GB1572137A - Stable compositions for therapeutic use based on d,1-5-methyltetrahydrofolic acid and its salts - Google Patents
Stable compositions for therapeutic use based on d,1-5-methyltetrahydrofolic acid and its salts Download PDFInfo
- Publication number
- GB1572137A GB1572137A GB7290/77A GB729077A GB1572137A GB 1572137 A GB1572137 A GB 1572137A GB 7290/77 A GB7290/77 A GB 7290/77A GB 729077 A GB729077 A GB 729077A GB 1572137 A GB1572137 A GB 1572137A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lyophilisation
- methyltetrahydrofolate
- stabiliser
- signifies
- acid
- 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.)
- Expired
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 11
- 150000003839 salts Chemical class 0.000 title claims abstract description 6
- 229940105150 5-methyltetrahydrofolic acid Drugs 0.000 title claims description 11
- 230000001225 therapeutic effect Effects 0.000 title claims description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 230000000118 anti-neoplastic effect Effects 0.000 claims abstract description 3
- ZNOVTXRBGFNYRX-ABLWVSNPSA-N levomefolic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-ABLWVSNPSA-N 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 9
- 238000004108 freeze drying Methods 0.000 claims description 8
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Natural products OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- -1 5-methyltetrahydrofolic acid - sodium 5-methyltetrahydrofolate - calcium 5-methyltetrahydrofolate - magnesium 5-methyltetrahydrofolate Chemical compound 0.000 claims description 5
- 108010024636 Glutathione Proteins 0.000 claims description 5
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims description 5
- 235000018417 cysteine Nutrition 0.000 claims description 5
- 229960003180 glutathione Drugs 0.000 claims description 5
- 229960003151 mercaptamine Drugs 0.000 claims description 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 claims description 3
- ZNXZGRMVNNHPCA-VIFPVBQESA-N pantetheine Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCS ZNXZGRMVNNHPCA-VIFPVBQESA-N 0.000 claims description 3
- QBWKPGNFQQJGFY-QLFBSQMISA-N 3-[(1r)-1-[(2r,6s)-2,6-dimethylmorpholin-4-yl]ethyl]-n-[6-methyl-3-(1h-pyrazol-4-yl)imidazo[1,2-a]pyrazin-8-yl]-1,2-thiazol-5-amine Chemical compound N1([C@H](C)C2=NSC(NC=3C4=NC=C(N4C=C(C)N=3)C3=CNN=C3)=C2)C[C@H](C)O[C@H](C)C1 QBWKPGNFQQJGFY-QLFBSQMISA-N 0.000 claims description 2
- 239000004471 Glycine Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 229940125846 compound 25 Drugs 0.000 claims description 2
- 238000007906 compression Methods 0.000 claims description 2
- 230000006835 compression Effects 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims description 2
- 210000004185 liver Anatomy 0.000 claims description 2
- 230000014759 maintenance of location Effects 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 5
- 235000019152 folic acid Nutrition 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 3
- 238000002360 preparation method Methods 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 239000007788 liquid Substances 0.000 abstract description 2
- 231100000252 nontoxic Toxicity 0.000 abstract description 2
- 230000003000 nontoxic effect Effects 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract description 2
