PE20030345A1 - 3,5-DIHYDROXY-2,2-DIMETHYL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES AND A PROCEDURE FOR THEIR PREPARATION - Google Patents

3,5-DIHYDROXY-2,2-DIMETHYL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES AND A PROCEDURE FOR THEIR PREPARATION

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Publication number
PE20030345A1
PE20030345A1 PE2002000704A PE2002000704A PE20030345A1 PE 20030345 A1 PE20030345 A1 PE 20030345A1 PE 2002000704 A PE2002000704 A PE 2002000704A PE 2002000704 A PE2002000704 A PE 2002000704A PE 20030345 A1 PE20030345 A1 PE 20030345A1
Authority
PE
Peru
Prior art keywords
dimethyl
dihydroxy
valeroamides
epotilones
synthesis
Prior art date
Application number
PE2002000704A
Other languages
Spanish (es)
Inventor
Jurgen Westermann
Johannes Platzek
Orlin Petrov
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 PE20030345A1 publication Critical patent/PE20030345A1/en

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    • 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 REFIERE A 3-5-DIHIDROXI-2,2-DIMETIL-VALEROAMIDAS DE FORMULA I ENTRE OTROS COMPUESTOS DONDE R1, R2 PUEDEN SER IGUALES O DIFERENTES Y REPRESENTAN UN GRUPO PROTECTOR DE ALCOHOL TAL COMO BENCILO, 4-METOXIBENCILO, 3,4-DIMETOXIBENCILO, ALILO TRITILO O R1 Y R2 FORMAN UN PUENTE REPRESENTAN UN GRUPO PROTECTOR CETAL; Y ES EL GRUPO -NA1A2 DONDE A1 Y A2 SON ALQUILO C1-C6 COMO METILO, ETILO PROPILO, ARILO, ENTRE OTROS. SON COMPUESTOS PREFERIDOS N,N-DIMETIL-3(S)-3,5-ACETONADIMETILCETAL-2,2-DIMETIL-PENTANAMIDA, N,N-DIMETIL-3(S)-3,5-BENZALDEHIDO-DIMETILACETAL-2,2-DIMETIL-PENTANAMIDA, N,N-DIMETIL-3(S)-3,5-DITERBUTILDIMETILSILILOXIL-2,2-DIMETIL-PENTANAMIDA, ENTRE OTROS. SE REFIERE TAMBIEN A UN PROCEDIMIENTO PARA LA PREPARACION Y COMPUESTOS INTERMEDIOS. LOS COMPUESTOS 3-5-DIHIDROXI-2,2-DIMETIL-VALEROAMIDAS PROTEGIDAS PARA LA SINTESIS DE EPOTILONAS Y DERIVADOSIT REFERS TO 3-5-DIHYDROXY-2,2-DIMETHYL-VALEROAMIDES OF FORMULA I AMONG OTHER COMPOUNDS WHERE R1, R2 MAY BE THE SAME OR DIFFERENT AND REPRESENT A PROTECTIVE GROUP OF ALCOHOL SUCH AS BENZYL, 4-METOXYBENZYL, 3,4- DIMETOXIBENZLO, ALYL TRITILO OR R1 AND R2 FORM A BRIDGE REPRESENT A CETAL PROTECTIVE GROUP; AND IT IS THE -NA1A2 GROUP WHERE A1 AND A2 ARE C1-C6 ALKYL LIKE METHYL, ETHYL PROPYL, ARYL, AMONG OTHERS. PREFERRED COMPOUNDS ARE N, N-DIMETHYL-3 (S) -3,5-ACETONADIMETHYLCETAL-2,2-DIMETHYL-PENTANAMIDE, N, N-DIMETHYL-3 (S) -3,5-BENZALDEHIDO-DIMETHYLACETAL-2,2 -DIMETHYL-PENTANAMIDE, N, N-DIMETHYL-3 (S) -3,5-DITERBUTYLDIMETHYLSILILOXYL-2,2-DIMETHYL-PENTHANAMIDE, AMONG OTHERS. IT ALSO REFERS TO A PROCEDURE FOR THE PREPARATION AND INTERMEDIATE COMPOUNDS. THE COMPOUNDS 3-5-DIHYDROXY-2,2-DIMETHYL-VALEROAMIDAS PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES

PE2002000704A 2001-08-03 2002-08-02 3,5-DIHYDROXY-2,2-DIMETHYL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES AND A PROCEDURE FOR THEIR PREPARATION PE20030345A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE10138348A DE10138348A1 (en) 2001-08-03 2001-08-03 Protected 3,5-dihydroxy-2,2-dimethyl-valeroamides for the synthesis of epothilones and derivatives and methods of preparation and use

Publications (1)

Publication Number Publication Date
PE20030345A1 true PE20030345A1 (en) 2003-04-10

Family

ID=7694415

Family Applications (1)

Application Number Title Priority Date Filing Date
PE2002000704A PE20030345A1 (en) 2001-08-03 2002-08-02 3,5-DIHYDROXY-2,2-DIMETHYL-VALEROAMIDES PROTECTED FOR THE SYNTHESIS OF EPOTILONES AND DERIVATIVES AND A PROCEDURE FOR THEIR PREPARATION

Country Status (16)

Country Link
EP (1) EP1412322A2 (en)
JP (1) JP2004537589A (en)
KR (1) KR20040029394A (en)
CN (2) CN1807403A (en)
AR (1) AR036207A1 (en)
BR (1) BR0211649A (en)
CA (1) CA2456255A1 (en)
DE (1) DE10138348A1 (en)
IL (1) IL160159A0 (en)
MX (1) MXPA04000954A (en)
NO (1) NO20040912L (en)
PE (1) PE20030345A1 (en)
PL (1) PL367430A1 (en)
RU (1) RU2004106530A (en)
WO (1) WO2003014063A2 (en)
ZA (1) ZA200401727B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6867305B2 (en) 1996-12-03 2005-03-15 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto and analogues thereof
CA2273083C (en) 1996-12-03 2012-09-18 Sloan-Kettering Institute For Cancer Research Synthesis of epothilones, intermediates thereto, analogues and uses thereof
WO2003029195A1 (en) 2001-09-28 2003-04-10 Sumika Fine Chemicals Co., Ltd. Intermediates for epothilone derivative and process for producing these
DE10326195A1 (en) 2003-06-07 2004-12-23 Schering Ag Protected 5,7-dihydroxy-4,4-dimethyl-3-oxoheptanoic acid esters and 5,7-dihydroxy-2-alkyl-4,4-dimethyl-3-oxoheptanoic acid esters for the synthesis of epothilones and derivatives and processes for the preparation of these esters
CN110857276B (en) * 2018-08-22 2021-03-02 中国科学院化学研究所 Chiral beta-hydroxy amide compounds and preparation method and application thereof

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
AR036207A1 (en) 2004-08-18
BR0211649A (en) 2004-07-13
WO2003014063A2 (en) 2003-02-20
WO2003014063A3 (en) 2003-05-01
MXPA04000954A (en) 2004-04-20
NO20040912L (en) 2004-03-02
JP2004537589A (en) 2004-12-16
ZA200401727B (en) 2005-04-12
IL160159A0 (en) 2004-07-25
DE10138348A1 (en) 2003-02-27
CA2456255A1 (en) 2003-02-20
CN1807403A (en) 2006-07-26
CN1538952A (en) 2004-10-20
KR20040029394A (en) 2004-04-06
PL367430A1 (en) 2005-02-21
EP1412322A2 (en) 2004-04-28
RU2004106530A (en) 2005-07-27

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