BG107488A - Нестероидални инхибитори на възпаление - Google Patents

Info

Publication number

BG107488A

BG107488A BG107488A BG10748803A BG107488A BG 107488 A BG107488 A BG 107488A BG 107488 A BG107488 A BG 107488A BG 10748803 A BG10748803 A BG 10748803A BG 107488 A BG107488 A BG 107488A

Authority

BG

Bulgaria

Prior art keywords

methyl

hydroxy

benzoxazin

amino

fluorophenyl

Prior art date

2000-07-28

Links

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• Global Dossier
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• 206010061218 Inflammation Diseases 0.000 title claims abstract description 12
• 230000004054 inflammatory process Effects 0.000 title claims abstract description 12
• 239000003112 inhibitor Substances 0.000 title abstract description 3
• 150000001875 compounds Chemical class 0.000 claims abstract description 109
• 238000000034 method Methods 0.000 claims abstract description 46
• -1 6- [4- (5-chloro-2-nitrophenyl) -2-hydroxy-4-methyl-2trifluoromethylvaleroylamino] -4-methyl-2,3-benzoxazin-1-one Chemical compound 0.000 claims description 184
• 125000000217 alkyl group Chemical group 0.000 claims description 38
• 230000008569 process Effects 0.000 claims description 28
• 238000002360 preparation method Methods 0.000 claims description 27
• 230000002757 inflammatory effect Effects 0.000 claims description 26
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 23
• 208000010668 atopic eczema Diseases 0.000 claims description 19
• 229910052739 hydrogen Inorganic materials 0.000 claims description 19
• 239000001257 hydrogen Substances 0.000 claims description 19
• 230000000172 allergic effect Effects 0.000 claims description 18
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 18
• 201000010099 disease Diseases 0.000 claims description 17
• 230000002062 proliferating effect Effects 0.000 claims description 17
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
• 239000002253 acid Substances 0.000 claims description 15
• 125000002252 acyl group Chemical group 0.000 claims description 13
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 230000036961 partial effect Effects 0.000 claims description 13
• NUIZBGCUWTXJRW-UHFFFAOYSA-N 4-(2-bromo-3-hydroxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(O)=C1Br NUIZBGCUWTXJRW-UHFFFAOYSA-N 0.000 claims description 12
• 239000003814 drug Substances 0.000 claims description 12
• VDWWFLOAUXTOFA-UHFFFAOYSA-N 4-(2-bromo-3-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=CC(C(C)(C)CC(O)(C(=O)NC=2C=C3C(C(ON=C3C)=O)=CC=2)C(F)(F)F)=C1Br VDWWFLOAUXTOFA-UHFFFAOYSA-N 0.000 claims description 11
• JWWVMXAQAXQFKX-UHFFFAOYSA-N 2-[[4-(2-chloro-5-fluorophenyl)oxan-4-yl]methyl]-3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)Cl)CCOCC1 JWWVMXAQAXQFKX-UHFFFAOYSA-N 0.000 claims description 10
• 238000011282 treatment Methods 0.000 claims description 10
• 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 9
• LLTOISLBDAWTME-UHFFFAOYSA-N 4-(2-ethenyl-5-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1C=C LLTOISLBDAWTME-UHFFFAOYSA-N 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
• IBJHGYJYTFUNMA-UHFFFAOYSA-N 2-hydroxy-4-methyl-4-(3-methyl-2-nitrophenyl)-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC1=CC=CC(C(C)(C)CC(O)(C(=O)NC=2C=C3C(C(ON=C3C)=O)=CC=2)C(F)(F)F)=C1[N+]([O-])=O IBJHGYJYTFUNMA-UHFFFAOYSA-N 0.000 claims description 8
• SIIAKILUARIHSZ-UHFFFAOYSA-N 4-(2-amino-5-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1N SIIAKILUARIHSZ-UHFFFAOYSA-N 0.000 claims description 8
• NJKIIKFLRNIFHD-UHFFFAOYSA-N 4-(2-bromo-3,5-difluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC(F)=C1Br NJKIIKFLRNIFHD-UHFFFAOYSA-N 0.000 claims description 8
• AMWKTALQLOCTEY-UHFFFAOYSA-N 4-[5-fluoro-2-(methanesulfonamido)phenyl]-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1NS(C)(=O)=O AMWKTALQLOCTEY-UHFFFAOYSA-N 0.000 claims description 8
• 125000003118 aryl group Chemical group 0.000 claims description 8
• JZAVYXZWFNKXJG-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)-4-[4-(trifluoromethyl)phenyl]pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(C(F)(F)F)C=C1 JZAVYXZWFNKXJG-UHFFFAOYSA-N 0.000 claims description 7
