BE533436A - - Google Patents
Info
- Publication number
- BE533436A BE533436A BE533436DA BE533436A BE 533436 A BE533436 A BE 533436A BE 533436D A BE533436D A BE 533436DA BE 533436 A BE533436 A BE 533436A
- Authority
- BE
- Belgium
- Prior art keywords
- ethylenediamine
- bis
- pyridoyl
- mixture
- benzene
- Prior art date
Links
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- -1 3-pyridoyl Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000000203 mixture Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000000047 product Substances 0.000 description 6
- 239000001184 potassium carbonate Substances 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- PVNIIMVLHYAWGP-UHFFFAOYSA-N nicotinic acid Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 4
- ATBIAJXSKNPHEI-UHFFFAOYSA-N pyridine-3-carbonyl chloride Chemical compound ClC(=O)C1=CC=CN=C1 ATBIAJXSKNPHEI-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 230000004927 fusion Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N 1,2-ethanediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 125000003916 ethylene diamine group Chemical group 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 235000001968 nicotinic acid Nutrition 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 125000004433 nitrogen atoms Chemical group N* 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- 206010010904 Convulsion Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 239000012223 aqueous fraction Substances 0.000 description 1
- SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000036461 convulsion Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000727 fraction Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
<Desc/Clms Page number 1>
EMI1.1
La présente invention se rapporte t.des dérivés de l'éthylénediamine. Ces produits sont des st%fi3ants cardiaques; ils présentent, par rapport aux produits connus, l'avantage d'une différence très sensible entre la dose active et la dose provoquant des convulsions.
Les produits de la présente invention peuvent être représentés par la formule générale
EMI1.2
dans laquelle X désigne un radical alcoyle ou aralcoyle.
Les produits sont obtenus en condensant une éthylène-diamine substituée sur les deux atomes d'azote avec le chlorure de l'acide nicotinique.
EMI1.3
Exemple j,.
Dans 50 cm3 de toluène, on dissout 17 g de chlorure de l'acide nicotinique. On ajoutera cette solution 8,6 g de N, N'mdibutyhéthylénediaminet. On laisse reposer 20 heures. On traite la masse par 100 cm3 d'une solution aqueuse saturée de carbonate de potassium On décante la couche organique, on sèche sur du carbonate de potassium anhydre, on filtre et
EMI1.4
on distille sous vide. On recueille 7,1 g de N,N'bis-(3pyridoyl)-N,N'- dibutyl-éthylènediamine distillant à 220 C/0,003 mm Hg.
Exemple 2.
On dissout 37 g d'acide nicotinique dans 200 cm3 de chlorure de thionyle. On chauffe à reflux pendant 2 heures, puis on évapore l'excès de chlorure de thionyle. On reprend le résidu par le benzène anhydre 'et on évapore à sec le chlorhydrate du chlorure de l'acide nicotinique.
On reprend le produit obtenu par 300 cm3 de pyridine, On chauffe le mélange pendant une heure à 100 C On y introduit ensuite avec agita-
EMI1.5
tion 22,8 g de N,N'-dihexyl(n)-éthyl,ène-diamine et on continue le chauffa - ge pendant une heure au bain-marié.
Après refroidissement, on traite la masse par 100 cm3 d'une solution aqueuse saturée de carbonate de potassium et on continue comme il est décrit dans l'exemple 1.
EMI1.6
On obtient 29,5 g de N, N'-bis6-pyridoyl)-N,N'-dihexyl(n)-étbylènediamine dont le point d'ébullition est de 242-245C/0,01 mm Hg.
