KR930702324A - 탁산 유도체 제조 방법, 이로써 얻어진 신규한 유도체 및 상기를 함유한 제약학적 조성물 - Google Patents

탁산 유도체 제조 방법, 이로써 얻어진 신규한 유도체 및 상기를 함유한 제약학적 조성물

Info

Publication number
KR930702324A
KR930702324A KR1019930701547A KR930701547A KR930702324A KR 930702324 A KR930702324 A KR 930702324A KR 1019930701547 A KR1019930701547 A KR 1019930701547A KR 930701547 A KR930701547 A KR 930701547A KR 930702324 A KR930702324 A KR 930702324A
Authority
KR
South Korea
Prior art keywords
radical
aryl
phenyl
radicals
product
Prior art date
Application number
KR1019930701547A
Other languages
English (en)
Other versions
KR100206457B1 (ko
Inventor
부르자 장-도미니끄
꼬메르송 알랭
빠리 장-마아끄
Original Assignee
쟈끄 삘라르
로오느-푸우랜크 로레르 소시에테 아노님
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 FR909014635A external-priority patent/FR2669631B1/fr
Priority claimed from FR9109423A external-priority patent/FR2679557B1/fr
Application filed by 쟈끄 삘라르, 로오느-푸우랜크 로레르 소시에테 아노님 filed Critical 쟈끄 삘라르
Publication of KR930702324A publication Critical patent/KR930702324A/ko
Application granted granted Critical
Publication of KR100206457B1 publication Critical patent/KR100206457B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/02—Antineoplastic agents specific for leukemia
    • 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

Abstract

하기 일반식(I)를 갖는 탁산 유도체 제조 방법, 이로써 얻어진 신규한 유도체 및 상기를 함유한 조성물. 일반식(I)에서, R은 t-부톡시 또는 페닐이고, R1은 수소 또는 아세틸이며, Ar은 치환 페닐 또는 임의 치환 α 또는 β-나프틸이다. 상기 신귀한 탁산 유도체는 항백 혈병 및 항종양 약제로서 유용하다.

Description

탁산 유도체 제조 방법, 이로써 얻어진 신규한 유도체 및 상기를 함유한 제약학적 조성물
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (31)

