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Heteroarylpiperidines, and their use as antipsychotics and analgetics

a technology of heteroarylpiperidines and piperazines, which is applied in the field of het, can solve the problems of known neuroleptics producing unwanted side effects, unable to cure psychotic patients, and almost certainly relaps

Inactive Publication Date: 2006-09-05
AVENTIS PHARMA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

While control of schizophrenic symptoms has been successful, treatment with these drugs does not cure the psychotic patient, who will almost certainly relapse if medication is discontinued.
Moreover, some of the known neuroleptics produce unwanted side effects.

Method used

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  • Heteroarylpiperidines, and their use as antipsychotics and analgetics
  • Heteroarylpiperidines, and their use as antipsychotics and analgetics
  • Heteroarylpiperidines, and their use as antipsychotics and analgetics

Examples

Experimental program
Comparison scheme
Effect test

example 1

Preparation of 1-[4-[3-[4-(1H-Indazol-3-yl)-1-piperpiperazinyl]propoxy]-3-methoxyphenyl]ethanone

(A) Synthesis of 2-bromobenzoic acid 2-phenylsulfonylhydrazide

[0491]To a solution of 2-bromobenzoic acid hydrazide (132 g) in pyridine (1.2 l) cooled to about 10° with an ice bath, was added benzensulfonyl chloride (78.3 ml). After complete addition, the reaction was stirred at ambient temperature for four hours, and then poured into ice-hydrochloric acid to precipitate a yellow solid, 135 g. The material was recrystallized from isopropanol to yield 125 g of 2-bromobenzoic acid 2-phenylsulfonylhydrazide, m.p.=154°-156° C.

(B) Synthesis of α-chloro-2-bromobenzaldehyde phenylsulfonylhydrazone

[0492]A mixture of 2-bromobenzoic acid phenylsulfonylhydrazide (125 g, 0.35 mol) and thionyl chloride (265 ml) was stirred and refluxed for 2 hours. After about 15 minutes of reflux, the solid went into solution. The reaction was permitted to cool, and then it was poured into hexane. The resultant white ...

example 2

1-[4-[3-[4-(1,2-Benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone

[0507]A mixture of 3-(4-piperidinyl)-1,2-benzisoxazole hydrochloride (4.8 g, 0.02 mol), K2CO3 (5.2 g, 0.04 mol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.3 g, 0.022 mol), a few crystals of KI and dimethylformamide (60 ml) was stirred at 90° C. for 16 hours. The reaction was poured into water and the aqueous mixture was extracted with ethyl acetate. The extract was washed (water), dried (MgSO4) and concentrated to afford a brown oil. The oil was chromatographed on a Waters Prep 500 utilizing silica gel columns and ethyl acetate-diethylamine (2%), as eluent. Concentration of the appropriate fractions afforded 3.9 g of product as an off-white solid. Recrystallization from absolute ethyl alcohol afforded 2.6 g (33%) of 1-[4-[3-[4-(1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone, m.p.=102°-104° C., as colorless needles.

[0508]ANALYSIS: Calculated for C24H28N2O4: 70.56% C 6.91...

example 3

1-[4-[3-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone

[0509]A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2 benzisoxazole hydrochloride (5.1 g, 0.02 mol), K2CO3 (5.2 g, 0.04 mol), 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone (5.3 g, 0.022 mol), and dimethylformamide (60 ml) was heated at 90° C. for 16 hours. The reaction was poured into water, and the aqueous mixture was extracted with ethyl acetate. The ethyl acetate was washed (water), dried (MgSO4) and concentrated to afford a moist solid. Recrystallization (twice) from ethyl alcohol afforded 5.0 g (58%) of 1-[4-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]propoxy]-3-methoxyphenyl]ethanone as a beige solid, m.p.=118°-120° C.

[0510]ANALYSIS: Calculated for C24H27FN2O4: 67.60% C 6.38% H 6.57% N Found: 67.47% C 6.40% H 6.53% N.

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Abstract

Heteroarylpiperidines, pyrrolidines, and piperazines are useful as antipsychotic and analgesic agents. The compounds are especially useful for treating psychoses by administering to a mammal a psychoses-treating effective amount of one of the compounds. The compounds are also useful as analgesics by administering a pain-relieving effective amount of one of the compounds to a mammal.

Description

CROSS-REFERENCE TO RELATED APPLICATION[0001]This is a continuation of application Ser. No. 07 / 969,383, filed Oct. 30, 1992 now U.S. Pat. No. 5,364,866, <?insert-start id="INS-S-00001" date="20060905" ?>which is the subject of Reissue application Ser. No. 09 / 712,129, filed Nov. 15, 2000, and <?insert-end id="INS-S-00001" ?>which is a continuation-in-part application of application Ser. No. 07 / 788,269 filed Nov. 5, 1991, now abandoned which is a continuation-in-part application of application Ser. No. 07 / 944,705, filed Sep. 5, 1991, now abandoned which is a continuation application of application Ser. No. 07 / 619,825, filed Nov. 29, 1990, now abandoned which is a continuation application of application Ser. No. 07 / 456,790, filed Dec. 29, 1989, now abandoned which is a continuation-in-part application of application Ser. No. 07 / 354,411, filed May 19, 1989 now abandoned.BACKGROUND OF THE INVENTION[0002]This invention relates to heteroarylpiperidines, pyrrolidines and piperaz...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): A61P25/04A61K31/44A61K31/495A61K31/55A61K31/505C07D221/04C07D401/04C07D403/04C07D417/04C07D419/04A61K31/00A61K31/09A61K31/12A61K31/40A61K31/41A61K31/415A61K31/4162A61K31/42A61K31/423A61K31/425A61K31/428A61K31/4427A61K31/445A61K31/4465A61K31/4523A61K31/454A61K31/496A61K31/506A61K31/535A61K31/5375A61K31/5377A61P25/18A61P29/00C07C45/45C07C45/67C07C45/71C07C47/277C07C47/575C07C49/84C07C233/25C07C233/33C07C255/54C07C323/22C07DC07D207/08C07D231/56C07D239/02C07D261/20C07D275/04C07D275/06C07D277/82C07D401/12C07D401/14C07D403/12C07D403/14C07D405/04C07D405/14C07D409/14C07D413/04C07D413/12C07D413/14C07D417/12C07D417/14C07D471/04C07F7/18
CPCC07C45/45C07C45/673C07C45/71C07C233/25C07C233/33C07C255/54C07C323/22C07D207/08C07D231/56C07D261/20C07D275/04C07D275/06C07D277/82C07D401/04C07D401/12C07D401/14C07D403/12C07D413/04C07D413/10C07D413/14C07D417/04C07D417/14C07D471/04C07F7/1804A61P25/04A61P25/18A61P29/00C07C49/84C07C47/575C07C49/755
Inventor STRUPCZEWSKI, JOSEPH T.BORDEAU, KENNETH J.GLAMKOWSKI, EDWARD J.CHIANG, YULINHELSLEY, GROVER C.
Owner AVENTIS PHARMA INC
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