WO2001028497A3 - Novel bicyclic cannabinoid agonists for the cannabinoid receptor - Google Patents

Novel bicyclic cannabinoid agonists for the cannabinoid receptor Download PDF

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Publication number
WO2001028497A3
WO2001028497A3 PCT/US2000/041238 US0041238W WO0128497A3 WO 2001028497 A3 WO2001028497 A3 WO 2001028497A3 US 0041238 W US0041238 W US 0041238W WO 0128497 A3 WO0128497 A3 WO 0128497A3
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WO
WIPO (PCT)
Prior art keywords
cannabinoid
receptor
agonists
novel bicyclic
analogs
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/US2000/041238
Other languages
French (fr)
Other versions
WO2001028497A2 (en
Inventor
Alexandros Makriyannis
Atmaram Khanolkar
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.)
University of Connecticut
Original Assignee
University of Connecticut
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 to JP2001531093A priority Critical patent/JP2004500342A/en
Priority to CA002388503A priority patent/CA2388503A1/en
Priority to AU21135/01A priority patent/AU785033B2/en
Priority to DE60033545T priority patent/DE60033545T2/en
Priority to MXPA02005104A priority patent/MXPA02005104A/en
Priority to US10/110,812 priority patent/US6943266B1/en
Application filed by University of Connecticut filed Critical University of Connecticut
Priority to EP00984533A priority patent/EP1224155B1/en
Publication of WO2001028497A2 publication Critical patent/WO2001028497A2/en
Publication of WO2001028497A3 publication Critical patent/WO2001028497A3/en
Anticipated expiration legal-status Critical
Priority to US11/053,132 priority patent/US7335688B2/en
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/703—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups
    • C07C49/743—Unsaturated compounds containing a keto groups being part of a ring containing hydroxy groups having unsaturation outside the rings, e.g. humulones, lupulones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • 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
    • A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
    • 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
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • 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
    • A61P25/08—Antiepileptics; Anticonvulsants
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • 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
    • A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
    • A61P25/16—Anti-Parkinson drugs
    • 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
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/12—Antivirals
    • A61P31/14—Antivirals for RNA viruses
    • A61P31/18—Antivirals for RNA viruses for HIV
    • 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
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    • 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
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    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/657—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings
    • C07C49/665—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system
    • C07C49/67—Unsaturated compounds containing a keto groups being part of a ring containing six-membered aromatic rings a keto group being part of a condensed ring system having two rings, e.g. tetralones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/753—Unsaturated compounds containing a keto groups being part of a ring containing ether groups, groups, groups, or groups

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
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  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Pharmacology & Pharmacy (AREA)
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  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Biomedical Technology (AREA)
  • Pain & Pain Management (AREA)
  • Ophthalmology & Optometry (AREA)
  • Psychology (AREA)
  • Hospice & Palliative Care (AREA)
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  • Heart & Thoracic Surgery (AREA)
  • Obesity (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
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  • Molecular Biology (AREA)
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  • Diabetes (AREA)
  • Hematology (AREA)
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  • Tropical Medicine & Parasitology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • AIDS & HIV (AREA)
  • Endocrinology (AREA)
  • Otolaryngology (AREA)

Abstract

Novel polycyclic cannabinoid analogs are presented which have preferentially high affinities for the cannabinoid CB2 receptor sites. The improved receptor affinity makes these analogs therapeutically useful as medications in individuals and animals for treatment of pain, glaucoma, epilepsy, nausea associated with chemotherapy.
PCT/US2000/041238 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for the cannabinoid receptor Ceased WO2001028497A2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
CA002388503A CA2388503A1 (en) 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for the cannabinoid receptor
AU21135/01A AU785033B2 (en) 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for the cannabinoid receptor
DE60033545T DE60033545T2 (en) 1999-10-18 2000-10-18 NEW BICYCLIC CANNABINOID AGONISTS FOR THE CANNABINOID RECEPTOR
MXPA02005104A MXPA02005104A (en) 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for the cannabinoid receptor.
US10/110,812 US6943266B1 (en) 1999-10-18 2000-10-18 Bicyclic cannabinoid agonists for the cannabinoid receptor
JP2001531093A JP2004500342A (en) 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for cannabinoid receptors
EP00984533A EP1224155B1 (en) 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for the cannabinoid receptor
US11/053,132 US7335688B2 (en) 1999-10-18 2005-02-08 Bicyclic cannabinoid agonists for the cannabinoid receptor