  1. 하기를 특징으로 하는, 하기 일반식의 탁산 유도체 제조 방법:
  3. (상기 식에서 R은 t-부톡시 또는 페닐 라디칼을 나타내고, R1은 수소원자 또는 아세틸 라디칼을 나타내며 Ar은 아릴 라디칼을 나타냄) a) 하기 일반식의 옥사졸리딘 유도체:
  5. (상기 식에서 Ar은 상기와 같이 정의도고, Boc는 t-부톡시카르보닐라디칼을나타내며, 동일하거나 상이할수 있는 R6및 R7은 하나 이상의 아릴(페닐)라디칼로 임의적으로 치환된C1-C4를 함유하는 알킬 라디칼, 또는 아릴(페닐)을 나타내고, 또는 대안적으로 R6및R7은 그들이 연결되어 있는 탄소 원자와 함께,4-내지 7-원고리를 형성함)을 하기 일반식의 탁산 유도체:
  7. (상기 식에서 R'1은 아세틸 라디칼 또는 히드록실 관능 보호기를 나타내고 R2는 히드록실 관능 보호기를 나타냄)와 축합하여, 하기 일반식의 생성물:
  9. (상기 식에서 Ar, R'1, R2및 R7은 상기와 같이 저의됨)을 얻고; b) 생성물을 R'1및 R2에 영향을 미치지 않는 조건 하에서, 산성 매질내에서 처리하여, 하기 일반식의 생성물:
  11. (상기 식에서 R'1및 R2는 상기와 같이 정의됨)을 얻고, c) 생성물을 t-부톡시카로보닐 또는 벤조일 라디칼을 아미노 관능에 도입할 수 있는 적당한 시약 으로 처리하여 하기 일반식의 생성물:
  13. 을 얻고, d) 보호기를 R'1및 R2는 적당히 조건 하에서 수소 원자에 의해 치환된 다음, e) 얻어진 생성물을 분리하고, 적절하다면 정제한다.
  14. 제1항에 있어서, R'1및R2은 제1항에서와 같이 정의되고 Ar은 할로겐(불소, 소, 브롬, 요오드) 원자 및 알킬, 아릴, 아릴알킬, 알콕시, 알킬티오, 아릴옥시, 아릴티오, 히드록실, 메르캅토, 아실아미노, 아로일아미노, 알콕시카르보닐아미노, 아미노, 알킬아미노, 디알킬아미노, 카르복실, 알콕시카르보닐, 카르바모일, 디알킬카르바모일, 시아노, 니트로 및 드리폴루오로메틸 라디칼로부터 선택된 하나 이상의 원자 또는 라디칼로 임이적으로 치환된 a-또는 β-나프틸 라디칼 또는 임의 치환 페닐 라디칼을 나타내며, 단 알킬 라디칼 및 그밖의 라디칼의 알킬 부분은 C1-C4원자를 함유하고 아릴 라디칼은 페닐 또는 α-또는 β-나프틸 라디칼인 일반식(I)의 생성물 제조 방법.
  15. 제1항에 및 2항중 한 항에 있어서, R'1및R2로 나타내어진 보호 라디칼이2,2,2-트리클로로에톡시카르보닐라디칼 또는 2,2,2-트리클로로에톡시카르보닐 하디칼로 전환될 수 잇는 라디칼임을 특징으로 하는 방법.
  16. 제1내지 3항중 한 항에 있어서, 일반식(Ⅱ)의 생성물과 일반식(Ⅲ)의 탁산유도체의 축합이 축합체 및 활성화제의 존재하에서 실행됨을 특징으로 하는 방법.
  17. 제1내지 4항중 한 항에 있어서, 일반식(Ⅳ)의 생성물의 선택적 처리가 무기또는 유기 산에 의해, 적절하다면 알코올 내에서 실행됨을 특징으로 하는 방법.
  18. 제1내지 5항중 한 항에 있어서, 일반식(Ⅴ)의 생성물내로의 t-부톡시카르보닐 또는 벤조일 라디칼의 도입이 디-t-부틸 중탄산염에 의해 실행됨을 특징으로 하는 방법.
  19. 제1내지 6항중 한 항에 있어서, R'1및 R2로 나타내어진 보호기의 수소에 의한치환이 아세트산 매질에서 아연과 함께 또는 아연의 존재하에 지방족 알코올에서 무기 또는 유기 산에 의해 실행됨을 특징으로 하는 방법.
  20. 하기 일반식의 신규한 탁자 유도체:
  22. 상기 식에서 R은t-부톡시 또는 페닐 라디칼을 나타내고 Ar은 할로겐(불소, 염소, 블롬, 요오드)원자 및 알킬, 아릴, 아르알킬, 알콕시, 알킬티오, 아릴옥시, 아릴티오, 히드록실, 메르캅토, 아실아미노, 아로일아미노, 알콕시카르보닐아미노, 아미노, 알킬아미노, 카르복실, 알콕시카르보닐, 카르바모일, 디알킬카르바모일, 시아노, 니트로 및 트리플루오로메틸 라디칼로부터 선택된 하나 이상의 원자 또는 라디칼로 임의적으로 치환된 α-또는 β-나프틸라디칼 또는 임의 치환 페닐 라디칼을 나타내며, 단 알킬 라디칼 및 그박의라디칼의 알킬 부분은 C1-C4원자를 하뮤하고 아릴 라디칼은 페닐 또는 α-또는 β-나프틸 라디칼이다.
  23. 충분한 양의, 제8항에 따른 적어도 하나의 유도체를, 순수한 상태로 또는 비활성 또는 생리학적으로 활성일 수 있는 하나 이상의 제약학적으로 허용가능한 생성물과 함께 함유함을 특징으로 하는 제약학적 조성물.
  24. 유효량의 제8항에 따른 적어도 하나의 생성물을 투여함을 특징으로 하는, 사람 및 포유류에 있어서, 비정상 세포 중식으로 인한 질병의 치료 방법.
  25. 하기 일반식의 옥사졸리딘 유도체:
  27. 상기 식에서 Ar은 제1항 및 2항중 한 항에 따라 정의되고, Boc는 t-부톡시카르보닐라디칼을 나타내며, 동일하거나 상이할 수 있는 R6및R7은 하나 이상의 아릴(페닐)라디칼로 임의적으로 치환된C1-C4탄소원자를 함유한 알킬 라디칼, 또는 아릴(페닐)을 나타내고, 또는 대안적으로 R6및 R7은 그들이 연결되어 있는 탄소원자와 함께 4-내지 7-원 고리를 형성한다.
  28. 하나 의상의 아릴 라디칼로 임의적으로 치환된 메특시알켄, 하나 이상의 아릴 라디칼로 임이적으로 치환된 디메톡시알칸 또는 C4-C7을 함유한 gem-디메특시시클로알킬을 하기 일반식의 페닐 이소세린 유도체:
  30. 상기 식에서 Ar은 제1항 및 제2항중 한 항에 따라 정의되고, Boc는 t-부톡시카르보닐라디칼을 나타내며 R은 페닐라디칼ㄹ 임의적으로 치환된C1-C4를 함유한 알킬 라디칼을 나타냄)와 반응시킨 다음, 얻어진 생성물을 비누화함을 특징으로 하는, 제11항에 따른 옥사졸리딘 유도체 제조 방법.
  31. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930701547A 1990-11-23 1991-11-22 탁산 유도체의 제조 방법, 이로써 얻어진 신규한 유도체 및 이를 함유하는 제약학적 조성물 KR100206457B1 (ko)

Applications Claiming Priority (7)

