CA2982446A1 - Tricyclic heterocyclic compounds useful as inhibitors of tnf - Google Patents
Tricyclic heterocyclic compounds useful as inhibitors of tnf Download PDFInfo
- Publication number
- CA2982446A1 CA2982446A1 CA2982446A CA2982446A CA2982446A1 CA 2982446 A1 CA2982446 A1 CA 2982446A1 CA 2982446 A CA2982446 A CA 2982446A CA 2982446 A CA2982446 A CA 2982446A CA 2982446 A1 CA2982446 A1 CA 2982446A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- zero
- pyridazin
- imidazo
- difluoromethoxy
- 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.)
- Abandoned
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 6
- 239000003112 inhibitor Substances 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 350
- 150000003839 salts Chemical class 0.000 claims abstract description 116
- 208000023275 Autoimmune disease Diseases 0.000 claims abstract description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 208000027866 inflammatory disease Diseases 0.000 claims abstract description 18
- 230000002757 inflammatory effect Effects 0.000 claims abstract description 14
- JPMJNVODBLZHLR-UHFFFAOYSA-N 5h-imidazo[1,2-b]pyridazin-6-one Chemical compound N1C(=O)C=CC2=NC=CN21 JPMJNVODBLZHLR-UHFFFAOYSA-N 0.000 claims description 141
- -1 -OH Chemical group 0.000 claims description 93
- 125000003118 aryl group Chemical group 0.000 claims description 81
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 77
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- 125000000623 heterocyclic group Chemical group 0.000 claims description 50
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 44
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 125000002950 monocyclic group Chemical group 0.000 claims description 33
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 29
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 28
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000004452 carbocyclyl group Chemical group 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 229910052757 nitrogen Inorganic materials 0.000 claims description 24
- 238000011282 treatment Methods 0.000 claims description 23
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 22
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 claims description 22
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 19
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000003709 fluoroalkyl group Chemical group 0.000 claims description 15
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 15
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 125000004076 pyridyl group Chemical group 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000002757 morpholinyl group Chemical group 0.000 claims description 13
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 12
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 12
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 10
- 125000005605 benzo group Chemical group 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 201000005569 Gout Diseases 0.000 claims description 4
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims description 4
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims description 4
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 4
- 201000006417 multiple sclerosis Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims description 4
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 3
- 208000023328 Basedow disease Diseases 0.000 claims description 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims description 3
- 208000015023 Graves' disease Diseases 0.000 claims description 3
