JP2018524331A5 - - Google Patents
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- Publication number
- JP2018524331A5 JP2018524331A5 JP2017566812A JP2017566812A JP2018524331A5 JP 2018524331 A5 JP2018524331 A5 JP 2018524331A5 JP 2017566812 A JP2017566812 A JP 2017566812A JP 2017566812 A JP2017566812 A JP 2017566812A JP 2018524331 A5 JP2018524331 A5 JP 2018524331A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- alkyl
- carbonitrile
- compound
- 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
Links
- -1 imidazo [1,2-b] pyridazinyl Chemical group 0.000 claims 37
- 150000001875 compounds Chemical class 0.000 claims 20
- 125000000217 alkyl group Chemical group 0.000 claims 16
- OAQFIXDKTZYDRL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound N=1C=CN2N=CC(=CC2=1)C#N OAQFIXDKTZYDRL-UHFFFAOYSA-N 0.000 claims 14
- 125000001072 heteroaryl group Chemical group 0.000 claims 13
- 150000003839 salts Chemical class 0.000 claims 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims 9
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 9
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000003566 oxetanyl group Chemical group 0.000 claims 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 6
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- 125000001425 triazolyl group Chemical group 0.000 claims 5
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 4
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 4
- NUKYPUAOHBNCPY-UHFFFAOYSA-N 4-aminopyridine Chemical compound NC1=CC=NC=C1 NUKYPUAOHBNCPY-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 4
- 125000002883 imidazolyl group Chemical group 0.000 claims 4
- CAJZIMCVNPNPSW-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound C1=C(C#N)C=NC2=CC=NN21 CAJZIMCVNPNPSW-UHFFFAOYSA-N 0.000 claims 4
- ZIEWSZYVEDTXGH-UHFFFAOYSA-N pyrimidine-4-carbonitrile Chemical compound N#CC1=CC=NC=N1 ZIEWSZYVEDTXGH-UHFFFAOYSA-N 0.000 claims 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 4
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 3
- 238000002560 therapeutic procedure Methods 0.000 claims 3
- DOTOFFAVTNZRLB-UHFFFAOYSA-N 2-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-N-cyclopropyl-5-(1-propyltriazol-4-yl)pyridin-4-amine Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=NC=C(C(=C1)NC1CC1)C=1N=NN(C=1)CCC DOTOFFAVTNZRLB-UHFFFAOYSA-N 0.000 claims 2
- ZBRIPMUNBFXCSD-UHFFFAOYSA-N 2-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-N-propan-2-yl-5-(1-propyltriazol-4-yl)pyridin-4-amine Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=NC=C(C(=C1)NC(C)C)C=1N=NN(C=1)CCC ZBRIPMUNBFXCSD-UHFFFAOYSA-N 0.000 claims 2
- KFILYRVIDVXHNI-UHFFFAOYSA-N 2-(7-chloroimidazo[1,2-b]pyridazin-3-yl)-N-propan-2-yl-5-[1-(2,2,2-trifluoroethyl)pyrazol-4-yl]pyridin-4-amine Chemical compound ClC1=CC=2N(N=C1)C(=CN=2)C1=NC=C(C(=C1)NC(C)C)C=1C=NN(C=1)CC(F)(F)F KFILYRVIDVXHNI-UHFFFAOYSA-N 0.000 claims 2
- JDHXZJLBUNAELN-UHFFFAOYSA-N 3-[4-(cyclopropylamino)-5-(1-propyltriazol-4-yl)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound C1(CC1)NC1=CC(=NC=C1C=1N=NN(C=1)CCC)C1=CN=C2N1N=CC(=C2)C#N JDHXZJLBUNAELN-UHFFFAOYSA-N 0.000 claims 2
- FRYFNOMIOVBKEM-UHFFFAOYSA-N 3-[4-[(3,3-difluorocyclobutyl)amino]-5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]pyridin-2-yl]pyrazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound FC1(CC(C1)NC1=CC(=NC=C1N1N=NC(=C1)CCC(C)(C)O)C=1C=NN2C=1N=CC(=C2)C#N)F FRYFNOMIOVBKEM-UHFFFAOYSA-N 0.000 claims 2
