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GB929252A - New 1-(trialkoxy benzyl)-piperazines - Google Patents

New 1-(trialkoxy benzyl)-piperazines

Info

Publication number
GB929252A
GB929252A GB1748061A GB1748061A GB929252A GB 929252 A GB929252 A GB 929252A GB 1748061 A GB1748061 A GB 1748061A GB 1748061 A GB1748061 A GB 1748061A GB 929252 A GB929252 A GB 929252A
Authority
GB
United Kingdom
Prior art keywords
piperazine
chloride
compounds
hydrolysing
reacting
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
GB1748061A
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 GB929252A publication Critical patent/GB929252A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/445—Non condensed piperidines, e.g. piperocaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • 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

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

The invention comprises compounds of general formula <FORM:0929252/IV(a)/1> wherein R1, R2 and R3 each represent an alkyl radical having 1-5 carbon atoms, and their acid addition salts; also processes for their preparation by (1) reacting a trialkoxybenzyl chloride with N-monoformlypiperazine and hydrolysing the product formed, or (2) reducing with excess of lithium aluminium hydride a dry solution in an ether of the amide obtained by reacting a trialkoxy benzoic acid chloride with piperazine, or (3) hydrolysing the product (e.g. N-trimethoxybenzyl-N1-formyl-piperazine) obtained from the condensation of a trialkoxybenzaldehyde in the presence of excess of a reducing agent with a piperazine that is N-monosubstituted by a group removable by hydrolysis. 2,3,4-Trimethoxybenzyl chloride can be prepared by chlormethylation of 1,2,3-trimethoxybenzene or from the alcohol using SOCl2. Pharmaceutical compositions comprise the compounds of general formula above or their acid addition salts, with an inert carrier. A tablet is described. The compounds are vasodilators and adrenolytic and noradrenolytic agents.
GB1748061A 1960-06-30 1961-06-02 New 1-(trialkoxy benzyl)-piperazines Expired GB929252A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR831847A FR805M (en) 1960-06-30 1960-06-30

Publications (1)

Publication Number Publication Date
GB929252A true GB929252A (en) 1963-06-19

Family

ID=8734718

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1748061A Expired GB929252A (en) 1960-06-30 1961-06-02 New 1-(trialkoxy benzyl)-piperazines

Country Status (5)

Country Link
BE (1) BE604839A (en)
CH (1) CH406224A (en)
ES (1) ES268523A1 (en)
FR (1) FR805M (en)
GB (1) GB929252A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0187639A1 (en) * 1985-01-11 1986-07-16 Kanebo, Ltd. Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient
EP0453365A1 (en) * 1990-04-20 1991-10-23 Adir Et Compagnie Process for the preparation of 1-(2,3,4-trimethoxybenzyl) piperazine by reductive amination
EP1195160A1 (en) * 2000-10-05 2002-04-10 USV Ltd. Sustained release trimetazidine pharmaceutical compositions and a method of their preparation
CN100413854C (en) * 2004-06-29 2008-08-27 北京德众万全药物技术开发有限公司 A kind of preparation method of trimetazidine and medicinal salt thereof
RU2340606C1 (en) * 2007-06-19 2008-12-10 Закрытое акционерное общество "Щелково Агрохим" Method of obtaining 1-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride
WO2024218267A2 (en) 2023-04-20 2024-10-24 Les Laboratoires Servier Novel trimetazidine solid phases

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2490963B1 (en) * 1980-09-30 1986-04-18 Science Union & Cie NOVEL THERAPEUTIC COMPOSITION WITH ANTI-ISCHEMIC ACTION CONTAINING TRIMETHOXY 2, 3, 4-BENZYL 1-PIPERAZINE
FR2703048B1 (en) * 1993-03-24 1996-01-05 Adir NOVEL N-BENZYLPIPERAZINE COMPOUNDS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM.
FR2723944B1 (en) * 1994-08-25 1996-09-20 Adir NEW TRIMETAZIDINE SALTS AND THEIR USE IN THERAPEUTICS
FR2757164B1 (en) * 1996-12-16 1999-01-22 Adir NOVEL N-BENZYLPIPERAZINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2805463B1 (en) * 2000-02-25 2003-01-24 Adir USE OF TRIMETAZIDINE FOR THE PRODUCTION OF PHARMACEUTICAL COMPOSITIONS FOR INHIBITING ACYL-CoA ACETYLTRANSFERASE

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0187639A1 (en) * 1985-01-11 1986-07-16 Kanebo, Ltd. Novel piperazine derivatives, processes for production thereof, and pharmaceutical compositions comprising said compounds as active ingredient
EP0453365A1 (en) * 1990-04-20 1991-10-23 Adir Et Compagnie Process for the preparation of 1-(2,3,4-trimethoxybenzyl) piperazine by reductive amination
FR2661176A1 (en) * 1990-04-20 1991-10-25 Adir NOVEL PROCESS FOR THE PREPARATION OF 1- (2,3,4-TRIMETHOXYBENZYL) PIPERAZINE IN REDUCTIVE AMINATION
EP1195160A1 (en) * 2000-10-05 2002-04-10 USV Ltd. Sustained release trimetazidine pharmaceutical compositions and a method of their preparation
CN100413854C (en) * 2004-06-29 2008-08-27 北京德众万全药物技术开发有限公司 A kind of preparation method of trimetazidine and medicinal salt thereof
RU2340606C1 (en) * 2007-06-19 2008-12-10 Закрытое акционерное общество "Щелково Агрохим" Method of obtaining 1-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride
WO2024218267A2 (en) 2023-04-20 2024-10-24 Les Laboratoires Servier Novel trimetazidine solid phases

Also Published As

Publication number Publication date
FR805M (en) 1961-09-01
ES268523A1 (en) 1961-10-16
CH406224A (en) 1966-01-31
BE604839A (en) 1961-10-02
DE1445138A1 (en) 1969-02-20

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