AU2007223797A1 - Substituted aminothiazole derivatives with anti-HCV activity - Google Patents

Info

Publication number

AU2007223797A1

AU2007223797A1 AU2007223797A AU2007223797A AU2007223797A1 AU 2007223797 A1 AU2007223797 A1 AU 2007223797A1 AU 2007223797 A AU2007223797 A AU 2007223797A AU 2007223797 A AU2007223797 A AU 2007223797A AU 2007223797 A1 AU2007223797 A1 AU 2007223797A1

Authority

AU

Australia

Prior art keywords

phenyl

thiazol

trifluoromethyl

amino

alkyl

Prior art date

2006-03-08

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.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 230000000694 effects Effects 0.000 title description 24
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical class NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims description 263
• 125000000217 alkyl group Chemical group 0.000 claims description 121
• 150000003839 salts Chemical class 0.000 claims description 79
• 229910052736 halogen Inorganic materials 0.000 claims description 78
• -1 n-octyl Chemical group 0.000 claims description 78
• 150000002367 halogens Chemical class 0.000 claims description 75
• 125000001424 substituent group Chemical group 0.000 claims description 73
• 238000000034 method Methods 0.000 claims description 71
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 70
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 70
• 125000003545 alkoxy group Chemical group 0.000 claims description 60
• 239000000203 mixture Substances 0.000 claims description 59
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 49
• 125000001188 haloalkyl group Chemical group 0.000 claims description 34
• 125000004432 carbon atom Chemical group C* 0.000 claims description 29
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 29
• 239000001257 hydrogen Substances 0.000 claims description 27
• 229910052739 hydrogen Inorganic materials 0.000 claims description 27
• 208000005176 Hepatitis C Diseases 0.000 claims description 26
• 238000011282 treatment Methods 0.000 claims description 26
• 125000003282 alkyl amino group Chemical group 0.000 claims description 25
• 125000003118 aryl group Chemical group 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
• 239000008194 pharmaceutical composition Substances 0.000 claims description 23
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 22
• 230000010076 replication Effects 0.000 claims description 22
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 18
• 125000004043 oxo group Chemical group O=* 0.000 claims description 18
• 230000002401 inhibitory effect Effects 0.000 claims description 16
• 229910052799 carbon Inorganic materials 0.000 claims description 15
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 15
• 208000015181 infectious disease Diseases 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 14
• 125000000623 heterocyclic group Chemical group 0.000 claims description 14
• 229940079322 interferon Drugs 0.000 claims description 14
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
• 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 13
• 102000014150 Interferons Human genes 0.000 claims description 13
• 108010050904 Interferons Proteins 0.000 claims description 13
• 239000002775 capsule Substances 0.000 claims description 13
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
• 208000010710 hepatitis C virus infection Diseases 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 229910052757 nitrogen Inorganic materials 0.000 claims description 11
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical group N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 claims description 9
