JP4717811B2 - 新規化合物 - Google Patents
新規化合物 Download PDFInfo
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- JP4717811B2 JP4717811B2 JP2006519250A JP2006519250A JP4717811B2 JP 4717811 B2 JP4717811 B2 JP 4717811B2 JP 2006519250 A JP2006519250 A JP 2006519250A JP 2006519250 A JP2006519250 A JP 2006519250A JP 4717811 B2 JP4717811 B2 JP 4717811B2
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- lower alkyl
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- alkoxy
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- URFPRAHGGBYNPW-UHFFFAOYSA-N CCc(cc1)ccc1Br Chemical compound CCc(cc1)ccc1Br URFPRAHGGBYNPW-UHFFFAOYSA-N 0.000 description 1
- NHLLTFBTSYXSJX-UHFFFAOYSA-N CCc1ccc(C(c2ccccc2[N+]([O-])=O)O)cc1 Chemical compound CCc1ccc(C(c2ccccc2[N+]([O-])=O)O)cc1 NHLLTFBTSYXSJX-UHFFFAOYSA-N 0.000 description 1
- GQQDZIWAWXQAIS-UHFFFAOYSA-N CCc1ccc(CC2=CC=CCC2N)cc1 Chemical compound CCc1ccc(CC2=CC=CCC2N)cc1 GQQDZIWAWXQAIS-UHFFFAOYSA-N 0.000 description 1
- CMWKITSNTDAEDT-UHFFFAOYSA-N [O-][N+](c1ccccc1C=O)=O Chemical compound [O-][N+](c1ccccc1C=O)=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
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- 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
-
- 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
- A61P9/12—Antihypertensives
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
- C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Diabetes (AREA)
- Molecular Biology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Neurosurgery (AREA)
- Child & Adolescent Psychology (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Ophthalmology & Optometry (AREA)
- Emergency Medicine (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Saccharide Compounds (AREA)
Description
Rは水素原子、低級アルキル基、低級アルカノイル基または低級アルコキシカルボニル基である)。
対応する原料化合物から、実施例1と同様の方法で表1に記載の化合物を製造した。
(1)4−フルオロアニリン(1.00g)、ヨウ素(2.28g)および硫酸銀(2.81g)のエタノール(180ml)混合溶液を室温において1時間撹拌した。不溶物をろ去し、そしてろ液の溶媒を減圧下に留去した。残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=19:1)で精製して4−フルオロ−2−ヨードアニリン(1.16g)を無色の油状物として得た。ESI−Mass m/Z 236(M−H)。
3,4−ジフルオロ−2−ヨードアニリン(S. Morita et a1., Tetrahedron Asymmetry(1995)6 245参照)を参考例2と同様の方法で処理して目的の3,4−ジフルオロ−2−(4−エチルベンジル)アニリンを粉末として得た。APCI−Mass m/Z 247(M+H)。
Claims (4)
- 式IA
R4およびR5は、それぞれ独立して水素原子;ハロゲン原子;ヒドロキシル基;アルコキシ基;アルキル基;ハロアルキル基;ハロアルコキシ基;ヒドロキシアルキル基;アルコキシアルキル基;フェニルアルキル基;アルコキシアルコキシ基;ヒドロキシアルコキシ基;アルケニル基;アルキニル基;シクロアルキル基;シクロアルキリデンメチル基;フェニルオキシ基;フェニルアルコキシ基;シアノ基;ニトロ基;アミノ基;モノ−もしくはジ−アルキルアミノ基;アルカノイルアミノ基;カルボキシル基;アルコキシカルボニル基;カルバモイル基;モノ−もしくはジ−アルキルカルバモイル基;アルカノイル基;アルキルスルホニルアミノ基;フェニルスルホニルアミノ基;アルキルスルフィニル基;アルキルスルホニル基;フェニルスルホニル基;ハロゲン原子、シアノ基、アルキル基、ハロアルキル基、アルコキシ基、ハロアルコキシ基、アルキレンジオキシ基、アルキレンオキシ基、またはモノ−もしくはジ−アルキルアミノ基で置換されていてもよいフェニル基;またはハロゲン原子、シアノ基、アルキル基、ハロアルキル基、アルコキシ基もしくはハロアルコキシ基で置換されていてもよいヘテロシクリル基であるか、あるいはR4およびR5は、互いにそれらの末端で結合してアルキレン基を形成し;