Application Number Priority Date Filing Date Title
FR14635/90 1990-11-23
FR90/14635 1990-11-23
FR909014635A FR2669631B1 (fr) 1990-11-23 1990-11-23 Nouveaux derives de l'oxazolidine, leur preparation et leur emploi.
FR09423/91 1991-07-25
FR91/09423 1991-07-25
FR9109423A FR2679557B1 (fr) 1991-07-25 1991-07-25 Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent.
PCT/FR1991/000928 WO1992009589A1 (fr) 1990-11-23 1991-11-22 Procede de preparation de derives du taxane, nouveaux derives obtenus et compositions pharmaceutiques qui les contiennent

Publications (2)

Publication Number Publication Date
KR930702324A true KR930702324A (ko) 1993-09-08
KR100206457B1 KR100206457B1 (ko) 1999-07-01

Family

ID=26228347

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930701547A KR100206457B1 (ko) 1990-11-23 1991-11-22 탁산 유도체의 제조 방법, 이로써 얻어진 신규한 유도체 및 이를 함유하는 제약학적 조성물

Country Status (24)

Country Link
US (1) US5476954A (ko)
EP (2) EP0595370B1 (ko)
JP (1) JP3043411B2 (ko)
KR (1) KR100206457B1 (ko)
AT (2) ATE111905T1 (ko)
AU (1) AU655618B2 (ko)
CA (1) CA2096833C (ko)
CZ (1) CZ286749B6 (ko)
DE (2) DE69104223T2 (ko)
DK (2) DK0595370T3 (ko)
ES (2) ES2059207T3 (ko)
FI (2) FI105184B (ko)
GR (1) GR3026238T3 (ko)
HU (1) HU214332B (ko)
IE (2) IE80681B1 (ko)
MX (1) MX9102128A (ko)
NO (1) NO302699B1 (ko)
NZ (2) NZ240698A (ko)
PL (1) PL166893B1 (ko)
PT (2) PT99580B (ko)
RU (1) RU2095356C1 (ko)
SK (1) SK282162B6 (ko)
WO (1) WO1992009589A1 (ko)
YU (1) YU48150B (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020066808A (ko) * 2001-02-14 2002-08-21 주식회사 삼양제넥스 비대칭 아미노히드록실레이션반응을 이용한 탁센 유도체의제조방법

