ECSP066740A - ß-HYDROXI OPTICALLY ACTIVE HETEROAROMATIC ESTERS, PROCESSES FOR PREPARATION FROM ß-CETO ESTERS AND PROCESSES FOR THE PREPARATION OF SUCH ß-CETO ESTERS - Google Patents

ß-HYDROXI OPTICALLY ACTIVE HETEROAROMATIC ESTERS, PROCESSES FOR PREPARATION FROM ß-CETO ESTERS AND PROCESSES FOR THE PREPARATION OF SUCH ß-CETO ESTERS

Info

Publication number
ECSP066740A
ECSP066740A EC2006006740A ECSP066740A ECSP066740A EC SP066740 A ECSP066740 A EC SP066740A EC 2006006740 A EC2006006740 A EC 2006006740A EC SP066740 A ECSP066740 A EC SP066740A EC SP066740 A ECSP066740 A EC SP066740A
Authority
EC
Ecuador
Prior art keywords
esters
processes
ceto
heteroaromatic
preparation
Prior art date
Application number
EC2006006740A
Other languages
Spanish (es)
Inventor
Ulrich Klar
Johannes Platzek
Original Assignee
Schering Akti Engesellschaft
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 Schering Akti Engesellschaft filed Critical Schering Akti Engesellschaft
Publication of ECSP066740A publication Critical patent/ECSP066740A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
    • C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
    • C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/12—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D215/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
    • C07D277/62—Benzothiazoles
    • C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
    • 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
    • C12P17/10—Nitrogen as only ring hetero atom
    • C12P17/12—Nitrogen as only ring hetero atom containing a six-membered hetero ring
    • 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
    • C12P17/14—Nitrogen or oxygen as hetero atom and at least one other diverse hetero ring atom in the same ring

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Microbiology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • General Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Genetics & Genomics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

La presente invención se refiere a ésteres ß-hidroxi heteroaromáticos ópticamente activos de fórmula (I) de utilidad en la síntesis de derivados de epotilona, beta-ceto ésteres de fórmula (IV) utilizados para producir estos intermediarios por hidrogenación asimétrica con un catalizador metálico quiral o una reducción microbiológica o enzimática, así como los procesos para su producción (I), en donde: A es un residuo heteroaromático bicíclico de fórmula (A), en donde el término "heteroaromático" se refiere a un anillo heteroaromático de 5 ó 6 miembros que contiene hasta 2 heteroátomos seleccionados entre oxígeno, nitrógeno o azufre, opcionalmente sustituido con uno o dos sustituyentes seleccionados entre alquilo, hidroxialquilo opcionalmente protegido, halo-alquilo, halógeno o CN, y R es una cadena de alquilo de cadena lineal o ramificada, opcionalmente saturada, que contiene opcionalmente 1-3 átomos de oxígeno; un residuo fenilo; ciclohexilo; o bencilo (IV).The present invention relates to optically active β-hydroxy heteroaromatic esters of formula (I) useful in the synthesis of epothilone derivatives, beta-keto esters of formula (IV) used to produce these intermediates by asymmetric hydrogenation with a chiral metal catalyst or a microbiological or enzymatic reduction, as well as the processes for its production (I), wherein: A is a bicyclic heteroaromatic residue of formula (A), wherein the term "heteroaromatic" refers to a heteroaromatic ring of 5 or 6 members containing up to 2 heteroatoms selected from oxygen, nitrogen or sulfur, optionally substituted with one or two substituents selected from alkyl, optionally protected hydroxyalkyl, halo-alkyl, halogen or CN, and R is a straight or branched chain alkyl chain, optionally saturated, optionally containing 1-3 oxygen atoms; a phenyl residue; cyclohexyl; or benzyl (IV).

