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 |
|---|---|---|---|
| IN1880/DEL/2015 | 2015-06-24 | ||
| IN1880DE2015 | 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 |
|---|---|---|---|---|
| US10618903B2 (en) * | 2015-06-24 | 2020-04-14 | Bristol-Myers Squibb Company | Heteroaryl substituted aminopyridine compounds |
| EP3313840B1 (en) | 2015-06-24 | 2019-07-24 | Bristol-Myers Squibb Company | Heteroaryl substituted aminopyridine compounds |
| ES2822956T3 (es) | 2015-06-24 | 2021-05-05 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituidos con heteroarilo |
| TW202340194A (zh) | 2017-02-16 | 2023-10-16 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒𠯤衍生物 |
| PT3621960T (pt) | 2017-05-11 | 2021-09-16 | Bristol Myers Squibb Co | Tienopiridinas e benzotiofenos úteis como inibidores de irak4 |
| WO2019111218A1 (en) | 2017-12-08 | 2019-06-13 | Cadila Healthcare Limited | Novel heterocyclic compounds as irak4 inhibitors |
| TWI842978B (zh) | 2018-07-13 | 2024-05-21 | 美商基利科學股份有限公司 | 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 |
| TWI797366B (zh) | 2018-08-13 | 2023-04-01 | 美商基利科學股份有限公司 | 吡咯并[1,2-b]嗒衍生物 |
| WO2020036830A1 (en) | 2018-08-13 | 2020-02-20 | Gilead Sciences, Inc. | Pyrrolo[1,2-b]pyridazine derivatives as irak4 inhibitors |
| EP3999508B1 (en) | 2019-07-18 | 2023-08-30 | 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 |
| US12304916B2 (en) | 2019-07-23 | 2025-05-20 | Bristol-Myers Squibb Company | Thienopyridinyl and thiazolopyridinyl compounds useful as IRAK4 inhibitors |
| WO2021026181A1 (en) | 2019-08-06 | 2021-02-11 | Bristol-Myers Squibb Company | Bicyclic heterocyclic compounds useful as irak4 inhibitors |
| ES3059914T3 (en) | 2019-08-13 | 2026-03-24 | Bristol Myers Squibb Co | Bicyclic heteroaryl compounds useful as irak4 inhibitors |
| US12421230B2 (en) | 2020-02-03 | 2025-09-23 | Bristol-Myers Squibb Company | Tricyclic heteroaryl compounds useful as IRAK4 inhibitors |
| WO2021158495A1 (en) | 2020-02-03 | 2021-08-12 | Bristol-Myers Squibb Company | Benzo[5,6][1,4]dioxino[2,3-b]pyridine compounds useful as irak4 inhibitors |
| WO2021168197A1 (en) | 2020-02-19 | 2021-08-26 | 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 |
| CN117813307A (zh) | 2021-08-18 | 2024-04-02 | 新锐思生物制药股份有限公司 | 白介素-1受体相关激酶的双官能降解物及其治疗用途 |
Family Cites Families (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2450769A1 (en) | 2001-06-15 | 2002-12-27 | Vertex Pharmaceuticals Incorporated | 5-(2-aminopyrimidin-4-yl) benzisoxazoles as protein kinase inhibitors |
| 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 |
| EP1518855B1 (en) | 2002-06-28 | 2011-10-26 | Astellas Pharma Inc. | Diaminopyrimidinecarboxa mide derivative |
| MXPA05007503A (es) | 2003-01-17 | 2005-09-21 | Warner Lambert Co | Heterociclicos 2-aminopiridina sustituidos como inhibidores de proliferacion celular. |
