CA2501833A1 - 5-(1',1'-cycloalkyl/alkenyl)methylidene 1,2-dihydro-5h-chromeno[3,4-f]quinolines as selective progesterone receptor modulator compounds - Google Patents
5-(1',1'-cycloalkyl/alkenyl)methylidene 1,2-dihydro-5h-chromeno[3,4-f]quinolines as selective progesterone receptor modulator compounds Download PDFInfo
- Publication number
- CA2501833A1 CA2501833A1 CA002501833A CA2501833A CA2501833A1 CA 2501833 A1 CA2501833 A1 CA 2501833A1 CA 002501833 A CA002501833 A CA 002501833A CA 2501833 A CA2501833 A CA 2501833A CA 2501833 A1 CA2501833 A1 CA 2501833A1
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- Prior art keywords
- group
- hydrogen
- alkyl
- haloalkyl
- independently
- 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.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 92
- 239000002379 progesterone receptor modulator Substances 0.000 title description 7
- -1 methylidene 1,2-dihydro-5h-chromeno[3,4-f]quinolines Chemical class 0.000 title description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 61
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 61
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 50
- 102000003998 progesterone receptors Human genes 0.000 claims abstract description 44
- 108090000468 progesterone receptors Proteins 0.000 claims abstract description 44
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 43
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 40
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 37
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 35
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 33
- 238000000034 method Methods 0.000 claims abstract description 29
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 18
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 10
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 230000001404 mediated effect Effects 0.000 claims abstract description 8
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 6
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims abstract description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
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- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 6
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- AOSZTAHDEDLTLQ-AZKQZHLXSA-N (1S,2S,4R,8S,9S,11S,12R,13S,19S)-6-[(3-chlorophenyl)methyl]-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one Chemical compound C([C@@H]1C[C@H]2[C@H]3[C@]([C@]4(C=CC(=O)C=C4[C@@H](F)C3)C)(F)[C@@H](O)C[C@@]2([C@@]1(C1)C(=O)CO)C)N1CC1=CC=CC(Cl)=C1 AOSZTAHDEDLTLQ-AZKQZHLXSA-N 0.000 claims description 3
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- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 claims description 3
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- RITVYBKZHUTSEL-UHFFFAOYSA-N 5-(1,3-dithian-2-ylidene)-7-fluoro-2,2-dimethyl-1h-chromeno[3,4-f]quinoline Chemical compound C12=C3C=CC(C)(C)NC3=CC=C2C2=CC=CC(F)=C2OC1=C1SCCCS1 RITVYBKZHUTSEL-UHFFFAOYSA-N 0.000 claims 1
- UBNPHBBSESDOSW-UHFFFAOYSA-N 5-(1,3-dithian-2-ylidene)-8-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinoline Chemical compound C=1C(OC)=CC=C(C2=C3C=4C(C)=CC(C)(C)NC=4C=C2)C=1OC3=C1SCCCS1 UBNPHBBSESDOSW-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
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- 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
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- 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
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- 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
- A61P5/30—Oestrogens
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- 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
- A61P5/34—Gestagens
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/74—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving hormones or other non-cytokine intercellular protein regulatory factors such as growth factors, including receptors to hormones and growth factors
- G01N33/743—Steroid hormones
Landscapes
- Health & Medical Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Urology & Nephrology (AREA)
- Immunology (AREA)
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- Hematology (AREA)
- Biomedical Technology (AREA)
- Reproductive Health (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Microbiology (AREA)
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- Food Science & Technology (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- Pregnancy & Childbirth (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41814002P | 2002-10-11 | 2002-10-11 | |
