JP2018508553A5 - - Google Patents
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- Publication number
- JP2018508553A5 JP2018508553A5 JP2017549092A JP2017549092A JP2018508553A5 JP 2018508553 A5 JP2018508553 A5 JP 2018508553A5 JP 2017549092 A JP2017549092 A JP 2017549092A JP 2017549092 A JP2017549092 A JP 2017549092A JP 2018508553 A5 JP2018508553 A5 JP 2018508553A5
- Authority
- JP
- Japan
- Prior art keywords
- substituted
- alkyl
- phenyl
- pyrrolo
- imidazo
- 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.)
- Granted
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- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 39
- 125000003118 aryl group Chemical group 0.000 claims 36
- 125000000623 heterocyclic group Chemical group 0.000 claims 36
- -1 -OH Chemical group 0.000 claims 26
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- ZVWSNJQNGVRIGG-UHFFFAOYSA-N N=1C=NC2=NC=C(CC2=1)O Chemical compound N=1C=NC2=NC=C(CC2=1)O ZVWSNJQNGVRIGG-UHFFFAOYSA-N 0.000 claims 10
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 7
- 125000004452 carbocyclyl group Chemical group 0.000 claims 7
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 7
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- GAMYYCRTACQSBR-UHFFFAOYSA-N 4-azabenzimidazole Chemical compound C1=CC=C2NC=NC2=N1 GAMYYCRTACQSBR-UHFFFAOYSA-N 0.000 claims 5
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 3
- VKRVXXGHKNLUEU-UHFFFAOYSA-N 3-[2-fluoro-6-(trifluoromethyl)phenyl]-11-[4-(2-hydroxypropan-2-yl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)O VKRVXXGHKNLUEU-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- MWYJODZWNRUGPZ-HXUWFJFHSA-N (3R)-3-(2,5-dimethylphenyl)-11-(6-methoxypyridin-3-yl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraene Chemical compound CC1=C(C=C(C=C1)C)[C@H]1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=CC=3)OC)N21 MWYJODZWNRUGPZ-HXUWFJFHSA-N 0.000 claims 2
- JBBNVIMXSSPSFU-UHFFFAOYSA-N 11-[4-(2-hydroxypropan-2-yl)phenyl]-3-[2-methyl-5-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound OC(C)(C)C1=CC=C(C=C1)C1=CC=C2C(=N1)N1C(=N2)C(CC1C1=C(C=CC(=C1)C(F)(F)F)C)O JBBNVIMXSSPSFU-UHFFFAOYSA-N 0.000 claims 2
- CCYYYKOUISBKNQ-HSZRJFAPSA-N 2-[4-[(3R)-3-(2,5-dimethylphenyl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound CC1=C(C=C(C=C1)C)[C@H]1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21 CCYYYKOUISBKNQ-HSZRJFAPSA-N 0.000 claims 2
- DCQCGNMFCGZMGL-UHFFFAOYSA-N 2-[4-[3-(2-cyclopropylphenyl)-5-fluoro-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound C1(CC1)C1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)F DCQCGNMFCGZMGL-UHFFFAOYSA-N 0.000 claims 2
- LWOODTYOEVZSQK-UHFFFAOYSA-N 2-[4-[3-[2-fluoro-6-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1=C(C(=CC=C1)C(F)(F)F)C1CCC2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21 LWOODTYOEVZSQK-UHFFFAOYSA-N 0.000 claims 2
- MQHNRCXLKUUPKQ-UHFFFAOYSA-N 2-[4-[5-fluoro-3-[2-(trifluoromethoxy)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1CC(N2C1=NC=1C2=NC(=CC=1)C1=CC=C(C=C1)C(C)(C)O)C1=C(C=CC=C1)OC(F)(F)F MQHNRCXLKUUPKQ-UHFFFAOYSA-N 0.000 claims 2
- AQHQIKSWRGMNJB-UHFFFAOYSA-N 2-[4-[5-fluoro-3-[2-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1CC(N2C1=NC=1C2=NC(=CC=1)C1=CC=C(C=C1)C(C)(C)O)C1=C(C=CC=C1)C(F)(F)F AQHQIKSWRGMNJB-UHFFFAOYSA-N 0.000 claims 2
- JKYSVRSGDRBSCA-UHFFFAOYSA-N 2-[4-[5-fluoro-3-[5-fluoro-2-(trifluoromethyl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]phenyl]propan-2-ol Chemical compound FC1CC(N2C1=NC=1C2=NC(=CC=1)C1=CC=C(C=C1)C(C)(C)O)C1=C(C=CC(=C1)F)C(F)(F)F JKYSVRSGDRBSCA-UHFFFAOYSA-N 0.000 claims 2
- UCDQWLXDJQLDLC-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-11-(2-morpholin-4-ylpyrimidin-5-yl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)N3CCOCC3)N21)O)F UCDQWLXDJQLDLC-UHFFFAOYSA-N 0.000 claims 2