- OVBPIULPVIDEAO-LBPRGKRZSA-N folic acid Chemical compound C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-LBPRGKRZSA-N 0.000 abstract 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- OVBPIULPVIDEAO-UHFFFAOYSA-N N-Pteroyl-L-glutaminsaeure Natural products C=1N=C2NC(N)=NC(=O)C2=NC=1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 OVBPIULPVIDEAO-UHFFFAOYSA-N 0.000 abstract 2
- 229960000304 folic acid Drugs 0.000 abstract 2
- 239000011724 folic acid Substances 0.000 abstract 2
- 229910000033 sodium borohydride Inorganic materials 0.000 abstract 2
- 239000012279 sodium borohydride Substances 0.000 abstract 2
- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 abstract 1
- MSTNYGQPCMXVAQ-KIYNQFGBSA-N 5,6,7,8-tetrahydrofolic acid Chemical compound N1C=2C(=O)NC(N)=NC=2NCC1CNC1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 MSTNYGQPCMXVAQ-KIYNQFGBSA-N 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 230000003394 haemopoietic effect Effects 0.000 abstract 1
- 230000002443 hepatoprotective effect Effects 0.000 abstract 1
- 239000011261 inert gas Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 230000011987 methylation Effects 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 238000000926 separation method Methods 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- 235000010323 ascorbic acid Nutrition 0.000 description 2
- 239000011668 ascorbic acid Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 2
- FLJWVVUJGVNXMZ-UHFFFAOYSA-N 2-sulfanylacetaldehyde Chemical compound SCC=O FLJWVVUJGVNXMZ-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NCEXYHBECQHGNR-UHFFFAOYSA-N chembl421 Chemical compound C1=C(O)C(C(=O)O)=CC(N=NC=2C=CC(=CC=2)S(=O)(=O)NC=2N=CC=CC=2)=C1 NCEXYHBECQHGNR-UHFFFAOYSA-N 0.000 description 1
- 150000002224 folic acids Chemical class 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Priority Applications (34)
| 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 |
| IE285/78A IE46402B1 (en) | 1977-02-22 | 1978-02-09 | Process for the preparation of d, 1-5-methyltetra-hydrofolic acid |
| AT0090378A AT380020B (de) | 1977-02-22 | 1978-02-09 | Verfahren zur herstellung von d,1-5-methyltetrahydrofols|ureund deren salzen |
| BE185038A BE863808A (fr) | 1977-02-22 | 1978-02-09 | Procede de production de l'acide 5-methyltetrahydrofoliquded |
| CA296,754A CA1093554A (en) | 1977-02-22 | 1978-02-09 | Process for producing d,1-5-methyltetrahy-drofolic acid and its salts |
| NZ186465A NZ186465A (en) | 1977-02-22 | 1978-02-13 | A process for producing dl-5-methyltetrahydrofolic acid or its salts and stable pharmaceutical compositions |
| ZA00780837A ZA78837B (en) | 1977-02-22 | 1978-02-13 | Process for producing d,1-5-methyltetrahydrofolic acid and its salts |
| IL54052A IL54052A (en) | 1977-02-22 | 1978-02-15 | Production of d,1-5-methyltetra-hydrofolic acid and its salts and stabilized therapeutic compositions containing salts thereof |
| PT67656A PT67656B (en) | 1977-02-22 | 1978-02-15 | Process for producing d,1-5-methyltetrahydrofolic acid andits salts |
| LU79067A LU79067A1 (fr) | 1977-02-22 | 1978-02-15 | Procede de production de l'acide 5-methyltetrahydrofolique-d,1 et de ses sels |
| IN174/CAL/78A IN149574B (enrdf_load_stackoverflow) | 1977-02-22 | 1978-02-15 | |