- FXJWDSCIKROGLP-UHFFFAOYSA-N 3-[5-[1-(1-acetylazetidin-3-yl)triazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound C(C)(=O)N1CC(C1)N1N=NC(=C1)C=1C(=CC(=NC=1)C1=CN=C2N1N=CC(=C2)C#N)NC(C)C FXJWDSCIKROGLP-UHFFFAOYSA-N 0.000 claims 2
- XOYXADDAQJVPEI-UHFFFAOYSA-N 3-[5-[1-(3-hydroxy-3-methylbutyl)pyrazol-4-yl]-4-(propan-2-ylamino)pyridin-2-yl]imidazo[1,2-b]pyridazine-7-carbonitrile Chemical compound OC(CCN1N=CC(=C1)C=1C(=CC(=NC=1)C1=CN=C2N1N=CC(=C2)C#N)NC(C)C)(C)C XOYXADDAQJVPEI-UHFFFAOYSA-N 0.000 claims 2
- PYJGADHQKPQSHH-UHFFFAOYSA-N 3-[5-[4-(3-hydroxy-3-methylbutyl)triazol-1-yl]-4-(oxetan-3-ylamino)pyridin-2-yl]pyrazolo[1,5-a]pyrimidine-6-carbonitrile Chemical compound OC(CCC=1N=NN(C=1)C=1C(=CC(=NC=1)C=1C=NN2C=1N=CC(=C2)C#N)NC1COC1)(C)C PYJGADHQKPQSHH-UHFFFAOYSA-N 0.000 claims 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 2
- 201000005569 Gout Diseases 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 2
- 229960004979 fampridine Drugs 0.000 claims 2
- 206010025135 lupus erythematosus Diseases 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 230000000737 periodic effect Effects 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- WAGVYTPQQZVQJF-UHFFFAOYSA-N 1-(oxan-4-yl)pyrazole Chemical compound C1COCCC1N1N=CC=C1 WAGVYTPQQZVQJF-UHFFFAOYSA-N 0.000 claims 1
- FLCAFSOTMLXPPX-UHFFFAOYSA-N 7-chloroimidazo[1,2-b]pyridazine Chemical compound C1=C(Cl)C=NN2C=CN=C21 FLCAFSOTMLXPPX-UHFFFAOYSA-N 0.000 claims 1
- 208000026326 Adult-onset Still disease Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 208000023328 Basedow disease Diseases 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 235000010650 Hyssopus officinalis Nutrition 0.000 claims 1
- 240000001812 Hyssopus officinalis Species 0.000 claims 1
- 208000003456 Juvenile Arthritis 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
- 206010028980 Neoplasm 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
- 208000006673 asthma Diseases 0.000 claims 1
- 201000011510 cancer Diseases 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
- 239000003937 drug carrier Substances 0.000 claims 1
- 208000024908 graft versus host disease Diseases 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 201000002215 juvenile rheumatoid arthritis Diseases 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
- 206010039073 rheumatoid 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 |
|---|---|---|---|
| IN1880DE2015 | 2015-06-24 | ||
| IN1880/DEL/2015 | 2015-06-24 | ||
| PCT/US2016/038862 WO2016210037A1 (en) | 2015-06-24 | 2016-06-23 | Heteroaryl substituted aminopyridine compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018524331A JP2018524331A (ja) | 2018-08-30 |
| JP2018524331A5 true JP2018524331A5 (enExample) | 2019-07-18 |
| JP6720225B2 JP6720225B2 (ja) | 2020-07-08 |
Family
ID=56345252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017566812A Active JP6720225B2 (ja) | 2015-06-24 | 2016-06-23 | ヘテロアリール置換のアミノピリジン化合物 |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US10202390B2 (enExample) |
| EP (1) | EP3313844B1 (enExample) |
| JP (1) | JP6720225B2 (enExample) |
| CN (1) | CN108026099B (enExample) |
| AR (1) | AR105114A1 (enExample) |
| ES (1) | ES2822956T3 (enExample) |
| TW (1) | TW201713663A (enExample) |
| UY (1) | UY36747A (enExample) |
| WO (1) | WO2016210037A1 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR105113A1 (es) * | 2015-06-24 | 2017-09-06 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituida con heteroarilo |
| UY36747A (es) | 2015-06-24 | 2016-12-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de aminopiridina sustituida con heteroarilo como inhibidores de quinasa y modulantes de irak-4 y composiciones farmacéuticas que los contienen |
| US10618903B2 (en) * | 2015-06-24 | 2020-04-14 | Bristol-Myers Squibb Company | Heteroaryl substituted aminopyridine compounds |
| JOP20180011A1 (ar) | 2017-02-16 | 2019-01-30 | Gilead Sciences Inc | مشتقات بيرولو [1، 2-b]بيريدازين |
| MY200228A (en) | 2017-05-11 | 2023-12-15 | Bristol Myers Squibb Co | Thienopyridines and benzothiophenes useful as irak4 inhibitors |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| TWI721483B (zh) | 2018-07-13 | 2021-03-11 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| EP3837012A1 (en) | 2018-08-13 | 2021-06-23 | Gilead Sciences, Inc. | Pyrrolo[1,2-b]pyridazine derivatives as irak4 inhibitors |
| CN112533924B (zh) * | 2018-08-13 | 2023-11-28 | 吉利德科学公司 | 作为IRAK4抑制剂的吡咯并[1,2-b]哒嗪衍生物 |
| TWI727392B (zh) | 2018-08-13 | 2021-05-11 | 美商基利科學股份有限公司 | 噻二唑irak4抑制劑 |
| WO2021011724A1 (en) | 2019-07-18 | 2021-01-21 | Bristol-Myers Squibb Company | Tricyclic heteroaryl compounds useful as irak4 inhibitors |
| WO2021011727A1 (en) * | 2019-07-18 | 2021-01-21 | Bristol-Myers Squibb Company | PYRAZOLO[3,4-d]PYRROLO[1,2-b]PYRIDAZINYL COMPOUNDS USEFUL AS IRAK4 INHIBITORS |
| JP7573596B2 (ja) * | 2019-07-23 | 2024-10-25 | ブリストル－マイヤーズ スクイブ カンパニー | Ｉｒａｋ４阻害剤として有用なチエノピリジニルおよびチアゾロピリジニル化合物 |
| CN114174279B (zh) | 2019-08-06 | 2024-07-02 | 百时美施贵宝公司 | 可用作irak4抑制剂的双环杂环化合物 |
| US12570659B2 (en) | 2019-08-13 | 2026-03-10 | Bristol-Myers Squibb Company | Bicyclic heteroaryl compounds useful as IRAK4 inhibitors |
| CN115335380B (zh) | 2020-02-03 | 2024-08-02 | 百时美施贵宝公司 | 可用作irak4抑制剂的三环杂芳基化合物 |
| US12391702B2 (en) | 2020-02-03 | 2025-08-19 | Bristol-Myers Squibb Company | Benzo[5,6][1,4]dioxino[2,3-b]pyridine compounds useful as IRAK4 inhibitors |
| US12528814B2 (en) | 2020-02-19 | 2026-01-20 | Nurix Therapeutics, Inc. | Bifunctional degraders of interleukin-1 receptor-associated kinases and therapeutic use thereof |
| CN113149995A (zh) * | 2021-03-31 | 2021-07-23 | 安徽驱石医药科技有限公司 | 一种7-氟吡唑并[1,2-b]吡嗪-4-甲腈的合成方法及应用 |
| WO2023023255A1 (en) | 2021-08-18 | 2023-02-23 | Nurix Therapeutics, Inc. | Bifunctional degraders of interleukin-1 receptor-associated kinases and therapeutic use thereof |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6825190B2 (en) | 2001-06-15 | 2004-11-30 | Vertex Pharmaceuticals Incorporated | Protein kinase inhibitors and uses thereof |
| AUPR688101A0 (en) | 2001-08-08 | 2001-08-30 | Luminis Pty Limited | Protein domains and their ligands |
| GB0211019D0 (en) | 2002-05-14 | 2002-06-26 | Syngenta Ltd | Novel compounds |
| JP4529685B2 (ja) | 2002-06-28 | 2010-08-25 | アステラス製薬株式会社 | ジアミノピリミジンカルボキサミド誘導体 |
| JP2006516561A (ja) | 2003-01-17 | 2006-07-06 | ワーナー−ランバート・カンパニー、リミテッド、ライアビリティ、カンパニー | 細胞増殖の阻害剤としての２−アミノピリジン置換ヘテロ環類 |
| WO2005007646A1 (en) | 2003-07-10 | 2005-01-27 | Neurogen Corporation | Substituted heterocyclic diarylamine analogues |
| GB0402653D0 (en) | 2004-02-06 | 2004-03-10 | Cyclacel Ltd | Compounds |
| US7521457B2 (en) | 2004-08-20 | 2009-04-21 | Boehringer Ingelheim International Gmbh | Pyrimidines as PLK inhibitors |
