JP2010540412A5 - - Google Patents
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- Publication number
- JP2010540412A5 JP2010540412A5 JP2010512025A JP2010512025A JP2010540412A5 JP 2010540412 A5 JP2010540412 A5 JP 2010540412A5 JP 2010512025 A JP2010512025 A JP 2010512025A JP 2010512025 A JP2010512025 A JP 2010512025A JP 2010540412 A5 JP2010540412 A5 JP 2010540412A5
- Authority
- JP
- Japan
- Prior art keywords
- solution
- water
- added
- brs
- fluoro
- 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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- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LPXPTNMVRIOKMN-UHFFFAOYSA-M Sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- GYHMKJMKSFLHOF-UHFFFAOYSA-N (2-fluoro-3-methylphenyl)hydrazine Chemical compound CC1=CC=CC(NN)=C1F GYHMKJMKSFLHOF-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WFZUBZAEFXETBF-UHFFFAOYSA-N 2-fluoro-3-methylaniline Chemical compound CC1=CC=CC(N)=C1F WFZUBZAEFXETBF-UHFFFAOYSA-N 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L Tin(II) chloride Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
Description
参考例185
(2−フルオロ−3−メチルフェニル)ヒドラジン
亜硝酸ナトリウム(28.7g)の水(100mL)溶液に2−フルオロ−3−メチルアニリン(40g)の濃塩酸(640mL)溶液を−20℃で滴下して加えた。同温度で1時間撹拌した後、塩化スズ(II)(121g)の濃塩酸(200mL)溶液を−20℃で滴下して加えた。0℃で2時間撹拌した後、生じた固体をろ過し、水およびヘキサンで洗浄した。得られた固体を水(500mL)に溶解し、pHが12になるまで2mol/L水酸化ナトリウム水溶液を加え、ジクロロメタンで2回抽出した。抽出液を無水硫酸ナトリウムで乾燥し減圧濃縮することで、表題化合物を白色固体として得た(28.4g,収率63%)。
1H−NMR(CDCl3)δ:2.24(3H,d,J=2.4Hz),3.54(2H,brs),5.30(1H,brs),6.59−6.63(1H,m),6.89(1H,dt,J=7.8,2.0Hz),6.94−6.99(1H,m).
(2−フルオロ−3−メチルフェニル)ヒドラジン
亜硝酸ナトリウム(28.7g)の水(100mL)溶液に2−フルオロ−3−メチルアニリン(40g)の濃塩酸(640mL)溶液を−20℃で滴下して加えた。同温度で1時間撹拌した後、塩化スズ(II)(121g)の濃塩酸(200mL)溶液を−20℃で滴下して加えた。0℃で2時間撹拌した後、生じた固体をろ過し、水およびヘキサンで洗浄した。得られた固体を水(500mL)に溶解し、pHが12になるまで2mol/L水酸化ナトリウム水溶液を加え、ジクロロメタンで2回抽出した。抽出液を無水硫酸ナトリウムで乾燥し減圧濃縮することで、表題化合物を白色固体として得た(28.4g,収率63%)。
1H−NMR(CDCl3)δ:2.24(3H,d,J=2.4Hz),3.54(2H,brs),5.30(1H,brs),6.59−6.63(1H,m),6.89(1H,dt,J=7.8,2.0Hz),6.94−6.99(1H,m).
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2010512025A JP5345140B2 (ja) | 2007-09-28 | 2008-09-24 | プロトンポンプ阻害剤としての5員複素環化合物 |
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2007256274 | 2007-09-28 | ||
JP2007256274 | 2007-09-28 | ||
JP2008218076 | 2008-08-27 | ||
JP2008218076 | 2008-08-27 | ||
JP2010512025A JP5345140B2 (ja) | 2007-09-28 | 2008-09-24 | プロトンポンプ阻害剤としての5員複素環化合物 |
PCT/JP2008/067784 WO2009041705A2 (en) | 2007-09-28 | 2008-09-24 | 5-membered heterocyclic compounds as proton pump inhibitors |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2010540412A JP2010540412A (ja) | 2010-12-24 |
JP2010540412A5 true JP2010540412A5 (ja) | 2011-07-21 |
JP5345140B2 JP5345140B2 (ja) | 2013-11-20 |
Family
ID=40512007
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010512025A Active JP5345140B2 (ja) | 2007-09-28 | 2008-09-24 | プロトンポンプ阻害剤としての5員複素環化合物 |
Country Status (9)
Country | Link |
---|---|
US (1) | US20090156642A1 (ja) |
EP (1) | EP2190822B1 (ja) |
JP (1) | JP5345140B2 (ja) |
KR (1) | KR101558011B1 (ja) |
AR (1) | AR068538A1 (ja) |
CL (1) | CL2008002834A1 (ja) |
PE (1) | PE20090709A1 (ja) |
TW (1) | TW200920366A (ja) |
WO (1) | WO2009041705A2 (ja) |
Families Citing this family (18)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101559597B1 (ko) * | 2007-09-28 | 2015-10-12 | 다케다 야쿠힌 고교 가부시키가이샤 | 5―원 헤테로시클릭 화합물 |
US9186411B2 (en) | 2008-07-28 | 2015-11-17 | Takeda Pharmaceutical Company Limited | Pharmaceutical composition |
AR073136A1 (es) | 2008-08-27 | 2010-10-13 | Takeda Pharmaceutical | Compuestos de pirrol |
CA2756086A1 (en) | 2009-03-26 | 2010-09-30 | Takeda Pharmaceutical Company Limited | Pyrazole compound |
WO2011004882A1 (ja) | 2009-07-09 | 2011-01-13 | ラクオリア創薬株式会社 | 消化管運動異常が関与する疾患を治療するためのアシッドポンプ拮抗剤 |
