CA2875063C - Method of synthesising sulforaphane - Google Patents
Method of synthesising sulforaphane Download PDFInfo
- Publication number
- CA2875063C CA2875063C CA2875063A CA2875063A CA2875063C CA 2875063 C CA2875063 C CA 2875063C CA 2875063 A CA2875063 A CA 2875063A CA 2875063 A CA2875063 A CA 2875063A CA 2875063 C CA2875063 C CA 2875063C
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- CA
- Canada
- Prior art keywords
- cyclodextrin
- sulforaphane
- process according
- complex
- catalyst
- 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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- SUVMJBTUFCVSAD-UHFFFAOYSA-N sulforaphane Chemical compound CS(=O)CCCCN=C=S SUVMJBTUFCVSAD-UHFFFAOYSA-N 0.000 title claims abstract description 149
- 238000000034 method Methods 0.000 title claims abstract description 100
- SUVMJBTUFCVSAD-JTQLQIEISA-N 4-Methylsulfinylbutyl isothiocyanate Natural products C[S@](=O)CCCCN=C=S SUVMJBTUFCVSAD-JTQLQIEISA-N 0.000 title claims abstract description 75
- 229960005559 sulforaphane Drugs 0.000 title claims abstract description 75
- 235000015487 sulforaphane Nutrition 0.000 title claims abstract description 75
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 80
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims abstract description 47
- 239000003054 catalyst Substances 0.000 claims abstract description 32
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- 238000002156 mixing Methods 0.000 claims abstract description 14
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/26—Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/724—Cyclodextrins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/02—Preparation of sulfones; Preparation of sulfoxides by formation of sulfone or sulfoxide groups by oxidation of sulfides, or by formation of sulfone groups by oxidation of sulfoxides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/18—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms
- C07C331/20—Isothiocyanates having isothiocyanate groups bound to acyclic carbon atoms of a saturated carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
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Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
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- Epidemiology (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Nanotechnology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Materials Engineering (AREA)
- Biochemistry (AREA)
- Medical Informatics (AREA)
- General Engineering & Computer Science (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Medicinal Preparation (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Catalysts (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261654277P | 2012-06-01 | 2012-06-01 | |
| US61/654,277 | 2012-06-01 | ||
| PCT/GB2013/051458 WO2013179057A1 (en) | 2012-06-01 | 2013-05-31 | Method of synthesising sulforaphane |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2875063A1 CA2875063A1 (en) | 2013-12-05 |
| CA2875063C true CA2875063C (en) | 2021-01-12 |
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| CN105001135B (zh) * | 2015-07-10 | 2017-04-12 | 北京化工大学 | 一种莱菔子素的化学合成方法 |
| CN108503568A (zh) * | 2017-02-27 | 2018-09-07 | 无锡杰西医药股份有限公司 | 一种适用于工业化生产的高纯度异硫氰酸酯类化合物制备方法 |
| CN107468666B (zh) * | 2017-08-18 | 2021-01-01 | 赣州华汉生物科技有限公司 | 一种可稳定保存的萝卜硫素胶囊及其制备方法 |
| KR20250051163A (ko) | 2017-09-28 | 2025-04-16 | 커먼웰쓰 사이언티픽 앤드 인더스트리얼 리서치 오가니제이션 | 이소티오시아네이트 함유 브라시카케아이 프로덕트 및 이의 제조 방법 |
| KR102889869B1 (ko) | 2018-09-24 | 2025-11-25 | 셰브론 필립스 케미컬 컴퍼니 엘피 | 증가된 중합 활성을 갖는 지지된 크롬 촉매를 제조하는 방법 |
| GB202005238D0 (en) | 2020-04-08 | 2020-05-20 | Evgen Pharma Plc | Crystalline complexes |
| WO2022140409A1 (en) | 2020-12-23 | 2022-06-30 | Church & Dwight Co., Inc. | Compositions and methods to increase production of isothiocyanates |
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| FR2776666B1 (fr) | 1998-03-31 | 2002-09-06 | Commissariat Energie Atomique | Complexes d'inclusion dans des cyclodextrines d'isothiocyanates organiques, en particulier bacteriostatiques, bactericides et/ou fongicides ou de leurs precurseurs naturels, et leur preparation |
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| CN100522154C (zh) | 2000-08-21 | 2009-08-05 | 杰德W·费伊 | 异硫氰酸酯类化合物在制备治疗螺杆菌感染的药物中的用途 |
| JP2002187842A (ja) | 2000-12-19 | 2002-07-05 | Toyo Shinyaku:Kk | ケール加工品およびその加工方法 |
| JP2003146803A (ja) | 2001-11-13 | 2003-05-21 | Carex Inc | 抗菌性粉末組成物およびその製造方法 |
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| FR2888235B1 (fr) | 2005-07-07 | 2007-09-14 | Nutrinov Sa | Procede d'extraction de sulforaphane a partir de broyat de crucifere contenant de la glucoraphanine |
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| PT3354267T (pt) * | 2007-01-23 | 2019-09-10 | Pharmagra Labs Inc | Sulforafano estabilizado |
| CN102249968B (zh) * | 2011-06-17 | 2013-07-17 | 常州大学 | 萝卜硫素的合成方法 |
| CN102423492A (zh) | 2011-12-31 | 2012-04-25 | 肖广惠 | 一种莱菔硫烷的包合物及其制备方法 |
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| CA2875063A1 (en) | 2013-12-05 |
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