GB997166A - N-phenylpiperazine derivatives - Google Patents

N-phenylpiperazine derivatives

Info

Publication number
GB997166A
GB997166A GB2570161A GB2570161A GB997166A GB 997166 A GB997166 A GB 997166A GB 2570161 A GB2570161 A GB 2570161A GB 2570161 A GB2570161 A GB 2570161A GB 997166 A GB997166 A GB 997166A
Authority
GB
United Kingdom
Prior art keywords
group
general formula
mono
reducing
hydrogen atom
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB2570161A
Inventor
Anthony Stanley Fenton Ash
Andrew Malcolm Creighton
William Robert Wragg
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
May and Baker Ltd
Original Assignee
May and Baker Ltd
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 May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB2570161A priority Critical patent/GB997166A/en
Priority to LU42041D priority patent/LU42041A1/xx
Priority to ES0279201A priority patent/ES279201A1/en
Publication of GB997166A publication Critical patent/GB997166A/en
Expired legal-status Critical Current

Links

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
    • C07D295/04—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
    • C07D295/06—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 halogen atoms or nitro radicals
    • C07D295/073—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 halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents 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
    • C07D295/08—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
    • C07D295/084—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
    • 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
    • C07D295/10—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 doubly bound oxygen or sulphur atoms
    • C07D295/104—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • 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
    • C07D295/10—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 doubly bound oxygen or sulphur atoms
    • C07D295/112—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 doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

The invention comprises bases of the general formula <FORM:0997166/C2/1> (wherein X represents a straight, saturated or ethylenically unsaturated C2-4 hydrocarbon chain which may be substituted by a hydroxy or oxo group on the carbon atom adjacent to the phenyl group, R1 represents a carbamoyl, mono- or di-N-alkylcarbamoyl, sulphamoyl, mono- or di-N-alkylsulphamoyl, alkylcarbonyl, alkoxycarbonyl, cyano, alkylthio, alkylsulphinyl, alkylsulphonyl, hydroxyalkyl, nitro, aminomono- or di-alkylamino, acylamido (including alkanesulphonamido), carboxy or trifluoromethylthio group, R2 represents a hydrogen atom, a nitro group or a group -NR4R5, wherein R4 and R5 are the same or different and each represent a hydrogen atom or an alkyl or hydroxyalkyl group and R5 may additionally represent a carbon-containing acyl (including alkanesulphonyl) group or a carbamoyl, mono- or di-N-alkylcarbamoyl, thiocarbamoyl, mono- or di-N-alkylthiocarbamoyl, alkoxycarbonyl, chloroalkoxycycarbonyl or alkoxycarbonylalkyl group, or R4 and R5, together with the nitrogen atom to which they are attached represent a monocyclic 5- or 6-membered heterocyclic group (e.g. a 2-oxo-oxazolidino group obtainable by the action of an alkali metal hydroxide on a b -chloroethoxy-carbonylamino group), and R3 represents a hydrogen atom or an alkoxy group) and their toxic acid addition salts, and pharmaceutical compositions containing these compounds in association with a pharmaceutically acceptable carrier, and the preparation of the bases by (a) reacting an N-phenylpiperazine of the general formula <FORM:0997166/C2/2> with a compound of the general formula <FORM:0997166/C2/3> (wherein Y represents the acid residue of a reactive ester), or (when X is -CH2CH2- or -CH2-CH = CH-CH2- and R2 is NO2) with a nitrostyrene or nitrobutadiene of the general formula <FORM:0997166/C2/4> (wherein n=0 or 1), or (b) interaction of compounds of the general formulae <FORM:0997166/C2/5> and <FORM:0997166/C2/6> (wherein one of the symbols Z1 and Z2 represents a hydrogen atom and the other a group -CH2CH2-Y), or (c) (when X contains a CH2 group adjacent to the nitrogen atom of the piperazine nucleus) reducing a nitrile of the general formula <FORM:0997166/C2/7> (wherein B is-CH2-, -(CH2)2- or -(CH2)3-or such a grouping substituted by a hydroxy or oxo group on the carbon atom adjacent to the phenyl group) in the presence of an equimolecular proportion of an N-phenylpiperazine of the second general formula above, and in all cases, if desired, subsequently replacing either or both or R1 and R2 by a different group within the definitions thereof (e.g. reducing NO2 to NH2, alkylating, hydroxyalkylating, or acylating the latter, hydrolysing an acylamido group or reducing it to alkylamino, or hydrolysing -CN to -COOH). Starting materials are prepared as follows: m - (N,N - Dimethylsulphamoyl) - N,N - di-(b - bromoethyl) - aniline by condensing m-nitrobenzenesulphonyl chloride with dimethylamine to form m-N,N-dimethylsulphamoylnitrobenzene, reducing this to m-N,N-dimethylsulphamoylaniline. reacting this with ethylene oxide, and treating the resulting m-(N,N-dimethylsulphamoyl) - N,N - di - (b - hydroxyethyl)-aniline with phosphorus tribromide. m - N,N - Di - (b - chloroethyl) - aminoacetophenone by reacting m-aminoacetophenone with ethylene oxide and treating the resulting m-N,N - di - (b - hydroxyethyl) - aminoacetophenone with phosphorus oxychloride. N,N - Di - (b - chloroethyl) - p - nitrophenylethylamine hydrochloride by condensing p-nitrophenethyl bromide with diethanolamine and treating the resulting N,N-di-(b -hydroxyethyl) - p - nitrophenylethylamine with thionyl chloride. 1 - (m - Methylsulphonylphenyl) - piperazine by heating m-methylsulphonylaniline with diethanolamine and concentrated hydrochloric acid. The pharmaceutical compositions, which are suitable for the treatment of psychiatric disorders, may be in forms suitable for oral or parenteral administration, e.g. tablets, pills, dispersable powders, granules, emulsions, solutions, suspensions, syrups, elixirs and capsules.
GB2570161A 1961-07-14 1961-07-14 N-phenylpiperazine derivatives Expired GB997166A (en)

