Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-08-30
1995-01-10
Hollrah, Glennon H.
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514443, 514456, 514925, 514926, 514927, 514928, 549 23, 549 57, 549 58, 549396, 549404, 549471, 549 50, A61K 3138, A61K 3134, C07D33504, C07D33350
Patent
active
053807480
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to trialkylamine derivatives useful in the medical field, and more particularly, to trialkylamine derivatives capable of significantly ameliorating the digestive tract movement (gastrointestinal motility), intermediates for preparing the derivatives, and ameliorants for gastrointestinal motility.
BACKGROUND ART
Hitherto, trimebutine maleate has been primarily used as an ameliorant for gastrointestinal motility.
The trimebutine maleate has wide utility due to its two-face activities of promoting and suppressing the gastric movement. However, it is not necessarily satisfactory in that relatively large amounts, i.e., 300 mg per day of dose are required.
To avoid this disadvantage, studies have been conducted in search for ameliorants for gastrointestinal motility which can replace trimebutine maleate.
For example, (1-dimethylaminoindan-1-yl)methyl ester of substituted benzoic acid and (1-dimethylamino-1,2,3,4-tetrahydronaphthalen-1-yl)methyl ester of substituted benzoic acid are reported to have anticonvulsive activity, antiulcer activity and local anesthetic activity ("Scientia Pharmaceutica" vol. 56, pp. 243-250, 1988).
These, however, do not necessarily provide sufficient ameliorating activity on the gastrointestinal motility.
Accordingly, development of drugs which possess more stronger ameliorating activity on the gastrointestinal motility has still been desired.
The present inventors have carried out earnest studies under the mentioned circumstances, and have found that a specified trialkylamine derivatives exhibit excellent ameliorating activity on the gastrointestinal motility leading to completion of the invention.
DISCLOSURE OF THE INVENTION
According to the present invention, there is provided trialkylamine derivatives represented by the formula (1) or pharmaceutically acceptable salts thereof: ##STR2## wherein R.sup.1 and R.sup.2 may be the same or different from each other and each represents lower alkyl; and each represents hydrogen, lower alkyl, lower alkoxy, lower alkoxycarbonyl or halogen; represents hydrogen or lower alkyl; represents lower alkyl), >SO or >SO.sub.2 ; .about. (wherein p represents a number of 0 to 4 and symbol .about. represents the linkage with a benzene ring); and less, provided that the case where m is 0, n is 1 or 2, R.sup.1 and R.sup.2 represent each methyl, X represents --CH.dbd.CH--, Y represents --CH.sub.2 --, and Z represents --O--CO.about. is excluded.
The present invention also provides aminoalcohol derivatives represented by the formula (2) or salts thereof: ##STR3## wherein R.sup.1, R.sup.2, R.sup.6, R.sup.7, R.sup.8, X, Y, m and n have the same meaning as defined hereinbefore, provided that the case where X represents --CH.dbd.CH--,
The present invention further provides ameliorants for gastrointestinal motility containing, as their active ingredients, trialkylamine derivatives represented by the formula (1): ##STR4## wherein R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.7, R.sup.8, X Y, Z, m and n have the same meaning as defined hereinbefore or pharmaceutically acceptable salts thereof.
In the above formulae, the term "lower" means that the number of carbon atoms is 1 to 4, and the term "halogen" means fluorine, chlorine, bromine and iodine.
BEST MODE FOR CARRYING OUT THE INVENTION
The trialkylamine derivatives (1) according to the present invention can be prepared as follows:
First, aminoalcohol derivatives (2), which are the intermediates in the preparation of trialkylamine derivatives (1) of the present invention, are prepared, for example, by the following process. The reaction scheme is shown below: ##STR5## wherein R.sup.9 represents lower alkyl, X, Y, R.sup.1, R.sup.2, R.sup.6, R.sup.7, R.sup.8, m and n have the same meaning as defined hereinbefore.
In detail, the amino acid compound (5) is first esterified to obtain compound (6) by a conventional method, and the amino group of the compound (6) is dialkylated to obtain an ester (7), followed by reducing the ester (7) to produce
REFERENCES:
patent: 5030736 (1991-07-01), Press et al.
Aboul-Enein et al., Chemical Abstracts, vol. 110, No. 15, abstract No. 128064f, 1988.
Sarges et al., J. Med. Chem., vol. 16, No. 9, 1973.
Chaki Kyoji
Ichikawa Hiromi
Muto Yoshiaki
Ogura Kuniyoshi
Seiki Masao
Cebulak Mary C.
Hollrah Glennon H.
Zeria Pharmaceutical Co. Ltd.
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