HUP9801083A2 - Eljárás (1S,4R)- vagy (1R,4S)-4-[(2-amino-6-klór-9H-purin)-9-il]-2-ciklopentén-1-metanol előállítására - Google Patents

Eljárás (1S,4R)- vagy (1R,4S)-4-[(2-amino-6-klór-9H-purin)-9-il]-2-ciklopentén-1-metanol előállítására

Info

Publication number
HUP9801083A2
HUP9801083A2 HU9801083A HUP9801083A HUP9801083A2 HU P9801083 A2 HUP9801083 A2 HU P9801083A2 HU 9801083 A HU9801083 A HU 9801083A HU P9801083 A HUP9801083 A HU P9801083A HU P9801083 A2 HUP9801083 A2 HU P9801083A2
Authority
HU
Hungary
Prior art keywords
amino
compounds
cyclopentene
chloro
formula
Prior art date
Application number
HU9801083A
Other languages
English (en)
Inventor
Christine Bernegger
Olwen Mary Birch
Pierre Bossard
Walter Brieden
Frank Brux
Kurt Burgdorf
Laurent Duc
Kay-Sara Etter
John Gordon
Yves Guggisberg
Colm O'murchu
Eva Maria Urban
Original Assignee
Lonza Ag.
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 Lonza Ag. filed Critical Lonza Ag.
Publication of HU9801083D0 publication Critical patent/HU9801083D0/hu
Publication of HUP9801083A2 publication Critical patent/HUP9801083A2/hu
Publication of HUP9801083A3 publication Critical patent/HUP9801083A3/hu
Publication of HU226327B1 publication Critical patent/HU226327B1/hu

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
    • C07D473/32—Nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/23—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/94—[b, c]- or [b, d]-condensed containing carbocyclic rings other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D473/00—Heterocyclic compounds containing purine ring systems
    • C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/001—Amines; Imines
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P13/00—Preparation of nitrogen-containing organic compounds
    • C12P13/02—Amides, e.g. chloramphenicol or polyamides; Imides or polyimides; Urethanes, i.e. compounds comprising N-C=O structural element or polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
    • C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
    • C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
    • C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
    • C12P17/182—Heterocyclic compounds containing nitrogen atoms as the only ring heteroatoms in the condensed system
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/10—Systems containing only non-condensed rings with a five-membered ring the ring being unsaturated

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Genetics & Genomics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Microbiology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Micro-Organisms Or Cultivation Processes Thereof (AREA)
  • Indole Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

A találmány tárgyát eljárás képezi az (I) vagy (II) képletű (1S,4R)-vagy (1R,4S)-4-(2-aminő-6-klór-9H-pűrin-9-il)-2-ciklőpentén-1-metanőlelőállítására. Ezen vegyületeket őly módőn állítják elő, hőgy (+)-2-azabiciklő[2.2.1]hept-5-én-3-őnt (IV) általánős képletű (+)-2-azabiciklő[2.2.1]-hept-5-én-3-őn-származékká acilezik, ahől aképletben R1 jelentése 1-4 szénatőmős alkil-, 1-4 szénatőmős alkőxi-,aril- vagy aril-őxi-csőpőrt; - majd a kapőtt vegyületet (V) általánősképletű ciklőpenténszármazékká redűkálják; - majd a kapőttvegyületeket egy N-acetilaminő-alkőhől-hidrőláz hatású enzimmikrőőrganizműsának segítségével vagy egy penicillin G-acilázsegítségével (VI) vagy (VII) képletű vegyületté alakítják; - majd akapőtt vegyületetet N-(2-aminő-4,6-diklór-pirimidin)-5-il-főrmamiddal(1S,4R)- vagy (1R,4S)-4-[(2-aminő-6-klór-5-főrmamidő-4-pirimidinil)-aminő]-2-ciklőpentén-1-metanőllá alakítják; - majd az így kapőttvegyületeket (I) vagy (II) képletű vegyületekké ciklizálják. Atalálmány szerinti eljárással kapőtt vegyületek közbenső termékként 2-aminő-pűrin-nűkleőzidők előállításáhőz alkalmazhatók. ŕ
HU9801083A 1997-05-13 1998-05-13 Process for producing (1s,4r)- or (1r,4s)-4-(2-amino-6-chloro-9h-purin-9-yl)-2-cyclopentene-1-methanol HU226327B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH111697 1997-05-13
CH274097 1997-11-27

Publications (4)

Publication Number Publication Date
HU9801083D0 HU9801083D0 (en) 1998-07-28
HUP9801083A2 true HUP9801083A2 (hu) 1999-11-29
HUP9801083A3 HUP9801083A3 (en) 2001-09-28
HU226327B1 HU226327B1 (en) 2008-08-28

Family

ID=25686703

Family Applications (1)

Application Number Title Priority Date Filing Date
HU9801083A HU226327B1 (en) 1997-05-13 1998-05-13 Process for producing (1s,4r)- or (1r,4s)-4-(2-amino-6-chloro-9h-purin-9-yl)-2-cyclopentene-1-methanol

Country Status (17)

