JP2013522213A - ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造 - Google Patents
ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造 Download PDFInfo
- Publication number
- JP2013522213A JP2013522213A JP2012557188A JP2012557188A JP2013522213A JP 2013522213 A JP2013522213 A JP 2013522213A JP 2012557188 A JP2012557188 A JP 2012557188A JP 2012557188 A JP2012557188 A JP 2012557188A JP 2013522213 A JP2013522213 A JP 2013522213A
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- JP
- Japan
- Prior art keywords
- formula
- compound
- solvent
- molar ratio
- reaction
- 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.)
- Pending
Links
- 0 *C(*)=NC(CCO1)C1=O Chemical compound *C(*)=NC(CCO1)C1=O 0.000 description 7
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
- C07C321/02—Thiols having mercapto groups bound to acyclic carbon atoms
- C07C321/08—Thiols having mercapto groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C391/00—Compounds containing selenium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/06—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings
- C07D265/08—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D265/10—1,3-Oxazines; Hydrogenated 1,3-oxazines not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen atoms directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US31202410P | 2010-03-09 | 2010-03-09 | |
| US31201210P | 2010-03-09 | 2010-03-09 | |
| US31202010P | 2010-03-09 | 2010-03-09 | |
| US61/312,024 | 2010-03-09 | ||
| US61/312,020 | 2010-03-09 | ||
| US61/312,012 | 2010-03-09 | ||
| US33391510P | 2010-05-12 | 2010-05-12 | |
| US61/333,915 | 2010-05-12 | ||
| PCT/US2011/027642 WO2011112649A1 (en) | 2010-03-09 | 2011-03-09 | Preparation of methionine or selenomethionine from homoserine via a lactone intermediate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2013522213A true JP2013522213A (ja) | 2013-06-13 |
Family
ID=44560584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012557188A Pending JP2013522213A (ja) | 2010-03-09 | 2011-03-09 | ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造 |
Country Status (10)
| Country | Link |
|---|---|
| US (5) | US8865920B2 (enExample) |
| EP (1) | EP2545032A4 (enExample) |
| JP (1) | JP2013522213A (enExample) |
| KR (1) | KR20130006464A (enExample) |
| CN (1) | CN102869646A (enExample) |
| BR (1) | BR112012022506A2 (enExample) |
| CA (1) | CA2791879A1 (enExample) |
| IN (1) | IN2012KN02804A (enExample) |
| MX (1) | MX2012010218A (enExample) |
| WO (2) | WO2011112648A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013522213A (ja) | 2010-03-09 | 2013-06-13 | ノーバス・インターナショナル・インコーポレイテッド | ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造 |
| CN102558005A (zh) * | 2012-01-11 | 2012-07-11 | 张家港阿拉宁生化技术有限公司 | 一种对环境友好的合成硒代蛋氨酸的方法 |
