IE780285L - PROCESS FOR THE PREPARATION OF d,l -5-METHYLTETRAHYDROFOLIC¹ACID - Google Patents
PROCESS FOR THE PREPARATION OF d,l -5-METHYLTETRAHYDROFOLIC¹ACIDInfo
- Publication number
- IE780285L IE780285L IE780285A IE28578A IE780285L IE 780285 L IE780285 L IE 780285L IE 780285 A IE780285 A IE 780285A IE 28578 A IE28578 A IE 28578A IE 780285 L IE780285 L IE 780285L
- Authority
- IE
- Ireland
- Prior art keywords
- preparation
- formula
- acid
- folic acid
- action
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D475/00—Heterocyclic compounds containing pteridine ring systems
- C07D475/02—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4
- C07D475/04—Heterocyclic compounds containing pteridine ring systems with an oxygen atom directly attached in position 4 with a nitrogen atom directly attached in position 2
-
- 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
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/20—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing sulfur, e.g. dimethyl sulfoxide [DMSO], docusate, sodium lauryl sulfate or aminosulfonic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Dermatology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
Abstract
Process for the preparation of d,l-5-methyltetrahydrofolic acid and its salts of the formula 1 in which X is hydrogen, an alkali metal or the equivalent of an alkaline earth metal, by reduction of folic acid with NaBH4 and methylation of the tetrahydrofolic acid obtained with aqueous solutions of formaldehyde and sodium borohydride in an inert gas atmosphere. The process is simple and can be carried out without separation of intermediates while carrying out the process steps successively in the same reaction vessel. The final products are obtained in a yield of more than 80%, relative to folic acid employed, in a purity of more than 99%. The compounds of the formula I obtained are non-toxic, stable at physiological pH and suitable for the preparation of liquid or solid pharmaceutical compositions for any type of application in human therapy. Such compositions exhibit haematopoietic action, hepatoprotective and antineoplastic action. <IMAGE>
[GB1572137A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB7290/77A GB1572137A (en) | 1977-02-22 | 1977-02-22 | Stable compositions for therapeutic use based on d,1-5-methyltetrahydrofolic acid and its salts |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE780285L true IE780285L (en) | 1978-08-22 |
| IE46402B1 IE46402B1 (en) | 1983-06-01 |
Family
ID=9830275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE285/78A IE46402B1 (en) | 1977-02-22 | 1978-02-09 | Process for the preparation of d, 1-5-methyltetra-hydrofolic acid |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS5831353B2 (en) |
| AR (1) | AR215162A1 (en) |
| AT (1) | AT380020B (en) |
| AU (1) | AU520715B2 (en) |
| BE (1) | BE863808A (en) |
| CA (1) | CA1093554A (en) |
| CH (1) | CH635344A5 (en) |
| CZ (1) | CZ279815B6 (en) |
| DD (1) | DD134099A5 (en) |
| DE (1) | DE2807393A1 (en) |
| DK (1) | DK144944C (en) |
| EG (1) | EG13399A (en) |
| ES (1) | ES467153A1 (en) |
| FI (1) | FI67082C (en) |
| FR (2) | FR2381047A1 (en) |
| GB (1) | GB1572137A (en) |
| GR (1) | GR71704B (en) |
| HU (1) | HU179422B (en) |
| IE (1) | IE46402B1 (en) |
| IL (1) | IL54052A (en) |
| IN (1) | IN149574B (en) |
| LU (1) | LU79067A1 (en) |
| MX (1) | MX5288E (en) |
| NL (1) | NL190285C (en) |
| NO (1) | NO147793C (en) |
| NZ (1) | NZ186465A (en) |
| PL (1) | PL118654B1 (en) |
| PT (1) | PT67656B (en) |
| SE (1) | SE437028B (en) |
| SU (1) | SU747427A3 (en) |
| YU (1) | YU40505B (en) |
| ZA (1) | ZA78837B (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5838285A (en) * | 1981-08-25 | 1983-03-05 | Kanegafuchi Chem Ind Co Ltd | Preparation of 5-methyl-(6rs)-5,6,7,8-tetrahydro-l-folic acid magnesium salt or its free acid |
| GB8621268D0 (en) * | 1986-09-03 | 1986-10-08 | Univ Strathclyde | Separation of substances |
| IT1229517B (en) * | 1989-01-31 | 1991-09-03 | Bioresearch Spa | USE OF 5-METHYLTETRAHYDROPHOLIC ACID, OF 5 FORMYLTHETRAHYDROPHOLIC ACID, AND OF THEIR PHARMACEUTICALLY ACCEPTABLE SALTS FOR THE PREPARATION OF PHARMACEUTICAL COMPOSITIONS IN THE FORM OF CONTROLLED RELEASE SUITABLE FOR BEING EMPLOYED IN THE TREATMENT OF DISORDERS IN THE TREATMENT OF DISORDERS. |
| IT1229203B (en) * | 1989-03-22 | 1991-07-25 | Bioresearch Spa | USE OF 5 METHYLTHETRAHYDROPHOLIC ACID, 5 FORMYLTHETRAHYDROPHOLIC ACID AND THEIR PHARMACEUTICALLY ACCEPTABLE SALTS FOR THE PREPARATION OF PHARMACEUTICAL COMPOSITIONS IN THE FORM OF CONTROLLED RELEASE ACTIVE IN THE THERAPY OF MENTAL AND ORGANIC DISORDERS. |