| 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 |
| CN101594909A (zh) * | 2006-09-07 | 2009-12-02 | 比奥根艾迪克Ma公司 | 用于治疗炎性病症、细胞增殖性失调、免疫失调的irak调节剂 |
| KR20100020454A (ko) | 2007-06-08 | 2010-02-22 | 바이엘 크롭사이언스 소시에떼아노님 | 살진균제 헤테로사이클릴-피리미디닐-아미노 유도체 |
| WO2009046416A1 (en) | 2007-10-05 | 2009-04-09 | Targegen Inc. | Anilinopyrimidines as jak kinase inhibitors |
| EP2361902A4 (en) | 2008-11-21 | 2012-04-25 | Astellas Pharma Inc | 4,6-DIAMINONICOTINSÄUREAMIDVERBINDUNG |
| WO2010061971A1 (ja) | 2008-11-28 | 2010-06-03 | 興和株式会社 | ピリジン－３－カルボキシアミド誘導体 |
| 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 |
| KR20120130104A (ko) | 2010-02-01 | 2012-11-28 | 닛뽕 케미파 가부시키가이샤 | Ｇｐｒ119 작동약 |
| JP2014515029A (ja) | 2011-04-29 | 2014-06-26 | アイカーン・スクール・オブ・メディシン・アト・マウント・シナイ | キナーゼ阻害剤 |
| ES2575604T3 (es) * | 2012-01-13 | 2016-06-29 | Bristol-Myers Squibb Company | Compuestos de piridilo sustituidos con tiazolilo o tiadiazolilo útiles como inhibidores cinasa |
| CN104169275B (zh) | 2012-01-13 | 2017-06-09 | 百时美施贵宝公司 | 用作激酶抑制剂的三唑取代的吡啶化合物 |
| EP2802576B1 (en) | 2012-01-13 | 2018-06-27 | Bristol-Myers Squibb Company | Heterocyclic-substituted pyridyl compounds useful as kinase inhibitors |
| BR112015009850A2 (pt) | 2012-11-08 | 2017-07-11 | Bristol Myers Squibb Co | compostos de piridila substituídos por heteroarila úteis como moduladores de quinase |
| KR102233252B1 (ko) | 2012-11-08 | 2021-03-26 | 브리스톨-마이어스 스큅 컴퍼니 | ＩＬ-12, ＩＬ-23 및/또는 ＩＦＮα 반응의 조절제로서 유용한 알킬-아미드-치환된 피리딜 화합물 |
| JP6215338B2 (ja) | 2012-11-08 | 2017-10-18 | ブリストル−マイヤーズ スクイブ カンパニーＢｒｉｓｔｏｌ−Ｍｙｅｒｓ Ｓｑｕｉｂｂ Ｃｏｍｐａｎｙ | キナーゼモジュレーターとして有用な二環式ヘテロ環置換ピリジル化合物 |
| 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 |
| UY35935A (es) * | 2014-01-03 | 2015-06-30 | Bristol Myers Squibb Company Una Corporación Del Estado De Delaware | Compuestos de nicotinamida sustituida con heteroarilo como inhibidores de quinasa y moduladores de irak-4 |
| ES2822956T3 (es) | 2015-06-24 | 2021-05-05 | Bristol Myers Squibb Co | Compuestos de aminopiridina sustituidos con heteroarilo |
| EP3313840B1 (en) * | 2015-06-24 | 2019-07-24 | Bristol-Myers Squibb Company | Heteroaryl substituted aminopyridine compounds |
-
2016
- 2016-06-23 ES ES16734832T patent/ES2822956T3/es active Active
- 2016-06-23 AR ARP160101893A patent/AR105114A1/es unknown
- 2016-06-23 JP JP2017566812A patent/JP6720225B2/ja active Active
- 2016-06-23 UY UY0001036747A patent/UY36747A/es not_active Application Discontinuation
- 2016-06-23 US US15/738,435 patent/US10202390B2/en active Active
- 2016-06-23 EP EP16734832.5A patent/EP3313844B1/en active Active
- 2016-06-23 CN CN201680043479.4A patent/CN108026099B/zh active Active
- 2016-06-23 WO PCT/US2016/038862 patent/WO2016210037A1/en not_active Ceased
- 2016-06-23 TW TW105119779A patent/TW201713663A/zh unknown
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