| CN102898339B (zh) * | 2012-10-29 | 2013-11-13 | 苏州二叶制药有限公司 | 一种硫普罗宁的制备方法 |
| WO2015141886A1 (ko) * | 2014-03-20 | 2015-09-24 | 씨제이제일제당(주) | 미생물 유래의 o-아실호모세린으로부터 바이오 유래 호모세린락톤 염산염 및 바이오 유래 유기산을 제조하는 방법 |
| US9834491B2 (en) | 2013-03-20 | 2017-12-05 | Cj Cheiljedang Corporation | Method for producing bio-based homoserine lactone and bio-based organic acid from O-acyl homoserine produced by microorganisms |
| CN104356099B (zh) * | 2014-11-19 | 2016-05-11 | 郑州大学 | 高丝氨酸内酯类化合物、其制备方法及其应用 |
| CN104557581A (zh) * | 2014-12-25 | 2015-04-29 | 吉尔生化(上海)有限公司 | 一种高丝氨酸的制备方法 |
| CN105646302B (zh) * | 2016-02-05 | 2018-01-12 | 宁夏紫光天化蛋氨酸有限责任公司 | 一种甲硫醇盐的生产方法 |
| CN108516991A (zh) * | 2018-05-28 | 2018-09-11 | 山东省农药科学研究院 | 一种精草铵膦的制备方法 |
| CN108484666B (zh) * | 2018-05-28 | 2021-02-26 | 山东省农药科学研究院 | 一种精草铵膦的合成方法 |
| CN109535052B (zh) * | 2018-12-07 | 2021-07-16 | 河南希百康健康产业有限公司 | 一种l-硒甲基硒代半胱氨酸的制备方法 |
| CN109438307A (zh) * | 2018-12-07 | 2019-03-08 | 济源市万洋华康生物科技有限公司 | 一种l-硒代蛋氨酸的制备方法 |
| MY204363A (en) | 2019-01-11 | 2024-08-26 | Cj Cheiljedang Corp | L-glufosinate intermediate and l-glufosinate preparation method |
| CN109796329A (zh) * | 2019-03-26 | 2019-05-24 | 上海化工研究院有限公司 | 一种13C标记α-氨基丁酸的合成方法 |
| CN110204517A (zh) * | 2019-07-12 | 2019-09-06 | 利尔化学股份有限公司 | 一种(s)-(2-氧代四氢呋喃-3-基)氨基甲酸酯的制备方法 |
| CN110683976A (zh) * | 2019-11-04 | 2020-01-14 | 济源市万洋华康生物科技有限公司 | 一种制备(r)-硒甲基硒代半胱氨酸的方法 |
| EP4151643A1 (en) | 2021-09-16 | 2023-03-22 | Evonik Operations GmbH | Improved process for production of phosphoesters of glufosinate precursors |
| US20250333373A1 (en) * | 2022-05-24 | 2025-10-30 | Vulpes Agricultural Corp. | L-2-Amino-4-Halobutyric Acid Derivative-L-Tartrate and Preparation Method Thereof |
| CN116143648A (zh) * | 2022-12-05 | 2023-05-23 | 河北远大九孚生物科技有限公司 | 一种n-乙酰-l-苯丙氨酸的合成方法 |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5132527A (enExample) * | 1974-07-09 | 1976-03-19 | Hoechst Ag | |
| JPS539715A (en) * | 1976-07-13 | 1978-01-28 | Ajinomoto Co Inc | Crystallization of dl-acetylmethionine |
| JPS5452033A (en) * | 1977-09-29 | 1979-04-24 | Ajinomoto Co Inc | Preparation of selenoamino acid |
| JPS58150582A (ja) * | 1982-03-03 | 1983-09-07 | Toray Ind Inc | α−(ジフエニルメチレンアミノ)ブチロラクトンおよびその製造法 |
| JPS62267260A (ja) * | 1986-05-08 | 1987-11-19 | ヌブス インターナショナル,インコーポレイテッド | アルキルチオアルカノエ−ト塩の製造方法 |
| JPH01502021A (ja) * | 1986-03-27 | 1989-07-13 | ジ・アップジョン・カンパニー | ラクタムプソイドジペプチドを有するレニン抑制物質 |
| JPH0272156A (ja) * | 1988-09-07 | 1990-03-12 | Konica Corp | 4−置換チオ酪酸系化合物の製造方法 |
| WO1996006068A1 (en) * | 1994-08-22 | 1996-02-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzene compound and medicinal use thereof |
| JPH11236333A (ja) * | 1997-12-30 | 1999-08-31 | Pfizer Prod Inc | 抗ガン剤として有用なイミダゾリン−4−オン誘導体 |
| JP2001002668A (ja) * | 1999-06-18 | 2001-01-09 | Mitsubishi Chemicals Corp | ホモセリンラクトンの製造方法 |
