GB1378080A - Oxime derivatives of halophenyl piperazinylalkyl ketones and methods for their preparation - Google Patents

Oxime derivatives of halophenyl piperazinylalkyl ketones and methods for their preparation

Info

Publication number
GB1378080A
GB1378080A GB5611672A GB5611672A GB1378080A GB 1378080 A GB1378080 A GB 1378080A GB 5611672 A GB5611672 A GB 5611672A GB 5611672 A GB5611672 A GB 5611672A GB 1378080 A GB1378080 A GB 1378080A
Authority
GB
United Kingdom
Prior art keywords
oxime
hal
halide
carbonyl
aliphatic
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
GB5611672A
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.)
Bruneau & Cie Lab
Original Assignee
Bruneau & Cie Lab
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 Bruneau & Cie Lab filed Critical Bruneau & Cie Lab
Publication of GB1378080A publication Critical patent/GB1378080A/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
    • C07D295/12—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
    • C07D295/125—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—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 attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain

Landscapes

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

Abstract

1378080 Oxime derivatives of α-halophenyl-#- piperazinyl-alkanones LES LABORATOIRES BRUNEAU ET CIE and A BUZAS 5 Dec 1972 [10 Dec 1971] 56116/72 Heading C2C Novel compounds I in which X is halogen, R 3 is an arylaliphatic or aromatic group (in which the piperazinyl ring is attached to a ring carbon atom when R 3 is an aromatic group), R 2 is an aliphatic group containing 1 to 3 C atoms and R 1 is an aliphatic hydrocarbyl group optionally substituted by a tertiary amino radical, an alkyl-carbonyl radical or an aralkyl-aralkenyl-, phehyl-, furyl- or pyridyl-carbonyl group in which the aromatic ring may be substituted by up to 3 radicals chosen from alkyl, alkoxy and halogen and acid addition salts thereof are prepared by reaction of the corresponding novel oxime in which R 1 is hydrogen with a halide (R 1 -Hal). When R 1 - Hal represents an aliphatic halide the oxime is used as its sodium or potassium salt in an alcoholic solvent. When R 1 -Hal is an acid halide, pyridine is used as a solvent and the hydrohalide salt is obtained directly. X is chlorine or fluorine; R 3 is phenyl or piperonyl, R 2 is -CH 2 -, -CH(CH 3 )-, -CH 2 ) 2 -, or -(CH 2 ) 3 -; R 1 is allyl, propargyl, #-diethylaminoethyl, #-morpholinoethyl, di-n-propylacetyl, p-n-butoxy-phenyl-acetyl, cinnamoyl, 3,4,5-trimethoxy benzoyl, 3,4-dichlorobenzoyl, 2,5-dimethyl-3-furyl carbonyl or 2-chloronicotinoyl. Novel oximes of Formula I in which R 1 is hydrogen are prepared by reaction of the corresponding ketone with hydroxylamine hydrochloride preferably in presence of sodium hydroxide in an aqueous alcoholic solvent. Compounds I are useful as analgesic antiinflammatory or musculotropic spasmolytic agents and also have psychosedative properties. They form with a carrier a pharmaceutical composition which may be administered orally or parenterally.
GB5611672A 1971-12-10 1972-12-05 Oxime derivatives of halophenyl piperazinylalkyl ketones and methods for their preparation Expired GB1378080A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7144460A FR2162312B1 (en) 1971-12-10 1971-12-10

Publications (1)

Publication Number Publication Date
GB1378080A true GB1378080A (en) 1974-12-18

Family

ID=9087286

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5611672A Expired GB1378080A (en) 1971-12-10 1972-12-05 Oxime derivatives of halophenyl piperazinylalkyl ketones and methods for their preparation

Country Status (3)

Country Link
DE (1) DE2257639A1 (en)
FR (1) FR2162312B1 (en)
GB (1) GB1378080A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006061372A2 (en) * 2004-12-07 2006-06-15 Solvay Pharmaceuticals B.V. Phenylpiperazines with a combination of affinity for dopamine -d2 receptors and serotonin reuptake sites
US7371769B2 (en) 2004-12-07 2008-05-13 Solvay Pharmaceuticals B.V. Tetrahydropyridin-4-yl indoles with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites
US8101619B2 (en) 2004-12-08 2012-01-24 Solvay Pharmaceuticals B.V. Phenylpiperazine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6463574A (en) * 1987-09-03 1989-03-09 Mitsubishi Chem Ind Ethanone oximes
DK270488D0 (en) * 1988-05-18 1988-05-18 Novo Industri As Hitherto unknown O-SUBSTITUTED KETOXIMES
US5665756A (en) * 1994-08-03 1997-09-09 Hoechst Marion Roussel, Inc. Aminoalkyloximes useful in the treatment of depression and obsessive compulsive disorders
JP2007524620A (en) * 2003-06-19 2007-08-30 サイキアトリク・ゲノミクス・インコーポレーテッド Dual-functional compound and use thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006061372A2 (en) * 2004-12-07 2006-06-15 Solvay Pharmaceuticals B.V. Phenylpiperazines with a combination of affinity for dopamine -d2 receptors and serotonin reuptake sites
WO2006061372A3 (en) * 2004-12-07 2006-11-23 Solvay Pharm Bv Phenylpiperazines with a combination of affinity for dopamine -d2 receptors and serotonin reuptake sites
US7371769B2 (en) 2004-12-07 2008-05-13 Solvay Pharmaceuticals B.V. Tetrahydropyridin-4-yl indoles with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites
US8101619B2 (en) 2004-12-08 2012-01-24 Solvay Pharmaceuticals B.V. Phenylpiperazine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition

Also Published As

Publication number Publication date
DE2257639A1 (en) 1973-07-19
FR2162312B1 (en) 1975-02-07
FR2162312A1 (en) 1973-07-20

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee