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KR920703560A - 시스-β-페닐글리시딘-(2R,3R)산의 제조방법 - Google Patents

시스-β-페닐글리시딘-(2R,3R)산의 제조방법

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Publication number
KR920703560A
KR920703560A KR1019920701997A KR920701997A KR920703560A KR 920703560 A KR920703560 A KR 920703560A KR 1019920701997 A KR1019920701997 A KR 1019920701997A KR 920701997 A KR920701997 A KR 920701997A KR 920703560 A KR920703560 A KR 920703560A
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KR
South Korea
Prior art keywords
methylbenzylamine
acid
salt
cis
mixture
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Application number
KR1019920701997A
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English (en)
Other versions
KR100190559B1 (en
Inventor
뒤쉐느 장-삐에르
뮬호제 미쉘
Original Assignee
필라드 자끄
로오느-푸우랜크 로레르 소시에테 아노님
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Publication of KR920703560A publication Critical patent/KR920703560A/ko
Application granted granted Critical
Publication of KR100190559B1 publication Critical patent/KR100190559B1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D305/00—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms
    • C07D305/14—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
    • 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
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C07C233/82—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/87—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
    • C07C271/06—Esters of carbamic acids
    • C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
    • C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • Medicinal Chemistry (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Epoxy Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)

Abstract

내용 없음

Description

시스-β-페닐글리시딘-(2R, 3R)산의 제조방법
[도면의 간단한 설명]
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. (R) (+) -α-메틸벤질아민과 (2R, 3R) -β-페닐글리시딘산, (2S, 3S)-β-페닐글리시딘산, (2R, 3S)-β-페닐글리시딘산 및 (2S,3R)-β-페니리글리시딘산의 염의 혼합물 용액중,(2R3R)-β-페닐 글리시딘산과 (R)(+)-α-메틸벤질아민염을 적합한 용매 내에서 선택적으로 결정화하고, 얻어진 생성물을 분리하고, 임의로 알칼리 금속염 또는 에스테르로 전환시킴을 특징으로 하는, 임의로 염 또는 에스테르 형태의 하기 일반식의 (2R,3R)-시스-β-페닐글리시딘산의 제조방법:
  2. 제1항에 있어서, 용매는 물 및 임의로 물과 혼합된 C1-C4를 함유하는 지방족 알콜, 에테르 및 케톤으로 부터 선택된 유기 용매로 부터 선택됨을 특징으로 하는 방법.
  3. 제1 및 제2항 중 어느 한항에 있어서, 아세톤이 제1항에 정의된 염의 혼합물의 수성, 유기 또는 히드로유기용액에 첨가되고나서, (2R, 3R)-β-페닐글리시딘산과 (R)(+)-α-메틸벤질아민의 염이 침전되고, 여과로 분리됨을 특징으로 하는 방법.
  4. 제1항 내지 제3항중 어느 한 항에 있어서, β-페닐 글리시딘산의 시스 이성질체와 (R) (+)-α-메틸벤질아민의 염이 대략 80% 및 β-페닐글리시딘산의 트란스 이성질체와 (R) (+)-α-메틸벤질아민의 염 대략 20%로 구성된 혼합물이 적용됨을 특징으로 하는 방법.
  5. 제1항 내지 제4항중 어느 한항에 있어서, (R)(+)-α-메틸벤질아민과 β-페닐글리시딘산의 시스 및 트란스 이성질체의 혼합물은, 현장에서 제조된 β-페닐글리시딘산의 시스 및 트란스 이성질체의 혼합물 상의 (+)-α-메틸벤질아민의 작용에 의해 얻어짐을 특징으로 하는 방법.
  6. 제1항 내지 제4항 중 어느 한 항에 있어서, (R)(+)-α-메틸벤질아민과 β-페닐글리시딘산의 시스 및 트란스 이성질체의 혼합물은, 현장에서 임의로 제조된 시스 및 트란스 β-페닐글리시딘산의 알칼리 금속염 혼합물 상의 (+)-α-메틸벤질 아민염의 작용에 의해 얻어짐을 특징으로 하는 방법.
  7. 하기 일반식:
    (식에서, R은 수소원자 또는 아세틸 라디칼을 지시하고, R1은 페닐 또는 t-부톡시 라디칼을 지시한다)의 탁산 유도체의, 공지된 방법에 따른, 제조를 위한 제1항 내지 제6항중 어느 한 항의 방법에 따라 얻어진 생성물의 이용.
  8. 제1항의 방법에 따라 얻어진 생성물을 사용한 방법에 의해 얻어지는 하기 일반식의 생성물:
    식에서 R은 수소원자 또는 아세틸 라디칼을 지시하고, R1은 페닐 또는 t-부톡시 라디칼을 지시한다.
  9. 불활성 또는 생리학적으로 활성인 하나 또는 다수의 제약학적으로 허용가능한 생성물과 조합하여 제8항에 따른 생성물을 함유함을 특징으로 하는 제약학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920701997A 1990-02-21 1992-08-20 Method for preparing cis--g(b)-phenylglycidic-(2r,3r) acid KR100190559B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9002098A FR2658513B1 (fr) 1990-02-21 1990-02-21 Procede de preparation de l'acide cis-beta-phenylglycidique-(2r,3r).
FR90/02098 1990-02-21
PCT/FR1991/000133 WO1991013066A2 (fr) 1990-02-21 1991-02-20 PROCEDE DE PREPARATION DE L'ACIDE CIS-β-PHENYLGLYCIDIQUE-(2R,3R)

Publications (2)

Publication Number Publication Date
KR920703560A true KR920703560A (ko) 1992-12-18
KR100190559B1 KR100190559B1 (en) 1999-06-01

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Application Number Title Priority Date Filing Date
KR1019920701997A KR100190559B1 (en) 1990-02-21 1992-08-20 Method for preparing cis--g(b)-phenylglycidic-(2r,3r) acid

Country Status (24)

Country Link
US (1) US5256803A (ko)
EP (1) EP0515541B1 (ko)
JP (1) JP3012325B2 (ko)
KR (1) KR100190559B1 (ko)
AT (1) ATE104970T1 (ko)
AU (1) AU647088B2 (ko)
CA (1) CA2071979C (ko)
CZ (1) CZ279594B6 (ko)
DE (1) DE69101836T2 (ko)
DK (1) DK0515541T3 (ko)
ES (1) ES2063499T3 (ko)
FI (1) FI113766B (ko)
FR (1) FR2658513B1 (ko)
HU (1) HU207856B (ko)
IE (1) IE65338B1 (ko)
IL (1) IL97276A (ko)
NO (1) NO179836C (ko)
NZ (1) NZ237173A (ko)
PT (1) PT96848B (ko)
RU (1) RU2056414C1 (ko)
SK (1) SK278331B6 (ko)
WO (1) WO1991013066A2 (ko)
YU (1) YU48670B (ko)
ZA (1) ZA911280B (ko)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993010076A1 (en) * 1991-11-22 1993-05-27 The University Of Mississippi Synthesis and optical resolution of the taxol side chain and related compounds
CA2130578A1 (en) * 1992-04-17 1993-10-28 Geewananda P. Gunawardana Taxol derivatives
FR2691460B1 (fr) * 1992-05-21 1994-07-22 Rhone Poulenc Rorer Sa Nouveaux derives du taxane, leur preparation et les compositions qui les contiennent.
MX9307777A (es) 1992-12-15 1994-07-29 Upjohn Co 7-HALO-Y 7ß, 8ß-METANO-TAXOLES, USO ANTINEOPLASTICO Y COMPOSICIONES FARMACEUTICAS QUE LOS CONTIENEN.
US5646176A (en) 1992-12-24 1997-07-08 Bristol-Myers Squibb Company Phosphonooxymethyl ethers of taxane derivatives
US5684175A (en) * 1993-02-05 1997-11-04 Napro Biotherapeutics, Inc. C-2' hydroxyl-benzyl protected, N-carbamate protected (2R, 3S)- 3-phenylisoserine and production process therefor
ATE253563T1 (de) 1993-02-05 2003-11-15 Bryn Mawr College Synthese von taxol, seinen analogen und intermediaten mit variablen a-ring seitenketten
EP0982302B1 (en) * 1993-06-11 2004-04-14 PHARMACIA & UPJOHN COMPANY Delta 6,7-taxols antineoplastic use and pharmaceutical compositions containing them
IL112412A (en) * 1994-01-28 2000-02-29 Upjohn Co Delta 12,13-iso-taxol analogs and antineoplastic pharmaceutical compositions containing them
ATE203018T1 (de) * 1995-04-20 2001-07-15 Chirotech Technology Ltd Asymmetrische epoxide, ihre synthese und ihre verwendung
US5675025A (en) * 1995-06-07 1997-10-07 Napro Biotherapeutics, Inc. Paclitaxel synthesis from precursor compounds and methods of producing the same
FR2740451B1 (fr) 1995-10-27 1998-01-16 Seripharm Nouveaux intermediaires pour l'hemisynthese de taxanes, leurs procedes de preparation et leur utilisation dans la synthese generale des taxanes
US5688977A (en) * 1996-02-29 1997-11-18 Napro Biotherapeutics, Inc. Method for docetaxel synthesis
US6228955B1 (en) 1996-04-19 2001-05-08 Chirotech Technology, Ltd. Asymmetric epoxides, their synthesis and use
US5750737A (en) * 1996-09-25 1998-05-12 Sisti; Nicholas J. Method for paclitaxel synthesis
FR2776292B1 (fr) * 1998-03-20 2004-09-10 Oncopharm Cephalotaxanes porteurs de chaine laterale et leur procede de synthese
US6452025B1 (en) 2001-04-25 2002-09-17 Napro Biotherapeutics, Inc. Three-step conversion of protected taxane ester to paclitaxel
US6479679B1 (en) 2001-04-25 2002-11-12 Napro Biotherapeutics, Inc. Two-step conversion of protected taxane ester to paclitaxel

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Also Published As

Publication number Publication date
NO179836B (no) 1996-09-16
CS9100439A2 (en) 1991-09-15
DE69101836T2 (de) 1994-08-18
YU30291A (sh) 1993-11-16
SK278331B6 (en) 1996-11-06
JPH05503534A (ja) 1993-06-10
FR2658513A1 (fr) 1991-08-23
CZ279594B6 (cs) 1995-05-17
EP0515541A1 (fr) 1992-12-02
ES2063499T3 (es) 1995-01-01
NO923225L (no) 1992-08-18
RU2056414C1 (ru) 1996-03-20
NO923225D0 (no) 1992-08-18
IL97276A (en) 1995-03-30
KR100190559B1 (en) 1999-06-01
HU207856B (en) 1993-06-28
IL97276A0 (en) 1992-05-25
ATE104970T1 (de) 1994-05-15
FI923680A0 (fi) 1992-08-17
CA2071979A1 (fr) 1991-08-22
NZ237173A (en) 1993-07-27
ZA911280B (en) 1991-12-24
JP3012325B2 (ja) 2000-02-21
FI923680L (fi) 1992-08-17
DK0515541T3 (da) 1994-06-13
EP0515541B1 (fr) 1994-04-27
CA2071979C (fr) 2002-10-29
FR2658513B1 (fr) 1994-02-04
PT96848A (pt) 1991-10-31
YU48670B (sh) 1999-06-15
AU7346191A (en) 1991-09-18
NO179836C (no) 1996-12-27
IE65338B1 (en) 1995-10-18
WO1991013066A3 (fr) 1991-10-17
IE910587A1 (en) 1991-08-28
HU9202668D0 (en) 1992-12-28
DE69101836D1 (de) 1994-06-01
WO1991013066A2 (fr) 1991-09-05
FI113766B (fi) 2004-06-15
AU647088B2 (en) 1994-03-17
US5256803A (en) 1993-10-26
PT96848B (pt) 1998-07-31

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