Families Citing this family (144)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5698582A (en) * 1991-07-08 1997-12-16 Rhone-Poulenc Rorer S.A. Compositions containing taxane derivatives
US5739362A (en) * 1991-09-23 1998-04-14 Florida State University Taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US6005138A (en) * 1991-09-23 1999-12-21 Florida State University Tricyclic taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
US7074945B2 (en) 1991-09-23 2006-07-11 Florida State University Metal alkoxide taxane derivatives
US6495704B1 (en) 1991-09-23 2002-12-17 Florida State University 9-desoxotaxanes and process for the preparation of 9-desoxotaxanes
US5283253A (en) * 1991-09-23 1994-02-01 Florida State University Furyl or thienyl carbonyl substituted taxanes and pharmaceutical compositions containing them
US5284865A (en) 1991-09-23 1994-02-08 Holton Robert A Cyclohexyl substituted taxanes and pharmaceutical compositions containing them
US6018073A (en) * 1991-09-23 2000-01-25 Florida State University Tricyclic taxanes having an alkoxy, alkenoxy or aryloxy substituted side-chain and pharmaceutical compositions containing them
US5489601A (en) * 1991-09-23 1996-02-06 Florida State University Taxanes having a pyridyl substituted side-chain and pharmaceutical compositions containing them
US6028205A (en) * 1991-09-23 2000-02-22 Florida State University C2 tricyclic taxanes
US6335362B1 (en) 1991-09-23 2002-01-01 Florida State University Taxanes having an alkyl substituted side-chain and pharmaceutical compositions containing them
US6794523B2 (en) 1991-09-23 2004-09-21 Florida State University Taxanes having t-butoxycarbonyl substituted side-chains and pharmaceutical compositions containing them
US5728725A (en) * 1991-09-23 1998-03-17 Florida State University C2 taxane derivaties and pharmaceutical compositions containing them
US5654447A (en) * 1991-09-23 1997-08-05 Florida State University Process for the preparation of 10-desacetoxybaccatin III
ATE349424T1 (de) * 1991-09-23 2007-01-15 Univ Florida State Beta-lactame verwendbar zur herstellung von substituierten isoserinestern mit metallalkoxiden
US5250683A (en) * 1991-09-23 1993-10-05 Florida State University Certain substituted taxanes and pharmaceutical compositions containing them
US5430160A (en) * 1991-09-23 1995-07-04 Florida State University Preparation of substituted isoserine esters using β-lactams and metal or ammonium alkoxides
US5728850A (en) * 1991-09-23 1998-03-17 Florida State University Taxanes having a butenyl substituted side-chain and pharmaceutical compositions containing them
FR2696459B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés du taxane.
FR2696461B1 (fr) * 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Nouveaux dérivés d'analogues du taxol, leur préparation et les compositions qui les contiennent.
FR2696458B1 (fr) * 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés du taxane.
FR2696463B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
FR2696462B1 (fr) 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé d'obtention de la désacétyl-10 baccatine III.
FR2696460B1 (fr) * 1992-10-05 1994-11-25 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés du taxane.
FR2696464B1 (fr) * 1992-10-05 1994-11-10 Rhone Poulenc Rorer Sa Nouveau procédé d'estérification de la baccatine III et de la désacétyl-10 baccatine III.
FR2697019B1 (fr) * 1992-10-15 1994-11-25 Rhone Poulenc Rorer Sa Nouveaux dérivés du taxane, leur préparation et les compositions pharmaceutiques qui les contiennent.
FR2697522B1 (fr) * 1992-10-30 1994-11-25 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés du taxane.
FR2697752B1 (fr) 1992-11-10 1995-04-14 Rhone Poulenc Rorer Sa Compositions antitumorales contenant des dérivés du taxane.
FR2698361B1 (fr) * 1992-11-20 1995-01-13 Rhone Poulenc Rorer Sa Procédé de préparation d'un acide oxazolidine-1,3 carboxylique-5.
JPH06157330A (ja) * 1992-11-27 1994-06-03 Ensuiko Sugar Refining Co Ltd タキソールのサイクロデキストリン包接物，その製造法と用途
US5684169A (en) * 1992-11-27 1997-11-04 Ensuiko Sugar Refining Co., Ltd. Cyclodextrin inclusion complex of taxol, and method for its production and its use
CA2109861C (en) * 1992-12-04 1999-03-16 Shu-Hui Chen 6,7-modified paclitaxels
US5380751A (en) * 1992-12-04 1995-01-10 Bristol-Myers Squibb Company 6,7-modified paclitaxels
FR2698871B1 (fr) 1992-12-09 1995-02-24 Rhone Poulenc Rorer Sa Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
