EP0402644A1
Expired / Lapsed
EP
⏱️ 0.0 years remaining
N-(aryloxyalkyl)heteroarylpiperidines and -heteroarylpiperazines,a process for their preparation and their use as medicaments
Assignee: Aventis Pharmaceuticals Inc
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Filing: 1990-05-16
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Granted: —
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Expires: 2010-05-16
Abstract
Abstract This invention related to compounds of the formula: wherein X is -0-, -S-, - N H, or - N -R 2 ; p is 1 or 2; Y is hydrogen, C 1 to C 6 alkyl, -OH, Cl, F, Br, I, C 1 to C 6 alkoxy, -CF 3 , N0 2 , or -NH 2 , when p is 1; Y is C 1 to C 6 alkoxy when p is 2 and X is -0-; R 2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl. alkanoyl, and phenyl sulfonyl groups; Z is -CH- or -N-; n is 2, 3, 4, or 5; R is hydrogen, alkyl, C 1 - Cs-alkoxy, hydroxyl, carboxyl, Cl, F, Br, I, amino, C 1 - C 6 -mono or-dialryl amino, -N0 2 , lower alkyl thiol -OCF 3 , cyano, acylamino, -CF 3 , trifluoroacetyl, aminocarbonyl, or where alkyl is lower alkyl; aryl is phenyl or R 1 is hydrogen, lower alkyl, Ci - C 6 alkoxy, hydroxy, Cl, F, Br, I, C 1 - C 6 alkyl amino, -N0 2 , -CN. -CF 3 , -OCF 3 ; and heteroaryl is where Q is -O-, -S-, - NH, -CH = N; R 3 is hydrogen, lower alkyl, or acyl; and m is 1, 2, or 3; or a pharmaceutically acceptable acid addition salt thereof. The invention relates further to a process for the preparation of the above compounds and their use as medicaments having antipsychotic and/or analgetic activity.
Inventors
- 👤 Joseph Thomas Strupczewski
- 👤 Grover Cleveland Helsley
- 👤 Yulin Chiang
- 👤 Kenneth J. Bordeau
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-05 02:34
CPC Classifications
C; C07; C07D; C07D231/00; C07D231/54; C07D231/56; A; A61; A61P; A61P23/00; A61P25/00; A61P25/04; A61P25/18; C07D261/00; C07D261/20; C07D275/00; C07D275/04; C07D401/00; C07D401/02; C07D401/04; C07D413/00; C07D413/02; C07D413/04; C07D417/00; C07D417/02; C07D417/04
Claims Analysis
Total Claims: 15
Claim 1
Independent Claim
213 words
A compound of the formula: wherein X is -0-, -S-, -NH-, or - N -R 2 ; p is 1 or 2; Y is hydrogen, C 1 to C 6 alkyl, -OH, Cl, F, Br, I, C, to C 6 alkoxy, -CF 3 , -N0 2 , or -NH 2 , when p is 1; Y is lower alkoxy when p is 2 and X is -0-; R 2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, and phenyl sulfonyl groups; Zis-CH-or-N-; n is 2, 3, 4, or 5; R is hydrogen, alkyl, C 1 - C 6 alkoxy, hydroxyl, carboxyl, Cl, F, Br, I, amino, C 1 - C 6 mono or dialkyl amino, -NO 2 , lower alkyl thio, -OCF 3 , cyano, acylamino, -CF 3 , trifluoroacetyl, aminocarbonyl, or alkyl is lower alkyl; aryl is phenyl or where R 1 is hydrogen, lower alkyl, C 1 - C 6 alkoxy, hydroxy, Cl, F, Br, I, C 1 - C 6 alkyl amino, -N0 2 , -CN, -CF 3 , -OCF 3 ; heteroaryl is Q is -0-, -S-, - N H, -CH = N; R 3 is hydrogen, lower alkyl, or acyl; and misl,2,or3; or a pharmaceutically acceptable acid addition salt thereof.
