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AR036207A1 - 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismas - Google Patents

3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismas

Info

Publication number
AR036207A1
AR036207A1 ARP020102940A ARP020102940A AR036207A1 AR 036207 A1 AR036207 A1 AR 036207A1 AR P020102940 A ARP020102940 A AR P020102940A AR P020102940 A ARP020102940 A AR P020102940A AR 036207 A1 AR036207 A1 AR 036207A1
Authority
AR
Argentina
Prior art keywords
compounds
group
preparation
benzyl
formula
Prior art date
Application number
ARP020102940A
Other languages
English (en)
Inventor
Platzek Johannes Dr
Orlin Petrov
Juergen Westermann
Original Assignee
Schering 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 Schering Ag filed Critical Schering Ag
Publication of AR036207A1 publication Critical patent/AR036207A1/es

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
    • 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
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • 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
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/06—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/16—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
    • C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/002—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by oxidation/reduction reactions
    • 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
    • C12P41/00—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture
    • C12P41/003—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions
    • C12P41/004—Processes using enzymes or microorganisms to separate optical isomers from a racemic mixture by ester formation, lactone formation or the inverse reactions by esterification of alcohol- or thiol groups in the enantiomers or the inverse reaction

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

Abstract

Se describen 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas de fórmula general (1) en donde R1, R2 pueden ser iguales o diferentes y representan, independientemente entre sí, un grupo protector de alcohol tal como, bencilo, 4-metoxibencilo, 3,4-dimetoxibencilo, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, alilo, tritilo, o en caso de que R1 y R2 formen un puente, representan un grupo protector cetal tal como, grupo (2); Y representa un grupo -NA1A2, en donde A1 y A2 representan independientemente un radical alquilo C1-6 tal como metilo, etilo, propilo, o un radical arilo o aralquilo tal como fenilo o bencilo, -OH, OMe u -O- bencilo, o representa un resto (3). También se describen antípodas ópticamente puros de los compuestos de fórmula (1), los productos intermedios, ópticamente activos, y compuestos de partida empleados en la preparación de los compuestos de fórmula (1), así como los procedimientos de preparación de todos estos compuestos. También se describe un procedimiento para preparar cetonas de fórmula general (4), donde R1, R2 pueden ser iguales o diferentes y representan independientemente un grupo protector de alcohol tal como, por ejemplo, bencilo, 4-metoxibencilo, 3,4-dimetoxibencilo, THP, TBDMS, TMS, TES, TIP, TBDPS, MEM, MOM, alilo, tritilo, o en caso de que R1 y R2 formen un puente, representan un grupo protector cetal tal como, por ejemplo, grupo (2) y V representa un radical alquilo C1-5 o alquenilo, a partir de compuestos de fórmula (1), ópticamente activos. Asimismo se describe el uso de estos compuestos para la obtención de epotilonas o derivados de epotilonas, en particular para la preparación del fragmento constitutivo (4) en la síntesis total de epotilonas. Los compuestos descriptos más arriba son estables al almacenamiento y pueden ser obtenidos fácilmente a partir de materiales de partida relativamente económicos. En general, son sustancias sólidas cristalinas y pueden purificarse por recristalización. De esta manera se pueden alcanzar elevados rendimientos químicos y ópticos.
ARP020102940A 2001-08-03 2002-08-02 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismas AR036207A1 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10138348A DE10138348A1 (de) 2001-08-03 2001-08-03 Geschützte 3,5-Dihydroxy-2,2-dimethyl-valeroamide für die Synthese von Epothilonen und Derivaten und Verfahren zur Herstellung und die Verwendung

Publications (1)

Publication Number Publication Date
AR036207A1 true AR036207A1 (es) 2004-08-18

Family

ID=7694415

Family Applications (1)

Application Number Title Priority Date Filing Date
ARP020102940A AR036207A1 (es) 2001-08-03 2002-08-02 3,5-dihidroxi-2,2-dimetil-valeroamidas protegidas para la sintesis de epotilonas y derivados, un procedimiento para su preparacion y el empleo de las mismas

Country Status (16)

Country Link
EP (1) EP1412322A2 (es)
JP (1) JP2004537589A (es)
KR (1) KR20040029394A (es)
CN (2) CN1538952A (es)
AR (1) AR036207A1 (es)
BR (1) BR0211649A (es)
CA (1) CA2456255A1 (es)
DE (1) DE10138348A1 (es)
IL (1) IL160159A0 (es)
MX (1) MXPA04000954A (es)
NO (1) NO20040912L (es)
PE (1) PE20030345A1 (es)
PL (1) PL367430A1 (es)
RU (1) RU2004106530A (es)
WO (1) WO2003014063A2 (es)
ZA (1) ZA200401727B (es)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6204388B1 (en) 1996-12-03 2001-03-20 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto and analogues thereof
US6867305B2 (en) 1996-12-03 2005-03-15 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto and analogues thereof
AU756699B2 (en) 1996-12-03 2003-01-23 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto, analogues and uses thereof
WO2003029195A1 (fr) 2001-09-28 2003-04-10 Sumika Fine Chemicals Co., Ltd. Intermediaires pour l'elaboration d'un derive de l'epothilone, et leur procede de production
US6921769B2 (en) 2002-08-23 2005-07-26 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto and analogues thereof
DE10326195A1 (de) * 2003-06-07 2004-12-23 Schering Ag Geschützte 5,7-Dihydroxy-4,4-dimethyl-3-oxoheptansäureester und 5,7-Dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptansäureester für die Synthese von Epothilonen- und Derivaten und Verfahren zur Herstellung dieser Ester
CN110857276B (zh) * 2018-08-22 2021-03-02 中国科学院化学研究所 一类手性β-羟基酰胺类化合物及其制备方法与应用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4824980A (en) * 1988-09-02 1989-04-25 Dow Corning Corporation Process to produce O-silyl O,N-ketene acetals
US6211412B1 (en) * 1999-03-29 2001-04-03 The University Of Kansas Synthesis of epothilones

Also Published As

Publication number Publication date
KR20040029394A (ko) 2004-04-06
ZA200401727B (en) 2005-04-12
WO2003014063A2 (de) 2003-02-20
JP2004537589A (ja) 2004-12-16
RU2004106530A (ru) 2005-07-27
CA2456255A1 (en) 2003-02-20
CN1807403A (zh) 2006-07-26
PE20030345A1 (es) 2003-04-10
DE10138348A1 (de) 2003-02-27
EP1412322A2 (de) 2004-04-28
IL160159A0 (en) 2004-07-25
BR0211649A (pt) 2004-07-13
NO20040912L (no) 2004-03-02
MXPA04000954A (es) 2004-04-20
WO2003014063A3 (de) 2003-05-01
PL367430A1 (en) 2005-02-21
CN1538952A (zh) 2004-10-20

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