BE864399A - PROCESS FOR PREPARATION OF IMIDIC DERIVATIVES OF DIAMINOPRYRIDINES AND USE OF THESE DERIVATIVES IN HUMAN AND VETERINARY MEDICINE - Google Patents
PROCESS FOR PREPARATION OF IMIDIC DERIVATIVES OF DIAMINOPRYRIDINES AND USE OF THESE DERIVATIVES IN HUMAN AND VETERINARY MEDICINEInfo
- Publication number
- BE864399A BE864399A BE185543A BE185543A BE864399A BE 864399 A BE864399 A BE 864399A BE 185543 A BE185543 A BE 185543A BE 185543 A BE185543 A BE 185543A BE 864399 A BE864399 A BE 864399A
- Authority
- BE
- Belgium
- Prior art keywords
- emi
- anhydride
- pyrimethamine
- dicarboxylic acid
- derivatives
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
Procédé de préparation de dérivés imidiques des diaminopyridines et utilisation de ces dérivés
en médecine humaine et vétérinaire La présente invention concerne un procédé d'obtention de dérivés imidiques des diaminopyridines,
<EMI ID=1.1>
La présente invention se rapporte aussi aux composés obtenus par mise en oeuvre du procédé selon la présente invention.
Les dérivés imidiques susmentionnés sont intéressants en médecine humaine et vétérinaire, en raison de leur activité contre des bactéries et des protozoaires.
Le procédé conforme à la présente invention se caractérise en ce que l'on fait réagir la diaminopyrimidine sur un anhydride de la formule générale suivante :
<EMI ID=2.1>
dans laquelle X représente un groupe hydrocarboné.
La réaction se réalise de préférence à chaud
et en utilisant un solvant polaire, choisi, de préférence, parmi le dioxanne, le diméthylformamide, la méthylisobutylcétone, la méthyléthylcétone ou la pyridine, <EMI ID=3.1>
selon le schéma réactionnel suivant :
<EMI ID=4.1>
DIAVERIDINE
<EMI ID=5.1>
<EMI ID=6.1>
<EMI ID=7.1>
Les exemples qui suivent permettront de
mieux comprendre la mise en oeuvre du procédé conforme à la présente invention. Il est cependant bien entendu que ces exemples ne possèdent qu'un caractère purement illustratif et qu'il ne faut pas les considérer comme limitant l'invention d'une manière quelconque.
Par conséquent, le spécialiste de la technique pourra apporter aux détails de mise en oeuvre décrits dans ces exemples de nombreuses modifications et variantes que l'expérience lui conseillera, sans pour autant sortir du cadre et de l'esprit de l'invention. EXEMPLE 1
Obtention du diavéridine-2-phtalimide
On a dissous 26 g de diavéridine (0,1 mole) dans 500 ml de dioxanne et on a ajouté 14,8 g (0,1 mole) d'anhydride phtalique à cette solution.
On a agité le mélange réactionnel et on l'a chauffé au reflux pendant 10 heures, période au bout
de laquelle on l'a refroidi et on a filtré le liquide pour le concentrer ensuite jusqu'au tiers de son volume. On a ajouté de l'acétate d'éthyle et le refroidissement du mélange a amorcé une cristallisation. On a filtré
<EMI ID=8.1> EXEMPLE 2
Obtention du pyriméthamine-2-phtalimide
On a dissous 24,85 g (0,1 mole) de pyriméthamine dans 500 ml de dioxanne et on a ajouté 14,8 g
(0,1 mole) d'anhydride phtalique à la solution. On a agité et chauffé le mélange réactionnel au reflux durant 8 heures, et on a vérifié la fin de.la réaction par chromatographie en couche mince.
On a refroidi le mélange réactionnel et on l'a filtré. On a concentré le liquide clair obtenu sous pression réduite jusqu'au tiers de son volume.
L'addition subséquente d'éther de pétrole
a amorcé une cristallisation qui se termina par la précipitation du produit. On a filtré le produit ainsi obtenu et on l'a lavé à l'éther, de façon à obtenir une substance cristalline blanche possédant un point de fusion de 230-231[deg.]C.
<EMI ID=9.1>
Trouvé : C 60,81 % ; H 3,75 % ; N 14,02 % ; Cl 8,93 % .
EXEMPLE 3
Obtention du diavéridine-2-succinimide
<EMI ID=10.1>
^mélange au reflux sous agitation pendant 6 heures, période au bout de laquelle ou a filtré le mélange et on a concentré le filtrat sous vide jusqu'à consistance sirupeuse. L'addition d'un mélange d'acétone et d'acétate.