Claim 2
Dependent Claim
213 words
A compound of the formula: wherein X is -0-, -S-, -NH-, or - N -R 2 ; p is 1 or 2; Y is hydrogen, C 1 to C 6 alkyl, -OH, Cl, F, Br, I, C, to C 6 alkoxy, -CF 3 , -N0 2 , or -NH 2 , when p is 1; Y is lower alkoxy when p is 2 and X is -0-; R 2 is selected from the group consisting of lower alkyl, aryl lower alkyl, aryl, cycloalkyl, aroyl, alkanoyl, and phenyl sulfonyl groups; Zis-CH-or-N-; n is 2, 3, 4, or 5; R is hydrogen, alkyl, C 1 - C 6 alkoxy, hydroxyl, carboxyl, Cl, F, Br, I, amino, C 1 - C 6 mono or dialkyl amino, -NO 2 , lower alkyl thio, -OCF 3 , cyano, acylamino, -CF 3 , trifluoroacetyl, aminocarbonyl, or alkyl is lower alkyl; aryl is phenyl or where R 1 is hydrogen, lower alkyl, C 1 - C 6 alkoxy, hydroxy, Cl, F, Br, I, C 1 - C 6 alkyl amino, -N0 2 , -CN, -CF 3 , -OCF 3 ; heteroaryl is Q is -0-, -S-, - N H, -CH = N; R 3 is hydrogen, lower alkyl, or acyl; and misl,2,or3; or a pharmaceutically acceptable acid addition salt thereof.
Claim 3
Dependent Claim
15 words
A compound as claimed in claim 1, wherein X is -0-, -S-, - N H.
Claim 4
Dependent Claim
29 words
A compound as claimed in claim 2, wherein n is 2, 3 or 4" Y is hydrogen or is chlorine or fluorine in the 6-position and p is 1.
Claim 5
Dependent Claim
49 words
A compound as claimed in claim 3, wherein R is hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 - alkylthio, halogen, C 1 -C 6 -alkylamino alkyl, -phenyl or -CH(OR 3 )-C 1 -C 6 -alkyl and m is 2 or 3.
Claim 6
Dependent Claim
26 words
A compound as claimed in claim 3, wherein n is 3 or 4 m is 2, and R is -OCH 3 and - -CH 3 .
Claim 7
Dependent Claim
18 words
A compound as claimed in claim 1, which is 1-[4-[3-[4-(1H-indazol-3-yl)-1-piperazinyl]propoxy]-3-methoxyphenyl]ethanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 8
Dependent Claim
18 words
A compound as claimed in claim 1, which is 1-[4-[3-[4-(1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl)ethanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 9
Dependent Claim
18 words
A compound as claimed in claim 1 which is 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol3-yl)-1-piperidinyl)-propoxy]-3-methoxyphenyl]ethanone or a pharmaceutically acceptable acid addtion salt thereof.
Claim 10
Dependent Claim
19 words
A compound as claimed in claim 1, which is 1-[4-[4-[4-(1,2-benzisoxazol-3-yl)-1-piperidinyl]butoxy]-3-methoxy. phenyl]ethanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 11
Dependent Claim
19 words
A compound as claimed in claim 1, which is 1-[4-[4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-butoxy]- 3-methoxyphenyl]ethanone or a pharmaceutically acceptable acid addition salt thereof.
Claim 12
Dependent Claim
21 words
A pharmaceutical composition, which comprises as the action ingredient a compound as claimed in claim 1 and a suitable carrier therefor.
Claim 13
Dependent Claim
20 words
Use of a compound as claimed in claim 1 for the preparation of a medicament having antipsychotic and/or analgetic activity.
Claim 14
Dependent Claim
238 words
A process for the preparation of a compound as claimed in claim 1, which comprises a) reacting a compound of the formula II wherein X, Y, Z and p are as defined, under alkylating conditions with a compound of the formula III wherein R, m and n are as defined and Hal is chlorine or bromine b) optionally reducing a compound of the formula I, wherein R is alkyl to obtain a compound of the formula I, wherein R is CH 2 (OH)-C 1 -C 6 -alkyl, c) optionally reacting a compound of the formula I, wherein R is -CH(OR 3 )-C 1 -C 6 -alkyl, where R 3 is hydrogen, with an alcanoic acid anhydride to obtain a compound of the formula I, wherein R is C·-C 6 - alkanoyl, d) optionally reacting a compound of the formula I, wherein R is hydroxy, first with a strong base and then with a compound of the formula Hal-C 1 -C 6 -alkyl, where Hal is chlorine or bromine, to obtain a compound of the formula I, where R is C 1 -C 6 -alkoxy, e) optionally reacting a compound of the formula I, wherein X is N-R 2 , and R 2 is hydrogen, with a C 1 -Cs-alkanoyl or aroyl halide to obtain a compound of the formula I, wherein X is NR 2 , and R 2 is C 1 -C 6 - alkanoyl or aroyl.
Claim 15
Dependent Claim
41 words
A process as claimed in claim 14 wherein the reaction of step a) is carried out in an inert solvent at a temperature of from 50° C to the reflux temperature of the solvent in the presence of an acid receptor.
References Cited (Backward Citations)
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