CN100376246C - 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物 - Google Patents

作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物 Download PDF

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Publication number
CN100376246C
CN100376246C CNB2004800196064A CN200480019606A CN100376246C CN 100376246 C CN100376246 C CN 100376246C CN B2004800196064 A CNB2004800196064 A CN B2004800196064A CN 200480019606 A CN200480019606 A CN 200480019606A CN 100376246 C CN100376246 C CN 100376246C
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China
Prior art keywords
methyl
fluoro
chemical compound
pyrimidine
diketone
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Expired - Fee Related
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Chinese (zh)
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CN1826119A (zh
Inventor
朱云飞
科林·里根
贾米·K·吕特尔
郭志强
陈永胜
查尔斯·Q·黄
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Neurocrine Biosciences Inc
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Neurocrine Biosciences Inc
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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D239/00Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/52Two oxygen atoms
    • C07D239/54Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
    • 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
    • A61K31/495Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
    • A61K31/505Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
    • A61K31/513Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim having oxo groups directly attached to the heterocyclic ring, e.g. cytosine
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04Drugs 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
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00Drugs for disorders of the urinary system
    • A61P13/08Drugs for disorders of the urinary system of the prostate
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00Drugs for genital or sexual disorders; 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
    • A61P15/08Drugs 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
    • A61P17/00Drugs for dermatological disorders
    • A61P17/02Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00Drugs for disorders of the nervous system
    • A61P25/20Hypnotics; Sedatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00Antineoplastic agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00Drugs for immunological or allergic disorders
    • A61P37/02Immunomodulators
    • 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
    • A61P5/02Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P5/00Drugs for disorders of the endocrine system
    • A61P5/02Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin
    • A61P5/04Drugs for disorders of the endocrine system of the hypothalamic hormones, e.g. TRH, GnRH, CRH, GRH, somatostatin for decreasing, blocking or antagonising the activity of the hypothalamic 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
    • A61P5/24Drugs for disorders of the endocrine system of the sex hormones
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D401/00Heterocyclic 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
    • C07D401/02Heterocyclic 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
    • C07D401/06Heterocyclic 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 carbon chain containing only aliphatic carbon atoms

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Diabetes (AREA)
  • Immunology (AREA)
  • Gynecology & Obstetrics (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Anesthesiology (AREA)
  • Dermatology (AREA)
  • Pregnancy & Childbirth (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
CNB2004800196064A 2003-07-07 2004-07-06 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物 Expired - Fee Related CN100376246C (zh)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US48543603P 2003-07-07 2003-07-07
US60/485,436 2003-07-07

Related Child Applications (1)

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CNA2008100027460A Division CN101229165A (zh) 2003-07-07 2004-07-06 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物

Publications (2)

Publication Number Publication Date
CN1826119A CN1826119A (zh) 2006-08-30
CN100376246C true CN100376246C (zh) 2008-03-26

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CNB2004800196064A Expired - Fee Related CN100376246C (zh) 2003-07-07 2004-07-06 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物
CNA2008100027460A Pending CN101229165A (zh) 2003-07-07 2004-07-06 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物

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Country Status (14)

Country Link
US (2) US7071200B2 (https=)
EP (1) EP1660091B1 (https=)
JP (2) JP4658044B2 (https=)
KR (1) KR20060052790A (https=)
CN (2) CN100376246C (https=)
AT (1) ATE428427T1 (https=)
AU (1) AU2004257636B2 (https=)
BR (1) BRPI0412327A (https=)
CA (1) CA2531507C (https=)
DE (1) DE602004020638D1 (https=)
EA (1) EA200600188A1 (https=)
IL (1) IL172834A0 (https=)
MX (1) MXPA06000300A (https=)
WO (1) WO2005007164A1 (https=)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107935863A (zh) * 2017-11-30 2018-04-20 厦门海乐景生化有限公司 Elagolix的关键原料化合物C的合成方法