• OVUGUMQWUWCXMU-UHFFFAOYSA-N 4-(3,5-difluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC(F)=C1 OVUGUMQWUWCXMU-UHFFFAOYSA-N 0.000 claims description 7
• QCRGDJBPYAYILT-UHFFFAOYSA-N 4-(5-fluoro-2-methylphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)ON=C(C)C2=C1 QCRGDJBPYAYILT-UHFFFAOYSA-N 0.000 claims description 7
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 6
• GOOSXGUFDRELNY-UHFFFAOYSA-N 2-[[1-(2,5-difluorophenyl)cyclopropyl]methyl]-3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)F)CC1 GOOSXGUFDRELNY-UHFFFAOYSA-N 0.000 claims description 6
• INLQPJOOWSVYOQ-UHFFFAOYSA-N 2-[[1-(2-bromophenyl)cyclopropyl]methyl]-3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)Br)CC1 INLQPJOOWSVYOQ-UHFFFAOYSA-N 0.000 claims description 6
• QCYJTVUSYHMYFM-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(2-fluorophenyl)cyclohexyl]methyl]-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)F)CCCCC1 QCYJTVUSYHMYFM-UHFFFAOYSA-N 0.000 claims description 6
• QROCAKZRULCDAS-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(2-fluorophenyl)cyclopentyl]methyl]-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)F)CCCC1 QROCAKZRULCDAS-UHFFFAOYSA-N 0.000 claims description 6
• NYUGEJMCBCEKOG-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-[[1-(2,3,5-trifluorophenyl)cyclopropyl]methyl]propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=C(F)C=C(F)C=2)F)CC1 NYUGEJMCBCEKOG-UHFFFAOYSA-N 0.000 claims description 6
• WNHFVTWAARRUTJ-UHFFFAOYSA-N 4-(2-amino-5-fluorophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1N WNHFVTWAARRUTJ-UHFFFAOYSA-N 0.000 claims description 6
• WDDNLHUORBUOJW-UHFFFAOYSA-N 4-(2-bromophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1Br WDDNLHUORBUOJW-UHFFFAOYSA-N 0.000 claims description 6
• BZGUCRMYTFFSKH-UHFFFAOYSA-N 4-(2-chloro-5-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1Cl BZGUCRMYTFFSKH-UHFFFAOYSA-N 0.000 claims description 6
• NGGFWRFSAPXTFL-UHFFFAOYSA-N 4-(4-chloro-2-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(Cl)C=C1F NGGFWRFSAPXTFL-UHFFFAOYSA-N 0.000 claims description 6
• LYIZTUAMCXXRMO-UHFFFAOYSA-N 5-amino-6-[2-[[1-(2-chloro-5-fluorophenyl)cyclopropyl]methyl]-3,3,3-trifluoro-2-hydroxypropanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)Cl)CC1 LYIZTUAMCXXRMO-UHFFFAOYSA-N 0.000 claims description 6
• JGFOCVGKSMIKJH-UHFFFAOYSA-N 5-amino-6-[2-[[1-(2-chlorophenyl)cyclopropyl]methyl]-3,3,3-trifluoro-2-hydroxypropanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)Cl)CC1 JGFOCVGKSMIKJH-UHFFFAOYSA-N 0.000 claims description 6
• GUFSBGAKPRTKTG-UHFFFAOYSA-N 5-amino-6-[2-hydroxy-4-methyl-2-(trifluoromethyl)-4-[2-(trifluoromethyl)phenyl]pentanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC=C1C(F)(F)F GUFSBGAKPRTKTG-UHFFFAOYSA-N 0.000 claims description 6
• LUCGXHAMVUCMCR-UHFFFAOYSA-N 5-amino-6-[4-(4-bromo-2-chlorophenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(Br)C=C1Cl LUCGXHAMVUCMCR-UHFFFAOYSA-N 0.000 claims description 6
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
• 125000003342 alkenyl group Chemical group 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• 150000002148 esters Chemical class 0.000 claims description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• LXLINSAVFRAMPT-UHFFFAOYSA-N 2-[[1-(2,3-difluorophenyl)cyclopropyl]methyl]-3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=C(F)C=CC=2)F)CC1 LXLINSAVFRAMPT-UHFFFAOYSA-N 0.000 claims description 5
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
• CKEDUFCTAPFENH-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(2-fluorophenyl)cyclobutyl]methyl]-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)F)CCC1 CKEDUFCTAPFENH-UHFFFAOYSA-N 0.000 claims description 5
• QFLDUYASXONZQS-UHFFFAOYSA-N 3,3,3-trifluoro-2-[[1-(2-fluorophenyl)cyclopropyl]methyl]-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)F)CC1 QFLDUYASXONZQS-UHFFFAOYSA-N 0.000 claims description 5
• WXGHGFSCDARFCQ-UHFFFAOYSA-N 4-(2-acetamido-5-fluorophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC(=O)NC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C(C(=O)OC2)C2=C1 WXGHGFSCDARFCQ-UHFFFAOYSA-N 0.000 claims description 5
