JP2013520397A5 - - Google Patents
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- JP2013520397A5 JP2013520397A5 JP2012538520A JP2012538520A JP2013520397A5 JP 2013520397 A5 JP2013520397 A5 JP 2013520397A5 JP 2012538520 A JP2012538520 A JP 2012538520A JP 2012538520 A JP2012538520 A JP 2012538520A JP 2013520397 A5 JP2013520397 A5 JP 2013520397A5
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- ethyl
- amino
- carbon atoms
- Prior art date
- 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.)
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- 125000004432 carbon atom Chemical group C* 0.000 claims description 135
- 125000000217 alkyl group Chemical group 0.000 claims description 122
- 125000005843 halogen group Chemical group 0.000 claims description 108
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 77
- 125000003545 alkoxy group Chemical group 0.000 claims description 77
- 125000003118 aryl group Chemical group 0.000 claims description 77
- -1 oxopiperidyl group Chemical group 0.000 claims description 70
- 125000002950 monocyclic group Chemical group 0.000 claims description 59
- 125000003277 amino group Chemical group 0.000 claims description 55
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 47
- 150000001875 compounds Chemical class 0.000 claims description 45
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 44
- 229910052757 nitrogen Inorganic materials 0.000 claims description 42
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- 125000004434 sulfur atom Chemical group 0.000 claims description 40
- 125000002619 bicyclic group Chemical group 0.000 claims description 36
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 36
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 29
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 29
- 239000004202 carbamide Substances 0.000 claims description 29
- 125000005842 heteroatom Chemical group 0.000 claims description 28
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 27
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 26
- 125000004760 (C1-C4) alkylsulfonylamino group Chemical group 0.000 claims description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 23
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- 229910052717 sulfur Inorganic materials 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 18
- 125000003342 alkenyl group Chemical group 0.000 claims description 18
- 125000004414 alkyl thio group Chemical group 0.000 claims description 18
- 125000002947 alkylene group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 18
- 241001465754 Metazoa Species 0.000 claims description 17
- 241000124008 Mammalia Species 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 150000002367 halogens Chemical group 0.000 claims description 14
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 12
- 206010020751 Hypersensitivity Diseases 0.000 claims description 12
- 102000013264 Interleukin-23 Human genes 0.000 claims description 12
- 108010065637 Interleukin-23 Proteins 0.000 claims description 12
- 230000007815 allergy Effects 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 208000026278 immune system disease Diseases 0.000 claims description 12
- 230000001404 mediated effect Effects 0.000 claims description 12
- 125000004043 oxo group Chemical group O=* 0.000 claims description 12
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 125000005936 piperidyl group Chemical group 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 125000005476 oxopyrrolidinyl group Chemical group 0.000 claims description 10
