WO1997044334A3 - Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and a process for their preparation - Google Patents

Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and a process for their preparation Download PDF

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Publication number
WO1997044334A3
WO1997044334A3 PCT/HU1997/000020 HU9700020W WO9744334A3 WO 1997044334 A3 WO1997044334 A3 WO 1997044334A3 HU 9700020 W HU9700020 W HU 9700020W WO 9744334 A3 WO9744334 A3 WO 9744334A3
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WO
WIPO (PCT)
Prior art keywords
group
preparation
pharmaceutical compositions
compositions containing
same
Prior art date
Application number
PCT/HU1997/000020
Other languages
French (fr)
Other versions
WO1997044334A2 (en
Inventor
Simonek Ildiko Ratzne
Daniel Bozsing
Ivan Jakoczi
Lax Gyorgyi Kovanyine
Gabor Blasko
Gyula Simig
Istvan Gacsalyi
Eva Schmidt
Kavacs Aniko Miklosne
Kiszelly Eniko Szirtne
Gabor Szenasi
Istvan Gyertyan
Andras Egyed
Karoly Tihanyi
Original Assignee
Egyt Gyogyszervegyeszeti Gyar
Simonek Ildiko Ratzne
Daniel Bozsing
Ivan Jakoczi
Lax Gyorgyi Kovanyine
Gabor Blasko
Gyula Simig
Istvan Gacsalyi
Eva Schmidt
Miklosne Kovacs Aniko
Kiszelly Eniko Szirtne
Gabor Szenasi
Istvan Gyertyan
Andras Egyed
Karoly Tihanyi
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Egyt Gyogyszervegyeszeti Gyar, Simonek Ildiko Ratzne, Daniel Bozsing, Ivan Jakoczi, Lax Gyorgyi Kovanyine, Gabor Blasko, Gyula Simig, Istvan Gacsalyi, Eva Schmidt, Miklosne Kovacs Aniko, Kiszelly Eniko Szirtne, Gabor Szenasi, Istvan Gyertyan, Andras Egyed, Karoly Tihanyi filed Critical Egyt Gyogyszervegyeszeti Gyar
Priority to AU29120/97A priority Critical patent/AU2912097A/en
Publication of WO1997044334A2 publication Critical patent/WO1997044334A2/en
Publication of WO1997044334A3 publication Critical patent/WO1997044334A3/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
    • C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
    • C07D243/08—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
    • C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/135—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/155—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings

Abstract

The invention refers to novel piperazine and homopiperazine derivatives of formula (I) being suitable for the treatment of dieseases due to pathological alterations of the central nervous system, pharmaceutical compositions containing the above derivatives, and a process for the preparation of the novel compounds. In formula (I) R1 stands for a halo, a C¿1-4? alkyl group, a C1-4 alkoxy group, a trihalomethyl group, a nitro group or an amino group which latter can be substituted by a C1-4 alkyl group, and n has a value of 1 or 2, or R?1¿ represents a cyano group, and n has a value of 2, m is 0, 1, 2 or 3, R?2, R3 and R4¿ mean, independently, a hydrogen, a halo, a trihalomethyl group, a C¿1-4? alkyl group, a C1-4 alkoxy group, a nitro group, a carboxy group, a formyl group, a hydroxy group or an amino group which latter can be substituted by a C1-4 alkyl group.
PCT/HU1997/000020 1996-05-17 1997-05-15 Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and a process for their preparation WO1997044334A2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU29120/97A AU2912097A (en) 1996-05-17 1997-05-15 Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and process for their preparation

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
HU9601331A HUP9601331A3 (en) 1996-05-17 1996-05-17 Piperazine- and homopiperazine-derivatives, process for producing them and pharmaceutical compositions containing them
HUP9601331 1996-05-17

Publications (2)

Publication Number Publication Date
WO1997044334A2 WO1997044334A2 (en) 1997-11-27
WO1997044334A3 true WO1997044334A3 (en) 1998-03-12

Family

ID=89993978

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/HU1997/000020 WO1997044334A2 (en) 1996-05-17 1997-05-15 Novel piperazine or homopiperazine derivatives, pharmaceutical compositions containing the same and a process for their preparation

Country Status (3)