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US16023999P 1999-10-18 1999-10-18
US60/160,239 1999-10-18

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US10110812 A-371-Of-International 2000-10-18
US11/053,132 Continuation US7335688B2 (en) 1999-10-18 2005-02-08 Bicyclic cannabinoid agonists for the cannabinoid receptor

Publications (2)

Publication Number Publication Date
WO2001028497A2 WO2001028497A2 (en) 2001-04-26
WO2001028497A3 true WO2001028497A3 (en) 2001-09-13

Family

ID=22576092

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2000/041238 Ceased WO2001028497A2 (en) 1999-10-18 2000-10-18 Novel bicyclic cannabinoid agonists for the cannabinoid receptor

Country Status (8)

Country Link
EP (1) EP1224155B1 (en)
JP (1) JP2004500342A (en)
AU (1) AU785033B2 (en)
CA (1) CA2388503A1 (en)
DE (1) DE60033545T2 (en)
MX (1) MXPA02005104A (en)
WO (1) WO2001028497A2 (en)
ZA (1) ZA200203909B (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7241799B2 (en) 1999-10-18 2007-07-10 University Of Connecticut Cannabimimetic indole derivatives
US7276613B1 (en) 1998-11-24 2007-10-02 University Of Connecticut Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US7285683B2 (en) 2001-07-13 2007-10-23 University Of Connecticut Bicyclic and tricyclic cannabinoids
US7329651B2 (en) 2001-01-26 2008-02-12 University Of Connecticut Cannabimimetic ligands
US7335688B2 (en) 1999-10-18 2008-02-26 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US7393842B2 (en) 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors
US7589220B2 (en) 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE247097T1 (en) 1998-05-04 2003-08-15 Univ Connecticut ANALGESIC AND IMMUNOMODULATING CANNABINOIDS
US7897598B2 (en) 1998-06-09 2011-03-01 Alexandros Makriyannis Inhibitors of the anandamide transporter
US7161016B1 (en) 1998-11-24 2007-01-09 University Of Connecticut Cannabimimetic lipid amides as useful medications
DE60033834T2 (en) * 1999-10-18 2007-11-15 The University Of Connecticut, Farmington FOR PERIPHERAL CANNABINOID RECEPTORS SELECTIVE LIGANDS
US7119108B1 (en) 1999-10-18 2006-10-10 University Of Connecticut Pyrazole derivatives as cannabinoid receptor antagonists
CA2436133A1 (en) 2001-01-29 2002-08-08 University Of Connecticut Receptor selective cannabimimetic aminoalkylindoles
WO2003007887A2 (en) 2001-07-20 2003-01-30 Merck & Co., Inc. Substituted imidazoles as cannabinoid receptor modulators
WO2003061699A1 (en) * 2001-12-27 2003-07-31 Japan Tobacco, Inc. Remedies for allergic diseases
IL150302A (en) * 2002-01-31 2008-07-08 Naim Menashe Bicyclic cb2 cannabinoid receptor ligands
JP2005523259A (en) * 2002-01-31 2005-08-04 ファーモス コーポレイション Bicyclic CB2 cannabinoid receptor ligand
CA2478338A1 (en) 2002-03-08 2003-09-18 Signal Pharmaceuticals, Inc. Combination therapy for treating, preventing or managing proliferative disorders and cancers
WO2004017922A2 (en) 2002-08-23 2004-03-04 University Of Connecticut Keto cannabinoids with therapeutic indications
CN101076324A (en) * 2004-10-22 2007-11-21 法玛氏公司 Orally active cannabinoid analogs
WO2011009883A1 (en) 2009-07-23 2011-01-27 INSERM (Institut National de la Santé et de la Recherche Médicale) Selective cb2 receptor agonists for use in the prevention or treatment of alcoholic liver disease

Citations (6)

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Publication number Priority date Publication date Assignee Title
US4102902A (en) * 1976-11-10 1978-07-25 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4176233A (en) * 1976-11-10 1979-11-27 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4208351A (en) * 1976-11-10 1980-06-17 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4876276A (en) * 1986-10-24 1989-10-24 Yissum Research Development Co. Of The Hebrew University Of Jerusalem (3S-4S)-7-hydroxy-Δ6 -tetrahydrocannabinols
US5605906A (en) * 1995-03-24 1997-02-25 Merck Frosst Canada, Inc. Cannabinoid receptor agonists
US5948777A (en) * 1997-03-18 1999-09-07 Smithkline Beecham Corporation Cannabinoid receptor agonists