EC2006006740A 2003-12-31 2006-07-31 ß-HYDROXI OPTICALLY ACTIVE HETEROAROMATIC ESTERS, PROCESSES FOR PREPARATION FROM ß-CETO ESTERS AND PROCESSES FOR THE PREPARATION OF SUCH ß-CETO ESTERS ECSP066740A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10361794A DE10361794B3 (en) 2003-12-31 2003-12-31 Optically active heteroaromatic β-hydroxy esters and processes for their preparation and their use as intermediates in the epothilone total synthesis

Publications (1)

Publication Number Publication Date
ECSP066740A true ECSP066740A (en) 2006-10-31

Family

ID=34716267

Family Applications (1)

Application Number Title Priority Date Filing Date
EC2006006740A ECSP066740A (en) 2003-12-31 2006-07-31 ß-HYDROXI OPTICALLY ACTIVE HETEROAROMATIC ESTERS, PROCESSES FOR PREPARATION FROM ß-CETO ESTERS AND PROCESSES FOR THE PREPARATION OF SUCH ß-CETO ESTERS

Country Status (17)

Country Link
EP (1) EP2113031A1 (en)
JP (1) JP2007516999A (en)
KR (1) KR20070029641A (en)
CN (1) CN100510098C (en)
AU (1) AU2004309076A1 (en)
BR (1) BRPI0418254A (en)
CA (1) CA2546981A1 (en)
CR (1) CR8492A (en)
DE (1) DE10361794B3 (en)
EC (1) ECSP066740A (en)
HK (1) HK1097000A1 (en)
IL (1) IL175908A0 (en)
MX (1) MXPA06007564A (en)
NO (1) NO20063477L (en)
RU (1) RU2006127553A (en)
WO (1) WO2005064006A1 (en)
ZA (1) ZA200606293B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104328152A (en) * 2014-10-13 2015-02-04 青岛科技大学 Method for catalytically producing cyclohexylidene enol by utilizing candida utilis
CN108118004B (en) * 2017-12-15 2021-06-25 北京工商大学 Application of pichia stipitis in preventing and treating postharvest diseases of fruits
CN110283733B (en) * 2019-06-20 2020-10-27 浙江工业大学 Tupistra yeast ZJPH1807 and application thereof

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU7257096A (en) * 1995-10-04 1997-04-28 Fmc Corporation Herbicidal 6-heterocyclic indazole derivatives
US5942644A (en) * 1997-05-27 1999-08-24 Biocatalytics, Inc. Precursors for the production of chiral vicinal aminoalcohols
US6211412B1 (en) * 1999-03-29 2001-04-03 The University Of Kansas Synthesis of epothilones
PE20010116A1 (en) * 1999-04-30 2001-02-15 Schering Ag 6-ALKENYL-, 6-ALKINYL- AND 6-EPOXY-EPOTILONE DERIVATIVES, PROCEDURES FOR THEIR PREPARATION
JP2001213874A (en) * 1999-07-22 2001-08-07 Mercian Corp Production of isocoumarin derivative and intermediate therefor
DE10041470A1 (en) * 2000-08-18 2002-02-28 Schering Ag New 6-substituted 12,13-(cyclopropyl or azacyclopropyl)-epothilone derivatives, useful as cell division regulators for treating e.g. malignant tumors, psoriasis or arthritis
WO2003029195A1 (en) * 2001-09-28 2003-04-10 Sumika Fine Chemicals Co., Ltd. Intermediates for epothilone derivative and process for producing these
JP4432315B2 (en) * 2002-03-19 2010-03-17 三菱化学株式会社 Process for producing optically active 3-hydroxy-3- (2'-thienyl) propionic acid ester derivative

Also Published As

Publication number Publication date
HK1097000A1 (en) 2007-06-15
JP2007516999A (en) 2007-06-28
CN100510098C (en) 2009-07-08
CN1902322A (en) 2007-01-24
RU2006127553A (en) 2008-02-10
MXPA06007564A (en) 2006-12-14
ZA200606293B (en) 2009-08-26
DE10361794B3 (en) 2005-10-06
IL175908A0 (en) 2006-10-05
BRPI0418254A (en) 2007-04-17
AU2004309076A1 (en) 2005-07-14
NO20063477L (en) 2006-08-23
CA2546981A1 (en) 2005-07-14
WO2005064006A1 (en) 2005-07-14
EP2113031A1 (en) 2009-11-04
CR8492A (en) 2007-03-08
KR20070029641A (en) 2007-03-14

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