WO2006002763A3 - Substituierte tetrahydroisochinoline als mmp-inhibitoren, verfahren zu ihrer herstellung und ihre verwendung als medikament - Google Patents

Substituierte tetrahydroisochinoline als mmp-inhibitoren, verfahren zu ihrer herstellung und ihre verwendung als medikament Download PDF

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Publication number
WO2006002763A3
WO2006002763A3 PCT/EP2005/006415 EP2005006415W WO2006002763A3 WO 2006002763 A3 WO2006002763 A3 WO 2006002763A3 EP 2005006415 W EP2005006415 W EP 2005006415W WO 2006002763 A3 WO2006002763 A3 WO 2006002763A3
Authority
WO
WIPO (PCT)
Prior art keywords
drags
tetrahydroisochinolines
substituted
production
mmp inhibitors
Prior art date
Application number
PCT/EP2005/006415
Other languages
English (en)
French (fr)
Other versions
WO2006002763A2 (de
Inventor
Armin Hofmeister
Manfred Schudok
Hans Matter
Kristin Breitschopf
Antonio Ugolini
Original Assignee
Sanofi Aventis Deutschland
Armin Hofmeister
Manfred Schudok
Hans Matter
Kristin Breitschopf
Antonio Ugolini
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 Sanofi Aventis Deutschland, Armin Hofmeister, Manfred Schudok, Hans Matter, Kristin Breitschopf, Antonio Ugolini filed Critical Sanofi Aventis Deutschland
Priority to EP05757350A priority Critical patent/EP1763516A2/de
Priority to CA002572125A priority patent/CA2572125A1/en
Priority to BRPI0511323-7A priority patent/BRPI0511323A/pt
Priority to AU2005259633A priority patent/AU2005259633A1/en
Priority to MXPA06014366A priority patent/MXPA06014366A/es
Priority to JP2007518484A priority patent/JP2008504315A/ja
Publication of WO2006002763A2 publication Critical patent/WO2006002763A2/de
Publication of WO2006002763A3 publication Critical patent/WO2006002763A3/de
Priority to IL179974A priority patent/IL179974A0/en
Priority to US11/612,938 priority patent/US20070203118A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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
    • A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
    • A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
    • A61K31/4035—Isoindoles, e.g. phthalimide
    • 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
    • A61K31/47—Quinolines; Isoquinolines
    • A61K31/472—Non-condensed isoquinolines, e.g. papaverine
    • 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
    • A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • 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
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/04—Drugs for skeletal disorders for non-specific disorders of the connective tissue
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P19/00—Drugs for skeletal disorders
    • A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
    • A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
    • 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
    • A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
    • C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Rheumatology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Biomedical Technology (AREA)
  • Epidemiology (AREA)
  • Neurology (AREA)
  • Hospice & Palliative Care (AREA)
  • Pain & Pain Management (AREA)
  • Neurosurgery (AREA)
  • Dermatology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Immunology (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Other In-Based Heterocyclic Compounds (AREA)

Abstract

Die vorliegende Erfindung betrifft Verbindungen der Formel (I), wobei R1, R2, R3, R4, A, n und L und die angegebene Bedeutung haben, und die Verwendung derselben als Arzneimittel zur Prophylaxe und/oder Therapie von Erkrankungen, an deren Verlauf eine verstärkte Aktivität von Matrix-Metalloproteinasen beteiligt ist.
PCT/EP2005/006415 2004-06-30 2005-06-15 Substituierte tetrahydroisochinoline als mmp-inhibitoren, verfahren zu ihrer herstellung und ihre verwendung als medikament WO2006002763A2 (de)

Priority Applications (8)

Application Number Priority Date Filing Date Title
EP05757350A EP1763516A2 (de) 2004-06-30 2005-06-15 Substituierte tetrahydroisochinoline als mmp-inhibitoren, verfahren zu ihrer herstellung und ihre verwendung als medikament
CA002572125A CA2572125A1 (en) 2004-06-30 2005-06-15 Substituted tetrahydroisochinolines used in the form of mmp inhibitors, method for the production and use thereof in the form of drags
BRPI0511323-7A BRPI0511323A (pt) 2004-06-30 2005-06-15 tetraidroisoquinolinas substituìdas usadas na forma de inibidores de mmp, método para a produção e uso das mesmas na forma de drágeas
AU2005259633A AU2005259633A1 (en) 2004-06-30 2005-06-15 Substituted tetrahydroisochinolines used in the form of MMP inhibitors, method for the production and use thereof in the form of drags
MXPA06014366A MXPA06014366A (es) 2004-06-30 2005-06-15 Tetrahidroisoquinolinas sustituidas utilizadas en forma de inhibidores de mpm, metodo para su produccion y su uso en forma de farmacos.
JP2007518484A JP2008504315A (ja) 2004-06-30 2005-06-15 Ｍｍｐ阻害剤の形態で使用される置換テトラヒドロイソキノリン、その製造法および薬剤としての使用
IL179974A IL179974A0 (en) 2004-06-30 2006-12-11 Substituted tetrahydroiso quinolines used in the form of mmp inhibitors, method for the production and use thereof in the form of drugs
US11/612,938 US20070203118A1 (en) 2004-06-30 2006-12-19 Substituted tetrahydroisoquinolines used in the form of mmp inhibitors, method for the production and use thereof in the form of drugs

