AT367394B - METHOD FOR PRODUCING NEW INDANDERIVATES - Google Patents

Description

  

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   The invention relates to a process for the preparation of new indane derivatives of the general formula
 EMI1.1
 wherein R t stands for hydrogen or an alkyl group with 1 to 10 carbon atoms, R2 for chlorine or an alkoxy group with 1 to 4 carbon atoms or RI and R2 together for a residue - (CH) -, m for 3 or 4, and their salts with Acids.



   In the compounds of formula (I), Ri preferably contains 1 to 5, in particular 2 or 3, carbon atoms as the alkyl group.



   In the group - (CH) - m preferably has the value 3.



   According to the invention, the compounds of the formula (I) and their salts are obtained by using compounds of the formula
 EMI1.2
 wherein RI and R2 are as defined above and R3 is an alkyl group having 1 to 4 carbon atoms or a phenyl radical optionally substituted by chlorine, bromine, alkyl or alkoxy having 1 to 4 carbon atoms, hydrolyzed and, if desired, the acids obtained are converted into their salts.



   The hydrolysis of the compounds of the formula (II) can be carried out by methods which are known per se for the hydrolysis of carboxylic acid esters. The reactions are preferably carried out in the presence
 EMI1.3
 or their salts with bases. The free acids can be converted into their salts with bases in a manner known per se and vice versa. Examples of salts with inorganic bases include alkali metal - such as sodium or potassium salts or alkaline earth metal - such as calcium or magnesium salts. Organic bases suitable for salt formation are, for example, amines.



   The starting compounds of the formula (II) can be obtained, for example, by a) a compound of the formula
 EMI1.4
 

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 where RI and R2 have the above meaning, nitrided, e.g. B. in an HSO-HNO, mixture, b) then the compound of the formula obtained
 EMI2.1
 where RI and R2 have the above meaning reduced, e.g.

   B. by catalytic hydrogenation or with iron in aqueous acid, and c) a compound of the formula obtained
 EMI2.2
 in which R 1 and Ru have the above meaning, with a compound of the formula R-CO-COOR ,, (VI) in which R has the above meaning and R is chlorine, bromine, an alkoxy group having 1 to 4 carbon atoms or an optionally by chlorine, Bromine, alkyl or alkoxy with 1 to 4 carbon atoms substituted phenoxy means.



   This reaction can be carried out according to conventional methods for the formation of carbonamides.



  For example, the reaction is carried out in an inert solvent, such as in a hydrocarbon, chlorinated hydrocarbon, ether or tertiary amine, or in an excess of the compound of the formula (VI) at temperatures between -5 to 2000.degree. If desired, a basic catalyst, e.g. B. a tertiary amine such as pyridine or triethylamine may be added.



   R preferably has the same meaning as R, 0 or represents chlorine or bromine.



   The compounds of formula (I) obtained can be isolated and purified by methods known per se.



   If the preparation of the starting compounds is not described, they are known or can be prepared by processes known per se.



   The compounds of the formula (I) and their physiologically tolerable salts are distinguished by interesting pharmacological properties and can therefore be used as medicaments. In particular, the compounds show a disodium chromoglycate (DSCG) -like effect.



  Due to this DSCG-like effect, the compounds can be used for the prophylaxis and therapy of allergic and exertion-related asthma and allergic gastrointestinal disorders as well as for the prophylaxis of allergic affections.



   In the following examples, all temperatures are given in degrees Celsius.



   Example 1: N- (2, 6, 7, 8, 9. 9a-Hexahydro-2-oxo-1H-benz [c, d] azulen-3-yl) oxamic acid
A solution of 4 g of N- (2, 6, 7, 8, 9, 9a-hexahydro-2-oxo-1H-benz [c, d] azulen-3-yl) oxamic acid ethyl ester in 150 ml of methanol is added Solution of 0.95 g of potassium hydroxide in 2 ml of water was added and the mixture was refluxed for 1 h. The solution is concentrated, diluted with water and neutral by-products extracted with dichloromethane. The aqueous part is acidified with hydrochloric acid and the N- (2,6,7,8,9,9a-hexahydro-2-oxo-1H-benz [c, d] azulen-3-yl) oxamic acid is filtered off.



   Mp .: 191 to 1920.

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 EMI3.1
 
 EMI3.2
 
<tb>
<tb> N- <SEP> (2, <SEP> 6, <SEP> 7, <SEP> 8, <SEP> 9, <SEP> 9a-hexahydro-2-oxo-lH-benz <SEP> [c , <SEP> d] <SEP> azulen-3-yl) -example <SEP> No. <SEP> RI <SEP> R <SEP> Fp. <SEP>: <SEP>
<tb> 2- <SEP> (CH2) <SEP> 3- <SEP> 208-2100 <SEP>
<tb> 3 <SEP> H <SEP> OCHs <SEP> 221-2230 <SEP>
<tb> 4 <SEP> n-C3H7 <SEP> Cl
<tb>


 

Claims (1)

  PATENT CLAIM: Process for the preparation of new indane derivatives of the formula  EMI3.3  in which Ri represents hydrogen or an alkyl group having 1 to 10 carbon atoms, R2 represents chlorine or an alkoxy group having 1 to 4 carbon atoms or RI and R2 together represent a radical - (CH.) -, m represents 3 or 4, and their salts, characterized in that compounds of the formula  <Desc / Clms Page number 4>    EMI4.1  wherein R, and R2 are as defined above and R, an alkyl group having 1 to 4 carbon atoms or a phenyl radical optionally substituted by chlorine, bromine, alkyl or alkoxy having 1 to 4 carbon atoms, hydrolyzed and the acids of the formula (I) obtained, if desired, in transferred their salts.