IL138563A0 - Novel cephalotaxane derivatives and process for their preparation - Google Patents

Novel cephalotaxane derivatives and process for their preparation

Info

Publication number: IL138563A0
Authority: IL; Israel
Prior art keywords: harringtonines; content; synthetic; natural; novel
Prior art date: 1998-03-20

Application number

IL13856399A

Other languages

English (en)

Original Assignee

Oncopharm Corp

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.)

1998-03-20

Filing date

1999-03-17

Publication date

2001-10-31

1999-03-17 Application filed by Oncopharm Corp filed Critical Oncopharm Corp

2001-10-31 Publication of IL138563A0 publication Critical patent/IL138563A0/xx

Links

238000000034 method Methods 0.000 title abstract 2
230000008569 process Effects 0.000 title abstract 2
HYFHYPWGAURHIV-UHFFFAOYSA-N homoharringtonine Natural products C1=C2CCN3CCCC43C=C(OC)C(OC(=O)C(O)(CCCC(C)(C)O)CC(=O)OC)C4C2=CC2=C1OCO2 HYFHYPWGAURHIV-UHFFFAOYSA-N 0.000 abstract 2
239000012535 impurity Substances 0.000 abstract 2
HAVJATCHLFRDHY-UHFFFAOYSA-N Harringtonine Natural products C1=C2CCN3CCCC43C=C(OC)C(OC(=O)C(O)(CCC(C)(C)O)CC(=O)OC)C4C2=CC2=C1OCO2 HAVJATCHLFRDHY-UHFFFAOYSA-N 0.000 abstract 1
229930013930 alkaloid Natural products 0.000 abstract 1
DSRNKUZOWRFQFO-UHFFFAOYSA-N cephalotaxine Natural products COC1=CC23CCCN2CCc4cc5OCOc5cc4C3=C1O DSRNKUZOWRFQFO-UHFFFAOYSA-N 0.000 abstract 1
238000002512 chemotherapy Methods 0.000 abstract 1
238000007813 chromatographic assay Methods 0.000 abstract 1
150000001875 compounds Chemical class 0.000 abstract 1
230000032050 esterification Effects 0.000 abstract 1
238000005886 esterification reaction Methods 0.000 abstract 1
238000007306 functionalization reaction Methods 0.000 abstract 1
230000008570 general process Effects 0.000 abstract 1
HAVJATCHLFRDHY-JZTSUELASA-N harringtonine Chemical compound C1=C2CCN3CCC[C@]43C=C(OC)[C@@H](OC(=O)[C@](O)(CCC(C)(C)O)CC(=O)OC)[C@@H]4C2=CC2=C1OCO2 HAVJATCHLFRDHY-JZTSUELASA-N 0.000 abstract 1
HYFHYPWGAURHIV-JFIAXGOJSA-N omacetaxine mepesuccinate Chemical compound C1=C2CCN3CCC[C@]43C=C(OC)[C@@H](OC(=O)[C@@](O)(CCCC(C)(C)O)CC(=O)OC)[C@H]4C2=CC2=C1OCO2 HYFHYPWGAURHIV-JFIAXGOJSA-N 0.000 abstract 1
229960002230 omacetaxine mepesuccinate Drugs 0.000 abstract 1
239000002243 precursor Substances 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
- A61P33/06—Antimalarials
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/02—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
- C07C57/13—Dicarboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/48—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- 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
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- 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
- 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
- C07D305/02—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D305/04—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D305/08—Heterocyclic compounds containing four-membered rings having one oxygen atom as the only ring hetero atoms not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
- C07D453/04—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems having a quinolyl-4, a substituted quinolyl-4 or a alkylenedioxy-quinolyl-4 radical linked through only one carbon atom, attached in position 2, e.g. quinine

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Tropical Medicine & Parasitology (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Epoxy Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Pyrane Compounds (AREA)
Cephalosporin Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

IL13856399A 1998-03-20 1999-03-17 Novel cephalotaxane derivatives and process for their preparation IL138563A0 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9803492A FR2776292B1 (fr)	1998-03-20	1998-03-20	Cephalotaxanes porteurs de chaine laterale et leur procede de synthese
PCT/IB1999/000491 WO1999048894A1 (en)	1998-03-20	1999-03-17	Novel cephalotaxane derivatives and process for their preparation

Publications (1)

Publication Number	Publication Date
IL138563A0 true IL138563A0 (en)	2001-10-31

Family

ID=9524328

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13856399A IL138563A0 (en)	1998-03-20	1999-03-17	Novel cephalotaxane derivatives and process for their preparation

Country Status (19)

Country	Link
US (5)	US6831180B1 (de)
EP (1)	EP1064285B1 (de)
JP (3)	JP4942871B2 (de)
KR (1)	KR20010042085A (de)
CN (1)	CN1220692C (de)
AT (1)	ATE289312T1 (de)
AU (1)	AU3270699A (de)
CA (1)	CA2324895A1 (de)
DE (1)	DE69923768T2 (de)
DK (1)	DK1064285T3 (de)
ES (1)	ES2237144T3 (de)
FR (1)	FR2776292B1 (de)
HU (1)	HUP0101375A3 (de)
IL (1)	IL138563A0 (de)
PL (1)	PL343032A1 (de)
PT (1)	PT1064285E (de)
TR (1)	TR200003613T2 (de)
WO (1)	WO1999048894A1 (de)
ZA (1)	ZA200005018B (de)

