JP2017527548A5 - - Google Patents
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- Publication number
- JP2017527548A5 JP2017527548A5 JP2017507807A JP2017507807A JP2017527548A5 JP 2017527548 A5 JP2017527548 A5 JP 2017527548A5 JP 2017507807 A JP2017507807 A JP 2017507807A JP 2017507807 A JP2017507807 A JP 2017507807A JP 2017527548 A5 JP2017527548 A5 JP 2017527548A5
- Authority
- JP
- Japan
- Prior art keywords
- pyridin
- amine
- isoxazolo
- optionally substituted
- nhr
- 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
- 125000003107 substituted aryl group Chemical group 0.000 claims 35
- 229910052757 nitrogen Inorganic materials 0.000 claims 27
- 125000001072 heteroaryl group Chemical group 0.000 claims 15
- 239000008194 pharmaceutical composition Substances 0.000 claims 14
- 125000001424 substituent group Chemical group 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 11
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 229910052760 oxygen Inorganic materials 0.000 claims 10
- 125000004122 cyclic group Chemical group 0.000 claims 9
- XEYWCHKONZUDGB-UHFFFAOYSA-N 5-chloro-4,6-dimethyl-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound CC1=C(Cl)C(C)=NC2=C1C(N)=NO2 XEYWCHKONZUDGB-UHFFFAOYSA-N 0.000 claims 8
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 108020005497 Nuclear hormone receptor Proteins 0.000 claims 8
- 125000004432 carbon atom Chemical group C* 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 7
- 125000005843 halogen group Chemical group 0.000 claims 7
- 229920006395 saturated elastomer Polymers 0.000 claims 7
- GIBMCZLVZLKVQG-UHFFFAOYSA-N BrC=1C(=C2C(=NC=1C)ON=C2N)C Chemical compound BrC=1C(=C2C(=NC=1C)ON=C2N)C GIBMCZLVZLKVQG-UHFFFAOYSA-N 0.000 claims 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- NIHLEQFZWNKMEY-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound C1=CC=C2C(N)=NOC2=N1 NIHLEQFZWNKMEY-UHFFFAOYSA-N 0.000 claims 5
- 125000002883 imidazolyl group Chemical group 0.000 claims 5
- 125000002757 morpholinyl group Chemical group 0.000 claims 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 5
- DYMSNXTUZQZFSM-UHFFFAOYSA-N 4,6-dimethyl-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound CC1=CC(C)=C2C(N)=NOC2=N1 DYMSNXTUZQZFSM-UHFFFAOYSA-N 0.000 claims 4
- GYVPSYJDRWKPPV-UHFFFAOYSA-N 5-chloro-[1,2]oxazolo[5,4-b]pyridin-3-amine Chemical compound C1=C(Cl)C=C2C(N)=NOC2=N1 GYVPSYJDRWKPPV-UHFFFAOYSA-N 0.000 claims 4
- PDKYYNMMWLZHAR-UHFFFAOYSA-N C(C)(C)C1=CC=C2C(=N1)ON=C2N Chemical compound C(C)(C)C1=CC=C2C(=N1)ON=C2N PDKYYNMMWLZHAR-UHFFFAOYSA-N 0.000 claims 4
- KRJAAEYJGMMGBQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1(C=CC=2C(=N1)ONC=2N)N Chemical compound C1(=CC=CC=C1)C1(C=CC=2C(=N1)ONC=2N)N KRJAAEYJGMMGBQ-UHFFFAOYSA-N 0.000 claims 4