Families Citing this family (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
PT1255738E (pt) * 2000-01-25 2012-06-19 Neurocrine Biosciences Inc Antagonistas do receptor da hormona de libertação da gonadotrofina e métodos relacionados com os mesmos
US7015226B2 (en) * 2003-07-07 2006-03-21 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
CN100424078C (zh) * 2003-07-07 2008-10-08 纽罗克里生物科学有限公司 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物
CN102127057A (zh) * 2004-03-15 2011-07-20 武田药品工业株式会社 二肽基肽酶抑制剂
KR20080006564A (ko) 2005-03-24 2008-01-16 얀센 파마슈티카 엔.브이. 프로키네티신 1 수용체 길항제
AU2006227394A1 (en) 2005-03-24 2006-09-28 Janssen Pharmaceutica N.V. Prokineticin 1 receptor
KR100837785B1 (ko) * 2007-01-17 2008-06-13 한국화학연구원 1,2,4-티아다이아졸리딘-3,5-다이온 화합물을 포함하는염증관련 질환의 치료 및 예방을 위한 약제학적 조성물
PE20090044A1 (es) 2007-04-06 2009-01-23 Neurocrine Biosciences Inc Antagonistas del receptor de la hormona liberadora de gonadotropina y procedimientos relacionados con los mismos
CL2008000986A1 (es) 2007-04-06 2008-10-17 Neurocrine Biosciences Inc COMPUESTO DERIVADO DE HETEROCICLOS DE NITROGENO, AGONISTAS DEL RECEPTOR GnRH; COMPOSICION FARMACEUTICA QUE COMPRENDE A DICHO COMPUESTO; Y USO PARA TRATAR UNA AFECCION RELACIONADA CON LAS HORMONAS SEXUALES, ENDOMETRIOSIS, DISMENORREA, ENFERMEDAD DE OV
US8765948B2 (en) 2007-11-07 2014-07-01 Neurocrine Biosciences, Inc. Processes for the preparation of uracil derivatives
US9034850B2 (en) 2009-11-20 2015-05-19 Sk Chemicals Co., Ltd. Gonadotropin releasing hormone receptor antagonist, preparation method thereof and pharmaceutical composition comprising the same
TW201130854A (en) 2009-12-22 2011-09-16 Bayer Schering Pharma Ag Pyridinone derivatives and pharmaceutical compositions thereof
WO2012175514A1 (en) 2011-06-21 2012-12-27 Bayer Intellectual Property Gmbh Pyridinone derivatives and pharmaceutical compositions thereof
WO2019115019A1 (en) * 2017-12-11 2019-06-20 Synthon B.V. Process for preparing elagolix
EP3826638A4 (en) 2018-07-23 2022-04-06 Abbvie Inc. ELAGOLIX SODIUM COMPOSITIONS AND RELATED METHODS
WO2020240375A1 (en) * 2019-05-24 2020-12-03 Dr. Reddy’S Laboratories Limited Improved process for the preparation of elagolix and its intermediates
ES2802815B2 (es) 2019-07-12 2022-03-14 Moehs Iberica Sl Sal clorhidrato de 3-[2(r)-amino-2-feniletil]-5-(2-fluoro-3-metoxifenil)-1-[2-fluoro-6-(trifluorometil)bencil]-6-metil-1h-pirimidin-2,4(1h,3h)-diona (i) en forma solida, procedimiento para su preparacion y uso de la misma en la sintesis de elagolix
CN112300081A (zh) * 2019-07-31 2021-02-02 上海度德医药科技有限公司 噁拉戈利的中间体及其制备方法和应用
CN112694445B (zh) * 2019-10-22 2023-07-28 成都倍特药业股份有限公司 一种噁拉戈利钠中间体的纯化方法
ES2822398B2 (es) 2019-10-30 2022-03-02 Moehs Iberica Sl 3-((R)-2-(Amino-2-feniletil)-1-(2-fluoro-6-trifluorometilbencil)-5-yodo-6-metil-1H-pirimidin-2,4-diona o una sal de la misma, procedimiento para su preparación y su uso en la síntesis de elagolix
CN110938038A (zh) * 2019-11-14 2020-03-31 上海星酶生物科技有限公司 一种c13h10f4n2o2的制备工艺
CN111333586A (zh) * 2020-02-19 2020-06-26 诚达药业股份有限公司 一种含有6-甲基尿嘧啶结构化合物的制备方法
CN111333587B (zh) * 2020-04-11 2023-04-07 东莞市东阳光新药研发有限公司 取代的嘧啶-2,4(1h,3h)-二酮衍生物及其用途
CN113527213B (zh) * 2020-04-20 2023-01-03 上海英诺富成生物科技有限公司 促性激素释放激素受体拮抗剂及其用途
CN111574461A (zh) * 2020-05-29 2020-08-25 奥锐特药业股份有限公司 一种噁拉戈利中间体的成盐纯化方法及获得的噁拉戈利中间体精品