• 210000004369 blood Anatomy 0.000 claims description 9
• 239000008280 blood Substances 0.000 claims description 9
• 125000001153 fluoro group Chemical group F* 0.000 claims description 9
• 125000002883 imidazolyl group Chemical group 0.000 claims description 9
• 125000004076 pyridyl group Chemical group 0.000 claims description 9
• 125000001544 thienyl group Chemical group 0.000 claims description 9
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 8
• 239000002253 acid Substances 0.000 claims description 8
• 101150068479 chrb gene Proteins 0.000 claims description 8
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
• 229920003171 Poly (ethylene oxide) Polymers 0.000 claims description 7
• 125000005907 alkyl ester group Chemical group 0.000 claims description 7
• 238000001727 in vivo Methods 0.000 claims description 7
• 210000002966 serum Anatomy 0.000 claims description 7
• TVRCRTJYMVTEFS-ICGCPXGVSA-N [(2r,3r,4r,5r)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)-4-methyloxolan-3-yl] (2s)-2-amino-3-methylbutanoate Chemical compound C[C@@]1(O)[C@H](OC(=O)[C@@H](N)C(C)C)[C@@H](CO)O[C@H]1N1C(=O)N=C(N)C=C1 TVRCRTJYMVTEFS-ICGCPXGVSA-N 0.000 claims description 6
• 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 239000006188 syrup Substances 0.000 claims description 6
• 235000020357 syrup Nutrition 0.000 claims description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 5
• 125000005431 alkyl carboxamide group Chemical group 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 229960000329 ribavirin Drugs 0.000 claims description 5
• BBAWEDCPNXPBQM-GDEBMMAJSA-N telaprevir Chemical compound N([C@H](C(=O)N[C@H](C(=O)N1C[C@@H]2CCC[C@@H]2[C@H]1C(=O)N[C@@H](CCC)C(=O)C(=O)NC1CC1)C(C)(C)C)C1CCCCC1)C(=O)C1=CN=CC=N1 BBAWEDCPNXPBQM-GDEBMMAJSA-N 0.000 claims description 5
• 229950002810 valopicitabine Drugs 0.000 claims description 5
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 4
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 4
• 229910019142 PO4 Inorganic materials 0.000 claims description 4
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• 238000000338 in vitro Methods 0.000 claims description 4
• 125000002971 oxazolyl group Chemical group 0.000 claims description 4
• 239000006187 pill Substances 0.000 claims description 4
• 229960002935 telaprevir Drugs 0.000 claims description 4
• 108010017101 telaprevir Proteins 0.000 claims description 4
• 125000000335 thiazolyl group Chemical group 0.000 claims description 4
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• 229940054534 ophthalmic solution Drugs 0.000 claims description 3
• 239000002997 ophthalmic solution Substances 0.000 claims description 3
• 239000010452 phosphate Substances 0.000 claims description 3
• GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 claims description 2
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
• 239000000443 aerosol Substances 0.000 claims description 2
• 239000006071 cream Substances 0.000 claims description 2
• 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 239000004202 carbamide Substances 0.000 claims 21
• 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 14
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 9
• UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 claims 4
• COYUWWHXFFZSAH-UHFFFAOYSA-N 1-[4-[methyl(pentyl)amino]-3-(trifluoromethyl)phenyl]-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 COYUWWHXFFZSAH-UHFFFAOYSA-N 0.000 claims 3
• LKYNGTHMKCTTQC-UHFFFAOYSA-N 1,2-oxazole-3-carboxamide Chemical compound NC(=O)C=1C=CON=1 LKYNGTHMKCTTQC-UHFFFAOYSA-N 0.000 claims 2
• 239000003443 antiviral agent Substances 0.000 claims 2