Priority Applications (3)

Application Number Priority Date Filing Date Title
GB2570161A GB997166A (en) 1961-07-14 1961-07-14 N-phenylpiperazine derivatives
LU42041D LU42041A1 (en) 1961-07-14 1962-07-12
ES0279201A ES279201A1 (en) 1961-07-14 1962-07-13 N-phenylpiperazine derivatives

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2570161A GB997166A (en) 1961-07-14 1961-07-14 N-phenylpiperazine derivatives

Publications (1)

Publication Number Publication Date
GB997166A true GB997166A (en) 1965-07-07

Family

ID=10231904

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2570161A Expired GB997166A (en) 1961-07-14 1961-07-14 N-phenylpiperazine derivatives

Country Status (3)

Country Link
ES (1) ES279201A1 (en)
GB (1) GB997166A (en)
LU (1) LU42041A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4413006A (en) * 1980-02-18 1983-11-01 Tanabe Seiyaku Co., Ltd. N-Aryl-N-phenoxy-alkyl-piperazine compounds useful in decreasing intracranial pressure
US4797401A (en) * 1986-08-09 1989-01-10 Pfizer Inc. 4-Substituted-1-(4-alkylsulphonamidophenyl)piperazines as antiarrhythmic agents

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4613598A (en) * 1984-03-13 1986-09-23 Mitsubishi Chemical Industries Limited Piperazine derivatives and their acid addition salts

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4413006A (en) * 1980-02-18 1983-11-01 Tanabe Seiyaku Co., Ltd. N-Aryl-N-phenoxy-alkyl-piperazine compounds useful in decreasing intracranial pressure
US4797401A (en) * 1986-08-09 1989-01-10 Pfizer Inc. 4-Substituted-1-(4-alkylsulphonamidophenyl)piperazines as antiarrhythmic agents

Also Published As

Publication number Publication date
LU42041A1 (en) 1962-11-10
ES279201A1 (en) 1963-02-16

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