CA2468466A1 - Use of pregnane-diones or diols as neuropathic analgesic agents - Google Patents
Use of pregnane-diones or diols as neuropathic analgesic agents Download PDFInfo
- Publication number
- CA2468466A1 CA2468466A1 CA002468466A CA2468466A CA2468466A1 CA 2468466 A1 CA2468466 A1 CA 2468466A1 CA 002468466 A CA002468466 A CA 002468466A CA 2468466 A CA2468466 A CA 2468466A CA 2468466 A1 CA2468466 A1 CA 2468466A1
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- alkanoyl
- alkenyl
- formula
- compound
- 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
Links
- 230000002981 neuropathic effect Effects 0.000 title description 16
- XZHKZJXZRWFLCJ-RKFIYKRSSA-N (8R,9S,10S,13R,14S,17R)-17-ethyl-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,17-dodecahydro-1H-cyclopenta[a]phenanthrene-15,16-dione Chemical class [C@@H]12C(C([C@H](CC)[C@@]1(C)CC[C@H]1[C@H]2CCC2CCCC[C@]12C)=O)=O XZHKZJXZRWFLCJ-RKFIYKRSSA-N 0.000 title description 7
- 239000000730 antalgic agent Substances 0.000 title description 5
- 150000002009 diols Chemical class 0.000 title description 2
- 208000004296 neuralgia Diseases 0.000 claims abstract description 56
- 208000021722 neuropathic pain Diseases 0.000 claims abstract description 55
- 241000124008 Mammalia Species 0.000 claims abstract description 25
- 230000004044 response Effects 0.000 claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 206010039897 Sedation Diseases 0.000 claims abstract description 20
- 230000036592 analgesia Effects 0.000 claims abstract description 20
- 230000036280 sedation Effects 0.000 claims abstract description 20
- 230000001939 inductive effect Effects 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 107
- 238000000034 method Methods 0.000 claims description 69
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 39
- QRJOQYLXZPQQMX-FWROMSNXSA-N acetic acid [2-[(3R,5S,8S,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethyl-11-oxo-1,2,3,4,5,6,7,8,9,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] ester Chemical compound C([C@@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H](C(=O)COC(=O)C)[C@@]2(C)CC1=O QRJOQYLXZPQQMX-FWROMSNXSA-N 0.000 claims description 37
- 229950000888 alfadolone acetate Drugs 0.000 claims description 37
- 125000001589 carboacyl group Chemical group 0.000 claims description 32
- BRUQQQPBMZOVGD-XFKAJCMBSA-N Oxycodone Chemical compound O=C([C@@H]1O2)CC[C@@]3(O)[C@H]4CC5=CC=C(OC)C2=C5[C@@]13CCN4C BRUQQQPBMZOVGD-XFKAJCMBSA-N 0.000 claims description 25
- 229960002085 oxycodone Drugs 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims description 24
- 239000003814 drug Substances 0.000 claims description 22
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 21
- 230000000202 analgesic effect Effects 0.000 claims description 20
- 229940079593 drug Drugs 0.000 claims description 20
- 150000003839 salts Chemical class 0.000 claims description 13
- 229960005181 morphine Drugs 0.000 claims description 12
- 208000032131 Diabetic Neuropathies Diseases 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 229960002428 fentanyl Drugs 0.000 claims description 9
- 241000282414 Homo sapiens Species 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 claims description 7
- 208000023890 Complex Regional Pain Syndromes Diseases 0.000 claims description 5
- 208000004983 Phantom Limb Diseases 0.000 claims description 5
- 206010056238 Phantom pain Diseases 0.000 claims description 5
- OROGSEYTTFOCAN-DNJOTXNNSA-N codeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC OROGSEYTTFOCAN-DNJOTXNNSA-N 0.000 claims description 5
- 239000000651 prodrug Substances 0.000 claims description 5
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- 206010044652 trigeminal neuralgia Diseases 0.000 claims description 5
