WO1997021695A1 - DIHYDRATE DU (2R,3S)-3-TERT-BUTOXYCARBONYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE DE 4,10β-DIACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1-HYDROXY-9-OXO-19-NOR-CYCLOPROPA[G]TAX-11-ENE-13α-YLE, ET SON PROCEDE DE PREPARATION - Google Patents

DIHYDRATE DU (2R,3S)-3-TERT-BUTOXYCARBONYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE DE 4,10β-DIACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1-HYDROXY-9-OXO-19-NOR-CYCLOPROPA[G]TAX-11-ENE-13α-YLE, ET SON PROCEDE DE PREPARATION Download PDF

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Publication number
WO1997021695A1
WO1997021695A1 PCT/FR1996/001957 FR9601957W WO9721695A1 WO 1997021695 A1 WO1997021695 A1 WO 1997021695A1 FR 9601957 W FR9601957 W FR 9601957W WO 9721695 A1 WO9721695 A1 WO 9721695A1
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WO
WIPO (PCT)
Prior art keywords
hydroxy
diacetoxy
cyclopropa
tax
ene
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.)
Ceased
Application number
PCT/FR1996/001957
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English (en)
French (fr)
Inventor
Eric Didier
Michel Lavigne
Jean-René Authelin
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.)
Aventis Pharma SA
Original Assignee
Rhone Poulenc Rorer SA
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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=9485512&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=WO1997021695(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority to UA98063068A priority Critical patent/UA55401C2/uk
Priority to CA002236545A priority patent/CA2236545C/fr
Priority to AU11013/97A priority patent/AU713086C/en
Priority to EP96941720A priority patent/EP0876361B1/fr
Priority to NZ323964A priority patent/NZ323964A/xx
Priority to EA199800452A priority patent/EA000668B1/ru
Priority to HU9904048A priority patent/HU224962B1/hu
Priority to DE69614716T priority patent/DE69614716T2/de
Priority to DK96941720T priority patent/DK0876361T3/da
Priority to BR9611957A priority patent/BR9611957A/pt
Priority to JP52179097A priority patent/JP4059351B2/ja
Priority to IL12476696A priority patent/IL124766A/xx
Application filed by Rhone Poulenc Rorer SA filed Critical Rhone Poulenc Rorer SA
Priority to RO98-01069A priority patent/RO115880B1/ro
Priority to AT96941720T priority patent/ATE204573T1/de
Priority to PL96327451A priority patent/PL187613B1/pl
Priority to SK790-98A priority patent/SK282512B6/sk
Publication of WO1997021695A1 publication Critical patent/WO1997021695A1/fr
Priority to NO19982561A priority patent/NO317356B1/no
Priority to US09/367,387 priority patent/US6150541A/en
Priority to BG102535A priority patent/BG63010B1/bg
Anticipated expiration legal-status Critical
Priority to GR20010400773T priority patent/GR3036437T3/el
Ceased legal-status Critical Current

Links

Classifications

    • 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
    • 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