| JP2007099778A (ja) * | 1995-12-18 | 2007-04-19 | Degussa Gmbh | メチオニンおよびその塩の製造方法 |
| JP2009524615A (ja) * | 2006-01-28 | 2009-07-02 | エボニック デグサ ゲーエムベーハー | ホモセリンからのメチオニンの製法 |
| JP2010501516A (ja) * | 2006-08-24 | 2010-01-21 | エボニック デグサ ゲーエムベーハー | D,l−2−ヒドロキシ−4−アルキルチオ酪酸の製造方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2678601B1 (fr) | 1991-07-01 | 1993-10-22 | Commissariat Energie Atomique | Procede de preparation de sulfures et d'acides amines marques au soufre 35. |
| FR2750132B1 (fr) | 1996-06-20 | 1998-08-14 | Rhone Poulenc Chimie | Procede d'acylation d'un ether ou thioether aromatique |
| US20030083383A1 (en) * | 1999-08-16 | 2003-05-01 | Spallholz Julian E. | Method of using synthetic L-Se-methylselenocysteine as a nutriceutical and a method of its synthesis |
| IN191266B (enExample) | 1999-09-16 | 2003-10-18 | Council Scient Ind Res | |
| DK1339705T3 (da) * | 2000-11-30 | 2006-10-09 | Basf Ag | Fremgangsmåde til fremstilling af liponsyre og dihydroliponsyre |
| FR2873376B1 (fr) * | 2004-07-23 | 2006-11-24 | Tetrahedron Sas | Nouveaux seleno-hydroxyacides et leurs derives, applications en nutrition, cosmetique et pharmacie |
| CN1295214C (zh) * | 2005-01-21 | 2007-01-17 | 山西大学 | 一种硒代蛋氨酸的合成方法 |
| US7586003B2 (en) | 2005-07-14 | 2009-09-08 | Zinpro Corporation | Derivatives of seleno-amino acids |
| FR2907785B1 (fr) | 2006-10-27 | 2009-01-16 | Tetrahedron Sas | Procede de preparation de l'acide 2-hydroxy-4-methylselenobutyrique, seul ou en melange avec son analogue soufre, ainsi que leurs utilisations en nutrition, en particulier en nutrition animale |
| EP2520645B1 (en) * | 2007-04-11 | 2015-01-14 | CJ CheilJedang Corporation | Compositions and methods of producing methionine |
| US7906513B2 (en) * | 2007-04-26 | 2011-03-15 | Enanta Pharmaceuticals, Inc. | Hydrazide-containing hepatitis C serine protease inhibitors |
| JP2013522213A (ja) | 2010-03-09 | 2013-06-13 | ノーバス・インターナショナル・インコーポレイテッド | ラクトン中間体を経由するホモセリンからのメチオニンまたはセレノメチオニンの製造 |
-
2011
- 2011-03-09 JP JP2012557188A patent/JP2013522213A/ja active Pending
- 2011-03-09 EP EP11753971.8A patent/EP2545032A4/en not_active Withdrawn
- 2011-03-09 BR BR112012022506A patent/BR112012022506A2/pt not_active IP Right Cessation
- 2011-03-09 CN CN2011800233788A patent/CN102869646A/zh active Pending
- 2011-03-09 US US13/581,887 patent/US8865920B2/en active Active
- 2011-03-09 MX MX2012010218A patent/MX2012010218A/es unknown
- 2011-03-09 US US13/043,767 patent/US8742170B2/en active Active
- 2011-03-09 US US13/043,740 patent/US8476427B2/en active Active
- 2011-03-09 IN IN2804KON2012 patent/IN2012KN02804A/en unknown
- 2011-03-09 KR KR1020127026064A patent/KR20130006464A/ko not_active Withdrawn
- 2011-03-09 WO PCT/US2011/027641 patent/WO2011112648A1/en not_active Ceased
