Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide

a technology of cns disorders and trans napthalenamine, which is applied in the field of treating cns disorders with trans napthalenamine and its formamide, can solve the problems of lack of evidence in the literature, and achieve the effect of being useful for the prophylaxis of migrain

Inactive Publication Date: 2006-06-15
SEPACOR INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Sanchez et al., Cellular and Molecular Neurobiology, 19: 467 (1999), speculated that despite its lower potency, desmethylsertraline might play a role in the therapeutic effects of sertraline but, there is presently no evidence in the literature to support this theory.

Method used

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  • Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide
  • Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide
  • Treatment of CNS disorders with trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and its formamide

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Embodiment Construction

[0016] The present invention provides several embodiments of a method for treating one or more CNS disorders. The method encompasses administering pure P or pure Q, or any mixture thereof. Administration of either compound or any combination thereof, including the racemic mixture of trans isomers, results in a broad therapeutic profile and avoidance of side effects that are associated with an imbalance among the distribution of activity between norepinephrine, serotonin and dopamine receptors.

[0017] Preparation of compounds of the present invention is illustrated below in Scheme 1 and its accompanying narrative.

[0018] In the compound

R is

wherein R1, R2 and R3 are each independently alkyl. In a preferred embodiment of the compounds, R is tert-butyl.

[0019] N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]formamide, the intermediate in the synthesis shown in Scheme 1, exists in four stereoisomeric forms:

[0020] When N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronapht...

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Abstract

Treatment of CNS disorders with (1R,4S)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine; and (1S,4R)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is disclosed. A process for preparing 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine is also disclosed. The process includes the preparation of all four isomers of N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl]formamide, which are also useful.

Description

CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application is a continuation of U.S. Ser. No. 10 / 663,173, filed Sep. 16, 2003, which claims priority of provisional application 60 / 411,304 and 60 / 411,305, both filed Sep. 16, 2002, the entire disclosures of which are incorporated herein by reference.FIELD OF THE INVENTION [0002] The present invention relates to methods of treating central nervous system (CNS) disorders using (1R,4S)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine; (1S,4R)-trans 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-1-napthalenamine and the four isomers of N-[4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydronaphthalen-1-yl] formamide. BACKGROUND OF THE INVENTION [0003] Clinicians recognize a distinction among central nervous system illnesses, and there have been many schemes for categorizing mental disorders. The Diagnostic and Statistical Manual of Mental Disorders, Fourth Ed., Text Revision, (hereinafter, the “DSM-IV-TR™”), published by the American ...

Claims

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Application Information

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Patent Type & AuthorityApplications(United States)
IPC IPC(8): C07C211/44A61K9/20A61K9/48A61K31/135A61P25/00A61P25/06A61P25/08A61P25/14A61P25/16A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30C07C209/62C07C211/42
CPCC07B2200/07C07C211/42C07C2102/10C07C2102/28C07C2602/10C07C2602/28A61P25/00A61P25/06A61P25/08A61P25/14A61P25/16A61P25/20A61P25/22A61P25/24A61P25/28A61P25/30A61P3/04A61K31/135
InventorJERUSSI, THOMAS P.FANG, QUN KEVINCURRIE, MARK G.
OwnerSEPACOR INC