CA2452606C - Tetrahydroquinoline derivatives - Google Patents

Tetrahydroquinoline derivatives Download PDF

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Publication number
CA2452606C
CA2452606C CA2452606A CA2452606A CA2452606C CA 2452606 C CA2452606 C CA 2452606C CA 2452606 A CA2452606 A CA 2452606A CA 2452606 A CA2452606 A CA 2452606A CA 2452606 C CA2452606 C CA 2452606C
Authority
CA
Canada
Prior art keywords
alkyl
phenyl
acetyl
tetrahydro
amino
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
CA2452606A
Other languages
English (en)
French (fr)
Other versions
CA2452606A1 (en
Inventor
Nicole Corine Renee Van Straten
Rudolf Gijsbertus Van Someren
Jurgen Schulz
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.)
Merck Sharp and Dohme BV
Original Assignee
Organon NV
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 Organon NV filed Critical Organon NV
Publication of CA2452606A1 publication Critical patent/CA2452606A1/en
Application granted granted Critical
Publication of CA2452606C publication Critical patent/CA2452606C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms
    • 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
    • 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
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • 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
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/16—Masculine contraceptives
    • 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
    • A61P15/18—Feminine contraceptives
    • 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
    • A61P5/00—Drugs for disorders of the endocrine system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • A61P5/08—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH for decreasing, blocking or antagonising the activity of the anterior pituitary hormones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/10—Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00—Drugs for disorders of the endocrine system
    • A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/04—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms
    • C07D215/08—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to the ring carbon atoms with acylated ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/20—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Endocrinology (AREA)
  • Diabetes (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Pregnancy & Childbirth (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
CA2452606A 2001-07-02 2002-06-25 Tetrahydroquinoline derivatives Expired - Fee Related CA2452606C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP01202531.8 2001-07-02
EP01202531 2001-07-02
PCT/EP2002/007053 WO2003004028A1 (en) 2001-07-02 2002-06-25 Tetrahydroquinoline derivatives

Publications (2)

Publication Number Publication Date
CA2452606A1 CA2452606A1 (en) 2003-01-16
CA2452606C true CA2452606C (en) 2011-09-13

Family

ID=8180574

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2452606A Expired - Fee Related CA2452606C (en) 2001-07-02 2002-06-25 Tetrahydroquinoline derivatives

Country Status (31)

Country Link
US (2) US8058441B2 (enExample)
EP (1) EP1406628B1 (enExample)
JP (1) JP4523273B2 (enExample)
KR (1) KR100908468B1 (enExample)
CN (1) CN1261099C (enExample)
AR (1) AR034669A1 (enExample)
AT (1) ATE319451T1 (enExample)
AU (1) AU2002317848B2 (enExample)
BR (1) BR0210645A (enExample)
CA (1) CA2452606C (enExample)
CY (1) CY1106087T1 (enExample)
CZ (1) CZ20042A3 (enExample)
DE (1) DE60209734T2 (enExample)
DK (1) DK1406628T3 (enExample)
EC (1) ECSP034932A (enExample)
ES (1) ES2260458T3 (enExample)
HR (1) HRP20031080A2 (enExample)
HU (1) HUP0400390A2 (enExample)
IL (1) IL159288A0 (enExample)
IS (1) IS2418B (enExample)
MX (1) MXPA03011908A (enExample)
NO (1) NO325516B1 (enExample)
NZ (1) NZ530198A (enExample)
PE (1) PE20030273A1 (enExample)
PL (1) PL367638A1 (enExample)
PT (1) PT1406628E (enExample)
RU (1) RU2347570C2 (enExample)
SA (1) SA02230260B1 (enExample)
SK (1) SK286759B6 (enExample)
WO (1) WO2003004028A1 (enExample)
ZA (1) ZA200309921B (enExample)

Families Citing this family (46)