IL107950A (en) * 1992-12-15 2001-04-30 Upjohn Co b 7, b 8 - Matano - Taxols, their preparation and pharmaceutical preparations against malignant tumors containing them
US5973160A (en) * 1992-12-23 1999-10-26 Poss; Michael A. Methods for the preparation of novel sidechain-bearing taxanes
CA2119261C (en) * 1992-12-23 2006-01-31 Michael A. Poss Novel sidechain-bearing taxanes and intermediates thereof
US5646176A (en) * 1992-12-24 1997-07-08 Bristol-Myers Squibb Company Phosphonooxymethyl ethers of taxane derivatives
ATE232854T1 (de) * 1993-03-05 2003-03-15 Univ Florida State Verfahren zur herstellung von 9-desoxotaxanen
US6710191B2 (en) 1993-03-05 2004-03-23 Florida State University 9β-hydroxytetracyclic taxanes
US5547981A (en) * 1993-03-09 1996-08-20 Enzon, Inc. Taxol-7-carbazates
FR2703049B1 (fr) * 1993-03-22 1995-04-21 Rhone Poulenc Rorer Sa Procédé de purification des taxoïdes.
US5475011A (en) * 1993-03-26 1995-12-12 The Research Foundation Of State University Of New York Anti-tumor compounds, pharmaceutical compositions, methods for preparation thereof and for treatment
FR2703353B1 (fr) 1993-03-29 1995-05-05 Rhone Poulenc Rorer Sa Procédé de préparation de dérivés de la beta-phénylisosérine.
DK0982301T3 (da) * 1993-06-11 2003-12-08 Upjohn Co Delta 6,7-taxoler antineoplastisk anvendelse og farmaceutiske præparater indeholdende disse
FR2706457B1 (fr) * 1993-06-16 1995-07-28 Rhone Poulenc Rorer Sa Procédé de préparation d'un acide oxazolidinecarboxylique utile pour préparer des taxoïdes thérapeutiquement actifs.
FR2707165B1 (fr) * 1993-07-06 1995-08-11 Rhone Poulenc Rorer Sa Application des taxoides au traitement de maladies d'origine parasitaire .
US6005120A (en) 1993-07-20 1999-12-21 Florida State University Tricyclic and tetracyclic taxanes
FR2715307B1 (fr) * 1994-01-25 1996-04-05 Commissariat Energie Atomique Procédé de solubilisation dans un milieu aqueux d'agents antitumoraux de la famille du taxol, et cyclodextrines ramifiées utilisables pour cette solubilisation.
IL127598A (en) * 1994-01-28 2003-04-10 Upjohn Co Process for preparing isotaxol analogs
FR2718137B1 (fr) 1994-04-05 1996-04-26 Rhone Poulenc Rorer Sa Procédé de préparation de trialcoylsilyl-7 baccatine III.
US5677470A (en) 1994-06-28 1997-10-14 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
CA2162759A1 (en) * 1994-11-17 1996-05-18 Kenji Tsujihara Baccatin derivatives and processes for preparing the same
US5679807A (en) * 1995-01-30 1997-10-21 Hauser, Inc. Preparation of taxol and docetaxel through primary amines
CA2170661A1 (en) 1995-03-22 1996-09-23 John K. Thottathil Novel methods for the preparation of taxanes using oaxzolidine intermediates
US6372780B2 (en) 1995-03-27 2002-04-16 Aventis Pharma S.A. Methods of treating cell lines expressing multidrug resistance P-glycoprotein
MA23823A1 (fr) 1995-03-27 1996-10-01 Aventis Pharma Sa Nouveaux taxoides, leur preparation et les compositions qui les contiennent
US5847170A (en) * 1995-03-27 1998-12-08 Rhone-Poulenc Rorer, S.A. Taxoids, their preparation and pharmaceutical compositions containing them
GB9512471D0 (en) * 1995-06-20 1995-08-23 Pharmacia Spa Method for the preparation of taxol and its derivatives
EP0927175A4 (en) 1996-05-06 2002-05-22 Univ Florida State 1-DEOXYBACCATIN III, 1-DEOXYTAXOL AND 1-DEOXYTAXOL ANALOG AND METHOD FOR THE PRODUCTION THEREOF
ATE277898T1 (de) * 1996-05-08 2004-10-15 Upjohn Co Verfahren zu herstellung von taxol
WO1997044026A1 (en) * 1996-05-22 1997-11-27 Neuromedica, Inc. Compositions comprising conjugates of cis-docosahexaenoic acid and taxotere
US5919815A (en) * 1996-05-22 1999-07-06 Neuromedica, Inc. Taxane compounds and compositions
US6576636B2 (en) 1996-05-22 2003-06-10 Protarga, Inc. Method of treating a liver disorder with fatty acid-antiviral agent conjugates
US5795909A (en) * 1996-05-22 1998-08-18 Neuromedica, Inc. DHA-pharmaceutical agent conjugates of taxanes
US5773629A (en) * 1996-06-14 1998-06-30 Industrial Technology Research Institute Synthesis of (4S, 5R) -2, 4-diphenyl-5-carboxy-oxazoline derivative as taxol side-chain precursor
WO1998017656A1 (en) * 1996-10-24 1998-04-30 Institute Armand-Frappier A family of canadensol taxanes, the semi-synthetic preparation and therapeutic use thereof
US6515016B2 (en) 1996-12-02 2003-02-04 Angiotech Pharmaceuticals, Inc. Composition and methods of paclitaxel for treating psoriasis
US20030157187A1 (en) * 1996-12-02 2003-08-21 Angiotech Pharmaceuticals, Inc. Compositions and methods for treating or preventing inflammatory diseases
