AU2009254959B2 - Processes for the synthesis of levocetirizine and intermediates for use therein - Google Patents

Processes for the synthesis of levocetirizine and intermediates for use therein Download PDF

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Publication number
AU2009254959B2
AU2009254959B2 AU2009254959A AU2009254959A AU2009254959B2 AU 2009254959 B2 AU2009254959 B2 AU 2009254959B2 AU 2009254959 A AU2009254959 A AU 2009254959A AU 2009254959 A AU2009254959 A AU 2009254959A AU 2009254959 B2 AU2009254959 B2 AU 2009254959B2
Authority
AU
Australia
Prior art keywords
compound
formula
levocetirizine
process according
solvent
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.)
Ceased
Application number
AU2009254959A
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English (en)
Other versions
AU2009254959A8 (en
AU2009254959A1 (en
Inventor
Sandip Vasant Chikhalikar
Maruti Ghagare
Rajendra Narayanrao Kankan
Dharmaraj Ramachandra Rao
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.)
Cipla Ltd
Original Assignee
Cipla 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 Cipla Ltd filed Critical Cipla Ltd
Publication of AU2009254959A1 publication Critical patent/AU2009254959A1/en
Publication of AU2009254959A8 publication Critical patent/AU2009254959A8/en
Application granted granted Critical
Publication of AU2009254959B2 publication Critical patent/AU2009254959B2/en
Ceased legal-status Critical Current
Anticipated expiration legal-status Critical

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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
    • C07D295/08—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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/54—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
    • C07C217/58—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms with amino groups and the six-membered aromatic ring, or the condensed ring system containing that ring, bound to the same carbon atom of the carbon chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C07C309/66—Methanesulfonates
    • 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
    • C07D295/088—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 to an acyclic saturated chain

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
AU2009254959A 2008-06-02 2009-06-02 Processes for the synthesis of levocetirizine and intermediates for use therein Ceased AU2009254959B2 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
IN1173/MUM/2008 2008-06-02
IN1173MU2008 2008-06-02
PCT/GB2009/001385 WO2009147389A2 (en) 2008-06-02 2009-06-02 Processes for the synthesis of levocetirizine and intermediates for use therein

Publications (3)

Publication Number Publication Date
AU2009254959A1 AU2009254959A1 (en) 2009-12-10
AU2009254959A8 AU2009254959A8 (en) 2011-01-20
AU2009254959B2 true AU2009254959B2 (en) 2014-01-30

Family

ID=41009315

Family Applications (1)

Application Number Title Priority Date Filing Date
AU2009254959A Ceased AU2009254959B2 (en) 2008-06-02 2009-06-02 Processes for the synthesis of levocetirizine and intermediates for use therein

Country Status (10)

Country Link
US (1) US8350031B2 (enExample)
EP (1) EP2307392A2 (enExample)
JP (1) JP2011523659A (enExample)
KR (1) KR20110022635A (enExample)
CN (1) CN102046612A (enExample)
AU (1) AU2009254959B2 (enExample)
CA (1) CA2724887A1 (enExample)
NZ (1) NZ589492A (enExample)
WO (1) WO2009147389A2 (enExample)
ZA (1) ZA201008223B (enExample)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CA2724887A1 (en) 2008-06-02 2009-12-10 Cipla Limited Processes for the synthesis of levocetirizine and intermediates for use therein
CN103044356A (zh) * 2011-10-13 2013-04-17 湖南九典制药有限公司 合成左西替利嗪的新方法及其关键中间体
CN110988163B (zh) * 2019-11-29 2022-04-19 重庆华邦胜凯制药有限公司 一种hplc法分离测定盐酸左西替利嗪及其基因毒性杂质e的方法
CN111205247B (zh) * 2020-04-22 2020-08-14 湖南九典宏阳制药有限公司 左旋西替利嗪的制备方法

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3790606A (en) * 1970-09-30 1974-02-05 Diamond Shamrock Corp Alkoxylated mannich compositions and derivatives thereof
US5478941A (en) * 1993-03-15 1995-12-26 U C B, S.A. Enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl) sulfonyl]piperazine
JP2002363146A (ja) * 2001-05-31 2002-12-18 Shin Etsu Chem Co Ltd 塩基性化合物、レジスト材料及びパターン形成方法
US6762180B1 (en) * 1999-10-13 2004-07-13 Boehringer Ingelheim Pharma Kg Substituted indolines which inhibit receptor tyrosine kinases
EP1147085B1 (en) * 1999-01-27 2005-11-16 Wyeth Holdings Corporation Alkynyl containing hydroxamic acid derivatives, their preparation and their use as matrix metalloproteinase (mmp) inhibitors / tnf-alpha converting enzyme (tace) inhibitors
WO2007066163A2 (en) * 2005-12-08 2007-06-14 Egis Gyógyszergyár Nyilvanosan Mukodo Reszvenytarsasag Optically active carbamates, process for preparation thereof and use thereof as pharmaceutical intermediates