Definitions

  • the present invention relates to (2R, 3S) -3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate of 4,10 ⁇ -diacetoxy-2 ⁇ -benzoyl-oxy-5 ⁇ , 20-epoxy-1-hydroxy-9 -oxo-19-nor-cyclopropa [g] tax-l l-ene-13 ⁇ -yle, and its preparation.
  • the (2R, 3S) -3-ter-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate of 4,10 ⁇ -diacetoxy-2 ⁇ -benzoyloxy-5 ⁇ , 20-epoxy-1 - hydroxy-9- oxo-19-nor-cyclopropa [g] tax-ll-ene-13 ⁇ -yle can be obtained by crystallization of 4,10 ⁇ -diacetoxy (2R, 3S) -3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate -2 ⁇ -benzoyloxy-5 ⁇ , 20-epoxy-l-hydroxy-9-oxo-19-nor-cyclopropa [g] tax-l l-en-13 ⁇ -yl or by recrystallization of the dihydrate from a mixture of water and d an aliphatic alcohol containing 1 to 3 carbon atoms, or a mixture of water and a ketone containing 3 to 4 carbon atoms followed by drying under reduced
  • the amount of alcohol or ketone is between 4 and 16 parts by volume relative to the weight of (2R, 3S) -3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate of 4,10 ⁇ -diacetoxy -2 ⁇ -benzoyl-oxy-5 ⁇ , 20-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa [g] tax-ll-ene-13 ⁇ -yle used.
  • water is added so that the final water / alcohol or water / ketone volume ratio is between 1/3 and 3/1.
  • Thermogravimetric analysis is carried out using a Perkin-Elmer TGA 7 ® thermobalance at the initial temperature of 25 ° C and at the final temperature of 300 ° C with a temperature gradient of 10 ° C per minute.
  • the solution After returning the reactor to atmospheric pressure, the solution is clarified by passing through a filter fitted with a 0.45 ⁇ m filter cloth. After rinsing the filter with 1 liter of absolute ethanol, about 1.8 liters of water are added over 1 hour at 40 ° C to the whole of the solution.
  • the suspension is filtered on sintered glass and the wrung product is washed with 1.25 liters of an alcohol-water mixture (50-50 by volume).
  • the product is dried in an oven at 35 ° C under 5.3 kPa for 72 hours in the presence of a water reservoir and then at 35 ° C under 2.7 kPa for 8 hours without water reserve and again at 35 ° C at 5.3 kPa for 16 hours in the presence of a water reserve.
  • the X-ray powder diagram is carried out under the conditions described in Example 1.
  • the X-ray powder diagram is carried out under the conditions described in Example 1.
  • the solution is seeded with a suspension of 1 g of (2R, 3S) -3-tert-butoxycarbonylamino-2-hydroxy-3- ⁇ henyl-propionate dihydrate of 4,10 ⁇ -diacetoxy-2 ⁇ -benzoyloxy-5 ⁇ , 20-epoxy- l-hydroxy-9-oxo-19-nor-cyclopropa [g] tax-ll-ene-13 ⁇ -yl in a mixture of 40 cm3 of water and 40 cm3 of absolute ethanol. After maintaining for 15 hours at approximately 40 ° C., 410 cm3 of water are added over 4-5 hours, then the suspension is cooled to 20 ° C.
  • the X-ray powder diagram is carried out under the conditions described in Example 1.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Hematology (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Epoxy Compounds (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)
PCT/FR1996/001957 1995-12-14 1996-12-09 DIHYDRATE DU (2R,3S)-3-TERT-BUTOXYCARBONYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE DE 4,10β-DIACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1-HYDROXY-9-OXO-19-NOR-CYCLOPROPA[G]TAX-11-ENE-13α-YLE, ET SON PROCEDE DE PREPARATION Ceased WO1997021695A1 (fr)

Priority Applications (20)

