DE60209734T2 - Tetrahydrochinolin-derivate - Google Patents

Tetrahydrochinolin-derivate Download PDF

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Publication number
DE60209734T2
DE60209734T2 DE60209734T DE60209734T DE60209734T2 DE 60209734 T2 DE60209734 T2 DE 60209734T2 DE 60209734 T DE60209734 T DE 60209734T DE 60209734 T DE60209734 T DE 60209734T DE 60209734 T2 DE60209734 T2 DE 60209734T2
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DE
Germany
Prior art keywords
alkyl
acetyl
phenyl
tetrahydro
milligrams
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
DE60209734T
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German (de)
English (en)
Other versions
DE60209734D1 (de
Inventor
N.V. Organon Nicole Corine Renee VAN STRATEN
N.V. Organon Rudolf Gijsbertus VAN SOMEREN
Organon Laboratories Ltd. Jurgen Newhouse Lanarkshire 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.)
Organon NV
Original Assignee
Akzo Nobel 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 Akzo Nobel NV filed Critical Akzo Nobel NV
Publication of DE60209734D1 publication Critical patent/DE60209734D1/de
Application granted granted Critical
Publication of DE60209734T2 publication Critical patent/DE60209734T2/de
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/38Nitrogen atoms
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00Medicinal preparations containing organic active ingredients
    • A61K31/33Heterocyclic compounds
    • A61K31/395Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435Heterocyclic 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
    • A61K31/47Quinolines; Isoquinolines
    • A61K31/4709Non-condensed quinolines and containing further heterocyclic rings
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/08Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/16Masculine contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; Contraceptives
    • A61P15/18Feminine contraceptives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/06Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/06Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
    • A61P5/08Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/10Drugs for disorders of the endocrine system of the posterior pituitary hormones, e.g. oxytocin, ADH
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/04Heterocyclic 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
    • C07D215/08Heterocyclic 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/20Oxygen atoms
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02Heterocyclic 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
    • C07D215/16Heterocyclic 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
    • C07D215/48Carbon 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)
DE60209734T 2001-07-02 2002-06-25 Tetrahydrochinolin-derivate Expired - Lifetime DE60209734T2 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP01202531 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
DE60209734D1 DE60209734D1 (de) 2006-05-04
DE60209734T2 true DE60209734T2 (de) 2006-08-31

Family

ID=8180574

Family Applications (1)

Application Number Title Priority Date Filing Date
DE60209734T Expired - Lifetime DE60209734T2 (de) 2001-07-02 2002-06-25 Tetrahydrochinolin-derivate

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)

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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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US2686182A (en) * 1950-12-07 1954-08-10 Basf Ag O-hydroxy-dihydro-quinoline carboxylic acids
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
CA2452606C (en) 2011-09-13
EP1406628A1 (en) 2004-04-14
EP1406628B1 (en) 2006-03-08

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