JP2000516577A - デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 - Google Patents
デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途Info
- Publication number
- JP2000516577A JP2000516577A JP10505876A JP50587698A JP2000516577A JP 2000516577 A JP2000516577 A JP 2000516577A JP 10505876 A JP10505876 A JP 10505876A JP 50587698 A JP50587698 A JP 50587698A JP 2000516577 A JP2000516577 A JP 2000516577A
- Authority
- JP
- Japan
- Prior art keywords
- deoxynojirimycin
- salt
- glucosylceramidase
- disease
- ceramide
- 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.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/06—Antianaemics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Hospice & Palliative Care (AREA)
- Hematology (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.スペーサーを介してデオキシノジリマイシンの窒素原子に結合した大きな疎 水性部分を含有していることを特徴とする、デオキシノジリマイシン誘導体また はその塩。 2.該スペーサーが、3から8個の炭素原子からなるポリアルキレン鎖、好まし くは3から6個の炭素原子からなるポリアルキレン鎖、より好ましくは5個の炭 素原子からなるポリアルキレン鎖を含んでなることを特徴とする、請求項1のデ オキシノジリマイシン誘導体またはその塩。 3.該スペーサーが、―(CH2)n―で表される構造を有し、上記構造中のnが3 〜8、好ましくは3〜6、より好ましくは5であることを特徴とする、請求項1 のデオキシノジリマイシン誘導体またはその塩。 4.大きな疎水性部分が、アダマンタンメタノール、コレステロール、β−コレ スタノール、アダマンタノール、及び9−フェナントロールからなる群より選ば れる化合物から誘導されたものであることを特徴とする、請求項1のデオキシノ ジリマイシンの誘導体またはその塩。 5.請求項1のデオキシノジリマイシン誘導体またはその塩を含有する、グルコ シルセラミダーゼの阻害剤。 6.セラミドを介するシグナル伝達系が関与する疾患、特に炎症性疾患を、セラ ミドを介するシグナル伝達系との干渉によって治療するのに用いられる、請求項 1のデオキシノジリマイシン誘導体またはその塩を含有する治療剤。 7.グルコシルセラミダーゼを有する細胞膜におけるグルコシルセラミド濃度の 上昇によって生じ、リソソームのグルコシルセラミド分解能の欠損に起因する疾 患の治療に用いられる、請求項1のデオキシノジリマイシン誘導体またはその塩 を含有する治療剤。 8.請求項1のデオキシノジリマイシン誘導体またはその塩を含有する、リソソ ーム脂質蓄積症の治療剤。 9.請求項1のデオキシノジリマイシン誘導体またはその塩を含有する、ゴーシ ェ病の治療剤。 10.請求項1〜4のいずれかに記載のデオキシノジリマイシン誘導体またはそ の塩と、薬学的に投与可能な担体とを含有してなる医薬組成物。 11.請求項1〜4のいずれかに記載のデオキシノジリマイシン誘導体またはそ の塩の、グルコシルセラミダーゼ阻害剤としての用途。 12.ゴーシェ病などの疾患、特にセラミドを介するシグナル伝達系が関与する 炎症性疾患治療用医薬組成物の製造を目的とする、グルコシルセラミダーゼ阻害 剤の用途。 13.ゴーシェ病などの疾患、特にセラミドを介するシグナル伝達系が関与する 炎症性疾患治療用医薬組成物の製造を目的とする、請求項1〜4のいずれかに記 載のデオキシノジリマイシン誘導体またはその塩の用途。 14.リソソーム脂質蓄積症治療用医薬組成物の製造を目的とする、請求項1〜 4のいずれかに記載のデオキシノジリマイシン誘導体またはその塩の用途。 15.治療に有効な量のグルコシルセラミダーゼ阻害剤を、場合によっては、治 療に有効な量の天然又は組換え体、あるいは修飾又は未修飾のグルコセレブロシ ダーゼと共に、患者に投与することを包含するゴーシェ病患者の治療方法。 16.治療に有効な量の請求項1〜4のいずれかに記載のデ オキシノジリマイシン誘導体またはその塩を、場合によっては、治療に有効な量 の天然又は組換え体、あるいは修飾又は未修飾のグルコセレブロシダーゼと共に 、患者に投与することを包含するゴーシェ病患者の治療方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP96202010.3 | 1996-07-15 | ||
EP96202010 | 1996-07-15 | ||
PCT/NL1997/000411 WO1998002161A1 (en) | 1996-07-15 | 1997-07-14 | Deoxynojirimycin derivatives and their uses as glucosylceramidase inhibitors |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009262461A Division JP2010031062A (ja) | 1996-07-15 | 2009-11-18 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2000516577A true JP2000516577A (ja) | 2000-12-12 |
JP4564108B2 JP4564108B2 (ja) | 2010-10-20 |
Family
ID=8224192
