CA2740193A1 - Anti-viral compounds - Google Patents
Anti-viral compounds Download PDFInfo
- Publication number
- CA2740193A1 CA2740193A1 CA2740193A CA2740193A CA2740193A1 CA 2740193 A1 CA2740193 A1 CA 2740193A1 CA 2740193 A CA2740193 A CA 2740193A CA 2740193 A CA2740193 A CA 2740193A CA 2740193 A1 CA2740193 A1 CA 2740193A1
- Authority
- CA
- Canada
- Prior art keywords
- optionally substituted
- compound
- occurrence
- c6alkyl
- halogen
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 168
- 230000000840 anti-viral effect Effects 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 35
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 12
- 208000015181 infectious disease Diseases 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 148
- -1 hydroxy, mercapto, amino, carboxy Chemical group 0.000 claims description 118
- 229910052739 hydrogen Inorganic materials 0.000 claims description 87
- 239000001257 hydrogen Substances 0.000 claims description 85
- 150000003839 salts Chemical class 0.000 claims description 85
- 229910052736 halogen Inorganic materials 0.000 claims description 76
- 150000002367 halogens Chemical class 0.000 claims description 72
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 72
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 70
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 70
- 229910019142 PO4 Inorganic materials 0.000 claims description 69
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 69
- 239000010452 phosphate Substances 0.000 claims description 69
- 125000004043 oxo group Chemical group O=* 0.000 claims description 68
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 68
- 125000001424 substituent group Chemical group 0.000 claims description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 52
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 51
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 32
- 125000004429 atom Chemical group 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 241000700605 Viruses Species 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 3
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 3
- 230000029812 viral genome replication Effects 0.000 claims description 2
- 239000000203 mixture Substances 0.000 abstract description 38
- 230000010076 replication Effects 0.000 abstract description 14
- 241000711549 Hepacivirus C Species 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
- 239000000047 product Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 31
- 239000000243 solution Substances 0.000 description 27
- 239000000651 prodrug Substances 0.000 description 26
- 229940002612 prodrug Drugs 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000012453 solvate Substances 0.000 description 21
- 239000007787 solid Substances 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 17
- 229910001868 water Inorganic materials 0.000 description 17
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- 239000002904 solvent Substances 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 239000003112 inhibitor Substances 0.000 description 14
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- 230000008878 coupling Effects 0.000 description 12
- 238000010168 coupling process Methods 0.000 description 12
- 238000005859 coupling reaction Methods 0.000 description 12
- 239000013078 crystal Substances 0.000 description 11
- 239000003814 drug Substances 0.000 description 11
- 125000006413 ring segment Chemical group 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- 125000000335 thiazolyl group Chemical group 0.000 description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 150000001412 amines Chemical class 0.000 description 10
- 125000004452 carbocyclyl group Chemical group 0.000 description 10
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- 229910052717 sulfur Inorganic materials 0.000 description 10
- 125000001544 thienyl group Chemical group 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 9
- 230000000670 limiting effect Effects 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 8
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 8
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 8
- 125000002541 furyl group Chemical group 0.000 description 8
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 125000002883 imidazolyl group Chemical group 0.000 description 8
- 125000001041 indolyl group Chemical group 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 125000002098 pyridazinyl group Chemical group 0.000 description 8
- 125000004076 pyridyl group Chemical group 0.000 description 8
- 125000000714 pyrimidinyl group Chemical group 0.000 description 8
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 description 7
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 7
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 7
- 125000001624 naphthyl group Chemical group 0.000 description 7
- 125000002971 oxazolyl group Chemical group 0.000 description 7
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 7
- 125000003373 pyrazinyl group Chemical group 0.000 description 7
- 125000003226 pyrazolyl group Chemical group 0.000 description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 7
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 7
