DE1470111C3 - 5- square bracket to alpha-hydroxyalpha-phenyl-alpha- (2-pyridyl) -methyl square bracket to -7- (phenyl-2-pyridylmethylene) -5-norbornene-2,3-dicarbon- - Google Patents

Description

in which R is a 2-methoxyethyl group or a 3-dimethylaminopropyl group and its acid addition salts.

2. Process for the preparation of the compounds according to claim 1, characterized in that a-phenyl-a- [6 - phenyl - 6 - (2 - pyridyl) - 2 - fulvenyl] - 2 - pyridylmethanol with

a) maleic acid imide or a maleic acid imide which is N-substituted by the radical R of the formula I condensed according to Diels-Alder or

b) converts maleic anhydride into the corresponding dicarboxylic anhydride, this converted with ammonia or a corresponding amine into the acid amide and from it the dicarboximide forms with elimination of water and ring closure or

c) a corresponding amide of maleic acid is condensed and the norbornene-dicarboxylic acid monoamide obtained converted into the dicarboximide with elimination of water and ring closure or

d) an ester of maleic acid condensed and the ester thus obtained by reaction cyclized with ammonia or a corresponding amine to give the dicarboximide, in the compound obtained optionally introduces the radical R in the customary manner and that optionally converting the product obtained into an acid addition salt.

The invention relates to 5- [a-hydroxy-a-phenyl-a- (2 - pyridyl) - methyl] - 7 - (phenyl - 2 - pyridylmethylene) - - Norbornene - 2,3 - dicarboximides of the general formula I

phenyl - (2-pyridyl)

in which R is a 2-methoxyethyl group or a 3-dimethylaminopropyl group means their acid addition salts and process for their preparation. According to the process of the invention, the compounds are obtained by being known per se Way «- Phenyl -« - [6 - phenyl - 6 - (2 - pyridyl) - 2 - fulvenyl] -2-pyridylmethanol

a) with maleic acid imide or a maleic acid imide which is N-substituted by the radical R of the formula I condensed according to Diels-Alder or b). with maleic anhydride in the corresponding Dicarboxylic anhydride converts this with ammonia or a corresponding amine converted into the acid amide and the dicarboximide therefrom with elimination of water and ring closure forms or

c) condensed with a corresponding amide of maleic acid and the norbornene-dicarboxylic acid monoamide obtained converted into the dicarboximide with elimination of water and ring closure or

d) condensed with an ester of maleic acid and the ester thus obtained by reaction cyclized with ammonia or a corresponding amine to the dicarboximide, in the resultant The compound optionally introduces the radical R in a customary manner and the resulting If necessary, the product is converted into an acid addition salt.

The compounds according to the invention, especially in the form of their acid addition salts, absorb UV light and can be used as sunscreen substances in pastes and ointments. In addition, they can as a result their solubility in organic substances generally as UV absorbers in plastics and resins be used. For this purpose it is sufficient to incorporate 0.01 to 5% of the absorber, based on the polymer weight to provide protection against UV light, as in plastic films or Light filters, to ensure. The absorber can be in the mixture of the monomers before the polymerization to form the polymer, or it can be incorporated into the polymer during any stage of the treatment incorporated, such as by milling into the polymer or while the polymer is being spun into Fibers etc.

In addition, the compounds according to the invention have valuable pharmacological properties, for example an antiarrhythmic or rodenticidal activity. At doses from about 5 to about 20 mg / kg body weight intravenously they provide z. B. the earlier state in by Ouabain and Aconitine-induced arrhythmias. Another and very unusual property that the Compounds of the present invention have a high level of toxicity, which for certain Species is specific. In rats, the LD 50 value of 5- [a-hydroxy-a-phenyl-a- (2-pyridyl) -methyl] - 7 - (phenyl - 2 - pyridylmethylene) - 5 - norbornene-2,3 - dicarboxylic acid -N-OS- methoxyethyl) - imide 9 mg / kg body weight for oral use. In contrast, it is on the same application path at considerably higher doses, the same compound was relatively nontoxic in dogs and mice. the Compound does not cause deaths at doses of 1000 mg / kg body weight in many others Experimental animals as rats.

