HRP20010633A2 - Oxamic acids and derivatives as thyroid receptor ligands - Google Patents
Oxamic acids and derivatives as thyroid receptor ligands Download PDFInfo
- Publication number
- HRP20010633A2 HRP20010633A2 HR20010633A HRP20010633A HRP20010633A2 HR P20010633 A2 HRP20010633 A2 HR P20010633A2 HR 20010633 A HR20010633 A HR 20010633A HR P20010633 A HRP20010633 A HR P20010633A HR P20010633 A2 HRP20010633 A2 HR P20010633A2
- Authority
- HR
- Croatia
- Prior art keywords
- hydroxy
- phenyl
- phenoxy
- oxamic acid
- methyl
- Prior art date
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- SOWBFZRMHSNYGE-UHFFFAOYSA-N oxamic acid Chemical class NC(=O)C(O)=O SOWBFZRMHSNYGE-UHFFFAOYSA-N 0.000 title description 50
- 102000004217 thyroid hormone receptors Human genes 0.000 title description 4
- 108090000721 thyroid hormone receptors Proteins 0.000 title description 4
- 239000003446 ligand Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 349
- -1 -NR13R14 Chemical group 0.000 claims description 216
- 150000003839 salts Chemical class 0.000 claims description 197
- 125000004494 ethyl ester group Chemical group 0.000 claims description 146
- 229940079593 drug Drugs 0.000 claims description 106
- 239000003814 drug Substances 0.000 claims description 106
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 66
- 239000001257 hydrogen Substances 0.000 claims description 59
- 229910052739 hydrogen Inorganic materials 0.000 claims description 59
- 238000000034 method Methods 0.000 claims description 53
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 230000003287 optical effect Effects 0.000 claims description 32
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 29
- 239000003085 diluting agent Substances 0.000 claims description 27
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000002837 carbocyclic group Chemical group 0.000 claims description 26
- 208000008589 Obesity Diseases 0.000 claims description 25
- 230000000578 anorexic effect Effects 0.000 claims description 25
- 206010061428 decreased appetite Diseases 0.000 claims description 25
- 235000020824 obesity Nutrition 0.000 claims description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 24
- 241000124008 Mammalia Species 0.000 claims description 24
- 239000000460 chlorine Substances 0.000 claims description 23
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- 125000001424 substituent group Chemical group 0.000 claims description 23
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
- 229910052760 oxygen Inorganic materials 0.000 claims description 21
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229940086609 Lipase inhibitor Drugs 0.000 claims description 18
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 150000002367 halogens Chemical class 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 16
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 125000004043 oxo group Chemical group O=* 0.000 claims description 14
- 201000001320 Atherosclerosis Diseases 0.000 claims description 13
- 208000024799 Thyroid disease Diseases 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 11
- 208000010412 Glaucoma Diseases 0.000 claims description 11
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 11
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 11
- 206010020772 Hypertension Diseases 0.000 claims description 11
- 208000001132 Osteoporosis Diseases 0.000 claims description 11
- 206010003119 arrhythmia Diseases 0.000 claims description 11
- 208000029078 coronary artery disease Diseases 0.000 claims description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 206010012601 diabetes mellitus Diseases 0.000 claims description 11
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 11
- 208000003532 hypothyroidism Diseases 0.000 claims description 11
- 230000002989 hypothyroidism Effects 0.000 claims description 11
- 208000017520 skin disease Diseases 0.000 claims description 11
- 208000021510 thyroid gland disease Diseases 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 9
