CH306558A - 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
- CH306558A CH306558A CH306558DA CH306558A CH 306558 A CH306558 A CH 306558A CH 306558D A CH306558D A CH 306558DA CH 306558 A CH306558 A CH 306558A
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- dicarboxylic acid
- pyridine
- preparation
- acid diamide
- 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 4
- 238000002360 preparation method Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 7
- 125000003277 amino group Chemical group 0.000 claims description 4
- MPFLRYZEEAQMLQ-UHFFFAOYSA-N dinicotinic acid Chemical compound OC(=O)C1=CN=CC(C(O)=O)=C1 MPFLRYZEEAQMLQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 239000013078 crystal Substances 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 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 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 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
- 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
- 238000001816 cooling Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 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)
- Hydrogenated Pyridines (AREA)
Description
Verfahren zur Herstellung eines neuen Pyridin-3,5-diearbonsäurediamids. Das vorliegende Patent betrifft ein vor teilhaftes Verfahren zur Herstellung der Ver bindung der Formel
EMI0001.0004
welches dadurch gekennzeichnet ist, dass man eine Verbindung der allgemeinen Formel
EMI0001.0005
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-H 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
EMI0001.0018
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-dicarbonsäureamid soll als Arzneimittel Verwendung finden. <I>Beispiel 1:</I> Das aus 100 g Pyridin-3,5-dicarbonsäure- äthylester, 121. g Thionylehlorid und 88 g Pi- peridin in 2 Operationen gewonnene Pyridin- 3,5-dicarbonsäure-3-äthylester-5-piperidid wird mit 500 cm3 Äthanol und 1000 em3 24 /aigem Ammoniak einige Stunden geschüttelt;
man verdampft gut zur Trockne und löst den glas artigen Rückstand in 50 cm3 Pyridin. Nach dem Erkalten versetzt man mit 500 cm3 Äther, dekantiert nach einigem Stehen das Lösungsmittel ab und versetzt mit frischem Äther, Die so erhaltenen Kristalle werden aus einem Gemisch von Chloroform/Äther/Petrol- äther umkristallisiert, wobei man das bei 112 bis 113 schmelzende Pyridin-3,5-dicarbon- säure-3-amid-5-piperidid in befriedigender Ausbeute gewinnt.
Beispiel <I>2: .</I>
Durch Umsetzen von 0,5 Mol Py ridin-3,5-di- carbonsäure-3-amid-5-phenylester mit 1Mol Pi- peridin bei 1.50-180 im Autoklaven und Auf arbeitung, wie in Beispiel 1 beschrieben, ge langt man ebenfalls zum Pyridin-3,5-dicar- bonsäure-3-amid-piperidid.
Process for the preparation of a new pyridine-3,5-diacid diamide. The present patent relates to an advantageous method for preparing the compound of the formula Ver
EMI0001.0004
which is characterized in that one is a compound of the general formula
EMI0001.0005
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-H III in which Am corresponds to the other amino group in the formula I.
. You can either use a compound of the formula to carry out the method according to the invention
EMI0001.0016
in which X has the meaning already defined, react with ammonia or a compound of the formula
EMI0001.0018
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 to be used as a drug. <I> Example 1: </I> The pyridine 3,5-dicarboxylic acid 3-ethyl ester obtained in 2 operations from 100 g pyridine-3,5-dicarboxylic acid ethyl ester, 121 g thionyl chloride and 88 g piperidine 5-piperidide is shaken with 500 cm3 of ethanol and 1000 cubic meters of 24 / aigem ammonia for a few hours;
it is evaporated to dryness and the glass-like residue is dissolved in 50 cm3 of pyridine. After cooling, 500 cm3 of ether are added, the solvent is decanted after standing for a while and fresh ether is added -3,5-dicarboxylic acid-3-amide-5-piperidide wins in a satisfactory yield.
Example <I> 2:. </I>
By reacting 0.5 mol of pyridine-3,5-dicarboxylic acid 3-amide-5-phenyl ester with 1 mol of piperidine at 1.50-180 in the autoclave and working up as described in Example 1, one also obtains to pyridine-3,5-dicarboxylic acid-3-amide-piperidide.
Claims (1)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH284073T | 1950-04-20 | ||
| CH306558T | 1950-07-26 | ||
| CH306559T | 1950-07-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH306558A true CH306558A (en) | 1955-04-15 |
Family
ID=27178156
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH306558D CH306558A (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) | CH306558A (en) |
-
1950
- 1950-07-26 CH CH306558D patent/CH306558A/en unknown
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