RU2007101703A - Индолы, полезные при лечении воспаления - Google Patents
Индолы, полезные при лечении воспаления Download PDFInfo
- Publication number
- RU2007101703A RU2007101703A RU2007101703/04A RU2007101703A RU2007101703A RU 2007101703 A RU2007101703 A RU 2007101703A RU 2007101703/04 A RU2007101703/04 A RU 2007101703/04A RU 2007101703 A RU2007101703 A RU 2007101703A RU 2007101703 A RU2007101703 A RU 2007101703A
- Authority
- RU
- Russia
- Prior art keywords
- group
- optionally substituted
- compound according
- alkyl
- compound
- Prior art date
Links
- 206010061218 Inflammation Diseases 0.000 title claims abstract 7
- 230000004054 inflammatory process Effects 0.000 title claims abstract 7
- 150000001875 compounds Chemical class 0.000 claims abstract 48
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 10
- 150000003839 salts Chemical class 0.000 claims abstract 9
- 201000010099 disease Diseases 0.000 claims abstract 7
- 101710096361 Prostaglandin E synthase Proteins 0.000 claims abstract 5
- 230000000694 effects Effects 0.000 claims abstract 5
- 102100033076 Prostaglandin E synthase Human genes 0.000 claims abstract 3
- 125000001424 substituent group Chemical group 0.000 claims 26
- 125000005843 halogen group Chemical group 0.000 claims 20
- 229910052739 hydrogen Inorganic materials 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 239000001257 hydrogen Substances 0.000 claims 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 239000002671 adjuvant Substances 0.000 claims 10
- 125000003118 aryl group Chemical group 0.000 claims 9
- 125000001072 heteroaryl group Chemical group 0.000 claims 9
- 125000004429 atom Chemical group 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 6
- 125000005842 heteroatom Chemical group 0.000 claims 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 6
- -1 methylenedioxy, difluoromethylenedioxy Chemical group 0.000 claims 6
- 239000003085 diluting agent Substances 0.000 claims 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 125000004122 cyclic group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000000034 method Methods 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 208000035475 disorder Diseases 0.000 claims 3
- 229940124597 therapeutic agent Drugs 0.000 claims 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 201000004624 Dermatitis Diseases 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 208000010668 atopic eczema Diseases 0.000 claims 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- 102000004023 5-Lipoxygenase-Activating Proteins Human genes 0.000 claims 1
- 108090000411 5-Lipoxygenase-Activating Proteins Proteins 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 201000001320 Atherosclerosis Diseases 0.000 claims 1
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 206010006811 Bursitis Diseases 0.000 claims 1
- 206010010741 Conjunctivitis Diseases 0.000 claims 1
- 206010010904 Convulsion Diseases 0.000 claims 1
- 208000005171 Dysmenorrhea Diseases 0.000 claims 1
- 206010013935 Dysmenorrhoea Diseases 0.000 claims 1
- 208000001640 Fibromyalgia Diseases 0.000 claims 1
- 206010017533 Fungal infection Diseases 0.000 claims 1
- 201000005569 Gout Diseases 0.000 claims 1
- 206010019233 Headaches Diseases 0.000 claims 1
- 208000017604 Hodgkin disease Diseases 0.000 claims 1
- 208000010747 Hodgkins lymphoma Diseases 0.000 claims 1
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 1
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 1
- 208000019693 Lung disease Diseases 0.000 claims 1
- 208000019695 Migraine disease Diseases 0.000 claims 1
- 208000031888 Mycoses Diseases 0.000 claims 1
- 208000010191 Osteitis Deformans Diseases 0.000 claims 1
- 208000027868 Paget disease Diseases 0.000 claims 1
- 206010033645 Pancreatitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010037660 Pyrexia Diseases 0.000 claims 1
- 206010039705 Scleritis Diseases 0.000 claims 1
- 208000025865 Ulcer Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- 208000036142 Viral infection Diseases 0.000 claims 1
- 230000000172 allergic effect Effects 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- 208000006673 asthma Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 238000011260 co-administration Methods 0.000 claims 1
- 208000029078 coronary artery disease Diseases 0.000 claims 1
- 206010012601 diabetes mellitus Diseases 0.000 claims 1
- XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 claims 1
- 210000003017 ductus arteriosus Anatomy 0.000 claims 1
- 210000001035 gastrointestinal tract Anatomy 0.000 claims 1
- 231100000869 headache Toxicity 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 230000002757 inflammatory effect Effects 0.000 claims 1
- 201000004614 iritis Diseases 0.000 claims 1
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 1
- GWNVDXQDILPJIG-NXOLIXFESA-N leukotriene C4 Chemical compound CCCCC\C=C/C\C=C/C=C/C=C/[C@H]([C@@H](O)CCCC(O)=O)SC[C@@H](C(=O)NCC(O)=O)NC(=O)CC[C@H](N)C(O)=O GWNVDXQDILPJIG-NXOLIXFESA-N 0.000 claims 1
- 208000027202 mammary Paget disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 206010027599 migraine Diseases 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000008383 nephritis Diseases 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 238000012261 overproduction Methods 0.000 claims 1
- 208000028169 periodontal disease Diseases 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 230000000392 somatic effect Effects 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 231100000397 ulcer Toxicity 0.000 claims 1
- 230000009385 viral infection Effects 0.000 claims 1
- 230000029663 wound healing Effects 0.000 claims 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic 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
- C07D401/02—Heterocyclic 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
- C07D401/12—Heterocyclic 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 chain containing hetero atoms as chain links
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pain & Pain Management (AREA)
- Dermatology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Immunology (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Hematology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Reproductive Health (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US58040204P | 2004-06-18 | 2004-06-18 | |
| US60/580,402 | 2004-06-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2007101703A true RU2007101703A (ru) | 2008-07-27 |
Family
ID=34956078
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007101703/04A RU2007101703A (ru) | 2004-06-18 | 2005-06-17 | Индолы, полезные при лечении воспаления |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US20080188473A1 (enExample) |
| EP (1) | EP1778633B1 (enExample) |
| JP (1) | JP2008502670A (enExample) |
| KR (1) | KR20070029809A (enExample) |
| CN (1) | CN101006054A (enExample) |
| AT (1) | ATE416161T1 (enExample) |
| AU (1) | AU2005254783A1 (enExample) |
| BR (1) | BRPI0512253A (enExample) |
| CA (1) | CA2570531A1 (enExample) |
| DE (1) | DE602005011452D1 (enExample) |
| ES (1) | ES2321422T3 (enExample) |
| IL (1) | IL179607A0 (enExample) |
| MX (1) | MXPA06014536A (enExample) |
| RU (1) | RU2007101703A (enExample) |
| WO (1) | WO2005123674A1 (enExample) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20070028553A (ko) | 2004-06-18 | 2007-03-12 | 바이올리폭스 에이비 | 염증 치료에 유용한 인돌 |
| US20080146616A1 (en) * | 2004-06-18 | 2008-06-19 | Kristofer Olofsson | Indoles Useful in the Treatment of Inflammation |
| WO2006077366A1 (en) | 2005-01-19 | 2006-07-27 | Biolipox Ab | Indoles useful in the treatment of inflammation |
| EP1841736A1 (en) * | 2005-01-19 | 2007-10-10 | Biolipox AB | Indoles useful in the treatment of inflammation |
| US7977359B2 (en) | 2005-11-04 | 2011-07-12 | Amira Pharmaceuticals, Inc. | 5-lipdxygenase-activating protein (FLAP) inhibitors |
| GB2431927B (en) | 2005-11-04 | 2010-03-17 | Amira Pharmaceuticals Inc | 5-Lipoxygenase-activating protein (FLAP) inhibitors |
| US8399666B2 (en) | 2005-11-04 | 2013-03-19 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| MX2009011210A (es) * | 2007-04-16 | 2009-10-30 | Abbott Lab | Inhibidores de mcl1 de indol 7-no sustituido. |
| US20100298343A1 (en) * | 2007-10-05 | 2010-11-25 | John Howard Hutchinson | 5-lipoxygenase-activating protein (flap) inhibitors |
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| US20110160249A1 (en) | 2008-05-23 | 2011-06-30 | Schaab Kevin Murray | 5-lipoxygenase-activating protein inhibitor |
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| US8546431B2 (en) | 2008-10-01 | 2013-10-01 | Panmira Pharmaceuticals, Llc | 5-lipoxygenase-activating protein (FLAP) inhibitors |
| US20120029016A1 (en) | 2008-12-30 | 2012-02-02 | Biolipox Ab | Indoles Useful in the Treatment of Inflammation |
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| US8586604B2 (en) | 2010-08-20 | 2013-11-19 | Boehringer Ingelheim International Gmbh | Inhibitors of the microsomal prostaglandin E2 synthase-1 |
| US8486968B2 (en) | 2010-12-10 | 2013-07-16 | Boehringer Ingelheim International Gmbh | Compounds |
| US8674113B2 (en) | 2010-12-10 | 2014-03-18 | Boehringer Ingelheim International Gmbh | Compounds |
| US8466186B2 (en) | 2010-12-10 | 2013-06-18 | Boehringer Ingelheim International Gmbh | Compounds |
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| US5081138A (en) * | 1986-12-17 | 1992-01-14 | Merck Frosst Canada, Inc. | 3-hetero-substituted-n-benzyl-indoles and prevention of leucotriene synthesis therewith |
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| US5374615A (en) * | 1990-10-31 | 1994-12-20 | E. R. Squibb & Sons, Inc. | Indole- and benzimidazole-substituted imidazole and benzimidazole derivatives |
| US5189054A (en) * | 1990-11-02 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | 3-amidoindolyl derivatives and pharmaceutical compositions thereof |
| US5294722A (en) * | 1992-04-16 | 1994-03-15 | E. R. Squibb & Sons, Inc. | Process for the preparation of imidazoles useful in angiotensin II antagonism |
| US5236916A (en) * | 1992-05-26 | 1993-08-17 | E. R. Squibb & Sons, Inc. | Oxadiazinone substituted indole and benzimidazole derivatives |
| TW229140B (enExample) * | 1992-06-05 | 1994-09-01 | Shell Internat Res Schappej B V | |
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| GB9716656D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| GB9716657D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| DE19742263A1 (de) * | 1997-09-25 | 1999-04-01 | Asta Medica Ag | Neue spezifische Immunophilin-Liganden als Antiasthmatika, Antiallergika, Antirheumatika, Immunsuppressiva, Antipsoriatika, Neuroprotektiva |
| HU227568B1 (en) * | 1997-12-24 | 2011-08-29 | Sanofi Aventis Deutschland | Indole derivatives, as inhibitors os factor xa |
| GB9803228D0 (en) * | 1998-02-17 | 1998-04-08 | Zeneca Ltd | Chemical compounds |
| US6828344B1 (en) * | 1998-02-25 | 2004-12-07 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| US6500853B1 (en) * | 1998-02-28 | 2002-12-31 | Genetics Institute, Llc | Inhibitors of phospholipase enzymes |
| GB9902453D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902459D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902452D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| GB9902455D0 (en) * | 1999-02-05 | 1999-03-24 | Zeneca Ltd | Chemical compounds |
| JP2001069477A (ja) * | 1999-08-31 | 2001-03-16 | Sony Corp | 番組提供システム及び番組提供方法 |
| US6353007B1 (en) * | 2000-07-13 | 2002-03-05 | Boehringer Ingelheim Pharmaceuticals, Inc. | Substituted 1-(4-aminophenyl)indoles and their use as anti-inflammatory agents |
| PL366068A1 (en) * | 2000-10-10 | 2005-01-24 | Smithkline Beecham Corporation | Substituted indoles, pharmaceutical compositions containing such indoles and their use as ppar-gamma binding agents |
| JP2008527027A (ja) * | 2005-01-19 | 2008-07-24 | バイオリポックス エービー | 炎症の治療に有用なインドール類 |
-
2005
- 2005-06-17 KR KR1020077001306A patent/KR20070029809A/ko not_active Withdrawn
- 2005-06-17 DE DE602005011452T patent/DE602005011452D1/de not_active Expired - Fee Related
- 2005-06-17 ES ES05751820T patent/ES2321422T3/es not_active Expired - Lifetime
- 2005-06-17 JP JP2007516044A patent/JP2008502670A/ja not_active Withdrawn
- 2005-06-17 BR BRPI0512253-8A patent/BRPI0512253A/pt not_active IP Right Cessation
- 2005-06-17 CN CNA2005800284017A patent/CN101006054A/zh active Pending
- 2005-06-17 AT AT05751820T patent/ATE416161T1/de not_active IP Right Cessation
- 2005-06-17 MX MXPA06014536A patent/MXPA06014536A/es unknown
- 2005-06-17 CA CA002570531A patent/CA2570531A1/en not_active Abandoned
- 2005-06-17 AU AU2005254783A patent/AU2005254783A1/en not_active Abandoned
- 2005-06-17 WO PCT/GB2005/002396 patent/WO2005123674A1/en not_active Ceased
- 2005-06-17 EP EP05751820A patent/EP1778633B1/en not_active Expired - Lifetime
- 2005-06-17 US US11/629,627 patent/US20080188473A1/en not_active Abandoned
- 2005-06-17 RU RU2007101703/04A patent/RU2007101703A/ru not_active Application Discontinuation
-
2006
- 2006-11-27 IL IL179607A patent/IL179607A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0512253A (pt) | 2008-02-19 |
| ES2321422T3 (es) | 2009-06-05 |
| CA2570531A1 (en) | 2005-12-29 |
| EP1778633B1 (en) | 2008-12-03 |
| EP1778633A1 (en) | 2007-05-02 |
| DE602005011452D1 (de) | 2009-01-15 |
| CN101006054A (zh) | 2007-07-25 |
| JP2008502670A (ja) | 2008-01-31 |
| ATE416161T1 (de) | 2008-12-15 |
| IL179607A0 (en) | 2007-05-15 |
| MXPA06014536A (es) | 2007-06-05 |
| US20080188473A1 (en) | 2008-08-07 |
| AU2005254783A1 (en) | 2005-12-29 |
| KR20070029809A (ko) | 2007-03-14 |
| WO2005123674A1 (en) | 2005-12-29 |
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Legal Events
| Date | Code | Title | Description |
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| FA92 | Acknowledgement of application withdrawn (lack of supplementary materials submitted) |
Effective date: 20090909 |