JP2013537875A5 - - Google Patents
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- Publication number
- JP2013537875A5 JP2013537875A5 JP2013511445A JP2013511445A JP2013537875A5 JP 2013537875 A5 JP2013537875 A5 JP 2013537875A5 JP 2013511445 A JP2013511445 A JP 2013511445A JP 2013511445 A JP2013511445 A JP 2013511445A JP 2013537875 A5 JP2013537875 A5 JP 2013537875A5
- Authority
- JP
- Japan
- Prior art keywords
- mmol
- stirred
- dimethyldecahydroquinoxaline
- reduced pressure
- under reduced
- 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
- 238000004519 manufacturing process Methods 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- -1 (4aS, 8aR) -1- (4-chlorophenyl) -3,3-dimethyldecahydroquinoxaline hydrochloride (4aR, 8aS) -2,2-dimethyldecahydroquinoxaline Chemical compound 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000002198 insoluble material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- BISXCYZIZKDVOM-JWPUTSTISA-N (4as,8as)-2,2-dimethyl-4-(1h-pyrrolo[2,3-b]pyridin-4-yl)-1,3,4a,5,6,7,8,8a-octahydroquinoxaline;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.N([C@H]1CCCC[C@@H]11)C(C)(C)CN1C1=CC=NC2=C1C=CN2 BISXCYZIZKDVOM-JWPUTSTISA-N 0.000 description 1
- LFZGEHLTWWOFMS-AXEKQOJOSA-N (4as,8as)-4-[4-(difluoromethoxy)-3-fluorophenyl]-2,2-dimethyl-1,3,4a,5,6,7,8,8a-octahydroquinoxaline;dihydrochloride Chemical compound Cl.Cl.N([C@H]1CCCC[C@@H]11)C(C)(C)CN1C1=CC=C(OC(F)F)C(F)=C1 LFZGEHLTWWOFMS-AXEKQOJOSA-N 0.000 description 1
- MDEXMBGPIZUUBI-UHFFFAOYSA-N 1,2,3,4,4a,5,6,7,8,8a-decahydroquinoxaline Chemical compound N1CCNC2CCCCC21 MDEXMBGPIZUUBI-UHFFFAOYSA-N 0.000 description 1
- NHDODQWIKUYWMW-UHFFFAOYSA-N 1-bromo-4-chlorobenzene Chemical compound ClC1=CC=C(Br)C=C1 NHDODQWIKUYWMW-UHFFFAOYSA-N 0.000 description 1
- OJZFGANJYRFYMA-MOGJOVFKSA-N 4-[(4as,8as)-3,3-dimethyl-2,4,4a,5,6,7,8,8a-octahydroquinoxalin-1-yl]-2-chlorobenzonitrile;hydrochloride Chemical compound Cl.N([C@H]1CCCC[C@@H]11)C(C)(C)CN1C1=CC=C(C#N)C(Cl)=C1 OJZFGANJYRFYMA-MOGJOVFKSA-N 0.000 description 1
- DOMDQZCKLBEOTD-UHFFFAOYSA-N 4-bromo-1-(difluoromethoxy)-2-fluorobenzene Chemical compound FC(F)OC1=CC=C(Br)C=C1F DOMDQZCKLBEOTD-UHFFFAOYSA-N 0.000 description 1
- AYQBMZNSJPVADT-UHFFFAOYSA-N 4-bromo-2-chlorobenzonitrile Chemical compound ClC1=CC(Br)=CC=C1C#N AYQBMZNSJPVADT-UHFFFAOYSA-N 0.000 description 1
- KTXHQILIXKVUAE-UHFFFAOYSA-N 5-bromo-1-methylindole-2-carbonitrile Chemical compound BrC1=CC=C2N(C)C(C#N)=CC2=C1 KTXHQILIXKVUAE-UHFFFAOYSA-N 0.000 description 1
- 0 C*CC(*N(*)C(C)(*)*)N(*)* Chemical compound C*CC(*N(*)C(C)(*)*)N(*)* 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- OAGYXKDWLCJKOZ-UPVQGACJSA-N [4-[(4as,8as)-3,3-dimethyl-2,4,4a,5,6,7,8,8a-octahydroquinoxalin-1-yl]pyrrolo[2,3-b]pyridin-1-yl]-tri(propan-2-yl)silane Chemical compound C([C@@H]1NC(C)(C)C2)CCC[C@@H]1N2C1=C2C=CN([Si](C(C)C)(C(C)C)C(C)C)C2=NC=C1 OAGYXKDWLCJKOZ-UPVQGACJSA-N 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2013511445A JP5973994B2 (ja) | 2010-09-13 | 2011-09-12 | 複素環化合物 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2010204747 | 2010-09-13 | ||
| JP2010204747 | 2010-09-13 | ||
| JP2013511445A JP5973994B2 (ja) | 2010-09-13 | 2011-09-12 | 複素環化合物 |