Rは水素原子、低級アルキルキ基、低級アルカノイル基または低級アルコキシカルボニル基である。)
で示される化合物、またはその医薬的に許容しうる塩。 - R1、R2、およびR3が、それぞれ独立して、水素原子、ハロゲン原子、低級アルキル基、ヒドロキシ低級アルキル基、ハロ低級アルキル基、低級アルコキシ低級アルキル基、低級アルコキシ基、ハロ低級アルコキシ基、または低級アルコキシ低級アルコキシ基であり、
R4およびR5が、それぞれ独立して、水素原子;ハロゲン原子;低級アルキル基;ハロ低級アルキル基;フェニル低級アルキル基;ハロゲン原子、シアノ基、低級アルキル基、ハロ低級アルキル基、低級アルコキシ基、メチレンジオキシ基、エチレンオキシ基、またはモノ−もしくはジ−低級アルキルアミノ基で置換されていてもよいフェニル基;または、ハロゲン原子もしくは低級アルキル基で置換されていてもよいヘテロシクリル基であるか、またはR4およびR5が互いにそれらの末端で結合してアルキレン基を形成する、
請求項1記載の化合物、またはその医薬的に許容しうる塩。 - R1がハロゲン原子、低級アルキル基または低級アルコキシ基であり、R2およびR3が水素原子であり、R4が、ハロゲン原子;低級アルキル基;低級アルコキシ基;ハロゲン原子、シアノ基、低級アルキル基、ハロ低級アルキル基、低級アルコキシ基、およびモノ−もしくはジ−低級アルキルアミノ基からなる群より選ばれる置換基で置換されていてもよいフェニル基;または、ハロゲン原子もしくは低級アルキル基で置換されていてもよいヘテロシクリル基であり、R5が水素原子である、請求項1記載の化合物、またはその医薬的に許容しうる塩。
- ヘテロシクリル基がチエニル基、ピリジル基、ピリミジル基、ピラジニル基、ピラゾリル基、チアゾリル基、キノリル基またはテトラゾリル基である、請求項1、2または3記載の化合物、またはその医薬的に許容しうる塩。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US49152303P | 2003-08-01 | 2003-08-01 | |
US60/491,523 | 2003-08-01 | ||
PCT/JP2004/011311 WO2005012321A1 (en) | 2003-08-01 | 2004-07-30 | Novel compounds |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2007518682A JP2007518682A (ja) | 2007-07-12 |
JP2007518682A5 JP2007518682A5 (ja) | 2007-09-20 |
JP4717811B2 true JP4717811B2 (ja) | 2011-07-06 |
Family
ID=34115512
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2006519250A Expired - Fee Related JP4717811B2 (ja) | 2003-08-01 | 2004-07-30 | 新規化合物 |
Country Status (18)
Country | Link |
---|---|
US (1) | US7521430B2 (ja) |
EP (1) | EP1654269B1 (ja) |
JP (1) | JP4717811B2 (ja) |
KR (1) | KR101101500B1 (ja) |
CN (2) | CN102060888A (ja) |
AU (1) | AU2004260760B2 (ja) |
BR (1) | BRPI0413233A (ja) |
CA (1) | CA2534022C (ja) |
EA (1) | EA011025B1 (ja) |
ES (1) | ES2527053T3 (ja) |
IL (1) | IL173051A (ja) |
MX (1) | MXPA06001273A (ja) |
NO (1) | NO333679B1 (ja) |
NZ (1) | NZ545305A (ja) |
TW (1) | TWI377209B (ja) |
UA (5) | UA86042C2 (ja) |
WO (1) | WO2005012321A1 (ja) |
ZA (2) | ZA200601686B (ja) |
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US8785403B2 (en) | 2003-08-01 | 2014-07-22 | Mitsubishi Tanabe Pharma Corporation | Glucopyranoside compound |
SI1651658T2 (sl) | 2003-08-01 | 2020-12-31 | Mitsubishi Tanabe Pharma Corporation | Nove spojine, ki imajo inhibitorno aktivnost proti transporterju, ki je odvisen od natrija |
TW200637869A (en) | 2005-01-28 | 2006-11-01 | Chugai Pharmaceutical Co Ltd | The spiroketal derivatives and the use as therapeutical agent for diabetes of the same |
