DE897407C - Process for the preparation of 4- (pyridine-3'-carboxylic acid amido or -alkylamido) -2, 3-dimethyl-1-phenyl-5-pyrazolones - Google Patents
Process for the preparation of 4- (pyridine-3'-carboxylic acid amido or -alkylamido) -2, 3-dimethyl-1-phenyl-5-pyrazolonesInfo
- Publication number
- DE897407C DE897407C DEH9244A DEH0009244A DE897407C DE 897407 C DE897407 C DE 897407C DE H9244 A DEH9244 A DE H9244A DE H0009244 A DEH0009244 A DE H0009244A DE 897407 C DE897407 C DE 897407C
- Authority
- DE
- Germany
- Prior art keywords
- pyridine
- phenyl
- carboxylic acid
- pyrazolones
- alkylamido
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Verfahren zur Darstellung von 4-(Pyridin-3'-carbonsäureamido-bzw. -alkylamido)-2, 3-dimethyl-l-phenyl-5-pyrazolonen Aus der Patentschrift 351 085 ist die Darstellung von Dialkylamiden der Pyridin-3-carbonsäure (Nicotinsäure) bekannt. Zur Gewinnung derartiger Verbindungen, die sich therapeutisch durch Blutdrucksteigerung und Erregung des Zentralnervensystems auszeichnen, wird z. B. Pyridin-3-carbonsäure-chlorid mit der äquivalenten Menge Diäthylaminchlorhydrat auf 16o° erhitzt und aus der Schmelze Pyridin-3-carbonsäure-diäthylamid als gelbliches Öl vom Siedepunkt 28o° abgeschieden.Process for the preparation of 4- (pyridine-3'-carboxamido- or -alkylamido) -2, 3-dimethyl-1-phenyl-5-pyrazolones Patent 351 085 describes the preparation of dialkylamides of pyridine-3-carboxylic acid ( Nicotinic acid). To obtain such compounds, which are therapeutically characterized by an increase in blood pressure and excitation of the central nervous system, z. B. Pyridine-3-carboxylic acid chloride with the equivalent amount of diethylamine chlorohydrate is heated to 160 ° and pyridine-3-carboxylic acid diethylamide is deposited as a yellowish oil with a boiling point of 280 ° from the melt.
Es wurde nun gefunden, daB Basen vom Typ des 4-Amino-i-phenyl-2, 3-dimethylpyrazolons, welches durch Reduktion der 4-Nitrosoverbindung z. B. nach Liebigs Annalen 238, 212 (z886) und 293, 58 (1896) und der Patentschrift 71 261 oder nach Bull. Soc. chim. France (q.) 39, 321 (1926) erhalten wird, bzw. der 4-Monoallcylamino-z-phenyl-2, 3-dimethylpyrazotone, welche sich z. B. nach der Patentschrift 145 603 darstellen lassen, mit Pyridin-3-carbonsäurehalogeniden in Gegenwart von Pyridin zu 4.-(Pyridin-3-carbonsäureamido- bzw. -alkylamido)-2, 3-dimethyli-phenyl-5-pyrazolonen reagieren.It has now been found that bases of the 4-amino-i-phenyl-2, 3-dimethylpyrazolone type, which can be obtained by reducing the 4-nitroso compound, for. B. after Liebigs Annalen 238, 212 (z886) and 293, 58 (1896) and the patent specification 71 261 or after Bull. Soc. chim. France (q.) 39, 321 (1926), or the 4-Monoallcylamino-z-phenyl-2,3-dimethylpyrazotone, which z. B. can represent according to patent specification 145 603 , react with pyridine-3-carboxylic acid halides in the presence of pyridine to 4 .- (pyridine-3-carboxylic acid amido or -alkylamido) -2, 3-dimethyli-phenyl-5-pyrazolones.
Man erhält die neuen Verbindungen, indem man z. B. Pyridin-3-carbonsäurechlorid in trockenem, mit aromatischen Kohlenwasserstoffen, wie Benzol, Toluol n. ä., verdünntem Pyridin als Kondensations- und Säurebindungsmittel mit q. - Amino - 2, 3 - dimethyli-phenyl-5-pyrazolon bei o° umsetzt und das Reaktionsprodukt durch Umkristallisieren reinigt.The new compounds are obtained by z. B. pyridine-3-carboxylic acid chloride in dry, diluted with aromatic hydrocarbons such as benzene, toluene, etc. Pyridine as a condensation and acid binding agent with q. - Amino - 2, 3 - dimethyli-phenyl-5-pyrazolone at 0 ° and the reaction product is purified by recrystallization.
