DE69629789D1 - Aminoalkohol Derivate und ein Verfahren zu ihrer Herstellung - Google Patents

Aminoalkohol Derivate und ein Verfahren zu ihrer Herstellung

Info

Publication number
DE69629789D1
DE69629789D1 DE69629789T DE69629789T DE69629789D1 DE 69629789 D1 DE69629789 D1 DE 69629789D1 DE 69629789 T DE69629789 T DE 69629789T DE 69629789 T DE69629789 T DE 69629789T DE 69629789 D1 DE69629789 D1 DE 69629789D1
Authority
DE
Germany
Prior art keywords
alcohol derivative
derivative represented
amino
represented
following formula
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.)
Expired - Lifetime
Application number
DE69629789T
Other languages
English (en)
Other versions
DE69629789T2 (de
Inventor
Masayuki Jinbo
Hidekazu Oyamada
Jinichi Inokuchi
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.)
Seikagaku Corp
Original Assignee
Seikagaku 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.)
Filing date
Publication date
Application filed by Seikagaku Corp filed Critical Seikagaku Corp
Application granted granted Critical
Publication of DE69629789D1 publication Critical patent/DE69629789D1/de
Publication of DE69629789T2 publication Critical patent/DE69629789T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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 hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B53/00—Asymmetric syntheses
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
    • C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C215/04—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated
    • C07C215/06—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic
    • C07C215/18—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being saturated and acyclic with hydroxy groups and at least two amino groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/02—Preparation of carboxylic acid amides from carboxylic acids or from esters, anhydrides, or halides thereof by reaction with ammonia or amines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/16—Preparation of optical isomers
    • C07C231/18—Preparation of optical isomers by stereospecific synthesis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
    • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/36—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/12—Oxygen or sulfur atoms
    • 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
    • C07D211/08—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—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 hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
    • C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/14—The ring being saturated

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
DE69629789T 1995-12-08 1996-12-06 Aminoalkohol Derivate und ein Verfahren zu ihrer Herstellung Expired - Lifetime DE69629789T2 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP34508095 1995-12-08
JP34508095 1995-12-08

Publications (2)

Publication Number Publication Date
DE69629789D1 true DE69629789D1 (de) 2003-10-09
DE69629789T2 DE69629789T2 (de) 2004-07-15

Family

ID=18374152

Family Applications (1)

Application Number Title Priority Date Filing Date
DE69629789T Expired - Lifetime DE69629789T2 (de) 1995-12-08 1996-12-06 Aminoalkohol Derivate und ein Verfahren zu ihrer Herstellung

Country Status (9)

Country Link
US (2) US5907039A (de)
EP (1) EP0782992B1 (de)
KR (1) KR970042525A (de)
CN (1) CN1164530A (de)
AT (1) ATE248828T1 (de)
CA (1) CA2192268C (de)
DE (1) DE69629789T2 (de)
HU (1) HUP9603389A3 (de)
NO (1) NO965193L (de)

