RU2406724C2 - Конденсированные трициклические соединения в качестве ингибиторов фактора некроза опухоли альфа - Google Patents
Конденсированные трициклические соединения в качестве ингибиторов фактора некроза опухоли альфа Download PDFInfo
- Publication number
- RU2406724C2 RU2406724C2 RU2007121682/04A RU2007121682A RU2406724C2 RU 2406724 C2 RU2406724 C2 RU 2406724C2 RU 2007121682/04 A RU2007121682/04 A RU 2007121682/04A RU 2007121682 A RU2007121682 A RU 2007121682A RU 2406724 C2 RU2406724 C2 RU 2406724C2
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- Prior art keywords
- alkyl
- compound
- hydrogen
- formula
- methyl
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- 150000001875 compounds Chemical class 0.000 title claims abstract 80
- 206010054094 Tumour necrosis Diseases 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 109
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 61
- 239000001257 hydrogen Substances 0.000 claims abstract 61
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 33
- 229910052736 halogen Chemical group 0.000 claims abstract 29
- 150000002367 halogens Chemical group 0.000 claims abstract 29
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract 27
- 150000002431 hydrogen Chemical group 0.000 claims abstract 26
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract 17
- 150000003839 salts Chemical class 0.000 claims abstract 16
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims abstract 13
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 13
- 238000000034 method Methods 0.000 claims abstract 11
- 125000005842 heteroatom Chemical group 0.000 claims abstract 9
- 125000005129 aryl carbonyl group Chemical group 0.000 claims abstract 8
- 239000003814 drug Substances 0.000 claims abstract 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 6
- 230000000694 effects Effects 0.000 claims abstract 6
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 230000002401 inhibitory effect Effects 0.000 claims abstract 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 5
- 229910052760 oxygen Chemical group 0.000 claims abstract 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 4
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims abstract 4
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 4
- 239000001301 oxygen Chemical group 0.000 claims abstract 4
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 3
- -1 [1,4] diazepanyl Chemical group 0.000 claims 28
- 125000004193 piperazinyl group Chemical group 0.000 claims 10
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 9
- 102000000852 Tumor Necrosis Factor-alpha Human genes 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 8
- 150000004702 methyl esters Chemical class 0.000 claims 8
- MZOFCQQQCNRIBI-VMXHOPILSA-N (3s)-4-[[(2s)-1-[[(2s)-1-[[(1s)-1-carboxy-2-hydroxyethyl]amino]-4-methyl-1-oxopentan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-3-[[2-[[(2s)-2,6-diaminohexanoyl]amino]acetyl]amino]-4-oxobutanoic acid Chemical compound OC[C@@H](C(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@@H](N)CCCCN MZOFCQQQCNRIBI-VMXHOPILSA-N 0.000 claims 7
- 238000006243 chemical reaction Methods 0.000 claims 7
- 125000003282 alkyl amino group Chemical group 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 6
- 238000004519 manufacturing process Methods 0.000 claims 6
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 6
- 230000002159 abnormal effect Effects 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 5
- 241000124008 Mammalia Species 0.000 claims 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 230000007062 hydrolysis Effects 0.000 claims 4
- 238000006460 hydrolysis reaction Methods 0.000 claims 4
- 150000002828 nitro derivatives Chemical class 0.000 claims 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 3
- 239000000460 chlorine Substances 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 230000001684 chronic effect Effects 0.000 claims 3
- 230000004968 inflammatory condition Effects 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- 229910052717 sulfur Chemical group 0.000 claims 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 2
- 208000011231 Crohn disease Diseases 0.000 claims 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- 206010061598 Immunodeficiency Diseases 0.000 claims 2
- 208000029462 Immunodeficiency disease Diseases 0.000 claims 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims 2
- 208000003456 Juvenile Arthritis Diseases 0.000 claims 2