- 2011-03-09 WO PCT/US2011/027642 patent/WO2011112649A1/en not_active Ceased
- 2011-03-09 CA CA2791879A patent/CA2791879A1/en not_active Abandoned
-
2012
- 2012-08-30 US US13/599,094 patent/US20130006014A1/en not_active Abandoned
-
2013
- 2013-03-20 US US13/847,668 patent/US20130211078A1/en not_active Abandoned
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5132527A (enExample) * | 1974-07-09 | 1976-03-19 | Hoechst Ag | |
| JPS539715A (en) * | 1976-07-13 | 1978-01-28 | Ajinomoto Co Inc | Crystallization of dl-acetylmethionine |
| JPS5452033A (en) * | 1977-09-29 | 1979-04-24 | Ajinomoto Co Inc | Preparation of selenoamino acid |
| JPS58150582A (ja) * | 1982-03-03 | 1983-09-07 | Toray Ind Inc | α−(ジフエニルメチレンアミノ)ブチロラクトンおよびその製造法 |
| JPH01502021A (ja) * | 1986-03-27 | 1989-07-13 | ジ・アップジョン・カンパニー | ラクタムプソイドジペプチドを有するレニン抑制物質 |
| JPS62267260A (ja) * | 1986-05-08 | 1987-11-19 | ヌブス インターナショナル,インコーポレイテッド | アルキルチオアルカノエ−ト塩の製造方法 |
| JPH0272156A (ja) * | 1988-09-07 | 1990-03-12 | Konica Corp | 4−置換チオ酪酸系化合物の製造方法 |
| WO1996006068A1 (en) * | 1994-08-22 | 1996-02-29 | Yoshitomi Pharmaceutical Industries, Ltd. | Benzene compound and medicinal use thereof |
| JP2007099778A (ja) * | 1995-12-18 | 2007-04-19 | Degussa Gmbh | メチオニンおよびその塩の製造方法 |
| JPH11236333A (ja) * | 1997-12-30 | 1999-08-31 | Pfizer Prod Inc | 抗ガン剤として有用なイミダゾリン−4−オン誘導体 |
| JP2001002668A (ja) * | 1999-06-18 | 2001-01-09 | Mitsubishi Chemicals Corp | ホモセリンラクトンの製造方法 |
| JP2009524615A (ja) * | 2006-01-28 | 2009-07-02 | エボニック デグサ ゲーエムベーハー | ホモセリンからのメチオニンの製法 |
| JP2010501516A (ja) * | 2006-08-24 | 2010-01-21 | エボニック デグサ ゲーエムベーハー | D,l−2−ヒドロキシ−4−アルキルチオ酪酸の製造方法 |
Non-Patent Citations (5)
| Title |
|---|
| JPN6014000592; Journal of Medicinal Chemistry (1988), 31(7), 1369-1376 * |
| JPN6014000593; Tetrahedron (2006), 62(44), 10332-10343 * |
| JPN6014000594; Journal of the American Chemical Society (1945), 67(12), 2218-2220 * |
| JPN6014000595; 日本化学雜誌 (1959), 80(8), 927(121)-929(123) * |
| JPN6014024584; Greene T.W. et al: Protective groups in organic synthesis 3rd edition, 1999, pp.586-589 * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20130211078A1 (en) | 2013-08-15 |
| US20130012728A1 (en) | 2013-01-10 |
| MX2012010218A (es) | 2013-01-29 |
| WO2011112649A1 (en) | 2011-09-15 |
| CA2791879A1 (en) | 2011-09-15 |
| EP2545032A4 (en) | 2014-01-01 |
| US8476427B2 (en) | 2013-07-02 |
| BR112012022506A2 (pt) | 2017-09-19 |
| IN2012KN02804A (enExample) | 2015-05-01 |
| US20130006014A1 (en) | 2013-01-03 |
| CN102869646A (zh) | 2013-01-09 |
| EP2545032A1 (en) | 2013-01-16 |
| KR20130006464A (ko) | 2013-01-16 |
| US20110224458A1 (en) | 2011-09-15 |
| WO2011112648A1 (en) | 2011-09-15 |
| US8742170B2 (en) | 2014-06-03 |
| US8865920B2 (en) | 2014-10-21 |
| US20110224430A1 (en) | 2011-09-15 |
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