WO1995013271A1 - Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent - Google Patents

Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent Download PDF

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Publication number
WO1995013271A1
WO1995013271A1 PCT/FR1994/001283 FR9401283W WO9513271A1 WO 1995013271 A1 WO1995013271 A1 WO 1995013271A1 FR 9401283 W FR9401283 W FR 9401283W WO 9513271 A1 WO9513271 A1 WO 9513271A1
Authority
WO
WIPO (PCT)
Prior art keywords
carbon atoms
radical
alkyl
radicals
general formula
Prior art date
Application number
PCT/FR1994/001283
Other languages
English (en)
French (fr)
Inventor
Hervé Bouchard
Jean-Dominique Bourzat
Alain Commerçon
Jean-Pierre Pulicani
Original Assignee
Rhone-Poulenc Rorer S.A.
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 Rhone-Poulenc Rorer S.A. filed Critical Rhone-Poulenc Rorer S.A.
Priority to SK574-96A priority Critical patent/SK57496A3/sk
Priority to JP7513626A priority patent/JPH09504801A/ja
Priority to AU81470/94A priority patent/AU686690B2/en
Priority to EP95900794A priority patent/EP0728131A1/fr
Publication of WO1995013271A1 publication Critical patent/WO1995013271A1/fr
Priority to FI961938A priority patent/FI961938A0/fi

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • 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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the product of general formula (IV) is treated with formic acid at a temperature in the region of 20 ° C.
  • the acylation of the product of general formula (V) by means of a product of general formula (VI) is carried out in an inert organic solvent chosen from esters such as ethyl acetate, acetate d isopropyl or n.butyl acetate and halogenated aliphatic hydrocarbons such as dichloromethane or 1,2-dichloroethane in the presence of an inorganic base such as sodium bicarbonate or organic such as triethylamine.
  • the reaction is carried out at a temperature between 0 and 50 ° C, preferably close to 20 ° C.
  • the treatment with a zinc halide is carried out in methanol at a temperature in the region of 20 ° C. 4) when Gi represents an alkoxyacetyl radical and R4 and R5 are defined as in point 2-a) above, the protective group G * is optionally replaced by treatment in an alkaline medium or by treatment with a zinc halide in the conditions described in point 3) above, then treats the product of general formula (V) obtained under the acylation conditions described in point 2-a) above.
  • the product of general formula (VIII) can be obtained: 1) by the action of an alkali metal halide (sodium chloride, potassium fluoride) or an alkali metal azide (sodium azide) or a salt of quaternary ammonium or of an alkali metal phosphate on a product of general formula:
  • the solution is thus kept stirred for 45 minutes and then 10 cm 3 of a saturated aqueous ammonium chloride solution are added.
  • the reaction medium is brought to a temperature in the region of 20 ° C in 1 hour.
  • the solution obtained is poured into a mixture of 50 cm3 of ethyl acetate and 50 cm3 of a saturated aqueous solution of ammonium chloride.
  • the aqueous phase is separated by decantation and then extracted with 2 times 50 cm3 of ethyl acetate.
  • the organic phases are combined, washed with 50 cm3 of distilled water and then dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) at 40 ° C.
  • Therapeutic treatment can be carried out concurrently with other therapeutic treatments including antineoplastic drugs, monoclonal antibodies, immunological therapies or radiotherapies or modifiers of biological responses.
  • Response modifiers include, but are not limited to, lymphokines and cytokines such as interleukins, interferons (a, ⁇ or ⁇ ) and TNF.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
PCT/FR1994/001283 1993-11-08 1994-11-07 Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent WO1995013271A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
SK574-96A SK57496A3 (en) 1993-11-08 1994-11-07 Taxoides, their preparation and pharmaceutical compositions containing them
JP7513626A JPH09504801A (ja) 1993-11-08 1994-11-07 新規なタキソイド類、それらの製造およびそれらを含有する製剤組成物
AU81470/94A AU686690B2 (en) 1993-11-08 1994-11-07 Novel taxoids, their preparation and pharmaceutical compositions containing them
EP95900794A EP0728131A1 (fr) 1993-11-08 1994-11-07 Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
FI961938A FI961938A0 (fi) 1993-11-08 1996-05-07 Uudet taksoidit, niiden valmistus ja niitä sisältävät farmaseuttiset valmisteet

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9313233A FR2712288B1 (fr) 1993-11-08 1993-11-08 Nouveaux taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.
FR93/13233 1993-11-08

Publications (1)

Publication Number Publication Date
WO1995013271A1 true WO1995013271A1 (fr) 1995-05-18

Family

ID=9452585

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR1994/001283 WO1995013271A1 (fr) 1993-11-08 1994-11-07 Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent

Country Status (13)