- 208000005777 Lupus Nephritis Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 208000006673 asthma Diseases 0.000 claims description 3
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims description 3
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 2
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 2
- 208000009329 Graft vs Host Disease Diseases 0.000 claims description 2
- 208000024908 graft versus host disease Diseases 0.000 claims description 2
- 206010025135 lupus erythematosus Diseases 0.000 claims description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 230000000737 periodic effect Effects 0.000 claims description 2
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-UHFFFAOYSA-N 0.000 claims description 2
- 208000011580 syndromic disease Diseases 0.000 claims description 2
- 208000020408 systemic-onset juvenile idiopathic arthritis Diseases 0.000 claims description 2
- WARRUQRAZCRUSR-YWZLYKJASA-N (3S,6R)-3-[2-(difluoromethoxy)phenyl]-12-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound CC(C)(O)C1=NC=C(C=N1)C1=NN2C(C=C1)=NC1=C2[C@@H](OC[C@@H]1O)C1=CC=CC=C1OC(F)F WARRUQRAZCRUSR-YWZLYKJASA-N 0.000 claims 4
- OXSABAZYSCHBEW-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=C=CC=C2N=C[CH]N21 OXSABAZYSCHBEW-UHFFFAOYSA-N 0.000 claims 4
- ZJEAUBBRDBFKCO-MBSDFSHPSA-N (3S,6R)-3-[2-(difluoromethoxy)phenyl]-12-[4-(2-hydroxypropan-2-yl)phenyl]-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound CC(C)(O)C1=CC=C(C=C1)C1=NN2C(C=C1)=NC1=C2[C@@H](OC[C@@H]1O)C1=CC=CC=C1OC(F)F ZJEAUBBRDBFKCO-MBSDFSHPSA-N 0.000 claims 2
- ZJEAUBBRDBFKCO-JPYJTQIMSA-N (3S,6S)-3-[2-(difluoromethoxy)phenyl]-12-[4-(2-hydroxypropan-2-yl)phenyl]-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound FC(OC1=C(C=CC=C1)[C@@H]1OC[C@H](C=2N=C3N(N=C(C=C3)C3=CC=C(C=C3)C(C)(C)O)C=21)O)F ZJEAUBBRDBFKCO-JPYJTQIMSA-N 0.000 claims 2
- VERTYDKHQFEQMO-UHFFFAOYSA-N 12-[4-(2-hydroxypropan-2-yl)phenyl]-3-[2-(trifluoromethoxy)phenyl]-1,4,8,13-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound OC(C)(C)C1=CC=C(C=C1)C=1C=CC=2N(N=1)C1=C(N=2)C(CNC1C1=C(C=CC=C1)OC(F)(F)F)O VERTYDKHQFEQMO-UHFFFAOYSA-N 0.000 claims 2
- HLSNOMZQZYVRSL-UHFFFAOYSA-N 2-[4-[3-[2-(difluoromethoxy)phenyl]-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-12-yl]phenyl]propan-2-ol Chemical compound FC(OC1=C(C=CC=C1)C1OCCC=2N=C3N(N=C(C=C3)C3=CC=C(C=C3)C(C)(C)O)C=21)F HLSNOMZQZYVRSL-UHFFFAOYSA-N 0.000 claims 2
- ZDJURXUJJAGERM-UHFFFAOYSA-N 2-[5-[3-[2-(difluoromethoxy)phenyl]-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-12-yl]pyrimidin-2-yl]propan-2-ol Chemical compound FC(OC1=C(C=CC=C1)C1OCCC=2N=C3N(N=C(C=C3)C=3C=NC(=NC=3)C(C)(C)O)C=21)F ZDJURXUJJAGERM-UHFFFAOYSA-N 0.000 claims 2
- ZTAVJSHQCLFIHB-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-12-[4-(2-hydroxypropan-2-yl)phenyl]-6-methyl-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound FC(OC1=C(C=CC=C1)C1OCC(C=2N=C3N(N=C(C=C3)C3=CC=C(C=C3)C(C)(C)O)C=21)(O)C)F ZTAVJSHQCLFIHB-UHFFFAOYSA-N 0.000 claims 2
- OLQONTXLRKBPMD-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-12-[4-(2-hydroxypropan-2-yl)phenyl]-6-pyridin-4-yl-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound FC(OC1=C(C=CC=C1)C1OCC(C=2N=C3N(N=C(C=C3)C3=CC=C(C=C3)C(C)(C)O)C=21)(O)C1=CC=NC=C1)F OLQONTXLRKBPMD-UHFFFAOYSA-N 0.000 claims 2
