IL35862A - Substituted n-(substituted aminoalkyl)-benzamidines and their preparation - Google Patents

Description

She present invention provides new H-(substituted aminoalkyl)-2-alkoxy-5-halo-benzamidines of the general formula in which R^ is an alkoxy radical of from 1 to 5 carbon atoms} ¾2 is a nitro or amino radical} A is an alkylene radical} R1 and Rw are the same or different alkyl radicals, or one of Rf and RM may be hydrogen, or R* and R" may be linked to each. other and- ogether with the nitrogen atom to which they are attached represent a saturated heterocyclic ring which /ma also contain, as a second hetero atom, oxygen or nitrogen, which latter bears hydrogen or a lower alkyl group; and X is a halogen atom} and their mono- and di-acid addition salts.

The new compounds of formula I above and their mono* and di-acid addition salts may be prepared by reacting an acid addition Salt of a benzimidic ester of the general formula in which R^, Rg, and X have the same meaning as above and ^ is an alkyl. radical of one to five carbon atoms, with a diamine of the general formula R» HJJ - A - (III) 2 ^R" in whic A, R* and Rw have the same meaning as in formula I above, compound of formula I thus obtained to the corresponding di-acid additio salt or to the free base of ormula I. The reaction of compound II with compound III may be carried out with or without a solvent; as a rule the use of a solvent, such as methanol or ©thanol, is preferred. The reaction is carried out at ambient temperature or with heating.

In order to convert the mono-acid addition salt of a compound of formula I into the corresponding di-acid addition salt, the former is dissolved in a solvent containing the desired acid, such as, for example, a hydrohalic acid, sulfuric acid, nitric acid, acetic acid, borontrifluoride, an aromatic sulfonic acid etc. , from which the di-acid addition salt is crystallized. The free base of formula I ma be obtained by dissolving the mono-salt in a alkaline solution» extracting the resulting free base with a solvent and evaporatin the solvent from the extract.

The starting materials of formula II in the above process are new compounds and their preparation is described in Patent Specification No-. 35861 The new compounds of this invention are useful as intermediates in the production of compounds possessing valuable pharmacological properties, i.e. , analgesic, antispasmodic, sedative, anesthetic and antiemetic activities, for example, N-(2-dialkylaminoalkyl)-2-alkoxy-4-amino-5~halobenzamide.

The invention is illustrated by the following Examples, to which it is not limited.

Example 1 N-(2-diethylaminoethyl)-2-methoxy-4-nitro-5-chloro-benzamidine dihydrochloride Example 4 When the procedure of Example 2 is followed, except that instead of the diethylaminoethyl amine 0.5 g of 2- morpholino-ethylamine is used, there is obtained N-morpholino- ethyl-2-methoxy-4-amino-5-chloro-benzamidine dihydrochloride. Example -, . "· .

:. : When the procedure of Example 2 is followed, except that5 instead of the diethylaminoethyl amine 0.5 g of 2- piperidino-ethylamine is used, there is obtained N-piperidino-• ethyl~2-methoxy-4-amino-5-chloro-benzamidine dihydrochloride . Example 6 - ■ --- : • : "/ " Y. When the procedure of Example 2 is followed, except that instead of the diethylaminoethyl amine 0.5 g of 2-(4-methyl' piperaziho)-ethylamine is used, there is obtained ii-(4-methyl- piperazino-l-ethyl)-2-methoxy-4-amino-5-chloro-benzamidine dihydrochloride .

Claims (1)

1. Compound of the general in which is an alkoxy radical of 1 to carbon is a nitro or amino A is an alkylene and are the same or different alkyl or one of and ma be or and may be linked to each other and together with the nitrogen atom to which they are attached represent a saturated heterocyclic ring which may also as a second hetero oxygen or which latter bears or a lower alkyl X is a halogen and their and addition A process for the preparation of compounds of formula I in Claim and their and addition wherein a compound of the general formul which and X have the same meaning as in Claim 1 and is ah alkyl radical of to 5 carbon is reacted with diamine of general formula A in which and Rw the same meaning as in I in 1 if the addition salt of the compound of formula I thus is converted to the corresponding addition salt or to the free of formula For the Applicants PARTNERS A insufficientOCRQuality