• LWJYKQGCEJMOML-UHFFFAOYSA-N methyl 2-[4-[methyl(pentyl)amino]-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-2-oxoacetate Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 LWJYKQGCEJMOML-UHFFFAOYSA-N 0.000 claims 2
• SRDHVNLUJWGSQV-UHFFFAOYSA-N 1-(3-fluoro-4-pentoxyphenyl)-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 SRDHVNLUJWGSQV-UHFFFAOYSA-N 0.000 claims 1
• KGLWABYMDPSEFP-UHFFFAOYSA-N 1-(3-fluoro-4-pentoxyphenyl)-1-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=CC(F)=CC=2)=CS1 KGLWABYMDPSEFP-UHFFFAOYSA-N 0.000 claims 1
• LSQGZKVSOGEIHG-UHFFFAOYSA-N 1-(4-hexoxyphenyl)-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 LSQGZKVSOGEIHG-UHFFFAOYSA-N 0.000 claims 1
• ZEHPMRGPAJPVOZ-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 ZEHPMRGPAJPVOZ-UHFFFAOYSA-N 0.000 claims 1
• OFLWYLCWNONOIJ-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 OFLWYLCWNONOIJ-UHFFFAOYSA-N 0.000 claims 1
• LDHSVIOWFASFMS-UHFFFAOYSA-N 1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]-1-[4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=NC(C)=CC=2)=CS1 LDHSVIOWFASFMS-UHFFFAOYSA-N 0.000 claims 1
• XNPZBGSSIYIMMD-UHFFFAOYSA-N 1-[4-(2-methylpyridin-3-yl)-1,3-thiazol-2-yl]-1-[4-pentoxy-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C(=NC=CC=2)C)=CS1 XNPZBGSSIYIMMD-UHFFFAOYSA-N 0.000 claims 1
• ZGTWRYRRURKLRW-UHFFFAOYSA-N 1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-1-(4-hexoxyphenyl)urea Chemical compound C1=CC(OCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 ZGTWRYRRURKLRW-UHFFFAOYSA-N 0.000 claims 1
• PDNPOROPMBQFNT-UHFFFAOYSA-N 1-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-1-[4-(2-methylpropoxy)-3-(trifluoromethyl)phenyl]urea Chemical compound C1=C(C(F)(F)F)C(OCC(C)C)=CC=C1N(C(N)=O)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 PDNPOROPMBQFNT-UHFFFAOYSA-N 0.000 claims 1
• BQLUUHGCSLGJCN-UHFFFAOYSA-N 1-[4-butoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-2-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCC)=CC=C1N(C(N)=O)C1=NC(C=2N=CC=CC=2)=CS1 BQLUUHGCSLGJCN-UHFFFAOYSA-N 0.000 claims 1
• JBSIOXNVUHMPJS-UHFFFAOYSA-N 1-[4-fluoro-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C=1C=C(F)C(C(F)(F)F)=CC=1N(C(=O)N)C(SC=1)=NC=1C1=CC=CN=C1 JBSIOXNVUHMPJS-UHFFFAOYSA-N 0.000 claims 1
• YZZMVGKBKZIRPR-UHFFFAOYSA-N 1-[4-methoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 YZZMVGKBKZIRPR-UHFFFAOYSA-N 0.000 claims 1
• XTNDGPMOYHENMO-UHFFFAOYSA-N 1-[4-octoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 XTNDGPMOYHENMO-UHFFFAOYSA-N 0.000 claims 1
• NDWXDDSCFMMNAH-UHFFFAOYSA-N 1-[4-pentoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(N)=O)C1=NC(C=2C=NC=CC=2)=CS1 NDWXDDSCFMMNAH-UHFFFAOYSA-N 0.000 claims 1
• VUAXHMVRKOTJKP-UHFFFAOYSA-M 2,2-dimethylbutanoate Chemical compound CCC(C)(C)C([O-])=O VUAXHMVRKOTJKP-UHFFFAOYSA-M 0.000 claims 1
• BOXDDGNBYWTARE-UHFFFAOYSA-N 2-methyl-n-[4-pentoxy-3-(trifluoromethyl)phenyl]-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)propanamide Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)C(C)C)C1=NC(C=2C=NC=CC=2)=CS1 BOXDDGNBYWTARE-UHFFFAOYSA-N 0.000 claims 1
• GUPGZURVZDIQPM-UHFFFAOYSA-N 2-oxoethyl acetate Chemical compound CC(=O)OCC=O GUPGZURVZDIQPM-UHFFFAOYSA-N 0.000 claims 1
• ZMCNRRNKEMQNMD-UHFFFAOYSA-N 3-ethyl-1-[4-pentoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)NCC)C1=NC(C=2C=NC=CC=2)=CS1 ZMCNRRNKEMQNMD-UHFFFAOYSA-N 0.000 claims 1
• OAKURXIZZOAYBC-UHFFFAOYSA-M 3-oxopropanoate Chemical compound [O-]C(=O)CC=O OAKURXIZZOAYBC-UHFFFAOYSA-M 0.000 claims 1
