Drug – bio-affecting and body treating compositions – Designated organic active ingredient containing – Having -c- – wherein x is chalcogen – bonded directly to...
Patent
1993-10-01
1995-07-11
Dentz, Bernard
Drug, bio-affecting and body treating compositions
Designated organic active ingredient containing
Having -c-, wherein x is chalcogen, bonded directly to...
514454, 514510, 514567, 549354, A61K 31335, C07D31312
Patent
active
054321921
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/JP92/00365 filed Mar. 26, 1992.
TECHNICAL FIELD
The present invention relates to novel tricyclic compounds which are useful as anti-histaminic agents and anti-allergic agents. The present invention also relates to processes for preparing said compounds and uses thereof.
BACKGROUND ART
As examples of therapeutic compounds having a tricyclic nucleus structurally similar to the compound of the present invention, Cyclobenzaprine (The Merck Index, 11th edition, 2719) useful as a muscle relax ant represented by the following formula (II): ##STR2## and Doxepin (The Merck Index, 11th edition, 3425) useful as an antidepressant and an antipruritic agent represented by the following formula (III): ##STR3## are known.
However, Cyclobenzaprine is known to cause adverse reactions such as sleepiness, dizziness, fatigue, thirst, nausea, constipation, and dyspepsia. Doxepin also induces adverse reactions such as sleepiness, thirst, and constipations. These adverse reactions are caused because Cyclobenzaprine or Doxepin have various pharmacological activities such as an activity on central nervous system and an anti-acetylcholinergic activity in addition to their principal activities, i.e., muscle relaxing, anti-depressing activities and anti-histaminic activities.
Accordingly, an object of the present invention is to provide a medicament having an excellent selectivity of increased desired principal activities and reduced side effects by separating various pharmacological activities induced by medicaments such as Cyclobenzaprine and Doxepin.
The inventors of the present invention conducted various studies to achieve the foregoing object and found that the object can be achieved by providing novel tricyclic compounds of the present invention. The inventors also found that the novel tricyclic compounds of the present invention have potent anti-histaminic and anti-allergic activities, and that they are useful as medicaments having excellent selectivities and reduced side effects caused by their anti-acetylcholinergic activity and the like. The present invention was achieved on the basis of these findings.
DISCLOSURE OF THE INVENTION
According to the present invention, novel tricyclic compounds and their pharmacologically acceptable salts are provided which are represented by the following formula (I): ##STR4## wherein X represents --CH.dbd.CH--, --CH.sub.2 O--, or --O--;
According to another embodiment of the present invention, there are provided a process for preparing said compounds, and an anti-histaminic agent and an anti-allergic agent comprising an effective amount of said compound.
BEST MODE FOR CARRYING OUT THE INVENTION
In the above-described formula (I) according to the present invention, the lower alkyl group represented by R.sup.1 and R.sup.2 may be, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, or tert-butyl.
Preferred compounds of the present invention include the following compounds: [N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]acetate; 3-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]propio nate; 4-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]butyra te; 5-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]valera te; 6-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]hexano ate; [N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]acetic a cid; 3-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]propio nic acid; 4-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]butyri c acid; 5-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]valeri c acid; 6-[N-[3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl]-N-methylamino]hexano ic acid; [N-[3-(dibenz[b,e]oxepin-11(6H)-ylidene)propyl]-N-methylamino]acetate; (E)-[N-[3-(dibenz[b,e]oxepin-11(6H)-ylidene)propyl]-N-methylamino]acetate; (Z)-[N-[3-(dibenz[b,e]oxepin-11(6H)-ylidene)propyl]-N-methylamino]acetate; 3-[N-[3-(dibenz[b,e]oxepin-11(6H)-ylidene
REFERENCES:
patent: 3991103 (1976-11-01), Barton et al.
patent: 4629691 (1986-02-01), Collins et al.
patent: 5332661 (1994-07-01), Adamczyk et al.
Hubbard et al., J. of Pharmaceut. Sciences, 67 (11), pp. 1571-1578 (1978).
Ito Yasuo
Kato Hideo
Koshinaka Eiichi
Morikawa Kouji
Ogawa Nobuo
Dentz Bernard
Hokuriku Seiyaku Co. Ltd.
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