SU400086A1 - In PTB FUND ShchiERT - Google Patents

Description

one

The invention relates to a process for the preparation of a novel benzenesulfonylurea of the formula

502-KNOSH1-K

x-co-NH-y where R is 4,7-eidomethylene perhydroiid-5-yl, 10 which in position 6 can be replaced by chlorine, Y 4,7-endomethylene hyperhydroiidan-2-yl,

yorkaran-7-yl.

-L o

bicyclo-5,1,0-octyl-8. : bicyclo- 6,1,0-nonyl-9, O bicycCl-4,2,0-octyl-7, taO 2,5-endocyclobutylene- (1,2) -cyclohexyl

2,6-endomethylencycloheptyl, 4,4-dimethyl-D2-cyclohexenyl, D2-cyclopentenyl, D2-cyclohepteiyl, D-cyclooctyl,

25

3

methylcyclopentyl,

3,3-dimethylcyclopentyl,

3-ethylcy.clopentyl,

3-tert-butylcyclopentyl,

2-chlorocyclopentyl,

L-cyclopentenylmethyl,

bicyclo- 2,1,1-gxyl- (2),

g

spiro- (2-cyclopropangentyl),

6

spiro- (2-cyclobutane),

spiro- (2-cyclopene ganpentyl),

6a

cyclopropyl, cyclobutyl, 5-methyl-D-cyclohexenyl, bicyclo-3,1,0-hexyl,

ABOUT

X (a) is phenyl, and all or each of the same or different substituents Z and Z;

Z - hydrogen, halogen, lower alkyl, alkoxy, alkenoxy, alkoxyalkoxy, fenalkr; lower acyl; beisoyl; trifluoromethyl; hydroxygrone;

Z is cyan, nitro, hydrogen; halogen, lower alkyl, alkoxy, alkoxyalkoxy or hydroxy;

X (b) -thiophene residue, which may be substituted once or twice with lower alkyl, alkoxy, alkoxyalkoxy, alkenoxy, phenylalkoxygrhena or halo;

YCHNg-CH2--; -CH-CH -, -;

I

sn,

-CH2-SP-

1n,

Under lower alkyl in this case should be understood alkyl with 1-4 carbon atoms in unbranched or branched tseni.

The resulting compounds have biologically active properties.

A known nanotool for benzenesulfonylurea is anilated with benzenesulfonyl urea, containing H1, e, and aminogram.

The predazeinin method is based on a known chemical reaction. However, using benzenesulfonylurea as the starting compound of the above formula makes it possible to obtain new compounds in which the presence of the substituents R, X and Y, which have the indicated meanings, eliminates the presence of unchanged biologically active properties.

The proposed removal is that the benzenesulfonylurea of formula

SO -NHCOtJH-R

NH - i / where R has the indicated value,

subjected to acylation with compounds containing the residue X-CO, where X has the indicated meaning, for example, with acid halides of suitably substituted cells. Moreover, the substituent can be introduced after or during the acylation.

As an example of carrying out the process of acceleration with the subsequent introduction of a substituent, it is possible to initiate a reaction between aminoalkylbenzene sulfonylurea and 2-methoxybenzoyl chloride and the subsequent introduction of a halogen atom into the benzene ring of benzamidogruium.

The process conditions depend on the starting materials.

The resulting compounds can be converted to their salts by npi treatment with an alkaline agent.

Example. (p-- 2-methoxy-5-chlorobenzamido-ethyl) -benzenesulfonyl-K1- (4,7-endomethylenernerhydroindan-5-yl) -urea.

8.2 g of (p-acetal1idostil) -benzenesulfonyl-N- (4.7-endomethyleneenerhydroindan-5il) -urea is heated in a solution of 1.6 g of sodium hydroxide in 30 ml of water for 2 hours under reflux. Then cooled to room temperature, treated with acetone.

and 1.3 g of glacial acetic acid and norses added 4.1 g of 2-methoxy-5-chlorobenzoyl chloride. The reaction mixture is stirred for 2 hours, the precipitate is filtered and treated with sodium bicarbonate solution.

and then do not precipitate from dilute ammonia with hydrochloric acid. The resulting (| 3-- 2-methoxy-5-chlorobenzamido) -ethyl) -benzenesulfonyl-N- (4.7-endomethylene-hyper-indan-5-yl) -urea has a mp. 196-

198 ° C (from methanol - dimethylformamide).