NZ523822A - Non-steroidal inflammation inhibitors - Google Patents
Non-steroidal inflammation inhibitorsInfo
- Publication number
- NZ523822A NZ523822A NZ523822A NZ52382201A NZ523822A NZ 523822 A NZ523822 A NZ 523822A NZ 523822 A NZ523822 A NZ 523822A NZ 52382201 A NZ52382201 A NZ 52382201A NZ 523822 A NZ523822 A NZ 523822A
- Authority
- NZ
- New Zealand
- Prior art keywords
- methyl
- hydroxy
- benzoxazin
- amino
- trifluoromethyl
- Prior art date
Links
- 206010061218 Inflammation Diseases 0.000 title claims abstract description 10
- 230000004054 inflammatory process Effects 0.000 title claims abstract description 10
- 239000003112 inhibitor Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 238000000034 method Methods 0.000 claims abstract description 53
- 230000008569 process Effects 0.000 claims abstract description 51
- 238000004519 manufacturing process Methods 0.000 claims abstract description 15
- 239000008177 pharmaceutical agent Substances 0.000 claims abstract description 10
- -1 heteroaryl radical Chemical class 0.000 claims description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 230000002757 inflammatory effect Effects 0.000 claims description 21
- 208000010668 atopic eczema Diseases 0.000 claims description 19
- 230000000172 allergic effect Effects 0.000 claims description 17
- 230000000694 effects Effects 0.000 claims description 17
- 230000002062 proliferating effect Effects 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- PDSZQDJIKVTPHU-UHFFFAOYSA-N 4-methyl-2,3-benzoxazin-1-one Chemical compound C1=CC=C2C(C)=NOC(=O)C2=C1 PDSZQDJIKVTPHU-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 201000010099 disease Diseases 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
- 150000003254 radicals Chemical class 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- AMNTZAJRQYSGSI-UHFFFAOYSA-N 4-(2,3-difluorophenyl)-2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)hexanamide Chemical compound C=1C=C(C(ON=C2C)=O)C2=CC=1NC(=O)C(O)(C(F)(F)F)CC(C)(CC)C1=CC=CC(F)=C1F AMNTZAJRQYSGSI-UHFFFAOYSA-N 0.000 claims description 8
- 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 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
- 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 7
- HSTZEGAFCBTUFY-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-4-naphthalen-1-yl-2-(trifluoromethyl)pentanamide Chemical compound C1=CC=C2C(C(C)(C)CC(O)(C(=O)NC3=CC=C4C(=O)ON=C(C4=C3)C)C(F)(F)F)=CC=CC2=C1 HSTZEGAFCBTUFY-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- 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 7
- 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 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 230000006698 induction Effects 0.000 claims description 7
- 238000002560 therapeutic procedure Methods 0.000 claims description 7
- 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
- BCXNZLIRXKTGNM-UHFFFAOYSA-N 2-hydroxy-4-methyl-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-(trifluoromethyl)-4-(2,3,4-trifluorophenyl)pentanamide Chemical compound C1=C2C(C)=NOC(=O)C2=CC=C1NC(=O)C(O)(C(F)(F)F)CC(C)(C)C1=CC=C(F)C(F)=C1F BCXNZLIRXKTGNM-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- QPPPPGJJLJDIGS-UHFFFAOYSA-N 4-(2,4-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=C(F)C=C1F QPPPPGJJLJDIGS-UHFFFAOYSA-N 0.000 claims description 6
- PMAHVVINAJZRAE-UHFFFAOYSA-N 4-(2,5-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=C1F PMAHVVINAJZRAE-UHFFFAOYSA-N 0.000 claims description 6
- RDVSAQOQBBMCRS-UHFFFAOYSA-N 4-(2,6-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=C(F)C=CC=C1F RDVSAQOQBBMCRS-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 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 6
- LKDUCHKMZJJSMQ-UHFFFAOYSA-N 4-(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=C1F LKDUCHKMZJJSMQ-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- QBUFKXHAIFPIKQ-UHFFFAOYSA-N 5-amino-4-methyl-6-[3,3,3-trifluoro-2-hydroxy-2-[[1-[2-(trifluoromethyl)phenyl]cyclohexyl]methyl]propanoyl]-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)C(F)(F)F)CCCCC1 QBUFKXHAIFPIKQ-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
