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Claims for Patent: 4,895,841

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Claims for Patent: 4,895,841

Title: Cyclic amine compounds with activity against acetylcholinesterase
Abstract:A cyclic amine compound is defined by the formula: ##STR1## in which J is indanyl, indanonyl, indenyl, indenonyl, indanedionyl, tetralonyl, benzosuberonyl, indanolyl or a divalent group thereof, K is phenyl, an arylalkyl or cynnamyl, B is --(CHR22)r--, R22 being H or methyl, --CO--(CHR22)r--, .dbd.(CH--CH.dbd.CH)b--, .dbd.CH--(CH2)c-- or .dbd.(CH--CH)d.dbd. and the ring including T and Q is piperidine. The compound is useful to treat senile dementia.
Inventor(s): Sugimoto; Hachiro (Ushiku, JP), Tsuchiya; Yutaka (Fort Lee, NJ), Higurashi; Kunizou (Tokyo, JP), Karibe; Norio (Tsukuba, JP), Iimura; Youichi (Tsukuba, JP), Sasaki; Atsushi (Tsukuba, JP), Yamanishi; Yoshiharu (Ryugasaki, JP), Ogura; Hiroo (Tsuchiura, JP), Araki; Shin (Tsukuba, JP), Kosasa; Takashi (Tsukuba, JP), Kubota; Atsuhiko (Tsukuba, JP), Kosasa; Michiko (Tsukuba, JP), Yamatsu; Kiyomi (Kamakura, JP)
Assignee: Eisai Co., Ltd. (Tokyo, JP)
Application Number:07/209,339
Patent Claims: 1. A cyclic amine compound having the formula ##STR327## wherein r is an integer of 1 to 10 , R.sup.22 is hydrogen or methyl, and the R.sup.22 radicals can be the same or different when r is from 2 to 10;

K is phenylalkyl or phenylalkyl having a substituent on the phenyl ring;

S is hydrogen or a substituent on the phenyl ring, and

t is an integer of 1 to 4, with the proviso that (S).sub.t can be a methylenedioxy group or an ethylenedioxy group joined to two adjacent carbon atoms of the phenyl ring; and

q is an integer of 1 to 3,

or a pharmacologically acceptable salt thereof.

2. A cyclic amine compound as claimed in claim 1 in which q is 2.

3. A cyclic amine compound as claimed in claim 1 in which K is benzyl, m-nitrobenzyl or m-fluorobenzyl.

4. A cyclic amine compound as claimed in claim 2 in which K is benzyl.

5. A cyclic amine compound as claimed in claim 1 in which S is lower alkyl having 1 to 6 carbon atoms or lower alkoxy having 1 to 6 carbon atoms.

6. A cyclic amine compound as claimed in claim 1 in which S is methoxy and t is an integer of from 1 to 3.

7. A cyclic amine compound as claimed in claim 1 in which r is an integer of 1 to 3.

8. A cyclic amine compound as claimed in claim 1, or a pharmacologically acceptable salt thereof, which is 1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine.

9. A cyclic amine compound as claimed in claim 1, or a pharmacologically acceptable salt thereof, which is selected from the group consisting of:

1-benzyl-4-((5-methoxy-1-indanon)-2-yl)methylpiperidine,

1-benzyl-4-((5,6-diethoxy-1-indanon)-2-yl)methylpiperidine,

1-benzyl-4-((5,6-methylenedioxy-1-indanon)-2-yl)methylpiperidine,

1-(m-nitrobenzyl)-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine,

1-(m-fluorobenzyl)-4-((5,6-dimethoxy-1-indanon)-2-yl)methylpiperidine,

1-benzyl-4-((5,6-dimethoxy-1-indanon)-2-yl)propylpiperidine and

1-benzyl-4-((5-isopropoxy-6-methoxy-1-indanon)-2-yl)methylpiperidine.

10. A therapeutic composition for treatment of a disease caused by acetylcholinesterase activity which comprises a pharmacologically effective amount of the cyclic amine compound as defined in claim 1 or a pharmacologically acceptable salt thereof, and pharmacologically acceptable carrier.

11. A method for treating a disease caused by acetylcholinesterase activity which comprises administering to a human patient having the disease, an effective amount of the cyclic amine compound as defined in claim 1, or a pharmacologically acceptable salt thereof.

12. A method as claimed in claim 11, in which the disease is the senile dementia.

13. A method as claimed in claim 11, in which the disease is senile dementia of the Alzheimer type.
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