Application Number Priority Date Filing Date Title
UA98063068A UA55401C2 (uk) 1995-12-14 1996-09-12 ДИГІДРАТ (2R,3S)-3-ТРЕТ-БУТОКСИКАРБОНІЛАМІНО-2-ГІДРОКСИ-3-ФЕНІЛПРОПІОНАТУ 4,10<font face="Symbol">b</font>-ДІАЦЕТОКСИ-2<font face="Symbol">a</font>-БЕНЗОЇЛОКСІ-5<font face="Symbol">b</font>,20-ЕПОКСИ-1-ГІДРОКСІ-9-ОКСО-19-НОР-ЦИКЛОПРОПА[G]ТАКС-11-ЕН-13<font face="Symbol">a</font>-ІЛУ ТА СПОСІБ ЙОГО ОДЕРЖАННЯ
SK790-98A SK282512B6 (sk) 1995-12-14 1996-12-09 Dihydrát 4,10beta-diacetoxy-2alfa-benzoyloxy-5beta,20-epoxy-1- hydroxy-9-oxo-19-nor-cyklopropa[g]tax-11-én-13alfa-yl-(2R,3S)- 3-terc-butoxykarbonylamino-2-hydroxy-3-fenylpropionátu a spôsob jeho prípravy
IL12476696A IL124766A (en) 1995-12-14 1996-12-09 4, 10beta-diacetoxy-2alpha-benzyloxy-5beta, 20-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa ¬g¾ tax-11-ene-13alpha - yl (2r, 3s) -3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate and method for preparing same
EP96941720A EP0876361B1 (fr) 1995-12-14 1996-12-09 Dihydrate du (2r,3s)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate de 4,10beta-diacetoxy-2alpha-benzoyloxy-5beta,20-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa g]tax-11-ene-13alpha-yle, et son procede de preparation
NZ323964A NZ323964A (en) 1995-12-14 1996-12-09 4,10beta-diacetoxy-2alpha-benzoyloxy-5beta,20-epoxy-1-hydroxy-9-oxo-19-nor-cy clopropa[g]tax-11-ene-13alpha-yl
EA199800452A EA000668B1 (ru) 1995-12-14 1996-12-09 ДИГИДРАТ (2R,3S)-3-ТРЕТ-БУТОКСИКАРБОНИЛАМИНО-2-ГИДРОКСИ-3-ФЕНИЛПРОПИОНАТ 4,10β-ДИАЦЕТОКСИ-2α-БЕНЗОИЛОКСИ-5β,20-ЭПОКСИ-1-ГИДРОКСИ-9-ОКСО-19-НОР-ЦИКЛОПРОПА [G] ТАКС-11-ЕН-13α-ИЛА И СПОСОБ ЕГО ПОЛУЧЕНИЯ
HU9904048A HU224962B1 (en) 1995-12-14 1996-12-09 4,10-betha-diacetoxy-2alfa-benzoyloxy-5betha,20-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa[g]tax-11-ene-13alpha-yl (2r,3s)-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate, and method for preparing same
DE69614716T DE69614716T2 (de) 1995-12-14 1996-12-09 Dihydrat von (2r,3s)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionsäure ester von 4,10-beta-diacetoxy-2alpha-benzoyloxy-5beta, 20-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa(g]tax-11-en-13alpha-yl und verfahren zu ihrer herstellung
RO98-01069A RO115880B1 (ro) 1995-12-14 1996-12-09 Derivat de taxol si procedeu pentru prepararea acestuia
AU11013/97A AU713086C (en) 1995-12-14 1996-12-09 4,10beta-diacetoxy-2alpha-benzoyloxy-5beta, 20-epoxy-1- hydroxy-9-oxo-19-norcyclopropa(g)tax-11-en-13alpha-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3- phenylpropionate dihydrate and its process of preparation
JP52179097A JP4059351B2 (ja) 1995-12-14 1996-12-09 ４，１０β―ジアセトキシ―２α―ベンゾイルオキシ―５β，２０―エポキシ―１―ヒドロキシ―９―オキソ―１９―ノルシクロプロパ［ｇ］タクス―１１―エン―１３α―イル（２Ｒ，３Ｓ）―３―ｔｅｒｔ―ブトキシカルボニルアミノ―２―ヒドロキシ―３―フェニルプロピオネート二水和物およびそれの製造方法
CA002236545A CA2236545C (fr) 1995-12-14 1996-12-09 Dihydrate du (2r.3s)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate de 4.10.beta.-diacetoxy-2.alpha.-benzoyloxy-5.beta.,20-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa[g]tax-11-ene-13.alpha.-yle, et son procede de preparation
BR9611957A BR9611957A (pt) 1995-12-14 1996-12-09 Di-hidrato de (2r,3s) -3- terc.- butoxicarbonilamino - 2 -hidroxi - 3 - fenilpropionato de 4,10 beta-diacetoxi - 2 - alfa-benzoiloxi-5beta, 20 - epoxi - 1 - hidroxi - 9 - oco - 19 - nor - ciclopropa[g]tax - 11eno - 13alfa - ila e processo para preparação do mesmo
DK96941720T DK0876361T3 (da) 1995-12-14 1996-12-09 4,10beta-diacetoxy-2alfa-benzoyloxy-5beta,20-epoxy-1-hydroxy-9-oxo-19-norcyclopropa[g]tax-11-en-13alfa-yl-(2R,3S)-3-tert.butoxycarbonylamino-2-hydroxy-3-phenylpropionat-dihydrat og fremgangsmåde til dets fremstilling
AT96941720T ATE204573T1 (de) 1995-12-14 1996-12-09 Dihydrat von (2r,3s)-3-tert-butoxycarbonylamino-2-hydroxy-3- henylpropionsäure ester von 4,10-beta- diacetoxy-2alpha-benzoyloxy-5beta, 20-epoxy-1- hydroxy-9-oxo-19-nor-cyclopropa(g)tax-11-en- 13alpha-yl und verfahren zu ihrer herstellung
PL96327451A PL187613B1 (pl) 1995-12-14 1996-12-09 Dihydrat (2R,3S)-3-tert-butoksykarbonyloamino-2-hydroksy-3-fenylopropionianu 4,10 beta-diacetoksy-2alfa-benzoiloksy-5beta, 20-epoksy-1-hydroksy-9-okso-19-nor-cyklopropa[g]taks-11-en-13 alfa-ylu i sposób jego wytwarzania
NO19982561A NO317356B1 (no) 1995-12-14 1998-06-04 4,10beta-diacetoksy-2alfa-benzoyloksy-5beta,20-epoksy-1-hydroksy-9-okso-19-nor-cyklopropa[G]tax-11-en-13<alfa>-yl (2R,3S)-3-tert-butoksykarbonylamino-2-hydroksy-3-fenylpropionat dihydrat, samt fremstilling derav
US09/367,387 US6150541A (en) 1995-12-14 1998-06-10 4,10-β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-19-norcyclopropa[g]t ax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate and its process of preparation
BG102535A BG63010B1 (bg) 1995-12-14 1998-06-12 Дихидрат на (2r,3s)-3-терц-бутоксикарбониламино-2-хидрокси- 3-фенилпропионат на 4,10 бета-диацетокси-2 алфа-бензоилокси- 5 бета, 20-епокси-1-хидрокси-9-оксо-19-нор-циклопропа/g/ такс-11-ен-13-алфа-ил, и метод за получаването му
GR20010400773T GR3036437T3 (en) 1995-12-14 2001-08-23 4,10-g(b)-DIACETOXY-2-g(a)-BENZOYLOXY-5-g(b),20-EPOXY-1-HYDROXY-9-OXO-19-NOR-CYCLOPROPA G]TAX-11-ENE-13-g(a)-YL (2R,3S)-TERT-BUTOXYCARBONYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE DIHYDRATE, AND METHOD FOR PREPARING SAME