* Cited by examiner, † Cited by third party
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HUP0400390A2 (hu) * 2001-07-02 2004-09-28 Akzo Nobel N.V. Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények
AU2003245773A1 (en) * 2002-02-15 2003-09-04 Glaxo Group Limited Vanilloid receptor modulators
FR2836620B1 (fr) * 2002-02-28 2004-04-16 Snecma Services Instrument de projection thermique
SE0200920D0 (sv) * 2002-03-25 2002-03-25 Astrazeneca Ab Novel compounds
TWI306855B (en) * 2002-12-20 2009-03-01 Organon Nv Tetrahydroquinoline derivatives
TWI322012B (en) * 2002-12-20 2010-03-21 Organon Nv Tetrahydroquinoline derivatives
SE0300480D0 (sv) * 2003-02-21 2003-02-21 Astrazeneca Ab Novel compounds
EP1644041A1 (en) * 2003-05-29 2006-04-12 AstraZeneca AB A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine
US20070281931A1 (en) * 2003-05-29 2007-12-06 Nigel Boughton-Smith Pharmaceutical Composition Containing a P2x7 Receptor Antagonist and Methotrexate
EP1633401A1 (en) * 2003-05-29 2006-03-15 AstraZeneca AB A pharmaceutical composition comprising a p2x7-receptor antagonist and a tumour necrosis factor alpha
GB0312609D0 (en) * 2003-06-02 2003-07-09 Astrazeneca Ab Novel compounds
KR100554155B1 (ko) * 2003-06-09 2006-02-22 학교법인 포항공과대학교 금속/반도체 나노막대 이종구조를 이용한 전극 구조물 및그 제조 방법
SE0302139D0 (sv) * 2003-07-28 2003-07-28 Astrazeneca Ab Novel compounds
SE0302192D0 (sv) * 2003-08-08 2003-08-08 Astrazeneca Ab Novel compounds
SE0302488D0 (sv) * 2003-09-18 2003-09-18 Astrazeneca Ab New combination
SA05260265A (ar) * 2004-08-30 2005-12-03 استرازينيكا ايه بي مركبات جديدة
SE0402925D0 (sv) * 2004-11-30 2004-11-30 Astrazeneca Ab Novel Compounds
US7691848B2 (en) 2005-03-02 2010-04-06 Wyeth Pyrrolobenzodiazepine arylcarboxamides and derivatives thereof as follicle-stimulating hormone receptor antagonists
UA92009C2 (ru) 2005-05-04 2010-09-27 Н.В. Органон Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодия
UA92007C2 (ru) * 2005-05-04 2010-09-27 Н.В. Органон Производные 4-фенил-5-оксо-1,4,5,6,7,8-гексагидрохинолина для лечения бесплодности
NZ562541A (en) 2005-05-04 2009-02-28 Organon Nv Dihydropyridine derivatives
UA92008C2 (en) * 2005-05-04 2010-09-27 Н.В. Органон 4-PHENYL-5-OXO-l,4,5,6,7,8-HEXAHYDROQUINOLINE DERIVATIVES AS MEDICAMENTS FOR THE TREATMENT OF INFERTILITY
AU2006247601A1 (en) 2005-05-12 2006-11-23 Wyeth Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (FSH-R) antagonists
CN101208342A (zh) 2005-06-09 2008-06-25 惠氏公司 作为促卵泡激素受体拮抗剂的吡咯并苯并二氮杂䓬吡啶羧酰胺和衍生物
US20070060573A1 (en) * 2005-08-10 2007-03-15 Lars Wortmann Acyltryptophanols
CA2618888A1 (en) * 2005-08-10 2007-02-15 Bayer Schering Pharma Aktiengesellschaft Acyltryptophanols for fertility control
WO2008071453A1 (en) * 2006-12-13 2008-06-19 Bayer Schering Pharma Aktiengesellschaft 1,2-diarylacetylene derivatives of acyltryptophanols
EP1932831A1 (en) * 2006-12-13 2008-06-18 Bayer Schering Pharma Aktiengesellschaft 1,2-Diarylacetylene Derivatives of Acyltryptophanols
TWI410422B (zh) 2007-01-15 2013-10-01 Mitsubishi Tanabe Pharma Corp 縮合四氫喹啉衍生物及其醫藥用途
TW200848021A (en) 2007-03-06 2008-12-16 Wyeth Corp Sulfonylated heterocycles useful for modulation of the progesterone receptor
RU2460727C2 (ru) * 2007-03-22 2012-09-10 Астразенека Аб Хинолиновые производные для лечения воспалительных заболеваний
TW200918058A (en) * 2007-08-31 2009-05-01 Organon Nv TSH receptor antagonizing tetrahydroquinoline compounds
US8106073B2 (en) 2007-11-30 2012-01-31 Astrazeneca Ab Quinoline derivatives 057
RU2359684C1 (ru) * 2008-01-23 2009-06-27 Закрытое акционерное общество "СКАЙ ЛТД" Способ лечения эндометриоза
TW200944523A (en) 2008-02-08 2009-11-01 Organon Nv (Dihydro)pyrrolo[2,1-a]isoquinolines
US20100061976A1 (en) * 2008-07-24 2010-03-11 Searete Llc, A Limited Liability Corporation Of The State Of Delaware Method for treating or preventing osteoporosis by reducing follicle stimulating hormone to cyclic physiological levels in a mammalian subject
TWI461426B (zh) * 2009-05-27 2014-11-21 Merck Sharp & Dohme （二氫）咪唑並異〔５，１－ａ〕喹啉類
US8071587B2 (en) 2009-05-27 2011-12-06 N. V. Organon (Dihydro)imidazoiso[5,1-A]quinolines
US8431564B2 (en) 2009-07-29 2013-04-30 Merck Sharp & Dohme B.V. Ring-annulated dihydropyrrolo[2,1-α]isoquinolines
TW201116531A (en) 2009-07-29 2011-05-16 Organon Nv Ring-annulated dihydropyrrolo[2,1-a]isoquinolines
TW201116515A (en) 2009-07-31 2011-05-16 Organon Nv Dihydrobenzoindazoles
BR112013007907A2 (pt) * 2010-10-08 2016-06-14 N30 Pharmaceuticals Inc novos compostos de quinolina substituída como inibidores de s-nitrosoglutationa reductase
US8546427B2 (en) * 2010-10-20 2013-10-01 Hoffmann-La Roche Inc. Tetrahydroquinoline derivatives
WO2016018553A1 (en) * 2014-07-30 2016-02-04 Henkel IP & Holding GmbH Cure accelerators for anaerobic curable compositions
WO2019089412A1 (en) * 2017-11-01 2019-05-09 Merck Sharp & Dohme Corp. Novel substituted tetrahydroquinolin compounds as indoleamine 2,3-dioxygenase (ido) inhibitors
CN119954701A (zh) * 2024-06-18 2025-05-09 青岛润农化工有限公司 一种丁醚脲的合成方法