| US60/418,140 | 2002-10-11 | ||
| PCT/US2003/024416 WO2004033459A1 (en) | 2002-10-11 | 2003-08-04 | 5-(1',1'-CYCLOALKYL/ALKENYL)METHYLIDENE 1,2-DIHYDRO-5H-CHROMENO[3,4-f]QUINOLINES AS SELECTIVE PROGESTERONE RECEPTOR MODULATOR COMPOUNDS |
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| JP (1) | JP2006504736A (enExample) |
| AR (1) | AR040783A1 (enExample) |
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| CA (1) | CA2501833A1 (enExample) |
| MX (1) | MXPA05003800A (enExample) |
| WO (1) | WO2004033459A1 (enExample) |
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| US6566372B1 (en) | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| US7026484B2 (en) * | 2001-02-23 | 2006-04-11 | Ligand Pharmaceuticals Incorporated | Tricyclic androgen receptor modulator compounds and methods |
| DE20301728U1 (de) | 2002-10-11 | 2004-03-11 | Ligand Pharmaceuticals, Inc., San Diego | 5-substituierte 7,9-Difluor-5H-Chromeno(3,4-f) -Chinolin-Verbindungen als selektive Progesteronrezeptormodulator-Verbindungen |
| AU2003258050A1 (en) * | 2002-10-11 | 2004-05-04 | Ligand Pharmaceuticals Incorporated | 5-cycloalkenyl 5h-chromeno(3,4-f)quinoline derivatives as selective progesterone receptor modulator compounds |
| EP1558618A1 (en) * | 2002-10-11 | 2005-08-03 | Ligand Pharmaceuticals, Inc. | 5-(1 ,1 -CYCLOALKYL/ALKENYL)METHYLIDENE 1,2-DIHYDRO- 5H /-CHROMENO[3,4-f ] QUINOLINES AS SELECTIVE PROGESTERONE RECEPTOR MODULATOR COMPOUNDS |
| MXPA06001751A (es) * | 2003-08-22 | 2006-05-12 | Ligand Pharm Inc | Derivados de 6-cicloamino-2-quinolinona como compuestos moduladores de receptor de androgeno. |
| AP2949A (en) | 2006-03-07 | 2014-07-31 | Shroff Geeta | Compositions comprising human embryonic stem cellsand their derivatives, methods of use, and method s of preparation |
| EA201070715A1 (ru) * | 2007-12-20 | 2011-02-28 | Тева Вимен'С Хелс, Инк. | Режимы дозирования, фармацевтические композиции и упаковки для экстренной контрацепции |
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| US5808139A (en) | 1992-04-21 | 1998-09-15 | Ligand Pharmaceuticals Incorporated | Non-steroid progesterone receptor agonist and antagonist and compounds and methods |
| US5506102A (en) | 1993-10-28 | 1996-04-09 | Ligand Pharmaceuticals Incorporated | Methods of using the A form of the progesterone receptor to screen for antagonists of steroid intracellar receptor-mediated transcription |
| US5693646A (en) | 1994-12-22 | 1997-12-02 | Ligand Pharmaceuticals Incorporated | Steroid receptor modulator compounds and methods |
| US6696459B1 (en) | 1994-12-22 | 2004-02-24 | Ligand Pharmaceuticals Inc. | Steroid receptor modulator compounds and methods |
| ATE269336T1 (de) * | 1994-12-22 | 2004-07-15 | Ligand Pharm Inc | Steroidrezeptor-modulator verbindungen und methoden |
| JPH11209735A (ja) * | 1998-01-28 | 1999-08-03 | Dow Corning Toray Silicone Co Ltd | フイルム状シリコーンゴム接着剤及び接着方法 |
| DE69904804T2 (de) * | 1998-02-13 | 2003-11-06 | Abbott Laboratories, Abbott Park | Glucocorticoid selektive entzündungshemmende mittel |
| US6380207B2 (en) * | 1998-02-13 | 2002-04-30 | Abbott Laboratories | Glucocortiocoid-selective antiinflammatory agents |
| US6506766B1 (en) | 1998-02-13 | 2003-01-14 | Abbott Laboratories | Glucocortiocoid-selective antinflammatory agents |
| US6001846A (en) | 1998-02-17 | 1999-12-14 | Ligand Pharmaceuticals Incorporated | Process for the preparation of 1,2-dihydroquinolines |
| US6093825A (en) | 1998-05-27 | 2000-07-25 | American Home Products | Methods for preparation of 1,2-dihydroquinolines |
| US6093826A (en) | 1998-06-08 | 2000-07-25 | Ligand Pharmaceuticals Incorporated | Process for the preparation of C(5)-substituted 1,2-dihydro-5H-chromeno[3,4-f] quinolines |
| US6423699B1 (en) | 1999-05-04 | 2002-07-23 | American Home Products Corporation | Combination therapies using benzimidazolones |
| US6380178B1 (en) | 1999-05-04 | 2002-04-30 | American Home Products Corporation | Cyclic regimens using cyclocarbamate and cyclic amide derivatives |
| US6509334B1 (en) | 1999-05-04 | 2003-01-21 | American Home Products Corporation | Cyclocarbamate derivatives as progesterone receptor modulators |
| WO2000066592A1 (en) | 1999-05-04 | 2000-11-09 | American Home Products Corporation | Cyclic urea and cyclic amide derivatives |
| US6329416B1 (en) | 1999-05-04 | 2001-12-11 | American Home Products Corporation | Combination regimens using 3,3-substituted indoline derivatives |
| US6444668B1 (en) | 1999-05-04 | 2002-09-03 | Wyeth | Combination regimens using progesterone receptor modulators |