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- 206010036376 Postherpetic Neuralgia Diseases 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229960004126 codeine Drugs 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- OROGSEYTTFOCAN-UHFFFAOYSA-N hydrocodone Natural products C1C(N(CCC234)C)C2C=CC(O)C3OC2=C4C1=CC=C2OC OROGSEYTTFOCAN-UHFFFAOYSA-N 0.000 claims description 4
- 208000015181 infectious disease Diseases 0.000 claims description 4
- AKNNEGZIBPJZJG-MSOLQXFVSA-N (-)-noscapine Chemical compound CN1CCC2=CC=3OCOC=3C(OC)=C2[C@@H]1[C@@H]1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-MSOLQXFVSA-N 0.000 claims description 3
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N (R,R)-tramadol Chemical compound COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-ZBFHGGJFSA-N 0.000 claims description 3
- USSIQXCVUWKGNF-UHFFFAOYSA-N 6-(dimethylamino)-4,4-diphenylheptan-3-one Chemical compound C=1C=CC=CC=1C(CC(C)N(C)C)(C(=O)CC)C1=CC=CC=C1 USSIQXCVUWKGNF-UHFFFAOYSA-N 0.000 claims description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 claims description 3
- IJVCSMSMFSCRME-KBQPJGBKSA-N Dihydromorphine Chemical compound O([C@H]1[C@H](CC[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O IJVCSMSMFSCRME-KBQPJGBKSA-N 0.000 claims description 3
- XADCESSVHJOZHK-UHFFFAOYSA-N Meperidine Chemical compound C=1C=CC=CC=1C1(C(=O)OCC)CCN(C)CC1 XADCESSVHJOZHK-UHFFFAOYSA-N 0.000 claims description 3
- IDBPHNDTYPBSNI-UHFFFAOYSA-N N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide Chemical compound C1CN(CCN2C(N(CC)N=N2)=O)CCC1(COC)N(C(=O)CC)C1=CC=CC=C1 IDBPHNDTYPBSNI-UHFFFAOYSA-N 0.000 claims description 3
- UQCNKQCJZOAFTQ-ISWURRPUSA-N Oxymorphone Chemical compound O([C@H]1C(CC[C@]23O)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O UQCNKQCJZOAFTQ-ISWURRPUSA-N 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 3
- 229960001391 alfentanil Drugs 0.000 claims description 3
- AKNNEGZIBPJZJG-UHFFFAOYSA-N alpha-noscapine Natural products CN1CCC2=CC=3OCOC=3C(OC)=C2C1C1C2=CC=C(OC)C(OC)=C2C(=O)O1 AKNNEGZIBPJZJG-UHFFFAOYSA-N 0.000 claims description 3
- VMWNQDUVQKEIOC-CYBMUJFWSA-N apomorphine Chemical compound C([C@H]1N(C)CC2)C3=CC=C(O)C(O)=C3C3=C1C2=CC=C3 VMWNQDUVQKEIOC-CYBMUJFWSA-N 0.000 claims description 3
- 229960004046 apomorphine Drugs 0.000 claims description 3
- RMRJXGBAOAMLHD-IHFGGWKQSA-N buprenorphine Chemical compound C([C@]12[C@H]3OC=4C(O)=CC=C(C2=4)C[C@@H]2[C@]11CC[C@]3([C@H](C1)[C@](C)(O)C(C)(C)C)OC)CN2CC1CC1 RMRJXGBAOAMLHD-IHFGGWKQSA-N 0.000 claims description 3
- 229960001736 buprenorphine Drugs 0.000 claims description 3
- 229950003851 desomorphine Drugs 0.000 claims description 3
- LNNWVNGFPYWNQE-GMIGKAJZSA-N desomorphine Chemical compound C1C2=CC=C(O)C3=C2[C@]24CCN(C)[C@H]1[C@@H]2CCC[C@@H]4O3 LNNWVNGFPYWNQE-GMIGKAJZSA-N 0.000 claims description 3
- INUNXTSAACVKJS-OAQYLSRUSA-N dextromoramide Chemical compound C([C@@H](C)C(C(=O)N1CCCC1)(C=1C=CC=CC=1)C=1C=CC=CC=1)N1CCOCC1 INUNXTSAACVKJS-OAQYLSRUSA-N 0.000 claims description 3
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- 229960004193 dextropropoxyphene Drugs 0.000 claims description 3
- XLMALTXPSGQGBX-GCJKJVERSA-N dextropropoxyphene Chemical compound C([C@](OC(=O)CC)([C@H](C)CN(C)C)C=1C=CC=CC=1)C1=CC=CC=C1 XLMALTXPSGQGBX-GCJKJVERSA-N 0.000 claims description 3
- 229960000920 dihydrocodeine Drugs 0.000 claims description 3
- RBOXVHNMENFORY-DNJOTXNNSA-N dihydrocodeine Chemical compound C([C@H]1[C@H](N(CC[C@@]112)C)C3)C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC RBOXVHNMENFORY-DNJOTXNNSA-N 0.000 claims description 3
- XYYVYLMBEZUESM-UHFFFAOYSA-N dihydrocodeine Natural products C1C(N(CCC234)C)C2C=CC(=O)C3OC2=C4C1=CC=C2OC XYYVYLMBEZUESM-UHFFFAOYSA-N 0.000 claims description 3