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5859014A (en) * 1995-06-09 1999-01-12 Syntex (U.S.A.) Inc. Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU5844896A (en) 1995-06-01 1996-12-18 Takeda Chemical Industries Ltd. Tricyclic diazepines useful as gnrh receptor antagonists
CA2229201A1 (en) 1995-10-19 1997-04-24 Satoshi Sasaki Quinoline derivatives, their production and use
EP0862573A1 (en) 1995-10-19 1998-09-09 Takeda Chemical Industries, Ltd. Thienopyridine derivatives as gonadotropin releasing hormone antagonists
PL327146A1 (en) 1995-12-14 1998-11-23 Merck & Co Inc Antagonists of the gonadotrophin liberating hormone
CA2240048A1 (en) 1995-12-14 1997-06-19 Mark Goulet Antagonists of gonadotropin releasing hormone
CA2240115A1 (en) 1995-12-14 1997-06-19 Wallace T. Ashton Antagonists of gonadotropin releasing hormone
SK77498A3 (en) 1995-12-14 1999-01-11 Merck & Co Inc Nonpeptide derivatives, pharmaceutical composition containing them and their use
CA2292881A1 (en) 1997-06-05 1998-12-10 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
AU7806998A (en) 1997-06-05 1998-12-21 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
WO1998055470A1 (en) 1997-06-05 1998-12-10 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
AU729663B2 (en) 1997-06-05 2001-02-08 Merck & Co., Inc. Antagonists of gonadotropin releasing hormone
US6313301B1 (en) 1997-08-13 2001-11-06 Takeda Chemical Industries, Ltd. Thienopyridine derivatives, their intermediates and production thereof
CA2372044A1 (en) 1999-05-14 2000-11-23 Neurocrine Biosciences, Inc. Imidazo- and pyrrolo[1,2-a]pyrimid-4-ones as gonadotropin-releasing hormone receptor antagonists
US20020065309A1 (en) 1999-08-04 2002-05-30 Ge Peng Novel Bicyclic and tricyclic pyrrolidine derivatives as GnRH antagonists
DE60022769T2 (de) 1999-10-15 2006-07-06 Neurocrine Biosciences, Inc., San Diego Gonadotropin freisetzenden hormon rezeptor antagonisten und ihre verwandten verwendungen
PT1255738E (pt) * 2000-01-25 2012-06-19 Neurocrine Biosciences Inc Antagonistas do receptor da hormona de libertação da gonadotrofina e métodos relacionados com os mesmos
SE0100566D0 (sv) 2001-02-20 2001-02-20 Astrazeneca Ab Compounds
JP2005500352A (ja) 2001-08-02 2005-01-06 ニューロクライン バイオサイエンシーズ, インコーポレイテッド ゴナドトロピン放出ホルモンレセプター(GnRH)アンタゴニストとしての1,2,4−トリアジン−3,5−ジオン
AU2002324586B2 (en) 2001-08-02 2008-04-24 Neurocrine Biosciences, Inc. 1,3,5-triazine-2,4,6-triones, preparation and use as gonadotropin-releasing hormone receptor antagonists
JP2005500356A (ja) 2001-08-02 2005-01-06 ニューロクライン バイオサイエンシーズ, インコーポレイテッド ゴナドトロピン放出ホルモンレセプターアンタゴニスト
WO2003011293A2 (en) 2001-08-02 2003-02-13 Neurocrine Biosciences, Inc. Pyridinone and pyridazinone derivatives as gonadotropin-releasing hormone receptor antagonists
JP2005505525A (ja) 2001-08-02 2005-02-24 ニューロクライン バイオサイエンシーズ, インコーポレイテッド 性腺刺激ホルモン放出ホルモンレセプターアンタゴニストおよびそれに関連する方法
US7015226B2 (en) 2003-07-07 2006-03-21 Neurocrine Biosciences, Inc. Gonadotropin-releasing hormone receptor antagonists and methods relating thereto
CN100424078C (zh) 2003-07-07 2008-10-08 纽罗克里生物科学有限公司 作为促性激素释放激素受体拮抗剂的嘧啶-2,4-二酮衍生物

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5859014A (en) * 1995-06-09 1999-01-12 Syntex (U.S.A.) Inc. Pyrimidinedione, pyrimidinetrione, triazinedione and tetrahydroquinazolinedione derivatives as α1 -adrenergic receptor antagonists

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107935863A (zh) * 2017-11-30 2018-04-20 厦门海乐景生化有限公司 Elagolix的关键原料化合物C的合成方法

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EP1660091A1 (en) 2006-05-31
IL172834A0 (en) 2006-06-11
US7071200B2 (en) 2006-07-04
DE602004020638D1 (de) 2009-05-28
AU2004257636A1 (en) 2005-01-27
AU2004257636B2 (en) 2011-01-06
EP1660091B1 (en) 2009-04-15
KR20060052790A (ko) 2006-05-19
CN101229165A (zh) 2008-07-30
JP4658044B2 (ja) 2011-03-23
BRPI0412327A (pt) 2006-09-05
ATE428427T1 (de) 2009-05-15
EA200600188A1 (ru) 2006-08-25
MXPA06000300A (es) 2006-03-28
CN1826119A (zh) 2006-08-30
US7329669B2 (en) 2008-02-12
JP2011088903A (ja) 2011-05-06
US20050043338A1 (en) 2005-02-24
JP2007521308A (ja) 2007-08-02
CA2531507C (en) 2013-10-01
WO2005007164A1 (en) 2005-01-27
US20070015778A1 (en) 2007-01-18
CA2531507A1 (en) 2005-01-27

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