFMJYUHZ-UHFFFAOYSA-N 0.000 claims 2
AWWGJQMYVLAKIV-UHFFFAOYSA-N CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCO)S(=O)(=O)C(F)(F)F Chemical compound CC(C)(C)c1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCO)S(=O)(=O)C(F)(F)F AWWGJQMYVLAKIV-UHFFFAOYSA-N 0.000 claims 2
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
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 2
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 2
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 2
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 2
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 2
XTNWADYVDXISSE-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(C)c1 Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(C)c1 XTNWADYVDXISSE-UHFFFAOYSA-N 0.000 claims 2
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 2
YQQDCIDIMOQSMW-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C(C)C Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C(C)C YQQDCIDIMOQSMW-UHFFFAOYSA-N 0.000 claims 2
YPWJPLPMADNSTO-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)c(c1)C(F)(F)F YPWJPLPMADNSTO-UHFFFAOYSA-N 0.000 claims 2
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 2
SXBVEESEOHSJSZ-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1C(F)(F)F SXBVEESEOHSJSZ-UHFFFAOYSA-N 0.000 claims 2
ILCXFUAMBOSJGF-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(C(C)OC(=O)C(C)C)S(=O)(=O)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(C(C)OC(=O)C(C)C)S(=O)(=O)C(F)(F)F ILCXFUAMBOSJGF-UHFFFAOYSA-N 0.000 claims 2
BCZBMGDLWFUOGG-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN(C)C)S(=O)(=O)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN(C)C)S(=O)(=O)C(F)(F)F BCZBMGDLWFUOGG-UHFFFAOYSA-N 0.000 claims 2
MEZHISCIBQYWPA-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCCC1)S(=O)(=O)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCCC1)S(=O)(=O)C(F)(F)F MEZHISCIBQYWPA-UHFFFAOYSA-N 0.000 claims 2
DUMUKNRVZNWNIN-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCOC1=O)S(=O)(=O)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCN1CCOC1=O)S(=O)(=O)C(F)(F)F DUMUKNRVZNWNIN-UHFFFAOYSA-N 0.000 claims 2
WEPJYYOPYGPYQX-UHFFFAOYSA-N CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCO)S(=O)(=O)C(F)(F)F Chemical compound CC(C)Cc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(CCO)S(=O)(=O)C(F)(F)F WEPJYYOPYGPYQX-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
GUVRJKSXMOWGHQ-UHFFFAOYSA-N CCCCN(CCCC)c1cc(nc(CC(C)C)n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCCN(CCCC)c1cc(nc(CC(C)C)n1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl GUVRJKSXMOWGHQ-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 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 claims 2
ZSKFEUDYEGGNNO-UHFFFAOYSA-N CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(C(=O)C=C)S(=O)(=O)C(F)(F)F Chemical compound CCCc1cc(ccn1)-c1nc(cs1)-c1ccc(cc1Cl)N(C(=O)C=C)S(=O)(=O)C(F)(F)F ZSKFEUDYEGGNNO-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
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 2
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 2
VWBUQNYZHJHJHJ-UHFFFAOYSA-N CCCn1ccc2c(ccnc12)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl Chemical compound CCCn1ccc2c(ccnc12)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1Cl VWBUQNYZHJHJHJ-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
RFAFCABBMPGCGA-UHFFFAOYSA-N COC(=O)N(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F Chemical compound COC(=O)N(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F RFAFCABBMPGCGA-UHFFFAOYSA-N 0.000 claims 2
VAXSNAWCQBUHSL-UHFFFAOYSA-N COCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F Chemical compound COCN(c1ccc(-c2csc(n2)-c2ccnc(c2)C(C)(C)C)c(Cl)c1)S(=O)(=O)C(F)(F)F VAXSNAWCQBUHSL-UHFFFAOYSA-N 0.000 claims 2
GGDACAHRWOMZBY-UHFFFAOYSA-N COCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1.CCCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 Chemical compound COCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1.CCCCc1cc(ccn1)-c1nc(cs1)-c1ccc(NS(=O)(=O)C(F)(F)F)cc1 GGDACAHRWOMZBY-UHFFFAOYSA-N 0.000 claims 2
YVDQEFUHDSGIHH-UHFFFAOYSA-N COc1cc(NS(=O)(=O)C(F)(F)F)ccc1-c1csc(n1)-c1ccnc(CC(C)C)c1 Chemical compound COc1cc(NS(=O)(=O)C(F)(F)F)ccc1-c1csc(n1)-c1ccnc(CC(C)C)c1 YVDQEFUHDSGIHH-UHFFFAOYSA-N 0.000 claims 2
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