When used as rodenticides, the 2,3-dicarboximides are dissolved in water in the form of their acid addition salts. The connections are useful either as bases or as acid addition salts with a suitable bait, such as meat, meat extracts, Grain, mash, fruit, vegetables or other substances, together with a filler or Carriers such as starch, kaolin, montmorillonite clay, attapulgite clay, diatomaceous earth, cane sugar and the like Fabrics incorporated. The finished compositions can be in various forms, such as solutions, Suspensions, emulsions, pastes, powders, granules, tablets, beads or in other advantageous To form. The rodenticidally active compounds according to the invention are in the bait incorporated for the manufacture of a can composition which is related in terms of concentration on the active component is at least 0.001 percent by weight and generally from 0.001 to 10%, optimally from 0.01 to 1.0%.

The advantages of these compositions are obvious to the ^fanatic. The compositions or the active rodenticide can be exposed in whole or in part to other animals without endangering their lives. In contrast to known rodenticides, they can therefore be used freely and without precautionary measures in the vicinity of domestic animals and also of captured animals such as minks and rabbits. The toxicity of the compounds according to the invention to rats is shown in the following table:

R (see formula I)

LD ₃₀ values (oral)
in mg / kg

2-methoxyethyl **)
-CH ₂ CH ₂ OCH ₃

3-dimethylaminopropyl **)
- (CHa) ₃ N (CH ₃ ),

**) Endo isomers only.

9.0

> 30 <100

The preparation of the starting compound a-phenyl-α - [6 - phenyl - 6 - (2 - pyridyl) - 2 - fulvenyl] - 2 - pyridylmethanol takes place according to DT-PS 14 70 063.

The preparation of the compounds according to the invention is illustrated by the following examples explained:

Examples

1. It was a solution of 1.55 g (0.01 mol) of 2-methoxyethyl maleimide and 4.14 g (0.01 mol)

a - Phenyl - «- [6 - phenyl -« - (2 - pyridyl) - 2 - fulvenyl] -2-pyridyimethanol in 50 ml of benzene kept under reflux for 42 hours. The reaction mixture was evaporated to half of its original volume; Petroleum ether was added and obtained

ίο a white solid mass that was recrystallized twice from carbon tetrachloride petroleum ether and converted into white crystalline N- (2-methoxyethyl) -5 - [«- hydroxy -« - phenyl - a - (2 - pyridyl) - methyl] - 7 - [phenyl- (2 - pyridyl) - methylene] - 5 - norbornene - 2,3 - dicarboximide; Melting point 172 to 173 ⁰ C.

Analysis for C ₃₆ H ₃₁ N ₃ O ₄ :

Calculated ... C 75.90, H 5.49, N 7.38%;
found .... C 74.86, 75.06, H 5.48, 5.54,
N 7.23%.

2. 50 ml of anhydrous ethanol was added to 0.46 g of freshly cut sodium metal. After full Dissolution of the sodium was 5.11g

(0.01 mol) 5 - [«- Hydroxy -« - phenyl - «- (2 - pyridylmethyl)] - 7 - (phenyl - 2 - pyridylmethylene) - 5 - norbornene - 2,3 - dicarboximide added. After dissolution of the imide under heating were 1.58 g (0.01 mol) of S-chlorine-N.N-dimethylaminopropanhydro-

chloride was added and the reaction mixture was refluxed for 48 hours, at room temperature cooled and filtered off from undissolved solid components. The removal of the solvent in vacuo resulted in a crude product which is obtained as a light yellow amorphous mass. After two Precipitations from cyclohexane made the product further by extraction from ether in aqueous hydrochloric acid Purified (5%), the acidic layer washed with ether, basic with aqueous potassium carbonate

made and extracted back into ether. The combined essential extracts were dried over anhydrous magnesium sulfate and filtered off. The removal of the ether led to N- (3-dimethylaminopropyl) - 5 - [α - hydroxy - a - phenyl - α - (2 - pyridyl) -

methyl] - 7 - (phenyl - 2 - pyridylmethylene) - 5 - norbornene-2,3-dicarboximide as an amorphous solid; Melting point 68 to 86 ⁰ C.

The starting material was obtained according to DT-PS 14 70 063.

Claims (1)

Patent claims: 1. 5 - [«- Hydroxy - α - phenyl - α - (2 - pyridyl) methyl] - 7 - (phenyl - 2 - pyridylmethylene) - 5 - norbornene-2,3-dicarboximide of the general formula I. phenyl - (2-pyridyl)