JP2013517295A (ja) | 2010-01-19 | 2013-05-16 | セラヴァンス, インコーポレーテッド | 二重に作用するチオフェン、ピロール、チアゾールおよびフラン抗高血圧症薬 |
US10039813B2 (en) | 2012-02-07 | 2018-08-07 | Massachusetts Institute Of Technology | Use of antagonists of ghrelin or ghrelin receptor to prevent or treat stress-sensitive psychiatric illness |
NZ703528A (en) | 2012-06-27 | 2016-08-26 | Takeda Pharmaceutical | Liquid preparations of amines and organic acids stabilized by salts |
US9724396B2 (en) | 2013-03-15 | 2017-08-08 | Massachusetts Institute Of Technology | Use of antagonists of growth hormone or growth hormone receptor to prevent or treat stress-sensitive psychiatric illness |
WO2014144878A2 (en) * | 2013-03-15 | 2014-09-18 | The Scripps Research Institute | Novel thiol & amino modifying reagents for protein chemistry and methods of use thereof |
WO2016138099A1 (en) | 2015-02-24 | 2016-09-01 | Massachusetts Institute Of Technology | Use of ghrelin or functional ghrelin receptor agonists to prevent and treat stress-sensitive psychiatric illness |
CN108191830B (zh) * | 2016-06-30 | 2019-06-14 | 珠海赛隆药业股份有限公司(长沙)医药研发中心 | 一种富马酸沃诺拉赞中间体ⅳ及其制备方法 |
CN108203430A (zh) * | 2016-12-16 | 2018-06-26 | 天地人和生物科技有限公司 | 一种新型可逆性质子泵抑制剂及其制备方法和用途 |
JP7119001B2 (ja) | 2017-04-24 | 2022-08-16 | バイエル・アクチエンゲゼルシヤフト | 有害生物防除剤としての縮合二環式ヘテロ環式化合物誘導体 |
CN112830920A (zh) * | 2019-11-25 | 2021-05-25 | 杭州华东医药集团新药研究院有限公司 | 一种杂环衍生物、其药物组合物及用途 |
GB201919213D0 (en) * | 2019-12-23 | 2020-02-05 | Ucb Biopharma Sprl | Dihydrocyclopenta-Isoquinoline-Sulfanamide derivatives compounds |
CN111943932B (zh) * | 2020-08-06 | 2023-07-14 | 四川国康药业有限公司 | 一种可以治疗消化性溃疡的3-吡啶磺酰-1-n-杂吡咯衍生物及其制备方法和用途 |
CN113620930B (zh) * | 2021-07-12 | 2022-08-16 | 南京烁慧医药科技有限公司 | 一种含磺酰胺结构的化合物及其制备方法和应用、一种药物组合物及应用 |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3285991A (en) * | 1963-03-26 | 1966-11-15 | Union Carbide Corp | Polyepoxides cured with the reaction product of a dihydroxydiphenylsul-fone, an amine, and an aldehyde |
WO1996010019A1 (fr) * | 1994-09-26 | 1996-04-04 | Shionogi & Co., Ltd. | Derive imidazole |
CA2493618A1 (en) * | 2002-08-01 | 2004-02-12 | Nitromed, Inc. | Nitrosated proton pump inhibitors, compositions and methods of use |
EP1628957B1 (en) * | 2003-05-26 | 2010-09-29 | Takeda Pharmaceutical Company Limited | Sulfopyrroles |
JP5173192B2 (ja) * | 2004-09-30 | 2013-03-27 | 武田薬品工業株式会社 | プロトンポンプ阻害薬 |
FR2881744B1 (fr) * | 2005-02-09 | 2007-04-27 | Sanofi Aventis Sa | Derives de n-[(4,5-diphenyl-2-thienyl)methyl]amine, leur preparation et leur application en therapeutique |
RS52473B9 (sr) * | 2005-08-30 | 2019-07-31 | Takeda Pharmaceuticals Co | 1-heterociklilsulfonil, 2-aminometil, 5-(hetero-)aril supstituisani derivati 1-h-pirola kao inhibitori sekrecije kiseline |
FR2894578B1 (fr) * | 2005-12-12 | 2008-02-01 | Sanofi Aventis Sa | Derives heterocycliques, leur preparation et leur application en therapeutique. |
US7994205B2 (en) * | 2006-03-31 | 2011-08-09 | Takeda Pharmaceutical Company Limited | Aryl-or heteroaryl-sulfonyl compounds as acid secretion inhibitors |
KR101559597B1 (ko) * | 2007-09-28 | 2015-10-12 | 다케다 야쿠힌 고교 가부시키가이샤 | 5―원 헤테로시클릭 화합물 |
-
2008
- 2008-09-24 KR KR1020107009249A patent/KR101558011B1/ko active IP Right Grant
- 2008-09-24 EP EP08834057.5A patent/EP2190822B1/en active Active
- 2008-09-24 US US12/284,636 patent/US20090156642A1/en not_active Abandoned
- 2008-09-24 TW TW097136593A patent/TW200920366A/zh unknown
- 2008-09-24 CL CL2008002834A patent/CL2008002834A1/es unknown
- 2008-09-24 JP JP2010512025A patent/JP5345140B2/ja active Active
- 2008-09-24 AR ARP080104134A patent/AR068538A1/es unknown
- 2008-09-24 WO PCT/JP2008/067784 patent/WO2009041705A2/en active Application Filing
- 2008-09-24 PE PE2008001664A patent/PE20090709A1/es not_active Application Discontinuation
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