- FZQQHPGRNQKJSY-NQIIRXRSSA-N (3S,6R)-3-[2-(difluoromethoxy)phenyl]-12-[4-(2-hydroxypropan-2-yl)phenyl]-1,4,8,13-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-6-ol Chemical compound FC(OC1=C(C=CC=C1)[C@@H]1NC[C@H](C=2N=C3N(N=C(C=C3)C3=CC=C(C=C3)C(C)(C)O)C=21)O)F FZQQHPGRNQKJSY-NQIIRXRSSA-N 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- KYRWZLQHRWNMCN-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-12-(1-methylpyrazol-4-yl)-4-oxa-1,8,13-triazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraene Chemical compound FC(OC1=C(C=CC=C1)C1OCCC=2N=C3N(N=C(C=C3)C=3C=NN(C=3)C)C=21)F KYRWZLQHRWNMCN-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 80
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- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
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- 235000010199 sorbic acid Nutrition 0.000 description 1
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- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Epidemiology (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (3)
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| US201562134779P | 2015-03-18 | 2015-03-18 | |
| US62/134,779 | 2015-03-18 | ||
| PCT/US2016/022738 WO2016149437A1 (en) | 2015-03-18 | 2016-03-17 | Tricyclic heterocyclic compounds useful as inhibitors of tnf |
Publications (1)
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| CA2982446A1 true CA2982446A1 (en) | 2016-09-22 |
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| CN (1) | CN107635992B (enExample) |
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| BR (1) | BR112017019731A2 (enExample) |
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| EA (1) | EA032314B1 (enExample) |
| ES (1) | ES2797685T3 (enExample) |
| IL (1) | IL254520A0 (enExample) |
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| AU2016233288A1 (en) | 2015-03-18 | 2017-11-09 | Bristol-Myers Squibb Company | Substituted tricyclic heterocyclic compounds |
| BR112017019605A2 (pt) | 2015-03-18 | 2018-05-08 | Bristol-Myers Squibb Company | compostos heterocíclicos úteis como inibidores de tnf |
| EP3294726A1 (en) | 2015-04-17 | 2018-03-21 | AbbVie Inc. | Indazolones as modulators of tnf signaling |
| EP3286195A1 (en) | 2015-04-17 | 2018-02-28 | AbbVie Inc. | Indazolones as modulators of tnf signaling |
| AR104291A1 (es) | 2015-04-17 | 2017-07-12 | Abbvie Inc | Moduladores tricíclicos de la señalización por tnf |
| GB201510758D0 (en) | 2015-06-18 | 2015-08-05 | Ucb Biopharma Sprl | Novel TNFa structure for use in therapy |
| WO2017023902A1 (en) | 2015-08-03 | 2017-02-09 | Bristol-Myers Squibb Company | Cyclic compounds useful as modulators of tnf alpha |
| GB201621907D0 (en) | 2016-12-21 | 2017-02-01 | Ucb Biopharma Sprl And Sanofi | Antibody epitope |
| EP3596078B1 (en) | 2017-03-15 | 2023-04-12 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
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| US4391806A (en) * | 1982-07-12 | 1983-07-05 | The Dow Chemical Company | Substituted tetrahydropyridazino-(1,6-A)benzimidazoles and use as bronchodilators |
| ATE238998T1 (de) | 1997-02-25 | 2003-05-15 | Us Gov Health & Human Serv | Substituierte benzimidazole als nicht-nucleoside reverse transcriptase inhibitore |
| DE60024480T2 (de) * | 1999-10-27 | 2006-07-27 | Novartis Ag | Thiazol und imidazo[4,5-b]pyridin verbindungen und ihre verwendung als pharmazeutika |
| JPWO2003064422A1 (ja) | 2002-01-31 | 2005-05-26 | 第一製薬株式会社 | イミダゾ［１，２−ａ］ピリジン誘導体 |
| WO2004050035A2 (en) | 2002-12-03 | 2004-06-17 | Isis Pharmaceuticals, Inc. | Benzimidazoles and analogs thereof as antivirals |
| US20050124638A1 (en) | 2003-12-08 | 2005-06-09 | Swayze Eric E. | Benzimidazoles and analogs thereof as antivirals |
| US20110009403A1 (en) | 2007-10-05 | 2011-01-13 | S*Bio Pte Ltd. | 2-morpholinylpurines as inhibitors of pi3k |