• LKOOMTLSZKAUCJ-UHFFFAOYSA-N 4-(2-acetamido-5-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound CC(=O)NC1=CC=C(F)C=C1C(C)(C)CC(O)(C(F)(F)F)C(=O)NC1=CC=C2C(=O)ON=C(C)C2=C1 LKOOMTLSZKAUCJ-UHFFFAOYSA-N 0.000 claims description 5
• CICLKCYNZNJDNN-UHFFFAOYSA-N 4-(2-fluoro-3-methoxyphenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound COC1=CC=CC(C(C)(C)CC(O)(C(=O)NC=2C=C3C(C(ON=C3C)=O)=CC=2)C(F)(F)F)=C1F CICLKCYNZNJDNN-UHFFFAOYSA-N 0.000 claims description 5
• XGLDVYJOFZDGMU-UHFFFAOYSA-N 4-(5-fluoro-2-nitrophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1[N+]([O-])=O XGLDVYJOFZDGMU-UHFFFAOYSA-N 0.000 claims description 5
• CKWGDIPCFTWNHB-UHFFFAOYSA-N 5-amino-4-methyl-6-[3,3,3-trifluoro-2-[[1-[5-fluoro-2-(trifluoromethyl)phenyl]cyclobutyl]methyl]-2-hydroxypropanoyl]-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)C(F)(F)F)CCC1 CKWGDIPCFTWNHB-UHFFFAOYSA-N 0.000 claims description 5
• NKVZAJQQGORVMB-UHFFFAOYSA-N 5-amino-4-methyl-6-[3,3,3-trifluoro-2-[[1-[5-fluoro-2-(trifluoromethyl)phenyl]cyclopropyl]methyl]-2-hydroxypropanoyl]-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)C(F)(F)F)CC1 NKVZAJQQGORVMB-UHFFFAOYSA-N 0.000 claims description 5
• ZCYSISZXLHQWQA-UHFFFAOYSA-N 5-amino-6-[2-[[1-(2-chlorophenyl)cyclopentyl]methyl]-3,3,3-trifluoro-2-hydroxypropanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=CC=2)Cl)CCCC1 ZCYSISZXLHQWQA-UHFFFAOYSA-N 0.000 claims description 5
• 206010020751 Hypersensitivity Diseases 0.000 claims description 5
• 206010028980 Neoplasm Diseases 0.000 claims description 5
• 206010047700 Vomiting Diseases 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 239000003054 catalyst Substances 0.000 claims description 5
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
• 230000008673 vomiting Effects 0.000 claims description 5
• UCGSQONGHIFVTE-UHFFFAOYSA-N 2-[[1-(2,3-difluorophenyl)cyclobutyl]methyl]-3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)propanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC1(C=2C(=C(F)C=CC=2)F)CCC1 UCGSQONGHIFVTE-UHFFFAOYSA-N 0.000 claims description 4
• PXUAYHLRPKYRRN-UHFFFAOYSA-N 4-(2-bromo-5-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC(F)=CC=C1Br PXUAYHLRPKYRRN-UHFFFAOYSA-N 0.000 claims description 4
• IQBZSTXPSANONE-UHFFFAOYSA-N 4-(3-chloro-2-fluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=CC(Cl)=C1F IQBZSTXPSANONE-UHFFFAOYSA-N 0.000 claims description 4
• WXAUKMWHPOXPCK-UHFFFAOYSA-N 4-(3-fluoro-4-nitrophenyl)-2-hydroxy-4-methyl-n-(1-oxo-3h-2-benzofuran-5-yl)-2-(trifluoromethyl)pentanamide Chemical compound C=1C=C2C(=O)OCC2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C([N+]([O-])=O)C(F)=C1 WXAUKMWHPOXPCK-UHFFFAOYSA-N 0.000 claims description 4
• SHZAGCLNAYBRNL-UHFFFAOYSA-N 5-amino-6-[2-[[1-(2-chloro-4-fluorophenyl)cyclobutyl]methyl]-3,3,3-trifluoro-2-hydroxypropanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC(F)=CC=2)Cl)CCC1 SHZAGCLNAYBRNL-UHFFFAOYSA-N 0.000 claims description 4
• CJGQGWFNRXUOGY-UHFFFAOYSA-N 5-amino-6-[2-[[1-(2-chloro-4-fluorophenyl)cyclopropyl]methyl]-3,3,3-trifluoro-2-hydroxypropanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC(F)=CC=2)Cl)CC1 CJGQGWFNRXUOGY-UHFFFAOYSA-N 0.000 claims description 4
• HGLIPPOOBHTGGU-UHFFFAOYSA-N 5-amino-6-[2-[[1-(2-chloro-5-fluorophenyl)cyclobutyl]methyl]-3,3,3-trifluoro-2-hydroxypropanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC1(C=2C(=CC=C(F)C=2)Cl)CCC1 HGLIPPOOBHTGGU-UHFFFAOYSA-N 0.000 claims description 4
• VAKLTJXFPRHRQF-UHFFFAOYSA-N 5-amino-6-[4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound NC1=C2C(C)=NOC(=O)C2=CC=C1C(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C=C1C(F)(F)F VAKLTJXFPRHRQF-UHFFFAOYSA-N 0.000 claims description 4
• 239000003513 alkali Substances 0.000 claims description 4
• 210000005069 ears Anatomy 0.000 claims description 4
• 229910052757 nitrogen Inorganic materials 0.000 claims description 4
• 239000008194 pharmaceutical composition Substances 0.000 claims description 4
• 150000003839 salts Chemical class 0.000 claims description 4
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