CA2866450C - Triazolopyrazine derivatives - Google Patents
Triazolopyrazine derivatives Download PDFInfo
- Publication number
- CA2866450C CA2866450C CA2866450A CA2866450A CA2866450C CA 2866450 C CA2866450 C CA 2866450C CA 2866450 A CA2866450 A CA 2866450A CA 2866450 A CA2866450 A CA 2866450A CA 2866450 C CA2866450 C CA 2866450C
- Authority
- CA
- Canada
- Prior art keywords
- pyrazin
- triazolo
- phenyl
- methyl
- amine
- 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.)
- Expired - Fee Related
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- CJGGKSPGRJHZNP-UHFFFAOYSA-N 2h-triazolo[4,5-b]pyrazine Chemical class C1=CN=C2NN=NC2=N1 CJGGKSPGRJHZNP-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 217
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- 201000011510 cancer Diseases 0.000 claims abstract description 44
- 238000000034 method Methods 0.000 claims description 166
- -1 2,3-dihydrobenzo[1,4]dioxinyl Chemical group 0.000 claims description 116
- 150000003839 salts Chemical class 0.000 claims description 81
- 239000000203 mixture Substances 0.000 claims description 69
- 239000012453 solvate Substances 0.000 claims description 39
- 239000003814 drug Substances 0.000 claims description 37
- 239000004480 active ingredient Substances 0.000 claims description 36
- 230000015572 biosynthetic process Effects 0.000 claims description 31
- 238000003786 synthesis reaction Methods 0.000 claims description 28
- 230000002265 prevention Effects 0.000 claims description 22
- 210000004369 blood Anatomy 0.000 claims description 20
- 239000008280 blood Substances 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
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- 208000015122 neurodegenerative disease Diseases 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 230000004770 neurodegeneration Effects 0.000 claims description 15
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 206010025135 lupus erythematosus Diseases 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 125000004076 pyridyl group Chemical group 0.000 claims description 13
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 201000004681 Psoriasis Diseases 0.000 claims description 10
- 230000004968 inflammatory condition Effects 0.000 claims description 10
- 206010006187 Breast cancer Diseases 0.000 claims description 9
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- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 230000002503 metabolic effect Effects 0.000 claims description 9
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- 210000004556 brain Anatomy 0.000 claims description 7
- 229910052794 bromium Inorganic materials 0.000 claims description 7
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 7
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 7
- 210000004072 lung Anatomy 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 7
- 125000002971 oxazolyl group Chemical group 0.000 claims description 7
- 125000004193 piperazinyl group Chemical group 0.000 claims description 7
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000005493 quinolyl group Chemical group 0.000 claims description 7
- 210000002784 stomach Anatomy 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000000335 thiazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 210000001519 tissue Anatomy 0.000 claims description 7
- 125000001425 triazolyl group Chemical group 0.000 claims description 7
- 125000005871 1,3-benzodioxolyl group Chemical group 0.000 claims description 6
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 6
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 6
- 230000001363 autoimmune Effects 0.000 claims description 6
- 125000002393 azetidinyl group Chemical group 0.000 claims description 6
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000005052 dihydropyrazolyl group Chemical group N1(NCC=C1)* 0.000 claims description 6
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 claims description 6
- 125000005054 dihydropyrrolyl group Chemical group [H]C1=C([H])C([H])([H])C([H])([H])N1* 0.000 claims description 6
- 125000005945 imidazopyridyl group Chemical group 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