US6495579B1 (en) 1996-12-02 2002-12-17 Angiotech Pharmaceuticals, Inc. Method for treating multiple sclerosis
US6103698A (en) 1997-03-13 2000-08-15 Basf Aktiengesellschaft Dolastatin-15 derivatives in combination with taxanes
US5917062A (en) * 1997-11-21 1999-06-29 Indena S.P.A Intermediates and methods useful in the semisynthesis of paclitaxel and analogs
US6156789A (en) * 1998-03-17 2000-12-05 Rhone-Poulenc Rorer S.A. Method for treating abnormal cell proliferation in the brain
US6346543B1 (en) * 1998-08-17 2002-02-12 Aventis Pharma S.A. Use of a taxoid to treat abnormal cell proliferation in the brain
EP0982027A1 (en) * 1998-08-17 2000-03-01 Aventis Pharma S.A. Taxoid derivatives for treating abnormal cell proliferation of the brain
IT1308636B1 (it) * 1999-03-02 2002-01-09 Indena Spa Procedimento per la preparazione di tassani da 10-desacetilbaccatinaiii.
US7235583B1 (en) 1999-03-09 2007-06-26 Luitpold Pharmaceuticals, Inc., Fatty acid-anticancer conjugates and uses thereof
ITMI991483A1 (it) * 1999-07-06 2001-01-06 Indena Spa Derivati tassanici e procedimenti per la loro preparazione
CA2385528C (en) 1999-10-01 2013-12-10 Immunogen, Inc. Compositions and methods for treating cancer using immunoconjugates and chemotherapeutic agents
BR0104351A (pt) 2000-02-02 2002-01-02 Univ Florida State Res Found Taxanos substituìdos com carbonato c7 como agentes antitumor
CA2397425A1 (en) * 2000-02-29 2001-09-07 Ivan David Horak Farnesyl protein transferase inhibitor combinations with taxane compounds
AU2000261768A1 (en) * 2000-08-08 2002-02-18 Dr. Reddy's Research Foundation An improved process for the preparation of docetaxel
HUP0302599A3 (en) * 2000-09-22 2005-05-30 Bristol Myers Squibb Co Method for reducing toxicity of combined chemotherapic compositions
US20020183266A1 (en) 2001-03-15 2002-12-05 Aventis Pharma, S.A. Combination comprising combretastatin and anticancer agents
EP1427407A4 (en) 2001-03-23 2005-05-11 Luitpold Pharm Inc CONJUGATES BASED ON FATTY AMINES AND PHARMACEUTICAL AGENTS
US6531611B2 (en) * 2001-03-23 2003-03-11 Scinopharm Taiwan, Ltd. Process for making taxane derivatives
US20020182204A1 (en) * 2001-03-23 2002-12-05 Marie-Christine Bissery Combination of a taxane and a cyclin-dependent kinase
ATE556706T1 (de) 2001-03-23 2012-05-15 Luitpold Pharm Inc Fettalkohol-arzneimittel-konjugate
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
MXPA04005038A (es) 2001-11-30 2004-08-11 Bristol Myers Squibb Co Solvatos de paclitaxel.
US6881852B2 (en) * 2002-02-05 2005-04-19 Dabur India Limited Process of purification of paclitaxel and docetaxel
DK2264172T3 (da) 2002-04-05 2017-11-27 Roche Innovation Ct Copenhagen As Oligomerforbindelser til modulering af HIF-1á-ekspression
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
CA2486124A1 (en) 2002-05-17 2003-11-27 Aventis Pharma S.A. Use of docetaxel/doxorubicin/cyclophosphamide in adjuvant therapy of breast and ovarian cancer
CN100436454C (zh) * 2002-06-28 2008-11-26 中国医学科学院药物研究所 新的三尖杉碱类的酯碱衍生物及其制法和其药物组合物与用途
US6838569B2 (en) 2002-12-16 2005-01-04 Dabur India Limited Process for preparation of paclitaxel trihydrate and docetaxel trihydrate
US7713738B2 (en) 2003-02-10 2010-05-11 Enzon Pharmaceuticals, Inc. Oligomeric compounds for the modulation of survivin expression
EP1664033B1 (en) 2003-09-25 2007-11-07 Tapestry Pharmaceuticals, Inc. 9,10-alpha,alpha-oh-taxane analogs and methods for production the reof
EP1810968A3 (en) * 2003-09-25 2007-08-08 Tapestry Pharmaceuticals, Inc. 9, 10-a, a-OH-taxane analogs and methods for production thereof
US20050208095A1 (en) * 2003-11-20 2005-09-22 Angiotech International Ag Polymer compositions and methods for their use
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
KR20070006709A (ko) 2003-12-23 2007-01-11 산타리스 팔마 에이/에스 Ｂｃｌ-2의 조절을 위한 올리고머 화합물
US7446126B2 (en) * 2004-10-08 2008-11-04 Indena S.P.A. Semisynthesis process for the preparation of 10-deacetyl-N-debenzoyl-paclitaxel
US9447138B2 (en) 2004-11-09 2016-09-20 Roche Innovation Center Copenhagen A/S Potent LNA oligonucleotides for the inhibition of HIF-1a expression
EP1833840B9 (en) 2004-11-09 2010-11-10 Santaris Pharma A/S Potent lna oligonucleotides for the inhibition of hif-1a
BRPI0517613A (pt) 2004-11-09 2008-10-14 Santaris Pharma As oligonucleotìdeos lna e tratamento de cáncer
WO2006055837A2 (en) 2004-11-19 2006-05-26 Dr. Reddy's Laboratories Ltd. Process for preparing oxazolidine derivatives