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6890949B1 (en) * 1999-07-09 2005-05-10 The Regents Of The University Of Michigan Amino ceramide-like compounds and therapeutic methods of use
US5972928A (en) * 1997-05-21 1999-10-26 Johns Hopkins University Methods for treatment of conditions associated with lactosylceramide
US6407064B2 (en) * 1999-12-06 2002-06-18 Seikagaku Corporation Aminoalcohol derivative and medicament comprising the same
IL153594A0 (en) * 2000-07-13 2003-07-06 Sankyo Co Amino alcohol derivatives and pharmaceutical compositions containing the same
CA2434028C (en) * 2001-01-10 2010-11-09 The Regents Of The University Of Michigan Amino ceramide-like compounds and therapeutic methods of use
ATE555102T1 (de) 2001-07-16 2012-05-15 Genzyme Corp N-acylsphingosinglucosyltransferase-inhibitor
US6835831B2 (en) 2001-11-26 2004-12-28 Genzyme Corporation Diastereoselective synthesis of UDP-glucose: N-acylsphingosine glucosyltransferase inhibitors
US6916802B2 (en) * 2002-04-29 2005-07-12 Genzyme Corporation Amino ceramide-like compounds and therapeutic methods of use
US20060217560A1 (en) * 2002-04-29 2006-09-28 Shayman James A Amino ceramide-like compounds and therapeutic methods of use
US20090111812A1 (en) * 2004-06-14 2009-04-30 Musc Foundation For Research Development Methods for treating inflammatory disorders
CA2581454A1 (en) * 2004-09-23 2006-03-30 Reddy Us Therapeutics, Inc. Novel pyrimidine compounds, process for their preparation and compositions containing them
JP2008519840A (ja) * 2004-11-10 2008-06-12 ジェンザイム・コーポレイション 糖尿病の処置方法
JP5042040B2 (ja) * 2005-01-26 2012-10-03 アラーガン、インコーポレイテッド 鎮痛活性および／または免疫賦活活性を有する１−アリール−１−ヒドロキシ−２，３−ジアミノ−プロピルアミン、１−ヘテロアリール−１−ヒドロキシ−２，３−ジアミノ−プロピルアミンおよび関連化合物
ES2546181T3 (es) 2006-05-09 2015-09-21 Genzyme Corporation Métodos de tratar la enfermedad del hígado graso mediante inhibición de la síntesis de glucoesfingolípidos
WO2008109287A1 (en) * 2007-03-06 2008-09-12 Allergan, Inc. Methods for treating cognitive disorders using 1-benzyl-1-hydroxy-2,3-diamino-propyl amines, 3-benzyl-3-hydroxy-2-amino-propionic acid amides and related compounds
US9314466B2 (en) 2007-03-06 2016-04-19 Allergan, Inc. Methods for treating cognitive disorders using 1-benzyl-1-hydroxy-2,3-diamino-propyl amines, 3-benzyl-3-hydroxy-2-amino-propionic acid amides and related compounds
WO2008109285A1 (en) 2007-03-06 2008-09-12 Allergan, Inc. Methods for treating cognitive disorders
CA2680324A1 (en) * 2007-03-06 2008-09-12 John E. Donello Methods for treating cognitive disorders using 3-aryl-3-hydroxy-2-amino-propionic acid amides, 3-heteroaryl-3-hydroxy-2-amino-propionic acid amides and related compounds
US20100105687A1 (en) * 2007-03-06 2010-04-29 Allergan, Inc. Methods for treating cognitive disorders using 1-aryl-1-hydroxy-2,3-diamino-propyl amines, 1-heteroaryl-1-hydroxy-2,3-diamino-propyl amines and related compounds
EP2167485B1 (de) * 2007-05-31 2015-09-30 Genzyme Corporation Glucosylceramidsynthaseinhibitoren vom 2-acylaminopropoanoltyp
MX2010003603A (es) * 2007-10-05 2010-06-02 Genzyme Corp Metodo para el tratamiento de enfermedades de riñon poliquisticas con derivados de ceramida.
CA2731685A1 (en) 2008-07-28 2010-02-04 Genzyme Corporation Glucosylceramide synthase inhibition for the treatment of collapsing glomerulopathy and other glomerular disease
MX2011003517A (es) * 2008-10-03 2011-05-25 Genzyme Corp Inhibidores de la glucosilceramida sintasa tipo 2-acilaminopropanol.
EP3133070B1 (de) 2009-11-27 2019-08-14 Genzyme Corporation Eliglustat (genz 112638) als inhibitor der glucosylceramidsynthase zur verwendung in einem verfahren zur behandlung von fabry's oder gaucher's erkrankung, wobei das verfahren die anpassung der individuellen thearapeutischen dosis an den p-450 stoffwechsel des patienten umfasst
MX2016003486A (es) 2013-09-20 2016-06-28 Biomarin Pharm Inc Inhibidores de glucosilceramida sintasa para el tratamiento de enfermedades.

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5041441A (en) * 1988-04-04 1991-08-20 The Regents Of The University Of Michigan Method of chemotherapy using 1-phenyl-2-decanoylamino-3-morpholino-1-propanol
DE4025330A1 (de) * 1990-08-09 1992-02-13 Basf Ag Lipidderivate und verfahren zu deren herstellung
FR2684102B1 (fr) * 1991-11-21 1994-03-11 Etat Francais Delegue Armement Procede de preparation de polyazidoalcools ainsi que de polyaminoalcools et polyazidothiols derives de ceux-ci.
NZ269847A (en) * 1993-08-13 1996-11-26 Seikagaku Kogyo Co Ltd 2-alkylamino-3-morpholino-1-propanol derivative in a composition for neuronal disease treatment
AU698833B2 (en) * 1994-06-10 1998-11-12 Seikagaku Corporation 2-acylaminopropanol compound and medical composition
BE1008307A3 (fr) 1994-06-16 1996-04-02 Europharmaceuticals Sa Sel de nimesulide hydrosoluble, solution aqueuse le contenant, sa preparation et son utilisation.

Also Published As

Publication number Publication date
EP0782992A1 (de) 1997-07-09
HUP9603389A3 (en) 2000-03-28
HUP9603389A2 (hu) 1998-08-28
NO965193L (no) 1997-06-09
US5907039A (en) 1999-05-25
CA2192268A1 (en) 1997-06-09
ATE248828T1 (de) 2003-09-15
CN1164530A (zh) 1997-11-12
DE69629789T2 (de) 2004-07-15
CA2192268C (en) 2009-05-19
HU9603389D0 (en) 1997-01-28
NO965193D0 (no) 1996-12-05
EP0782992B1 (de) 2003-09-03
KR970042525A (ko) 1997-07-24
US6335444B1 (en) 2002-01-01

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