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP50587698A Expired - Lifetime JP4564108B2 (ja) | 1996-07-15 | 1997-07-14 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2009262461A Withdrawn JP2010031062A (ja) | 1996-07-15 | 2009-11-18 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2013208841A Withdrawn JP2014024857A (ja) | 1996-07-15 | 2013-10-04 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2016004873A Withdrawn JP2016056203A (ja) | 1996-07-15 | 2016-01-14 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2017081926A Pending JP2017122133A (ja) | 1996-07-15 | 2017-04-18 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009262461A Withdrawn JP2010031062A (ja) | 1996-07-15 | 2009-11-18 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2013208841A Withdrawn JP2014024857A (ja) | 1996-07-15 | 2013-10-04 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2016004873A Withdrawn JP2016056203A (ja) | 1996-07-15 | 2016-01-14 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
JP2017081926A Pending JP2017122133A (ja) | 1996-07-15 | 2017-04-18 | デオキシノジリマイシン誘導体及び該誘導体のグルコシルセラミダーゼ阻害剤としての用途 |
Country Status (9)
Country | Link |
---|---|
US (1) | US6177447B1 (ja) |
EP (1) | EP0912179B1 (ja) |
JP (5) | JP4564108B2 (ja) |
AT (1) | ATE322900T1 (ja) |
AU (1) | AU732552B2 (ja) |
CA (1) | CA2260790C (ja) |
DE (1) | DE69735669T2 (ja) |
IL (1) | IL128036A (ja) |
WO (1) | WO1998002161A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007509926A (ja) * | 2003-10-29 | 2007-04-19 | マクロジーメ ビー.ブイ. | デオキシノジリマイシン類似体、及びグルコシルセラミダーゼ阻害剤としてのその使用 |
JP2007512253A (ja) * | 2003-11-12 | 2007-05-17 | アミカス セラピューティックス インコーポレイテッド | ゴーシェ病を治療するための、ヒドロキシピペリジン誘導体 |
JP2015518896A (ja) * | 2012-06-06 | 2015-07-06 | ユニザー ヴィロロジー,エルエルシー | 新規イミノ糖およびそれらの用途 |
Families Citing this family (29)
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US6098631A (en) * | 1998-01-21 | 2000-08-08 | The Regents Of The University Of Michigan | Compositions and methods for treating autoimmune disease |
US6274597B1 (en) | 1998-06-01 | 2001-08-14 | Mount Sinai School Of Medicine Of New York University | Method of enhancing lysosomal α-Galactosidase A |
US6610703B1 (en) | 1998-12-10 | 2003-08-26 | G.D. Searle & Co. | Method for treatment of glycolipid storage diseases |
GB0100889D0 (en) | 2001-01-12 | 2001-02-21 | Oxford Glycosciences Uk Ltd | Compounds |
GB9909064D0 (en) * | 1999-04-20 | 1999-06-16 | Oxford Glycosciences Uk Ltd | Therapies |
GB9909066D0 (en) * | 1999-04-20 | 1999-06-16 | Oxford Glycosciences Uk Ltd | Therapies |
ATE234626T1 (de) | 1999-07-26 | 2003-04-15 | Searle & Co | Verwendung von langkettigen n-alkyl derivaten von deoxynojirimycin mit glucocerebrosidase enzyme zur herstellung eines medikaments zur behandlung von mit glykolipiden akkumulation zusammenhängenden krankheiten |
US7182953B2 (en) * | 1999-12-15 | 2007-02-27 | Celgene Corporation | Methods and compositions for the prevention and treatment of atherosclerosis restenosis and related disorders |
AU2001236713A1 (en) * | 2000-02-17 | 2001-08-27 | Genzyme Corporation | Methods for treatment of lysosomal storage diseases |
WO2001097829A2 (en) * | 2000-06-19 | 2001-12-27 | Genzyme Corporation | Combination enzyme replacement, gene therapy and small molecule therapy for lysosomal storage diseases |
US7138262B1 (en) * | 2000-08-18 | 2006-11-21 | Shire Human Genetic Therapies, Inc. | High mannose proteins and methods of making high mannose proteins |