| US6399593B1 (en) | 1999-05-04 | 2002-06-04 | Wyeth | Cyclic regimens using cyclic urea and cyclic amide derivatives |
| US6391907B1 (en) | 1999-05-04 | 2002-05-21 | American Home Products Corporation | Indoline derivatives |
| US6358948B1 (en) | 1999-05-04 | 2002-03-19 | American Home Products Corporation | Quinazolinone and benzoxazine derivatives as progesterone receptor modulators |
| US6319912B1 (en) | 1999-05-04 | 2001-11-20 | American Home Products Corporation | Cyclic regimens using 2,1-benzisothiazoline 2,2-dioxides |
| EP1173213A1 (en) | 1999-05-04 | 2002-01-23 | American Home Products Corporation | Compositions containing benzimidazolones and progestogens |
| SI1173210T1 (en) | 1999-05-04 | 2005-02-28 | Wyeth | Contraceptive compositions containing antiprogestinic and progestinic |
| US6369056B1 (en) | 1999-05-04 | 2002-04-09 | American Home Products Corporation | Cyclic urea and cyclic amide derivatives |
| US6306851B1 (en) | 1999-05-04 | 2001-10-23 | American Home Products Corporation | Cyclocarbamate and cyclic amide derivatives |
| WO2000066560A1 (en) | 1999-05-04 | 2000-11-09 | American Home Products Corporation | Quinazolinone and benzoxazine derivatives as progesterone receptor modulators |
| US6498154B1 (en) | 1999-05-04 | 2002-12-24 | Wyeth | Cyclic regimens using quinazolinone and benzoxazine derivatives |
| US6407101B1 (en) | 1999-05-04 | 2002-06-18 | American Home Products Corporation | Cyanopyrroles |
| US6355648B1 (en) | 1999-05-04 | 2002-03-12 | American Home Products Corporation | Thio-oxindole derivatives |
| EP1175422A2 (en) | 1999-05-04 | 2002-01-30 | Ligand Pharmaceuticals Incorporated | Tetracyclic progesterone receptor modulator compounds and methods |
| US6358947B1 (en) | 1999-05-04 | 2002-03-19 | American Home Products Corporation | Tetracyclic progesterone receptor modulator compounds and methods |
| US6462032B1 (en) | 1999-05-04 | 2002-10-08 | Wyeth | Cyclic regimens utilizing indoline derivatives |
| US6339098B1 (en) | 1999-05-04 | 2002-01-15 | American Home Products Corporation | 2,1-benzisothiazoline 2,2-dioxides |
| US6380235B1 (en) | 1999-05-04 | 2002-04-30 | American Home Products Corporation | Benzimidazolones and analogues |
| US6417214B1 (en) | 1999-05-04 | 2002-07-09 | Wyeth | 3,3-substituted indoline derivatives |
| US6566372B1 (en) | 1999-08-27 | 2003-05-20 | Ligand Pharmaceuticals Incorporated | Bicyclic androgen and progesterone receptor modulator compounds and methods |
| US6172241B1 (en) | 1999-10-15 | 2001-01-09 | Ligand Pharmaceuticals Incorporated | Process for the preparation of 1,2-dihydroquinolines |
| UA73119C2 (en) | 2000-04-19 | 2005-06-15 | American Home Products Corpoir | Derivatives of cyclic thiocarbamates, pharmaceutical composition including noted derivatives of cyclic thiocarbamates and active ingredients of medicines as modulators of progesterone receptors |
| DE20301728U1 (de) | 2002-10-11 | 2004-03-11 | Ligand Pharmaceuticals, Inc., San Diego | 5-substituierte 7,9-Difluor-5H-Chromeno(3,4-f) -Chinolin-Verbindungen als selektive Progesteronrezeptormodulator-Verbindungen |
| EP1558618A1 (en) | 2002-10-11 | 2005-08-03 | Ligand Pharmaceuticals, Inc. | 5-(1 ,1 -CYCLOALKYL/ALKENYL)METHYLIDENE 1,2-DIHYDRO- 5H /-CHROMENO[3,4-f ] QUINOLINES AS SELECTIVE PROGESTERONE RECEPTOR MODULATOR COMPOUNDS |
| AU2003258050A1 (en) | 2002-10-11 | 2004-05-04 | Ligand Pharmaceuticals Incorporated | 5-cycloalkenyl 5h-chromeno(3,4-f)quinoline derivatives as selective progesterone receptor modulator compounds |
-
2003
- 2003-08-04 EP EP03808050A patent/EP1558618A1/en not_active Withdrawn
- 2003-08-04 MX MXPA05003800A patent/MXPA05003800A/es unknown
- 2003-08-04 WO PCT/US2003/024416 patent/WO2004033459A1/en not_active Ceased
- 2003-08-04 CA CA002501833A patent/CA2501833A1/en not_active Abandoned
- 2003-08-04 AR AR20030102796A patent/AR040783A1/es not_active Application Discontinuation
- 2003-08-04 AU AU2003258047A patent/AU2003258047A1/en not_active Abandoned
- 2003-08-04 JP JP2004543231A patent/JP2006504736A/ja active Pending
- 2003-10-10 US US10/684,227 patent/US7084151B2/en not_active Expired - Lifetime
-
2006
- 2006-06-02 US US11/445,844 patent/US20060223839A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003258047A1 (en) | 2004-05-04 |
| WO2004033459A1 (en) | 2004-04-22 |
| AR040783A1 (es) | 2005-04-20 |
| US7084151B2 (en) | 2006-08-01 |
| EP1558618A1 (en) | 2005-08-03 |
| US20060223839A1 (en) | 2006-10-05 |
| US20040147530A1 (en) | 2004-07-29 |
| MXPA05003800A (es) | 2005-06-08 |
| JP2006504736A (ja) | 2006-02-09 |
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