Organic compounds -- part of the class 532-570 series – Organic compounds – Four or more ring nitrogens in the bicyclo ring system
Patent
1991-03-08
1992-12-29
Ivy, C. Warren
Organic compounds -- part of the class 532-570 series
Organic compounds
Four or more ring nitrogens in the bicyclo ring system
544375, 546196, 548525, 549354, C07D41312
Patent
active
051752867
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
The present invention relates to a novel dibenz[b,e] oxepin derivative which is a non-steroid type antiphlogistic agent having anti-inflammatory, analgesic actions, extremely slight gastroenteric troubles and particularly high safety.
2. Background Art
Compounds having a dibenz[b,e]oxepin nucleus to the 2-position or 3-position of which is attached an alkanic acid such as acetic acid or propionic acid, have been reported in Japanese Pat. Appln. Laid-Open Gazettes Nos. 50-35179 and 50-58084, Japanese Pat. Gazette No. 55-32708, "Journal of Medicinal Chem., Vol. 19, No. 7, pp. 941-946 (1976)", and "Arch. int. Pharmacodyn, 227, pp. 142-154 (1977). Some of these publications indicate that said compounds have anti inflammatory, analgesic actions. The above publications neither disclose nor even suggest anything about dibenz[b,e] oxepin derivatives not only having an alkanic acid such as acetic or propionic acid at one of the 2-position and 3 position thereof but also having a lower alkoxy group at the other as in the compounds of the present invention.
Conventional non-steroid type acidic antiphlogistics typified by indomethacin, aspirin and the like, as compared with basic antiphlogistics, will exhibit clear pharmacological actions whereas they will have unfavorable side effects on digestive tracts such as stomachs and intestines when administered to life. Gastric ulcers and duodenal ulcers will frequently occur as said side effects whereby said conventional acidic antiphlogistics are limited in use as a medicine.
Thus, in an attempt to provide compounds which have solved the above problems, many compounds have been synthenized. The compounds so synthesized, however, are not appreciated to be satisfactory ones. For example, the compounds described in said Japanese Pat. Appln. Laid-Open Gazette No. 50-35179 and "Journal of Medicinal Chem., vol. 19, No. 7, pp.941-946 (1976)" are now devalued as a medicine since they tend to cause gastroenteric tract troubles as in the above-mentioned antiphlogistics.
The primary object of the present invention is to provide novel compounds which, when administered, will not only exhibit excellent analgesic and anti-inflammatory effects but also have remarkably low side effects (the side effects being such as gastroenteric tract troubles) and toxicity with high safety, as compared with conventional anti-inflammatory, analgesic agents.
SUMMARY OF THE INVENTION
The present inventors made various intensive studies in view of the above problems and, as the result of their studies, found that said problems are solved by the following compounds. The present invention is based on this finding or discovery.
The compounds of the present invention are dibenz[b,e]oxepin derivatives represented by the following formula (I) ##STR3## wherein R.sup.1 and R.sup.2 are each a hydrogen atom, halogen atom, lower alkyl group or lower alkoxy group; one of R.sup.3 and R.sup.4 is a lower alkoxy group, and the other is a group represented by the following formula (II) ##STR4## wherein R.sup.5 is a hydrogen atom or lower alkyl group, A is a hydroxyl group, --O(CH.sub.2).sub.m --R.sup.6 (wherein m is an integer of 1-6, H.sup.6 is a hydrogen atom, lower alkyl group, lower alkoxy group, piperazino, morpholino, piperidino group, pyrrolidino group or lower alkoxycarbonyl group, di-lower alkylamino group or --NH(CH.sub.2).sub.n-- R.sup.7 (wherein n is an integer of 1-3, R.sup.7 is a hydrogen atom, hydroxyl group, phenyl group, thiazole group or piperazino, morpholino, piperidino or pyrrolidino group.
The compounds of the present invention will be explained in further detail hereunder.
Firstly, the substituents in the formula (I) will be further detailed below.
The R.sup.1 and R.sup.2 in the formula (I) are each a hydrogen atom; a halogen atom such as fluorine, chlorine, bromine or iodine; a lower alkyl group such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl or tert.-butyl; or a lower alkoxy group such as methoxy, ethoxy, n propoxy, iso-propoxy, n-butoxy, iso-butoxy
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Deguchi Yoshiki
Hachiya Terumi
Hamanaka Shoji
Inoue Hisataka
Nakashima Mikio
Covington Raymond
Hisamitsu Pharmaceutical Co. Inc.
Ivy C. Warren
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