AR053329A1 (es) * | 2005-01-31 | 2007-05-02 | Tanabe Seiyaku Co | Derivados de indol utiles como inhibidores de los transportadores de glucosa dependientes del sodio (sglt) |
MY147375A (en) | 2005-01-31 | 2012-11-30 | Mitsubishi Tanabe Pharma Corp | Indole derivatives |
JP5073948B2 (ja) * | 2005-01-31 | 2012-11-14 | 田辺三菱製薬株式会社 | 医薬組成物 |
TWI418556B (zh) * | 2006-07-27 | 2013-12-11 | Mitsubishi Tanabe Pharma Corp | 吲哚衍生物 |
TWI499414B (zh) * | 2006-09-29 | 2015-09-11 | Lexicon Pharmaceuticals Inc | 鈉與葡萄糖第2型共同運輸體(co-transporter 2)的抑制物與其應用方法 |
WO2008070609A1 (en) * | 2006-12-04 | 2008-06-12 | Janssen Pharmaceutica N.V. | Thienyl-containing glycopyranosyl derivatives as antidiabetics |
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WO2008109591A1 (en) * | 2007-03-08 | 2008-09-12 | Lexicon Pharmaceuticals, Inc. | Phlorizin analogs as inhibitors of sodium glucose co-transporter 2 |
UA105480C2 (uk) | 2007-09-10 | 2014-05-26 | Янссен Фармацевтика Н.В. | Спосіб одержання сполук, які застосовують як інгібітори натрійзалежного переносника глюкози |
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MX2010012656A (es) | 2008-05-22 | 2010-12-20 | Squibb Bristol Myers Co | Metodo para tratar la hiperuricemia empleando un inhibidor de sglt2 y composicion que contiene el mismo. |
PE20110288A1 (es) | 2008-08-28 | 2011-05-26 | Pfizer | Derivados de dioxa-biciclo[3.2.1]octano-2,3,4-triol |
EA201100502A1 (ru) * | 2008-09-19 | 2011-10-31 | Новартис Аг | Гликозидные производные и их применения |
US9056850B2 (en) * | 2008-10-17 | 2015-06-16 | Janssen Pharmaceutica N.V. | Process for the preparation of compounds useful as inhibitors of SGLT |
US20110009347A1 (en) | 2009-07-08 | 2011-01-13 | Yin Liang | Combination therapy for the treatment of diabetes |
ES2416459T3 (es) | 2009-07-10 | 2013-08-01 | Janssen Pharmaceutica, N.V. | Procedimiento de cristalización para 1-( -D-glucopiranosil)-4-metil-3-[5-(4-fluorofenil)-2-tienilmetil]benceno |
DK2488515T3 (en) * | 2009-10-14 | 2017-02-27 | Janssen Pharmaceutica Nv | PROCEDURE FOR THE PREPARATION OF COMPOUNDS USED AS INHIBITORS OF SGLT2 |
NZ599945A (en) | 2009-11-02 | 2014-05-30 | Pfizer | Dioxa-bicyclo[3.2.1]octane-2,3,4-triol derivatives |
ES2596291T3 (es) | 2010-05-11 | 2017-01-05 | Janssen Pharmaceutica, N.V. | Formulaciones farmacéuticas que comprenden derivados de 1-(beta-d-glucopiranosil)-2-tienilmetilbenceno como inhibidores de sglt |
PT2697218T (pt) | 2011-04-13 | 2016-07-13 | Janssen Pharmaceutica Nv | Processo para preparação de compostos úteis como inibidores da sglt2 |