Exemple 3,
On mélange 30 g de chlorure de l'acide nicotinique, 35 cm3 de benzène et 45 cm3 de pyridine ssche, On porte le tout à 80 C et on y introduit sous agitation énergique 15, 8 g de N,N'-dibenzyl-éthylènedia-
EMI1.7
mine (Pt Ebull. 21Lr2l6 C) dissous dans 25 cm3 de pyridine sche. On chauffe à 110 C pendant 90 minutes. Après refroidissement, on ajoute 100 cm3 de benzènec puis 140 cm3 d'une solution aqueuse contenant 50% de carbonate de potassium, on laisse décanter et on extrait deux fois la fraction aqueuse avec 75 cm3 de benzène. Les liquides d'extraction et la fraction organique sont séchés sur du carbonate de potassium sec.
On filtre, on chasse le solvant sous pression réduite. On reprend le résidu par 100 cm3 de benzène et on chasse de nouveau le solvant sous pression réduite pour éliminer les dernières traces de pyridine. On redissout le résidu dans 250 em3 d'alcool, on ajoute 5 g de noir animal, on porte à l'ébullition et on filtre à chaud. Au filtrat, on ajoute 300 cm3
EMI1.8
d'eau. Le N, N'-bis-(3-pyridoyl)-N, NI-dibenzyl-éthylènediamîne cristallise,
<Desc/Clms Page number 2>
EMI2.1
on obtient finalement 19,2 g de produit fondant à 1,.3m7.1,., C.
Exemple 4.
Suivant les méthodes décrites dans les exemples 1 à 3 on prépare les composés suivants :
EMI2.2
N, N-bis-(3-pyridoyl)-N N'-diéthyl-éthylènediamine Pt Ebull. 205-210 C/0,004 mn Hg.
N, N'-bis (3-pyridoyl)-N, N'-diisopropyl-éthylènediamine Pt Fusion 179-180 C après recristallisation dans un mélange alcool-eau.
EMI2.3
N, N'-bis-(,3pyridoyl)-N,N =di-(seo-butyl)-éthynediamine Pt Fusion 146-147 C après recristallisation dans un mélange eau-alcool. ,
EMI2.4
N,N'-bise(3-p.yridoyl)-N,N =diheptyl(n)-éthylènediamine P4^EiJulle 263-265OG/0,005 mm Hg.
Pt Fusion 52-53 C après cristallisation dans un mélange de benzène-hexane.
R é s u m é
EMI2.5
1 Nouveaux dérivés de 1-'éthyleneediamine répondant à la formule générale
EMI2.6
où X = radical alcoyle ou aralcoyle.
@ 2 Procédé de préparation de dérivés de l'éthylènediamine tels- que décrits en 1 , caractérisé en ce que l'on fait réagir le chlorure de l'acide nicotinique avec une éthylènediamine substituée sur les deux atomes d'azote.
**ATTENTION** fin du champ DESC peut contenir debut de CLMS **.
<Desc / Clms Page number 1>
EMI1.1
The present invention relates to derivatives of ethylenediamine. These products are cardiac stabilizers; they have, compared to known products, the advantage of a very significant difference between the active dose and the dose causing convulsions.
The products of the present invention can be represented by the general formula
EMI1.2
in which X denotes an alkyl or aralkyl radical.
The products are obtained by condensing an ethylene diamine substituted on the two nitrogen atoms with the chloride of nicotinic acid.
EMI1.3
Example j ,.
In 50 cm3 of toluene, 17 g of nicotinic acid chloride are dissolved. This solution will be added 8.6 g of N, N'mdibutyhéthylénediaminet. Leave to stand for 20 hours. The mass is treated with 100 cm3 of a saturated aqueous solution of potassium carbonate The organic layer is decanted, dried over anhydrous potassium carbonate, filtered and
EMI1.4
it is distilled under vacuum. 7.1 g of N, N'bis- (3pyridoyl) -N, N'-dibutyl-ethylenediamine are collected, distilling at 220 C / 0.003 mm Hg.
Example 2.
37 g of nicotinic acid are dissolved in 200 cm3 of thionyl chloride. The mixture is heated under reflux for 2 hours, then the excess thionyl chloride is evaporated off. The residue is taken up in anhydrous benzene 'and the hydrochloride of nicotinic acid chloride is evaporated to dryness.
