RU97114134A - METHOD FOR PRODUCING 4,10-DIACETOXY-2α-BENZOILOXY-5β, 20-EPOXY-1,7β-DIOXY-9-OXO-TAX-11-EN-13α-IL (2R, 3S) -3-BENZOILAMINO-2 - Oxy-3-phenylpropionate - Google Patents

METHOD FOR PRODUCING 4,10-DIACETOXY-2α-BENZOILOXY-5β, 20-EPOXY-1,7β-DIOXY-9-OXO-TAX-11-EN-13α-IL (2R, 3S) -3-BENZOILAMINO-2 - Oxy-3-phenylpropionate

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Publication number
RU97114134A
RU97114134A RU97114134/04A RU97114134A RU97114134A RU 97114134 A RU97114134 A RU 97114134A RU 97114134/04 A RU97114134/04 A RU 97114134/04A RU 97114134 A RU97114134 A RU 97114134A RU 97114134 A RU97114134 A RU 97114134A
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RU
Russia
Prior art keywords
hydroxy
diacetoxy
phenylpropionate
tax
oxo
Prior art date
Application number
RU97114134/04A
Other languages
Russian (ru)
Other versions
RU2154642C2 (en
Inventor
Отелэн Жан-Рене
Дидье Эрик
Левейлле Франк
Тайепье Изабель
Original Assignee
Рон-Пуленк Роре С.А.
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
Priority claimed from FR9500816A external-priority patent/FR2729666A1/en
Application filed by Рон-Пуленк Роре С.А. filed Critical Рон-Пуленк Роре С.А.
Publication of RU97114134A publication Critical patent/RU97114134A/en
Application granted granted Critical
Publication of RU2154642C2 publication Critical patent/RU2154642C2/en

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Claims (7)

1. Способ получения тригидрата 4,10-диацетокси-2α-бензоил-окси-5β,20-эпокси-1,7β-диокси-9-оксо-такс-11-ен-13α-ил(2R, 3S)-3-бензоиламино-2-окси-3-фенилпропионата, отличающийся тем, что осуществляют кристаллизацию 4,10-диацетокси-2α-бензоил-окси-5β, 20-эпокси-1,7β-диокси-9-оксо-такс-11-ен-13α-ил(2R,3S)-3-бензоил-амино-2-окси-3-фенилпропионата в смеси воды и алифатического спирта, содержащего от 1 до 3 атомов углерода, с последующим высушиванием полученного продукта при пониженном давлении и выдерживанием при относительной влажности выше 20%.1. Method for the preparation of 4,10-diacetoxy-2α-benzoyl-hydroxy-5β trihydrate, 20-epoxy-1,7β-dioxi-9-oxo-tax-11-en-13α-yl (2R, 3S) -3- benzoylamino-2-hydroxy-3-phenylpropionate, characterized in that the crystallization of 4,10-diacetoxy-2α-benzoyl-hydroxy-5β, 20-epoxy-1,7β-dioxi-9-oxo-tax-11-ene 13α-yl (2R, 3S) -3-benzoyl amino-2-hydroxy-3-phenylpropionate in a mixture of water and an aliphatic alcohol containing from 1 to 3 carbon atoms, followed by drying of the resulting product under reduced pressure and maintaining at relative humidity above 20%. 2. Способ по п.1, отличающийся тем, что весовое соотношение вода/спирт составляет от 3/1 до 1/3. 2. The method according to claim 1, characterized in that the weight ratio of water / alcohol is from 3/1 to 1/3. 3. Способ по одному из п.1 или 2, отличающийся тем, что спирт является метанолом. 3. The method according to one of claim 1 or 2, characterized in that the alcohol is methanol. 4. Способ по п.1, отличающийся тем, что высушивание осуществляется при температуре около 40oС при пониженном давлении, а полученный продукт стабилизируется при 6% воды при относительной влажности воздуха выше 20%.4. The method according to claim 1, characterized in that the drying is carried out at a temperature of about 40 o With reduced pressure, and the resulting product is stabilized at 6% water with a relative humidity above 20%. 5. Способ по п.1, отличающийся тем, что кристаллизация осуществляется в присутствии аскорбиновой кислоты. 5. The method according to claim 1, characterized in that the crystallization is carried out in the presence of ascorbic acid. 6. Способ по п.1, отличающийся тем, что работают непосредственно in situ со сложным эфиром, полученным в результате реакции этерификации баккатина III, окси-функции которого в положении 13 защищены и защищенного производного β-фениллизозерина после снятия защитных групп. 6. The method according to claim 1, characterized in that they work directly in situ with the ester obtained by the esterification of baccatin III, the hydroxy functions of which are protected at position 13 and of the protected β-phenyllysoserine derivative after deprotection. 7. Тригидрат 4,10-диацетокси-2α-бензоил-окси-5β, 20-эпокси-1,7β-диокси-9-оксо-такс-11-ен-13α-ил(2R,3S)-3-бензоиламино-2-окси-3-фенилпропионата. 7. 4,10-diacetoxy-2α-benzoyl-hydroxy-5β trihydrate, 20-epoxy-1,7β-dioxi-9-oxo-tax-11-en-13α-yl (2R, 3S) -3-benzoylamino 2-hydroxy-3-phenylpropionate.
RU97114134/04A 1995-01-25 1996-01-23 4,10-DIACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1,7β-DIHYDROXY- 9-OXO-TAX-11-ENE-13α-YL-(2R,3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE TRIHYDRATE AND METHOD OF ITS PREPARING RU2154642C2 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9500816 1995-01-25
FR9500816A FR2729666A1 (en) 1995-01-25 1995-01-25 PROCESS FOR THE PREPARATION OF (2R, 3S) TRIHYDRATE - BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE OF 4,10-DIACETOXY- 2ALPHA-BENZOYLOXY-5BETA, 20-EPOXY-1,7BETA-DIHYDROXY-9-OX 11-EN-13ALPHA-YLE

