CN102382086A - 用于制备苯并呋喃类化合物的方法 - Google Patents
用于制备苯并呋喃类化合物的方法 Download PDFInfo
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- CN102382086A CN102382086A CN2011102205750A CN201110220575A CN102382086A CN 102382086 A CN102382086 A CN 102382086A CN 2011102205750 A CN2011102205750 A CN 2011102205750A CN 201110220575 A CN201110220575 A CN 201110220575A CN 102382086 A CN102382086 A CN 102382086A
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- ZJZKLBXEGZKOBW-UHFFFAOYSA-N (2-butyl-5-nitro-1-benzofuran-3-yl)-(4-hydroxyphenyl)methanone Chemical compound CCCCC=1OC2=CC=C([N+]([O-])=O)C=C2C=1C(=O)C1=CC=C(O)C=C1 ZJZKLBXEGZKOBW-UHFFFAOYSA-N 0.000 claims description 17
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
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- 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 description 10
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
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- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical group Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 description 6
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- OOHKBWPOLBTKMR-UHFFFAOYSA-N o-(4-nitrophenyl)hydroxylamine Chemical compound NOC1=CC=C([N+]([O-])=O)C=C1 OOHKBWPOLBTKMR-UHFFFAOYSA-N 0.000 description 6
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 3
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- DFGAKBLRAXKOOE-UHFFFAOYSA-N (1-amino-2-methylpropan-2-yl) carbamate Chemical group NCC(C)(C)OC(N)=O DFGAKBLRAXKOOE-UHFFFAOYSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- AQDRSCNQICSNAG-UHFFFAOYSA-N 1-benzofuran-3-yl-(4-methoxyphenyl)methanone Chemical class C1=CC(OC)=CC=C1C(=O)C1=COC2=CC=CC=C12 AQDRSCNQICSNAG-UHFFFAOYSA-N 0.000 description 1
- JBAITADHMBPOQQ-UHFFFAOYSA-N 2-(1h-benzimidazol-2-yl)-1,3-thiazole Chemical group C1=CSC(C=2NC3=CC=CC=C3N=2)=N1 JBAITADHMBPOQQ-UHFFFAOYSA-N 0.000 description 1
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 1
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- 239000001116 FEMA 4028 Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
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- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
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- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 238000005815 base catalysis Methods 0.000 description 1
- 229910052728 basic metal Inorganic materials 0.000 description 1
- 150000003818 basic metals Chemical class 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 1
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 1
- 229960004853 betadex Drugs 0.000 description 1
- 230000035587 bioadhesion Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
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- 230000002939 deleterious effect Effects 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
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- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- NALBLJLOBICXRH-UHFFFAOYSA-N dinitrogen monohydride Chemical compound N=[N] NALBLJLOBICXRH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- WDZAKURDTBXLAQ-UHFFFAOYSA-N ethyl n-(4-nitrophenoxy)ethanimidate Chemical compound CCOC(C)=NOC1=CC=C([N+]([O-])=O)C=C1 WDZAKURDTBXLAQ-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
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- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
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- 125000002883 imidazolyl group Chemical group 0.000 description 1
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- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
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- 229960003511 macrogol Drugs 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 description 1
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