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2792398A (en) * 1954-12-03 1957-05-14 Miles Lab Piperazine derivatives
NL7306771A (enExample) * 1972-06-02 1973-12-04
NO155805C (no) 1981-02-06 1987-06-10 Ucb Sa Analogifremgangsmaate for fremstilling av terapeutisk virksomme 2-(4-(difenylmethyl)-1-piperazinyl)-eddiksyrer og deres amider og ikke-toksiske salter.
US4656182A (en) 1983-12-06 1987-04-07 Warner-Lambert Company Substituted trans-1,2-diaminocyclohexyl amide compounds
GB8827391D0 (en) 1988-11-23 1988-12-29 Ucb Sa Process for preparation of 2-(2-(4-((4-chlorophenyl)phenylmethyl)-1-pipera-zinyl)ethoxy)-acetic acid & its dihydrochloride
JP4416198B2 (ja) * 1997-12-19 2010-02-17 武田薬品工業株式会社 アニリド誘導体、その製造法および用途
AR035312A1 (es) * 1999-01-27 2004-05-12 Wyeth Corp Compuestos de acido hidroxamico que contienen alquinilo como inhibidores de metaloproteinasa de matriz/tace, composicion farmaceutica que los comprenden y el uso de los mismos para la manufactura de un medicamento
CA2724887A1 (en) 2008-06-02 2009-12-10 Cipla Limited Processes for the synthesis of levocetirizine and intermediates for use therein

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3790606A (en) * 1970-09-30 1974-02-05 Diamond Shamrock Corp Alkoxylated mannich compositions and derivatives thereof
US5478941A (en) * 1993-03-15 1995-12-26 U C B, S.A. Enantiomers of 1-[(4-chlorophenyl)phenylmethyl]-4-[(4-methylphenyl) sulfonyl]piperazine
EP1147085B1 (en) * 1999-01-27 2005-11-16 Wyeth Holdings Corporation Alkynyl containing hydroxamic acid derivatives, their preparation and their use as matrix metalloproteinase (mmp) inhibitors / tnf-alpha converting enzyme (tace) inhibitors
US6762180B1 (en) * 1999-10-13 2004-07-13 Boehringer Ingelheim Pharma Kg Substituted indolines which inhibit receptor tyrosine kinases
JP2002363146A (ja) * 2001-05-31 2002-12-18 Shin Etsu Chem Co Ltd 塩基性化合物、レジスト材料及びパターン形成方法
WO2007066163A2 (en) * 2005-12-08 2007-06-14 Egis Gyógyszergyár Nyilvanosan Mukodo Reszvenytarsasag Optically active carbamates, process for preparation thereof and use thereof as pharmaceutical intermediates

Also Published As

Publication number Publication date
US8350031B2 (en) 2013-01-08
CA2724887A1 (en) 2009-12-10
AU2009254959A8 (en) 2011-01-20
JP2011523659A (ja) 2011-08-18
WO2009147389A3 (en) 2010-07-01
KR20110022635A (ko) 2011-03-07
NZ589492A (en) 2012-06-29
EP2307392A2 (en) 2011-04-13
CN102046612A (zh) 2011-05-04
AU2009254959A1 (en) 2009-12-10
ZA201008223B (en) 2011-08-31
US20110184174A1 (en) 2011-07-28
WO2009147389A2 (en) 2009-12-10
WO2009147389A8 (en) 2010-12-23

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Free format text: IN VOL 24, NO 49, PAGE(S) 5648 UNDER THE HEADING PCT APPLICATIONS THAT HAVE ENTERED THE NATIONAL PHASE - NAME INDEX UNDER THE NAME CIPLA LIMITED, APPLICATION NO. 2009254959, UNDER INID (72) REMOVE CO-INVENTOR CURTIS, PHILIP ANTHONY.

FGA Letters patent sealed or granted (standard patent)
MK14 Patent ceased section 143(a) (annual fees not paid) or expired