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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| CN109952300B (zh) | 2016-09-24 | 2022-01-18 | 百济神州有限公司 | 5或8-取代的咪唑并[1,5-a]吡啶 |
| KR20190084053A (ko) | 2016-10-13 | 2019-07-15 | 주노 쎄러퓨티크스 인코퍼레이티드 | 트립토판 대사 경로 조절인자 관련 면역 치료 방법 및 조성물 |
| EP3570832A4 (en) | 2017-01-17 | 2020-06-10 | Board Of Regents, The University Of Texas System | NOVEL COMPOUNDS USEFUL AS INHIBITORS OF INDOLEAMINE 2,3-DIOXYGENASE AND / OR TRYPTOPHANE 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 |
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| JP6912016B1 (ja) * | 2020-04-10 | 2021-07-28 | 小野薬品工業株式会社 | Ｓｔｉｎｇ作動化合物 |
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| KR20170034439A (ko) | 2014-08-13 | 2017-03-28 | 오클랜드 유니서비시즈 리미티드 | 트립토판 디옥시게나제 (ido1 및 tdo)의 억제제 및 치료에서 이들의 용도 |
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