- RQYGWIFUAGWQTQ-UHFFFAOYSA-N C1(=CC=CC=C1)C1=C2C(=NC=C1)ON=C2N Chemical compound C1(=CC=CC=C1)C1=C2C(=NC=C1)ON=C2N RQYGWIFUAGWQTQ-UHFFFAOYSA-N 0.000 claims 4
- ZSBNCQKXLKCXMV-UHFFFAOYSA-N C1(=CC=CC=C1)C1=CC=C2C(=N1)ON=C2N Chemical compound C1(=CC=CC=C1)C1=CC=C2C(=N1)ON=C2N ZSBNCQKXLKCXMV-UHFFFAOYSA-N 0.000 claims 4
- ZTJREVULHHQPON-UHFFFAOYSA-N CC1(C=CC=2C(=N1)ONC=2N)NC Chemical compound CC1(C=CC=2C(=N1)ONC=2N)NC ZTJREVULHHQPON-UHFFFAOYSA-N 0.000 claims 4
- YRKCJEOMIIYMAZ-UHFFFAOYSA-N CC1(CC=2C=C3C(=NC=2CC1)ON=C3N)C Chemical compound CC1(CC=2C=C3C(=NC=2CC1)ON=C3N)C YRKCJEOMIIYMAZ-UHFFFAOYSA-N 0.000 claims 4
- IRLDKYAHPPZKEM-UHFFFAOYSA-N CC1=C2C(=NC(=C1C)C)ON=C2N Chemical compound CC1=C2C(=NC(=C1C)C)ON=C2N IRLDKYAHPPZKEM-UHFFFAOYSA-N 0.000 claims 4
- XQBXFFNKIPGUJX-UHFFFAOYSA-N CC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F Chemical compound CC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F XQBXFFNKIPGUJX-UHFFFAOYSA-N 0.000 claims 4
- NBKLMRMGMSDYOZ-UHFFFAOYSA-N CC=1C=C2C(=NC=1)ON=C2N Chemical compound CC=1C=C2C(=NC=1)ON=C2N NBKLMRMGMSDYOZ-UHFFFAOYSA-N 0.000 claims 4
- ANEPQTAUFJDZSB-UHFFFAOYSA-N CC=1C=C2C(=NC=1C)ON=C2N Chemical compound CC=1C=C2C(=NC=1C)ON=C2N ANEPQTAUFJDZSB-UHFFFAOYSA-N 0.000 claims 4
- ZUOFIOIZPVAMAG-UHFFFAOYSA-N CN(CCCOC1=CC=C2C(=N1)ON=C2N)C Chemical compound CN(CCCOC1=CC=C2C(=N1)ON=C2N)C ZUOFIOIZPVAMAG-UHFFFAOYSA-N 0.000 claims 4
- AXDAHCXGMJSBOW-UHFFFAOYSA-N CN(CCOC1=CC=C2C(=N1)ON=C2N)C Chemical compound CN(CCOC1=CC=C2C(=N1)ON=C2N)C AXDAHCXGMJSBOW-UHFFFAOYSA-N 0.000 claims 4
- KUTMWJSWDFIUMW-UHFFFAOYSA-N CN1N=CC=C1C1=CC=C2C(N)=NOC2=N1 Chemical compound CN1N=CC=C1C1=CC=C2C(N)=NOC2=N1 KUTMWJSWDFIUMW-UHFFFAOYSA-N 0.000 claims 4
- DIWMNIZUAXAZIS-UHFFFAOYSA-N COC1=C(C=CC=C1)C=1C=C2C(=NC=1)ON=C2N Chemical compound COC1=C(C=CC=C1)C=1C=C2C(=NC=1)ON=C2N DIWMNIZUAXAZIS-UHFFFAOYSA-N 0.000 claims 4
- HWEZWOQRYRSPSM-UHFFFAOYSA-N COC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 Chemical compound COC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 HWEZWOQRYRSPSM-UHFFFAOYSA-N 0.000 claims 4
- AJDYMYFAFLHROU-UHFFFAOYSA-N COC1=C2C(=NC=C1)ON=C2N Chemical compound COC1=C2C(=NC=C1)ON=C2N AJDYMYFAFLHROU-UHFFFAOYSA-N 0.000 claims 4
- TYEANTJQCKKWPT-UHFFFAOYSA-N COC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 Chemical compound COC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 TYEANTJQCKKWPT-UHFFFAOYSA-N 0.000 claims 4
- UYRZVLMGJJYUDM-UHFFFAOYSA-N COC=1C=C(C=CC=1)C1(C=CC=2C(=N1)ONC=2N)N Chemical compound COC=1C=C(C=CC=1)C1(C=CC=2C(=N1)ONC=2N)N UYRZVLMGJJYUDM-UHFFFAOYSA-N 0.000 claims 4
- VQIDBFITOQUYEJ-UHFFFAOYSA-N COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N Chemical compound COC=1C=C(C=CC=1)C=1C=C2C(=NC=1)ON=C2N VQIDBFITOQUYEJ-UHFFFAOYSA-N 0.000 claims 4
