CH397698A

CH397698A - Process for the production of new 1-carbamyl-indazoles

Info

Publication number: CH397698A
Application number: CH1042561A
Authority: CH
Inventors: Wagner-Jauregg Theodor Pr Chem; Demolis Andre Dr Chem; Guenther Dr Med Stille
Original assignee: Siegfried Ag
Priority date: 1961-09-08
Filing date: 1961-09-08
Publication date: 1965-08-31

Description

  

  
 



  Verfahren zur Herstellung neuer   1"Carbamylindazole   
Es wurde gefunden, dass man zu pharmazeutisch wertvollen Carbamyl-indazolen der allgemeinen For  mrl   
EMI1.1     
 kommt, in der R ein Halogenatom bedeutet, wenn R' Wasserstoff ist, und umgekehrt, wenn man die entsprechenden halogensubstituierten Indazole entweder mit Carbamylchlorid oder mit Phosgen umsetzt und im letzteren Falle das Zwischenprodukt mit Ammoniak zur Reaktion bringt.



   Unter den neuen Indazolen hat sich insbesondere das 3-Chlor-l-carbamyl-indazol pharmakologisch als wertvoll erwiesen. Es zeigt eine entspannende Wirkung und ruft eine Dämpfung der Schmerzempfindung hervor. In mancher Hinsicht weist es eine   Shn-    lichkeit mit den Barbituraten auf, ohne jedoch deren schlafinduzierende Wirkung zu zeigen. Darüberhinaus wirken diese Verbindungen, insbesondere die zuletzt genannte, auch antiphlogistisch und analgetisch.



   Beispiele
1. 12 g 3-Chlor-indazol werden in 200   cm3    Toluol suspendiert. Bei einer Temperatur zwischen -10 und   +250    leitet man Phosgen ein, bis die berechnete Menge davon aufgenommen worden ist. Man destilliert vom Lösungsmittel ab und erhält das entsprechende Chlorkohlensäurederivat (Smp.   90-95 ).    12 g dieser Verbindung werden im Anschluss daran in 340/oigem wässerigem Ammoniak suspendiert und unter Rühren auf etwa 450 erwärmt. Man destilliert das Wasser ab und erhält das   3-Chlor-1-carbamyl-    indazol, welches nach dem Umkristallisieren aus 960/oigem Alkohol zwischen 172 und 1740 schmilzt.



   Berechnet:   Cd 18,16   
Gefunden:   C1      18,30.   



   2. Arbeitet man wie oben, ersetzt aber das 3 Chlorindazol durch das 6-Chlorindazol, so erhält man das   6-Chlor-1-carbamyl-indazol,    das aus Dioxan umkristallisiert bei   223-226       schmilzt.   



   Berechnet:   C1    18,15
Gefunden:   C1      18,20.     



   PATENTANSPRUCH
Verfahren zur Herstellung von neuen l-Carbamyl-indazolen der Formel
EMI1.2     
 in der R ein Halogenatom bedeutet, wenn R' Wasserstoff ist, und umgekehrt, dadurch gekennzeichnet, dass man die entsprechenden halogensubstituierten Indazole entweder mit Carbamylchlorid oder mit Phosgen umsetzt und im letzteren Fall das Zwischenprodukt mit Ammoniak zur Reaktion bringt. 

**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.



   



  
 



  Process for the preparation of new 1 "carbamylindazoles
It has been found that pharmaceutically useful carbamyl indazoles of the general formula mrl
EMI1.1
 comes, in which R denotes a halogen atom when R 'is hydrogen, and vice versa, if the corresponding halogen-substituted indazoles are reacted either with carbamyl chloride or with phosgene and in the latter case the intermediate is reacted with ammonia.



   Among the new indazoles, 3-chloro-1-carbamyl-indazole in particular has proven to be pharmacologically valuable. It has a relaxing effect and dampens the sensation of pain. In some respects it is similar to barbiturates, but without showing their sleep-inducing effect. In addition, these compounds, especially the last-mentioned, also have an anti-inflammatory and analgesic effect.



   Examples
1. 12 g of 3-chloro-indazole are suspended in 200 cm3 of toluene. Phosgene is introduced at a temperature between -10 and +250 until the calculated amount has been absorbed. The solvent is distilled off and the corresponding chlorocarbonic acid derivative (melting point 90-95) is obtained. 12 g of this compound are then suspended in 340% aqueous ammonia and heated to about 450 with stirring. The water is distilled off and the 3-chloro-1-carbamylindazole is obtained, which melts between 172 and 1740 after recrystallization from 960% alcohol.



   Calculated: Cd 18.16
Found: C1 18.30.



   2. If you work as above, but replace the 3-chloroindazole with the 6-chloroindazole, you get 6-chloro-1-carbamyl-indazole, which, recrystallized from dioxane, melts at 223-226.



   Calculated: C1 18.15
Found: C1 18.20.



   PATENT CLAIM
Process for the preparation of new l-carbamyl-indazoles of the formula
EMI1.2
 in which R denotes a halogen atom when R 'is hydrogen, and vice versa, characterized in that the corresponding halogen-substituted indazoles are reacted either with carbamyl chloride or with phosgene and in the latter case the intermediate is reacted with ammonia.

** WARNING ** End of DESC field could overlap beginning of CLMS **.

Claims

** WARNING ** Beginning of CLMS field could overlap end of DESC **.

Process for the preparation of new 1 "carbamylindazoles It has been found that pharmaceutically useful carbamyl indazoles of the general formula mrl EMI1.1 comes, in which R denotes a halogen atom when R 'is hydrogen, and vice versa, if the corresponding halogen-substituted indazoles are reacted either with carbamyl chloride or with phosgene and in the latter case the intermediate is reacted with ammonia.

Among the new indazoles, 3-chloro-1-carbamyl-indazole in particular has proven to be pharmacologically valuable. It has a relaxing effect and dampens the sensation of pain. In some respects it is similar to barbiturates, but without showing their sleep-inducing effect. In addition, these compounds, especially the last-mentioned, also have an anti-inflammatory and analgesic effect.

Examples 1. 12 g of 3-chloro-indazole are suspended in 200 cm3 of toluene. Phosgene is introduced at a temperature between -10 and +250 until the calculated amount has been absorbed. The solvent is distilled off and the corresponding chlorocarbonic acid derivative (melting point 90-95) is obtained. 12 g of this compound are then suspended in 340% aqueous ammonia and heated to about 450 with stirring. The water is distilled off and the 3-chloro-1-carbamylindazole is obtained, which melts between 172 and 1740 after recrystallization from 960% alcohol.

Calculated: Cd 18.16 Found: C1 18.30.

2. If you work as above, but replace the 3-chloroindazole with the 6-chloroindazole, you get 6-chloro-1-carbamyl-indazole, which, recrystallized from dioxane, melts at 223-226.

Calculated: C1 18.15 Found: C1 18.20.

PATENT CLAIM Process for the preparation of new l-carbamyl-indazoles of the formula EMI1.2 in which R denotes a halogen atom when R 'is hydrogen, and vice versa, characterized in that the corresponding halogen-substituted indazoles are reacted either with carbamyl chloride or with phosgene and in the latter case the intermediate is reacted with ammonia.