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Details for Patent: 3,966,793

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Details for Patent: 3,966,793

Title: Intermediates for preparing 1,4-benzodiazepine-2-ones having a carboxylic acid ester or amide group in the 3-position
Abstract:Intermediates for preparing novel benzodiazepines having the formula ##SPC1## In which R.sub.1 is a hydrogen or halogen atom or a trifluoromethyl, loweralkyl, loweralkoxy, nitro or amino group; R.sub.2 is a furyl, a thienyl, cyclohexyl, a loweralkyl group or a phenyl group which may be substituted by a halogen atom or by a trifluoromethyl, nitro, loweralkoxy or loweralkyl group; and R.sub.3 is a hydrogen atom or a loweralkyl group; and R.sub.4 is lowercarbalkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-diloweralkylcarbamoyl, N-(diloweralkylaminoalkyl)carbamoyl, a group having the formula --COOCat in which Cat is a cation of an alkali metal or a semication of an alkaline earth metal or COOCat.CatOH, said intermediates being ortho-aminoaryl ketimines having the formula ##SPC2## Wherein R is hydrogen or ##EQU1## R.sub.1, R.sub.2, and R.sub.3 are as defined above, R.sub.4 is a hydrogen atom, a lowercarbalkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-diloweralkylcarbamoyl, N-(diloweralkylaminoalkyl)-carbamoyl, alkyl or substituted alkyl group; and R.sub.5 is a loweralkyl group.
Inventor(s): Schmitt, deceased; Josef (LATE OF L'Hay-les-Roses, FR)
Assignee: Clin Midy (Paris, FR)
Filing Date:Sep 26, 1973
Application Number:05/401,029
Claims:1. An ortho-aminoaryl ketimine having the formula ##SPC13##

in which R is a group having the formula ##EQU5## R.sub.1 is a hydrogen or halogen atom or a trifluoromethyl, loweralkyl, loweralkoxy, nitro or amino group, R.sub.2 is a cyclohexyl, a loweralkyl or a phenyl group, R.sub.3 is a hydrogen atom or a loweralkyl group, R.sub.4 is a hydrogen atom, lowercarbalkoxy, carbamoyl, N-loweralkylcarbamoyl, N,N-di-loweralkylcarbamoyl, N(di-loweralkylaminoalkyl) carbamoyl, loweralkyl group, and R.sub.5 is a loweralkyl group.

2. An ortho-amino-aryl-ketimine having the formula ##SPC14##

wherein R.sub.1 is a hydrogen or chlorine atom or a methyl, nitro or amino group; R.sub.2 is a phenyl, n-butyl or cyclohexyl group, R.sub.3 is a hydrogen atom or a lower alkyl group, R.sub.4 is a hydrogen atom or a carbamoyl, methyl-carbamoyl, dimethylcarbamoyl or lower carbalkoxy group and R.sub.5 is a lower alkyl group.

3. The compound of claim 2 wherein R.sub.1 is chlorine, R.sub.2 is phenyl, R.sub.3 is hydrogen, R.sub.4 is hydrogen and R.sub.5 is ethyl.

4. The compound of claim 2 wherein R.sub.1 is chlorine, R.sub.2 is phenyl, R.sub.3 is methyl, R.sub.4 is hydrogen and R.sub.5 is ethyl.

5. The compound of claim 2 wherein R.sub.1 is chlorine, R.sub.2 is phenyl, R.sub.3, is hydrogen, R.sub.4 is --COOC.sub.2 H.sub.5 and R.sub.5 is ethyl.

6. The compound of claim 2 wherein R.sub.1 is chlorine, R.sub.2 is phenyl, R.sub.3 is methyl, R.sub.4 is --COOC.sub.2 H.sub.5 and R.sub.5 is ethyl.

7. The compound of claim 2 wherein R.sub.1 is hydrogen, R.sub.2 is phenyl, R.sub.3 is hydrogen, R.sub.4 is hydrogen and R.sub.5 is ethyl.

8. The compound of claim 2 wherein R.sub.1 is hydrogen, R.sub.2 is phenyl, R.sub.3 is hydrogen, R.sub.4 is --COOC.sub.2 H.sub.5 and R.sub.5 is ethyl.

9. The compound of claim 2 wherein R.sub.1 is methyl, R.sub.2 is phenyl, R.sub.3 is hydrogen, R.sub.4 is hydrogen and R.sub.5 is ethyl.

10. The compound of claim 2 wherein R.sub.1 is chlorine, R.sub.2 is n-butyl, R.sub.3 is hydrogen, R.sub.4 is hydrogen and R.sub.5 is ethyl.

11. An ortho-aminoaryl ketimine according to claim 2 wherein R.sub.1 is hydrogen, chloro, or methyl, R.sub.2 is phenyl, R.sub.3 is hydrogen or methyl, R.sub.4 is hydrogen or COOC.sub.2 H.sub.5, and R.sub.5 is ethyl.

12. A process for producing an N-substituted ortho-aminoaryl ketimine having the formula ##SPC15##

in which R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are defined in claim 2 and R.sub.5 is a lower alkyl group which comprises reacting an imine having the formula ##SPC16##

in which R.sub.1, R.sub.2 and R.sub.3 are as above defined, with an aliphatic .alpha.-aminocarboxylic acid ester in the form of a base or a salt thereof, having the formula

in which R.sub.4 is as above defined, and R.sub.5 is a lower alkyl group in an inert organic solvent for the imine at a temperature between room temperature and the reflux temperature of the solvent until the said ortho-aminoaryl ketamine is formed.

13. A process according to claim 12 in which the .alpha.-aminocarboxylic acid ester is an alkyl .alpha.-aminomalonate or an alkyl .alpha.-aminoacetate.
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