JP2001114780A5 - - Google Patents
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- JP2001114780A5 JP2001114780A5 JP1999295214A JP29521499A JP2001114780A5 JP 2001114780 A5 JP2001114780 A5 JP 2001114780A5 JP 1999295214 A JP1999295214 A JP 1999295214A JP 29521499 A JP29521499 A JP 29521499A JP 2001114780 A5 JP2001114780 A5 JP 2001114780A5
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- JP
- Japan
- Prior art keywords
- compound
- mmol
- nmr
- added
- yield
- 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.)
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- 150000001875 compounds Chemical class 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000000967 suction filtration Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- OQGUQRDSLVDCRT-UHFFFAOYSA-N (4-methylsulfanylphenoxy)boronic acid Chemical compound CSC1=CC=C(OB(O)O)C=C1 OQGUQRDSLVDCRT-UHFFFAOYSA-N 0.000 description 2
- ICRHXBNAKSHNRD-UHFFFAOYSA-N 2-oxo-3,4-dihydro-1h-quinoline-6-sulfonyl chloride Chemical compound N1C(=O)CCC2=CC(S(=O)(=O)Cl)=CC=C21 ICRHXBNAKSHNRD-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- RJMWVQGNEFWEQI-UHFFFAOYSA-N CC1=C(N2C(=N1)CCC3=C2C=CC(=C3)S(=O)(=O)C)C4=CC=C(C=C4)F Chemical compound CC1=C(N2C(=N1)CCC3=C2C=CC(=C3)S(=O)(=O)C)C4=CC=C(C=C4)F RJMWVQGNEFWEQI-UHFFFAOYSA-N 0.000 description 2
- CVHILJJVMXFNIY-UHFFFAOYSA-N CC1=C(N2C(=N1)CCC3=C2C=CC(=C3)S(=O)(=O)C)C4=CC=C(C=C4)SC Chemical compound CC1=C(N2C(=N1)CCC3=C2C=CC(=C3)S(=O)(=O)C)C4=CC=C(C=C4)SC CVHILJJVMXFNIY-UHFFFAOYSA-N 0.000 description 2
- REUGJGWVZXYXFN-UHFFFAOYSA-N CC1=C(N2C(=N1)CSC3=C2C=CC(=C3)S(=O)(=O)C)Br Chemical compound CC1=C(N2C(=N1)CSC3=C2C=CC(=C3)S(=O)(=O)C)Br REUGJGWVZXYXFN-UHFFFAOYSA-N 0.000 description 2
- NXMAEORTQDGKOF-UHFFFAOYSA-N COC1=CC=C(C=C1)C2=NC(=C3N2C4=C(C=C(C=C4)S(=O)(=O)C)OC3)C(F)(F)F Chemical compound COC1=CC=C(C=C1)C2=NC(=C3N2C4=C(C=C(C=C4)S(=O)(=O)C)OC3)C(F)(F)F NXMAEORTQDGKOF-UHFFFAOYSA-N 0.000 description 2
- IQHGEAURCLJHMC-UHFFFAOYSA-N COC1=CC=C(C=C1)C2=NC(=C3N2C4=C(CC3)C=C(C=C4)S(=O)(=O)C)COCC5=CC=CC=C5 Chemical compound COC1=CC=C(C=C1)C2=NC(=C3N2C4=C(CC3)C=C(C=C4)S(=O)(=O)C)COCC5=CC=CC=C5 IQHGEAURCLJHMC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- PHBVXHIVWULVNF-UHFFFAOYSA-N (4-fluorophenoxy)boronic acid Chemical compound OB(O)OC1=CC=C(F)C=C1 PHBVXHIVWULVNF-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 description 1
- VQOOZPLCVZJMTM-UHFFFAOYSA-N CC1=C(N2C(=N1)COC3=C2C=CC(=C3)SC)C4=CC=C(C=C4)F Chemical compound CC1=C(N2C(=N1)COC3=C2C=CC(=C3)SC)C4=CC=C(C=C4)F VQOOZPLCVZJMTM-UHFFFAOYSA-N 0.000 description 1
- WEAXIIDEOCIAKR-UHFFFAOYSA-N CS(=O)(=O)C1=CC=C(C=C1)OB(O)O Chemical compound CS(=O)(=O)C1=CC=C(C=C1)OB(O)O WEAXIIDEOCIAKR-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- -1 Lactam compound Chemical class 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000007875 V-40 Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- QGPGUZIKJKOKRF-UHFFFAOYSA-M potassium;acetonitrile;dihydrogen phosphate Chemical compound [K+].CC#N.OP(O)([O-])=O QGPGUZIKJKOKRF-UHFFFAOYSA-M 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UYCAUPASBSROMS-AWQJXPNKSA-M sodium;2,2,2-trifluoroacetate Chemical compound [Na+].[O-][13C](=O)[13C](F)(F)F UYCAUPASBSROMS-AWQJXPNKSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29521499A JP4409680B2 (ja) | 1999-10-18 | 1999-10-18 | 三環性縮合イミダゾール誘導体 |
| PCT/JP2000/007201 WO2001029038A1 (en) | 1999-10-18 | 2000-10-18 | Tricyclic fused-imidazole derivatives |
