Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1998-08-31
2000-05-16
Kight, John
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
549467, 546196, 548525, 548950, A61K 31343, C07D30779
Patent
active
060638109
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/FR97/00383 filed Mar. 5, 1997, now WO97/32870 Sep. 12, 1997.
The subject-matter of the present invention is (2-aminoethyl)benzofuran derivatives, the preparation thereof and the therapeutical use thereof.
Patent Application WO 94 20472 discloses synthetic intermediates: 2-(benzofuran-7-yl)ethyl-N-methylamine and 2- [[2-(2,3-dimethoxyphenyl)ethyl]methylamino]-1-(benzofuran-7-yl)ethanol. ##STR1## and in particular 1-(dibenzofuran-2-yl)-2-isopropylaminoethanol. Patent Application EP 306,226 discloses benzofurans of formula: ##STR2##
Patent Application EP 270,342 discloses benzofurans of formula: ##STR3## Finally, Patent Application EP 558,245 discloses a benzofuran compound: 7-{3-[4-(2-methoxyphenyl)-1-piperazinyl]propylcarbamoyl}-2-phenylbenzo[b]f uran.
The (2-aminoethyl)benzofuran derivatives of the present invention correspond to the following general formula (I) ##STR4## in which:
A represents either a hydrogen atom or a hydroxyl group,
B represents either a hydrogen atom or a C.sub.1-8 alkyl, C.sub.1-8 alkenyl, C.sub.1-8 fluoroalkyl or C.sub.1-8 perfluoroalkyl group,
R.sub.1, R.sub.2 and R.sub.5, which are identical or different, each represent a hydrogen atom, a halogen, such as a chlorine, a bromine or a fluorine, or a C.sub.1-8 alkyl, C.sub.1-8 alkenyl, C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkenyl, C.sub.6, C.sub.10 or C.sub.14 aryl, C.sub.1-6 alkoxycarbonyl, C.sub.1-6 hydroxyalkyl, C.sub.1-6 alkoxyalkyl, C.sub.1-6 alkoxy, C.sub.1-8 fluoroalkyl or C.sub.1-8 perfluoroalkyl group,
or R.sub.1 and R.sub.2 together form a C.sub.3-8 cycloalkyl, C.sub.3-8 cycloalkenyl or C.sub.6, C.sub.10 or C.sub.14 aryl ring, with the exclusion of the compounds in which R.sub.1 and R.sub.2 are simultaneously hydrogens and of 1-(dibenzofuran-2-yl)-2-isopropylaminoethanol,
R.sub.3 and R.sub.4, which are identical or different, represent either a hydrogen atom or a C.sub.1-8 alkyl, C.sub.1-8 alkenyl, C.sub.3-8 cycloalkyl or C.sub.3-8 cycloalkenyl group,
or R.sub.3 and R.sub.4 together form a C.sub.3-6 cycloalkyl or C.sub.3-6 cycloalkenyl ring, such as, for example, a piperidyl, azetidinyl or pyrrolidyl.
The preferred compounds according to the invention are those comprising radicals having the following meanings:
R.sub.1 and R.sub.2 each represent a C.sub.1 -C.sub.4 alkyl group, more preferably a methyl, ethyl or i-propyl group, or a CF.sub.3 group,
or R.sub.1 and R.sub.2 together form a C.sub.3 -C.sub.6 cycloalkyl group,
R.sub.3 and R.sub.4 each represent a C.sub.1 -C.sub.4 alkyl group, more preferably a methyl, ethyl or i-propyl group,
R.sub.5 represents a hydrogen atom,
A represents a hydroxyl group,
B represents a hydrogen atom.
The compounds of the invention can be used as medicaments, as contractile agents for smooth muscles and more particularly in the treatment of urinary incontinence, or as venoconstrictors and more particularly in the treatment of venous insufficiency or of venous ulcers.
Patent FR 1,532,210 discloses a very large family of heterocyclic compounds of formula W, ##STR5## in which A represents an optionally substituted pentagonal, hexagonal or heptagonal heterocyclic nucleus comprising one or more nitrogen, oxygen and/or sulphur atoms, only 22 compounds of which are specifically disclosed. None of these 22 compounds, which constitute the preferred compounds of this patent, comprises a benzofuran nucleus. These compounds are described as agents for blocking the beta-adrenergic effect and are used in the curative or prophylactic treatment of coronary diseases.
The compounds of general formula (I) comprise one or more asymmetric carbon atoms. They can therefore exist in the form of enantiomers or of diastereoisomers. These enantiomers, diastereoisomers and their mixtures, including racemic mixtures, form part of the invention.
The pharmaceutically acceptable salts of the compounds of formula (I) according to the invention can either be salts of inorganic acids, such as hydrochloric acid, hydrobromic acid, sulphuric acid or phosphoric acid, or salts of organic acids, such a
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Bovy Philippe
Courtemanche Gilles
Fett Eykmar
Galzin Anne Marie
O'Connor Stephen Eric
Aulakh Charanjit S.
Kight John
Synthelabo
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