DE69728986D1 - Substituierte tetrahydronaphthalin- und dihydronaphthalin-derivate mit einer retinoiden und/oder retinoid antagonist-ähnlichen biologischen aktivität - Google Patents

Substituierte tetrahydronaphthalin- und dihydronaphthalin-derivate mit einer retinoiden und/oder retinoid antagonist-ähnlichen biologischen aktivität

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Publication number
DE69728986D1
DE69728986D1 DE69728986T DE69728986T DE69728986D1 DE 69728986 D1 DE69728986 D1 DE 69728986D1 DE 69728986 T DE69728986 T DE 69728986T DE 69728986 T DE69728986 T DE 69728986T DE 69728986 D1 DE69728986 D1 DE 69728986D1
Authority
DE
Germany
Prior art keywords
retinoid
dihydronaphthaline
tetrahydronaphthaline
derivatives
substituted
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 - Fee Related
Application number
DE69728986T
Other languages
English (en)
Other versions
DE69728986T2 (de
Inventor
Vidyasagar Vuligonda
Min Teng
L Beard
T Johnson
Yuan Lin
A Chandraratna
K Song
N Wong
T Duong
J Gillett
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.)
Allergan Inc
Original Assignee
Allergan Inc
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
Priority claimed from US08/667,666 external-priority patent/US5747542A/en
Priority claimed from US08/667,216 external-priority patent/US5808124A/en
Priority claimed from US08/667,215 external-priority patent/US5723666A/en
Priority claimed from US08/667,665 external-priority patent/US5763635A/en
Priority claimed from US08/667,663 external-priority patent/US5773594A/en
Priority claimed from US08/667,664 external-priority patent/US5741896A/en
Application filed by Allergan Inc filed Critical Allergan Inc
Publication of DE69728986D1 publication Critical patent/DE69728986D1/de
Application granted granted Critical
Publication of DE69728986T2 publication Critical patent/DE69728986T2/de
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
    • C07C251/32—Oximes
    • C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C251/44—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups being part of a ring other than a six-membered aromatic ring
    • 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
    • C07C233/00—Carboxylic acid amides
    • C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C233/81—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
    • C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
    • C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
    • C07C245/10—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/63—Esters of sulfonic acids
    • C07C309/64—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms
    • C07C309/65—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to acyclic carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/55—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being unsaturated and containing rings other than 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
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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 ring carbon atoms
    • C07D277/30—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
    • C07D309/10—Oxygen atoms
    • C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
    • 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
    • C07D317/14—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/20—Free hydroxyl or mercaptan
    • 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
    • C07D317/14—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
    • C07D317/24—Radicals substituted by singly bound oxygen or sulfur atoms esterified
    • 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
    • C07D317/14—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 substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D317/26—Radicals substituted by doubly bound oxygen or sulfur atoms or by two such atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
    • C07D333/24—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
    • C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
    • C07D339/08—Six-membered rings
    • 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
    • C07D409/10—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 carbon chain containing aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04—One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
DE69728986T 1996-06-21 1997-06-19 Substituierte tetrahydronaphthalin- und dihydronaphthalin-derivate mit einer retinoiden und/oder retinoid antagonist-ähnlichen biologischen aktivität Expired - Fee Related DE69728986T2 (de)

Applications Claiming Priority (13)

Application Number Priority Date Filing Date Title
US667666 1984-11-02
US667663 1996-06-21
US08/667,666 US5747542A (en) 1996-06-21 1996-06-21 Oxo-substituted tetrahydronaphthalene derivatives having retinold and/or retinoid antagonist-like biological activity
US667215 1996-06-21
US08/667,216 US5808124A (en) 1996-06-21 1996-06-21 O- or S-substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US08/667,215 US5723666A (en) 1996-06-21 1996-06-21 Oxime substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US667664 1996-06-21
US08/667,665 US5763635A (en) 1996-06-21 1996-06-21 Tetrahydronaphthalene derivatives substituted in the 8 position with alkyhidene groups having retinoid and/or retinoid antagonist-like biological activity
US08/667,663 US5773594A (en) 1996-06-21 1996-06-21 Alkyl or aryl substituted dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
US667216 1996-06-21
US667665 1996-06-21
US08/667,664 US5741896A (en) 1996-06-21 1996-06-21 O- or S- substituted tetrahydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity
PCT/US1997/010725 WO1997048672A2 (en) 1996-06-21 1997-06-19 Substituted tetrahydronaphthalene and dihydronaphthalene derivatives having retinoid and/or retinoid antagonist-like biological activity

Publications (2)

Publication Number Publication Date
DE69728986D1 true DE69728986D1 (de) 2004-06-09
DE69728986T2 DE69728986T2 (de) 2005-04-07

Family

ID=27560222

Family Applications (1)

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DE69728986T Expired - Fee Related DE69728986T2 (de) 1996-06-21 1997-06-19 Substituierte tetrahydronaphthalin- und dihydronaphthalin-derivate mit einer retinoiden und/oder retinoid antagonist-ähnlichen biologischen aktivität

Country Status (7)

Country Link
EP (1) EP0915825B1 (de)
JP (1) JP2000511558A (de)
AT (1) ATE265997T1 (de)
AU (1) AU724541B2 (de)
CA (1) CA2258313A1 (de)
DE (1) DE69728986T2 (de)
WO (1) WO1997048672A2 (de)