US20030124160A1 (en) * | 2001-10-12 | 2003-07-03 | Petrescu Stefana M. | Targeted drug delivery |
EP1534676B1 (en) | 2002-07-17 | 2012-09-12 | Actelion Pharmaceuticals Ltd. | Piperidinetriol derivatives as inhibitors of glycosylceramide synthase |
JP4585851B2 (ja) | 2002-07-17 | 2010-11-24 | アクテリオン ファーマシューティカルズ リミテッド | グルコシルセラミドシンターゼの阻害剤としてのピペリジントリオール誘導体 |
GB0313677D0 (en) | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compound |
GB0313678D0 (en) | 2003-06-13 | 2003-07-16 | Oxford Glycosciences Uk Ltd | Novel compounds |
AU2004283631A1 (en) * | 2003-10-29 | 2005-05-06 | Genzyme Corporation | Use of a deoxynojirimycin derivative or a pharmaceutically salt thereof |
WO2005063706A1 (en) * | 2003-12-23 | 2005-07-14 | Macrozyme Dnm B.V. | Synthesis of nojirimycins |
US20090111812A1 (en) * | 2004-06-14 | 2009-04-30 | Musc Foundation For Research Development | Methods for treating inflammatory disorders |
ES2391657T3 (es) | 2006-02-07 | 2012-11-28 | Shire Human Genetic Therapies, Inc. | Composiciones estabilizadas de proteínas que tienen un resto tiol libre |
US8410081B2 (en) | 2006-04-24 | 2013-04-02 | Academisch Medisch Centrum | Treatment of cystic fibrosis |
US8546369B2 (en) * | 2008-05-30 | 2013-10-01 | Northern Innovations Holding Corp. | Salts of creatine imino sugar amides |
US20100248365A1 (en) * | 2009-03-27 | 2010-09-30 | Zacharon Pharmaceuticals, Inc. | Ganglioside biosynthesis modulators |
RU2733466C2 (ru) | 2009-07-28 | 2020-10-01 | Шайр Хьюман Дженетик Терапиз | Композиции и способы для лечения болезни гоше |
US9453847B2 (en) | 2010-07-19 | 2016-09-27 | Shire Human Genetic Therapies, Inc. | Mannose receptor C type 1 (MRC1) codon optimized cell line and uses thereof |
KR20140138850A (ko) | 2012-03-02 | 2014-12-04 | 샤이어 휴먼 지네틱 테라피즈 인크. | Iii형 고셔병을 치료하기 위한 조성물 및 방법 |
WO2014017915A2 (en) | 2012-07-27 | 2014-01-30 | Universiteit Utrecht Holding B.V. | Urea and guanidinium derivatives of iminosugars |
DK3122726T3 (en) | 2014-03-27 | 2018-10-08 | Acad Medisch Ct | N- (5 - ((Aryl or heteroaryl) methyloxy) pentyl) -substituted imino sugars as inhibitors of glucosylceramide synthase |
EP3256116B1 (en) * | 2015-02-11 | 2022-08-17 | Icahn School of Medicine at Mount Sinai | Benzenesulfonamide upregulators of npc1 for neimann-pick disease and other lysosomal storage disorders |
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JPS567763A (en) * | 1979-06-27 | 1981-01-27 | Bayer Ag | 22hydroxymethyll3*4*55trihydroxyypiperidine derivative* its manufacture and use |
JPS56133267A (en) * | 1980-02-26 | 1981-10-19 | Bayer Ag | Novel 3,4,5-trihydroxypiperidine compound |
DE3024901A1 (de) * | 1980-07-01 | 1982-01-28 | Bayer Ag, 5090 Leverkusen | Herbizide mittel auf basis von piperidin-derivaten |
JPS61200967A (ja) * | 1985-02-28 | 1986-09-05 | バイエル・アクチエンゲゼルシヤフト | 3,4,5‐トリヒドロキシピペリジン類、その製法および用途 |
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US4880902A (en) | 1987-08-27 | 1989-11-14 | Shell Oil Company | Copolymerization of carbon monoxide and olefin with diphosphine having heterocyclic substituents as catalyst |
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-
