Diazacycloalkanealkylsulfonamide derivatives

Details Diazacycloalkanealkylsulfonamide derivatives Diazacycloalkanealkylsulfonamide derivatives

1995-11-20

1998-02-10

Bernhardt, Emily

Drug, bio-affecting and body treating compositions

Designated organic active ingredient containing

Heterocyclic carbon compounds containing a hetero ring...

514252, 514255, 540575, 544360, 544396, A61K 3155, A61K 31495, C07D29512, C07D40106

Patent

active

057169500

DESCRIPTION:

BRIEF SUMMARY
FIELD OF THE INVENTION

This invention relates to novel diazacycloalkanealkylsulfonamide derivatives having excellent antiallergic activity and thereby are useful as an medicament for preventing and treating diseases such as bronchial asthma, allergic rhinitis, atopic dermatitis, urticaria and the like, and pharmacologically acceptable salts thereof.


PRIOR ART

Presently, some kinds of antihistaminic agents or antiallergic agents having diazacycloalkane-skeletal structure have been found, for example, Chlorcyclizine (Merck Index, 11th edition, 2078)!, Among diazacycloalkanealkylsulfonic acids, it is known that some compounds have accelerating activity of erythrocyte transformation and antiplatelet However, for example, as shown in Experiments hereinafter, a compound of Reference Example 4 did not show an antiallergic activity. Some of Patent First Publication No. 153280/1987! and the compounds have calcium antagonistic activity and antiallergic activity. However, they have insufficient activity of suppressing passive cutaneous anaphylaxis (PCA).
Antiallergic agents have been used for treating diseases such as bronchial asthma, allergic dermal affection and allergic rhinitis. However, existing antiallergic agents, e.g. ketotifen, have some defects that drowsiness or sedation are caused by central nervous suppressing activity due to their strong antihistaminic side effects. With the object of removing these defects, various studies have been done until now, but no satisfactory result has been obtained.


DETAILED DESCRIPTION OF THE INVENTION

Under the circumstances, the present inventors have intensively studied, and as a resultant, have found that specific diazacycloalkanealkylsulfonamide derivatives have excellent antiallergic activity with low antihistaminic activity and low toxicity, and further they can readily be prepared.
The present invention provides diazacycloalkanealkylsulfonamide derivatives ##STR2## atom, hydroxy, trifluoromethyl, nitro or amino; R.sub.2 is phenyl which may optionally be substituted by 1 to 3 substituents on the phenyl ring selected from lower alkyl, lower alkoxy, halogen atom, hydroxy, trifluoromethyl, nitro and amino, or 2-pyridyl, 3-pyridyl or 4-pyridyl; a is 2 or 3; Y is alkylene; and R.sub.3 and R.sub.4 are the same or different and are each hydrogen atom, lower alkyl, lower hydroxyalkyl or cycloalkyl, or phenyl which may optionally be substituted by 1 to 3 substituents on the phenyl ring selected from lower alkyl, lower alkoxy, halogen atom, hydroxy, trifluoromethyl, nitro and amino! and pharmacologically acceptable salts thereof. alkyl containing 1 to 4 carbon atoms which include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Lower alkoxy expressed by R.sub.1 denotes alkoxy containing 1 to 4 carbon atoms which include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy and tert-butoxy. Halogen atoms expressed by R.sub.1 include chlorine, bromine, fluorine and iodine.
Lower alkoxy and halogen atoms as substituents on the phenyl ring in R.sub.2 include the same groups as defined in the above R.sub.1.
Alkylene expressed by Y denotes straight or branched chain alkylene containing 1 to 12 carbon atoms, and preferably to straight chain alkylene particularly containing 3 to 10 carbon atoms, more particularly 4 to 8 carbon atoms. For example, they include methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decanylene, undecanylene and dodecanylene.
Lower alkyl expressed by R.sub.3 and R.sub.4 denotes alkyl containing 1 to 4 carbon atoms which include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl and tert-butyl. Lower hydroxyalkyl denotes hydroxyalkyl containing 1 to 4 carbon atoms such as hydroxymethyl, hydroxyethyl, hydroxypropyl, hydroxybutyl. Cycloalkyl denotes cycloalkyl containing 3 to 8 carbon atoms which include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl. Lower alkyl, lower alkoxy and halogen atoms as substituents on phenyl ring in R.sub.3 and R.sub.4 incl

REFERENCES:
patent: 3267104 (1966-08-01), Hermans et al.
patent: 4795752 (1989-01-01), Hattori et al.
patent: 5389630 (1995-02-01), Sato et al.
patent: 5478941 (1995-12-01), Cossement et al.
Abstract for JP153280 (Jul. 8, 1987).
Abstract for JP233670 (Sep. 17, 1990).

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