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR95/14841 1995-12-14
FR9514841A FR2742438B1 (fr) 1995-12-14 1995-12-14 Dihydrate du (2r,3s)-3-tert-butoxycarbonylamino-2-hydroxy- 3-phenylpropionate de 4,10beta-diacetoxy-2alpha-benzoyloxy- 5beta,2o-epoxy-1-hydroxy-9-oxo-19-nor-cyclopropa(g)tax-11- ene-13alpha-yle, et son procede de preparation

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US09/367,387 Continuation-In-Part US6150541A (en) 1995-12-14 1998-06-10 4,10-β-diacetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-19-norcyclopropa[g]t ax-11-en-13α-yl (2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-3-phenylpropionate dihydrate and its process of preparation

Publications (1)

Publication Number Publication Date
WO1997021695A1 true WO1997021695A1 (fr) 1997-06-19

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ID=9485512

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/FR1996/001957 Ceased WO1997021695A1 (fr) 1995-12-14 1996-12-09 DIHYDRATE DU (2R,3S)-3-TERT-BUTOXYCARBONYLAMINO-2-HYDROXY-3-PHENYLPROPIONATE DE 4,10β-DIACETOXY-2α-BENZOYLOXY-5β,20-EPOXY-1-HYDROXY-9-OXO-19-NOR-CYCLOPROPA[G]TAX-11-ENE-13α-YLE, ET SON PROCEDE DE PREPARATION

Country Status (37)

