ZA200406469B - Stereoselective alkylation of chiral 2-methyl-4-protected piperazines. - Google Patents

Stereoselective alkylation of chiral 2-methyl-4-protected piperazines. Download PDF

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Publication number
ZA200406469B
ZA200406469B ZA200406469A ZA200406469A ZA200406469B ZA 200406469 B ZA200406469 B ZA 200406469B ZA 200406469 A ZA200406469 A ZA 200406469A ZA 200406469 A ZA200406469 A ZA 200406469A ZA 200406469 B ZA200406469 B ZA 200406469B
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South Africa
Prior art keywords
compound
formula
group
alkyl
solvent
Prior art date
Application number
ZA200406469A
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English (en)
Inventor
Wenxue Wu
David J Tsai
Dinesh Gala
Martin Lawrence Schwartz
Xiaoyong Fu
Tiruvettipuram K Thiruvengadam
Hongbiao Liao
David R Andrews
Gary M Lee
Timothy Mcallister
Donal Maloney
Chou-Hang Tann
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Schering Corp
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Application filed by Schering Corp filed Critical Schering Corp
Publication of ZA200406469B publication Critical patent/ZA200406469B/en

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    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • 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
    • C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/51—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition
    • C07C45/511—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups
    • C07C45/512—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by pyrolysis, rearrangement or decomposition involving transformation of singly bound oxygen functional groups to >C = O groups the singly bound functional group being a free hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of 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
    • C07D295/08—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
    • 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
    • C07D295/092—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 with aromatic radicals attached to the chain
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/18—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 acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/192—Radicals derived from carboxylic acids from aromatic carboxylic acids
    • 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
    • C07D295/16—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 acylated on ring nitrogen atoms
    • C07D295/20—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 acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
    • C07D295/205—Radicals derived from carbonic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
ZA200406469A 2002-03-29 2004-08-13 Stereoselective alkylation of chiral 2-methyl-4-protected piperazines. ZA200406469B (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US36870702P 2002-03-29 2002-03-29

Publications (1)

Publication Number Publication Date
ZA200406469B true ZA200406469B (en) 2005-09-20

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Family Applications (1)

Application Number Title Priority Date Filing Date
ZA200406469A ZA200406469B (en) 2002-03-29 2004-08-13 Stereoselective alkylation of chiral 2-methyl-4-protected piperazines.

Country Status (14)

Country Link
US (3) US6872826B2 (zh)
EP (3) EP1490346B1 (zh)
JP (2) JP2005526826A (zh)
CN (2) CN100343240C (zh)
AR (1) AR039196A1 (zh)
AT (1) ATE450520T1 (zh)
AU (1) AU2003239128A1 (zh)
CA (1) CA2480481A1 (zh)
DE (1) DE60330323D1 (zh)
ES (1) ES2335488T3 (zh)
HK (1) HK1067126A1 (zh)
MX (1) MXPA04009414A (zh)
WO (1) WO2003084942A2 (zh)
ZA (1) ZA200406469B (zh)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003264365A1 (en) * 2002-09-05 2004-03-29 Toray Fine Chemicals Co, . Ltd. Process for producing oxycarbonyl-substituted piperazine derivative
JP2004143087A (ja) * 2002-10-24 2004-05-20 Central Glass Co Ltd 光学活性２−アルコキシ−１−（トリフルオロメチル置換フェニル）エタノール誘導体の製造方法
US20090299063A1 (en) * 2005-03-29 2009-12-03 Paul Shapiro Inhibitors for Extracellular Signal-Regulated Kinase Docking Domains and Uses Therefor
JP2007099659A (ja) * 2005-10-03 2007-04-19 Toray Fine Chemicals Co Ltd ピペラジンカルボン酸エステルの製造法
EP2470182B1 (en) 2009-08-24 2014-06-04 Neuralstem, Inc. Synthesis of a neurostimulative piperazine
CN102241611B (zh) * 2011-05-18 2014-02-26 江阴市雪豹精细化工研究所 S（一）对甲基苯磺酰基丙酸乙酯的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5889006A (en) * 1995-02-23 1999-03-30 Schering Corporation Muscarinic antagonists
AU8576098A (en) * 1997-07-25 1999-02-16 Merck & Co., Inc. Cyclic amine modulators of chemokine receptor activity
ATE299865T1 (de) * 1999-05-04 2005-08-15 Schering Corp Piperazinderivate verwendbar als ccr5 antagonisten
US6391865B1 (en) * 1999-05-04 2002-05-21 Schering Corporation Piperazine derivatives useful as CCR5 antagonists
BR0010783A (pt) * 1999-05-21 2002-04-09 Biovitrum Ab Novos compostos, seu uso e preparação
SE0001899D0 (sv) * 2000-05-22 2000-05-22 Pharmacia & Upjohn Ab New compounds
JP4807675B2 (ja) * 2001-02-26 2011-11-02 東レ・ファインケミカル株式会社 高純度ピペラジン誘導体塩酸塩の製造方法

Also Published As

Publication number Publication date
CN101092401A (zh) 2007-12-26
EP2141153A2 (en) 2010-01-06
CA2480481A1 (en) 2003-10-16
EP2141143A3 (en) 2010-05-05
EP2141143A2 (en) 2010-01-06
JP2010111684A (ja) 2010-05-20
WO2003084942A2 (en) 2003-10-16
JP2005526826A (ja) 2005-09-08
EP1490346A2 (en) 2004-12-29
US20100249411A1 (en) 2010-09-30
AR039196A1 (es) 2005-02-09
MXPA04009414A (es) 2005-01-25
US20030208074A1 (en) 2003-11-06
US6872826B2 (en) 2005-03-29
AU2003239128A1 (en) 2003-10-20
ES2335488T3 (es) 2010-03-29
ATE450520T1 (de) 2009-12-15
DE60330323D1 (de) 2010-01-14
CN1642930A (zh) 2005-07-20
EP2141153A3 (en) 2010-05-26
CN100343240C (zh) 2007-10-17
US7745626B2 (en) 2010-06-29
US20050171120A1 (en) 2005-08-04
EP1490346B1 (en) 2009-12-02
HK1067126A1 (en) 2005-04-01
WO2003084942A3 (en) 2004-05-06

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