| NL8901432A (en) * | 1989-06-06 | 1991-01-02 | Pharmachemie Bv | STABLE AQUEOUS FOLINATE SOLUTION AT REFRIGERATOR TEMPERATURE, AND METHOD FOR PREPARING THAT. |
| CH680731A5 (en) * | 1990-04-12 | 1992-10-30 | Sapec Fine Chemicals | |
| US5217974A (en) * | 1991-03-29 | 1993-06-08 | Eli Lilly And Company | Method for treating gar-transformylase tumors in mammals and reducing mammalian toxicity |
| CH683261A5 (en) * | 1991-10-10 | 1994-02-15 | Applied Pharma Res | A process for the preparation of Methyltetrahydrofolic in the form (6 (R, S) (-)) N-5 and separation of the active diastereoisomer (6 (S) (-)) N-5) in the form of salts. |
| CH682665A5 (en) * | 1991-10-29 | 1993-10-29 | Sapec Fine Chemicals | Process for the purification of crude alkaline earth metal salts from N (5) -methyl-5,6,7,8-tetrahydrofolic acid. |
| US6162914A (en) * | 1998-04-24 | 2000-12-19 | Cerbios-Pharma S.A. | Process for the reduction of pterins |
| CH693905A5 (en) * | 1999-04-15 | 2004-04-15 | Eprova Ag | Stable crystalline salts of 5-methyl tetrahydrofolic acid. |
| CH698729B1 (en) * | 2007-05-30 | 2009-10-15 | Cerbios Pharma Sa | Stable crystalline (6S) -N (5) -methyl-5, 6,7,8-tetrahydrofolic acid. |
| CN103214487A (en) * | 2013-04-12 | 2013-07-24 | 张家港威胜生物医药有限公司 | Synthesis of important medical chemical raw material (6S)-5-methyl tetrahydrofolate |
| WO2015193778A1 (en) | 2014-06-16 | 2015-12-23 | Mylan Laboratories Ltd. | Crystalline form of levomefolate calcium |
| PT3844145T (en) | 2018-08-28 | 2026-04-28 | Pmc Organometallix Inc | Low free 2-mercaptoethanol ester and uses thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL80276C (en) * | ||||
| GB1293541A (en) * | 1969-03-18 | 1972-10-18 | John Alexander Blair | Folic acid derivatives |
| US3856959A (en) * | 1972-07-24 | 1974-12-24 | Department Of Health Education | Inhibition of leukemia utilizing 5-methyltetrahydrohomofolate |
| US4148999A (en) * | 1977-08-22 | 1979-04-10 | The Government Of The United States Of America | Preparation and purification of citrovorum factor |
| CH649550A5 (en) * | 1984-02-09 | 1985-05-31 | Eprova Ag | Process for the preparation of alkaline earth metal salts of 5-methyltetrahydrofolic acid |
-
1977
- 1977-02-22 GB GB7290/77A patent/GB1572137A/en not_active Expired
-
1978
- 1978-02-09 BE BE185038A patent/BE863808A/en not_active IP Right Cessation
- 1978-02-09 CA CA296,754A patent/CA1093554A/en not_active Expired
- 1978-02-09 IE IE285/78A patent/IE46402B1/en not_active IP Right Cessation
- 1978-02-09 AT AT0090378A patent/AT380020B/en not_active IP Right Cessation
- 1978-02-13 NZ NZ186465A patent/NZ186465A/en unknown
- 1978-02-13 ZA ZA00780837A patent/ZA78837B/en unknown
- 1978-02-15 PT PT67656A patent/PT67656B/en unknown
- 1978-02-15 LU LU79067A patent/LU79067A1/en unknown
- 1978-02-15 IL IL54052A patent/IL54052A/en unknown
- 1978-02-15 IN IN174/CAL/78A patent/IN149574B/en unknown
- 1978-02-16 NL NLAANVRAGE7801775,A patent/NL190285C/en not_active IP Right Cessation
- 1978-02-18 PL PL1978204747A patent/PL118654B1/en unknown
- 1978-02-20 GR GR55500A patent/GR71704B/el unknown
- 1978-02-20 AU AU33430/78A patent/AU520715B2/en not_active Expired
- 1978-02-20 YU YU379/78A patent/YU40505B/en unknown
- 1978-02-20 DD DD78203761A patent/DD134099A5/en unknown
- 1978-02-21 MX MX786871U patent/MX5288E/en unknown
- 1978-02-21 SU SU782588551A patent/SU747427A3/en active
- 1978-02-21 SE SE7801973A patent/SE437028B/en not_active IP Right Cessation
- 1978-02-21 NO NO780594A patent/NO147793C/en unknown
- 1978-02-21 DE DE19782807393 patent/DE2807393A1/en active Granted
- 1978-02-21 DK DK76578A patent/DK144944C/en not_active IP Right Cessation
- 1978-02-21 FR FR7804847A patent/FR2381047A1/en active Granted
- 1978-02-21 EG EG103/78A patent/EG13399A/en active
- 1978-02-21 FI FI780565A patent/FI67082C/en not_active IP Right Cessation
- 1978-02-21 ES ES467153A patent/ES467153A1/en not_active Expired
- 1978-02-22 AR AR271183A patent/AR215162A1/en active
- 1978-02-22 HU HU78BI562A patent/HU179422B/en unknown
- 1978-02-22 JP JP53018637A patent/JPS5831353B2/en not_active Expired
- 1978-02-22 CH CH193678A patent/CH635344A5/en not_active IP Right Cessation
- 1978-02-22 CZ CS781129A patent/CZ279815B6/en unknown
- 1978-07-13 FR FR7820936A patent/FR2385397A1/en active Granted
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |