Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1997-10-31
1999-02-09
Higel, Floyd D.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514419, 548453, 548500, A61K 31415, C07D49504
Patent
active
058695184
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR96/00555, filed Apr. 12, 1996.
The subject of the present invention is azacyloalkane derivatives, their preparation and their applications in therapy, especially in the treatment of diabetes, of obesity and of hyperglycaemia.
The azacyloalkane derivatives of the invention correspond to the general formula (I) ##STR2## in which: * R.sub.1 and R.sub.2, which are identical or different, each represent a hydrogen atom, a linear, branched or cyclic alkyl group comprising from 1 to 6 carbon atoms, or a phyenyl group optionally substituted with a linear or branched alkyl group comprising from 1 to 6 carbon atoms, with one or two halogen atoms or with a group COOR.sub.6, R.sub.6 being a hydrogen atom or a linear or branched alkyl group comprising from 1 to 6 carbon atoms, or R.sub.1 and R.sub.2 together form an oxo group, comprising from 1 to 4 carbon atoms, or alternatively R.sub.3 forms a methylene group, pyridyl group, optionally substituted with a linear or branched alkyl group comprising from 1 to 6 carbon atoms, with one or two halogen atoms, with a nitro group, or with a group COOR.sub.6, R.sub.6 being as defined above, phenylene group in which one carbon atom is linked to Y and another carbon atom, adjacent to the preceding one, is linked to the said methylene group, benzyl group, or an N.sup.4 -methylpiperazinyl, or alternatively a group NHR.sub.8 where R.sub.8 is a hydroxyl, pyridylmethyl or phenylmethyl group, atoms, one or two linear or branched alkyl groups comprising from 1 to 4 carbon atoms, with a nitro group, with a group COOR.sub.6, R.sub.6 being as defined above, with one or two linear or branched alkoxy groups comprising from 1 to 6 carbon atoms or with a methylenedioxy group,
The compounds of formula (I) form, with pharmaceutically acceptable acids and bases, salts which are part of the invention. According to the present invention, the preferred salts are the sodium and calcium salts, which are such that R.sub.7 represents a sodium or calcium atom.
The compounds of formula (I) comprise an asymmetric carbon atom. They can therefore exist in the form of enantiomers. These enantiomers, as well as mixtures thereof, including the racemic mixtures, are part of the invention.
Within the framework of the present invention, the terms below have the following meanings: carbon atoms, as well as, optionally, a heteroatom chosen from the group consisting of sulphur, oxygen and nitrogen, the said ring having a maximum number of unsaturations, taking into account optional substituents thereof.
Moreover, it may be noted that when n is equal to 1 or 2, this means that the number of carbon atoms included in the brackets is equal to 1 or 2. When n is equal to 1, the azacycloalkane derivative according to the invention is a dihydro-1H-pyrrole derivative. When n is equal to 2, the azacycloalkane derivative according to the invention is a tetrahydropyridine derivative.
According to a preferred embodiment of the invention, A is chosen from the group consisting of thiophene, benzene, furan and naphthalene, these aromatic groups being substituted or unsubstituted as indicated above. According to another advantageous feature of the invention, n is equal to 1 or R.sub.5 is a hydroxyl group. Moreover, r.sub.4 is preferably an unsubstituted phenyl group. As subgroup of compounds according to the invention, there may be mentioned especially that consisting of the derivatives of utanoic acid of formula II ##STR3## in which R.sub.5 is as defined for the formula (I) and R.sub.9 and R.sub.10, which are identical or different, represent a hydrogen atom, a halogen atom or a linear or branched alkyl group comprising from 1 to 4 carbon atoms. The pure enantiomers, the mixtures of enantiomers, including the racemic mixtures, as well as the pharmaceutically acceptable salts of the compounds of formula (II), are part of the invention.
The compounds of formula (I) can be prepared according to the process represented in Scheme 1 of Annex 1. According to this process, a compound of formula (III) ##STR
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Bedoya Zurita Manuel
Del Sol Moreno Gregorio
Diaz Martin Juan Antonio
Jimenez Bargueno Maria Dolores
Martin Escudero Perez Ulpiano
Higel Floyd D.
Synthelabo
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