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IL55274A (en) * 1978-08-02 1982-08-31 Yissum Res Dev Co 4-(2,6-dihydroxy-4-(dimethylheptyl)phenyl)substituted 2-pinen-10-ol and pinane derivatives,their preparation and pharmaceutical compositions comprising them
US5434295A (en) * 1994-02-07 1995-07-18 Yissum Research Development Company Neuroprotective pharmaceutical compositions of 4-phenylpinene derivatives and certain novel 4-phenylpinene compounds

Patent Citations (6)

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US4102902A (en) * 1976-11-10 1978-07-25 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4176233A (en) * 1976-11-10 1979-11-27 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4208351A (en) * 1976-11-10 1980-06-17 Eli Lilly And Company Stereoselective preparation of hexahydro dibenzopyranones and intermediates therefor
US4876276A (en) * 1986-10-24 1989-10-24 Yissum Research Development Co. Of The Hebrew University Of Jerusalem (3S-4S)-7-hydroxy-Δ6 -tetrahydrocannabinols
US5605906A (en) * 1995-03-24 1997-02-25 Merck Frosst Canada, Inc. Cannabinoid receptor agonists
US5948777A (en) * 1997-03-18 1999-09-07 Smithkline Beecham Corporation Cannabinoid receptor agonists

Non-Patent Citations (7)

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Title
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 129:276026C, DRAKE ET AL.: "Classical/nonclassical hybrid cannabinoids" XP002939621 *
CHEMICAL ABSTRACTS, Columbus, Ohio, US; abstract no. 87:39223W, ARCHER ET AL.: "Cannabinoids. 3. Synthetic approaches to 9-ketocannabinoids. Total synthesis of nabilone" XP002939620 *
HUFFMAN ET AL.: "Synthesis of 5', 11-dihydroxy- 8-tetrahydrocannabinol", TETRAHEDRON, vol. 53, no. 39, 1997, pages 13295 - 13306, XP002939619 *
HUFFMAN ET AL.: "Synthesis of both enantiomers of nabilone from a common intermediate. Enantiodivergent synthesis of cannabinoids", J. ORG. CHEM., vol. 56, no. 6, 1991, pages 2081 - 2086, XP002939618 *
J. MED. CHEM., vol. 41, no. 19, 1998, pages 3596 - 3608 *
J. ORG. CHEM., vol. 42, no. 13, 1977, pages 2277 - 2284 *
See also references of EP1224155A4 *

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7589220B2 (en) 1998-06-09 2009-09-15 University Of Connecticut Inhibitors of the anandamide transporter
US7276613B1 (en) 1998-11-24 2007-10-02 University Of Connecticut Retro-anandamides, high affinity and stability cannabinoid receptor ligands
US7241799B2 (en) 1999-10-18 2007-07-10 University Of Connecticut Cannabimimetic indole derivatives
US7335688B2 (en) 1999-10-18 2008-02-26 University Of Connecticut Bicyclic cannabinoid agonists for the cannabinoid receptor
US7329651B2 (en) 2001-01-26 2008-02-12 University Of Connecticut Cannabimimetic ligands
US7285683B2 (en) 2001-07-13 2007-10-23 University Of Connecticut Bicyclic and tricyclic cannabinoids
US7393842B2 (en) 2001-08-31 2008-07-01 University Of Connecticut Pyrazole analogs acting on cannabinoid receptors

Also Published As

Publication number Publication date
AU785033B2 (en) 2006-08-31
WO2001028497A2 (en) 2001-04-26
DE60033545D1 (en) 2007-04-05
EP1224155B1 (en) 2007-02-21
ZA200203909B (en) 2003-11-26
CA2388503A1 (en) 2001-04-26
EP1224155A4 (en) 2005-04-13
MXPA02005104A (en) 2003-09-25
AU2113501A (en) 2001-04-30
JP2004500342A (en) 2004-01-08
DE60033545T2 (en) 2007-10-31
EP1224155A2 (en) 2002-07-24

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