GB735112A - Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereof - Google Patents

Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereof

Info

Publication number
GB735112A
GB735112A GB10742/52A GB1074252A GB735112A GB 735112 A GB735112 A GB 735112A GB 10742/52 A GB10742/52 A GB 10742/52A GB 1074252 A GB1074252 A GB 1074252A GB 735112 A GB735112 A GB 735112A
Authority
GB
United Kingdom
Prior art keywords
acid
tetrahydro
aliphatic amino
formyl
amino 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
Application number
GB10742/52A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth Holdings LLC
Original Assignee
American Cyanamid Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Publication of GB735112A publication Critical patent/GB735112A/en
Expired legal-status Critical Current

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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D475/00—Heterocyclic compounds containing pteridine ring systems
    • C07D475/06—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4
    • C07D475/08—Heterocyclic compounds containing pteridine ring systems with a nitrogen atom directly attached in position 4 with a nitrogen atom directly attached in position 2

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises the calcium salts of 5,6,7,8-tetrahydro-N5-formyl pteroic acid and aliphatic amino acid amides thereof, and a process for the preparation thereof by reacting 5,6,7,8-tetrahydro-N5-formyl pteroic acid or an aliphatic amino acid amide thereof with an inorganic calcium compound in an aqueous medium, or by treating 5,6,7,8-tetrahydro-N10-formyl pteroic acid or 5,6,7,8-tetrahydro-N5, N10-diformyl pteroic acid or an aliphatic amino acid amide thereof with aqueous sodium hydroxide whereby a soluble sodium salt is formed in an alkaline solution, heating and subsequently acidifying the reaction mixture to form 5,6,7,8-tetrahydro - N5 - formyl pteroic acid or an aliphatic amino acid amide thereof, and then reacting the said acid or acid amide with an inorganic calcium compound in an aqueous medium at a pH within the range of 7 to 14, e.g. 10 to 13, to produce the required calcium salt. The heating to form the N5-formyl compound may be carried out at 80 DEG to 100 DEG C. The inorganic calcium compound may be calcium chloride in which case the resulting reaction mixture is diluted with a water-miscible organic solvent to precipitate the required calcium salt. The aliphatic amino acid amide group may be derived from glutamic or aspartic acid or glycine, leucine, alanine, isovaline or cysteine. In the example calcium 5,6,7,8 - tetrahydro - N5 - formylpteroylglutamate is prepared by the methods outlined above and also be adding calcium sulphate to barium 5,6,7,8 - tetrahydro - N5 - formylpteroylglutamic acid in an aqueous media. Specifications 733,062 and 733,130 are referred to. N5,N10 - Diformylpteroic acid and aliphatic amino acid amides thereof are prepared by reacting pteroic acid or an aliphatic amino acid amide thereof with 98 to 100 per cent formic acid-preferably in the presence of acetic anhydride. Barium 5,6,7,8 - tetrahydro - N5 - formylpteroylglutamic acid is prepared by reacting pteroylglutamic acid and formic acid to form N10 - formylpteroylglutamic acid, hydrogenating the product in the presence of platinum oxide to form p 5,6,7,8-tetrahydro-N10-formylpteroylglutamic acid which is then heated at an alkaline pH to form the corresponding N5-formyl compound and aqueous barium chloride is added to precipitate impurity, the required barium salt being precipitated by adding alcohol to the clear solution.
GB10742/52A 1951-05-05 1952-04-29 Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereof Expired GB735112A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US735112XA 1951-05-05 1951-05-05

Publications (1)

Publication Number Publication Date
GB735112A true GB735112A (en) 1955-08-17

Family

ID=22114119

Family Applications (1)

Application Number Title Priority Date Filing Date
GB10742/52A Expired GB735112A (en) 1951-05-05 1952-04-29 Improvements relating to the production of calcium salts of 5,6,7,8-tetrahydro-n-formyl pteroic acid and aliphatic amino acid amides thereof

Country Status (1)

Country Link
GB (1) GB735112A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927113A (en) * 1957-10-14 1960-03-01 Lepetit Spa Leucovorin purification
EP0548895A2 (en) * 1991-12-21 1993-06-30 Sapec S.A. Fine Chemicals Process for the preparation of pure diasteroisomers of tetrahydrofolates

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927113A (en) * 1957-10-14 1960-03-01 Lepetit Spa Leucovorin purification
EP0548895A2 (en) * 1991-12-21 1993-06-30 Sapec S.A. Fine Chemicals Process for the preparation of pure diasteroisomers of tetrahydrofolates
EP0548895A3 (en) * 1991-12-21 1993-08-11 Sapec S.A. Fine Chemicals Process for the preparation of pure diasteroisomers of tetrahydrofolates

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