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
- 125000001475 halogen functional group Chemical group 0.000 claims description 8
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 8
- 239000011734 sodium Substances 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
- 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 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 125000004340 exo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@]2([H])* 0.000 claims description 5
- 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 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- ZVSVBNRMEPNQOM-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound ClC1=CC(NC(=O)C(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 ZVSVBNRMEPNQOM-UHFFFAOYSA-N 0.000 claims description 4
- NOSHQXUEOURLQH-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-(cyclopropylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound ClC1=CC(NC(=O)C(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CC2)=C1 NOSHQXUEOURLQH-UHFFFAOYSA-N 0.000 claims description 4
- FVIHQODUVAAWNZ-UHFFFAOYSA-N 2-[3-chloro-4-[3-(cyclopropylsulfamoyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CC2)=C1 FVIHQODUVAAWNZ-UHFFFAOYSA-N 0.000 claims description 4
- SCWOTKBDFCXIBK-UHFFFAOYSA-N 2-[3-chloro-4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound C=1C(OC=2C(=CC(NC(=O)C(O)=O)=CC=2C)Cl)=CC=C(O)C=1C(=O)N(C)C1CCC1 SCWOTKBDFCXIBK-UHFFFAOYSA-N 0.000 claims description 4
- CEYPDXWCYTVSDN-UHFFFAOYSA-N 2-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C2=C1CCC2 CEYPDXWCYTVSDN-UHFFFAOYSA-N 0.000 claims description 4
- RJOYUZQXACUPTO-UHFFFAOYSA-N 2-[4-[3-(cyclopropylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CC2)=C1 RJOYUZQXACUPTO-UHFFFAOYSA-N 0.000 claims description 4
- RIEZHBBXHWUJQC-UHFFFAOYSA-N 2-[4-[3-(cyclopropylsulfamoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CC2)=C1 RIEZHBBXHWUJQC-UHFFFAOYSA-N 0.000 claims description 4
- 229940127470 Lipase Inhibitors Drugs 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
- GJIODCAGQJCGQL-UHFFFAOYSA-N 2-[3,5-dichloro-4-(3-cyclopentylsulfonyl-4-hydroxyphenoxy)anilino]-2-oxoacetic acid Chemical compound ClC1=CC(NC(=O)C(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C2CCCC2)=C1 GJIODCAGQJCGQL-UHFFFAOYSA-N 0.000 claims description 3
- QRPDMRMLNSKBMP-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-(cyclohexylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound ClC1=CC(NC(=O)C(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCCC2)=C1 QRPDMRMLNSKBMP-UHFFFAOYSA-N 0.000 claims description 3
- QMQYAGCEWQSXDM-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-(cyclopentylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound ClC1=CC(NC(=O)C(=O)O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCC2)=C1 QMQYAGCEWQSXDM-UHFFFAOYSA-N 0.000 claims description 3
- XIALDZZQMKFCMN-UHFFFAOYSA-N 2-[3-chloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 XIALDZZQMKFCMN-UHFFFAOYSA-N 0.000 claims description 3
- LMSDHGQUPBOKBQ-UHFFFAOYSA-N 2-[3-chloro-4-[3-(cyclohexylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCCC2)=C1 LMSDHGQUPBOKBQ-UHFFFAOYSA-N 0.000 claims description 3
- DJTHRVJZKVVDID-UHFFFAOYSA-N 2-[3-chloro-4-[3-(cyclopentylmethylsulfonyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCC2)=C1 DJTHRVJZKVVDID-UHFFFAOYSA-N 0.000 claims description 3
- GXWVTBYHCGFUAQ-UHFFFAOYSA-N 2-[4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 GXWVTBYHCGFUAQ-UHFFFAOYSA-N 0.000 claims description 3
- KMDTXPYKVUIYPP-UHFFFAOYSA-N 2-[4-[3-(cyclohexylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCCC2)=C1 KMDTXPYKVUIYPP-UHFFFAOYSA-N 0.000 claims description 3
- QNTJVPBEUVYXJC-UHFFFAOYSA-N 2-[4-[3-(cyclopentylmethylsulfonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCC2)=C1 QNTJVPBEUVYXJC-UHFFFAOYSA-N 0.000 claims description 3
- GJFODAFOPHZYFS-UHFFFAOYSA-N 2-[4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound C=1C(OC=2C(=CC(NC(=O)C(O)=O)=CC=2C)C)=CC=C(O)C=1C(=O)N(C)C1CCC1 GJFODAFOPHZYFS-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 3