- 230000001225 therapeutic effect Effects 0.000 claims description 10
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 9
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 9
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
- 239000005711 Benzoic acid Substances 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- 235000010233 benzoic acid Nutrition 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 8
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 230000002265 prevention Effects 0.000 claims description 8
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 7
- DOTIWNYTQPDMBR-ZDUSSCGKSA-N 4-[(1s)-1-[[2,5-dimethyl-4-[[4-(trifluoromethyl)phenyl]methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(C)SC(C)=C1CC1=CC=C(C(F)(F)F)C=C1 DOTIWNYTQPDMBR-ZDUSSCGKSA-N 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 6
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 6
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- FKXDPPYCCKCVCW-LBPRGKRZSA-N 4-[(1s)-1-[[5-chloro-2-(3-fluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=CC(F)=C1 FKXDPPYCCKCVCW-LBPRGKRZSA-N 0.000 claims description 5
- JJWCQIGUTYSYQF-ZDUSSCGKSA-N 4-[(1s)-1-[[5-chloro-2-[(3-chlorophenoxy)methyl]pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1COC1=CC=CC(Cl)=C1 JJWCQIGUTYSYQF-ZDUSSCGKSA-N 0.000 claims description 5
- IXDVRRPNWPOPGV-UHFFFAOYSA-N 4-[[4-(5-methoxypyridin-2-yl)phenoxy]methyl]-5-methyl-n-(2-methylphenyl)sulfonylfuran-2-carboxamide Chemical compound N1=CC(OC)=CC=C1C(C=C1)=CC=C1OCC1=C(C)OC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=C1 IXDVRRPNWPOPGV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 125000006413 ring segment Chemical group 0.000 claims description 5
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 4
- LRAMPOFRCGKEAQ-AWEZNQCLSA-N 2,5-dimethyl-n-[(1s)-1-[4-(methylsulfonylcarbamoyl)phenyl]ethyl]-4-[[4-(trifluoromethyl)phenyl]methyl]thiophene-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(=O)NS(C)(=O)=O)C(=O)C1=C(C)SC(C)=C1CC1=CC=C(C(F)(F)F)C=C1 LRAMPOFRCGKEAQ-AWEZNQCLSA-N 0.000 claims description 4
- CIEAOSWNZSOPSF-UHFFFAOYSA-N 2,5-dimethyl-n-[1-[4-(2h-tetrazol-5-yl)phenyl]cyclopropyl]-4-[[3-(trifluoromethyl)phenyl]methyl]thiophene-3-carboxamide Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC1=C(C)SC(C)=C1C(=O)NC1(C=2C=CC(=CC=2)C2=NNN=N2)CC1 CIEAOSWNZSOPSF-UHFFFAOYSA-N 0.000 claims description 4
- FMLJGBDOSCBJBZ-UHFFFAOYSA-N 2,5-dimethyl-n-[1-[4-(2h-tetrazol-5-yl)phenyl]cyclopropyl]-4-[[4-(trifluoromethyl)phenyl]methyl]thiophene-3-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1CC1=C(C)SC(C)=C1C(=O)NC1(C=2C=CC(=CC=2)C2=NNN=N2)CC1 FMLJGBDOSCBJBZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 4
- YQUNVWHOTJLOLI-LLVKDONJSA-N 4-[(1r)-1-[[2,5-dichloro-4-[(3-chlorophenyl)methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Cl)SC(Cl)=C1CC1=CC=CC(Cl)=C1 YQUNVWHOTJLOLI-LLVKDONJSA-N 0.000 claims description 4
- KMCFCSKMVIRYBI-NSHDSACASA-N 4-[(1s)-1-[[2,5-dibromo-4-[(3-chlorophenyl)methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Br)SC(Br)=C1CC1=CC=CC(Cl)=C1 KMCFCSKMVIRYBI-NSHDSACASA-N 0.000 claims description 4
- WUZXHEDPFNIOGV-JTQLQIEISA-N 4-[(1s)-1-[[2,5-dichloro-4-(3-chlorobenzoyl)thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Cl)SC(Cl)=C1C(=O)C1=CC=CC(Cl)=C1 WUZXHEDPFNIOGV-JTQLQIEISA-N 0.000 claims description 4