- DXMBXEWBMFZBFL-UHFFFAOYSA-N COC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1 Chemical compound COC=1C=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=1 DXMBXEWBMFZBFL-UHFFFAOYSA-N 0.000 claims 4
- PFYYQOZVOGLKEV-UHFFFAOYSA-N COCC#CC=1C=C2C(=NC=1)ON=C2N Chemical compound COCC#CC=1C=C2C(=NC=1)ON=C2N PFYYQOZVOGLKEV-UHFFFAOYSA-N 0.000 claims 4
- UYMVPQHQKHTCGV-UHFFFAOYSA-N CS(=O)(=O)C1=CC=C2C(=N1)ON=C2N Chemical compound CS(=O)(=O)C1=CC=C2C(=N1)ON=C2N UYMVPQHQKHTCGV-UHFFFAOYSA-N 0.000 claims 4
- DUHFWRRZLVAQBD-UHFFFAOYSA-N CSC1=C2C(=NC(=N1)C1=CC=CC=C1)ON=C2N Chemical compound CSC1=C2C(=NC(=N1)C1=CC=CC=C1)ON=C2N DUHFWRRZLVAQBD-UHFFFAOYSA-N 0.000 claims 4
- KWUCRDFOHKSXGE-UHFFFAOYSA-N CSC1=CC=C2C(=N1)ON=C2N Chemical compound CSC1=CC=C2C(=N1)ON=C2N KWUCRDFOHKSXGE-UHFFFAOYSA-N 0.000 claims 4
- JLNARRUFROTVGE-UHFFFAOYSA-N CSC1=NC=C2C(=N1)ON=C2N Chemical compound CSC1=NC=C2C(=N1)ON=C2N JLNARRUFROTVGE-UHFFFAOYSA-N 0.000 claims 4
- 101100240519 Caenorhabditis elegans nhr-13 gene Proteins 0.000 claims 4
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims 4
- MTIDNIWREKNKHM-UHFFFAOYSA-N ClC1=C(C=C2C(=N1)ON=C2N)F Chemical compound ClC1=C(C=C2C(=N1)ON=C2N)F MTIDNIWREKNKHM-UHFFFAOYSA-N 0.000 claims 4
- FTYNGVVGVBNMCZ-UHFFFAOYSA-N ClC1=C(C=CC(=C1)C(F)(F)F)C=1C=C2C(=NC=1)ON=C2N Chemical compound ClC1=C(C=CC(=C1)C(F)(F)F)C=1C=C2C(=NC=1)ON=C2N FTYNGVVGVBNMCZ-UHFFFAOYSA-N 0.000 claims 4
- GJTXCKVACBHJBM-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C1=CC=C2C(=N1)ON=C2N Chemical compound ClC1=C(C=CC(=C1)Cl)C1=CC=C2C(=N1)ON=C2N GJTXCKVACBHJBM-UHFFFAOYSA-N 0.000 claims 4
- RFTAMIIFXPPDDT-UHFFFAOYSA-N ClC1=C(C=CC(=C1)Cl)C=1C=C2C(=NC=1)ON=C2N Chemical compound ClC1=C(C=CC(=C1)Cl)C=1C=C2C(=NC=1)ON=C2N RFTAMIIFXPPDDT-UHFFFAOYSA-N 0.000 claims 4
- RGXPNUXXIAJTCF-UHFFFAOYSA-N ClC1=C(C=CC(=C1Cl)Cl)C=1C=C2C(=NC=1)ON=C2N Chemical compound ClC1=C(C=CC(=C1Cl)Cl)C=1C=C2C(=NC=1)ON=C2N RGXPNUXXIAJTCF-UHFFFAOYSA-N 0.000 claims 4
- DJZPDCDBCOESKC-UHFFFAOYSA-N ClC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 Chemical compound ClC1=C(OC2=CC=C3C(=N2)ON=C3N)C=CC=C1 DJZPDCDBCOESKC-UHFFFAOYSA-N 0.000 claims 4
- FQUKGVSRJVUOPA-UHFFFAOYSA-N ClC1=CC(=C2C(=N1)ON=C2N)C Chemical compound ClC1=CC(=C2C(=N1)ON=C2N)C FQUKGVSRJVUOPA-UHFFFAOYSA-N 0.000 claims 4
- RUNHWMKUSIPAOB-UHFFFAOYSA-N ClC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F Chemical compound ClC1=CC(=C2C(=N1)ON=C2N)C(F)(F)F RUNHWMKUSIPAOB-UHFFFAOYSA-N 0.000 claims 4
- XFQQQLSINPIKBY-UHFFFAOYSA-N ClC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 Chemical compound ClC1=CC=C(OC2=CC=C3C(=N2)ON=C3N)C=C1 XFQQQLSINPIKBY-UHFFFAOYSA-N 0.000 claims 4
- BBJRHZULJQREAE-UHFFFAOYSA-N ClC=1C(=C2C(=NC=1C)ON=C2NC)C Chemical compound ClC=1C(=C2C(=NC=1C)ON=C2NC)C BBJRHZULJQREAE-UHFFFAOYSA-N 0.000 claims 4