US20080161251A1 (en) 2005-01-21 2008-07-03 Astex Therapeutics Limited Pharmaceutical Compounds
RS52438B (en) * 2005-03-31 2013-02-28 Accord Healthcare Inc. PREPARATION OF 9-DIHYDRO-13-ACETYLBACCATINE TAXAN III
JP2009533330A (ja) * 2006-03-21 2009-09-17 ドクター レディズ ラボラトリーズ リミテッド ドセタキセルの多形体およびプロセス
US11786504B2 (en) 2006-09-28 2023-10-17 Tapestry Pharmaceuticals, Inc. Taxane analogs for the treatment of brain cancer
WO2008106621A1 (en) 2007-02-28 2008-09-04 Tapestry Pharmaceuticals, Inc Taxane analogs for the treatment of brain cancer
EP2073807A1 (en) 2006-10-12 2009-07-01 Astex Therapeutics Limited Pharmaceutical combinations
US8916552B2 (en) 2006-10-12 2014-12-23 Astex Therapeutics Limited Pharmaceutical combinations
KR101266549B1 (ko) * 2006-10-20 2013-05-24 시노팜 싱가포르 피티이 리미티드 결정형 무수 도세탁셀을 제조하는 방법
WO2008121476A1 (en) 2007-03-28 2008-10-09 Tapestry Pharmaceuticals, Inc. Biologically active taxane analogs and methods of treatment by oral administration
US11873308B2 (en) 2006-11-06 2024-01-16 Tapestry Pharmaceuticals, Inc. Biologically active taxane analogs and methods of treatment by oral administration
WO2008063129A1 (en) * 2006-11-20 2008-05-29 Duecom Use of lipid containing particles comprising quillaja saponins for the treatment of cancer
KR100847331B1 (ko) * 2006-12-14 2008-07-21 한미약품 주식회사 도세탁셀의 제조방법 및 이에 사용되는 중간체
KR100921036B1 (ko) * 2006-12-18 2009-10-08 한미약품 주식회사 탁산유도체의 제조방법 및 이에 사용되는 중간체
CN101468974B (zh) * 2007-12-28 2011-02-09 上海百灵医药科技有限公司 多烯紫杉醇的半合成方法
DK2080764T3 (da) 2008-01-18 2012-09-24 Indena Spa Faste former af ortataxel
KR101032761B1 (ko) * 2008-08-06 2011-05-06 주식회사 셀트리온화학연구소 도세탁셀의 제조방법 및 도세탁셀의 제조를 위한 신규한중간체
KR101671537B1 (ko) 2008-08-11 2016-11-01 넥타르 테라퓨틱스 다분지형 중합체 알카노에이트 컨쥬게이트
CN101735179B (zh) * 2008-11-19 2012-09-12 上海百灵医药科技有限公司 一种多烯紫杉醇的制备方法，其中间体及制备方法
WO2010059916A2 (en) * 2008-11-20 2010-05-27 Dr. Reddy's Laboratories Ltd. Preparation of docetaxel
KR20100060351A (ko) 2008-11-27 2010-06-07 한국생명공학연구원 Ｌ１ｃａｍ의 활성 또는 발현을 억제하는 물질 및 항암제를포함하는 항암용 조성물
FR2939665B1 (fr) 2008-12-12 2011-10-07 Sanofi Aventis Combinaison antitumorale associant l'ave8062a et le docetaxel
PL388144A1 (pl) 2009-05-29 2010-12-06 Przedsiębiorstwo Produkcyjno-Wdrożeniowe Ifotam Spółka Z Ograniczoną Odpowiedzialnością Solwaty (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylopropionianu 4-acetoksy-2α-benzoiloksy -5β,20-epoksy-1,7β,10β-trihydroksy-9-okso-taks-11-en-13α-ylu, sposób ich otrzymywania i zastosowanie
CN102010383B (zh) * 2010-11-24 2012-08-15 上海博速医药科技有限公司 一种多烯紫杉醇手性侧链中间体的制备方法
US20130338216A1 (en) 2010-12-22 2013-12-19 Nektar Therapeutics Deuterated and/or fluorinated taxane derivatives
US20130331443A1 (en) 2010-12-22 2013-12-12 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10894087B2 (en) 2010-12-22 2021-01-19 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds
KR102090740B1 (ko) 2011-10-03 2020-03-18 엠엑스 아쥬바크 에이비 암 치료 및 식품 관련 화합물을 포함하는 의학 분야에서 양친매성 또는 소수성 분자를 위한 나노입자, 제조 방법 및 담체로의 용도
JP5847942B2 (ja) 2012-07-19 2016-01-27 富士フイルム株式会社 タキサン系活性成分含有液体組成物、その製造方法及び液体製剤
AR095962A1 (es) 2013-04-01 2015-11-25 Moreinx Ab Nanopartículas, compuestas de esterol y saponina de quillaja saponaria molina, proceso para preparación y uso de las mismas como portadores para moléculas anfipáticas o hidrófobas en el campo de la medicina incluyendo tratamiento de cáncer y compuestos relacionados con alimentos
WO2016098015A1 (en) * 2014-12-16 2016-06-23 Khashayar Karimian New efficient methods for the synthesis of taxane derivatives such as docetaxel and their structural analogous, and a method for the preparation thereof
US11279694B2 (en) 2016-11-18 2022-03-22 Sumitomo Dainippon Pharma Oncology, Inc. Alvocidib prodrugs and their use as protein kinase inhibitors
WO2019055579A1 (en) 2017-09-12 2019-03-21 Tolero Pharmaceuticals, Inc. TREATMENT REGIME FOR CANCERS THAT ARE INSENSITIVE TO BCL-2 INHIBITORS USING THE MCL-1 ALVOCIDIB INHIBITOR
EP3745518B1 (en) * 2018-01-26 2022-04-13 Panasonic Intellectual Property Management Co., Ltd. Battery
MX2021006544A (es) 2018-12-04 2021-07-07 Sumitomo Pharma Oncology Inc Inhibidores de cinasa dependiente de ciclina 9 (cdk9) y polimorfos de los mismos para uso como agentes para el tratamiento de cancer.
EP3669890A1 (en) 2018-12-18 2020-06-24 Croda International PLC Filamentous nanoparticles having vaccine adjuvant effect
WO2020191326A1 (en) 2019-03-20 2020-09-24 Sumitomo Dainippon Pharma Oncology, Inc. Treatment of acute myeloid leukemia (aml) with venetoclax failure