1997
- 1997-07-14 EP EP97930879A patent/EP0912179B1/en not_active Expired - Lifetime
- 1997-07-14 US US09/230,005 patent/US6177447B1/en not_active Expired - Lifetime
- 1997-07-14 AU AU34647/97A patent/AU732552B2/en not_active Expired
- 1997-07-14 IL IL12803697A patent/IL128036A/xx not_active IP Right Cessation
- 1997-07-14 DE DE69735669T patent/DE69735669T2/de not_active Expired - Lifetime
- 1997-07-14 WO PCT/NL1997/000411 patent/WO1998002161A1/en active IP Right Grant
- 1997-07-14 JP JP50587698A patent/JP4564108B2/ja not_active Expired - Lifetime
- 1997-07-14 AT AT97930879T patent/ATE322900T1/de not_active IP Right Cessation
- 1997-07-14 CA CA002260790A patent/CA2260790C/en not_active Expired - Lifetime
-
2009
- 2009-11-18 JP JP2009262461A patent/JP2010031062A/ja not_active Withdrawn
-
2013
- 2013-10-04 JP JP2013208841A patent/JP2014024857A/ja not_active Withdrawn
-
2016
- 2016-01-14 JP JP2016004873A patent/JP2016056203A/ja not_active Withdrawn
-
2017
- 2017-04-18 JP JP2017081926A patent/JP2017122133A/ja active Pending
Patent Citations (8)
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---|---|---|---|---|
JPS567763A (en) * | 1979-06-27 | 1981-01-27 | Bayer Ag | 22hydroxymethyll3*4*55trihydroxyypiperidine derivative* its manufacture and use |
JPS56133267A (en) * | 1980-02-26 | 1981-10-19 | Bayer Ag | Novel 3,4,5-trihydroxypiperidine compound |
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JPH02306962A (ja) * | 1989-05-19 | 1990-12-20 | Meiji Seika Kaisha Ltd | 新規n―置換―1―デオキシノジリマイシン誘導体及びそれを含有する癌細胞転移抑制剤 |
JPH04342567A (ja) * | 1990-09-20 | 1992-11-30 | Monsanto Co | N−置換−1−デオキシノジリマイシンの製造方法 |
WO1995022975A1 (en) * | 1994-02-25 | 1995-08-31 | G.D. Searle & Co. | Use of 1-deoxynojirimycin and its derivatives for treating mammals infected with respiratory syncytial virus |
Cited By (5)
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JP2007509926A (ja) * | 2003-10-29 | 2007-04-19 | マクロジーメ ビー.ブイ. | デオキシノジリマイシン類似体、及びグルコシルセラミダーゼ阻害剤としてのその使用 |
JP2012180353A (ja) * | 2003-10-29 | 2012-09-20 | Genzyme Corp | デオキシノジリマイシン類似体、及びグルコシルセラミダーゼ阻害剤としてのその使用 |
JP2007512253A (ja) * | 2003-11-12 | 2007-05-17 | アミカス セラピューティックス インコーポレイテッド | ゴーシェ病を治療するための、ヒドロキシピペリジン誘導体 |
JP4767172B2 (ja) * | 2003-11-12 | 2011-09-07 | アミカス セラピューティックス インコーポレイテッド | ゴーシェ病を治療するための、ヒドロキシピペリジン誘導体 |
JP2015518896A (ja) * | 2012-06-06 | 2015-07-06 | ユニザー ヴィロロジー,エルエルシー | 新規イミノ糖およびそれらの用途 |
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CA2260790C (en) | 2007-01-09 |
JP4564108B2 (ja) | 2010-10-20 |
DE69735669T2 (de) | 2007-03-29 |
IL128036A (en) | 2005-08-31 |
EP0912179B1 (en) | 2006-04-12 |
JP2016056203A (ja) | 2016-04-21 |
CA2260790A1 (en) | 1998-01-22 |
JP2017122133A (ja) | 2017-07-13 |
EP0912179A1 (en) | 1999-05-06 |
ATE322900T1 (de) | 2006-04-15 |
DE69735669D1 (de) | 2006-05-24 |
IL128036A0 (en) | 1999-11-30 |
US6177447B1 (en) | 2001-01-23 |
JP2014024857A (ja) | 2014-02-06 |
AU732552B2 (en) | 2001-04-26 |
WO1998002161A1 (en) | 1998-01-22 |
AU3464797A (en) | 1998-02-09 |
JP2010031062A (ja) | 2010-02-12 |
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