- UUZOSJJYPGRLFD-YGXOJQJDSA-N 4-[(1s)-1-[[2,5-dichloro-4-[(3-chlorophenyl)-(oxan-2-yloxy)methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Cl)SC(Cl)=C1C(C=1C=C(Cl)C=CC=1)OC1CCCCO1 UUZOSJJYPGRLFD-YGXOJQJDSA-N 0.000 claims description 4
- YJEXRJWDVWQMEX-YOZOHBORSA-N 4-[(1s)-1-[[2,5-dichloro-4-[(3-chlorophenyl)-hydroxymethyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Cl)SC(Cl)=C1C(O)C1=CC=CC(Cl)=C1 YJEXRJWDVWQMEX-YOZOHBORSA-N 0.000 claims description 4
- YQUNVWHOTJLOLI-NSHDSACASA-N 4-[(1s)-1-[[2,5-dichloro-4-[(3-chlorophenyl)methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Cl)SC(Cl)=C1CC1=CC=CC(Cl)=C1 YQUNVWHOTJLOLI-NSHDSACASA-N 0.000 claims description 4
- ASHWHAHRKQFQAR-NSHDSACASA-N 4-[(1s)-1-[[2,5-dichloro-4-[[3-(trifluoromethyl)phenyl]methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(Cl)SC(Cl)=C1CC1=CC=CC(C(F)(F)F)=C1 ASHWHAHRKQFQAR-NSHDSACASA-N 0.000 claims description 4
- DLMXCAVYRXOLRT-ZDUSSCGKSA-N 4-[(1s)-1-[[2,5-dimethyl-4-[[3-(trifluoromethyl)phenyl]methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(C)SC(C)=C1CC1=CC=CC(C(F)(F)F)=C1 DLMXCAVYRXOLRT-ZDUSSCGKSA-N 0.000 claims description 4
- YZTUSPHKCBTOSQ-ZDUSSCGKSA-N 4-[(1s)-1-[[4-[(3-chlorophenyl)methyl]-2,5-dimethylthiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(C)SC(C)=C1CC1=CC=CC(Cl)=C1 YZTUSPHKCBTOSQ-ZDUSSCGKSA-N 0.000 claims description 4
- CKYFFWHUNIOYDH-ZDUSSCGKSA-N 4-[(1s)-1-[[4-[(3-chlorophenyl)methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CSC=C1CC1=CC=CC(Cl)=C1 CKYFFWHUNIOYDH-ZDUSSCGKSA-N 0.000 claims description 4
- FADNAZBPTQVMPQ-ZDUSSCGKSA-N 4-[(1s)-1-[[4-[(4-chlorophenyl)methyl]-2,5-dimethylthiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=C(C)SC(C)=C1CC1=CC=C(Cl)C=C1 FADNAZBPTQVMPQ-ZDUSSCGKSA-N 0.000 claims description 4
- RZBIFXATYGZAHD-LBPRGKRZSA-N 4-[(1s)-1-[[5-bromo-4-[(3-chlorophenyl)methyl]thiophene-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CSC(Br)=C1CC1=CC=CC(Cl)=C1 RZBIFXATYGZAHD-LBPRGKRZSA-N 0.000 claims description 4
- FFFKIGGQAODEPS-UHFFFAOYSA-N 4-[1-[[2,5-dimethyl-4-[[3-(trifluoromethyl)phenyl]methyl]thiophene-3-carbonyl]amino]cyclopropyl]benzoic acid Chemical compound C=1C=CC(C(F)(F)F)=CC=1CC1=C(C)SC(C)=C1C(=O)NC1(C=2C=CC(=CC=2)C(O)=O)CC1 FFFKIGGQAODEPS-UHFFFAOYSA-N 0.000 claims description 4
- NCZZPAVJNDIVAY-UHFFFAOYSA-N 4-[1-[[5-chloro-3-[(3-chlorophenyl)methyl]thiophene-2-carbonyl]amino]ethyl]benzoic acid Chemical compound C=1C=C(C(O)=O)C=CC=1C(C)NC(=O)C=1SC(Cl)=CC=1CC1=CC=CC(Cl)=C1 NCZZPAVJNDIVAY-UHFFFAOYSA-N 0.000 claims description 4
- BGASCMMYJZPCSS-UHFFFAOYSA-N 4-[[[2,5-dichloro-4-[(3-chlorophenyl)methyl]thiophene-3-carbonyl]amino]methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CNC(=O)C1=C(Cl)SC(Cl)=C1CC1=CC=CC(Cl)=C1 BGASCMMYJZPCSS-UHFFFAOYSA-N 0.000 claims description 4
- PYWZJCKVQWUVPO-UHFFFAOYSA-N 5-chloro-3-[(3-chlorophenyl)methyl]-n-[1-[4-(2h-tetrazol-5-yl)phenyl]ethyl]thiophene-2-carboxamide Chemical compound C=1C=C(C=2NN=NN=2)C=CC=1C(C)NC(=O)C=1SC(Cl)=CC=1CC1=CC=CC(Cl)=C1 PYWZJCKVQWUVPO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 208000026935 allergic disease Diseases 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- ZAILXIKGMGZJPJ-SFHVURJKSA-N n-[(1s)-1-[4-(benzenesulfonylcarbamoyl)phenyl]ethyl]-2,5-dimethyl-4-[[4-(trifluoromethyl)phenyl]methyl]thiophene-3-carboxamide Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(=O)NS(=O)(=O)C=1C=CC=CC=1)C(=O)C1=C(C)SC(C)=C1CC1=CC=C(C(F)(F)F)C=C1 ZAILXIKGMGZJPJ-SFHVURJKSA-N 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 208000024891 symptom Diseases 0.000 claims description 4