| NLAANVRAGE7801775,A NL190285C (nl) | 1977-02-22 | 1978-02-16 | Werkwijze voor het bereiden van d,1-5-methyltetrahydrofoliumzuur; farmaceutisch preparaat. |
| PL1978204747A PL118654B1 (en) | 1977-02-22 | 1978-02-18 | Process for preparing d.,l-5-methyltetrahydrofolic acid and its saltsy i ee solejj |
| DD78203761A DD134099A5 (de) | 1977-02-22 | 1978-02-20 | Verfahren zur herstellung von d,1-5-methyltetrahydrofolsaeure und deren salzen |
| AU33430/78A AU520715B2 (en) | 1977-02-22 | 1978-02-20 | PROCESS FOR PRODUCING (d. 1)-5-METHYL-TETRAHYDROFOLIC ACID |
| YU379/78A YU40505B (en) | 1977-02-22 | 1978-02-20 | Process for producing d,1-5methyl-tetrahydro-folic acid and salts thereof |
| GR55500A GR71704B (enrdf_load_stackoverflow) | 1977-02-22 | 1978-02-20 | |
| EG103/78A EG13399A (en) | 1977-02-22 | 1978-02-21 | Process for producing d,i-5-methyl tetrahydrofolic acid and its salts |
| DK76578A DK144944C (da) | 1977-02-22 | 1978-02-21 | Fremgangsmaade til fremstilling af d,1-5-methyltetrahydrofolinsyre eller salte deraf |
| ES467153A ES467153A1 (es) | 1977-02-22 | 1978-02-21 | Procedimiento para la preparacion de acido d, 1-5-metilte- trahidrofolico y sus sales. |
| DE19782807393 DE2807393A1 (de) | 1977-02-22 | 1978-02-21 | Verfahren zur herstellung von d,1-5-methyltetrahydrofolsaeure und deren salzen |
| SE7801973A SE437028B (sv) | 1977-02-22 | 1978-02-21 | Forfarande for framstellning av d,l-5-metyltetrahydro-folsyra |
| MX786871U MX5288E (es) | 1977-02-22 | 1978-02-21 | Procedimiento mejorado para la preparacion de 5-metiltetrahidrofolato de metales alcalinos o alcalinoterreos |
| NO780594A NO147793C (no) | 1977-02-22 | 1978-02-21 | Fremgangsmaate ved fremstilling av d,1-5-methyl-tetrahydrofolinsyre og dens salter. |
| SU782588551A SU747427A3 (ru) | 1977-02-22 | 1978-02-21 | Способ получени -5-метилтетрагидрофолиевой кислоты или ее солей |
| FR7804847A FR2381047A1 (fr) | 1977-02-22 | 1978-02-21 | Procede de production de l'acide 5-methyltetrahydrofolique- d,1 et de ses sels |
| FI780565A FI67082C (fi) | 1977-02-22 | 1978-02-21 | Foerfarande foer framstaellning av d,1-5-metyltetrahydrofolsyra och salter daerav |
| CH193678A CH635344A5 (en) | 1977-02-22 | 1978-02-22 | Process for the preparation of d,l-5-methyltetrahydrofolic acid and its salts |
| HU78BI562A HU179422B (en) | 1977-02-22 | 1978-02-22 | Process for preparing dl-5-methyl-tetrahydrofolic acid and salts thereof |
| AR271183A AR215162A1 (es) | 1977-02-22 | 1978-02-22 | Procedimiento mejorado para la preparacion de acido d,1-5-metiltetrahidrofolico y sus sales |
| CS781129A CZ279815B6 (cs) | 1977-02-22 | 1978-02-22 | Způsob výroby kyseliny d,1-5-methyltetrahydrolistové nebo jejích z farmaceutického hlediska přijatelných solí |
| JP53018637A JPS5831353B2 (ja) | 1977-02-22 | 1978-02-22 | ｄ，ｌ↓−５↓−メチルテトラヒドロ葉酸及びその塩の製造方法 |
| FR7820936A FR2385397A1 (fr) | 1977-02-22 | 1978-07-13 | Compositions stables d'un sel alcalin ou alcalino-terreux d'acide 5-methyltetrahydrofolique a usage therapeutique |
| US07/814,571 US5223500A (en) | 1977-02-22 | 1991-12-30 | Stable pharmaceutical composition of alkaline or alkaline earth 5-methyl tetrahydrofolate |
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 (1)
| Publication Number | Publication Date |
|---|---|