- YWGVUJDGXZCYRX-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-11-(6-methoxypyridin-3-yl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraene Chemical compound FC(OC1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=CC=3)OC)N21)F YWGVUJDGXZCYRX-UHFFFAOYSA-N 0.000 claims 2
- JIZHFNUDERURSW-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-11-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)C(C)(C)O)N21)O)F JIZHFNUDERURSW-UHFFFAOYSA-N 0.000 claims 2
- HWQNCQBWUJAXRI-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-11-[4-(2-hydroxypropan-2-yl)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-5-ol Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C3=CC=C(C=C3)C(C)(C)O)N21)O)F HWQNCQBWUJAXRI-UHFFFAOYSA-N 0.000 claims 2
- ADAXWDOUMNIZCT-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-5-fluoro-11-(6-methoxypyridin-3-yl)-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraene Chemical compound FC(OC1=C(C=CC=C1)C1CC(C2=NC=3C(=NC(=CC=3)C=3C=NC(=CC=3)OC)N21)F)F ADAXWDOUMNIZCT-UHFFFAOYSA-N 0.000 claims 2
- GALYFDYKAMGDGH-UHFFFAOYSA-N 4-[5-[3-[2-(difluoromethoxy)phenyl]-2,7,12-triazatricyclo[6.4.0.02,6]dodeca-1(8),6,9,11-tetraen-11-yl]pyrimidin-2-yl]morpholine Chemical compound FC(OC1=C(C=CC=C1)C1CCC2=NC=3C(=NC(=CC=3)C=3C=NC(=NC=3)N3CCOCC3)N21)F GALYFDYKAMGDGH-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- 208000026326 Adult-onset Still disease Diseases 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 206010016207 Familial Mediterranean fever Diseases 0.000 claims 1
- 206010018634 Gouty Arthritis Diseases 0.000 claims 1
- 208000009329 Graft vs Host Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000005777 Lupus Nephritis Diseases 0.000 claims 1
- 102100022691 NACHT, LRR and PYD domains-containing protein 3 Human genes 0.000 claims 1
- 101710126825 NACHT, LRR and PYD domains-containing protein 3 Proteins 0.000 claims 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims 1
- 125000005001 aminoaryl group Chemical group 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 208000004296 neuralgia Diseases 0.000 claims 1
- 208000021722 neuropathic pain Diseases 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 230000000737 periodic effect Effects 0.000 claims 1
- 208000025487 periodic fever syndrome Diseases 0.000 claims 1
- PSBAIJVSCTZDDB-UHFFFAOYSA-N phenyl acetylsalicylate Chemical compound CC(=O)OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 PSBAIJVSCTZDDB-UHFFFAOYSA-N 0.000 claims 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 208000020408 systemic-onset juvenile idiopathic arthritis Diseases 0.000 claims 1
- 102000003298 tumor necrosis factor receptor Human genes 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562134769P | 2015-03-18 | 2015-03-18 | |
| US62/134,769 | 2015-03-18 | ||
| PCT/US2016/022737 WO2016149436A1 (en) | 2015-03-18 | 2016-03-17 | Substituted tricyclic heterocyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018508553A JP2018508553A (ja) | 2018-03-29 |
| JP2018508553A5 true JP2018508553A5 (cg-RX-API-DMAC7.html) | 2019-04-25 |
| JP6793657B2 JP6793657B2 (ja) | 2020-12-02 |
Family
ID=55640932
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017549092A Active JP6793657B2 (ja) | 2015-03-18 | 2016-03-17 | 置換三環式ヘテロ環式化合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10189840B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP3271360B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP6793657B2 (cg-RX-API-DMAC7.html) |
| KR (1) | KR102654709B1 (cg-RX-API-DMAC7.html) |
| CN (1) | CN107635993B (cg-RX-API-DMAC7.html) |
| AU (1) | AU2016233288A1 (cg-RX-API-DMAC7.html) |
| BR (1) | BR112017019773A2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA2980159A1 (cg-RX-API-DMAC7.html) |
| EA (1) | EA032315B1 (cg-RX-API-DMAC7.html) |
| ES (1) | ES2797805T3 (cg-RX-API-DMAC7.html) |
| IL (1) | IL254424A0 (cg-RX-API-DMAC7.html) |
| MX (1) | MX2017011434A (cg-RX-API-DMAC7.html) |