- WVLOADHCBXTIJK-YNHQPCIGSA-N hydromorphone Chemical compound O([C@H]1C(CC[C@H]23)=O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O WVLOADHCBXTIJK-YNHQPCIGSA-N 0.000 claims description 3
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- VOKSWYLNZZRQPF-GDIGMMSISA-N pentazocine Chemical compound C1C2=CC=C(O)C=C2[C@@]2(C)[C@@H](C)[C@@H]1N(CC=C(C)C)CC2 VOKSWYLNZZRQPF-GDIGMMSISA-N 0.000 claims description 3
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- TVYLLZQTGLZFBW-GOEBONIOSA-N tramadol Natural products COC1=CC=CC([C@@]2(O)[C@@H](CCCC2)CN(C)C)=C1 TVYLLZQTGLZFBW-GOEBONIOSA-N 0.000 claims description 3
- LGFMXOTUSSVQJV-NEYUFSEYSA-N (4r,4ar,7s,7ar,12bs)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol;(4r,4ar,7s,7ar,12bs)-3-methyl-2,4,4a,7,7a,13-hexahydro-1h-4,12-methanobenzofuro[3,2-e]isoquinoline-7,9-diol;1-[(3,4-dimethoxyphenyl)methyl]-6 Chemical compound Cl.Cl.Cl.O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O.C([C@H]1[C@H](N(CC[C@@]112)C)C3)=C[C@H](O)[C@@H]1OC1=C2C3=CC=C1OC.C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 LGFMXOTUSSVQJV-NEYUFSEYSA-N 0.000 claims description 2
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- 150000003128 pregnanes Chemical class 0.000 abstract 1
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Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
- A61K31/573—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone substituted in position 21, e.g. cortisone, dexamethasone, prednisone or aldosterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
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- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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
- A61P25/20—Hypnotics; Sedatives
Landscapes
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AUPR7319A AUPR731901A0 (en) | 2001-08-28 | 2001-08-28 | Method of treatment |
| AUPR7319 | 2001-08-28 | ||
| PCT/AU2002/001144 WO2003018027A1 (en) | 2001-08-28 | 2002-08-28 | Use of pregnane-diones or diols as neuropathic analgesic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2468466A1 true CA2468466A1 (en) | 2003-03-06 |
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ID=3831271
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002468466A Abandoned CA2468466A1 (en) | 2001-08-28 | 2002-08-28 | Use of pregnane-diones or diols as neuropathic analgesic agents |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US20050009796A1 (enExample) |
| EP (1) | EP1450817A4 (enExample) |
| JP (1) | JP2005504776A (enExample) |
| CN (2) | CN1549719A (enExample) |
| AU (2) | AUPR731901A0 (enExample) |
| BR (1) | BR0212205A (enExample) |
| CA (1) | CA2468466A1 (enExample) |
| MX (1) | MXPA04001807A (enExample) |
| RU (1) | RU2346690C2 (enExample) |
| WO (1) | WO2003018027A1 (enExample) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10141650C1 (de) | 2001-08-24 | 2002-11-28 | Lohmann Therapie Syst Lts | Transdermales Therapeutisches System mit Fentanyl bzw. verwandten Substanzen |
| GB0324423D0 (en) * | 2003-10-18 | 2003-11-19 | Vernalis Cambridge Ltd | Analgesia method |
| US20060009432A1 (en) * | 2004-07-09 | 2006-01-12 | Roger Whiting | Use of neurosteroids to treat neuropathic pain |
| RU2306929C1 (ru) * | 2005-12-28 | 2007-09-27 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции комбинацией индапамида и l-аргинина при l-name-индуцированном дефиците оксида азота |
| RU2306924C1 (ru) * | 2005-12-28 | 2007-09-27 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции комбинацией лозартана и резвератрола при l-name-индуцированном дефиците оксида азота |
| RU2296566C1 (ru) * | 2005-12-28 | 2007-04-10 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции комбинацией амлодипина и l-аргинина при l-name-индуцированном дефиците оксида азота |