Country Link
US (4) US6156893A (hu)
EP (2) EP1502914A1 (hu)
JP (3) JP4540136B2 (hu)
KR (2) KR100577886B1 (hu)
CN (2) CN1302116C (hu)
AT (1) ATE275206T1 (hu)
CA (1) CA2237297C (hu)
CZ (3) CZ297887B6 (hu)
DE (1) DE59811884D1 (hu)
DK (1) DK0878548T3 (hu)
ES (1) ES2223095T3 (hu)
HK (1) HK1092782A1 (hu)
HU (1) HU226327B1 (hu)
NO (1) NO324679B1 (hu)
PL (1) PL197848B1 (hu)
PT (1) PT878548E (hu)
SK (3) SK285228B6 (hu)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU677851B2 (en) * 1993-06-21 1997-05-08 Merrell Pharmaceuticals Inc. Novel carbocyclic nucleoside agents useful as selective inhibitors of proinflammatory cytokines
GB9717928D0 (en) * 1997-08-22 1997-10-29 Glaxo Group Ltd Process for the enatioselective hydrolysis of n-derivatised lactams
GB9721780D0 (en) * 1997-10-14 1997-12-10 Glaxo Group Ltd Process for the synthesis of chloropurine intermediates
SK284596B6 (sk) * 1997-11-27 2005-07-01 Lonza Ag Spôsob výroby (1S,4R)- alebo (1R,4S)-4-(2-amino-6-chlór-9-H- purin-9-yl)-2-cyklopentén-1-metanolu alebo jeho solí
ATE253125T1 (de) 1998-12-23 2003-11-15 Lonza Ag Verfahren zur herstellung von optisch aktiven 1- amino-4- (hydroxymethyl)- cyclopent-2- en- derivaten
MXPA06000945A (es) * 2003-07-25 2006-03-30 Prometic Biosciences Inc Preparacion de sales metalicas de acidos grasos de cadena mediana.
DE102005061756B4 (de) * 2005-12-21 2008-01-03 Sanofi-Aventis Deutschland Gmbh Verbessertes Verfahren zur Herstellung von Ramipril
US8236853B1 (en) 2007-12-03 2012-08-07 University Of South Florida Formation of cyclopentene nitro-ester and derivatives
WO2012099904A1 (en) 2011-01-18 2012-07-26 General Atomics Hydrolase enzyme substrates and uses thereof
CN102557990B (zh) * 2011-04-25 2014-06-25 开原亨泰制药股份有限公司 (1s，4r)n-叔丁氧羰基-4-氨基-2-环戊烯-1-羧酸甲酯的制备方法

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4950758A (en) * 1988-01-20 1990-08-21 Regents Of The University Of Minnesota Optically-active isomers of dideoxycarbocyclic nucleosides
US4931559A (en) * 1988-01-20 1990-06-05 Regents Of The University Of Minnesota Optically-active isomers of dideoxycarbocyclic nucleosides
MY104575A (en) * 1989-12-22 1994-04-30 The Wellcome Foundation Ltd Therapeutic nucleosides.
CA2055086A1 (en) * 1991-02-12 1992-08-13 Chikara Kaneko Cyclopentene derivatives and their use
US5200527A (en) * 1991-04-08 1993-04-06 Lonza Ltd. Process for the production of 2-azabicyclo [2.2.1] hept-5-en-3-one
GB9204015D0 (en) * 1992-02-25 1992-04-08 Wellcome Found Therapeutic nucleosides
GB9205071D0 (en) * 1992-03-09 1992-04-22 Wellcome Found Therapeutic nucleosides
GB9217823D0 (en) * 1992-08-21 1992-10-07 Glaxo Group Ltd Chemical process
JPH06116217A (ja) * 1992-10-02 1994-04-26 Kuraray Co Ltd （±）−シス−４−アミノシクロペント−２−エンカルボン酸誘導体の光学分割法
GB9402161D0 (en) * 1994-02-04 1994-03-30 Wellcome Found Chloropyrimidine intermediates
PT904348E (pt) * 1996-05-30 2005-04-29 Lonza Ag Processo para a producao de aminoalcoois e seus derivados
GB9625455D0 (en) * 1996-12-07 1997-01-22 Glaxo Group Ltd Process for resolving mixtures of carbocyclic steroisomers

Also Published As

Publication number Publication date
PT878548E (pt) 2005-01-31
EP1502914A1 (de) 2005-02-02
CZ145898A3 (cs) 1998-12-16
NO324679B1 (no) 2007-12-03
EP0878548B1 (de) 2004-09-01
SK285228B6 (sk) 2006-09-07
JP4540136B2 (ja) 2010-09-08
DE59811884D1 (de) 2004-10-07
CN1515673A (zh) 2004-07-28
CZ297888B6 (cs) 2007-04-18
JPH115793A (ja) 1999-01-12
US6252112B1 (en) 2001-06-26
JP2010106025A (ja) 2010-05-13
HU9801083D0 (en) 1998-07-28
SK285229B6 (sk) 2006-09-07
CN1302116C (zh) 2007-02-28
NO982149L (no) 1998-11-16
KR19980086933A (ko) 1998-12-05
US6262295B1 (en) 2001-07-17
CZ297894B6 (cs) 2007-04-25
ES2223095T3 (es) 2005-02-16
EP0878548A2 (de) 1998-11-18
PL326267A1 (en) 1998-11-23
KR100577886B1 (ko) 2006-08-30
SK284810B6 (sk) 2005-12-01
US6156893A (en) 2000-12-05
DK0878548T3 (da) 2004-12-06
PL197848B1 (pl) 2008-05-30
EP0878548A3 (de) 1999-10-13
SK58998A3 (en) 1998-12-02
CZ297887B6 (cs) 2007-04-18
HK1092782A1 (en) 2007-02-16
CA2237297C (en) 2008-03-11
KR100601764B1 (ko) 2006-07-19
HUP9801083A3 (en) 2001-09-28
CN1115343C (zh) 2003-07-23
HU226327B1 (en) 2008-08-28
CN1201794A (zh) 1998-12-16
CA2237297A1 (en) 1998-11-13
JP2010116397A (ja) 2010-05-27
US6137007A (en) 2000-10-24
ATE275206T1 (de) 2004-09-15
NO982149D0 (no) 1998-05-12

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MM4A Lapse of definitive patent protection due to non-payment of fees