| FR2896503B1 (fr) | 2006-01-23 | 2012-07-13 | Aventis Pharma Sa | Nouveaux derives soufres d'uree cyclique, leur preparation et leur utilisation pharmaceutique comme inhibiteurs de kinases |
| CA2663091A1 (en) * | 2006-09-07 | 2008-03-13 | Biogen Idec Ma Inc. | Modulators of interleukin-1 receptor-associated kinase |
| AU2008258508A1 (en) | 2007-06-08 | 2008-12-11 | Bayer Cropscience Ag | Fungicide heterocyclyl-pyrimidinyl-amino derivatives |
| WO2009046416A1 (en) | 2007-10-05 | 2009-04-09 | Targegen Inc. | Anilinopyrimidines as jak kinase inhibitors |
| WO2010058846A1 (ja) | 2008-11-21 | 2010-05-27 | アステラス製薬株式会社 | ４，６-ジアミノニコチンアミド化合物 |
| AU2009320683B2 (en) | 2008-11-28 | 2012-07-19 | Kowa Company, Ltd. | Pyridine-3-carboxyamide derivative |
| EP2440204B1 (en) | 2009-06-12 | 2013-12-18 | Bristol-Myers Squibb Company | Nicotinamide compounds useful as kinase modulators |
| EP2493863B1 (en) | 2009-10-30 | 2015-02-25 | Janssen Pharmaceutica NV | Phenoxy-substituted pyrimidines as opioid receptor modulators |
| US20190192510A1 (en) | 2010-02-01 | 2019-06-27 | Nippon Chemiphar Co., Ltd. | Gpr119 agonist |
| WO2012149567A1 (en) | 2011-04-29 | 2012-11-01 | Mount Sinai School Of Medicine | Kinase inhibitors |
| EP2802577B1 (en) * | 2012-01-13 | 2017-03-01 | Bristol-Myers Squibb Company | Triazolyl-substituted pyridyl compounds useful as kinase inhibitors |
| WO2013106612A1 (en) * | 2012-01-13 | 2013-07-18 | Bristol-Myers Squibb Company | Heterocyclic-substituted pyridyl compounds useful as kinase inhibitors |
| US9242976B2 (en) | 2012-01-13 | 2016-01-26 | Bristol-Myers Squibb Company | Thiazolyl- or thiadiazolyl-substituted pyridyl compounds useful as kinase inhibitors |
| ES2616812T3 (es) | 2012-11-08 | 2017-06-14 | Bristol-Myers Squibb Company | Compuestos piridilo sustituidos con heterociclo bicíclico útiles como moduladores de quinasa |
| WO2014074660A1 (en) | 2012-11-08 | 2014-05-15 | Bristol-Myers Squibb Company | ALKYL-AMIDE-SUBSTITUTED PYRIDYL COMPOUNDS USEFUL AS MODULATORS OF IL-12, IL-23 AND/OR IFNα RESPONSES |
| PE20150953A1 (es) | 2012-11-08 | 2015-06-20 | Bristol Myers Squibb Co | Compuestos de piridilo sustituidos con heteroarilo utiles como moduladores de cinasa |
| TWI582077B (zh) | 2013-11-07 | 2017-05-11 | 必治妥美雅史谷比公司 | 作爲ＩＬ－１２、ＩＬ－２３及／或ＩＦＮα反應調節劑之經烷基－醯胺取代之吡啶化合物 |
| TW201609693A (zh) | 2014-01-03 | 2016-03-16 | 必治妥美雅史谷比公司 | 雜芳基取代之菸鹼醯胺化合物 |
| AR105113A1 (es) * | 2015-06-24 | 2017-09-06 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituida con heteroarilo |
| UY36747A (es) | 2015-06-24 | 2016-12-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de aminopiridina sustituida con heteroarilo como inhibidores de quinasa y modulantes de irak-4 y composiciones farmacéuticas que los contienen |
-
2016
- 2016-06-23 UY UY0001036747A patent/UY36747A/es not_active Application Discontinuation
- 2016-06-23 AR ARP160101893A patent/AR105114A1/es unknown
- 2016-06-23 EP EP16734832.5A patent/EP3313844B1/en active Active
- 2016-06-23 TW TW105119779A patent/TW201713663A/zh unknown
- 2016-06-23 CN CN201680043479.4A patent/CN108026099B/zh active Active
- 2016-06-23 JP JP2017566812A patent/JP6720225B2/ja active Active
- 2016-06-23 WO PCT/US2016/038862 patent/WO2016210037A1/en not_active Ceased
- 2016-06-23 ES ES16734832T patent/ES2822956T3/es active Active
- 2016-06-23 US US15/738,435 patent/US10202390B2/en active Active
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