| PCT/JP2011/071174 WO2012036253A1 (en) | 2010-09-13 | 2011-09-12 | Heterocyclic compounds for treating or preventing disorders caused by reduced neurotransmission of serotonin, norephnephrine or dopamine. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2013537875A JP2013537875A (ja) | 2013-10-07 |
| JP2013537875A5 true JP2013537875A5 (enExample) | 2014-10-30 |
| JP5973994B2 JP5973994B2 (ja) | 2016-08-23 |
Family
ID=44721008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013511445A Active JP5973994B2 (ja) | 2010-09-13 | 2011-09-12 | 複素環化合物 |
Country Status (29)
| Country | Link |
|---|---|
| US (5) | US9090572B2 (enExample) |
| EP (1) | EP2616460B1 (enExample) |
| JP (1) | JP5973994B2 (enExample) |
| KR (1) | KR101944552B1 (enExample) |
| CN (1) | CN103180312B (enExample) |
| AR (1) | AR082962A1 (enExample) |
| AU (1) | AU2011303009B2 (enExample) |
| BR (1) | BR112013005823B8 (enExample) |
| CA (1) | CA2811080C (enExample) |
| CO (1) | CO6680697A2 (enExample) |
| CY (1) | CY1117026T1 (enExample) |
| DK (1) | DK2616460T3 (enExample) |
| EA (1) | EA024099B1 (enExample) |
| ES (1) | ES2553387T3 (enExample) |
| HR (1) | HRP20151282T1 (enExample) |
| HU (1) | HUE025873T2 (enExample) |
| IL (1) | IL225105A (enExample) |
| MX (1) | MX2013002530A (enExample) |
| MY (1) | MY164789A (enExample) |
| NZ (1) | NZ608117A (enExample) |
| PH (1) | PH12013500443A1 (enExample) |
| PL (1) | PL2616460T3 (enExample) |
| PT (1) | PT2616460E (enExample) |
| SG (1) | SG188402A1 (enExample) |
| SI (1) | SI2616460T1 (enExample) |
| TW (1) | TWI526434B (enExample) |
| UA (1) | UA111950C2 (enExample) |
| WO (1) | WO2012036253A1 (enExample) |
| ZA (1) | ZA201301718B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2013137479A1 (en) * | 2012-03-12 | 2013-09-19 | Otsuka Pharmaceutical Co., Ltd. | Decahydroquinoxaline derivatives and analogs thereof |
| CN104364236B (zh) * | 2012-05-09 | 2018-01-16 | 拜尔农作物科学股份公司 | 5‑卤代吡唑二氢茚基甲酰胺 |
| WO2014128093A1 (en) | 2013-02-20 | 2014-08-28 | Bayer Pharma Aktiengesellschaft | Substituted-imidazo[1,2-b]pyridazines as mknk1 inhibitors |
| AU2018351559B2 (en) * | 2017-10-19 | 2023-11-16 | Js Innopharm (Shanghai) Ltd. | Heterocyclic compounds, compositions comprising heterocyclic compound, and methods of use thereof |
| US20240409519A1 (en) * | 2021-07-13 | 2024-12-12 | Otsuka Pharmaceutical Co., Ltd. | Hydrogenated quinoxalines |
| CN116554127B (zh) * | 2022-01-28 | 2025-03-21 | 成都麻沸散医药科技有限公司 | 哌嗪取代苯酚类衍生物及其用途 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU390391A1 (ru) | 1971-04-12 | 1973-07-11 | УСТРОЙСТВО дл ИЗМЕРЕНИЯ ДАВЛЕНИЯ | |
| SU390091A1 (ru) * | 1971-07-12 | 1973-07-11 | С. И. Бурмистров, Н. В. Макаревич , Л. Я. Кравченко Днепропетровский химико технологический институт Дзержинского | Способ получения 1-аренсульфонил-4- -арилдекагидрохиноксалинов |
| DE4210941A1 (de) | 1992-04-02 | 1993-10-07 | Bayer Ag | Neue 9-Fluor-7.oxo-7H-pyrido[1,2,3-d,e][1,4]benzoxacin-6-carbonsäuren und -ester |
| DE4337609A1 (de) * | 1993-11-04 | 1995-05-11 | Boehringer Ingelheim Kg | Neue Pyrazincarboxamidderivate, ihre Herstellung und ihre Verwendung in Arzneimitteln |
| EP0876358A1 (en) * | 1996-01-05 | 1998-11-11 | Novartis AG | Herbicidal 1,2,4,6-thiatriazines |
| DK0952154T3 (da) * | 1998-04-16 | 2004-12-13 | Pfizer Prod Inc | N-acyl- og N-aroylaralkylamider |