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004031850.6 2004-06-30
DE102004031850A DE102004031850A1 (de) 2004-06-30 2004-06-30 Substituirte Tetrahydroisochinoline als MMP-Inhibitoren, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikament

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US11/612,938 Continuation US20070203118A1 (en) 2004-06-30 2006-12-19 Substituted tetrahydroisoquinolines used in the form of mmp inhibitors, method for the production and use thereof in the form of drugs

Publications (2)

Publication Number Publication Date
WO2006002763A2 WO2006002763A2 (de) 2006-01-12
WO2006002763A3 true WO2006002763A3 (de) 2006-03-16

Family

ID=34971773

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2005/006415 WO2006002763A2 (de) 2004-06-30 2005-06-15 Substituierte tetrahydroisochinoline als mmp-inhibitoren, verfahren zu ihrer herstellung und ihre verwendung als medikament

Country Status (15)

Country Link
US (1) US20070203118A1 (de)
EP (1) EP1763516A2 (de)
JP (1) JP2008504315A (de)
KR (1) KR20070026679A (de)
CN (1) CN101006059A (de)
AU (1) AU2005259633A1 (de)
BR (1) BRPI0511323A (de)
CA (1) CA2572125A1 (de)
DE (1) DE102004031850A1 (de)
IL (1) IL179974A0 (de)
MX (1) MXPA06014366A (de)
PE (1) PE20060458A1 (de)
TW (1) TW200612940A (de)
UY (1) UY28993A1 (de)
WO (1) WO2006002763A2 (de)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004031620A1 (de) * 2004-06-30 2006-02-02 Sanofi-Aventis Deutschland Gmbh 4-Trifluormethoxyphenoxybenzol-4`-sulfonsäuren, Verfahren zu ihrer Herstellung und Verwendung in Arzneimitteln
DE102005015040A1 (de) * 2005-03-31 2006-10-05 Sanofi-Aventis Deutschland Gmbh Substituierte Tetrahydroisochinoline als MMP-Inhibitoren, Verfahren zu ihrer Herstellung und ihre Verwendung als Medikament
GB0706072D0 (en) 2007-03-28 2007-05-09 Sterix Ltd Compound
AU2016226340B2 (en) * 2015-03-02 2019-11-07 Amgen Inc. Bicyclic ketone sulfonamide compounds
TWI650313B (zh) * 2017-09-08 2019-02-11 財團法人國家衛生研究院 雜環化合物及其用途
US10597378B2 (en) 2017-09-08 2020-03-24 National Health Research Institutes Tetrahydroisoquinolines for use as MOR/NOP dual agonists
CN110835639B (zh) * 2018-08-16 2021-08-10 苏州同力生物医药有限公司 一种制备(s)-1,2,3,4-四氢异喹啉-1-甲酸及其衍生物的方法

Citations (2)

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Publication number Priority date Publication date Assignee Title
WO1997018194A1 (de) * 1995-11-13 1997-05-22 Hoechst Aktiengesellschaft CYCLISCHE UND HETEROCYCLISCHE N-SUBSTITUIERTE α-IMINOHYDROXAM- UND CARBONSÄUREN
WO2005030728A1 (de) * 2003-09-27 2005-04-07 Sanofi-Aventis Deutschland Gmbh Bicyclische iminosäurederivate als inhibitoren von matrix-metalloproteinasen

Family Cites Families (3)

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DE19542189A1 (de) * 1995-11-13 1997-05-15 Hoechst Ag Cyclische N-substituierte alpha-Iminohydroxamsäuren
WO2003016248A2 (en) * 2001-08-17 2003-02-27 Bristol-Myers Squibb Company Patent Department Bicyclic hydroxamates as inhibitors of matrix metalloproteinases and/or tnf-$g(a) converting enzyme (tace)
US7205315B2 (en) * 2003-09-27 2007-04-17 Sanofi-Aventis Deutschland Gmbh Bicyclic imino acid derivatives as inhibitors of matrix metalloproteinases

