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JPS54112896A - Preparation of maytansines - Google Patents

Preparation of maytansines

Info

Publication number
JPS54112896A
JPS54112896AJP1867578AJP1867578AJPS54112896AJP S54112896 AJPS54112896 AJP S54112896AJP 1867578 AJP1867578 AJP 1867578AJP 1867578 AJP1867578 AJP 1867578AJP S54112896 AJPS54112896 AJP S54112896A
Authority
JP
Japan
Prior art keywords
formula
maytansinol
maytansine
prepared
lower alkyl
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.)
Granted
Application number
JP1867578A
Other languages
Japanese (ja)
Other versions
JPS6152835B2 (en
Inventor
Naoto Hashimoto
Toyokazu Kishi
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.)
Takeda Pharmaceutical Co Ltd
Original Assignee
Takeda Chemical Industries 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
Application filed by Takeda Chemical Industries LtdfiledCriticalTakeda Chemical Industries Ltd
Priority to JP1867578ApriorityCriticalpatent/JPS54112896A/en
Priority to US05/886,815prioritypatent/US4137230A/en
Priority to US05/948,895prioritypatent/US4190580A/en
Priority to CH1160678Aprioritypatent/CH637398A5/en
Priority to CA316,118Aprioritypatent/CA1097627A/en
Priority to DE19782849090prioritypatent/DE2849090A1/en
Priority to FR7832040Aprioritypatent/FR2416895A1/en
Priority to DK503978Aprioritypatent/DK503978A/en
Priority to IT29728/78Aprioritypatent/IT1100898B/en
Priority to SE7811689Aprioritypatent/SE441830B/en
Priority to GB7844415Aprioritypatent/GB2009742B/en
Publication of JPS54112896ApublicationCriticalpatent/JPS54112896A/en
Publication of JPS6152835B2publicationCriticalpatent/JPS6152835B2/ja
Grantedlegal-statusCriticalCurrent

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Landscapes

Abstract

PURPOSE:To prepare maytansines having antibiotic and carcinostatic activities, in high yield and at low cost compared with the conventional vegetable extraction process, by the chemical synthesis using maytansinol as a starting material. CONSTITUTION:A maytansine of formula III is prepared by reacting a maytansinol of formula I (R is lower alkyl) with an amino acid derivative of formula II in the presence of a carbodimide of formula R1-N=C=N-R2 (R1,2 are cycloalkyl, lower alkyl, etc. which can convert the carbodiimide bond to a urea bond by the acylation reaction). A novel D-isomer of maytansine III wherein the absolute configuration of the 2'-assymmetric center is D, or a novel mixture of D and L-isomers can be prepared by the method of this invention.
JP1867578A1977-11-141978-02-20Preparation of maytansinesGrantedJPS54112896A (en)

Priority Applications (11)

Application NumberPriority DateFiling DateTitle
JP1867578AJPS54112896A (en)1978-02-201978-02-20Preparation of maytansines
US05/886,815US4137230A (en)1977-11-141978-03-15Method for the production of maytansinoids
US05/948,895US4190580A (en)1977-11-141978-10-05Optically active maytansinoids and maytansinoid production method
CH1160678ACH637398A5 (en)1977-11-141978-11-10 METHOD FOR PRODUCING MAYTANSINOID COMPOUNDS.
CA316,118ACA1097627A (en)1977-11-141978-11-10Method for the production of maytansinoids
DE19782849090DE2849090A1 (en)1977-11-141978-11-11 METHOD FOR PRODUCING MAYTANSINOID COMPOUNDS
FR7832040AFR2416895A1 (en)1977-11-141978-11-13 MAYTANSINOIDS PRODUCTION PROCESS
DK503978ADK503978A (en)1977-11-141978-11-13 PROCEDURE FOR THE PREPARATION OF MAYTANSINOIDS
IT29728/78AIT1100898B (en)1977-11-141978-11-13 PROCEDURE FOR PRODUCING MAITANSINOID COMPOUNDS
SE7811689ASE441830B (en)1977-11-141978-11-13 PROCEDURE FOR PREPARING MAYTANSINOIDS
GB7844415AGB2009742B (en)1977-11-141978-11-14Process for the preparation of maytansinoids and d-maytansinoids

Applications Claiming Priority (1)

Application NumberPriority DateFiling DateTitle
JP1867578AJPS54112896A (en)1978-02-201978-02-20Preparation of maytansines

Publications (2)

Publication NumberPublication Date
JPS54112896Atrue JPS54112896A (en)1979-09-04
JPS6152835B2 JPS6152835B2 (en)1986-11-14

Family

ID=11978169

Family Applications (1)

Application NumberTitlePriority DateFiling Date
JP1867578AGrantedJPS54112896A (en)1977-11-141978-02-20Preparation of maytansines

Country Status (1)

CountryLink
JP (1)JPS54112896A (en)

Also Published As

Publication numberPublication date
JPS6152835B2 (en)1986-11-14

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