Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Patent
1996-04-05
1997-12-23
Shah, Mukund J.
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
548576, 558482, 558483, C07D20904
Patent
active
057009473
DESCRIPTION:
BRIEF SUMMARY
OBJECT OF THE INVENTION
This application is a 371 of PCT/EP94/03182 dated Sep. 23, 1994.
The present invention refers to nitric esters of derivatives of propionic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl -3-indolylacetic acid, 6-methoxy-2-naphthylacetic acid, their pharmaceutical utilization and the process for their preparation. The present invention also refers to pharmaceutical compositions comprising at least one of said nitric esters as active constituent.
PRIOR ART
Some derivatives of propionic acid, such as, for instance, 2-(6-methoxy-2-naphtyl)propionic acid 2-(4-isobutylphenyl) propionic acid used for a long time in the pharmaceutical field for their anti-inflammatory activity and have been present for many years on the different world markets. The process for the preparation of 2-(6-methoxy-2-naphtyl)propionic acid has been described in the South African Patent No. 6707,597, in the German Patent No 1,934,460, corresponding to the U.S. Pat. No. 3,637,767 and also in C.A. 71, 91162j (1969); HARRISON et al. J. Med. Chem. 13,203 (1970); the process for the preparation of 2-(4-isobutylphenyl) propionic acid has been described in Patents GB No 971,700, U.S. Pat. No. 3,228,831 and U.S. Pat. No. 3,385,886, and also in T. SHIORI, N. KAWAI, J. Org. Chem. 43,2936 (1978); J. T. PINHEY, B. A. ROWE, Tetrahedron Letters 21, 965 (1980) while the process for the preparation of described in the German Patent No. 2,814,556 and in U.S. Pat. No. 4,161,538.
In the case of 2-(6-methoxy-2-naphtyl)propionic acid, the pharmacological profile is described in ROSZKOWSKI et el. J. Pharmacol. Exp. Ther. 179,114 (1971), while the pharmacological profile of 2-(4-isobutylphenyl)propionic acid is reported in ADAMS et al. Arch. Pharmacodyn. Ther. 178,115 (1969).
The utilization of these derivatives of propionic acid as anti-inflammatory agents involves, as known, extremely severe adverse reactions affecting, for instance, the gastrointestinal system, as well as damages to liver and kidneys.
Other particularly toxic products are, for example, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid or particular, in some countries Ketorolac has been withdrawn from the market because of its gastrointestinal toxicity, while Indomethacin is one of the drugs which has caused the highest death-rate from the year of its introduction in the market. Compared with other known anti-inflammatory and/or analgesic drugs, Ketorolac and Indomethacin cause--because of the already described adverse reactions--very extensive damages and, in particular as concerns gastrointestinal toxicity, deaths have been ascertained even in children.
It is therefore evident that there is the need of having drugs which, though providing a good anti-inflammatory and/or analgesic activity, do not result to be, in general, toxic.
OBJECTS OF THE INVENTION
Object of the present invention is that of providing a product which, while assuring at least the maintenance of the pharmacological activity which is characteristic of the known anti-inflammatory and/or analgesic agents, is capable of eliminating the adverse reactions brought about by the treatment with said agents, and has good tolerance.
Another object of the present invention is that of realizing a process for the preparation of derivatives of propionic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl-3-indolylacetic acid, 5-benzoyl 6-methoxy-2-naphthylacetic acid, having an anti-inflammatory and/or analgesic activity, good tolerance and being exempt from the adverse reactions that are typical of anti-inflammatory and analgesic agents.
Still another object of the present invention is that of providing pharmaceutical compositions having anti-inflammatory and/or analgesic activity which results provided with good tolerance.
DESCRIPTION OF THE INVENTION
These and still further objects and associated advantages which shall clearly result from the following description, are reached by derivatives of propionic acid, 1-(p-chlorobenzoyl)-5-methoxy-2-methyl -3-indolylacetic 6-methoxy-2-naphthylacetic acid w
REFERENCES:
patent: 3758544 (1973-09-01), Alvarez
patent: 5049694 (1991-09-01), Bron et al.
Bucknum Michael
Nicox S.A.
Shah Mukund J.
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