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 2
- ZOFRNCXBRYIWKT-UHFFFAOYSA-N 2-[3,5-dichloro-4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]anilino]-2-oxoacetic acid Chemical compound C=1C(OC=2C(=CC(NC(=O)C(O)=O)=CC=2Cl)Cl)=CC=C(O)C=1C(=O)N(C)C1CCC1 ZOFRNCXBRYIWKT-UHFFFAOYSA-N 0.000 claims description 2
- LCVAHHKGGHCKGN-UHFFFAOYSA-N 2-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 LCVAHHKGGHCKGN-UHFFFAOYSA-N 0.000 claims description 2
- WAKOQTHSZOWZAC-UHFFFAOYSA-N 2-[4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetic acid Chemical compound CC1=CC(NC(=O)C(O)=O)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 WAKOQTHSZOWZAC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- 125000003542 3-methylbutan-2-yl group Chemical group [H]C([H])([H])C([H])(*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 2
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 2
- 125000004341 endo-2-norbornyl group Chemical group [H]C1([H])C([H])([H])[C@@]2([H])C([H])([H])[C@]1([H])C([H])([H])[C@@]2([H])* 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 4
- QPWPUTXGMBEWLS-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)N(C)C2CCC2)=C1 QPWPUTXGMBEWLS-UHFFFAOYSA-N 0.000 claims 1
- XOOFITZDEJABNA-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 XOOFITZDEJABNA-UHFFFAOYSA-N 0.000 claims 1
- VFVFGWCYFDEBPU-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[3-(cyclopropylsulfamoyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CC2)=C1 VFVFGWCYFDEBPU-UHFFFAOYSA-N 0.000 claims 1
- KWEVPSLORXDZCG-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(=O)N(C)C2CCC2)=C1 KWEVPSLORXDZCG-UHFFFAOYSA-N 0.000 claims 1
- ZIKMXOJEFAWJDO-UHFFFAOYSA-N ethyl 2-[4-[3-(4-fluorophenyl)sulfonyl-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(F)=CC=2)=C1 ZIKMXOJEFAWJDO-UHFFFAOYSA-N 0.000 claims 1
- UBYIHMDIEVAHSD-UHFFFAOYSA-N ethyl 2-[4-[3-[cyclobutyl(methyl)carbamoyl]-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(=O)N(C)C2CCC2)=C1 UBYIHMDIEVAHSD-UHFFFAOYSA-N 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 91
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 80
- 239000000243 solution Substances 0.000 description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 56
- 239000000203 mixture Substances 0.000 description 54
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 235000019439 ethyl acetate Nutrition 0.000 description 37
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 36
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
- 238000006243 chemical reaction Methods 0.000 description 36
- 239000007787 solid Substances 0.000 description 34
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 239000003826 tablet Substances 0.000 description 25
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- VHEULUROKHAXTB-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-(3-cyclopentylsulfonyl-4-hydroxyphenoxy)anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C2CCCC2)=C1 VHEULUROKHAXTB-UHFFFAOYSA-N 0.000 description 1
- IUOLNBLMKIOFBD-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-(3-formyl-4-hydroxyphenoxy)anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C=O)=C1 IUOLNBLMKIOFBD-UHFFFAOYSA-N 0.000 description 1
- QVIBETFRPYGZCQ-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-(4-fluoro-3-methylphenoxy)anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(F)C(C)=C1 QVIBETFRPYGZCQ-UHFFFAOYSA-N 0.000 description 1
- HZAWQAMBBNFJKC-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-(4-fluorophenoxy)anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(F)C=C1 HZAWQAMBBNFJKC-UHFFFAOYSA-N 0.000 description 1
- CZQWLMUWESMWMH-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-(4-hydroxy-3-propan-2-ylsulfonylphenoxy)anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C(C)C)=C1 CZQWLMUWESMWMH-UHFFFAOYSA-N 0.000 description 1
- QDCBZXJIOOSXNJ-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(3,3-dimethylpiperidine-1-carbonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)N2CC(C)(C)CCC2)=C1 QDCBZXJIOOSXNJ-UHFFFAOYSA-N 0.000 description 1
