YU74101A - Novel synthesis and crystallization of piperazine ring-containing compounds - Google Patents

Novel synthesis and crystallization of piperazine ring-containing compounds

Info

Publication number
YU74101A
YU74101A YU74101A YUP74101A YU74101A YU 74101 A YU74101 A YU 74101A YU 74101 A YU74101 A YU 74101A YU P74101 A YUP74101 A YU P74101A YU 74101 A YU74101 A YU 74101A
Authority
YU
Yugoslavia
Prior art keywords
piperazine
methyl
phenyl
mirtazapine
present
Prior art date
Application number
YU74101A
Other languages
Serbo-Croatian (sh)
Inventor
Claude Singer
Anita Liberman
Nina Finkelstein
Original Assignee
Teva Pharmaceutical Industries 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 Teva Pharmaceutical Industries Ltd. filed Critical Teva Pharmaceutical Industries Ltd.
Publication of YU74101A publication Critical patent/YU74101A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/24—Antidepressants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
    • C07D471/14—Ortho-condensed systems

Abstract

Predmetni pronalazak je usmeren na postupke za pripremanje jedinjenja koja sadrže prsten piperazina, a posebno na mirtazapin. Prema predmetnom pronalasku, intermedijer mirtazapina, 1-(3-karboksipiridil-2)-4-metil-2-fenil-piperazin se dobija hidrolizom 1-(3-cijanopiridil-2)-4-metil-2-fenil-piperazina pomoću baze, pri čemu je baza prisutna u odnosu koji se kreće do oko 12 molova baze na jedan mol 1-(3-cijanopiridil-2)-4-metil-2-fenil-piperazina. Intermedijer mirtazapina, 1-(3-karboksipiridil-2)-4-metil-2-fenil-piperazin, može se dobiti hidrolizom 1-(3-cijanopiridil-2)-4-metil-2-fenil-piperazina pomoću kalijum-hidroksida pri temperaturi od oko bar 130В°C. Postupak predmetnog pronalaska takodje obuhvata reakciju 2-amino-3-hidroksimetil piridina sa N-metil-1-fenil-2,2'-iminodietil hloridom, kako bi se dobio 1-(3-hidroksimetilpiridil-2)-4-metil-2-fenil piperazin, kao i dodavanje sumporne kiseline 1-(3-hidroksimetilpiridil-2)-4-metil-2-fenil piperazinu, kako bi se dobio mirtazapin. Predmetni pronalazak se takodje odnosi na nove postupke za rekristalizaciju mirtazapina iz sirovog mirtazapina.The present invention is directed to processes for the preparation of compounds containing a piperazine ring, and in particular to mirtazapine. According to the present invention, mirtazapine intermediate, 1- (3-carboxypyridyl-2) -4-methyl-2-phenyl-piperazine is obtained by hydrolysis of 1- (3-cyanopyridyl-2) -4-methyl-2-phenyl-piperazine using a base , wherein the base is present in a ratio ranging to about 12 moles of base per mole of 1- (3-cyanopyridyl-2) -4-methyl-2-phenyl-piperazine. The mirtazapine intermediate, 1- (3-carboxypyridyl-2) -4-methyl-2-phenyl-piperazine, can be obtained by hydrolysis of 1- (3-cyanopyridyl-2) -4-methyl-2-phenyl-piperazine using potassium hydroxide at a temperature of about at least 130V ° C. The process of the present invention also comprises reacting 2-amino-3-hydroxymethyl pyridine with N-methyl-1-phenyl-2,2'-iminodiethyl chloride to give 1- (3-hydroxymethylpyridyl-2) -4-methyl-2 -phenyl piperazine, as well as adding sulfuric acid to 1- (3-hydroxymethylpyridyl-2) -4-methyl-2-phenyl piperazine, to give mirtazapine. The present invention also relates to novel processes for recrystallization of mirtazapine from crude mirtazapine.

YU74101A 1999-04-19 2000-04-18 Novel synthesis and crystallization of piperazine ring-containing compounds YU74101A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US13004799P 1999-04-19 1999-04-19

Publications (1)

Publication Number Publication Date
YU74101A true YU74101A (en) 2004-09-03

Family

ID=22442814

Family Applications (1)

Application Number Title Priority Date Filing Date
YU74101A YU74101A (en) 1999-04-19 2000-04-18 Novel synthesis and crystallization of piperazine ring-containing compounds

Country Status (16)

Country Link
JP (1) JP2004500324A (en)
KR (1) KR20020019902A (en)
CN (4) CN1680365A (en)
CA (1) CA2368815A1 (en)
CZ (1) CZ20013658A3 (en)
HK (1) HK1044116A1 (en)
HR (1) HRP20010747A2 (en)
HU (1) HUP0200839A3 (en)
IL (1) IL146023A0 (en)
PL (1) PL366289A1 (en)
RU (1) RU2001128229A (en)
SK (1) SK14672001A3 (en)
TR (1) TR200103028T2 (en)
WO (1) WO2000062782A1 (en)
YU (1) YU74101A (en)
ZA (1) ZA200108220B (en)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU6019900A (en) 1999-11-24 2001-06-04 Sumika Fine Chemicals Co., Ltd. Anhydrous mirtazapine crystals and process for producing the same
AU6474200A (en) * 1999-12-13 2001-06-18 Sumika Fine Chemicals Co., Ltd. Process for the preparation of a pyridinemethanol compound
US6660730B2 (en) * 2000-11-27 2003-12-09 Sumika Fine Chemicals Co., Ltd. Anhydrous mirtazapine and process for preparing the same
UA83666C2 (en) 2003-07-10 2008-08-11 Н.В. Органон Method for the preparation of enantiomerically pure mirtazapine
ES2246161B1 (en) * 2004-07-22 2007-04-01 Medichem, S.A. IMPROVED PROCESS FOR THE MANUFACTURE OF MIRTAZAPINE.
JP4848704B2 (en) * 2004-08-24 2011-12-28 住友化学株式会社 Process for producing 2- (4-methyl-2-phenylpiperazin-1-yl) -3-cyanopyridine
JP5192707B2 (en) 2007-03-22 2013-05-08 住友化学株式会社 Manufacturing method of mirtazapine
EP2146993B1 (en) 2007-04-11 2015-08-05 Merck Sharp & Dohme B.V. A method for the preparation of mirtazapine
US7994314B2 (en) 2007-04-11 2011-08-09 N.V. Organon Method for the preparation of an enantiomerically pure benzazepine
KR101485418B1 (en) 2013-05-29 2015-01-26 주식회사 메디켐코리아 A synthetic method of high purity mirtazapine
JP2017088564A (en) * 2015-11-13 2017-05-25 株式会社トクヤマ Manufacturing method of mirtazapine
JP6571497B2 (en) * 2015-11-13 2019-09-04 株式会社トクヤマ Manufacturing method of mirtazapine
CN108191873B (en) * 2018-01-08 2021-09-24 山东省食品药品检验研究院 Method for purifying mianserin hydrochloride

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL189199C (en) * 1975-04-05 1993-02-01 Akzo Nv PROCESS FOR THE PREPARATION OF PHARMACEUTICAL PREPARATIONS WITH ACTION ON THE CENTRAL NERVOUS SYSTEM BASED ON BENZ (ARYL) AZEPINE DERIVATIVES, THE PHARMACEUTICAL PREPARATIONS OBTAINED, AND METHOD FOR PREPARING THE PRODUCT TO BE USED.

Also Published As

Publication number Publication date
PL366289A1 (en) 2005-01-24
HRP20010747A2 (en) 2002-12-31
HUP0200839A2 (en) 2002-08-28
CZ20013658A3 (en) 2002-08-14
TR200103028T2 (en) 2002-01-21
CN1680374A (en) 2005-10-12
KR20020019902A (en) 2002-03-13
WO2000062782A1 (en) 2000-10-26
CN1680365A (en) 2005-10-12
JP2004500324A (en) 2004-01-08
CN1356903A (en) 2002-07-03
CA2368815A1 (en) 2000-10-26
HUP0200839A3 (en) 2003-05-28
IL146023A0 (en) 2002-07-25
ZA200108220B (en) 2006-02-26
SK14672001A3 (en) 2002-11-06
RU2001128229A (en) 2003-07-10
CN1679586A (en) 2005-10-12
HK1044116A1 (en) 2002-10-11

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