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| KR102746352B1 (ko) | 2014-08-13 | 2024-12-24 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
| CA2996681C (en) * | 2015-08-27 | 2024-04-09 | Auckland Uniservices Limited | Inhibitors of tryptophan dioxygenases (ido1 and tdo) and their use in therapy |
| RU2619120C1 (ru) * | 2016-06-06 | 2017-05-12 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный аграрный университет" | 5-Хлор-3-(3-хлорфенилкарбоксамидо)-4,6-диметилизоксазоло[5,4-b]пиридин в качестве антидота 2,4-Д на подсолнечнике |
| EP3269714A1 (en) | 2016-07-13 | 2018-01-17 | Netherlands Translational Research Center B.V. | Inhibitors of tryptophan 2,3-dioxygenase |
| US10882856B2 (en) | 2016-09-24 | 2021-01-05 | Beigene, Ltd. | 5 or 8-substituted imidazo [1,5-a] pyridines as selective inhibitors of indoleamine and/or tryptophane 2,3-dioxygenases |
| JP7623784B2 (ja) | 2016-10-13 | 2025-01-29 | ジュノー セラピューティクス インコーポレイテッド | トリプトファン代謝経路調節剤を含む免疫療法の方法および組成物 |
| CA3047002A1 (en) | 2017-01-17 | 2018-07-26 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| CN106905256A (zh) * | 2017-03-06 | 2017-06-30 | 中国药科大学 | 苯并五元杂环类ido1抑制剂、其制备方法及应用 |
| KR20200074971A (ko) * | 2017-10-19 | 2020-06-25 | 제이에스 이노팜 (상하이) 리미티드 | 헤테로사이클릭 화합물, 헤테로사이클릭 화합물을 포함하는 조성물 및 그의 사용 방법 |
| CN110278060B (zh) | 2018-03-14 | 2024-07-16 | 华为技术有限公司 | 数据传输方法、装置及系统 |
| WO2020018670A1 (en) | 2018-07-17 | 2020-01-23 | Board Of Regents, The University Of Texas System | Compounds useful as inhibitors of indoleamine 2,3-dioxygenase and/or tryptophan dioxygenase |
| JP6912016B1 (ja) * | 2020-04-10 | 2021-07-28 | 小野薬品工業株式会社 | Ｓｔｉｎｇ作動化合物 |
| KR102653960B1 (ko) * | 2020-07-23 | 2024-04-03 | 의료법인 성광의료재단 | 암 치료를 위한 면역체크포인트 억제제의 병용 요법 |
| EP4052705A1 (en) | 2021-03-05 | 2022-09-07 | Universität Basel Vizerektorat Forschung | Compositions for the treatment of ebv associated diseases or conditions |
| MX2023010371A (es) | 2021-03-05 | 2024-02-12 | Univ Basel | Composiciones para el tratamiento de enfermedades o condiciones asociadas al veb. |
| JP2025507981A (ja) | 2022-03-04 | 2025-03-21 | アンティド セラピューティクス インターナショナル ソシエテ ア レスポンサビリテ リミティー | トリプトファンジオキシゲナーゼ（ｉｄｏ１及びｔｄｏ）の二重阻害剤と療法におけるそれらの使用 |
| WO2025046519A1 (en) * | 2023-08-31 | 2025-03-06 | Antido Therapeutics International Sarl | Combination for use in the treatment of glioma |
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| PL123588B1 (en) | 1979-12-20 | 1982-10-30 | Akad Rolnicza | Rotary dynamometer for measurement of useful work of machining |
| AU2001255410A1 (en) | 2000-04-14 | 2001-10-30 | Corvas International, Inc. | Substituted hydrazinyl heteroaromatic inhibitors of thrombin |