| IT1312310B1 (it) * | 1999-05-07 | 2002-04-15 | Recordati Ind Chimica E Farma | Uso di antagonisti selettivi del recettore adrenergico a 1b per ilmiglioramento della disfunzione sessuale |
| PE20040804A1 (es) * | 2002-12-19 | 2004-12-31 | Boehringer Ingelheim Pharma | DERIVADOS DE CARBOXAMIDAS COMO INHIBIDORES DEL FACTOR Xa |
| CN101528225B (zh) * | 2006-08-07 | 2013-07-17 | 阿尔巴尼分子研究公司 | 作为5ht3调节剂的2-氨基苯并噁唑羧酰胺 |
| WO2008023239A1 (en) * | 2006-08-23 | 2008-02-28 | Pfizer Products Inc. | Pyrimidone compounds as gsk-3 inhibitors |
| UA108596C2 (xx) * | 2007-11-09 | 2015-05-25 | Інгібітори пептиддеформілази | |
| EP2437600A4 (en) * | 2009-06-03 | 2012-11-07 | Glaxosmithkline Llc | BIS-PYRIDYLPYRIDONE AS MELANIN CONCENTRATION HORMONE RECEPTOR-1 ANTAGONISTS |
| TWM369750U (en) | 2009-06-03 | 2009-12-01 | Yu-Hao Shen | Self-rotation mop structure |
| WO2011068171A1 (ja) * | 2009-12-03 | 2011-06-09 | 第一三共株式会社 | 二環性含窒素飽和へテロ環誘導体 |
-
2011
- 2011-09-12 HU HUE11764005A patent/HUE025873T2/en unknown
- 2011-09-12 CN CN201180044090.9A patent/CN103180312B/zh active Active
- 2011-09-12 MY MYPI2013000848A patent/MY164789A/en unknown
- 2011-09-12 CA CA2811080A patent/CA2811080C/en not_active Expired - Fee Related
- 2011-09-12 US US13/822,589 patent/US9090572B2/en active Active
- 2011-09-12 AR ARP110103315A patent/AR082962A1/es not_active Application Discontinuation
- 2011-09-12 WO PCT/JP2011/071174 patent/WO2012036253A1/en not_active Ceased
- 2011-09-12 JP JP2013511445A patent/JP5973994B2/ja active Active
- 2011-09-12 PL PL11764005T patent/PL2616460T3/pl unknown
- 2011-09-12 NZ NZ608117A patent/NZ608117A/en not_active IP Right Cessation
- 2011-09-12 PT PT117640052T patent/PT2616460E/pt unknown
- 2011-09-12 HR HRP20151282TT patent/HRP20151282T1/hr unknown
- 2011-09-12 ES ES11764005.2T patent/ES2553387T3/es active Active
- 2011-09-12 PH PH1/2013/500443A patent/PH12013500443A1/en unknown
- 2011-09-12 KR KR1020137006245A patent/KR101944552B1/ko not_active Expired - Fee Related
- 2011-09-12 BR BR112013005823A patent/BR112013005823B8/pt not_active IP Right Cessation
- 2011-09-12 SI SI201130714T patent/SI2616460T1/sl unknown
- 2011-09-12 MX MX2013002530A patent/MX2013002530A/es active IP Right Grant
- 2011-09-12 EA EA201390374A patent/EA024099B1/ru not_active IP Right Cessation
- 2011-09-12 SG SG2013016258A patent/SG188402A1/en unknown
- 2011-09-12 EP EP11764005.2A patent/EP2616460B1/en active Active
- 2011-09-12 DK DK11764005.2T patent/DK2616460T3/en active
- 2011-09-12 AU AU2011303009A patent/AU2011303009B2/en not_active Ceased
- 2011-09-13 TW TW100132874A patent/TWI526434B/zh not_active IP Right Cessation
- 2011-12-09 UA UAA201304569A patent/UA111950C2/uk unknown
-
2013
- 2013-03-06 ZA ZA2013/01718A patent/ZA201301718B/en unknown
- 2013-03-06 CO CO13044406A patent/CO6680697A2/es active IP Right Grant
- 2013-03-07 IL IL225105A patent/IL225105A/en active IP Right Grant
-
2015
- 2015-05-06 US US14/705,870 patent/US20160058757A1/en not_active Abandoned
- 2015-12-08 CY CY20151101119T patent/CY1117026T1/el unknown
-
2017
- 2017-04-24 US US15/495,862 patent/US10064879B2/en active Active
-
2018
- 2018-08-30 US US16/118,376 patent/US10603331B2/en active Active
-
2020
- 2020-03-16 US US16/820,652 patent/US11273168B2/en active Active
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