JP2018508554A5 - - Google Patents
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- Publication number
- JP2018508554A5 JP2018508554A5 JP2017549093A JP2017549093A JP2018508554A5 JP 2018508554 A5 JP2018508554 A5 JP 2018508554A5 JP 2017549093 A JP2017549093 A JP 2017549093A JP 2017549093 A JP2017549093 A JP 2017549093A JP 2018508554 A5 JP2018508554 A5 JP 2018508554A5
- Authority
- JP
- Japan
- Prior art keywords
- phenyl
- imidazo
- substituted
- pyridazin
- alkyl
- 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
Links
- -1 -OH Chemical group 0.000 claims 60
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 38
- 125000003118 aryl group Chemical group 0.000 claims 38
- 125000000623 heterocyclic group Chemical group 0.000 claims 34
- 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 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 14
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 150000001875 compounds Chemical class 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 125000002950 monocyclic group Chemical group 0.000 claims 10
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims 8
- 229910052799 carbon Inorganic materials 0.000 claims 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 6
- 125000005843 halogen group Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- 125000006620 amino-(C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000004452 carbocyclyl group Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000004076 pyridyl group Chemical group 0.000 claims 3
- 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
- YGHANWAHRPLDGU-UHFFFAOYSA-N 3-[2-(difluoromethoxy)phenyl]-12-[2-(2-hydroxypropan-2-yl)pyrimidin-5-yl]-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)C1NCC(C=2N=C3N(N=C(C=C3)C=3C=NC(=NC=3)C(C)(C)O)C=21)O)F YGHANWAHRPLDGU-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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- PVGRKMIQXBGYQF-UHFFFAOYSA-N [4-[3-[2-(difluoromethoxy)phenyl]-6-hydroxy-1,4,8,13-tetrazatricyclo[7.4.0.02,7]trideca-2(7),8,10,12-tetraen-12-yl]phenyl]-morpholin-4-ylmethanone Chemical compound FC(OC1=C(C=CC=C1)C1NCC(C=2N=C3N(N=C(C=C3)C3=CC=C(C=C3)C(=O)N3CCOCC3)C=21)O)F PVGRKMIQXBGYQF-UHFFFAOYSA-N 0.000 claims 2
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- XAMUDJHXFNRLCY-UHFFFAOYSA-N phenthoate Chemical compound CCOC(=O)C(SP(=S)(OC)OC)C1=CC=CC=C1 XAMUDJHXFNRLCY-UHFFFAOYSA-N 0.000 claims 2
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl 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
- 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
- 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
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 108060008683 Tumor Necrosis Factor Receptor Proteins 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 125000005001 aminoaryl group Chemical group 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
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 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
- 125000004428 fluoroalkoxy group Chemical group 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
- UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims 1
- VTVRXITWWZGKHV-UHFFFAOYSA-N imidazo[1,2-b]pyridazine Chemical compound N1=CC=CC2=NC=CN21 VTVRXITWWZGKHV-UHFFFAOYSA-N 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 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
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 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
- IBBMAWULFFBRKK-UHFFFAOYSA-N picolinamide Chemical compound NC(=O)C1=CC=CC=N1 IBBMAWULFFBRKK-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
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 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
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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 |
|---|---|---|---|
| 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 (3)
| Publication Number | Publication Date |
|---|---|
| JP2018508554A JP2018508554A (ja) | 2018-03-29 |
| JP2018508554A5 true JP2018508554A5 (enExample) | 2019-04-25 |
| JP6793658B2 JP6793658B2 (ja) | 2020-12-02 |
Family
ID=55640933
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017549093A Active JP6793658B2 (ja) | 2015-03-18 | 2016-03-17 | Ｔｎｆ阻害剤として有用な三環式ヘテロ環式化合物 |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US10308652B2 (enExample) |
| EP (1) | EP3271361B1 (enExample) |
| JP (1) | JP6793658B2 (enExample) |
| KR (1) | KR102630010B1 (enExample) |
| CN (1) | CN107635992B (enExample) |
| AU (1) | AU2016233289A1 (enExample) |
