DE834102C - Process for the production of new tropic acid offshoots - Google Patents
Process for the production of new tropic acid offshootsInfo
- Publication number
- DE834102C DE834102C DEH7112A DEH0007112A DE834102C DE 834102 C DE834102 C DE 834102C DE H7112 A DEH7112 A DE H7112A DE H0007112 A DEH0007112 A DE H0007112A DE 834102 C DE834102 C DE 834102C
- Authority
- DE
- Germany
- Prior art keywords
- tropic acid
- new
- production
- picolyl
- offshoots
- 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
- 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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
Description
Verfahren zur Herstellung neuer Tropasäureabkömmlinge Die vorliegende Erfindung betrifft ein Verfahren zur Herstellung neuer Tropasäureabkömmlinge, nämlich von Tropasäure-N-alkyl-N-(ß-picolyl)-amiden, denen folgende Formel zukommt: R = niedriger Alkylrest.Process for the production of new tropic acid derivatives The present invention relates to a process for the production of new tropic acid derivatives, namely of tropic acid-N-alkyl-N- (ß-picolyl) -amides, which have the following formula: R = lower alkyl radical.
Diese Verbindungen sind wertvolle Arzneimittel, denn sie zeichnen sich durch ausgeprägte spasmolytische Wirkung und verhältnismäßig große therapeutische Breite aus.These compounds are valuable medicines because they draw through pronounced spasmolytic effect and relatively large therapeutic Width.
Gemäß der Erfindung können die neuen Verbindungen dadurch gewonnen werden, daß man, gegebenenfalls acetyliertes, Tropasäurechlorid mit einem Alkyl-(ß-picolyl)-amin umsetzt und gegebenenfalls das Kondensationsprodukt in an sich bekannter Weise entacetyliert. Insbesondere kann man also entweder Tropasänrechlorid mit einem Alkyl-(ß-picolyl)-amin zur Reaktion bringen oder Acetyltropasäurechlorid mit einem Alkyl-(ß-picolyl)-amin umsetzen und das Kondensationsprodukt zu Tropasäure-N-alkyl-N-(ß-picolyl)-amid hydrolysieren.According to the invention, the new compounds can thereby be obtained that one, optionally acetylated, tropic acid chloride with an alkyl (ß-picolyl) amine converts and, if appropriate, deacetylated the condensation product in a manner known per se. In particular, one can either use tropasene chloride with an alkyl (ß-picolyl) amine bring to reaction or acetyltropic acid chloride with an alkyl- (ß-picolyl) -amine convert and hydrolyze the condensation product to tropic acid-N-alkyl-N- (ß-picolyl) -amide.
Die als eines der Ausgangsmaterialien zu benutzenden Alkyl-(ß-picolyl)-amine können durch Umsetzung von 3-Halogenmethylpyridin mit einem primären Alkylamin gewonnen werden. Beispiel i Zu einer Lösung von 122 Gewichtsteilen Methyl-(ß-picolyl)-amin (KP" 93 bis 95° C) und ioo Gewichtsteilen trockenem Pyridin in 75o Gewichtsteilen trokkenem Chloroform wird das rohe, aus 166 Gewichtsteilen Tropasäure mit überschüssigem Thionylchlorid erhaltene Tropasäurechlorid unter Rühren eingetropft. Mit einem Eiswasserbad sorgt man dafür, daß die Temperatur 20° C nicht übersteigt.The alkyl (β-picolyl) amines to be used as one of the starting materials can be obtained by reacting 3-halomethylpyridine with a primary alkylamine will. Example i To a solution of 122 parts by weight of methyl (β-picolyl) amine (KP "93 to 95 ° C) and 100 parts by weight of dry pyridine in 750 parts by weight dry The crude chloroform is obtained from 166 parts by weight of tropic acid tropic acid chloride obtained with excess thionyl chloride was added dropwise with stirring. An ice water bath is used to ensure that the temperature does not exceed 20 ° C.