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- 125000003566 oxetanyl group Chemical group 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 125000003386 piperidinyl group Chemical group 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 6
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 6
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 6
- 125000005942 tetrahydropyridyl group Chemical group 0.000 claims description 6
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- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
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- 201000010374 Down Syndrome Diseases 0.000 claims description 2
- 208000006168 Ewing Sarcoma Diseases 0.000 claims description 2
- 208000007487 Familial Cerebral Amyloid Angiopathy Diseases 0.000 claims description 2
- 201000011240 Frontotemporal dementia Diseases 0.000 claims description 2
- 208000007465 Giant cell arteritis Diseases 0.000 claims description 2
- 208000001258 Hemangiosarcoma Diseases 0.000 claims description 2
- 241000711549 Hepacivirus C Species 0.000 claims description 2
- 208000032849 Hereditary cerebral hemorrhage with amyloidosis Diseases 0.000 claims description 2
- 241000701044 Human gammaherpesvirus 4 Species 0.000 claims description 2
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- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 206010043207 temporal arteritis Diseases 0.000 claims description 2
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 6
- AFWXZMZXYDJCCQ-UHFFFAOYSA-N 1-[4-[[5-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]amino]phenyl]cyclopropane-1-carbonitrile Chemical compound C1=NN(C)C=C1C1=CN=CC2=NC(NC=3C=CC(=CC=3)C3(CC3)C#N)=NN12 AFWXZMZXYDJCCQ-UHFFFAOYSA-N 0.000 claims 1
- SZHNJLPZTZARHU-UHFFFAOYSA-N 1-methyl-5-[[5-[1-(2-morpholin-4-ylethyl)pyrazol-4-yl]-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]amino]-3h-indol-2-one Chemical compound C=1C=C2N(C)C(=O)CC2=CC=1NC(=NN12)N=C1C=NC=C2C(=C1)C=NN1CCN1CCOCC1 SZHNJLPZTZARHU-UHFFFAOYSA-N 0.000 claims 1
- ASIYMHCXCPNPIU-UHFFFAOYSA-N 2-(3-methoxyanilino)-[1,2,4]triazolo[1,5-a]pyrazine-6-carbonitrile Chemical compound COC1=CC=CC(NC2=NN3C=C(N=CC3=N2)C#N)=C1 ASIYMHCXCPNPIU-UHFFFAOYSA-N 0.000 claims 1
- ZHGONOHIZKYGJZ-UHFFFAOYSA-N 2-methyl-2-[4-[2-(4-morpholin-4-ylanilino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]phenyl]propanenitrile Chemical compound C1=CC(C(C)(C#N)C)=CC=C1C1=CN=CC2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NN12 ZHGONOHIZKYGJZ-UHFFFAOYSA-N 0.000 claims 1
- JVFDIMFJRHKJSK-UHFFFAOYSA-N 2-n-[4-(4-methylpiperazin-1-yl)phenyl]-5-n-(1-methylpyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazine-2,5-diamine Chemical compound C1CN(C)CCN1C(C=C1)=CC=C1NC1=NN2C(NC3=CN(C)N=C3)=CN=CC2=N1 JVFDIMFJRHKJSK-UHFFFAOYSA-N 0.000 claims 1
- UXGLRDXIXIVUKM-UHFFFAOYSA-N 3-[[5-(1-methylindazol-5-yl)-[1,2,4]triazolo[1,5-a]pyrazin-2-yl]amino]benzenesulfonamide Chemical compound C=1C=C2N(C)N=CC2=CC=1C(N1N=2)=CN=CC1=NC=2NC1=CC=CC(S(N)(=O)=O)=C1 UXGLRDXIXIVUKM-UHFFFAOYSA-N 0.000 claims 1
- MMBZMWDNDWMCRX-UHFFFAOYSA-N 5,6-bis(1-methylpyrazol-4-yl)-n-(4-morpholin-4-ylphenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-amine Chemical compound C1=NN(C)C=C1C1=C(C2=CN(C)N=C2)N2N=C(NC=3C=CC(=CC=3)N3CCOCC3)N=C2C=N1 MMBZMWDNDWMCRX-UHFFFAOYSA-N 0.000 claims 1
- OPEJKPAAMLXQIW-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-n-(4-morpholin-4-ylphenyl)-6-phenyl-[1,2,4]triazolo[1,5-a]pyrazin-2-amine Chemical compound C1=NN(C)C=C1C1=C(C=2C=CC=CC=2)N=CC2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NN12 OPEJKPAAMLXQIW-UHFFFAOYSA-N 0.000 claims 1
- YZDGZRGMYIAZPE-UHFFFAOYSA-N 5-(1-methylpyrazol-4-yl)-n-(4-morpholin-4-ylphenyl)-[1,2,4]triazolo[1,5-a]pyrazin-2-amine Chemical compound C1=NN(C)C=C1C1=CN=CC2=NC(NC=3C=CC(=CC=3)N3CCOCC3)=NN12 YZDGZRGMYIAZPE-UHFFFAOYSA-N 0.000 claims 1
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| PCT/EP2013/000440 WO2013131609A1 (en) | 2012-03-07 | 2013-02-14 | Triazolopyrazine derivatives |
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| PE20160865A1 (es) * | 2013-12-19 | 2016-09-03 | Novartis Ag | Derivados de [1,2,4] triazolo [1,5-a]pirimidina como inhibidores de proteasoma para el tratamiento de enfermedades parasitarias tales como leishmaniasis |