| GB1572137A true GB1572137A (en) | 1980-07-23 |
Family
ID=9830275
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7290/77A Expired GB1572137A (en) | 1977-02-22 | 1977-02-22 | Stable compositions for therapeutic use based on d,1-5-methyltetrahydrofolic acid and its salts |
Country Status (32)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0382019A1 (en) * | 1989-01-31 | 1990-08-16 | BIORESEARCH S.p.A. | Use of 5-methyltetrahydrofolic acid, of 5-formyl-tetrahydrofolic acid and of their pharmaceutically acceptable salts for the preparation of controlled release pharmaceutical compositions suitable for the use in the therapy of depressive disturbances, and pharmaceutical compositions thus prepared |
| EP0388827A1 (en) * | 1989-03-22 | 1990-09-26 | BIORESEARCH S.p.A. | Use of 5-methyltetrahydrofolic acid, 5-formyltetrahydrofolic acid and their pharmaceutically acceptable salts in the preparation of pharmaceutical compositions in controlled release form active in the therapy of organic mental disturbances, and the relative pharmaceutical compositions |
| US5382581A (en) * | 1990-04-12 | 1995-01-17 | Sapec S.A. Fine Chemicals | (6R)- and (6S)-diastereoisomers of an ammonium salts of N5 -methyl-5,6,7,8-tetrahydrofolic acid |
| WO2015193778A1 (en) | 2014-06-16 | 2015-12-23 | Mylan Laboratories Ltd. | Crystalline form of levomefolate calcium |
| US12012500B2 (en) | 2018-08-28 | 2024-06-18 | Pmc Organometallix, Inc. | Low free 2-mercaptoethanol ester and uses thereof |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5838285A (ja) * | 1981-08-25 | 1983-03-05 | Kanegafuchi Chem Ind Co Ltd | ５−メチル−（６ｒｓ）−５，６，７，８−テトラヒドロ−ｌ−葉酸のマグネシウム塩またはその遊離酸の製法 |
| GB8621268D0 (en) * | 1986-09-03 | 1986-10-08 | Univ Strathclyde | Separation of substances |
| NL8901432A (nl) * | 1989-06-06 | 1991-01-02 | Pharmachemie Bv | Bij koelkasttemperatuur stabiele waterige folinaatoplossing, alsmede werkwijze ter bereiding daarvan. |
| 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 (it) * | 1991-10-10 | 1994-02-15 | Applied Pharma Res | Procedimento per la preparazione dell'acido metiltetraidrofolico nella forma (6(R,S)(-))N-5 e separazione del diastereoisomero attivo (6(S)(-))N-5) sotto forma di sali. |
| CH682665A5 (de) * | 1991-10-29 | 1993-10-29 | Sapec Fine Chemicals | Verfahren zur Reinigung von rohen Erdalkalimetallsalzen von N(5)-Methyl-5,6,7,8-tetrahydrofolsäure. |
| US6162914A (en) * | 1998-04-24 | 2000-12-19 | Cerbios-Pharma S.A. | Process for the reduction of pterins |
| CH693905A5 (de) * | 1999-04-15 | 2004-04-15 | Eprova Ag | Stabile kristalline Salze von 5-Methyltetrahydrofolsäure. |
| CH698729B1 (de) * | 2007-05-30 | 2009-10-15 | Cerbios Pharma Sa | Stabile, kristalline (6S)-N(5)-Methyl-5, 6,7,8-tetrahydrofolsäure. |
| CN103214487A (zh) * | 2013-04-12 | 2013-07-24 | 张家港威胜生物医药有限公司 | 一种重要医药化工原料(6s)-5-甲基四氢叶酸盐的合成 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL80276C (enrdf_load_stackoverflow) * | ||||
| 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/xx not_active IP Right Cessation
- 1978-02-09 AT AT0090378A patent/AT380020B/de 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
- 1978-02-13 NZ NZ186465A patent/NZ186465A/xx unknown
- 1978-02-13 ZA ZA00780837A patent/ZA78837B/xx unknown
- 1978-02-15 PT PT67656A patent/PT67656B/pt unknown