- 206010059176 Juvenile idiopathic arthritis Diseases 0.000 claims 2
- 208000001132 Osteoporosis Diseases 0.000 claims 2
- 201000001263 Psoriatic Arthritis Diseases 0.000 claims 2
- 208000036824 Psoriatic arthropathy Diseases 0.000 claims 2
- 206010040070 Septic Shock Diseases 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 201000009961 allergic asthma Diseases 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 229910052794 bromium Inorganic materials 0.000 claims 2
- 208000019069 chronic childhood arthritis Diseases 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 2
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 230000001747 exhibiting effect Effects 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 230000007813 immunodeficiency Effects 0.000 claims 2
- 201000002215 juvenile rheumatoid arthritis Diseases 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 238000006396 nitration reaction Methods 0.000 claims 2
- 201000008482 osteoarthritis Diseases 0.000 claims 2
- 230000001590 oxidative effect Effects 0.000 claims 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 229920006395 saturated elastomer Polymers 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- 206010006895 Cachexia Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 201000003874 Common Variable Immunodeficiency Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 206010014824 Endotoxic shock Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 201000009906 Meningitis Diseases 0.000 claims 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
- 208000007452 Plasmacytoma Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 206010040047 Sepsis Diseases 0.000 claims 1
- 241000534944 Thia Species 0.000 claims 1
- 206010053613 Type IV hypersensitivity reaction Diseases 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 206010047115 Vasculitis Diseases 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 1
- 206010002022 amyloidosis Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 150000001923 cyclic compounds Chemical class 0.000 claims 1
- HJZOOZBCIXESNA-UHFFFAOYSA-N cycloheptane dihydrochloride Chemical compound C1CCCCCC1.Cl.Cl HJZOOZBCIXESNA-UHFFFAOYSA-N 0.000 claims 1
- ZKNJGYBHKGDNCD-UHFFFAOYSA-N cycloheptane;hydrochloride Chemical compound Cl.C1CCCCCC1 ZKNJGYBHKGDNCD-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000006316 iso-butyl amino group Chemical group [H]N(*)C([H])([H])C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- GXHMMDRXHUIUMN-UHFFFAOYSA-N methanesulfonic acid Chemical compound CS(O)(=O)=O.CS(O)(=O)=O GXHMMDRXHUIUMN-UHFFFAOYSA-N 0.000 claims 1
- WRTMOQVDBQDRNW-UHFFFAOYSA-N methyl 10-chloro-1-methyl-8-piperazin-1-yl-6h-benzo[b][1,5]benzoxathiepine-3-carboxylate;hydrochloride Chemical compound Cl.C1=C2CSC3=CC(C(=O)OC)=CC(C)=C3OC2=C(Cl)C=C1N1CCNCC1 WRTMOQVDBQDRNW-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- RFIOZSIHFNEKFF-UHFFFAOYSA-N piperazine-1-carboxylic acid Chemical compound OC(=O)N1CCNCC1 RFIOZSIHFNEKFF-UHFFFAOYSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 claims 1
- 230000005951 type IV hypersensitivity Effects 0.000 claims 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 102000009270 Tumour necrosis factor alpha Human genes 0.000 abstract 1
- 108050000101 Tumour necrosis factor alpha Proteins 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
- C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
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- A61K31/33—Heterocyclic compounds
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/39—Heterocyclic compounds having sulfur as a ring hetero atom having oxygen in the same ring
-
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D411/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D411/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D411/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen and sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Physical Education & Sports Medicine (AREA)
- Virology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- AIDS & HIV (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN1226MU2004 | 2004-11-10 | ||
| IN1226/MUM/2004 | 2004-11-10 | ||
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| CA2756255A1 (en) | 2009-03-27 | 2010-09-30 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic hcv inhibitors |
| CN102595894A (zh) | 2009-08-27 | 2012-07-18 | 美国政府卫生与公众服务部 | 治疗疟疾和预防疟疾传播的化合物 |