- BZNCHFNYYGKDGU-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(4-chlorophenoxy)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(OC=2C=CC(Cl)=CC=2)=C1 BZNCHFNYYGKDGU-UHFFFAOYSA-N 0.000 description 1
- LWJXNOIXBMHHTO-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(4-chlorophenyl)sulfonyl-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 LWJXNOIXBMHHTO-UHFFFAOYSA-N 0.000 description 1
- FRZYDHBIOHYAAK-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(4-fluorophenoxy)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(OC=2C=CC(F)=CC=2)=C1 FRZYDHBIOHYAAK-UHFFFAOYSA-N 0.000 description 1
- YZNNXRDUDSRHDW-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclobutylcarbamoyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NC2CCC2)=C1 YZNNXRDUDSRHDW-UHFFFAOYSA-N 0.000 description 1
- UYRPOZMJJYOMQF-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclobutylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCC2)=C1 UYRPOZMJJYOMQF-UHFFFAOYSA-N 0.000 description 1
- KWYHTGCETYVPIR-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclobutylsulfamoyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCC2)=C1 KWYHTGCETYVPIR-UHFFFAOYSA-N 0.000 description 1
- IUBOXQCUSWLIFL-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclohexylcarbamoyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NC2CCCCC2)=C1 IUBOXQCUSWLIFL-UHFFFAOYSA-N 0.000 description 1
- RPUNWTAUUXEADX-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclohexylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CCCCC2)=C1 RPUNWTAUUXEADX-UHFFFAOYSA-N 0.000 description 1
- HYYYNQSUOVMPKK-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclopentylcarbamoyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NC2CCCC2)=C1 HYYYNQSUOVMPKK-UHFFFAOYSA-N 0.000 description 1
- JKLBZEGYOUKZII-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclopropylcarbamoyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NC2CC2)=C1 JKLBZEGYOUKZII-UHFFFAOYSA-N 0.000 description 1
- HXRCMSRKSVUARO-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclopropylmethylcarbamoyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NCC2CC2)=C1 HXRCMSRKSVUARO-UHFFFAOYSA-N 0.000 description 1
- PJESIOPSLCNWPP-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-(cyclopropylmethylsulfonyl)-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)CC2CC2)=C1 PJESIOPSLCNWPP-UHFFFAOYSA-N 0.000 description 1
- LSPVHRWHMKCQLY-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-[(2,3-dihydro-1h-inden-1-ylamino)methyl]-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC2C3=CC=CC=C3CC2)=C1 LSPVHRWHMKCQLY-UHFFFAOYSA-N 0.000 description 1
- KJFSQKUOXLEHOB-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-[(cyclobutylamino)methyl]-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC2CCC2)=C1 KJFSQKUOXLEHOB-UHFFFAOYSA-N 0.000 description 1
- HTGYGEPOSMPKOL-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-[(cyclohexylamino)methyl]-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC2CCCCC2)=C1 HTGYGEPOSMPKOL-UHFFFAOYSA-N 0.000 description 1
- BTXZJWPDJODBNP-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-[(cyclopentylamino)methyl]-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC2CCCC2)=C1 BTXZJWPDJODBNP-UHFFFAOYSA-N 0.000 description 1
- NZUABOONLLNWRC-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[3-[(cyclopropylamino)methyl]-4-hydroxyphenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC2CC2)=C1 NZUABOONLLNWRC-UHFFFAOYSA-N 0.000 description 1
- CSKABGRDLKNOMA-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[4-hydroxy-3-(methylaminomethyl)phenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC)=C1 CSKABGRDLKNOMA-UHFFFAOYSA-N 0.000 description 1
- WYRHRYNAUYMHDI-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[4-hydroxy-3-(morpholin-4-ylmethyl)phenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CN2CCOCC2)=C1 WYRHRYNAUYMHDI-UHFFFAOYSA-N 0.000 description 1