Nach beendeter Reaktion wird die Chloroformlösung mit Wasser gewaschen, mit 4oo Gewichtsteilen Äther verdünnt und mit 3 n-Salzsäure geschüttelt.After the reaction has ended, the chloroform solution is washed with water, diluted with 400 parts by weight of ether and shaken with 3N hydrochloric acid.
Die salzsaure Lösung wird nun mit aktiver Kohle versetzt und filtriert; zu dem Filtrate fügt man in der Kälte überschüssiges, konzentriertes Ammoniak, wobei das Tropasäure-N-methyl-N-(ß-picolyl)-amid ausfällt. Dieses wird in Chloroform aufgenommen, über Natriumsulfat getrocknet und durch Destillation vom Chloroform befreit. Durch Umlösen des Destillationsrückstandes in Essigester erhält man das Tropasäure-N-methyl-N-(ß-picolyl)-amid als farblose Kristalle vom Schmelzpunkt 92 bis 93° C.The hydrochloric acid solution is then mixed with active charcoal and filtered; excess, concentrated ammonia is added to the filtrate in the cold, whereby the tropic acid-N-methyl-N- (ß-picolyl) -amide precipitates. This is taken up in chloroform, dried over sodium sulfate and freed from chloroform by distillation. By The distillation residue is dissolved in ethyl acetate to obtain tropic acid-N-methyl-N- (ß-picolyl) -amide as colorless crystals with a melting point of 92 to 93 ° C.
Beispiel 2 Zu einer Mischung von 41 Gewichtsteilen Äthyl-(ß-picolyl)-amin (KP, 97 bis ioo° C) und 5o Gewichtsteilen trockenem Pyridin in 25o Gewichtsteilen trokkenem Chloroform wird das rohe, aus 50 Gewichtsteilen Tropasäure durch Einwirkung von Acetylchlorid und anschließende Behandlung mit überschüssigem Thionylchlorid erhaltene Acetyltropasäurechlorid unter Rühren und Eiswasserkühlung nach und nach zugegeben. Zum Schluß wird noch ',i'2 Stunde lang bei gewöhnlicher Temperatur gerührt.Example 2 To a mixture of 41 parts by weight of ethyl (ß-picolyl) amine (KP, 97 to 100 ° C) and 50 parts by weight of dry pyridine in 250 parts by weight of dry chloroform, the crude tropic acid from 50 parts by weight by the action of acetyl chloride and then Acetyltropic acid chloride obtained after treatment with excess thionyl chloride was gradually added with stirring and ice-water cooling. Finally, the mixture is stirred for 1 1/2 hours at ordinary temperature.
Dann wird die Chloroformlösung mit Wasser gewaschen, mit 200 Gewichtsteilen Äther verdünnt und mit 3 n-Salzsäure geschüttelt. Die schwach congosaure Lösung erwärmt man i Stunde lang auf dem Dampfbad, wobei die Acetylgruppe des Reaktionsproduktes abgespalten wird, filtriert über Kohle und versetzt mit überschüssigem, konzentriertem Ammoniak. Das ausgefallene Kondensationsprodukt wird in Chloroform aufgenommen, die Chloroformlösung mit Natriumsulfat getrocknet und destilliert. Der Destillationsrückstand, Tropasäure-N-äthyl-N-(ßpi-colyl)-amid, stellt ein dickes, gelbes 01 dar, dessen Chlorhydrat bei 156 bis i57° C schmilzt.The chloroform solution is then washed with water, diluted with 200 parts by weight of ether and shaken with 3N hydrochloric acid. The weakly congous acid solution is heated for one hour on the steam bath, the acetyl group of the reaction product being split off, filtered through charcoal and treated with excess, concentrated ammonia. The precipitated condensation product is taken up in chloroform, the chloroform solution is dried with sodium sulfate and distilled. The distillation residue, tropic acid-N-ethyl-N- (SSPI colyl) amide, provides a thick yellow 01 represents its hydrochloride to I57 ° C melts at 156th
