JP2016511278A5 - - Google Patents
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- JP2016511278A5 JP2016511278A5 JP2015562212A JP2015562212A JP2016511278A5 JP 2016511278 A5 JP2016511278 A5 JP 2016511278A5 JP 2015562212 A JP2015562212 A JP 2015562212A JP 2015562212 A JP2015562212 A JP 2015562212A JP 2016511278 A5 JP2016511278 A5 JP 2016511278A5
- Authority
- JP
- Japan
- Prior art keywords
- hydroxybutyrate
- process according
- poly
- alcohol
- ester
- 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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- 238000000034 method Methods 0.000 claims 8
- WHBMMWSBFZVSSR-GSVOUGTGSA-M (R)-3-hydroxybutyrate Chemical compound C[C@@H](O)CC([O-])=O WHBMMWSBFZVSSR-GSVOUGTGSA-M 0.000 claims 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- 238000005809 transesterification reaction Methods 0.000 claims 4
- -1 (R) -3-hydroxybutyrate ester Chemical class 0.000 claims 2
- ALDKXMLLZDHWRZ-UHFFFAOYSA-N bis(2-methoxyethoxy)alumanylium;hydride;sodium Chemical compound [H-].[Na].COCCO[Al+]OCCOC ALDKXMLLZDHWRZ-UHFFFAOYSA-N 0.000 claims 2
- 238000004821 distillation Methods 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 2
- PUPZLCDOIYMWBV-SCSAIBSYSA-N (R)-butane-1,3-diol Chemical compound C[C@@H](O)CCO PUPZLCDOIYMWBV-SCSAIBSYSA-N 0.000 claims 1
- 229920002261 Corn starch Polymers 0.000 claims 1
- 240000000111 Saccharum officinarum Species 0.000 claims 1
- 235000007201 Saccharum officinarum Nutrition 0.000 claims 1
- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3R)-3-hydroxybutyl] (3R)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating Effects 0.000 claims 1
- CROBTXVXNQNKKO-UHFFFAOYSA-N borohydride Chemical compound [BH4-] CROBTXVXNQNKKO-UHFFFAOYSA-N 0.000 claims 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000008120 corn starch Substances 0.000 claims 1
- 238000007871 hydride transfer reaction Methods 0.000 claims 1
- HPQVWDOOUQVBTO-UHFFFAOYSA-N lithium aluminium hydride Substances [Li+].[Al-] HPQVWDOOUQVBTO-UHFFFAOYSA-N 0.000 claims 1
- OCZDCIYGECBNKL-UHFFFAOYSA-N lithium;alumanuide Chemical group [Li+].[AlH4-] OCZDCIYGECBNKL-UHFFFAOYSA-N 0.000 claims 1
- 229910052759 nickel Inorganic materials 0.000 claims 1
- 239000003638 reducing agent Substances 0.000 claims 1
- YOQDYZUWIQVZSF-UHFFFAOYSA-N sodium borohydride Substances [BH4-].[Na+] YOQDYZUWIQVZSF-UHFFFAOYSA-N 0.000 claims 1
- 229910000033 sodium borohydride Inorganic materials 0.000 claims 1
- ODGROJYWQXFQOZ-UHFFFAOYSA-N sodium;boron(1-) Chemical compound [B-].[Na+] ODGROJYWQXFQOZ-UHFFFAOYSA-N 0.000 claims 1
Claims (9)
- (i) ポリ-(R)-3-ヒドロキシブチレートをエステル交換条件下で、ポリ-(R)-3-ヒドロキシブチレートをエステル交換することができるC 1-6 の１価、２価又は３価のアルコールと接触させて、ポリ-(R)-3-ヒドロキシブチレートをエステル交換して(R)-3-ヒドロキシブチレートと前記アルコールのエステルを生成し、
(ii) 工程i)の生成物を第一の部分及び第二の部分に分離し、(R)-3-ヒドロキシブチレートエステルの第一の部分を還元して(R)-1,3-ブタンジオールを生成し、
(iii) エステル交換条件下で工程ii) からの(R)-1,3-ブタンジオールをエステル交換されたエステルの第二の部分と接触させて(R)-3-ヒドロキシブチル-(R)-3-ヒドロキシブチレートを生成することを特徴とする(R)-3-ヒドロキシブチル(R)-3-ヒドロキシブチレートの製造方法。 - ポリ-(R)-3-ヒドロキシブチレートをトウモロコシ澱粉又はサトウキビから得る、請求項１記載の方法。
- ポリ-(R)-3-ヒドロキシブチレートを工程i)でエタノールを使用してエステル交換する、請求項１又は２記載の方法。
- アルコール対ポリ-(R)-3-ヒドロキシブチレートの質量比が1:1 から10:1までである、請求項１から３のいずれか１項記載の方法。
- 工程i)を酸性条件で行なう、請求項１から４のいずれか１項記載の方法。
- 工程i)の生成物を処理して酸を中和し、アルコールを蒸留により除去する、請求項１から５のいずれか１項記載の方法。
- 蒸留を110 ℃〜150 ℃の温度で行なう、請求項６記載の方法。
- 工程ii) における還元が、ヒドリド移動試薬を使用して(R)-3-ヒドロキシブチレートエステルを還元することを含む、請求項１から７のいずれか１項記載の方法。
- 還元剤が水素化リチウムアルミニウム、水素化ナトリウムビス（2-メトキシエトキシ）アルミニウム、ホウ水素化ナトリウム、ホウ水素化ニッケルから選ばれる、請求項８記載の方法。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361783167P | 2013-03-14 | 2013-03-14 | |
| US61/783,167 | 2013-03-14 | ||