- 125000006590 (C2-C6) alkenylene group Chemical group 0.000 claims description 3
- 125000006591 (C2-C6) alkynylene group Chemical group 0.000 claims description 3
- BTXUOUJHLMYLQA-ZDUSSCGKSA-N 4-[(1s)-1-[[2-[(4-chlorophenoxy)methyl]-5-fluoropyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(F)=CN=C1COC1=CC=C(Cl)C=C1 BTXUOUJHLMYLQA-ZDUSSCGKSA-N 0.000 claims description 3
- ZGFNLKCVKKEJKU-LBPRGKRZSA-N 4-[(1s)-1-[[5-chloro-2-(2,3-difluorophenoxy)benzoyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CC=C1OC1=CC=CC(F)=C1F ZGFNLKCVKKEJKU-LBPRGKRZSA-N 0.000 claims description 3
- VKIBSGBBHPHLTP-NSHDSACASA-N 4-[(1s)-1-[[5-chloro-2-(2,3-difluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=CC(F)=C1F VKIBSGBBHPHLTP-NSHDSACASA-N 0.000 claims description 3
- POCXSXWWUUVJIB-NSHDSACASA-N 4-[(1s)-1-[[5-chloro-2-(2-chloro-4-fluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=C(F)C=C1Cl POCXSXWWUUVJIB-NSHDSACASA-N 0.000 claims description 3
- AMOAVOIZVZLGMJ-LBPRGKRZSA-N 4-[(1s)-1-[[5-chloro-2-(3,4-difluorophenoxy)benzoyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CC=C1OC1=CC=C(F)C(F)=C1 AMOAVOIZVZLGMJ-LBPRGKRZSA-N 0.000 claims description 3
- NWAARQJHDWAZKA-NSHDSACASA-N 4-[(1s)-1-[[5-chloro-2-(3,4-difluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=C(F)C(F)=C1 NWAARQJHDWAZKA-NSHDSACASA-N 0.000 claims description 3
- JDYZXLWEPUFOQR-NSHDSACASA-N 4-[(1s)-1-[[5-chloro-2-(3-chloro-5-fluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC(F)=CC(Cl)=C1 JDYZXLWEPUFOQR-NSHDSACASA-N 0.000 claims description 3
- PSRWNAXGTLCGIF-ZDUSSCGKSA-N 4-[(1s)-1-[[5-chloro-2-(3-chlorophenoxy)benzoyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CC=C1OC1=CC=CC(Cl)=C1 PSRWNAXGTLCGIF-ZDUSSCGKSA-N 0.000 claims description 3
- PAASJZUYDQEILO-LBPRGKRZSA-N 4-[(1s)-1-[[5-chloro-2-(3-chlorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=CC(Cl)=C1 PAASJZUYDQEILO-LBPRGKRZSA-N 0.000 claims description 3
- QEJPFCHVBBYBQL-ZDUSSCGKSA-N 4-[(1s)-1-[[5-chloro-2-(3-cyanophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=CC(C#N)=C1 QEJPFCHVBBYBQL-ZDUSSCGKSA-N 0.000 claims description 3
- HXOWIUWRSXNBNJ-ZDUSSCGKSA-N 4-[(1s)-1-[[5-chloro-2-(3-fluorophenoxy)benzoyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CC=C1OC1=CC=CC(F)=C1 HXOWIUWRSXNBNJ-ZDUSSCGKSA-N 0.000 claims description 3
- KQRDIJJCEPLGDK-LBPRGKRZSA-N 4-[(1s)-1-[[5-chloro-2-(4-fluorophenoxy)pyridine-3-carbonyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CN=C1OC1=CC=C(F)C=C1 KQRDIJJCEPLGDK-LBPRGKRZSA-N 0.000 claims description 3
- XWIHFKIHPJOELR-INIZCTEOSA-N 4-[(1s)-1-[[5-chloro-2-(cyclohexylmethoxymethyl)benzoyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CC=C1COCC1CCCCC1 XWIHFKIHPJOELR-INIZCTEOSA-N 0.000 claims description 3
- ATOZZVAPMQDUSI-ZDUSSCGKSA-N 4-[(1s)-1-[[5-chloro-2-[(2,4-difluorophenoxy)methyl]benzoyl]amino]ethyl]benzoic acid Chemical compound N([C@@H](C)C=1C=CC(=CC=1)C(O)=O)C(=O)C1=CC(Cl)=CC=C1COC1=CC=C(F)C=C1F ATOZZVAPMQDUSI-ZDUSSCGKSA-N 0.000 claims description 3
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| AR091429A1 (es) | 2012-06-29 | 2015-02-04 | Lilly Co Eli | Compuestos de fenoxietil piperidina |
| UA115576C2 (uk) * | 2012-12-06 | 2017-11-27 | Байєр Фарма Акцієнгезелльшафт | Похідні бензимідазолу як антагоністи ер4 |
| EP2765128A1 (en) * | 2013-02-07 | 2014-08-13 | Almirall, S.A. | Substituted benzamides with activity towards EP4 receptors |