| BR (1) | BR112017019731A2 (enExample) |
| CA (1) | CA2982446A1 (enExample) |
| EA (1) | EA032314B1 (enExample) |
| ES (1) | ES2797685T3 (enExample) |
| IL (1) | IL254520A0 (enExample) |
| MX (1) | MX2017011433A (enExample) |
| SG (1) | SG11201707471RA (enExample) |
| WO (1) | WO2016149437A1 (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG11201707469WA (en) | 2015-03-18 | 2017-10-30 | Bristol Myers Squibb Co | Substituted tricyclic heterocyclic compounds |
| ES2803650T3 (es) | 2015-03-18 | 2021-01-28 | Bristol Myers Squibb Co | Compuestos heterocíclicos útiles como inhibidores de TNF |
| TW201706258A (zh) | 2015-04-17 | 2017-02-16 | 艾伯維有限公司 | 作為ｔｎｆ信號傳遞調節劑之吲唑酮 |
| AR104291A1 (es) | 2015-04-17 | 2017-07-12 | Abbvie Inc | Moduladores tricíclicos de la señalización por tnf |
| TW201702247A (zh) | 2015-04-17 | 2017-01-16 | 艾伯維有限公司 | 作為ｔｎｆ信號傳遞調節劑之吲唑酮 |
| GB201510758D0 (en) | 2015-06-18 | 2015-08-05 | Ucb Biopharma Sprl | Novel TNFa structure for use in therapy |
| AU2016301215A1 (en) | 2015-08-03 | 2018-03-22 | 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 |
Family Cites Families (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4391806A (en) * | 1982-07-12 | 1983-07-05 | The Dow Chemical Company | Substituted tetrahydropyridazino-(1,6-A)benzimidazoles and use as bronchodilators |
| JP2001513084A (ja) | 1997-02-25 | 2001-08-28 | ザ ガバメント オブ ザ ユナイテッド ステーツ オブ アメリカ，レプリゼンテッド バイ ザ セクレタリー，デパートメント オブ ヘルス アンド ヒューマン サービシズ | 逆転写酵素の非ヌクレオシド阻害剤としての置換ベンズイミダゾール |
| EP1224185B1 (en) * | 1999-10-27 | 2005-11-30 | Novartis AG | Thiazole and imidazo[4,5-b]pyridine compounds and their pharmaceutical use |
| 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 |
| AU2003298839A1 (en) | 2002-12-03 | 2004-06-23 | 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 |
| CN104428293B (zh) | 2012-06-11 | 2018-06-08 | Ucb生物制药私人有限公司 | 调节TNFα的苯并咪唑类 |
| GB201212513D0 (en) | 2012-07-13 | 2012-08-29 | Ucb Pharma Sa | Therapeutic agents |
| BR112015000675B1 (pt) | 2012-07-13 | 2022-07-12 | UCB Biopharma SRL | Derivados de imidazopiridina como moduladores da atividade de tnf |
| KR20150081354A (ko) * | 2012-11-07 | 2015-07-13 | 에프. 호프만-라 로슈 아게 | 트라이아졸로 화합물 |
| 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 |
| CN105814022B (zh) | 2013-12-09 | 2018-09-28 | Ucb生物制药私人有限公司 | 作为tnf活性调节剂的稠合的二环杂芳族衍生物 |
| GB201321737D0 (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 |
| GB201321746D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| GB201321744D0 (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 |
| 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 |
| GB201321741D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic agents |
| GB201321735D0 (en) | 2013-12-09 | 2014-01-22 | Ucb Pharma Sa | Therapeutic Agents |
| GB201321742D0 (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 |
| EA201790779A1 (ru) | 2014-10-06 | 2017-09-29 | СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Замещенные аминопуриновые соединения, их композиции и способы лечения с использованием таких соединений |
| ES2803650T3 (es) | 2015-03-18 | 2021-01-28 | Bristol Myers Squibb Co | Compuestos heterocíclicos útiles como inhibidores de TNF |
| SG11201707469WA (en) | 2015-03-18 | 2017-10-30 | Bristol Myers Squibb Co | Substituted tricyclic heterocyclic compounds |
| AR104291A1 (es) * | 2015-04-17 | 2017-07-12 | Abbvie Inc | Moduladores tricíclicos de la señalización por tnf |
| EP3292127A1 (en) * | 2015-05-04 | 2018-03-14 | Actelion Pharmaceuticals Ltd | Tricyclic piperidine compounds |
-
2016
- 2016-03-17 US US15/558,708 patent/US10308652B2/en active Active
- 2016-03-17 CA CA2982446A patent/CA2982446A1/en not_active Abandoned
- 2016-03-17 SG SG11201707471RA patent/SG11201707471RA/en unknown
- 2016-03-17 EP EP16712646.5A patent/EP3271361B1/en active Active
- 2016-03-17 BR BR112017019731-6A patent/BR112017019731A2/pt not_active Application Discontinuation
- 2016-03-17 JP JP2017549093A patent/JP6793658B2/ja active Active
- 2016-03-17 WO PCT/US2016/022738 patent/WO2016149437A1/en not_active Ceased
- 2016-03-17 ES ES16712646T patent/ES2797685T3/es active Active
- 2016-03-17 KR KR1020177029450A patent/KR102630010B1/ko active Active
- 2016-03-17 AU AU2016233289A patent/AU2016233289A1/en not_active Abandoned
- 2016-03-17 EA EA201792025A patent/EA032314B1/ru not_active IP Right Cessation
- 2016-03-17 CN CN201680025154.3A patent/CN107635992B/zh active Active
- 2016-03-17 MX MX2017011433A patent/MX2017011433A/es unknown
-
2017
- 2017-09-15 IL IL254520A patent/IL254520A0/en unknown
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