Country Link
EP (1) EP0728131A1 (fi)
JP (1) JPH09504801A (fi)
CN (1) CN1134700A (fi)
AU (1) AU686690B2 (fi)
CA (1) CA2175384A1 (fi)
CZ (1) CZ133696A3 (fi)
FI (1) FI961938A0 (fi)
FR (1) FR2712288B1 (fi)
HU (1) HUT75063A (fi)
PL (1) PL314234A1 (fi)
SK (1) SK57496A3 (fi)
WO (1) WO1995013271A1 (fi)
ZA (1) ZA948789B (fi)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5589502A (en) * 1994-11-17 1996-12-31 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
US5677470A (en) * 1994-06-28 1997-10-14 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
US5795909A (en) * 1996-05-22 1998-08-18 Neuromedica, Inc. DHA-pharmaceutical agent conjugates of taxanes
US5919815A (en) * 1996-05-22 1999-07-06 Neuromedica, Inc. Taxane compounds and compositions
US6080877A (en) * 1996-05-22 2000-06-27 Neuromedica, Inc. Taxanes
US6495579B1 (en) 1996-12-02 2002-12-17 Angiotech Pharmaceuticals, Inc. Method for treating multiple sclerosis
US6515016B2 (en) 1996-12-02 2003-02-04 Angiotech Pharmaceuticals, Inc. Composition and methods of paclitaxel for treating psoriasis
EP0673372B1 (fr) * 1992-12-09 2003-06-25 Aventis Pharma S.A. Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
US20160235705A1 (en) * 2010-12-22 2016-08-18 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10039737B2 (en) 2008-08-11 2018-08-07 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
US10894087B2 (en) 2010-12-22 2021-01-19 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of cabazitaxel-based compounds

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20100160653A1 (en) * 2006-03-21 2010-06-24 Dr. Reddy's Laboratories Ltd. Docetaxel polymorphs and processes
CN111748825B (zh) * 2019-03-28 2021-09-07 万华化学集团股份有限公司 一种成对电极反应制备ε-己内酯的方法

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5254580A (en) * 1993-01-19 1993-10-19 Bristol-Myers Squibb Company 7,8-cyclopropataxanes
WO1994013654A1 (fr) * 1992-12-09 1994-06-23 Rhone-Poulenc Rorer S.A. Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
WO1994013655A1 (en) * 1992-12-15 1994-06-23 The Upjohn Company 7-HALO- AND 7β,8β-METHANO-TAXOLS, ANTINEOPLASTIC USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1994013654A1 (fr) * 1992-12-09 1994-06-23 Rhone-Poulenc Rorer S.A. Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
WO1994013655A1 (en) * 1992-12-15 1994-06-23 The Upjohn Company 7-HALO- AND 7β,8β-METHANO-TAXOLS, ANTINEOPLASTIC USE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
US5254580A (en) * 1993-01-19 1993-10-19 Bristol-Myers Squibb Company 7,8-cyclopropataxanes

Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0673372B1 (fr) * 1992-12-09 2003-06-25 Aventis Pharma S.A. Nouveaux taxoides, leur preparation et les compositions pharmaceutiques qui les contiennent
US7074821B1 (en) 1992-12-09 2006-07-11 Aventis Pharma, S.A. Taxoids, their preparation and pharmaceutical composition containing them
US5677470A (en) * 1994-06-28 1997-10-14 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
US5608073A (en) * 1994-11-17 1997-03-04 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
US5589502A (en) * 1994-11-17 1996-12-31 Tanabe Seiyaku Co., Ltd. Baccatin derivatives and processes for preparing the same
US5919815A (en) * 1996-05-22 1999-07-06 Neuromedica, Inc. Taxane compounds and compositions
US6080877A (en) * 1996-05-22 2000-06-27 Neuromedica, Inc. Taxanes
US5795909A (en) * 1996-05-22 1998-08-18 Neuromedica, Inc. DHA-pharmaceutical agent conjugates of taxanes
US6495579B1 (en) 1996-12-02 2002-12-17 Angiotech Pharmaceuticals, Inc. Method for treating multiple sclerosis
US6515016B2 (en) 1996-12-02 2003-02-04 Angiotech Pharmaceuticals, Inc. Composition and methods of paclitaxel for treating psoriasis
US10039737B2 (en) 2008-08-11 2018-08-07 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
US11672776B2 (en) 2008-08-11 2023-06-13 Nektar Therapeutics Multi-arm polymeric alkanoate conjugates
US20160235705A1 (en) * 2010-12-22 2016-08-18 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds
US10098865B2 (en) * 2010-12-22 2018-10-16 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
US11813241B2 (en) 2010-12-22 2023-11-14 Nektar Therapeutics Multi-arm polymeric prodrug conjugates of taxane-based compounds

Also Published As

Publication number Publication date
HU9601219D0 (en) 1996-07-29
SK57496A3 (en) 1996-10-02
FI961938A (fi) 1996-05-07
JPH09504801A (ja) 1997-05-13
CZ133696A3 (en) 1996-08-14
CA2175384A1 (fr) 1995-05-18
FR2712288A1 (fr) 1995-05-19
FI961938A0 (fi) 1996-05-07
ZA948789B (en) 1995-07-12
AU686690B2 (en) 1998-02-12
CN1134700A (zh) 1996-10-30
PL314234A1 (en) 1996-09-02
FR2712288B1 (fr) 1996-01-05
AU8147094A (en) 1995-05-29
EP0728131A1 (fr) 1996-08-28
HUT75063A (en) 1997-03-28

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