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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- WTXNZXKXRNMDDT-UHFFFAOYSA-N [1,2]oxazolo[5,4-b]quinolin-3-amine Chemical compound C1=CC=C2C=C3C(N)=NOC3=NC2=C1 WTXNZXKXRNMDDT-UHFFFAOYSA-N 0.000 claims 2
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| KR20250007032A (ko) | 2014-08-13 | 2025-01-13 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
| AU2016312848A1 (en) | 2015-08-27 | 2018-03-29 | 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 |
| WO2018054365A1 (en) | 2016-09-24 | 2018-03-29 | Beigene, Ltd. | NOVEL 5 or 8-SUBSTITUTED IMIDAZO [1, 5-a] PYRIDINES AS SELECTIVE INHIBITORS OF INDOLEAMINE AND/OR TRYPTOPHANE 2, 3-DIOXYGENASES |
| MA50839A (fr) | 2016-10-13 | 2019-08-21 | Juno Therapeutics Inc | Méthodes et compositions d'immunothérapie impliquant des modulateurs de la voie métabolique du tryptophane |
| 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 |
| WO2019076358A1 (en) * | 2017-10-19 | 2019-04-25 | Js Innopharm (Shanghai) Ltd | HETEROCYCLIC COMPOUNDS, COMPOSITIONS COMPRISING THE HETEROCYCLIC COMPOUND, AND METHODS OF USE THEREOF |
| CN118740348A (zh) * | 2018-03-14 | 2024-10-01 | 华为技术有限公司 | 数据传输方法、装置及系统 |
| EP3823604A4 (en) | 2018-07-17 | 2022-03-16 | Board of Regents, The University of Texas System | COMPOUNDS AS INHIBITORS OF INDOLAMINE-2,3-DIOXYGENASE AND/OR TRYPTOPHANE 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 |
| JP2024510949A (ja) | 2021-03-05 | 2024-03-12 | ウニヴェルシタット・バーゼル | Ｅｂｖ関連疾患又は状態の治療用組成物 |
| US20250186410A1 (en) | 2022-03-04 | 2025-06-12 | Antido Therapeutics International Sàrl | Dual inhibitors of tryptophan dioxygenases (ido1 and tdo) and their use in therapy |
| 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 |
| WO2001079193A2 (en) | 2000-04-14 | 2001-10-25 | Corvas International, Inc. | Substituted hydrazinyl heteroaromatic inhibitors of thrombin |
| JP2007529468A (ja) | 2004-03-16 | 2007-10-25 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | ベンズイソオキサゾール |
| TW200633990A (en) | 2004-11-18 | 2006-10-01 | Takeda Pharmaceuticals Co | Amide compound |
| RS54876B1 (sr) * | 2005-05-10 | 2016-10-31 | Incyte Holdings Corp | Modulatori indoleamina 2,3-dioksigenaze i metode za upotrebu istih |
| 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 |
| EP2227233B1 (en) | 2007-11-30 | 2013-02-13 | Newlink Genetics | 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 |
| US8916584B2 (en) * | 2010-02-11 | 2014-12-23 | Vanderbilt University | Benzisoxazoles and azabenzisoxazoles as MGLUR4 allosteric potentiators, compositions, and methods of treating neurological dysfunction |
| US20100234491A1 (en) * | 2010-05-27 | 2010-09-16 | Morteza Khorrami | Method and material for manufacturing fiber cement board |
| ES2564017T3 (es) | 2010-07-22 | 2016-03-17 | Basf Se | Isoxazolo[5,4-b]piridinas herbicidas |
| 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 |
| KR102189529B1 (ko) | 2013-03-14 | 2020-12-11 | 큐라데브 파마 프라이버트 리미티드 | 키누레닌 경로의 억제제 |
| EP3082802B1 (en) | 2013-12-03 | 2020-02-26 | Iomet Pharma Ltd. | Tryptophan-2,3-dioxygenase (tdo) and/or indolamine-2,3-dioxygenase (ido) inhibitors and their use |
| KR20250007032A (ko) | 2014-08-13 | 2025-01-13 | 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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2017
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2023
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