Country Link
AU (1) AU2912097A (en)
HU (1) HUP9601331A3 (en)
WO (1) WO1997044334A2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5859246A (en) * 1997-01-30 1999-01-12 Neurogen Corporation 1-phenyl-4-benzylpiperazines: dopamine receptor subtype specific ligands
EP1091949A2 (en) * 1998-06-30 2001-04-18 Neurogen Corporation 6-(4-arylalkylpiperazin-1-yl)benzodioxane and 6-(4-arylalkylpiperazin-1-yl)chromane derivatives: dopamine receptor subtype specific ligands
US6177566B1 (en) 1998-06-30 2001-01-23 Neurogen Corporation 6-(4-arylalkylpiperazin-1-yl) benzodioxane and 6-(4-arylalkylpiperazin-1-yl) chromane derivatives: dopamine receptor subtype specific ligands
WO2002004433A2 (en) 2000-07-06 2002-01-17 Neurogen Corporation Melanin concentrating hormone receptor ligands
AU2001280438A1 (en) 2000-07-27 2002-02-13 Eli Lilly And Company Substituted heterocyclic amides
KR20040012851A (en) 2001-05-22 2004-02-11 뉴로젠 코포레이션 Melanin concentrating hormone receptor ligands: substituted 1-benzyl-4-aryl piperazine analogues
WO2005110982A2 (en) 2004-04-07 2005-11-24 Neurogen Corporation Substituted 1-benzyl-4-substituted piperazine analogues
EP2149373A1 (en) * 2008-08-01 2010-02-03 Laboratorios Del. Dr. Esteve, S.A. 5HT7 receptor ligands and compositions comprising the same

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4139621A (en) * 1976-12-10 1979-02-13 Beecham Group Limited N-(4-substituted-3,5-dichloro-phenyl)-piperazines
GB2057441A (en) * 1979-08-25 1981-04-01 Merz & Co Arylpiperazines
WO1993000313A2 (en) * 1991-06-27 1993-01-07 Virginia Commonwealth University Sigma receptor ligands and the use thereof
EP0556889A1 (en) * 1992-02-18 1993-08-25 Duphar International Research B.V Method of preparing aryl(homo)piperazines
EP0650964A1 (en) * 1993-11-02 1995-05-03 Duphar International Research B.V 1 2H-1-benzopyran-2-one-8-yl -piperazine derivatives
EP0711763A1 (en) * 1993-07-28 1996-05-15 Santen Pharmaceutical Co., Ltd. Novel 1,4-di(phenylalkyl)piperazine derivative

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4139621A (en) * 1976-12-10 1979-02-13 Beecham Group Limited N-(4-substituted-3,5-dichloro-phenyl)-piperazines
GB2057441A (en) * 1979-08-25 1981-04-01 Merz & Co Arylpiperazines
WO1993000313A2 (en) * 1991-06-27 1993-01-07 Virginia Commonwealth University Sigma receptor ligands and the use thereof
EP0556889A1 (en) * 1992-02-18 1993-08-25 Duphar International Research B.V Method of preparing aryl(homo)piperazines
EP0711763A1 (en) * 1993-07-28 1996-05-15 Santen Pharmaceutical Co., Ltd. Novel 1,4-di(phenylalkyl)piperazine derivative
EP0650964A1 (en) * 1993-11-02 1995-05-03 Duphar International Research B.V 1 2H-1-benzopyran-2-one-8-yl -piperazine derivatives

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
CHEMICAL ABSTRACTS, vol. 77, no. 7, 14 August 1972, Columbus, Ohio, US; abstract no. 48507n, HASEGAWA: "1-m-Trifluoromethylphenyl-4-arylpiperazines" XP002041903 *
GLENNON ET AL.: "Novel 1-phenylpiperazine and 4-phenylpiperidine derivatives as high affinity sigma ligands", J.MED.CHEM., vol. 34, 1991, pages 3360 - 3365, XP002041902 *
MOKROSZ ET AL.: "Quantitative analysis of the alkyl chain effects on the 5-HT1a and 5-HT2 receptor affinities of 4-alkyl-1-arylpiperazines and their analogs", ARCH. PHARM., vol. 328, no. 2, February 1995 (1995-02-01), pages 143 - 148, XP002041901 *
MOKROSZ J L ET AL: "Structure-activity relationship studies of central nervous system (CNS) agents. 5. Effect of the hydrocarbon chain on the affinity of 4-substituted 1-(3-chlorophenyl)piperazines for 5-HT1A receptor sites", J. MED. CHEM. (JMCMAR,00222623);92; VOL.35 (13); PP.2369-74, POL. ACAD. SCI.;INST. PHARMACOL.; KRAKOW; 31-343; POL. (PL), XP002041900 *

Also Published As

Publication number Publication date
HUP9601331A2 (en) 1998-09-28
WO1997044334A2 (en) 1997-11-27
HUP9601331A3 (en) 2000-06-28
AU2912097A (en) 1997-12-09
HU9601331D0 (en) 1996-07-29

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