<EMI ID=11.1>
Process for the preparation of imide derivatives of diaminopyridines and use of these derivatives
in human and veterinary medicine The present invention relates to a process for obtaining imide derivatives of diaminopyridines,
<EMI ID = 1.1>
The present invention also relates to the compounds obtained by carrying out the process according to the present invention.
The aforementioned imidic derivatives are of interest in human and veterinary medicine, due to their activity against bacteria and protozoa.
The process in accordance with the present invention is characterized in that the diaminopyrimidine is reacted with an anhydride of the following general formula:
<EMI ID = 2.1>
in which X represents a hydrocarbon group.
The reaction is preferably carried out hot
and using a polar solvent, preferably chosen from dioxane, dimethylformamide, methyl isobutyl ketone, methyl ethyl ketone or pyridine, <EMI ID = 3.1>
according to the following reaction scheme:
<EMI ID = 4.1>
DIAVERIDINE
<EMI ID = 5.1>
<EMI ID = 6.1>
<EMI ID = 7.1>
The following examples will help to
better understand the implementation of the method according to the present invention. However, it is understood that these examples are purely illustrative and should not be considered as limiting the invention in any way.
Consequently, the person skilled in the art will be able to make numerous modifications and variations to the details of implementation described in these examples that experience will advise him, without departing from the scope and the spirit of the invention. EXAMPLE 1
Obtaining diaveridin-2-phthalimide
26 g of diaveridin (0.1 mole) was dissolved in 500 ml of dioxane and 14.8 g (0.1 mole) of phthalic anhydride was added to this solution.
The reaction mixture was stirred and heated to reflux for 10 hours, period after
from which it was cooled and the liquid was filtered to then concentrate it to one third of its volume. Ethyl acetate was added and cooling of the mixture initiated crystallization. We filtered
<EMI ID = 8.1> EXAMPLE 2
Obtaining pyrimethamine-2-phthalimide
24.85 g (0.1 mole) of pyrimethamine was dissolved in 500 ml of dioxane and 14.8 g was added.
(0.1 mol) of phthalic anhydride to solution. The reaction mixture was stirred and heated under reflux for 8 hours, and the completion of the reaction was verified by thin layer chromatography.
The reaction mixture was cooled and filtered. The obtained clear liquid was concentrated under reduced pressure to a third of its volume.
The subsequent addition of petroleum ether
initiated crystallization which ended in precipitation of the product. The product thus obtained was filtered and washed with ether, so as to obtain a white crystalline substance having a melting point of 230-231 [deg.] C.
<EMI ID = 9.1>
Found: C 60.81%; H 3.75%; N 14.02%; Cl 8.93%.
EXAMPLE 3
Obtaining diaveridin-2-succinimide
<EMI ID = 10.1>
Mixture under reflux with stirring for 6 hours, after which time the mixture was filtered and the filtrate was concentrated in vacuo to syrupy consistency. The addition of a mixture of acetone and acetate.
<EMI ID = 11.1>
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES457222A ES457222A1 (en) | 1977-03-25 | 1977-03-25 | Procedure for the obtaining of imidic derivatives of diaminopirimidinas. (Machine-translation by Google Translate, not legally binding) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE864399A true BE864399A (en) | 1978-06-16 |
Family
ID=8473426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE185543A BE864399A (en) | 1977-03-25 | 1978-02-28 | PROCESS FOR PREPARATION OF IMIDIC DERIVATIVES OF DIAMINOPRYRIDINES AND USE OF THESE DERIVATIVES IN HUMAN AND VETERINARY MEDICINE |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE864399A (en) |
| ES (1) | ES457222A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002074753A3 (en) * | 2001-03-15 | 2002-12-27 | Basf Ag | 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi |
-
1977
- 1977-03-25 ES ES457222A patent/ES457222A1/en not_active Expired
-
1978
- 1978-02-28 BE BE185543A patent/BE864399A/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002074753A3 (en) * | 2001-03-15 | 2002-12-27 | Basf Ag | 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi |
| US7153860B2 (en) | 2001-03-15 | 2006-12-26 | Basf Aktiengesellschaft | 5-Phenylpyrimidines, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi |
| EA007719B1 (en) * | 2001-03-15 | 2006-12-29 | Басф Акциенгезельшафт | 5-phenylpyrimidine, methods and intermediate products for the production thereof and use of the same for controlling pathogenic fungi |
| US7709637B2 (en) | 2001-03-15 | 2010-05-04 | Basf Se | 5-phenylpyrimidines, their preparation, intermediates for their preparation, and their use for controlling harmful fungi |
Also Published As
| Publication number | Publication date |
|---|---|
| ES457222A1 (en) | 1978-01-16 |
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