Nach den dafür üblichen Verfahren gelingt es, die in Wasser und Äther schwer löslichen Verbindungen in wasserlösliche Salze der Chlorwasserstoffsäure, Schwefelsäure, Phosphorsäure u. ä. durch Behandeln der Basen in alkoholischer Lösung, die die wasserfreie Säure enthält, umzuwandeln. Der Geschmack der freien Basen ist bitter, der der Salze bitter und schwach adstringierend.According to the usual procedures it succeeds in water and ether poorly soluble compounds in water-soluble salts of hydrochloric acid, Sulfuric acid, phosphoric acid, etc. by treating the bases in an alcoholic solution, the the anhydrous Contains acid to convert. The taste of the The free base is bitter, the salt bitter and weakly astringent.
Die so erhaltenen Verbindungen zeichnen sich durch eine hoch analgetische und spasmenlösende Eigenschaft aus und können zur Herstellung von Arzneimitteln Verwendung finden. Beispiel 5 g Pyridin-3-carbonsäurechlorid werden in 6 ccm trockenem, eiskaltem Pyridin gelöst, 25 ccm Toluol zugegeben und 7 g 4-Amino-2, 3-dimethyl-i-phenyl-5-pyrazolon eingetragen. Bei Eiskühlung und Rühren löst sich letztere Substanz auf, und das 4-(Pyridin-3' - carbonsäureamido) -2, 3-dimethyl-i-phenyl-5-pyrazolon kristallisiert aus. Man wäscht zuerst mitÄther, dann mit Wasser und kristallisiert zuletzt io g Rohprodukt aus 6o ccm 5oa/oigem Alkohol um. Ausbeute 7o bis 8o °/o der Theorie. Schmelzpunkt 25o°.The compounds obtained in this way are highly analgesic and antispasmodic property and can be used in the manufacture of drugs Find use. Example 5 g of pyridine-3-carboxylic acid chloride are in 6 ccm of dry, dissolved in ice-cold pyridine, added 25 cc of toluene and 7 g of 4-amino-2,3-dimethyl-i-phenyl-5-pyrazolone registered. With ice cooling and stirring, the latter substance dissolves, and that 4- (Pyridine-3'-carboxamido) -2, 3-dimethyl-i-phenyl-5-pyrazolone crystallized the end. It is washed first with ether, then with water, and finally io g is crystallized Crude product from 60 ccm 50o per cent alcohol. Yield 70 to 80 percent of theory. Melting point 25o °.
Claims (1)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH9244A DE897407C (en) | 1951-02-06 | 1951-02-06 | Process for the preparation of 4- (pyridine-3'-carboxylic acid amido or -alkylamido) -2, 3-dimethyl-1-phenyl-5-pyrazolones |
| CH322063D CH322063A (en) | 1951-02-06 | 1953-11-15 | Process for the preparation of 4- (pyridine-3-carboxamido or -alkylamido) -2,3-dimethyl-1-phenyl-5-pyrazolone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEH9244A DE897407C (en) | 1951-02-06 | 1951-02-06 | Process for the preparation of 4- (pyridine-3'-carboxylic acid amido or -alkylamido) -2, 3-dimethyl-1-phenyl-5-pyrazolones |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE897407C true DE897407C (en) | 1953-11-19 |
Family
ID=7145878
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH9244A Expired DE897407C (en) | 1951-02-06 | 1951-02-06 | Process for the preparation of 4- (pyridine-3'-carboxylic acid amido or -alkylamido) -2, 3-dimethyl-1-phenyl-5-pyrazolones |
Country Status (2)
| Country | Link |
|---|---|
| CH (1) | CH322063A (en) |
| DE (1) | DE897407C (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1046058B (en) * | 1957-02-08 | 1958-12-11 | Peter Stoltenberg Chem Fab | Process for the preparation of 4- (Pyridincarbonsaeureamido- or. -Alkylamido) -1-phenyl-2,3-dimethylpyrazolonen- (5) |
| DE1272926B (en) * | 1963-10-31 | 1968-07-18 | Josef Klosa Dipl Chem Dr Rer N | Process for the preparation of water-soluble salts of pyridine-carboxylic acid-amido-2, 3-dimethyl-1-pheyl-5-pyrazolones |
-
1951
- 1951-02-06 DE DEH9244A patent/DE897407C/en not_active Expired
-
1953
- 1953-11-15 CH CH322063D patent/CH322063A/en unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1046058B (en) * | 1957-02-08 | 1958-12-11 | Peter Stoltenberg Chem Fab | Process for the preparation of 4- (Pyridincarbonsaeureamido- or. -Alkylamido) -1-phenyl-2,3-dimethylpyrazolonen- (5) |
| US2951845A (en) * | 1957-02-08 | 1960-09-06 | Peter Stoltenberg Fa | Production of 4-(pyridine carboxylic acid amido)-2, 3-dimethyl-1-phenyl-5-pyrazolones |
| DE1272926B (en) * | 1963-10-31 | 1968-07-18 | Josef Klosa Dipl Chem Dr Rer N | Process for the preparation of water-soluble salts of pyridine-carboxylic acid-amido-2, 3-dimethyl-1-pheyl-5-pyrazolones |
Also Published As
| Publication number | Publication date |
|---|---|
| CH322063A (en) | 1957-05-31 |
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