US9035044B2 (en) * | 2011-05-09 | 2015-05-19 | Janssen Pharmaceutica Nv | L-proline and citric acid co-crystals of (2S, 3R, 4R, 5S,6R)-2-(3-((5-(4-fluorophenyl)thiopen-2-yl)methyl)4-methylphenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol |
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WO2003020737A1 (en) | 2001-09-05 | 2003-03-13 | Bristol-Myers Squibb Company | O-pyrazole glucoside sglt2 inhibitors and method of use |
DE102004048388A1 (de) * | 2004-10-01 | 2006-04-06 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | D-Pyranosyl-substituierte Phenyle, diese Verbindungen enthaltende Arzneimittel, deren Verwendung und Verfahren zu ihrer Herstellung |
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WO2001068660A1 (fr) * | 2000-03-17 | 2001-09-20 | Kissei Pharmaceutical Co., Ltd. | Derives glucopyranosyloxybenzylbenzene, preparations medicinales les contenant et intermediaires pour la preparation desdits derives |
WO2001074834A1 (en) * | 2000-03-30 | 2001-10-11 | Bristol-Myers Squibb Company | O-aryl glucoside sglt2 inhibitors and method |
WO2002028872A1 (fr) * | 2000-09-29 | 2002-04-11 | Kissei Pharmaceutical Co., Ltd. | Derives de glucopyranosiloxybenzylbenzene et compositions therapeutiques contenant ces composes |
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WO2002064606A1 (fr) * | 2001-02-14 | 2002-08-22 | Kissei Pharmaceutical Co., Ltd. | Derives glucopyranosyloxybenzylbenzene et leur utilisation medicale |
Also Published As
Publication number | Publication date |
---|---|
UA85569C2 (ru) | 2009-02-10 |
AU2004260760A1 (en) | 2005-02-10 |
AU2004260760B2 (en) | 2009-08-13 |
UA86042C2 (en) | 2009-03-25 |
UA83377C2 (uk) | 2008-07-10 |
NO20060219L (no) | 2006-04-28 |
IL173051A0 (en) | 2006-06-11 |
TWI377209B (en) | 2012-11-21 |
WO2005012321A1 (en) | 2005-02-10 |
MXPA06001273A (es) | 2006-04-11 |
EA200600348A1 (ru) | 2006-08-25 |
ZA200601686B (en) | 2007-05-30 |
CA2534022A1 (en) | 2005-02-10 |
BRPI0413233A (pt) | 2006-10-03 |
NO333679B1 (no) | 2013-08-05 |
NZ545305A (en) | 2008-11-28 |
EP1654269A1 (en) | 2006-05-10 |
US7521430B2 (en) | 2009-04-21 |
EP1654269B1 (en) | 2014-10-15 |
JP2007518682A (ja) | 2007-07-12 |
CN1829728A (zh) | 2006-09-06 |
IL173051A (en) | 2012-06-28 |
UA86599C2 (en) | 2009-05-12 |
ZA200603880B (en) | 2010-01-27 |
US20070060545A1 (en) | 2007-03-15 |
KR20060132539A (ko) | 2006-12-21 |
EA011025B1 (ru) | 2008-12-30 |
KR101101500B1 (ko) | 2012-01-03 |
CN102060888A (zh) | 2011-05-18 |
CA2534022C (en) | 2012-10-02 |
UA87991C2 (en) | 2009-09-10 |
TW200510440A (en) | 2005-03-16 |
ES2527053T3 (es) | 2015-01-20 |
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