WO1996011173A3 - Racemisation of precursors to levobupivacaine and analogues thereof - Google Patents

Racemisation of precursors to levobupivacaine and analogues thereof Download PDF

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Publication number
WO1996011173A3
WO1996011173A3 PCT/GB1995/002383 GB9502383W WO9611173A3 WO 1996011173 A3 WO1996011173 A3 WO 1996011173A3 GB 9502383 W GB9502383 W GB 9502383W WO 9611173 A3 WO9611173 A3 WO 9611173A3
Authority
WO
WIPO (PCT)
Prior art keywords
racemisation
acid
optically
levobupivacaine
analogues
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
PCT/GB1995/002383
Other languages
French (fr)
Other versions
WO1996011173A2 (en
Inventor
Ulrich Conrad Dyer
Raymond Mccague
Martin Woods
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.)
Chirotech Technology Ltd
Original Assignee
Chiroscience 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
Priority claimed from GB9420245A external-priority patent/GB9420245D0/en
Priority claimed from GBGB9504924.3A external-priority patent/GB9504924D0/en
Priority to EP95933510A priority Critical patent/EP0784603B1/en
Priority to AT95933510T priority patent/ATE238256T1/en
Priority to MX9702483A priority patent/MX9702483A/en
Priority to AU36140/95A priority patent/AU695740B2/en
Application filed by Chiroscience Ltd filed Critical Chiroscience Ltd
Priority to CA002201780A priority patent/CA2201780C/en
Priority to DE69530499T priority patent/DE69530499T2/en
Priority to JP8512431A priority patent/JPH11510471A/en
Priority to DK95933510T priority patent/DK0784603T3/en
Publication of WO1996011173A2 publication Critical patent/WO1996011173A2/en
Publication of WO1996011173A3 publication Critical patent/WO1996011173A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B55/00—Racemisation; Complete or partial inversion
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Hydrogenated Pyridines (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

A process for the preparation of optically-enriched pipecolic acid as a salt with an optically-active acid, comprises asymmetric transformation of pipecolic acid, as a racemic mixture or a mixture enriched in the opposite enantiomer from that desired, with the optically-active acid in a solvent comprising an acid that causes racemisation, in the absence of aldehyde.
PCT/GB1995/002383 1994-10-07 1995-10-09 Racemisation of precursors to levobupivacaine and analogues thereof Ceased WO1996011173A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DK95933510T DK0784603T3 (en) 1994-10-07 1995-10-09 Racemization of precursors of levobupivacaine and analogous precursors thereof
JP8512431A JPH11510471A (en) 1994-10-07 1995-10-09 Racemization of levobupivacaine and its precursors
AT95933510T ATE238256T1 (en) 1994-10-07 1995-10-09 RACEMIZATION OF LEVOBUPIVACAINE PRECURSORS AND THEIR ANALOGUES
MX9702483A MX9702483A (en) 1994-10-07 1995-10-09 Racemisation of precursors to levobupivacaine and analogues thereof.
AU36140/95A AU695740B2 (en) 1994-10-07 1995-10-09 Racemisation of precursors to levobupivacaine and analogues thereof
EP95933510A EP0784603B1 (en) 1994-10-07 1995-10-09 Racemisation of precursors to levobupivacaine and analogues thereof
CA002201780A CA2201780C (en) 1994-10-07 1995-10-09 Racemisation of precursors to levobupivacaine and analogues thereof
DE69530499T DE69530499T2 (en) 1994-10-07 1995-10-09 RACEMIZATION OF LEVOBUPIVACAINE PRECURSORS AND THEIR ANALOGS

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
GB9420245A GB9420245D0 (en) 1994-10-07 1994-10-07 Racemisation
GB9420245.4 1994-10-07
GBGB9504924.3A GB9504924D0 (en) 1995-03-10 1995-03-10 Racemisation
GB9504924.3 1995-03-10

Publications (2)

Publication Number Publication Date
WO1996011173A2 WO1996011173A2 (en) 1996-04-18
WO1996011173A3 true WO1996011173A3 (en) 1996-07-04

Family

ID=26305756

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/GB1995/002383 Ceased WO1996011173A2 (en) 1994-10-07 1995-10-09 Racemisation of precursors to levobupivacaine and analogues thereof

Country Status (11)

Country Link
EP (1) EP0784603B1 (en)
JP (1) JPH11510471A (en)
AT (1) ATE238256T1 (en)
AU (1) AU695740B2 (en)
CA (1) CA2201780C (en)
DE (1) DE69530499T2 (en)
DK (1) DK0784603T3 (en)
ES (1) ES2196081T3 (en)
MX (1) MX9702483A (en)
PT (1) PT784603E (en)
WO (1) WO1996011173A2 (en)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2074022A5 (en) * 1969-12-20 1971-10-01 Dynamit Nobel Ag
EP0137371A2 (en) * 1983-09-27 1985-04-17 Hoechst Aktiengesellschaft Process for the racemisation of optically active aminoacids
EP0173921A1 (en) * 1984-08-30 1986-03-12 Beecham Group Plc Process for the racemization of an alpha-amino acid
EP0175840A2 (en) * 1984-09-25 1986-04-02 Degussa Aktiengesellschaft Racemisation process of N-acetyl-D(L)-alpha-amino-carboxylic-acids

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2074022A5 (en) * 1969-12-20 1971-10-01 Dynamit Nobel Ag
EP0137371A2 (en) * 1983-09-27 1985-04-17 Hoechst Aktiengesellschaft Process for the racemisation of optically active aminoacids
EP0173921A1 (en) * 1984-08-30 1986-03-12 Beecham Group Plc Process for the racemization of an alpha-amino acid
EP0175840A2 (en) * 1984-09-25 1986-04-02 Degussa Aktiengesellschaft Racemisation process of N-acetyl-D(L)-alpha-amino-carboxylic-acids

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
C. HONGO ET. AL.: "Asymmetric Transformation of N-Acyl-DL-Amino Acids.", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, vol. 54, no. 11, TOKYO, JP, pages 3286 - 90 *
H. K. CHENAULT ET. AL.: "Kinetic Resolution of Unnatural and Rarely Occurring Amino Acids: Enantioselective Hydrolysis of N-acyl Amino Acids Catalysed by Acylase I.", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 111, no. 16, 2 August 1989 (1989-08-02), WASHINGTON DC, US, pages 6354 - 64 *

Also Published As

Publication number Publication date
AU695740B2 (en) 1998-08-20
DE69530499T2 (en) 2004-01-08
EP0784603B1 (en) 2003-04-23
EP0784603A2 (en) 1997-07-23
PT784603E (en) 2003-08-29
DK0784603T3 (en) 2003-08-18
AU3614095A (en) 1996-05-02
CA2201780A1 (en) 1996-04-18
JPH11510471A (en) 1999-09-14
CA2201780C (en) 2007-01-09
ES2196081T3 (en) 2003-12-16
WO1996011173A2 (en) 1996-04-18
DE69530499D1 (en) 2003-05-28
ATE238256T1 (en) 2003-05-15
MX9702483A (en) 1998-04-30

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