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EP0303306B1 (en) 1987-08-08 1993-03-10 Akzo N.V. Contraceptive implant
CZ176197A3 (cs) * 1994-12-22 1998-09-16 Ligand Pharmaceuticals Incorporated Modulátory steroidových receptorů a způsoby jejich přípravy a použití
JP4511042B2 (ja) * 1998-08-07 2010-07-28 メルク セローノ ソシエテ アノニム 不妊症の治療のためのｆｓｈ模倣物
JP2000143636A (ja) * 1998-09-02 2000-05-26 Sumitomo Pharmaceut Co Ltd アミノ誘導体
US6200963B1 (en) * 1999-03-31 2001-03-13 American Home Products Corporation Aryl sulfonic acids as FSH antagonists
HUP0400390A2 (hu) 2001-07-02 2004-09-28 Akzo Nobel N.V. Tetrahidrokinolin-származékok és ezeket tartalmazó gyógyszerkészítmények
TWI322012B (en) * 2002-12-20 2010-03-21 Organon Nv Tetrahydroquinoline derivatives
TWI306855B (en) * 2002-12-20 2009-03-01 Organon Nv Tetrahydroquinoline derivatives

Also Published As

Publication number Publication date
MXPA03011908A (es) 2004-06-03
KR100908468B1 (ko) 2009-07-21
ES2260458T3 (es) 2006-11-01
PL367638A1 (en) 2005-03-07
US8058441B2 (en) 2011-11-15
ECSP034932A (es) 2004-02-26
HUP0400390A2 (hu) 2004-09-28
SK286759B6 (sk) 2009-05-07
CA2452606A1 (en) 2003-01-16
ZA200309921B (en) 2005-03-22
US20040236109A1 (en) 2004-11-25
WO2003004028A1 (en) 2003-01-16
IS7071A (is) 2003-12-11
HK1061810A1 (en) 2004-10-08
CZ20042A3 (en) 2004-04-14
HRP20031080A2 (en) 2004-04-30
DE60209734D1 (de) 2006-05-04
NO20035763L (no) 2003-12-29
CN1529601A (zh) 2004-09-15
KR20040030714A (ko) 2004-04-09
IL159288A0 (en) 2004-06-01
DK1406628T3 (da) 2006-07-03
SA02230260B1 (ar) 2007-03-25
CY1106087T1 (el) 2011-06-08
RU2347570C2 (ru) 2009-02-27
AU2002317848B2 (en) 2006-08-31
BR0210645A (pt) 2004-10-05
SK16342003A3 (sk) 2004-07-07
US20120202996A1 (en) 2012-08-09
RU2004102693A (ru) 2005-06-27
AR034669A1 (es) 2004-03-03
PT1406628E (pt) 2006-06-30
US8258293B2 (en) 2012-09-04
ATE319451T1 (de) 2006-03-15
NZ530198A (en) 2005-11-25
NO325516B1 (no) 2008-06-02
PE20030273A1 (es) 2003-03-21
CN1261099C (zh) 2006-06-28
IS2418B (is) 2008-10-15
JP2004535456A (ja) 2004-11-25
JP4523273B2 (ja) 2010-08-11
EP1406628A1 (en) 2004-04-14
EP1406628B1 (en) 2006-03-08
DE60209734T2 (de) 2006-08-31

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