| SG (1) | SG11201707469WA (cg-RX-API-DMAC7.html) |
| WO (1) | WO2016149436A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102630010B1 (ko) | 2015-03-18 | 2024-01-25 | 브리스톨-마이어스 스큅 컴퍼니 | Tnf의 억제제로서 유용한 트리시클릭 헤테로시클릭 화합물 |
| KR102696304B1 (ko) | 2015-03-18 | 2024-08-16 | 브리스톨-마이어스 스큅 컴퍼니 | Tnf의 억제제로서 유용한 헤테로시클릭 화합물 |
| WO2016168638A1 (en) | 2015-04-17 | 2016-10-20 | Abbvie Inc. | Indazolones as modulators of tnf signaling |
| WO2016168641A1 (en) | 2015-04-17 | 2016-10-20 | Abbvie Inc. | Tricyclic modulators of tnf signaling |
| UY36629A (es) | 2015-04-17 | 2016-11-30 | Abbvie Inc | Indazolonas como moduladores de la señalización de tnf |
| GB201510758D0 (en) | 2015-06-18 | 2015-08-05 | Ucb Biopharma Sprl | Novel TNFa structure for use in therapy |
| CA2994703A1 (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 |
| JP7121033B2 (ja) * | 2017-03-15 | 2022-08-17 | ユーシービー バイオファルマ エスアールエル | Ｔｎｆ活性のモジュレーターとしての縮合五環式イミダゾール誘導体 |
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| DE69814049T2 (de) | 1997-02-25 | 2004-02-19 | The Government of the United States of America, as represented by the Secretary National Institute of Health, Office of Technology Transfer | Substituierte benzimidazole als nicht-nucleoside reverse transcriptase inhibitore |
| ES2254238T3 (es) * | 1999-10-27 | 2006-06-16 | Novartis Ag | Compuestos de tiazol e imidazo(4,5-b)piridina y su uso farmaceutico. |
| US7601846B2 (en) | 2001-06-26 | 2009-10-13 | The Regents Of The University Of California | Compounds having activity as inhibitors of apoptosis |
| WO2003064422A1 (en) | 2002-01-31 | 2003-08-07 | Daiichi Pharmaceutical Co., Ltd. | IMIDAZO[1,2-a]PYRIDINE DERIVATIVE |
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| WO2009000412A1 (en) * | 2007-06-26 | 2008-12-31 | Sanofi Aventis | A regioselective metal catalyzed synthesis of annelated benzimidazoles and azabenzimidazoles |
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| GB201321735D0 (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 |
| GB201321739D0 (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 |
| GB201321738D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| WO2015086523A1 (en) | 2013-12-09 | 2015-06-18 | Ucb Biopharma Sprl | Fused bicyclic heteroaromatic derivatives as modulators of tnf activity |
| ES2809535T3 (es) | 2013-12-09 | 2021-03-04 | UCB Biopharma SRL | Derivados de imidazopiridina como moduladores de la actividad de TNF |
| ES2980464T3 (es) | 2014-10-06 | 2024-10-01 | Signal Pharm Llc | Productos intermedios sintéticos útiles para preparar compuestos de aminopurina sustituidos |
| KR102696304B1 (ko) | 2015-03-18 | 2024-08-16 | 브리스톨-마이어스 스큅 컴퍼니 | Tnf의 억제제로서 유용한 헤테로시클릭 화합물 |
| KR102630010B1 (ko) | 2015-03-18 | 2024-01-25 | 브리스톨-마이어스 스큅 컴퍼니 | Tnf의 억제제로서 유용한 트리시클릭 헤테로시클릭 화합물 |
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2016
- 2016-03-17 CA CA2980159A patent/CA2980159A1/en not_active Abandoned
- 2016-03-17 EA EA201792034A patent/EA032315B1/ru not_active IP Right Cessation
- 2016-03-17 US US15/558,692 patent/US10189840B2/en active Active
- 2016-03-17 SG SG11201707469WA patent/SG11201707469WA/en unknown
- 2016-03-17 MX MX2017011434A patent/MX2017011434A/es unknown
- 2016-03-17 KR KR1020177029449A patent/KR102654709B1/ko active Active
- 2016-03-17 BR BR112017019773-1A patent/BR112017019773A2/pt not_active Application Discontinuation
- 2016-03-17 JP JP2017549092A patent/JP6793657B2/ja active Active
- 2016-03-17 CN CN201680026733.XA patent/CN107635993B/zh active Active
- 2016-03-17 ES ES16712645T patent/ES2797805T3/es active Active
- 2016-03-17 WO PCT/US2016/022737 patent/WO2016149436A1/en not_active Ceased
- 2016-03-17 EP EP16712645.7A patent/EP3271360B1/en active Active
- 2016-03-17 AU AU2016233288A patent/AU2016233288A1/en not_active Abandoned
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2017
- 2017-09-11 IL IL254424A patent/IL254424A0/en unknown