- 1978-02-15 LU LU79067A patent/LU79067A1/xx unknown
- 1978-02-15 IL IL54052A patent/IL54052A/xx unknown
- 1978-02-15 IN IN174/CAL/78A patent/IN149574B/en unknown
- 1978-02-16 NL NLAANVRAGE7801775,A patent/NL190285C/xx not_active IP Right Cessation
- 1978-02-18 PL PL1978204747A patent/PL118654B1/pl unknown
- 1978-02-20 GR GR55500A patent/GR71704B/el unknown
- 1978-02-20 DD DD78203761A patent/DD134099A5/xx unknown
- 1978-02-20 AU AU33430/78A patent/AU520715B2/en not_active Expired
- 1978-02-20 YU YU379/78A patent/YU40505B/xx unknown
- 1978-02-21 FI FI780565A patent/FI67082C/fi not_active IP Right Cessation
- 1978-02-21 FR FR7804847A patent/FR2381047A1/fr active Granted
- 1978-02-21 SU SU782588551A patent/SU747427A3/ru active
- 1978-02-21 MX MX786871U patent/MX5288E/es unknown
- 1978-02-21 DE DE19782807393 patent/DE2807393A1/de active Granted
- 1978-02-21 DK DK76578A patent/DK144944C/da not_active IP Right Cessation
- 1978-02-21 EG EG103/78A patent/EG13399A/xx active
- 1978-02-21 ES ES467153A patent/ES467153A1/es not_active Expired
- 1978-02-21 SE SE7801973A patent/SE437028B/sv not_active IP Right Cessation
- 1978-02-21 NO NO780594A patent/NO147793C/no unknown
- 1978-02-22 JP JP53018637A patent/JPS5831353B2/ja not_active Expired
- 1978-02-22 AR AR271183A patent/AR215162A1/es active
- 1978-02-22 CZ CS781129A patent/CZ279815B6/cs unknown
- 1978-02-22 HU HU78BI562A patent/HU179422B/hu unknown
- 1978-02-22 CH CH193678A patent/CH635344A5/de not_active IP Right Cessation
- 1978-07-13 FR FR7820936A patent/FR2385397A1/fr active Granted
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0382019A1 (en) * | 1989-01-31 | 1990-08-16 | BIORESEARCH S.p.A. | Use of 5-methyltetrahydrofolic acid, of 5-formyl-tetrahydrofolic acid and of their pharmaceutically acceptable salts for the preparation of controlled release pharmaceutical compositions suitable for the use in the therapy of depressive disturbances, and pharmaceutical compositions thus prepared |
| US5538734A (en) * | 1989-01-31 | 1996-07-23 | Bioresearch S.P.A. | 5-methyltetrahydrofolic acid, 5-formyl-tetrahydrofolic acid and their pharmaceutically acceptable salts for use in the therapy of depressive disturbances |
| EP0388827A1 (en) * | 1989-03-22 | 1990-09-26 | BIORESEARCH S.p.A. | Use of 5-methyltetrahydrofolic acid, 5-formyltetrahydrofolic acid and their pharmaceutically acceptable salts in the preparation of pharmaceutical compositions in controlled release form active in the therapy of organic mental disturbances, and the relative pharmaceutical compositions |
| US5059595A (en) * | 1989-03-22 | 1991-10-22 | Bioresearch, S.P.A. | Pharmaceutical compositions containing 5-methyltetrahydrofolic acid, 5-formyltetrahydrofolic acid and their pharmaceutically acceptable salts in controlled-release form active in the therapy of organic mental disturbances |
| US5382581A (en) * | 1990-04-12 | 1995-01-17 | Sapec S.A. Fine Chemicals | (6R)- and (6S)-diastereoisomers of an ammonium salts of N5 -methyl-5,6,7,8-tetrahydrofolic acid |
| WO2015193778A1 (en) | 2014-06-16 | 2015-12-23 | Mylan Laboratories Ltd. | Crystalline form of levomefolate calcium |
| US12012500B2 (en) | 2018-08-28 | 2024-06-18 | Pmc Organometallix, Inc. | Low free 2-mercaptoethanol ester and uses thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19970221 |