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
WO1997018194A1 (de) * 1995-11-13 1997-05-22 Hoechst Aktiengesellschaft CYCLISCHE UND HETEROCYCLISCHE N-SUBSTITUIERTE α-IMINOHYDROXAM- UND CARBONSÄUREN
WO2005030728A1 (de) * 2003-09-27 2005-04-07 Sanofi-Aventis Deutschland Gmbh Bicyclische iminosäurederivate als inhibitoren von matrix-metalloproteinasen

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Title
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; MA, DAWEI ET AL: "Preparation of 2-arylsulfonyltetrahydroisoquinoline hydroximic acid derivs. as matrix metalloproteinase inhibitors", XP002345111, retrieved from STN Database accession no. 2003:779616 *
KAELLBLAD, PER ET AL: "Receptor Flexibility in the in Silico Screening of Reagents in the S1' Pocket of Human Collagenase", JOURNAL OF MEDICINAL CHEMISTRY , 47(11), 2761-2767 CODEN: JMCMAR; ISSN: 0022-2623, 20 May 2004 (2004-05-20), XP002356826 *
KANG, IOU-JIUN ET AL: "Synthesis of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates by Pictet-Spengler condensation using phenyliodine(III) bis(trifluoroacetate)", HETEROCYCLES , 57(1), 1-4 CODEN: HTCYAM; ISSN: 0385-5414, 2002, XP008052601 *
KOHNO, HARUMICHI ET AL: "A novel cyclization of electron deficient N-benzenesulfonyl-.beta.- phenethylamines using ethyl chloro(methylthio)acetate. Synthesis of ethyl 1,2,3,4-tetrahydroisoquinoline-1-carboxylates", HETEROCYCLES , 42(1), 141-4 CODEN: HTCYAM; ISSN: 0385-5414, 1996, XP008052599 *
KOHNO, HARUMICHI ET AL: "A novel synthesis of isoquinolines containing an electron withdrawing substituent", HETEROCYCLES , 51(1), 103-117 CODEN: HTCYAM; ISSN: 0385-5414, 1999, XP008052600 *
LEE, CHAI HO ET AL: "Intra- and intermolecular .alpha.-sulfamidoalkylation reactions", JOURNAL OF ORGANIC CHEMISTRY , 55(25), 6098-104 CODEN: JOCEAH; ISSN: 0022-3263, 1990, XP002345109 *
LUKANOV, LUDMIL K. ET AL: "Synthesis of 2-acyltetrahydroisoquinolines and 2-acyl-1,2,3,4- tetrahydro-1,2-benzothiazine-1,1-diones by electrophilic substitution reactions of N-acyl-2-phenylethylamines", SYNTHETIC COMMUNICATIONS , 28(12), 2137-2147 CODEN: SYNCAV; ISSN: 0039-7911, 1998, XP008052591 *
MA, DAWEI ET AL: "Tetrahydroisoquinoline based sulfonamide hydroxamates as potent matrix metalloproteinase inhibitors", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS , 14(1), 47-50 CODEN: BMCLE8; ISSN: 0960-894X, 5 January 2004 (2004-01-05), XP002345108 *
SILVEIRA, CLAUDIO C. ET AL: "Pictet-Spengler condensation of N-sulfonyl-.beta.-phenethylamines with .alpha.-chloro-.alpha.-phenylselenoesters. New synthesis of 1,2,3,4-tetrahydroisoquinoline-1-carboxylates", TETRAHEDRON LETTERS , 40(27), 4969-4972 CODEN: TELEAY; ISSN: 0040-4039, 1999, XP004169372 *
WANG, HUEY-MIN ET AL: "Ytterbium triflate-catalysed synthesis of ethyl 1,2,3,4- tetrahydroisoquinoline-1-carboxylates using ethyl chloro(phenylselanyl)acetate", HETEROCYCLES , 60(8), 1899-1905 CODEN: HTCYAM; ISSN: 0385-5414, 2003, XP008052602 *

Also Published As

Publication number Publication date
CA2572125A1 (en) 2006-01-12
AU2005259633A1 (en) 2006-01-12
KR20070026679A (ko) 2007-03-08
EP1763516A2 (de) 2007-03-21
PE20060458A1 (es) 2006-05-29
UY28993A1 (es) 2006-01-31
CN101006059A (zh) 2007-07-25
JP2008504315A (ja) 2008-02-14
IL179974A0 (en) 2007-05-15
US20070203118A1 (en) 2007-08-30
MXPA06014366A (es) 2007-03-08
BRPI0511323A (pt) 2007-12-04
WO2006002763A2 (de) 2006-01-12
TW200612940A (en) 2006-05-01
DE102004031850A1 (de) 2006-01-26

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