GB705979A - 1.4-aralkyl piperazines and process for the preparation thereof - Google Patents

1.4-aralkyl piperazines and process for the preparation thereof

Info

Publication number
GB705979A
GB705979A GB3985/52A GB398552A GB705979A GB 705979 A GB705979 A GB 705979A GB 3985/52 A GB3985/52 A GB 3985/52A GB 398552 A GB398552 A GB 398552A GB 705979 A GB705979 A GB 705979A
Authority
GB
United Kingdom
Prior art keywords
benzyl
aralkyl
piperazine
benzhydryl
reaction
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
GB3985/52A
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.)
Individual
Original Assignee
Individual
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 Individual filed Critical Individual
Publication of GB705979A publication Critical patent/GB705979A/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
    • C07D295/02—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C07D295/027—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
    • C07D295/03—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 containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
    • 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
    • C07D295/096—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

Landscapes

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

Abstract

The invention comprises 1:4 aralkyl-piperazines in which the 1- and 4- positions are substituted by different aralkyl groups and the 2- and 5- positions may be substituted by alkyl radicles, and a process for preparing them by the reaction between an aralkyl halide and a 1-aralkyl piperazine, or by the reaction between an aldehyde and a 1-aralkyl-piperazine followed by reduction. In examples, 1-benzhydryl-4-benzyl-piperazine is prepared by the reaction between benzyl piperazine and benzhydryl chloride, benzhydryl-piperazine and benzyl chloride, and between benzhydrylpiperazine and benzaldehyde, followed by reduction; substituted derivatives obtainable by similar methods include the 1-p-chlorbenzhydryl-4-p-methoxybenzyl, 1-p-chlorobenzhydryl-4-benzyl, 1-p-bromobenzhydryl - 4 - benzyl-, 1 - p - p1 - di chlorobenzhydryl-4-benzyl-, 1-p-methylbenzhydryl-4-benzyl-, and other combinations of methoxy, ethoxy, methyl-, propyl-, butyl-, chloro- and bromosubstituted products; and by selecting as piperazine derivative one having alkyl groups on the 2- and 5- carbon atoms as starting material, similar products to the above derivatives are also obtained.
GB3985/52A 1951-03-22 1952-02-14 1.4-aralkyl piperazines and process for the preparation thereof Expired GB705979A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
BE705979X 1951-03-22

Publications (1)

Publication Number Publication Date
GB705979A true GB705979A (en) 1954-03-24

Family

ID=3878497

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3985/52A Expired GB705979A (en) 1951-03-22 1952-02-14 1.4-aralkyl piperazines and process for the preparation thereof

Country Status (1)

Country Link
GB (1) GB705979A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3318876A (en) * 1962-12-11 1967-05-09 Lepetit Spa Substituted piperazines and process for preparing same
US4017614A (en) 1969-12-05 1977-04-12 Henry Wild Compositions for the relief of migraine
EP0159566A1 (en) * 1984-03-30 1985-10-30 Kanebo, Ltd. Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient
WO1994024116A1 (en) * 1993-04-09 1994-10-27 Syntex Pharmaceuticals Limited Heterocyclic derivatives in the treatment of ischaemia and related diseases
WO1995015958A1 (en) * 1993-12-08 1995-06-15 Alcon Laboratories, Inc. Compounds having both potent calcium antagonist and antioxidant activity and use thereof as cytoprotective agents
WO1996028440A1 (en) * 1995-03-15 1996-09-19 Merck & Co., Inc. REDUCTIVE ALKYLATION PROCESS FOR THE PREPARATION N-(2-(R)-HYDROXY-1-(S)-INDANYL)-2(R)-PHENYLMETHYL-4(S)-HYDROXY-5-(1-(4-(3-PYRIDYLMETHYL)-2(S)-N'-(t-BUTYLCARBOXAMIDO)-PIPERAZINYL))-PENTANEAMIDE (=COMPOUND J OR L-735,524)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3318876A (en) * 1962-12-11 1967-05-09 Lepetit Spa Substituted piperazines and process for preparing same
US4017614A (en) 1969-12-05 1977-04-12 Henry Wild Compositions for the relief of migraine
EP0159566A1 (en) * 1984-03-30 1985-10-30 Kanebo, Ltd. Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient
US4663325A (en) * 1984-03-30 1987-05-05 Kanebo Ltd. 1-(2,3,4-tri-methoxybenzyl)-4[bis(4-fluorophenyl)methyl] piperazines are useful for treating cerebrovascular disease
WO1994024116A1 (en) * 1993-04-09 1994-10-27 Syntex Pharmaceuticals Limited Heterocyclic derivatives in the treatment of ischaemia and related diseases
US5428037A (en) * 1993-04-09 1995-06-27 Syntex Pharmaceuticals, Ltd. Heterocyclic derivatives in the treatment of Ischaemia and related diseases
US5545645A (en) * 1993-04-09 1996-08-13 Syntex Pharmaceuticals, Limited Heterocyclic derivatives in the treatment of ischaemia and related diseases
WO1995015958A1 (en) * 1993-12-08 1995-06-15 Alcon Laboratories, Inc. Compounds having both potent calcium antagonist and antioxidant activity and use thereof as cytoprotective agents
US5646149A (en) * 1993-12-08 1997-07-08 Alcon Laboratories, Inc. Compounds having both potent calcium antagonist and antioxidant activity and use thereof as cytoprotective agents
WO1996028440A1 (en) * 1995-03-15 1996-09-19 Merck & Co., Inc. REDUCTIVE ALKYLATION PROCESS FOR THE PREPARATION N-(2-(R)-HYDROXY-1-(S)-INDANYL)-2(R)-PHENYLMETHYL-4(S)-HYDROXY-5-(1-(4-(3-PYRIDYLMETHYL)-2(S)-N'-(t-BUTYLCARBOXAMIDO)-PIPERAZINYL))-PENTANEAMIDE (=COMPOUND J OR L-735,524)
EA000635B1 (en) * 1995-03-15 1999-12-29 Мерк Энд Ко., Инк. Reductive alkylation process for the preparation n-(2-(r)-hydroxy-1-(s)-indanyl)-2(r)-phenylmethyl-4(s)-hydroxy-5-(1-(4-(3-pyridylmethyl)-2(s)-n'-(t-butylcarboxamido)-piperazinyl))-pentaneamide (=compound j or l-735,524)

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