- JGLQMQDTLXJDRH-UHFFFAOYSA-N 5-amino-6-[4-(2,3-dichlorophenyl)-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=CC(Cl)=C1Cl JGLQMQDTLXJDRH-UHFFFAOYSA-N 0.000 claims description 6
- BZEINGJAZXMFTH-UHFFFAOYSA-N 5-amino-6-[4-(2,4-dichlorophenyl)-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(Cl)C=C1Cl BZEINGJAZXMFTH-UHFFFAOYSA-N 0.000 claims description 6
- IXSOKKOLFMGIJH-UHFFFAOYSA-N 5-amino-6-[4-(2-chloro-3-hydroxyphenyl)-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=CC(O)=C1Cl IXSOKKOLFMGIJH-UHFFFAOYSA-N 0.000 claims description 6
- HXKPAXXMFIYYIV-UHFFFAOYSA-N 5-amino-6-[4-(2-chloro-6-fluorophenyl)-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=C(F)C=CC=C1Cl HXKPAXXMFIYYIV-UHFFFAOYSA-N 0.000 claims description 6
- CHBCOOSCRPRLFN-UHFFFAOYSA-N 5-amino-6-[4-(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=CC=C1Cl CHBCOOSCRPRLFN-UHFFFAOYSA-N 0.000 claims description 6
- 102000004357 Transferases Human genes 0.000 claims description 6
- 108090000992 Transferases Proteins 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 5
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims description 5
- 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 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
- LEVWUZJIDRRVGC-UHFFFAOYSA-N 3,3,3-trifluoro-2-hydroxy-n-(4-methyl-1-oxo-2,3-benzoxazin-6-yl)-2-[[1-(2,3,5-trifluorophenyl)cyclobutyl]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)CCC1 LEVWUZJIDRRVGC-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
- 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 5
- 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 5
- 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 5
- IYHOZRPCBYJYLG-UHFFFAOYSA-N 5-amino-4-methyl-6-[3,3,3-trifluoro-2-hydroxy-2-[[1-[2-(trifluoromethyl)phenyl]cyclopropyl]methyl]propanoyl]-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)C(F)(F)F)CC1 IYHOZRPCBYJYLG-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 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 5
- 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 5
- MQKYRKNLWYUECH-UHFFFAOYSA-N 5-amino-6-[4-(2-chloro-3-fluorophenyl)-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=CC(F)=C1Cl MQKYRKNLWYUECH-UHFFFAOYSA-N 0.000 claims description 5
- XTVCJDDEEYRMLB-UHFFFAOYSA-N 5-amino-6-[4-(2-chloro-3-methoxyphenyl)-2-hydroxy-4-methyl-2-(trifluoromethyl)pentanoyl]-4-methyl-2,3-benzoxazin-1-one Chemical compound COC1=CC=CC(C(C)(C)CC(O)(C(=O)C=2C(=C3C(C(ON=C3C)=O)=CC=2)N)C(F)(F)F)=C1Cl XTVCJDDEEYRMLB-UHFFFAOYSA-N 0.000 claims description 5
- UDHHLKYKGBFSEE-UHFFFAOYSA-N 5-amino-6-[4-(2-chloro-4-fluorophenyl)-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=C1Cl UDHHLKYKGBFSEE-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 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 5
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 5
- 206010020751 Hypersensitivity Diseases 0.000 claims description 5
- 206010028980 Neoplasm Diseases 0.000 claims description 5
- 125000002252 acyl 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
- 150000002148 esters Chemical class 0.000 claims description 5
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
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| DE10038639A DE10038639A1 (de) | 2000-07-28 | 2000-07-28 | Nichtsteroidale Entzündungshemmer |
| PCT/EP2001/008501 WO2002010143A1 (de) | 2000-07-28 | 2001-07-23 | Nichtsteroidale entzündungshemmer |
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| NZ523822A true NZ523822A (en) | 2006-01-27 |
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| NZ523822A NZ523822A (en) | 2000-07-28 | 2001-07-23 | Non-steroidal inflammation inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US6245804B1 (en) | 1997-05-30 | 2001-06-12 | Schering Aktiengesellschaft | Nonsteroidal gestagens |
| DE19723722A1 (de) | 1997-05-30 | 1998-12-10 | Schering Ag | Nichtsteroidale Gestagene |
| DE19856475A1 (de) * | 1998-11-27 | 2000-05-31 | Schering Ag | Nichtsteroidale Entzündungshemmer |
| JP3464405B2 (ja) * | 1999-02-18 | 2003-11-10 | 阪神化成工業株式会社 | 多層薄肉容器 |
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