The product obtained is taken up in 300 cm3 of pyridine, the mixture is heated for one hour at 100 C. The mixture is then introduced with stirring.
EMI1.5
tion 22.8 g of N, N'-dihexyl (n) -ethyl, ene-diamine and heating is continued for one hour in a water bath.
After cooling, the mass is treated with 100 cm 3 of a saturated aqueous solution of potassium carbonate and the process is continued as described in Example 1.
EMI1.6
29.5 g of N, N'-bis6-pyridoyl) -N, N'-dihexyl (n) -étbylenediamine are obtained, the boiling point of which is 242-245C / 0.01 mm Hg.
Example 3,
30 g of nicotinic acid chloride, 35 cm3 of benzene and 45 cm3 of dry pyridine are mixed, the whole is brought to 80 ° C. and 15.8 g of N, N'-dibenzyl-ethylenedia are introduced with vigorous stirring. -
EMI1.7
mine (Pt Ebull. 21Lr2l6 C) dissolved in 25 cm3 of dry pyridine. Heated to 110 C for 90 minutes. After cooling, 100 cm3 of benzene are added and then 140 cm3 of an aqueous solution containing 50% of potassium carbonate, the mixture is allowed to settle and the aqueous fraction is extracted twice with 75 cm3 of benzene. The extraction liquids and the organic fraction are dried over dry potassium carbonate.
Filtered, the solvent is removed under reduced pressure. The residue is taken up in 100 cm3 of benzene and the solvent is removed again under reduced pressure to remove the last traces of pyridine. The residue is redissolved in 250 em3 of alcohol, 5 g of animal charcoal are added, the mixture is brought to the boil and filtered while hot. 300 cm3 are added to the filtrate
EMI1.8
of water. N, N'-bis- (3-pyridoyl) -N, NI-dibenzyl-ethylenediamine crystallizes,
<Desc / Clms Page number 2>
EMI2.1
finally obtained 19.2 g of product melting at 1, .3m7.1,., C.
Example 4.
According to the methods described in Examples 1 to 3, the following compounds are prepared:
EMI2.2
N, N-bis- (3-pyridoyl) -N N'-diethyl-ethylenediamine Pt Ebull. 205-210 C / 0.004 min Hg.
N, N'-bis (3-pyridoyl) -N, N'-diisopropyl-ethylenediamine Pt Fusion 179-180 C after recrystallization from an alcohol-water mixture.
EMI2.3
N, N'-bis - (, 3pyridoyl) -N, N = di- (seo-butyl) -ethynediamine Pt Fusion 146-147 C after recrystallization in a water-alcohol mixture. ,
EMI2.4
N, N'-bise (3-p.yridoyl) -N, N = diheptyl (n) -ethylenediamine P4 ^ EiJulle 263-265OG / 0.005 mm Hg.
Pt Fusion 52-53 C after crystallization from a mixture of benzene-hexane.
Summary
EMI2.5
1 New derivatives of 1-'ethyleneediamine corresponding to the general formula
EMI2.6
where X = alkyl or aralkyl radical.
@ 2 Process for the preparation of ethylenediamine derivatives as described in 1, characterized in that the nicotinic acid chloride is reacted with an ethylenediamine substituted on the two nitrogen atoms.
** ATTENTION ** end of DESC field can contain start of CLMS **.
Claims (1)
Publications (1)
Publication Number | Publication Date |
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BE533436A true BE533436A (en) |
Family
ID=165150
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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BE533436D BE533436A (en) |
Country Status (1)
Country | Link |
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BE (1) | BE533436A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3697531A (en) * | 1971-02-25 | 1972-10-10 | Sterling Drug Inc | N,n{40 -alkylenebis(pyridine-carboxamides) |
-
0
- BE BE533436D patent/BE533436A/fr unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3697531A (en) * | 1971-02-25 | 1972-10-10 | Sterling Drug Inc | N,n{40 -alkylenebis(pyridine-carboxamides) |
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