| TW201443004A (zh) | 2013-02-15 | 2014-11-16 | Lilly Co Eli | 苯氧基乙氧基化合物 |
| TWI636046B (zh) | 2013-05-17 | 2018-09-21 | 美國禮來大藥廠 | 苯氧基乙基二氫－１ｈ－異喹啉化合物 |
| BR112016011016A8 (pt) | 2013-12-17 | 2018-01-30 | Lilly Co Eli | derivados de fenoxietila de amina cíclica, seus usos, e composição farmacêutica. |
| TW201607943A (zh) * | 2013-12-19 | 2016-03-01 | 拜耳製藥公司 | 作為ｅｐ４配體之新穎苯并咪唑衍生物 |
| US12109218B2 (en) | 2014-12-09 | 2024-10-08 | Aratana Therapeutics, Inc. | Compositions of grapiprant and methods for using the same |
| TWI708606B (zh) | 2014-03-06 | 2020-11-01 | 美商雅瑞塔那醫療公司 | 格拉匹綸(grapiprant)組合物及其使用方法 |
| MX390051B (es) * | 2015-10-16 | 2025-03-20 | Eisai R&D Man Co Ltd | Antagonistas de ep4. |
| US10342785B2 (en) * | 2016-11-04 | 2019-07-09 | Askat Inc. | Use of EP4 receptor antagonists for the treatment of NASH-associated liver cancer |
| CN110366549A (zh) | 2017-01-23 | 2019-10-22 | 基因泰克公司 | 作为白介素-1活性抑制剂的化合物 |
| CN109836434B (zh) * | 2017-11-27 | 2020-09-25 | 上海宇耀生物科技有限公司 | 噻吩并环类化合物及其合成方法和应用 |
| CA3096546A1 (en) | 2018-04-16 | 2019-10-24 | Arrys Therapeutics, Inc. | Ep4 inhibitors and use thereof |
| US10239885B1 (en) | 2018-06-18 | 2019-03-26 | Avista Pharma Solutions, Inc. | Compound 1-[2-[4-(2-ethyl-6,8-dimethylimidazo[1,2-α]pyrazin-3-yl)phenyl]ethyl]-3-(p-tolylsulfonyl)urea as a prostaglandin EP4 receptor antagonist |
| WO2020014465A1 (en) | 2018-07-11 | 2020-01-16 | Arrys Therapeutics, Inc. | Polymorphic compounds and uses thereof |
| KR20210034596A (ko) | 2018-07-20 | 2021-03-30 | 에프. 호프만-라 로슈 아게 | 인터류킨-1 활성의 저해제로서 술폰이미드아미드 화합물 |
| WO2020018970A1 (en) * | 2018-07-20 | 2020-01-23 | Genentech, Inc. | Sulfonylurea compounds as inhibitors of interleukin-1 activity |
| IL316875A (en) | 2018-10-05 | 2025-01-01 | Annapurna Bio Inc | Compounds and compositions for treating conditions associated with APJ receptor activity |
| MX2021009251A (es) | 2019-01-30 | 2021-09-21 | Avista Pharma Solutions Inc | Proceso de sintesis y nuevos compuestos intermedios. |
| WO2020160075A1 (en) | 2019-01-30 | 2020-08-06 | Avista Pharma Solutions, Inc. | Chemical compounds |
| WO2021205367A1 (en) * | 2020-04-08 | 2021-10-14 | Askat Inc. | Use of ep4 receptor antagonists for the treatment of liver cancer, melanoma, lymphoma and leukemia |
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| IL164263A0 (en) | 2002-04-12 | 2005-12-18 | Pfizer | Use of ep4 receptor ligands on the treatment of il-6 involved diseases |
| AU2004207675B2 (en) * | 2003-01-29 | 2010-05-20 | Asterand Uk Acquisition Limited | EP4 receptor antagonists |
| GB0302094D0 (en) | 2003-01-29 | 2003-02-26 | Pharmagene Lab Ltd | EP4 receptor antagonists |
| BRPI0414130B8 (pt) * | 2003-09-03 | 2021-05-25 | Askat Inc | compostos de fenilamida ou piridilamida, seu uso e composições farmacêuticas que os compreendem. |
| JP2007533723A (ja) * | 2004-04-20 | 2007-11-22 | ファイザー・プロダクツ・インク | α２δリガンドを含む組合せ |
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| AU2006221699A1 (en) | 2005-03-11 | 2006-09-14 | Pfizer Inc. | Crystal forms of an imidazole derivative |
| US8969394B2 (en) | 2006-08-11 | 2015-03-03 | Merck Frosst Canada Ltd. | Thiophenecarboxamide derivatives as EP4 receptor ligands |
| EP1886987A1 (en) * | 2006-08-11 | 2008-02-13 | Givaudan S.A. | Process for producing 2,2,3-trimethylcyclopent-3-enecarbaldehyde (campholytic aldehyde) |
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2018
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