CH306561A - Process for the preparation of a new pyridine-3,5-dicarboxylic acid diamide. - Google Patents
Process for the preparation of a new pyridine-3,5-dicarboxylic acid diamide.Info
- Publication number
- CH306561A CH306561A CH306561DA CH306561A CH 306561 A CH306561 A CH 306561A CH 306561D A CH306561D A CH 306561DA CH 306561 A CH306561 A CH 306561A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- pyridine
- dicarboxylic acid
- compound
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- ANNOWMBWHHKGLN-UHFFFAOYSA-N pyridine-3,5-dicarboxamide Chemical compound NC(=O)C1=CN=CC(C(N)=O)=C1 ANNOWMBWHHKGLN-UHFFFAOYSA-N 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- 238000000354 decomposition reaction Methods 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- ACXCKRZOISAYHH-UHFFFAOYSA-N molecular chlorine hydrate Chemical compound O.ClCl ACXCKRZOISAYHH-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- WHKWMTXTYKVFLK-UHFFFAOYSA-N 1-propan-2-ylpiperazine Chemical compound CC(C)N1CCNCC1 WHKWMTXTYKVFLK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- GHKOMFAUZDGVHG-UHFFFAOYSA-N 5-ethoxycarbonylpyridine-3-carboxylic acid Chemical compound CCOC(=O)C1=CN=CC(C(O)=O)=C1 GHKOMFAUZDGVHG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- DUAJIKVIRGATIW-UHFFFAOYSA-N trinitrogen(.) Chemical compound [N]=[N+]=[N-] DUAJIKVIRGATIW-UHFFFAOYSA-N 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines neuen Pyridin-3,5-diearbonsäurediamids. Das vorliegende Patent betrifft ein vorteilhaftes Verfahren zur Herstellung der Ver bindung der Formel
EMI0001.0002
welches dadurch gekennzeichnet ist, dass man eine Verbindung der allgemeinen Formel
EMI0001.0004
in welcher Am einer der Aminogruppen in Formel I entspricht und X einen reaktions fähigen, leicht abspaltbaren Rest. bedeutet, wie zum Beispiel ein Halogenatom, das Hydroxyl-, ein Alkoxy-, ein Acyloxy- oder das Azidoradi- kal,
mit einer Verbindung der Formel AM-EI III in welcher Am der andern Aminogruppe in der Formel I entspricht, umsetzt.
-Man kann zur Ausführung des erfindungs gemässen Verfahrens also entweder eine Ver bindung der Formel
EMI0001.0016
in welcher X die bereits definierte Bedeutung zukommt, mit Ammoniak umsetzen oder aber eine Verbindung der Formel
EMI0001.0017
in welcher X die bereits definierte Bedeutung zukommt mit dem Amin der Formel
EMI0001.0019
Der Umsatz erfolgt vorteilhaft in An wesenheit eines Lösungs- bzw. Verdünnungs mittels und in Gegenwart eines Kondensa tionsmittels. Eventuell ist es auch zweck mässig, unter erhöhtem Druck und erhöhter Temperatur zu arbeiten.
Das neue Pyridin-3,5-dicarbonsäiireamid soll als Arzneimittel Verwendung finden. Beispiel <I>1:</I> Das aus<B>1.0</B> g Pyridin-3,5-dicarbonsäure-3- äthylester, 15,3 g Thionylchlorid und 6,6 g N-Isopropylpiperazin in zwei Operationen ge wonnene Pyridin-3,5-clicarbonsäure-3-äthyl- ester - 5 - (4' - isopropyl-piperazid) wird mit 50 cms Äthanol und 100 cm33 konz. wässerigem Ammoniak bis zur Lösung geschüttelt und über Nacht stehen gelassen.
Darauf wird das Reaktionsgemisch zur Trockne verdampft und der Rückstand, welcher eine amorphe Masse bildet, in absolutem Äthanol aufgenommen und mit äthanoliseher Salzsäure versetzt, bis die Lösung schwaeh sauer reagiert. Dann wer den in kleinen Portionen 400 cm3 Äther 7u- gesetzt, die Fällung abgenutseht und im E1- siceator getrocknet.
Nach zweimaligem Um kristallisieren aus absol. Äthanol erhält man das bei 218 unter Zersetzung schmelzende Pyridin-3,5-dica.rbonsäui-e-3-amid-5-(I'-isopro- pyl-piperazid)-hydroclilorid in guter Aus beute.
Beispiel <I>2:</I> Durch Umsetzen von 0,5 --Hol Pyridin-3,5- diearbonsäure-3-amid-5-phen v lester mit 1 11o1 N-Isopropylpiperazin bei 1N0-180 im Auto klaven und Aufarbeitung, wie in Beispiel 1 beschrieben, gelangt man ebenfalls zum Pyri- din-3,5-dicarbonsäure - 3 - amid-5- (4'-isopropyl- piperazid)-hydroehloi-id.
Process for the preparation of a new pyridine-3,5-diacid diamide. The present patent relates to an advantageous process for the preparation of the compound of the formula Ver
EMI0001.0002
which is characterized in that one is a compound of the general formula
EMI0001.0004
in which Am corresponds to one of the amino groups in formula I and X is a reactive, easily cleavable radical, such as a halogen atom, the hydroxyl, an alkoxy, an acyloxy or the azido radical,
with a compound of the formula AM-EI III in which Am corresponds to the other amino group in the formula I, reacts.
You can either use a compound of the formula to carry out the process according to the invention
EMI0001.0016
in which X has the meaning already defined, react with ammonia or a compound of the formula
EMI0001.0017
in which X has the meaning already defined with the amine of the formula
EMI0001.0019
The conversion takes place advantageously in the presence of a solvent or diluent and in the presence of a condensation agent. It may also be useful to work under increased pressure and temperature.
The new pyridine-3,5-dicarboxamide is said to be used as a drug. Example <I> 1: </I> The obtained from <B> 1.0 </B> g of 3-ethyl pyridine-3,5-dicarboxylate, 15.3 g of thionyl chloride and 6.6 g of N-isopropylpiperazine in two operations recovered pyridine-3,5-clicarboxylic acid 3-ethyl ester - 5 - (4 '- isopropyl-piperazid) is concentrated with 50 cms of ethanol and 100 cm33. aqueous ammonia shaken until dissolved and left to stand overnight.
The reaction mixture is then evaporated to dryness and the residue, which forms an amorphous mass, is taken up in absolute ethanol and treated with ethanolic hydrochloric acid until the solution reacts slightly acidic. Then 400 cm3 of ether 7u are added in small portions, the precipitate is sutured off and dried in the E1-siceator.
After two recrystallize from absol. In ethanol, the pyridine-3,5-dica.rbonsäui-e-3-amide-5- (I'-isopropyl-piperazid) hydrochloride, which melts with decomposition at 218, is obtained in good yield.
Example <I> 2: </I> By reacting 0.5 -Hol pyridine-3,5-diacid 3-amide-5-phenyl ester with 11101 N-isopropylpiperazine at 1N0-180 in the car and Working up as described in Example 1 also leads to pyridine-3,5-dicarboxylic acid - 3 - amide-5- (4'-isopropylpiperazid) -hydroehloi-id.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284073T | 1950-04-20 | ||
| CH306561T | 1950-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306561A true CH306561A (en) | 1955-04-15 |
Family
ID=25732331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306561D CH306561A (en) | 1950-04-20 | 1950-07-26 | Process for the preparation of a new pyridine-3,5-dicarboxylic acid diamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH306561A (en) |
-
1950
- 1950-07-26 CH CH306561D patent/CH306561A/en unknown
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