Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-01-15
1994-08-09
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
546121, C07D47104, A61K 3144
Patent
active
053366794
DESCRIPTION:
BRIEF SUMMARY
FIELD OF THE INVENTION
This invention relates to tetrahydroimidazopyridine derivatives and salts thereof which are useful as medicines.
The compounds of this invention and salts thereof are considered to be useful for the prevention and treatment of the syndrome of hypersensitive intestinal diseases (irritable bowel syndrome) and the like.
BACKGROUND TECHNIQUES
As a result of intensive studies on the compounds having the antagonism against 5-HT.sub.3 receptor, tile present inventors discovered that the compounds represented by the above-mentioned general formula are novel compounds having a high degree of antagonism against 5-HT.sub.3 receptor, and accomplished this invention on the basis of these findings.
DISCLOSURE OF THE INVENTION
The term "lower" described in this specification means, unless otherwise specified, a linear or branched carbon chain having a carbon number of 1 to 6. Accordingly, as examples of the "lower alkyl group" may be mentioned methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tertbutyl, pentyl, isopentyl, hexyl, 1 -methylpentyl, 2-methylpentyl and 2-ethylbutyl groups. Of these, the groups having a carbon number of 1 to 3, such as methyl, ethyl and propyl groups are the most preferable.
In addition, some of the compounds of this invention can form salts, and this invention also includes the salts of the compounds represented by the above-mentioned general formula (I). As examples of these salts, may be mentioned salts with an inorganic base (such as sodium and potassium), salts with an organic base (such as ethylamine, propylamine, diethylamine, triethylamine, morpholine, piperidine, N-ethylpiperidine, diethanolamine and cyclohexylamine), salts with a basic amino acid (such as lysine and ornithine), ammonium salts, salts with a mineral acid (such as hydrochloric, sulfuric, phosphoric and hydrobromic acids), salts with an organic acid (such as acetic, oxalic, succinic, citric, maleic, malic, fumaric, tartaric and methanesulfonic acids), and salts with an acidic amino acid (such as glutamic and aspattic acids).
Furthermore, the compounds of this invention contain an asymmetric carbon atom in the molecule, and the compounds represented by the general formula (I) include all kinds of isomers based on this asymmetric atom, such as optically active compounds, rasemic compounds and diastereomers.
Preparative Methods
Described below are the typical preparative methods for the compounds of this invention. ##STR5##
The compounds of this invention represented by the general formula (Ia) or (Ib) can be obtained by the reaction of an aniline derivative represented by the general formula (II), or 2,3-dihydroindole represented by the formula (III), with a carboxylic acid represented by the general formula (Iv) or a reactive derivative thereof.
This reaction is an amide-forming reaction, and hence a variety of well-known methods may be applicable. There is no specific limitation upon the kind of solvent to be used, insofar as it is inert to the reaction. As Examples of the solvent to be used, may be mentioned dioxane, diethyl ether, tetrahydrofuran, chloroform, ethyl acetate and diemtylformamide, etc.
The compound (Iv) may be directly used for the reaction with the compound (II) or the compound (III), or may be used for that reaction in the form of a reactive, carboxy derivative in some cases.
When the compound (IV) itself is used for the reaction, any condensation agent commonly employed may be applicable (such as N,N-dicyclohexylcarbodiimide).
As examples of the reactive, carboxy derivative of compound (IV), may be mentioned acid halides, acid anhydride, acid azide, and various active esters employed for peptide synthesis.
The reaction should preferably be carried out in the presence of a base in some cases, depending on the type of the reactive derivative of compound (IV) used. As examples of the base used in this case, may be mentioned inorganic bases (such as sodium bicarbonate, potassium bicarbonate, sodium carbonate and potassium carbonate) and organic bases (such as triethylamine
REFERENCES:
patent: 4588732 (1986-05-01), Browne
Miyata Keiji
Ohmori Jun-ya
Ohta Mitsuaki
Suzuki Takeshi
Yanagisawa Isao
Dentz Bernard
Yamanouchi Pharmaceutical Co. Ltd.
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