| TWI720451B (zh) | 2014-02-13 | 2021-03-01 | 美商英塞特控股公司 | 作為lsd1抑制劑之環丙胺 |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| KR102421235B1 (ko) | 2014-02-13 | 2022-07-15 | 인사이트 코포레이션 | Lsd1 저해제로서 사이클로프로필아민 |
| US9493442B2 (en) | 2014-02-13 | 2016-11-15 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| US9758523B2 (en) | 2014-07-10 | 2017-09-12 | Incyte Corporation | Triazolopyridines and triazolopyrazines as LSD1 inhibitors |
| TWI687419B (zh) | 2014-07-10 | 2020-03-11 | 美商英塞特公司 | 作為ｌｓｄ１抑制劑之咪唑并吡啶及咪唑并吡嗪 |
| WO2016007722A1 (en) | 2014-07-10 | 2016-01-14 | Incyte Corporation | Triazolopyridines and triazolopyrazines as lsd1 inhibitors |
| TW201613925A (en) | 2014-07-10 | 2016-04-16 | Incyte Corp | Imidazopyrazines as LSD1 inhibitors |
| KR102602947B1 (ko) | 2014-11-03 | 2023-11-16 | 아이오메트 파마 엘티디 | 제약 화합물 |
| SG11201708047UA (en) | 2015-04-03 | 2017-10-30 | Incyte Corp | Heterocyclic compounds as lsd1 inhibitors |
| CN110402244B (zh) | 2015-08-12 | 2023-02-03 | 因赛特公司 | Lsd1抑制剂的盐 |
| SG10202010414QA (en) | 2016-04-22 | 2020-11-27 | Incyte Corp | Formulations of an lsd1 inhibitor |
| PT3498693T (pt) * | 2016-08-10 | 2024-12-18 | Takeda Pharmaceuticals Co | Composto heterocíclico |
| MX378460B (es) | 2016-12-22 | 2025-03-10 | Calithera Biosciences Inc | Composiciones y métodos para inhibir la actividad de la arginasa. |
| CN111918651B (zh) * | 2018-01-29 | 2024-01-30 | 默克专利股份有限公司 | Gcn2抑制剂及其用途 |
| EP3746071A4 (en) | 2018-01-29 | 2021-09-01 | Merck Patent GmbH | GCN2 INHIBITORS AND THEIR USES |
| CA3105721A1 (en) * | 2018-07-05 | 2020-01-09 | Incyte Corporation | Fused pyrazine derivatives as a2a / a2b inhibitors |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
| WO2021042911A1 (zh) * | 2019-09-05 | 2021-03-11 | 鲁南制药集团股份有限公司 | Magl抑制剂及其制备方法、用途 |
| GB202008749D0 (en) | 2020-06-09 | 2020-07-22 | Ip2Ipo Innovations Ltd | Novel compounds |
| WO2022271684A1 (en) * | 2021-06-23 | 2022-12-29 | Gilead Sciences, Inc. | Diacylglyercol kinase modulating compounds |
| CN115819425A (zh) * | 2022-12-22 | 2023-03-21 | 五邑大学 | 一种三唑并六元氮杂环-2-胺类化合物及其制备方法和应用 |
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| GB9624482D0 (en) | 1995-12-18 | 1997-01-15 | Zeneca Phaema S A | Chemical compounds |
| PL194689B1 (pl) | 1996-02-13 | 2007-06-29 | Astrazeneca Uk Ltd | Pochodne chinazoliny, ich kompozycje farmaceutyczne oraz ich zastosowania |
| EP0885198B1 (en) | 1996-03-05 | 2001-12-19 | AstraZeneca AB | 4-anilinoquinazoline derivatives |
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| EP1289952A1 (en) | 2000-05-31 | 2003-03-12 | AstraZeneca AB | Indole derivatives with vascular damaging activity |
| CN1255391C (zh) | 2000-07-07 | 2006-05-10 | 安吉奥金尼药品有限公司 | 作为血管破坏剂的colchinol衍生物 |
| WO2002008213A1 (en) | 2000-07-07 | 2002-01-31 | Angiogene Pharmaceuticals Limited | Colchinol derivatives as angiogenesis inhibitors |
| ATE370142T1 (de) | 2003-07-16 | 2007-09-15 | Janssen Pharmaceutica Nv | Triazolopyrimidinderivate als inhibitoren von glycogensynthasekinase-3 |
| CN101022799A (zh) | 2004-07-19 | 2007-08-22 | 约翰·霍普金斯大学 | 供免疫抑制的flt3抑制剂 |
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| CN101454326A (zh) * | 2006-05-31 | 2009-06-10 | 加拉帕戈斯股份有限公司 | 用于治疗变性和炎性疾病的三唑并吡嗪化合物 |
| TWI453207B (zh) * | 2008-09-08 | 2014-09-21 | Signal Pharm Llc | 胺基三唑并吡啶，其組合物及使用其之治療方法 |
| KR20120044966A (ko) * | 2009-06-05 | 2012-05-08 | 세파론, 인코포레이티드 | 1,2,4-트리아졸로〔1,5ａ〕 피리딘 유도체의 제조 및 용도 |
| EP2523949B1 (en) * | 2010-01-15 | 2014-08-20 | Janssen Pharmaceuticals Inc. | Novel substituted triazole derivatives as gamma secretase modulators |
| US20110190269A1 (en) * | 2010-02-01 | 2011-08-04 | Karlheinz Baumann | Gamma secretase modulators |
| JP5951610B2 (ja) * | 2010-08-27 | 2016-07-13 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | トリアゾロピラジン誘導体 |
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| US20150051202A1 (en) | 2015-02-19 |
| EP2822948B1 (en) | 2016-04-06 |
| EP2822948A1 (en) | 2015-01-14 |
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| ES2579981T3 (es) | 2016-08-18 |
| AU2013230286B2 (en) | 2016-12-22 |
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| CA2866450A1 (en) | 2013-09-12 |
| HK1203948A1 (en) | 2015-11-06 |
| JP6049768B2 (ja) | 2016-12-21 |
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