| EP2512238B1 (en) | 2009-12-14 | 2014-06-25 | Merck Sharp & Dohme Corp. | Fused tricyclic compounds for the treatment of inflammatory disorders |
| WO2011073378A1 (en) * | 2009-12-18 | 2011-06-23 | Basilea Pharmaceutica Ag | Tricyclic antibiotics |
| US8822520B2 (en) | 2010-09-22 | 2014-09-02 | Presidio Pharmaceuticals, Inc. | Substituted bicyclic HCV inhibitors |
| WO2012050918A2 (en) * | 2010-09-29 | 2012-04-19 | Presidio Pharmaceutical, Inc. | Tricyclic fused ring inhibitors of hepatitis c |
| GB201507903D0 (en) * | 2015-05-08 | 2015-06-24 | Oncopeptides Ab | Process for preparation of nitrogen mustard derivatives |
| CN106995382A (zh) * | 2016-01-25 | 2017-08-01 | 济南和润化工科技有限公司 | 一种催化氢化法生产3-甲基-4-氨基苯甲酸的方法 |
| EP3436458B1 (en) * | 2016-04-01 | 2021-06-02 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| EA201892144A1 (ru) * | 2016-04-01 | 2019-04-30 | Юсб Байофарма Спрл | Конденсированные гексациклические производные имидазола в качестве модуляторов активности tnf |
| EA201892142A1 (ru) * | 2016-04-01 | 2019-04-30 | Юсб Байофарма Спрл | Конденсированные пентациклические производные имидазола в качестве модуляторов активности tnf |
| EP3436459B1 (en) * | 2016-04-01 | 2021-08-25 | UCB Biopharma SRL | Fused pentacyclic imidazole derivatives as modulators of tnf activity |
| CN106831460A (zh) * | 2017-02-24 | 2017-06-13 | 青铜峡市嘉华化工有限公司 | 3‑甲基‑4‑氨基苯甲酸的制备方法 |
| USD817148S1 (en) * | 2017-04-05 | 2018-05-08 | Dormakaba Canada Inc. | Locking system housing |
| CN107501106A (zh) * | 2017-08-14 | 2017-12-22 | 中涛新材料有限公司 | 一种催化加氢制备3‑甲基‑4‑氨基苯甲酸的方法 |
| CN113543852A (zh) | 2019-03-06 | 2021-10-22 | 第一三共株式会社 | 吡咯并吡唑衍生物 |
| CN115010621B (zh) * | 2022-07-21 | 2023-11-03 | 山东百启生物医药有限公司 | 一种4-溴-3-甲基苯甲腈的合成方法 |
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| WO1996031497A1 (en) * | 1995-04-07 | 1996-10-10 | Novo Nordisk A/S | Novel heterocyclic compounds |
| RU2177473C2 (ru) * | 1996-05-14 | 2001-12-27 | Италфармако С.П.А. | Соединения, обладающие противовоспалительной и иммунодепрессивной активностью и содержащие их фармацевтические композиции |
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| IL48807A0 (en) * | 1975-02-18 | 1976-03-31 | Syntex Inc | Novel 6,11-dihydrodibenzo-thiepin-11-ones,their preparation and compositions containing them |
| US4130654A (en) * | 1978-01-30 | 1978-12-19 | Syntex (U.S.A.) Inc. | Novel 4-(8X-6,11-dihydrodibenzo-[b.e.]-thiepin-11-one-3-yl)-4-oxobutyric acids, methods of preparation, compositions and uses thereof |
| IL57077A0 (en) * | 1978-04-21 | 1979-07-25 | Syntex Inc | 6,11-dihydrodibenzo-thiepin-11-one s-oxides their preparation and pharmaceutical compositions containing them |
| GB2094790B (en) * | 1981-03-13 | 1985-10-09 | Spofa Vereinigte Pharma Werke | Tricycle compounds |
| JPH0240662A (ja) | 1988-08-01 | 1990-02-09 | Ricoh Co Ltd | 電子写真用感光体 |
| US5036067A (en) * | 1990-03-14 | 1991-07-30 | Merck & Co., Inc. | Dibenzoheterocyclic hydroxamic acids and hydroxy ureas as inhibitors of 5-lipoxygenase |
| JPH08119920A (ja) | 1994-10-18 | 1996-05-14 | Kyowa Hakko Kogyo Co Ltd | 三環式アニリド誘導体 |
| JPH0940662A (ja) | 1995-05-24 | 1997-02-10 | Kyowa Hakko Kogyo Co Ltd | 三環式化合物 |
| JPH11130772A (ja) | 1997-10-28 | 1999-05-18 | Kyowa Hakko Kogyo Co Ltd | 含窒素複素環化合物 |
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| WO1996031497A1 (en) * | 1995-04-07 | 1996-10-10 | Novo Nordisk A/S | Novel heterocyclic compounds |
| RU2177473C2 (ru) * | 1996-05-14 | 2001-12-27 | Италфармако С.П.А. | Соединения, обладающие противовоспалительной и иммунодепрессивной активностью и содержащие их фармацевтические композиции |
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| US7834052B2 (en) | 2010-11-16 |
| AU2005303410B2 (en) | 2011-12-15 |
| CA2587671A1 (en) | 2006-05-18 |
| US20100324026A1 (en) | 2010-12-23 |
| IL183038A0 (en) | 2007-09-20 |
| CN101076525A (zh) | 2007-11-21 |
| NZ554937A (en) | 2011-01-28 |
| RU2007121682A (ru) | 2008-12-20 |
| WO2006051477A2 (en) | 2006-05-18 |
| ZA200703712B (en) | 2010-04-28 |
| TW200615273A (en) | 2006-05-16 |
| WO2006051477A3 (en) | 2006-08-03 |
| US8163730B2 (en) | 2012-04-24 |
| MX2007005470A (es) | 2007-07-10 |
| EP1812419A2 (en) | 2007-08-01 |
| AU2005303410A1 (en) | 2006-05-18 |
| JP2008519824A (ja) | 2008-06-12 |
| US20100305094A1 (en) | 2010-12-02 |
| IL210036A0 (en) | 2011-02-28 |
| KR20070106981A (ko) | 2007-11-06 |
| AR056861A1 (es) | 2007-10-31 |
| US7964631B2 (en) | 2011-06-21 |
| US20070299050A1 (en) | 2007-12-27 |
| CN101076525B (zh) | 2011-07-27 |
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