Publications (2)

Publication Number Publication Date
RU97114134A true RU97114134A (en) 1999-06-20
RU2154642C2 RU2154642C2 (en) 2000-08-20

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RU97114134/04A RU2154642C2 (en) 1995-01-25 1996-01-23 4,10-DIACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1,7β-DIHYDROXY- 9-OXO-TAX-11-ENE-13α-YL-(2R,3S)-3-BENZOYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE TRIHYDRATE AND METHOD OF ITS PREPARING

Country Status (43)

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US (1) US6002022A (en)
EP (1) EP0805806B1 (en)
JP (1) JP3782449B2 (en)
KR (1) KR100384773B1 (en)
CN (1) CN1067997C (en)
AP (1) AP750A (en)
AT (1) ATE187719T1 (en)
AU (1) AU707603B2 (en)
BG (1) BG62769B1 (en)
BR (1) BR9606853A (en)
CO (1) CO4700286A1 (en)
CZ (1) CZ287079B6 (en)
DE (1) DE69605651T2 (en)
DK (1) DK0805806T3 (en)
DZ (1) DZ1977A1 (en)
EE (1) EE03396B1 (en)
ES (1) ES2139332T3 (en)
FI (1) FI119245B (en)
FR (1) FR2729666A1 (en)
GE (1) GEP19991833B (en)
GR (1) GR3032110T3 (en)
HU (1) HU223352B1 (en)
IL (1) IL116903A (en)
IN (1) IN184427B (en)
IS (1) IS2033B (en)
MA (1) MA23782A1 (en)
MY (1) MY113230A (en)
NO (1) NO316987B1 (en)
NZ (1) NZ300958A (en)
OA (1) OA10438A (en)
PE (1) PE64896A1 (en)
PL (1) PL183773B1 (en)
PT (1) PT805806E (en)
RO (1) RO115728B1 (en)
RU (1) RU2154642C2 (en)
SK (1) SK281958B6 (en)
TN (1) TNSN96011A1 (en)
TR (1) TR199700676T1 (en)
TW (1) TW356469B (en)
UA (1) UA47420C2 (en)
UY (1) UY24149A1 (en)
WO (1) WO1996022984A1 (en)
ZA (1) ZA96523B (en)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6891050B2 (en) * 2001-08-10 2005-05-10 Dabur India Limited Process for the preparation of taxanes such as paclitaxel, docetaxel and structurally similar analogs
US6881852B2 (en) * 2002-02-05 2005-04-19 Dabur India Limited Process of purification of paclitaxel and docetaxel
US7247738B2 (en) * 2002-05-07 2007-07-24 Dabur India Limited Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl) ethoxycarbonyl]-5-oxazolidine carboxylic acids
US6900342B2 (en) * 2002-05-10 2005-05-31 Dabur India Limited Anticancer taxanes such as paclitaxel, docetaxel and their structural analogs, and a method for the preparation thereof
US6838569B2 (en) * 2002-12-16 2005-01-04 Dabur India Limited Process for preparation of paclitaxel trihydrate and docetaxel trihydrate
WO2005061474A1 (en) * 2003-12-12 2005-07-07 Quiral Química Do Brasil Process for the preparation of anhydrous and hydrated active pharmaceutical ingredients (apis); stable pharmaceutical compositions prepared from the same and uses of said compositions
CN100420681C (en) * 2005-04-29 2008-09-24 上海奥锐特国际贸易有限公司 Production of polyenoic taxad alcohol trihydrate
US20090292131A1 (en) * 2008-05-07 2009-11-26 Ladislav Cvak Processes for preparation of taxanes and intermediates thereof
US8633240B2 (en) * 2012-06-01 2014-01-21 The University Of Utah Research Foundation Paclitaxel trihydrates and methods of making thereof
CN103833693B (en) * 2014-03-04 2016-02-24 悦康药业集团有限公司 A kind of taxol compound and the pharmaceutical composition containing this taxol compound

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WO1994021662A1 (en) * 1993-03-15 1994-09-29 Yale University Diagnosis of human inflammatory bowel diseases and nucleic acid reagents therefor
FR2703049B1 (en) * 1993-03-22 1995-04-21 Rhone Poulenc Rorer Sa Method for the purification of taxoids.
CA2163837C (en) * 1994-12-13 1999-07-20 Robert K. Perrone Crystalline paclitaxel hydrates

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