| CN101717397B (zh) | 2008-10-09 | 2012-11-28 | 中国科学院上海药物研究所 | 一类取代吡啶并[2',1':2,3]咪唑并[4,5-c]异喹啉酮类化合物及其合成方法和用途,以及包含该类化合物的药物组合物 |
| US8691187B2 (en) | 2009-03-23 | 2014-04-08 | Eli Lilly And Company | Imaging agents for detecting neurological disorders |
| WO2012148550A1 (en) | 2011-02-25 | 2012-11-01 | Myrexis, Inc. | Prodrugs of therapeutic compounds |
| EP2527344A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Pyridin-2(1H)-one derivatives useful as medicaments for the treatment of myeloproliferative disorders, transplant rejection, immune-mediated and inflammatory diseases |
| WO2013186229A1 (en) | 2012-06-11 | 2013-12-19 | Ucb Pharma S.A. | Tnf -alpha modulating benzimidazoles |
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| EP2872508B1 (en) | 2012-07-13 | 2018-08-29 | UCB Biopharma SPRL | Imidazopyridine derivatives as modulators of tnf activity |
| WO2014072261A1 (en) * | 2012-11-07 | 2014-05-15 | F. Hoffmann-La Roche Ag | Triazolo compounds |
| ES2529865B8 (es) * | 2013-07-25 | 2016-01-22 | Fundación Para La Investigación Biomédica Del Hospital Universitario La Paz (Fibhulp) | USO DE COMPUESTOS DERIVADOS DE SALES DE PIRIDAZINO[1',6':1,2]PIRIDO[3,4-b]INDOLINIO COMO AGENTES ANTIINFLAMATORIOS |
| GB201321742D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| GB201321746D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
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| GB201321741D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| JP6469692B2 (ja) | 2013-12-09 | 2019-02-13 | ユーシービー バイオファルマ エスピーアールエル | Ｔｎｆ活性のモジュレーターとしてのイミダゾピリジン誘導体 |
| GB201321743D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| GB201321745D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| RU2685234C1 (ru) | 2013-12-09 | 2019-04-17 | Юсб Байофарма Спрл | Конденсированные бициклические гетероароматические производные в качестве модуляторов активности tnf |
| TW201629063A (zh) | 2014-10-06 | 2016-08-16 | 標誌製藥公司 | 經取代胺基嘌呤化合物、其組合物及用其之治療方法 |
| AU2016233288A1 (en) | 2015-03-18 | 2017-11-09 | Bristol-Myers Squibb Company | Substituted tricyclic heterocyclic compounds |
| BR112017019605A2 (pt) | 2015-03-18 | 2018-05-08 | Bristol-Myers Squibb Company | compostos heterocíclicos úteis como inibidores de tnf |
| AR104291A1 (es) * | 2015-04-17 | 2017-07-12 | Abbvie Inc | Moduladores tricíclicos de la señalización por tnf |
| JP2018517683A (ja) * | 2015-05-04 | 2018-07-05 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | 三環式ピペリジン化合物 |
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2016
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- 2016-03-17 SG SG11201707471RA patent/SG11201707471RA/en unknown
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- 2016-03-17 KR KR1020177029450A patent/KR102630010B1/ko active Active
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- 2017-09-15 IL IL254520A patent/IL254520A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2797685T3 (es) | 2020-12-03 |
| CN107635992B (zh) | 2020-05-22 |
| AU2016233289A1 (en) | 2017-11-09 |
| EP3271361A1 (en) | 2018-01-24 |
| JP6793658B2 (ja) | 2020-12-02 |
| EP3271361B1 (en) | 2020-04-22 |
| EA201792025A1 (ru) | 2018-01-31 |
| CN107635992A (zh) | 2018-01-26 |
| JP2018508554A (ja) | 2018-03-29 |
| WO2016149437A1 (en) | 2016-09-22 |
| US10308652B2 (en) | 2019-06-04 |
| US20180111937A1 (en) | 2018-04-26 |
| EA032314B1 (ru) | 2019-05-31 |
| IL254520A0 (en) | 2017-11-30 |
| KR20170129811A (ko) | 2017-11-27 |
| BR112017019731A2 (pt) | 2018-05-22 |
| KR102630010B1 (ko) | 2024-01-25 |
| MX2017011433A (es) | 2017-11-10 |
| SG11201707471RA (en) | 2017-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20220301 |