• ZIMUFHZVVIRLPQ-UHFFFAOYSA-N 3-tert-butyl-1-[4-pentoxy-3-(trifluoromethyl)phenyl]-1-(4-pyridin-3-yl-1,3-thiazol-2-yl)urea Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)NC(C)(C)C)C1=NC(C=2C=NC=CC=2)=CS1 ZIMUFHZVVIRLPQ-UHFFFAOYSA-N 0.000 claims 1
• HFDITUDABQZIRP-UHFFFAOYSA-N 4-[n-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-4-(4-thiophen-2-ylbutoxy)-3-(trifluoromethyl)anilino]-4-oxobutanoic acid Chemical compound C=1C=C(OCCCCC=2SC=CC=2)C(C(F)(F)F)=CC=1N(C(=O)CCC(=O)O)C(SC=1F)=NC=1C1=CC=CN=C1 HFDITUDABQZIRP-UHFFFAOYSA-N 0.000 claims 1
• IVHJSPXCFPRYPD-UHFFFAOYSA-N 5-methyl-n-[4-[methyl(pentyl)amino]-3-(trifluoromethyl)phenyl]-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-1,2-oxazole-3-carboxamide Chemical compound C1=C(C(F)(F)F)C(N(C)CCCCC)=CC=C1N(C=1SC=C(N=1)C=1C=NC=CC=1)C(=O)C1=NOC(C)=C1 IVHJSPXCFPRYPD-UHFFFAOYSA-N 0.000 claims 1
• 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 claims 1
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
• PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
• GYPUOUQFOYKIRN-UHFFFAOYSA-N [1-(n-[4-(6-methylpyridin-3-yl)-1,3-thiazol-2-yl]-4-octoxyanilino)-1-oxopropan-2-yl] acetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(C)OC(C)=O)C1=NC(C=2C=NC(C)=CC=2)=CS1 GYPUOUQFOYKIRN-UHFFFAOYSA-N 0.000 claims 1
• XTLRLNTVLMXJQW-UHFFFAOYSA-N [1-oxo-1-[4-pentoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]propan-2-yl] acetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C(=O)C(C)OC(C)=O)C1=NC(C=2C=NC=CC=2)=CS1 XTLRLNTVLMXJQW-UHFFFAOYSA-N 0.000 claims 1
• FLPKMSLEFQUPAA-UHFFFAOYSA-N [2-oxo-2-[4-pentoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)-3-(trifluoromethyl)anilino]-1-phenylethyl] acetate Chemical compound C1=C(C(F)(F)F)C(OCCCCC)=CC=C1N(C=1SC=C(N=1)C=1C=NC=CC=1)C(=O)C(OC(C)=O)C1=CC=CC=C1 FLPKMSLEFQUPAA-UHFFFAOYSA-N 0.000 claims 1
• PJARSAMACCMQNY-UHFFFAOYSA-N [4-[n-(5-fluoro-4-pyridin-3-yl-1,3-thiazol-2-yl)-4-octyl-3-(trifluoromethyl)anilino]-4-oxobutyl] dihydrogen phosphate Chemical compound C1=C(C(F)(F)F)C(CCCCCCCC)=CC=C1N(C(=O)CCCOP(O)(O)=O)C1=NC(C=2C=NC=CC=2)=C(F)S1 PJARSAMACCMQNY-UHFFFAOYSA-N 0.000 claims 1
• DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims 1
• RHJVIGLEIFVHIJ-UHFFFAOYSA-N cyclohexanecarboxamide Chemical compound NC(=O)C1[CH]CCCC1 RHJVIGLEIFVHIJ-UHFFFAOYSA-N 0.000 claims 1
• AIMMVWOEOZMVMS-UHFFFAOYSA-N cyclopropanecarboxamide Chemical compound NC(=O)C1CC1 AIMMVWOEOZMVMS-UHFFFAOYSA-N 0.000 claims 1
• FGWPGLBHOOXQNV-UHFFFAOYSA-N ethyl 2-(4-octoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(=O)OCC)C1=NC(C=2C=NC=CC=2)=CS1 FGWPGLBHOOXQNV-UHFFFAOYSA-N 0.000 claims 1
• 239000012530 fluid Substances 0.000 claims 1
• HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims 1
• GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims 1
• WYWGTENDABLBKZ-UHFFFAOYSA-N methyl 2-(3-fluoro-n-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]-4-pentoxyanilino)-2-oxoacetate Chemical compound C1=C(F)C(OCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=CC(F)=CC=2)=CS1 WYWGTENDABLBKZ-UHFFFAOYSA-N 0.000 claims 1
• ZELXVXHSONGIOI-UHFFFAOYSA-N methyl 2-(4-heptoxy-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 ZELXVXHSONGIOI-UHFFFAOYSA-N 0.000 claims 1
• UVESKLHONKPZRP-UHFFFAOYSA-N methyl 2-(4-octyl-n-(4-pyridin-3-yl-1,3-thiazol-2-yl)anilino)-2-oxoacetate Chemical compound C1=CC(CCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=NC=CC=2)=CS1 UVESKLHONKPZRP-UHFFFAOYSA-N 0.000 claims 1
• NSUVGYQHAWCHFW-UHFFFAOYSA-N methyl 2-(n-[4-(3,4-difluorophenyl)-1,3-thiazol-2-yl]-4-octoxyanilino)-2-oxoacetate Chemical compound C1=CC(OCCCCCCCC)=CC=C1N(C(=O)C(=O)OC)C1=NC(C=2C=C(F)C(F)=CC=2)=CS1 NSUVGYQHAWCHFW-UHFFFAOYSA-N 0.000 claims 1
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