| CA2559105A1 (en) | 2004-03-16 | 2005-09-29 | Janssen Pharmaceutica N.V. | Benzisoxazoles |
| TW200633990A (en) | 2004-11-18 | 2006-10-01 | Takeda Pharmaceuticals Co | Amide compound |
| PL1879573T3 (pl) * | 2005-05-10 | 2013-05-31 | Incyte Holdings Corp | Modulatory 2,3-dioksygenazy indoloaminy i sposoby ich zastosowania |
| DE102005038947A1 (de) | 2005-05-18 | 2006-11-30 | Grünenthal GmbH | Substituierte Benzo[d]isoxazol-3-yl-amin-Verbindungen und deren Verwendung in Arzneimitteln |
| DE102005026194A1 (de) | 2005-06-06 | 2006-12-07 | Grünenthal GmbH | Substituierte N-Benzo[d]isoxazol-3-yl-amin-Derivate und deren Verwendung zur Herstellung von Arzneimitteln |
| US10047066B2 (en) | 2007-11-30 | 2018-08-14 | Newlink Genetics Corporation | IDO inhibitors |
| US8461159B2 (en) | 2008-11-25 | 2013-06-11 | Jannsen Pharmaceutica BV | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| WO2010068452A1 (en) | 2008-11-25 | 2010-06-17 | Janssen Pharmaceutica Nv | Heteroaryl-substituted urea modulators of fatty acid amide hydrolase |
| CA2754934A1 (en) | 2009-03-10 | 2010-09-16 | Gruenenthal Gmbh | Substituted 3-aminoisoxazolopyridines as kcnq2/3 modulators |
| MX2012009377A (es) | 2010-02-11 | 2012-09-12 | Univ Vanderbilt | Benzotiazoles y azabenzotiazoles como potenciadores alostericos mglur4, composiciones y metodos para tratar la disfuncion neurologica. |
| US20100234491A1 (en) * | 2010-05-27 | 2010-09-16 | Morteza Khorrami | Method and material for manufacturing fiber cement board |
| DK2595995T3 (en) | 2010-07-22 | 2016-02-29 | Basf Se | Herbicidal isoxazolo [5,4-b] pyridines |
| JP5672077B2 (ja) * | 2011-03-04 | 2015-02-18 | セイコーエプソン株式会社 | 発光素子、発光装置、表示装置および電子機器 |
| EP2802212B1 (en) | 2012-01-12 | 2015-12-30 | Basf Se | Herbicidal isoxazolo[5,4-b]pyridines |
| PL220630B1 (pl) * | 2012-12-28 | 2015-11-30 | Inst Immunologii I Terapii Doświadczalnej Pan | Nowe sulfonamidowe pochodne izoksazolo[5,4-b]pirydyny o aktywności przeciwbakteryjnej, sposób ich wytwarzania oraz nowe zastosowanie 3-aminoizoksazolo[5,4-b]pirydyny |
| SG11201507395PA (en) | 2013-03-14 | 2015-10-29 | Curadev Pharma Private Ltd | Inhibitors of the kynurenine pathway |
| US9931347B2 (en) | 2013-12-03 | 2018-04-03 | Iomet Pharma Ltd. | Pharmaceutical compound |
| KR102746352B1 (ko) | 2014-08-13 | 2024-12-24 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
| RU2619120C1 (ru) | 2016-06-06 | 2017-05-12 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный аграрный университет" | 5-Хлор-3-(3-хлорфенилкарбоксамидо)-4,6-диметилизоксазоло[5,4-b]пиридин в качестве антидота 2,4-Д на подсолнечнике |
-
2015
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2020
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2023
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