- GAPSDNKBOBIHLH-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[4-hydroxy-3-(propan-2-ylcarbamoyl)phenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NC(C)C)=C1 GAPSDNKBOBIHLH-UHFFFAOYSA-N 0.000 description 1
- RRPMHSWCQWWVKL-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[4-hydroxy-3-(propan-2-ylsulfamoyl)phenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)NC(C)C)=C1 RRPMHSWCQWWVKL-UHFFFAOYSA-N 0.000 description 1
- JSBGLEGRRUBIND-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[4-hydroxy-3-[(1,2,3,4-tetrahydronaphthalen-1-ylamino)methyl]phenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(CNC2C3=CC=CC=C3CCC2)=C1 JSBGLEGRRUBIND-UHFFFAOYSA-N 0.000 description 1
- XAYCENBUMGDBLE-UHFFFAOYSA-N ethyl 2-[3,5-dichloro-4-[4-hydroxy-3-[(3-phenylphenyl)carbamoyl]phenoxy]anilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)NC=2C=C(C=CC=2)C=2C=CC=CC=2)=C1 XAYCENBUMGDBLE-UHFFFAOYSA-N 0.000 description 1
- KKFLGWAQFRMAFT-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[3-(cyclohexylcarbamoyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(=O)NC2CCCCC2)=C1 KKFLGWAQFRMAFT-UHFFFAOYSA-N 0.000 description 1
- WOKASGMRBMDTFH-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[3-(hexylcarbamoyl)-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetate Chemical compound C1=C(O)C(C(=O)NCCCCCC)=CC(OC=2C(=CC(NC(=O)C(=O)OCC)=CC=2C)Cl)=C1 WOKASGMRBMDTFH-UHFFFAOYSA-N 0.000 description 1
- LWHKFBFYURJYMN-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[3-[(4-fluorophenoxy)methyl]-4-hydroxyphenoxy]-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(COC=2C=CC(F)=CC=2)=C1 LWHKFBFYURJYMN-UHFFFAOYSA-N 0.000 description 1
- PZIKDESKASMPKG-UHFFFAOYSA-N ethyl 2-[3-chloro-4-[4-hydroxy-3-(phenoxymethyl)phenoxy]-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(COC=2C=CC=CC=2)=C1 PZIKDESKASMPKG-UHFFFAOYSA-N 0.000 description 1
- HGGWZAGWPCFESR-UHFFFAOYSA-N ethyl 2-[4-[(7-hydroxy-2,3-dihydro-1h-inden-4-yl)oxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C2=C1CCC2 HGGWZAGWPCFESR-UHFFFAOYSA-N 0.000 description 1
- FYWRLFOCWMQDJY-UHFFFAOYSA-N ethyl 2-[4-[3-(azepan-1-ylmethyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(CN2CCCCCC2)=C1 FYWRLFOCWMQDJY-UHFFFAOYSA-N 0.000 description 1
- LVHMDAYXCTUJBO-UHFFFAOYSA-N ethyl 2-[4-[3-(azepan-1-ylmethyl)-4-hydroxyphenoxy]-3-chloro-5-methylanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(CN2CCCCCC2)=C1 LVHMDAYXCTUJBO-UHFFFAOYSA-N 0.000 description 1
- QGYCGRHKHGWDBI-UHFFFAOYSA-N ethyl 2-[4-[3-(azepane-1-carbonyl)-4-hydroxyphenoxy]-3,5-dichloroanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(C(=O)N2CCCCCC2)=C1 QGYCGRHKHGWDBI-UHFFFAOYSA-N 0.000 description 1
- SLZPYRGXTGOQSM-UHFFFAOYSA-N ethyl 2-[4-[3-(azepane-1-carbonyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(=O)N2CCCCCC2)=C1 SLZPYRGXTGOQSM-UHFFFAOYSA-N 0.000 description 1
- RCBVGBQERWZACS-UHFFFAOYSA-N ethyl 2-[4-[3-(benzenesulfonyl)-4-hydroxyphenoxy]-3,5-dichloroanilino]-2-oxoacetate Chemical compound ClC1=CC(NC(=O)C(=O)OCC)=CC(Cl)=C1OC1=CC=C(O)C(S(=O)(=O)C=2C=CC=CC=2)=C1 RCBVGBQERWZACS-UHFFFAOYSA-N 0.000 description 1
- AMJMFLHKKRDGRK-UHFFFAOYSA-N ethyl 2-[4-[3-(butylsulfamoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound C1=C(O)C(S(=O)(=O)NCCCC)=CC(OC=2C(=CC(NC(=O)C(=O)OCC)=CC=2C)C)=C1 AMJMFLHKKRDGRK-UHFFFAOYSA-N 0.000 description 1
- HOSSJHRIBRJJKS-UHFFFAOYSA-N ethyl 2-[4-[3-(cyclobutylcarbamoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(C(=O)NC2CCC2)=C1 HOSSJHRIBRJJKS-UHFFFAOYSA-N 0.000 description 1
- UIELGKJLZBROTH-UHFFFAOYSA-N ethyl 2-[4-[3-(cyclobutylsulfamoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCC2)=C1 UIELGKJLZBROTH-UHFFFAOYSA-N 0.000 description 1
- LJTHQEXLEZKXIE-UHFFFAOYSA-N ethyl 2-[4-[3-(cyclohexylsulfamoyl)-4-hydroxyphenoxy]-3,5-dimethylanilino]-2-oxoacetate Chemical compound CC1=CC(NC(=O)C(=O)OCC)=CC(C)=C1OC1=CC=C(O)C(S(=O)(=O)NC2CCCCC2)=C1 LJTHQEXLEZKXIE-UHFFFAOYSA-N 0.000 description 1
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- SFMJNHNUOVADRW-UHFFFAOYSA-N n-[5-[9-[4-(methanesulfonamido)phenyl]-2-oxobenzo[h][1,6]naphthyridin-1-yl]-2-methylphenyl]prop-2-enamide Chemical compound C1=C(NC(=O)C=C)C(C)=CC=C1N1C(=O)C=CC2=C1C1=CC(C=3C=CC(NS(C)(=O)=O)=CC=3)=CC=C1N=C2 SFMJNHNUOVADRW-UHFFFAOYSA-N 0.000 description 1