- 125000001425 triazolyl group Chemical group 0.000 description 7
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000012091 fetal bovine serum Substances 0.000 description 6
- 210000004185 liver Anatomy 0.000 description 6
- 230000002829 reductive effect Effects 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- 230000003612 virological effect Effects 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 239000007821 HATU Substances 0.000 description 5
- 239000003443 antiviral agent Substances 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000008280 blood Substances 0.000 description 5
- 210000004369 blood Anatomy 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 150000004820 halides Chemical class 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 150000007524 organic acids Chemical class 0.000 description 5
- 235000005985 organic acids Nutrition 0.000 description 5
- 125000006239 protecting group Chemical group 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 108020004684 Internal Ribosome Entry Sites Proteins 0.000 description 4
- 101800001014 Non-structural protein 5A Proteins 0.000 description 4
- 239000002259 anti human immunodeficiency virus agent Substances 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 125000003386 piperidinyl group Chemical group 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000012023 real time release testing Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- YQUCBFIQSJVCOR-JOCHJYFZSA-N (7r)-14-cyclohexyl-7-{[2-(dimethylamino)ethyl](methyl)amino}-7,8-dihydro-6h-indolo[1,2-e][1,5]benzoxazocine-11-carboxylic acid Chemical compound C([C@@H](CN1C2=CC(=CC=C22)C(O)=O)N(C)CCN(C)C)OC3=CC=CC=C3C1=C2C1CCCCC1 YQUCBFIQSJVCOR-JOCHJYFZSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 108091026890 Coding region Proteins 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 229940124683 HCV polymerase inhibitor Drugs 0.000 description 3
- 102100034349 Integrase Human genes 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
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- IWUCXVSUMQZMFG-AFCXAGJDSA-N Ribavirin Chemical compound N1=C(C(=O)N)N=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 IWUCXVSUMQZMFG-AFCXAGJDSA-N 0.000 description 3
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- 229940124411 anti-hiv antiviral agent Drugs 0.000 description 3
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- 125000004122 cyclic group Chemical group 0.000 description 3
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- FKRSSPOQAMALKA-CUPIEXAXSA-N daclatasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C1=NC(C=2C=CC(=CC=2)C=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@@H](NC(=O)OC)C(C)C)=CN1 FKRSSPOQAMALKA-CUPIEXAXSA-N 0.000 description 3
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- OUIJIAOVRCTYBT-VAASOWBASA-N 4-(4-aminophenyl)sulfanyl-n-[4-[2-[(2s)-1-[(2r)-2-(dimethylamino)-2-phenylacetyl]pyrrolidin-2-yl]-1h-imidazol-5-yl]phenyl]-3-[(7-propan-2-ylpyrido[2,3-d]pyrimidin-4-yl)amino]benzamide Chemical compound N=1C=NC2=NC(C(C)C)=CC=C2C=1NC1=CC(C(=O)NC=2C=CC(=CC=2)C=2N=C(NC=2)[C@H]2N(CCC2)C(=O)[C@H](N(C)C)C=2C=CC=CC=2)=CC=C1SC1=CC=C(N)C=C1 OUIJIAOVRCTYBT-VAASOWBASA-N 0.000 description 2
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- 101000914479 Homo sapiens CD81 antigen Proteins 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
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- 229960002555 zidovudine Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Virology (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- Gastroenterology & Hepatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Peptides Or Proteins (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14026208P | 2008-12-23 | 2008-12-23 | |
| US61/140,262 | 2008-12-23 | ||
| PCT/US2009/069177 WO2010075376A2 (en) | 2008-12-23 | 2009-12-22 | Anti-viral compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2740193A1 true CA2740193A1 (en) | 2010-07-01 |
Family
ID=42169497
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2740193A Abandoned CA2740193A1 (en) | 2008-12-23 | 2009-12-22 | Anti-viral compounds |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US8541424B2 (enExample) |
| EP (1) | EP2367824B1 (enExample) |
| JP (1) | JP2012513409A (enExample) |
| CN (1) | CN102264737A (enExample) |
| CA (1) | CA2740193A1 (enExample) |
| ES (1) | ES2567047T3 (enExample) |
| MX (1) | MX2011006332A (enExample) |
| RU (1) | RU2505540C2 (enExample) |
| SG (1) | SG172352A1 (enExample) |
| WO (1) | WO2010075376A2 (enExample) |
| ZA (1) | ZA201105355B (enExample) |
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| CN102264737A (zh) | 2011-11-30 |
| US8541424B2 (en) | 2013-09-24 |
| US20100168138A1 (en) | 2010-07-01 |
| RU2505540C2 (ru) | 2014-01-27 |
| ES2567047T3 (es) | 2016-04-19 |
| US20140213601A1 (en) | 2014-07-31 |
| WO2010075376A2 (en) | 2010-07-01 |
| HK1159619A1 (zh) | 2012-08-03 |
| MX2011006332A (es) | 2011-06-27 |
| WO2010075376A3 (en) | 2010-09-30 |
| JP2012513409A (ja) | 2012-06-14 |
| ZA201105355B (en) | 2012-03-28 |
| US9163017B2 (en) | 2015-10-20 |
| EP2367824B1 (en) | 2016-03-23 |
| SG172352A1 (en) | 2011-07-28 |
| EP2367824A2 (en) | 2011-09-28 |
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