Families Citing this family (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1998046228A1 (en) 1997-04-11 1998-10-22 Bristol-Myers Squibb Company Retinoid antagonists and uses thereof
DE69917660T2 (de) * 1998-09-24 2005-06-16 Bristol-Myers Squibb Co. 5,6-dihydronaphthalenylderivate mit retinoid-artiger aktivität
AU3958200A (en) * 1999-04-20 2000-11-02 Novo Nordisk A/S New compounds, their preparation and use
US6274608B1 (en) 1999-04-20 2001-08-14 Novo Nordisk A/S Compounds, their preparation and use
US6869959B1 (en) 1999-04-28 2005-03-22 Institute Of Medicinal Molecular Design Inc. Heterocyclic carboxylic acid derivatives
AU2001287901A1 (en) 2000-09-21 2002-04-02 Smithkline Beecham P.L.C. Imidazole derivatives as Raf kinase inhibitors
US7482366B2 (en) 2001-12-21 2009-01-27 X-Ceptor Therapeutics, Inc. Modulators of LXR
WO2003059884A1 (en) 2001-12-21 2003-07-24 X-Ceptor Therapeutics, Inc. Modulators of lxr
PL1651612T3 (pl) 2003-07-22 2012-09-28 Astex Therapeutics Ltd Związki 3,4-pochodne 1h-pirazolu i ich zastosowanie jako kinazy zależne od cyklin (cdk) i modulatory kinazy syntazy glikogenu-3 (gsk-3)
US20050202055A1 (en) * 2004-03-11 2005-09-15 Koichi Shudo, Tokyo, Japan Anti-wrinkle agent
JP5475234B2 (ja) 2005-01-21 2014-04-16 アステックス・セラピューティクス・リミテッド 医薬化合物
MX2007008781A (es) 2005-01-21 2007-09-11 Astex Therapeutics Ltd Compuestos farmaceuticos.
US8404718B2 (en) 2005-01-21 2013-03-26 Astex Therapeutics Limited Combinations of pyrazole kinase inhibitors
AR054425A1 (es) 2005-01-21 2007-06-27 Astex Therapeutics Ltd Sales de adicion de piperidin 4-il- amida de acido 4-(2,6-dicloro-benzoilamino) 1h-pirazol-3-carboxilico.
US8883790B2 (en) 2006-10-12 2014-11-11 Astex Therapeutics Limited Pharmaceutical combinations
US8916552B2 (en) 2006-10-12 2014-12-23 Astex Therapeutics Limited Pharmaceutical combinations
TW200901961A (en) * 2007-02-16 2009-01-16 Synta Pharmaceuticals Corp Substituted fused-ring compounds for inflammation and immune-related uses
US9376391B2 (en) 2012-12-19 2016-06-28 Bayer Cropscience Ag Difluoromethyl-nicotinic-tetrahydronaphthyl carboxamides as fungicides
WO2014095677A1 (en) 2012-12-19 2014-06-26 Bayer Cropscience Ag Difluoromethyl-nicotinic- tetrahydronaphtyl carboxamides
EP3110429A4 (de) 2014-02-27 2018-02-21 Lycera Corporation Adoptive zelltherapie unter verwendung eines agonisten des retinsäurenrezeptor-assoziierten orphanrezeptors gamma und dazugehörige therapeutische verfahren
WO2015171610A2 (en) 2014-05-05 2015-11-12 Lycera Corporation Tetrahydroquinoline sulfonamide and related compounds for use as agonists of rory and the treatment of disease
JP2018515491A (ja) 2015-05-05 2018-06-14 リセラ・コーポレイションＬｙｃｅｒａ Ｃｏｒｐｏｒａｔｉｏｎ ＲＯＲγの作動薬及び疾患の療法として使用するジヒドロ−２Ｈ−ベンゾ［ｂ］［１，４］オキサジンスルホンアミド及び関連化合物
CN107980042B (zh) 2015-06-11 2021-10-08 莱斯拉公司 用作RORγ激动剂和用于治疗疾病的芳基二氢-2H-苯并[b][1,4]噁嗪磺酰胺和相关化合物

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4539154A (en) * 1983-06-15 1985-09-03 Hoffmann-La Roche Inc. Polyene compounds
US5324840A (en) * 1992-06-11 1994-06-28 Allergan, Inc. Method of treatment with compounds having retinoid-like activity and reduced skin toxicity and lacking teratogenic effects
CA2138000A1 (en) * 1994-01-03 1995-07-04 John E. Starrett, Jr. Retinoid-like compounds
WO1995033745A2 (en) * 1994-06-07 1995-12-14 Sri International Novel compounds useful in modulating gene expression of retinoid responsive genes and/or having anti-ap-1 activity
CZ288526B6 (cs) * 1994-08-10 2001-07-11 F. Hoffmann-La Roche Ag Deriváty tetrahydronaftalenu nebo indanu, farmaceutické přípravky na jejich bázi a meziprodukty pro přípravu těchto derivátů
US5514825A (en) * 1994-12-29 1996-05-07 Allergan, Inc. Acetylenes disubstituted with a 5 substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
US5489584A (en) * 1994-12-29 1996-02-06 Allergan, Inc. Acetylenes disubstituted with a 5-amino or substituted 5-amino substituted tetrahydronaphthyl group and with an aryl or heteroaryl group having retinoid-like biological activity
US5559248A (en) * 1995-04-05 1996-09-24 Bristol-Myers Squibb Co. Retinoid-like heterocycles
US5776699A (en) * 1995-09-01 1998-07-07 Allergan, Inc. Method of identifying negative hormone and/or antagonist activities

Also Published As

Publication number Publication date
AU3716297A (en) 1998-01-07
AU724541B2 (en) 2000-09-21
JP2000511558A (ja) 2000-09-05
ATE265997T1 (de) 2004-05-15
WO1997048672A3 (en) 1998-07-16
EP0915825A2 (de) 1999-05-19
CA2258313A1 (en) 1997-12-24
EP0915825B1 (de) 2004-05-06
WO1997048672A2 (en) 1997-12-24
DE69728986T2 (de) 2005-04-07

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