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0174810B1 (en) * 1984-09-10 1993-07-21 HSC Research Development Corporation Multidrug resistance in mammalian cell lines and isolation of determinant glycoprotein dna
FR2601676B1 (fr) * 1986-07-17 1988-09-23 Rhone Poulenc Sante Procede de preparation du taxol et du desacetyl-10 taxol
FR2629819B1 (fr) * 1988-04-06 1990-11-16 Rhone Poulenc Sante Procede de preparation de derives de la baccatine iii et de la desacetyl-10 baccatine iii

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020066808A (ko) * 2001-02-14 2002-08-21 주식회사 삼양제넥스 비대칭 아미노히드록실레이션반응을 이용한 탁센 유도체의제조방법

Also Published As

Publication number Publication date
US5476954A (en) 1995-12-19
FI932331A0 (fi) 1993-05-21
FI981590A (fi) 1998-07-10
DE69128971T2 (de) 1998-09-24
PT99580B (pt) 1999-07-30
HU214332B (hu) 1998-03-02
HU9301500D0 (en) 1993-09-28
EP0558623A1 (fr) 1993-09-08
EP0595370B1 (fr) 1998-02-25
EP0595370A3 (en) 1994-06-22
CA2096833C (fr) 2003-04-08
DE69104223D1 (de) 1994-10-27
ES2059207T3 (es) 1994-11-01
PT102283B (pt) 2002-01-30
MX9102128A (es) 1992-07-08
PT99580A (pt) 1992-10-30
EP0558623B1 (fr) 1994-09-21
FI981590A0 (fi) 1991-11-22
DE69128971D1 (de) 1998-04-02
NO931805L (no) 1993-05-18
JP3043411B2 (ja) 2000-05-22
FI106261B (fi) 2000-12-29
YU182691A (sh) 1994-01-20
ATE111905T1 (de) 1994-10-15
FI932331A (fi) 1993-05-21
IE914073A1 (en) 1992-06-03
EP0595370A2 (fr) 1994-05-04
DK0558623T3 (da) 1994-10-17
NZ240698A (en) 1994-08-26
SK50793A3 (en) 1993-09-09
JPH06504771A (ja) 1994-06-02
HUT63839A (en) 1993-10-28
NO931805D0 (no) 1993-05-18
SK282162B6 (sk) 2001-11-06
CZ286749B6 (cs) 2000-06-14
AU655618B2 (en) 1995-01-05
IE80681B1 (en) 1998-12-02
CZ96593A3 (en) 1994-02-16
GR3026238T3 (en) 1998-05-29
DK0595370T3 (da) 1998-06-02
NO302699B1 (no) 1998-04-14
KR100206457B1 (ko) 1999-07-01
PL166893B1 (pl) 1995-06-30
DE69104223T2 (de) 1995-01-26
ES2112377T3 (es) 1998-04-01
NZ247867A (en) 1994-08-26
AU9083891A (en) 1992-06-25
WO1992009589A1 (fr) 1992-06-11
YU48150B (sh) 1997-05-28
PT102283A (pt) 2000-10-31
FI105184B (fi) 2000-06-30
RU2095356C1 (ru) 1997-11-10
ATE163415T1 (de) 1998-03-15
CA2096833A1 (fr) 1992-05-24
IE65642B1 (en) 1995-11-15

Similar Documents

Publication Publication Date Title
KR930702324A (ko) 탁산 유도체 제조 방법, 이로써 얻어진 신규한 유도체 및 상기를 함유한 제약학적 조성물
KR920000788A (ko) 폴리펩티드 화합물 및 그것의 제조방법
KR830009107A (ko) 2-페넴 화합물의 제조방법
KR920000731A (ko) 신규 이미다졸 유도체, 그의 제조 방법, 그로부터 얻어진 신규 중간체, 의약으로서의 용도 및 그를 함유하는 제약 조성물
ATE14115T1 (de) Amidderivate, verfahren zu ihrer herstellung sowie sie enthaltende pharmazeutische oder fuer veterinaerzwecke verwendbare zusammensetzungen.
US3897480A (en) N-(mercaptoacyl)aminoacids
KR910009712A (ko) 세펨 화합물 및 이의 제조방법
KR850004472A (ko) 4h-3,i-벤즈옥사진-4-온 유도체의 제조방법
KR930023329A (ko) 시클로펜탄- 및- 펜텐- β- 아미노산
KR920012052A (ko) 심장혈관계에 작용하는 벤즈옥사지논 및 벤조티아지논 유도체
JPS58203982A (ja) ビタミンｅ−アミノ酸エステル類およびその製造方法
EP0772630B1 (fr) Derives de streptogramine, leur preparation et les compositions pharmaceutiques qui les contiennent
US2791603A (en) Process for preparing carbamates of tertiary acetylenic carbinols
CZ187194A3 (en) Novel anhydrides of acids, process of their preparation and use
KR860000262A (ko) 3-니트로-디히드로 피리딘의 제조방법
FR2482958A2 (fr) Nouveaux tripeptides, leur preparation et les medicaments qui les contiennent
KR920004377A (ko) 피리딘카복실산 아미드 유도체 및 이를 함유하는 약제학적 조성물
JPH10158163A (ja) 消化管障害軽減剤

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20110317

Year of fee payment: 13

EXPY Expiration of term