| RU2306930C1 (ru) * | 2005-12-28 | 2007-09-27 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции комбинацией лозартана и l-аргинина при l-name-индуцированном дефиците оксида азота |
| RU2302241C1 (ru) * | 2005-12-28 | 2007-07-10 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции комбинацией индапамида и резвератрола при l-name-индуцированном дефиците оксида азота |
| JPWO2008120562A1 (ja) * | 2007-04-02 | 2010-07-15 | 東洋紡績株式会社 | 帯状疱疹後神経痛治療用錠剤および帯状疱疹後神経痛の治療方法 |
| RU2364393C1 (ru) * | 2008-03-19 | 2009-08-20 | Михаил Владимирович Покровский | Способ коррекции эндотелиальной дисфункции пикамилоном при l-name индуцированном дефиците оксида азота |
| WO2010025316A1 (en) * | 2008-08-29 | 2010-03-04 | Jeffrey Comanor | Composition and methods for relief of neuropathological pain |
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| GB1317184A (en) * | 1969-06-20 | 1973-05-16 | Glaxo Lab Ltd | Steroid-containing pharmaceutical preparations |
| GB1373913A (en) * | 1970-12-17 | 1974-11-13 | Glaxo Lab Ltd | Pharmaceutical compositions |
| US5888996A (en) * | 1995-07-26 | 1999-03-30 | Trustees Of Boston University | Inhibition of NMDA receptor activity and modulation of glutamate-mediated synaptic activity |
| JP4313435B2 (ja) * | 1995-07-24 | 2009-08-12 | トラスティーズ オブ ボストン ユニバーシティー | プレグネノロンサルフェート誘導体によるｎｍｄａレセプター活性の抑制 |
| AUPN498095A0 (en) * | 1995-08-23 | 1995-09-14 | Goodchild, Colin Stanley | Compounds and compositions |
| GB9607034D0 (en) * | 1996-04-03 | 1996-06-05 | Leo Pharm Prod Ltd | Chemical compounds |
| US6048848A (en) * | 1996-08-23 | 2000-04-11 | Monash University | Use of pregnane-diones as analgesic agents |
| US6787530B1 (en) * | 1996-08-23 | 2004-09-07 | Monash University | Use of pregnane-diones as analgesic agents |
| AU782250B2 (en) * | 1999-08-31 | 2005-07-14 | Trustees Of Boston University | Effect of steroids on NMDA receptors depends on subunit composition |
| US20030027833A1 (en) * | 2001-05-07 | 2003-02-06 | Cleary Gary W. | Compositions and delivery systems for administration of a local anesthetic agent |
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2001
- 2001-08-28 AU AUPR7319A patent/AUPR731901A0/en not_active Abandoned
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2002
- 2002-08-28 RU RU2004109517/14A patent/RU2346690C2/ru not_active IP Right Cessation
- 2002-08-28 CN CNA02817027XA patent/CN1549719A/zh active Pending
- 2002-08-28 US US10/487,922 patent/US20050009796A1/en not_active Abandoned
- 2002-08-28 EP EP02759883A patent/EP1450817A4/en not_active Withdrawn
- 2002-08-28 BR BR0212205-7A patent/BR0212205A/pt not_active IP Right Cessation
- 2002-08-28 CN CNA2009101264152A patent/CN101590062A/zh active Pending
- 2002-08-28 JP JP2003522545A patent/JP2005504776A/ja active Pending
- 2002-08-28 MX MXPA04001807A patent/MXPA04001807A/es not_active Application Discontinuation
- 2002-08-28 CA CA002468466A patent/CA2468466A1/en not_active Abandoned
- 2002-08-28 WO PCT/AU2002/001144 patent/WO2003018027A1/en not_active Ceased
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2008
- 2008-03-03 US US12/041,593 patent/US20080227764A1/en not_active Abandoned
- 2008-06-20 AU AU2008202729A patent/AU2008202729A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1549719A (zh) | 2004-11-24 |
| RU2004109517A (ru) | 2005-06-27 |
| MXPA04001807A (es) | 2005-03-07 |
| US20050009796A1 (en) | 2005-01-13 |
| EP1450817A1 (en) | 2004-09-01 |
| US20080227764A1 (en) | 2008-09-18 |
| BR0212205A (pt) | 2004-09-21 |
| AUPR731901A0 (en) | 2001-09-20 |
| WO2003018027A1 (en) | 2003-03-06 |
| AU2008202729A1 (en) | 2008-07-17 |
| RU2346690C2 (ru) | 2009-02-20 |
| CN101590062A (zh) | 2009-12-02 |
| EP1450817A4 (en) | 2009-02-25 |
| JP2005504776A (ja) | 2005-02-17 |
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