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- 239000007935 oral tablet Substances 0.000 description 1
- 229940096978 oral tablet Drugs 0.000 description 1
- 125000001979 organolithium group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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- 238000012856 packing Methods 0.000 description 1
- 125000005936 piperidyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
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- 238000005730 ring rearrangement reaction Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 230000011218 segmentation Effects 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
- 238000000935 solvent evaporation Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 208000037816 tissue injury Diseases 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C239/00—Compounds containing nitrogen-to-halogen bonds; Hydroxylamino compounds or ethers or esters thereof
- C07C239/08—Hydroxylamino compounds or their ethers or esters
- C07C239/20—Hydroxylamino compounds or their ethers or esters having oxygen atoms of hydroxylamino groups etherified
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/825—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups all hydroxy groups bound to the ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
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|---|---|---|---|
| GB0719180.2 | 2007-10-02 | ||
| GBGB0719180.2A GB0719180D0 (en) | 2007-10-02 | 2007-10-02 | New process |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2008801163899A Division CN101861308B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
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| CN102382086A true CN102382086A (zh) | 2012-03-21 |
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| CN2008801163899A Expired - Fee Related CN101861308B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN201310195267.6A Expired - Fee Related CN103342633B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN2011102205750A Pending CN102382086A (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
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| CN2008801163899A Expired - Fee Related CN101861308B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
| CN201310195267.6A Expired - Fee Related CN103342633B (zh) | 2007-10-02 | 2008-10-02 | 用于制备苯并呋喃类化合物的方法 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US8519165B2 (enExample) |
| EP (3) | EP2200993B1 (enExample) |
| JP (2) | JP5577252B2 (enExample) |
| CN (3) | CN101861308B (enExample) |
| BR (1) | BRPI0817423A2 (enExample) |
| ES (3) | ES2559939T3 (enExample) |
| GB (1) | GB0719180D0 (enExample) |
| PL (3) | PL2388256T3 (enExample) |
| WO (1) | WO2009044143A2 (enExample) |
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| GB0719180D0 (en) | 2007-10-02 | 2007-11-14 | Cambrex Karlskoga Ab | New process |
| EP3195862A1 (en) | 2008-04-17 | 2017-07-26 | Sanofi | Use of dronedarone for the preparation of a medicament for use in the prevention of cardiovascular hospitalization or in the prevention of atrial fibrillation |
| EP2356100A1 (en) * | 2008-10-02 | 2011-08-17 | Cambrex Karlskoga AB | New process for preparing diketones and medicaments |
| CN102171199A (zh) * | 2008-10-10 | 2011-08-31 | 隆萨有限公司 | 制备2-烷基-3-芳酰基-5-硝基-苯并呋喃类的方法 |
| US8652785B2 (en) | 2008-12-04 | 2014-02-18 | Sanofi | Method of screening a modulator of endothelial NO synthase comprising the use of heme binding protein 1 |
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| FR2957079B1 (fr) | 2010-03-02 | 2012-07-27 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
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| HUP1000330A2 (en) | 2010-06-18 | 2011-12-28 | Sanofi Sa | Process for the preparation of dronedarone and the novel intermediates |