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JP5550546B2 (ja) *	2007-04-13	2014-07-16	ケムジェネックス・ファーマシューティカルズ・インコーポレイテッド	経口セファロタキシン剤形
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CN103635476B (zh) *	2011-08-18	2016-03-09	杭州本生药业有限公司	高三尖杉酯碱的酰化衍生物、及其制备方法和应用
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CN102675327B (zh) *	2012-03-01	2014-12-10	南开大学	三尖杉酯碱类似物及制备方法和应用
CN102633806A (zh) *	2012-04-05	2012-08-15	贵州博丰生物科技产业开发有限公司	一种三尖杉酯碱的提取分离方法
WO2015101628A1 (en) *	2013-12-31	2015-07-09	Jean-Pierre Robin	Water soluble crystallin salts of certain harringtonines unambiguously protonated on their alkaloid nitrogen and their use as chemotherapeutic drugs
WO2015128463A1 (en) *	2014-02-28	2015-09-03	Jean-Pierre Robin	Water soluble salts of harringtonine and their pharmaceutical applications
WO2015162217A2 (en) *	2014-04-23	2015-10-29	Jean-Pierre Robin	Crystalline salts of cephalotaxine and their use for its purification including enantiomers
WO2016182850A1 (en) *	2015-05-08	2016-11-17	Albany Molecular Research, Inc.	Methods and intermediates for the preparation of omacetaxine and cephalotaxine derivatives thereof
CN106866690B (zh) *	2015-12-10	2019-10-11	南开大学	三尖杉酯类生物碱、其制备方法和用途
EP3275875A1 (de)	2016-07-28	2018-01-31	INDENA S.p.A.	Dioxolanon-zwischenprodukt zur synthese von homoharringtonin
CN110577506B (zh) *	2018-06-07	2023-04-07	中国科学院上海有机化学研究所	(﹣)-三尖杉碱的酯类衍生物的合成方法及其中间体
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1998
- 1998-03-20 FR FR9803492A patent/FR2776292B1/fr not_active Expired - Lifetime
1999
- 1999-03-16 US US09/270,006 patent/US6831180B1/en not_active Expired - Lifetime
- 1999-03-17 JP JP2000537877A patent/JP4942871B2/ja not_active Expired - Fee Related
- 1999-03-17 IL IL13856399A patent/IL138563A0/xx unknown
- 1999-03-17 DE DE69923768T patent/DE69923768T2/de not_active Expired - Lifetime
- 1999-03-17 DK DK99942587T patent/DK1064285T3/da active
- 1999-03-17 WO PCT/IB1999/000491 patent/WO1999048894A1/en not_active Ceased
- 1999-03-17 HU HU0101375A patent/HUP0101375A3/hu unknown
- 1999-03-17 AT AT99942587T patent/ATE289312T1/de active
- 1999-03-17 PT PT99942587T patent/PT1064285E/pt unknown
- 1999-03-17 KR KR1020007010440A patent/KR20010042085A/ko not_active Withdrawn
- 1999-03-17 ES ES99942587T patent/ES2237144T3/es not_active Expired - Lifetime
- 1999-03-17 TR TR2000/03613T patent/TR200003613T2/xx unknown
- 1999-03-17 PL PL99343032A patent/PL343032A1/xx unknown
- 1999-03-17 CN CNB998060445A patent/CN1220692C/zh not_active Expired - Lifetime
- 1999-03-17 AU AU32706/99A patent/AU3270699A/en not_active Abandoned
- 1999-03-17 CA CA002324895A patent/CA2324895A1/en not_active Abandoned
- 1999-03-17 EP EP99942587A patent/EP1064285B1/de not_active Expired - Lifetime
2000
- 2000-09-20 ZA ZA200005018A patent/ZA200005018B/en unknown
2001
- 2001-03-27 US US09/817,176 patent/US6613900B2/en not_active Expired - Lifetime
2004
- 2004-06-25 US US10/877,067 patent/US7169774B2/en not_active Expired - Lifetime
2006
- 2006-05-25 US US11/440,648 patent/US7842687B2/en not_active Ceased
2009
- 2009-03-16 JP JP2009063260A patent/JP5884005B2/ja not_active Expired - Fee Related
2012
- 2012-10-26 US US13/661,677 patent/USRE45128E1/en not_active Expired - Fee Related
2015
- 2015-03-19 JP JP2015056022A patent/JP6087381B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
USRE45128E1 (en)	2014-09-09
EP1064285B1 (de)	2005-02-16
US7842687B2 (en)	2010-11-30
CA2324895A1 (en)	1999-09-30
US6831180B1 (en)	2004-12-14
AU3270699A (en)	1999-10-18
US20060234999A1 (en)	2006-10-19
US20020045750A1 (en)	2002-04-18
US7169774B2 (en)	2007-01-30
JP2015117251A (ja)	2015-06-25
WO1999048894A1 (en)	1999-09-30
EP1064285A1 (de)	2001-01-03
HUP0101375A2 (hu)	2001-12-28
PT1064285E (pt)	2005-05-31
WO1999048894B1 (en)	1999-11-04
US20050090484A1 (en)	2005-04-28
US6613900B2 (en)	2003-09-02
FR2776292A1 (fr)	1999-09-24
JP4942871B2 (ja)	2012-05-30
CN1220692C (zh)	2005-09-28
JP6087381B2 (ja)	2017-03-01
PL343032A1 (en)	2001-07-30
DK1064285T3 (da)	2005-06-20
DE69923768D1 (de)	2005-03-24
JP2009132735A (ja)	2009-06-18
ES2237144T3 (es)	2005-07-16
ATE289312T1 (de)	2005-03-15
HUP0101375A3 (en)	2002-02-28
CN1300289A (zh)	2001-06-20
JP2002507615A (ja)	2002-03-12
TR200003613T2 (tr)	2001-04-20
ZA200005018B (en)	2001-03-22
JP5884005B2 (ja)	2016-03-15
DE69923768T2 (de)	2006-03-23
KR20010042085A (ko)	2001-05-25
FR2776292B1 (fr)	2004-09-10

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