| PCT/EP2014/055156 WO2014140308A1 (en) | 2013-03-14 | 2014-03-14 | Process for producing (r)-3-hydroxybutyl (r)-3-hydroxybutyrate |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016511278A JP2016511278A (ja) | 2016-04-14 |
| JP2016511278A5 true JP2016511278A5 (ja) | 2016-07-14 |
| JP6110959B2 JP6110959B2 (ja) | 2017-04-05 |
Family
ID=50336299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015562212A Active JP6110959B2 (ja) | 2013-03-14 | 2014-03-14 | （ｒ）−３−ヒドロキシブチル（ｒ）−３−ヒドロキシブチレートの製造方法 |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US11566268B2 (ja) |
| EP (1) | EP2984066B1 (ja) |
| JP (1) | JP6110959B2 (ja) |
| KR (1) | KR102265842B1 (ja) |
| CN (1) | CN105246870A (ja) |
| AU (1) | AU2014230120B2 (ja) |
| BR (1) | BR112015023334B1 (ja) |
| CA (1) | CA2905225C (ja) |
| DK (1) | DK2984066T3 (ja) |
| ES (1) | ES2623368T3 (ja) |
| GB (1) | GB2515603B (ja) |
| HK (1) | HK1205100A1 (ja) |
| SG (1) | SG11201507685UA (ja) |
| WO (1) | WO2014140308A1 (ja) |
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| TR201908522T4 (tr) | 2008-01-04 | 2019-07-22 | The Government Of The U S A As Represented By The Secretary Dept Of Health And Human Services | Kan lipidi düşürücü maddeler olarak keton gövdeleri ve keton gövde esterleri. |
| US8642654B2 (en) | 2009-04-16 | 2014-02-04 | Isis Innovation Limited | Hydroxybutyrate ester and medical use thereof |
| JP5773870B2 (ja) * | 2008-08-21 | 2015-09-02 | アイシス イノヴェイション リミテッド | ヒドロキシ酪酸エステル及びその医学的使用 |
| AU2009344282B2 (en) | 2009-04-16 | 2014-12-11 | Government Of The United States Of America, As Represented By The Secretary, Department Of Health & Human Services | Process for the preparation of (3R)-hydroxybutyl (3R)-hydroxybutyrate by enzymatic enantioselective reduction employing Lactobacillus brevis alcohol dehydrogenase |
| GB201002983D0 (en) | 2010-02-22 | 2010-04-07 | Tdeltas Ltd | Nutritinal composition |
| FR2958154B1 (fr) | 2010-04-01 | 2012-06-08 | Oreal | Procede de soin et/ou de maquillage des rides |
| WO2012112951A1 (en) | 2011-02-17 | 2012-08-23 | Chd Bioscience, Inc. | COMPOSITIONS COMPRISING PEROXY α-KETOCARBOXYLIC ACID AND METHODS FOR PRODUCING AND USING THE SAME |
| WO2012113415A1 (en) | 2011-02-24 | 2012-08-30 | N.V. Nutricia | Ketogenic diet composition for the treatment of chemo therapy and/or radiation therapy patients |
| GB201206192D0 (en) | 2012-04-05 | 2012-05-23 | Tdeltas Ltd | Ketone bodies and ketone body esters and for maintaining or improving muscle power output |
| WO2014017046A1 (ja) | 2012-07-23 | 2014-01-30 | 国立大学法人東京大学 | 放射線障害の予防及び／又は治療剤 |
| CA2922223C (en) | 2012-11-05 | 2021-11-09 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services And Human Services | Ketone bodies to protect tissues from damage by ionizing radiation |
| GB201304467D0 (en) | 2013-03-12 | 2013-04-24 | Tdeltas Ltd | Compound for use in protecting skin |
| JP6110959B2 (ja) | 2013-03-14 | 2017-04-05 | オックスフォード ユニヴァーシティ イノヴェーション リミテッド | （ｒ）−３−ヒドロキシブチル（ｒ）−３−ヒドロキシブチレートの製造方法 |
| MY180761A (en) | 2013-03-19 | 2020-12-08 | Univ South Florida | Compositions and methods for producing elevated and sustained ketosis |
| GB201314127D0 (en) | 2013-08-07 | 2013-09-18 | Tdeltas Ltd | Ketone body and ketone body ester for reducing muscle breakdown |
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2014
- 2014-03-14 JP JP2015562212A patent/JP6110959B2/ja active Active
- 2014-03-14 AU AU2014230120A patent/AU2014230120B2/en active Active
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- 2014-03-14 WO PCT/EP2014/055156 patent/WO2014140308A1/en active Application Filing
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- 2014-03-14 CN CN201480022083.2A patent/CN105246870A/zh active Pending
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