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Production of salts of 4-hydroxybutyrate using biobased raw materials

a technology of gamma hydroxybutyrate and raw materials, applied in the field of gamma hydroxybutyrate, can solve the problems of affecting the effect of gamma hydroxybutyrate, and causing nausea, dizziness, drowsiness, etc., and achieves the effects of alcohol consumption, reducing the risk of ghb

Inactive Publication Date: 2016-03-10
CJ CHEILJEDANG CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text discusses the use of gamma-hydroxybutyrate and its derivatives as pharmaceutical substances. These substances can be used alone or in combination with other drugs to improve their metabolism or enhance their binding affinity to target receptors. The text also mentions the possibility of modifying these substances by adding deuterium or fluorine atoms to create new compounds with improved properties.

Problems solved by technology

However, GHB is most well known for it abuse potential.
At higher doses, GHB may induce nausea, dizziness, drowsiness, agitation, visual disturbances, depressed breathing, amnesia, unconsciousness, and death.
Consuming GHB with alcohol is dangerous as it can lead to vomiting in combination with unrouseable sleep, a potentially lethal combination.
It is difficult to establish how often GHB is used to facilitate rape as it is difficult to detect in a urine sample after a day, and many victims may not recall the rape until some time after this, although GHB can be detected in hair.

Method used

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  • Production of salts of 4-hydroxybutyrate using biobased raw materials
  • Production of salts of 4-hydroxybutyrate using biobased raw materials

Examples

Experimental program
Comparison scheme
Effect test

example 1

Production of Biobased Gamma-Butyrolactone (GBL) from the Pyrolysis of a Genetically Engineered Microbe Producing poly-4-hydroxybutyrate (P4HB)

[0175]In this example biobased GBL is produced for the conversion to Biobased GHB for use in pharmaceutical applications with improved monitoring and safety. Biomass containing poly-4-hydroxybutyrate (poly-4HB) was produced in a 20 L New Brunswick Scientific fermentor (BioFlo 4500) using a genetically modified E. coli strain specifically designed for high yield production of poly-4HB from glucose syrup as the sole carbon feed source. The use of a renewable resource based feedstock such as glucose syrup as the sole carbon source enables the production of a biobased P4HB and hence the production of biobased GBL and derivatives including biobased gamma-hydroxybutyric acid (GHB). Examples of the E. coli strains, fermentation conditions, media and feed conditions are described in U.S. Pat. Nos. 6,316,262; 6,689,589; 7,081,357; and 7,229,804. The E...

example 2

Post Purification of Biobased GBL by Distillation, Steam Stripping and Peroxide Treatment

[0180]This example outlines a procedure for the purification of biobased GBL liquid prepared from pyrolysis of a genetically engineered microbe producing poly-4-hydroxybutyrate polymer mixed with a catalyst as outlined previously in Example 1.

[0181]The GBL purification is a batch process whereby the “crude” GBL liquid recovered after pyrolysis is first filtered to remove any solid particulates (typically <1% of the total crude GBL weight) and then distilled twice to remove compounds contributing to odor and color.

[0182]Filtration of the crude GBL liquid was carried out on a lab scale using a Buchner fritted-glass funnel coupled to an Erlenmeyer receiving flask. Approximately 1 liter of crude GBL was filtered which resulted in approximately 0.99 liters of recovered GBL liquid.

[0183]The distillation of the filtered GBL liquid was carried out using a high vacuum 20 stage glass distillation column. ...

example 3

Production of Biobased-GBL from Purified P4HB Coupled with Thermolysis

[0188]In this example biomass containing P4HB is produced in a fermentation process using glucose as the sole carbon feed source as described above. Following the fermentation, the P4HB is extracted from the biomass and purified. Suitable methods for purifying P4HB from biomass are described in for example U.S. Pat. No. 6,610,764 to Tepha and Metabolix and U.S. Pat. Nos. 7,981,642 and 7,576,173 to Metabolix Inc. Purified P4HB is subjected to a thermolysis procedure essentially under the same conditions as in Example 1 and GBL is produced. GBL produced using this approach should have a biobased content of around 99% when tested according to the standard ASTM-D6866-11 testing protocol.

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Abstract

Gamma-butyrolactone (“GBL”) and Gamma-hydroxybutyrate (“GHB”) having a unique carbon footprint as defined by the percent modern carbon (pmc) are described herein. The percent modern carbon can be controlled by varying the amounts of biobased, renewable starting materials and petroleum-based starting materials to prepare GBL or GHB having a defined pmc or by preparing mixtures of GBL or GHB prepared from biobased renewable starting materials and GBL or GHB prepared from petroleum-based starting materials.

Description

FIELD OF THE INVENTION[0001]This invention is in the field of gamma-hydroxybutyrate having a carbon footprint which can be used to identify the source of the gamma-hydroxybutyrate, pharmaceutical compositions containing the traceable gamma-hydroxybutyrate, and methods of use thereof.BACKGROUND OF THE INVENTION[0002]γ-Hydroxybutyric acid (OHB), also known as 4-hydroxybutanoic acid and sodium oxybate (INN), is a naturally occurring substance found in the human central nervous system, as well as in wine, beef, small citrus fruits, and almost all animals in small amounts. GHB is naturally produced in the human body's cells and is structurally related to the ketone body beta-hydroxybutyrate.[0003]HB has been used in medical settings as a general anesthetic, to treat conditions such as insomnia, clinical depression, narcolepsy, and alcoholism. GHB as the sodium salt, known as sodium oxybate, is sold by Jazz Pharmaceuticals under the name Xyrem to treat cataplexy and excessive daytime slee...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07C59/01A61K9/28A61K47/34A61L17/10C07C51/41C08G63/06
CPCC07C59/01C08G63/06A61L17/105C07C51/41A61K47/34A61K9/28C07D307/06C07D307/33
Inventor PEOPLES, OLIVERSAMUELSON, DEREKSENECHAL, MAXPARK, SUNG MINGREDDER, JOSEPHMIRLEY, CHRISTOPHER
Owner CJ CHEILJEDANG CORP
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