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| US8602215B2 (en) | 2010-06-30 | 2013-12-10 | Sanofi | Methods for reducing the risk of an adverse dronedarone/beta-blockers interaction in a patient suffering from atrial fibrillation |
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| FR2963006B1 (fr) * | 2010-07-21 | 2013-03-15 | Sanofi Aventis | Procede de preparation de derives de nitro-benzofurane |
| EP2452938A1 (en) | 2010-11-12 | 2012-05-16 | LEK Pharmaceuticals d.d. | Process for the preparation of 3-aroyl-5-aminobenzofuran derivatives |
| CN102070581B (zh) * | 2011-01-19 | 2015-11-25 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-氨基苯并呋喃的制备 |
| CN102070577B (zh) * | 2011-01-19 | 2016-03-09 | 上海医药工业研究院 | 2-正丁基-3-(4-取代丙氧基苯甲酰基)-5-取代氨基苯并呋喃及其应用 |
| CN102070578B (zh) * | 2011-01-19 | 2015-10-14 | 上海医药工业研究院 | 2-正丁基-3-(4-(3-二正丁基氨基丙氧基)苯甲酰基)-5-烷酰基氨基苯并呋喃的制备方法 |
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| FR2973027A1 (fr) * | 2011-03-24 | 2012-09-28 | Sanofi Aventis | Procede de synthese de derives de cetobenzofurane |
| HUP1100167A2 (en) * | 2011-03-29 | 2012-11-28 | Sanofi Sa | Process for preparation of dronedarone by mesylation |
| HUP1100165A2 (en) | 2011-03-29 | 2012-12-28 | Sanofi Sa | Process for preparation of dronedarone by n-butylation |
| WO2013014480A1 (en) * | 2011-07-26 | 2013-01-31 | Sanofi | Process for preparation of dronedarone using amide intermediary compound |
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2007
- 2007-10-02 GB GBGB0719180.2A patent/GB0719180D0/en not_active Ceased
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2008
- 2008-10-02 BR BRPI0817423-7A patent/BRPI0817423A2/pt not_active IP Right Cessation
- 2008-10-02 PL PL11075168T patent/PL2388256T3/pl unknown
- 2008-10-02 PL PL13167925.0T patent/PL2636670T3/pl unknown
- 2008-10-02 EP EP08806486A patent/EP2200993B1/en not_active Not-in-force
- 2008-10-02 WO PCT/GB2008/003341 patent/WO2009044143A2/en not_active Ceased
- 2008-10-02 EP EP13167925.0A patent/EP2636670B1/en not_active Not-in-force
- 2008-10-02 ES ES11075168.2T patent/ES2559939T3/es active Active
- 2008-10-02 CN CN2008801163899A patent/CN101861308B/zh not_active Expired - Fee Related
- 2008-10-02 ES ES13167925.0T patent/ES2589011T3/es active Active
- 2008-10-02 CN CN201310195267.6A patent/CN103342633B/zh not_active Expired - Fee Related
- 2008-10-02 ES ES08806486T patent/ES2395174T3/es active Active
- 2008-10-02 CN CN2011102205750A patent/CN102382086A/zh active Pending
- 2008-10-02 EP EP11075168.2A patent/EP2388256B1/en not_active Not-in-force
- 2008-10-02 PL PL08806486T patent/PL2200993T3/pl unknown
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- 2008-10-02 US US12/681,299 patent/US8519165B2/en not_active Expired - Fee Related
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|---|---|
| PL2388256T3 (pl) | 2016-06-30 |
| EP2388256A3 (en) | 2012-03-21 |
| WO2009044143A3 (en) | 2009-06-25 |
| JP2014208660A (ja) | 2014-11-06 |
| ES2395174T3 (es) | 2013-02-08 |
| EP2388256A1 (en) | 2011-11-23 |
| HK1145684A1 (en) | 2011-04-29 |
| EP2636670B1 (en) | 2016-06-01 |
| HK1164303A1 (en) | 2012-09-21 |
| JP5943965B2 (ja) | 2016-07-05 |
| ES2589011T3 (es) | 2016-11-08 |
| US8779201B2 (en) | 2014-07-15 |
| CN103342633B (zh) | 2016-05-04 |
| HK1185611A1 (en) | 2014-02-21 |
| CN101861308A (zh) | 2010-10-13 |
| EP2200993A2 (en) | 2010-06-30 |
| CN101861308B (zh) | 2013-06-19 |
| ES2559939T3 (es) | 2016-02-16 |
| WO2009044143A2 (en) | 2009-04-09 |
| BRPI0817423A2 (pt) | 2015-06-16 |
| US8519165B2 (en) | 2013-08-27 |
| JP2010540608A (ja) | 2010-12-24 |
| US20130338398A1 (en) | 2013-12-19 |
| WO2009044143A4 (en) | 2009-09-11 |
| PL2636670T3 (pl) | 2016-12-30 |
| EP2200993B1 (en) | 2012-08-29 |
| CN103342633A (zh) | 2013-10-09 |
| EP2388256B1 (en) | 2015-11-25 |
| GB0719180D0 (en) | 2007-11-14 |
| JP5577252B2 (ja) | 2014-08-20 |
| PL2200993T3 (pl) | 2013-01-31 |
| EP2636670A1 (en) | 2013-09-11 |
| US20100292319A1 (en) | 2010-11-18 |
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