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- KWGRBVOPPLSCSI-WCBMZHEXSA-N pseudoephedrine Chemical compound CN[C@@H](C)[C@@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WCBMZHEXSA-N 0.000 description 1
- 229960003908 pseudoephedrine Drugs 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 239000012047 saturated solution Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
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- 230000000862 serotonergic effect Effects 0.000 description 1
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- 239000000741 silica gel Substances 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 125000005374 siloxide group Chemical group 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical class [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
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- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
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- 238000007920 subcutaneous administration Methods 0.000 description 1
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- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 230000006103 sulfonylation Effects 0.000 description 1
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- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 210000001685 thyroid gland Anatomy 0.000 description 1
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- XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
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- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 235000013337 tricalcium citrate Nutrition 0.000 description 1
- QWEJGTIVESCYNM-UHFFFAOYSA-N trimethyl-[2-(2-trimethylsilylethoxymethoxymethoxy)ethyl]silane Chemical compound C[Si](C)(C)CCOCOCOCC[Si](C)(C)C QWEJGTIVESCYNM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
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US12229299P | 1999-03-01 | 1999-03-01 | |
PCT/IB2000/000183 WO2000051971A1 (en) | 1999-03-01 | 2000-02-21 | Oxamic acids and derivatives as thyroid receptor ligands |
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HR20010633A HRP20010633A2 (en) | 1999-03-01 | 2001-08-30 | Oxamic acids and derivatives as thyroid receptor ligands |
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WO2022011120A1 (en) * | 2020-07-10 | 2022-01-13 | Aligos Therapeutics, Inc. | MODULATORS OF THR-β AND METHODS OF USE THEREOF |
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US4069343A (en) | 1973-03-23 | 1978-01-17 | American Home Products Corporation | Oxamic acid derivatives for the prevention of immediate type hypersensitivity reactions |
US4554290A (en) | 1983-06-17 | 1985-11-19 | Ciba-Geigy Corporation | Oxamic acid derivatives |
US5061798A (en) | 1985-01-18 | 1991-10-29 | Smith Kline & French Laboratories, Ltd. | Benzyl pyridyl and pyridazinyl compounds |
GB8501372D0 (en) | 1985-01-18 | 1985-02-20 | Smith Kline French Lab | Chemical compounds |
US5232947A (en) | 1988-07-04 | 1993-08-03 | Meiji Seika Kaisha, Ltd. | Oxamic acid compounds and pharmaceutical composition for use in improvement of damaged cerebral functions of brain |
US5284971A (en) | 1992-07-16 | 1994-02-08 | Syntex (U.S.A.) Inc. | 4-(3-cyclohexyl-4-hydroxy or-methoxy phenylsulfonyl) 3,5 dibromo phenyl acetic thyromimetic cholesterol-lowering agents |
ES2108855T3 (es) | 1992-07-21 | 1998-01-01 | Ciba Geigy Ag | Derivados de acido oxamico como agentes hipocolesteremicos. |
GB9816935D0 (en) * | 1998-08-05 | 1998-09-30 | Karobio Ab | Novel glucocortoid and thyroid receptor ligands for the treatment of metabolic disorders |
CA2363145C (en) * | 1999-03-01 | 2006-02-14 | Pfizer Products Inc. | Oxamic acids and derivatives as thyroid receptor ligands |
CO5160290A1 (es) | 1999-03-29 | 2002-05-30 | Novartis Ag | Derivados de acido fenoxifeniloxamico sustituido . |
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