Country Link
EP (1) EP0876361B1 (https=)
JP (1) JP4059351B2 (https=)
KR (1) KR100429330B1 (https=)
CN (1) CN101113143A (https=)
AR (1) AR004380A1 (https=)
AT (1) ATE204573T1 (https=)
AU (1) AU713086C (https=)
BG (1) BG63010B1 (https=)
BR (1) BR9611957A (https=)
CA (1) CA2236545C (https=)
CO (1) CO4810227A1 (https=)
CZ (1) CZ288998B6 (https=)
DE (1) DE69614716T2 (https=)
DK (1) DK0876361T3 (https=)
DZ (1) DZ2140A1 (https=)
EA (1) EA000668B1 (https=)
ES (1) ES2162123T3 (https=)
FR (1) FR2742438B1 (https=)
GR (1) GR3036437T3 (https=)
HU (1) HU224962B1 (https=)
IL (1) IL124766A (https=)
IN (1) IN185809B (https=)
MY (1) MY115886A (https=)
NO (1) NO317356B1 (https=)
NZ (1) NZ323964A (https=)
OA (1) OA11012A (https=)
PL (1) PL187613B1 (https=)
PT (1) PT876361E (https=)
RO (1) RO115880B1 (https=)
SK (1) SK282512B6 (https=)
TN (1) TNSN96157A1 (https=)
TR (1) TR199801087T2 (https=)
TW (1) TW358093B (https=)
UA (1) UA55401C2 (https=)
UY (1) UY24387A1 (https=)
WO (1) WO1997021695A1 (https=)
ZA (1) ZA9610200B (https=)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102851740A (zh) * 2011-06-30 2013-01-02 复旦大学 一种氟代多烯紫杉醇晶体及其制备方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2698871B1 (fr) * 1992-12-09 1995-02-24 Rhone Poulenc Rorer Sa Nouveau taxoïdes, leur préparation et les compositions pharmaceutiques qui les contiennent.

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
ACTA CRISTALLOGR. SECT. C:CRYSTAL STRUCTURE COMMUN., vol. C46, no. 5, 1990, ENGL., pages 781 - 784 *
CHEMICAL ABSTRACTS, vol. 113, no. 75, 1990, Columbus, Ohio, US; abstract no. 142641k, GUERITTE-VOGELEIN ET AL.: "structure of a synthetic taxol precursor." page 723; column 2; XP002007111 *

Also Published As

Publication number Publication date
ZA9610200B (en) 1997-06-23
CA2236545C (fr) 2007-01-30
CA2236545A1 (fr) 1997-06-19
UA55401C2 (uk) 2003-04-15
EP0876361A1 (fr) 1998-11-11
FR2742438A1 (fr) 1997-06-20
JP2000501722A (ja) 2000-02-15
HUP9904048A1 (hu) 2001-04-28
NO982561L (no) 1998-06-04
TW358093B (en) 1999-05-11
EP0876361B1 (fr) 2001-08-22
PT876361E (pt) 2001-11-30
MY115886A (en) 2003-09-30
SK282512B6 (sk) 2002-10-08
BG63010B1 (bg) 2001-01-31
ATE204573T1 (de) 2001-09-15
HU224962B1 (en) 2006-04-28
AR004380A1 (es) 1998-11-04
BR9611957A (pt) 1999-02-17
NO317356B1 (no) 2004-10-18
DE69614716D1 (de) 2001-09-27
HUP9904048A3 (en) 2001-08-28
DK0876361T3 (da) 2001-10-08
MX9804604A (es) 1998-10-31
SK79098A3 (en) 1998-11-04
UY24387A1 (es) 2001-08-27
IL124766A0 (en) 1999-01-26
OA11012A (fr) 2003-03-06
BG102535A (en) 1999-08-31
IL124766A (en) 2001-03-19
KR19990072107A (ko) 1999-09-27
JP4059351B2 (ja) 2008-03-12
CZ183098A3 (cs) 1998-09-16
CO4810227A1 (es) 1999-06-30
RO115880B1 (ro) 2000-07-28
FR2742438B1 (fr) 1998-01-16
NO982561D0 (no) 1998-06-04
ES2162123T3 (es) 2001-12-16
PL187613B1 (pl) 2004-08-31
TR199801087T2 (xx) 1998-09-21
KR100429330B1 (ko) 2005-01-13
AU1101397A (en) 1997-07-03
IN185809B (https=) 2001-05-05
EA000668B1 (ru) 2000-02-28
TNSN96157A1 (fr) 2005-03-15
NZ323964A (en) 2000-01-28
PL327451A1 (en) 1998-12-07
CN101113143A (zh) 2008-01-30
EA199800452A1 (ru) 1998-12-24
DZ2140A1 (fr) 2002-07-23
CZ288998B6 (cs) 2001-10-17
DE69614716T2 (de) 2002-06-27
AU713086B2 (en) 1999-11-25
AU713086C (en) 2002-09-19
GR3036437T3 (en) 2001-11-30

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