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH281901T | 1950-04-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE834102C true DE834102C (en) | 1952-03-17 |
Family
ID=4483397
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH7112A Expired DE834102C (en) | 1950-04-25 | 1950-12-29 | Process for the production of new tropic acid offshoots |
Country Status (5)
| Country | Link |
|---|---|
| AT (2) | AT170881B (en) |
| CH (2) | CH281901A (en) |
| DE (1) | DE834102C (en) |
| DK (1) | DK79518C (en) |
| FR (1) | FR1031904A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE952808C (en) * | 1954-03-05 | 1956-11-22 | Hoffmann La Roche | Process for the production of a new tropasaeuramide |
| DE960634C (en) * | 1952-10-24 | 1957-03-28 | Hoffmann La Roche | Process for the preparation of substituted tropic acid-N- (ª † -picolyl) -amides |
| DE961347C (en) * | 1952-02-06 | 1957-04-04 | Hoffmann La Roche | Process for the preparation of tropic acid-N- (‰ ‰ -picolyl) -amides which are further substituted on the amide nitrogen |
| DE965239C (en) * | 1954-04-24 | 1957-06-06 | Hoffmann La Roche | Process for the preparation of tropic acid-N-alkyl-N- (ª † -picolyl) -amides |
| DE1058512B (en) * | 1954-09-24 | 1959-06-04 | Hoffmann La Roche | Process for the preparation of methyl-(ª-picolyl)-amine |
| DE1142614B (en) * | 1957-05-31 | 1963-01-24 | Koninklijke Pharma Fab Nv | Process for the production of benzhydryl ethers of tropine, their salts and quaternary ammonium compounds |
| US7645791B2 (en) * | 2003-11-25 | 2010-01-12 | High Point Pharmaceuticals, Llc | Salicylic anilides |
-
1950
- 1950-04-25 CH CH281901D patent/CH281901A/en unknown
- 1950-12-29 DE DEH7112A patent/DE834102C/en not_active Expired
-
1951
- 1951-01-03 AT AT170881D patent/AT170881B/en active
- 1951-01-03 DK DK1651A patent/DK79518C/en active
- 1951-01-31 FR FR1031904D patent/FR1031904A/en not_active Expired
-
1952
- 1952-02-06 CH CH307541D patent/CH307541A/en unknown
- 1952-12-16 AT AT178354D patent/AT178354B/en active
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE961347C (en) * | 1952-02-06 | 1957-04-04 | Hoffmann La Roche | Process for the preparation of tropic acid-N- (‰ ‰ -picolyl) -amides which are further substituted on the amide nitrogen |
| DE960634C (en) * | 1952-10-24 | 1957-03-28 | Hoffmann La Roche | Process for the preparation of substituted tropic acid-N- (ª † -picolyl) -amides |
| DE952808C (en) * | 1954-03-05 | 1956-11-22 | Hoffmann La Roche | Process for the production of a new tropasaeuramide |
| DE965239C (en) * | 1954-04-24 | 1957-06-06 | Hoffmann La Roche | Process for the preparation of tropic acid-N-alkyl-N- (ª † -picolyl) -amides |
| DE1058512B (en) * | 1954-09-24 | 1959-06-04 | Hoffmann La Roche | Process for the preparation of methyl-(ª-picolyl)-amine |
| DE1142614B (en) * | 1957-05-31 | 1963-01-24 | Koninklijke Pharma Fab Nv | Process for the production of benzhydryl ethers of tropine, their salts and quaternary ammonium compounds |
| US7645791B2 (en) * | 2003-11-25 | 2010-01-12 | High Point Pharmaceuticals, Llc | Salicylic anilides |
Also Published As
| Publication number | Publication date |
|---|---|
| CH281901A (en) | 1952-03-31 |
| AT178354B (en) | 1954-05-10 |
| CH307541A (en) | 1955-05-31 |
| AT170881B (en) | 1952-04-10 |
| DK79518C (en) | 1955-07-11 |
| FR1031904A (en) | 1953-06-29 |
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