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
Authority
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
Other languages
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)
  • 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)
  • Chemical Kinetics & Catalysis (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (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)

* Cited by examiner, † Cited by third party
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PT1406628E (pt) * 2001-07-02 2006-06-30 Akzo Nobel Nv Derivados de tera-hidroquinolina
EP2033953A1 (en) * 2002-02-15 2009-03-11 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
EP1644042A1 (en) * 2003-05-29 2006-04-12 AstraZeneca AB A pharmaceutical composition containing a p2x7 receptor antagonist and methotrexate
EP1644041A1 (en) * 2003-05-29 2006-04-12 AstraZeneca AB A pharmaceutical composition comprising a p2x7 antagonist and sulfasalazine
JP2007501270A (ja) * 2003-05-29 2007-01-25 アストラゼネカ・アクチエボラーグ P2X7受容体アンタゴニストおよび腫瘍壊死因子αを含む医薬組成物
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
PL1879866T3 (pl) 2005-05-04 2011-07-29 N V Organon Pochodne dihydropirydynowe
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
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
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
CA2607882A1 (en) 2005-05-12 2006-11-23 Wyeth Pyrrolobenzodiazepines and heterocyclic carboxamide derivatives as follicle stimulating hormone receptor (fsh-r) antagonists
EP1893615A1 (en) 2005-06-09 2008-03-05 Wyeth a Corporation of the State of Delaware Pyrrolobenzodiazepine pyridine carboxamides and derivatives as follicle-stimulating hormone receptor antagonists
JP2009504597A (ja) * 2005-08-10 2009-02-05 バイエル・シエーリング・ファーマ アクチエンゲゼルシャフト アシルトリプトファノール
US20070060573A1 (en) * 2005-08-10 2007-03-15 Lars Wortmann Acyltryptophanols
EP1932831A1 (en) * 2006-12-13 2008-06-18 Bayer Schering Pharma Aktiengesellschaft 1,2-Diarylacetylene Derivatives of Acyltryptophanols
US20080221195A1 (en) * 2006-12-13 2008-09-11 Lars Wortmann 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
PE20091225A1 (es) * 2007-03-22 2009-09-16 Astrazeneca Ab Derivados de quinolina como antagonistas del receptor p2x7
TW200918058A (en) * 2007-08-31 2009-05-01 Organon Nv TSH receptor antagonizing tetrahydroquinoline compounds
PE20091036A1 (es) 2007-11-30 2009-08-15 Astrazeneca Ab Derivado de quinolina como antagonista del receptor p2x7
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
US8071587B2 (en) 2009-05-27 2011-12-06 N. V. Organon (Dihydro)imidazoiso[5,1-A]quinolines
TWI461426B (zh) * 2009-05-27 2014-11-21 Merck Sharp & Dohme (二氫)咪唑並異〔5,1-a〕喹啉類
TW201116531A (en) 2009-07-29 2011-05-16 Organon Nv Ring-annulated dihydropyrrolo[2,1-a]isoquinolines
US8431564B2 (en) 2009-07-29 2013-04-30 Merck Sharp & Dohme B.V. Ring-annulated dihydropyrrolo[2,1-α]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
EP3174932B1 (en) 2014-07-30 2021-06-09 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
CN118791413B (zh) * 2024-06-18 2025-04-18 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
DE3879031T2 (de) 1987-08-08 1993-06-24 Akzo Nv Kontrazeptives implantat.
ATE269336T1 (de) * 1994-12-22 2004-07-15 Ligand Pharm Inc Steroidrezeptor-modulator verbindungen und methoden
CA2339018A1 (en) * 1998-08-07 2000-02-17 Applied Research Systems Ars Holding N.V. Fsh mimetics for the treatment of infertility
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
PT1406628E (pt) 2001-07-02 2006-06-30 Akzo Nobel Nv Derivados de tera-hidroquinolina
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
ZA200309921B (en) 2005-03-22
ECSP034932A (es) 2004-02-26
RU2347570C2 (ru) 2009-02-27
KR20040030714A (ko) 2004-04-09
MXPA03011908A (es) 2004-06-03
PE20030273A1 (es) 2003-03-21
ES2260458T3 (es) 2006-11-01
CZ20042A3 (en) 2004-04-14
NZ530198A (en) 2005-11-25
KR100908468B1 (ko) 2009-07-21
US8058441B2 (en) 2011-11-15
SK16342003A3 (sk) 2004-07-07
WO2003004028A1 (en) 2003-01-16
SA02230260B1 (ar) 2007-03-25
US20040236109A1 (en) 2004-11-25
DE60209734D1 (de) 2006-05-04
US8258293B2 (en) 2012-09-04
HK1061810A1 (en) 2004-10-08
EP1406628A1 (en) 2004-04-14
PT1406628E (pt) 2006-06-30
IS2418B (is) 2008-10-15
ATE319451T1 (de) 2006-03-15
CN1529601A (zh) 2004-09-15
PL367638A1 (en) 2005-03-07
DK1406628T3 (da) 2006-07-03
AR034669A1 (es) 2004-03-03
BR0210645A (pt) 2004-10-05
IL159288A0 (en) 2004-06-01
AU2002317848B2 (en) 2006-08-31
HRP20031080A2 (en) 2004-04-30
HUP0400390A2 (hu) 2004-09-28
SK286759B6 (sk) 2009-05-07
EP1406628B1 (en) 2006-03-08
CY1106087T1 (el) 2011-06-08
US20120202996A1 (en) 2012-08-09
RU2004102693A (ru) 2005-06-27
NO20035763L (no) 2003-12-29
JP4523273B2 (ja) 2010-08-11
NO325516B1 (no) 2008-06-02
CA2452606C (en) 2011-09-13
CN1261099C (zh) 2006-06-28
CA2452606A1 (en) 2003-01-16
JP2004535456A (ja) 2004-11-25
IS7071A (is) 2003-12-11

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