| AU79470/00A AU7947000A (en) | 1999-10-18 | 2000-10-18 | Tricyclic fused-imidazole derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP29521499A JP4409680B2 (ja) | 1999-10-18 | 1999-10-18 | 三環性縮合イミダゾール誘導体 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001114780A JP2001114780A (ja) | 2001-04-24 |
| JP2001114780A5 true JP2001114780A5 (https=) | 2006-03-23 |
| JP4409680B2 JP4409680B2 (ja) | 2010-02-03 |
Family
ID=17817687
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP29521499A Expired - Fee Related JP4409680B2 (ja) | 1999-10-18 | 1999-10-18 | 三環性縮合イミダゾール誘導体 |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP4409680B2 (https=) |
| AU (1) | AU7947000A (https=) |
| WO (1) | WO2001029038A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102006051796A1 (de) * | 2006-11-03 | 2008-05-08 | Merck Patent Gmbh | Triaza-benzo[e]azulenderivate |
| WO2013055793A1 (en) | 2011-10-12 | 2013-04-18 | University Of Pittsburg-Of The Commonwealth System Of Higher Education | Small molecules targeting androgen receptor nuclear localization and/or level in prostate cancer |
| CN102898425B (zh) * | 2012-10-30 | 2014-10-08 | 黑龙江八一农垦大学 | 4,5-二氢咪唑[1,2-a]喹啉衍生物及其应用 |
| JP6523267B2 (ja) * | 2013-06-24 | 2019-05-29 | 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 | Ｆｓｈｒの調節剤としてのイミダゾール化合物及びその使用 |
| US20160257657A1 (en) | 2013-09-20 | 2016-09-08 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer |
| CA2924527C (en) | 2013-09-20 | 2022-07-12 | University Of Pittsburgh - Of The Commonwealth System Of Higher Education | Compounds for treating prostate cancer |
| US9527835B2 (en) | 2014-02-13 | 2016-12-27 | Incyte Corporation | Cyclopropylamines as LSD1 inhibitors |
| SI3105218T1 (sl) | 2014-02-13 | 2019-11-29 | Incyte Corp | Ciklopropilamini kot inhibitorji LSD1 |
| MX373103B (es) | 2014-02-13 | 2020-04-17 | Incyte Holdings Corp | Ciclopropilaminas como inhibidores de desmetilasa específica de lisina 1 (lsd1). |
| EP3105219B9 (en) | 2014-02-13 | 2018-10-03 | Incyte Corporation | Cyclopropylamines as lsd1 inhibitors |
| 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 |
| WO2016007727A1 (en) | 2014-07-10 | 2016-01-14 | 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 |
| EP3277689B1 (en) | 2015-04-03 | 2019-09-04 | Incyte Corporation | Heterocyclic compounds as lsd1 inhibitors |
| LT3334709T (lt) | 2015-08-12 | 2025-03-10 | Incyte Holdings Corporation | Lsd1 inhibitoriaus druskos |
| US10980806B2 (en) | 2016-03-24 | 2021-04-20 | University of Pittsburgh—of the Commonwealth System of Higher Education | Small molecule inhibitors of the nuclear translocation of androgen receptor for the treatment of castration-resistant prostate cancer |
| JP6999574B2 (ja) | 2016-04-22 | 2022-01-18 | インサイト・コーポレイション | Ｌｓｄ１阻害剤の製剤 |
| WO2020047198A1 (en) | 2018-08-31 | 2020-03-05 | Incyte Corporation | Salts of an lsd1 inhibitor and processes for preparing the same |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8422918D0 (en) * | 1984-09-11 | 1984-10-17 | May & Baker Ltd | Compositions of matter |
| US5547975A (en) * | 1994-09-20 | 1996-08-20 | Talley; John J. | Benzopyranopyrazolyl derivatives for the treatment of inflammation |
-
1999
- 1999-10-18 JP JP29521499A patent/JP4409680B2/ja not_active Expired - Fee Related
-
2000
- 2000-10-18 AU AU79470/00A patent/AU7947000A/en not_active Abandoned
- 2000-10-18 WO PCT/JP2000/007201 patent/WO2001029038A1/ja not_active Ceased
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