RU2009127095A - Новые оксадиазольные соединения - Google Patents
Новые оксадиазольные соединения Download PDFInfo
- Publication number
- RU2009127095A RU2009127095A RU2009127095/04A RU2009127095A RU2009127095A RU 2009127095 A RU2009127095 A RU 2009127095A RU 2009127095/04 A RU2009127095/04 A RU 2009127095/04A RU 2009127095 A RU2009127095 A RU 2009127095A RU 2009127095 A RU2009127095 A RU 2009127095A
- Authority
- RU
- Russia
- Prior art keywords
- optionally substituted
- alkyl
- compound
- cycloalkyl
- phenyl
- Prior art date
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- 150000004866 oxadiazoles Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 35
- -1 2,3-dihydroisoindolyl Chemical group 0.000 claims abstract 24
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 16
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 12
- 150000003839 salts Chemical class 0.000 claims abstract 12
- 239000012453 solvate Substances 0.000 claims abstract 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- 239000000651 prodrug Substances 0.000 claims abstract 10
- 229940002612 prodrug Drugs 0.000 claims abstract 10
- 239000002207 metabolite Substances 0.000 claims abstract 9
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 8
- 150000004677 hydrates Chemical class 0.000 claims abstract 7
- 125000001624 naphthyl group Chemical group 0.000 claims abstract 7
- 125000000842 isoxazolyl group Chemical group 0.000 claims abstract 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract 6
- 125000001544 thienyl group Chemical group 0.000 claims abstract 6
- 125000002541 furyl group Chemical group 0.000 claims abstract 5
- 125000001041 indolyl group Chemical group 0.000 claims abstract 5
- 125000002757 morpholinyl group Chemical group 0.000 claims abstract 5
- 125000003386 piperidinyl group Chemical group 0.000 claims abstract 5
- 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 claims abstract 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract 4
- 125000002883 imidazolyl group Chemical group 0.000 claims abstract 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 3
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract 3
- 125000005887 tetrahydrobenzofuranyl group Chemical group 0.000 claims abstract 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims abstract 3
- 125000000335 thiazolyl group Chemical group 0.000 claims abstract 3
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims abstract 2
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims abstract 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims abstract 2
- 201000009482 yaws Diseases 0.000 claims 19
- 206010003246 arthritis Diseases 0.000 claims 14
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 11
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 8
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004193 piperazinyl group Chemical group 0.000 claims 5
- 125000001424 substituent group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000000623 heterocyclic group Chemical group 0.000 claims 4
- 125000003107 substituted aryl group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000003944 tolyl group Chemical group 0.000 claims 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 2
- 230000001363 autoimmune Effects 0.000 claims 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 2
- 208000026278 immune system disease Diseases 0.000 claims 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical class C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000006399 methylpyrazinyl group Chemical group 0.000 claims 2
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- KZZHPWMVEVZEFG-UHFFFAOYSA-N tert-butyl n-phenylcarbamate Chemical compound CC(C)(C)OC(=O)NC1=CC=CC=C1 KZZHPWMVEVZEFG-UHFFFAOYSA-N 0.000 claims 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 1
- 125000006531 (C2-C5) alkyl group Chemical group 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- KVPBSBOTFRNKOM-UHFFFAOYSA-N 2h-cyclopenta[b]thiophene Chemical compound C1=CC2=CCSC2=C1 KVPBSBOTFRNKOM-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical class [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- 208000002310 Achlorhydria Diseases 0.000 claims 1
- 208000026872 Addison Disease Diseases 0.000 claims 1
- 206010001324 Adrenal atrophy Diseases 0.000 claims 1
- 208000003343 Antiphospholipid Syndrome Diseases 0.000 claims 1
- 206010003645 Atopy Diseases 0.000 claims 1
- 208000004300 Atrophic Gastritis Diseases 0.000 claims 1
- 208000031212 Autoimmune polyendocrinopathy Diseases 0.000 claims 1
- 208000008439 Biliary Liver Cirrhosis Diseases 0.000 claims 1
- 208000033222 Biliary cirrhosis primary Diseases 0.000 claims 1
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 206010008609 Cholangitis sclerosing Diseases 0.000 claims 1
- 206010008909 Chronic Hepatitis Diseases 0.000 claims 1
- 208000015943 Coeliac disease Diseases 0.000 claims 1
- 206010009900 Colitis ulcerative Diseases 0.000 claims 1
- 208000011231 Crohn disease Diseases 0.000 claims 1
- 208000014311 Cushing syndrome Diseases 0.000 claims 1
- 201000004624 Dermatitis Diseases 0.000 claims 1
- 208000036495 Gastritis atrophic Diseases 0.000 claims 1
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 1
- 208000003807 Graves Disease Diseases 0.000 claims 1
- 208000015023 Graves' disease Diseases 0.000 claims 1
- 208000030836 Hashimoto thyroiditis Diseases 0.000 claims 1
- 101000766253 Homo sapiens TLR4 interactor with leucine rich repeats Proteins 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010021245 Idiopathic thrombocytopenic purpura Diseases 0.000 claims 1
- 206010022489 Insulin Resistance Diseases 0.000 claims 1
- 201000010743 Lambert-Eaton myasthenic syndrome Diseases 0.000 claims 1
- 206010067737 Lupus hepatitis Diseases 0.000 claims 1
- 208000003250 Mixed connective tissue disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 201000011152 Pemphigus Diseases 0.000 claims 1
- 208000031845 Pernicious anaemia Diseases 0.000 claims 1
- 206010065159 Polychondritis Diseases 0.000 claims 1
- 208000012654 Primary biliary cholangitis Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000003782 Raynaud disease Diseases 0.000 claims 1
- 208000012322 Raynaud phenomenon Diseases 0.000 claims 1
- 208000033464 Reiter syndrome Diseases 0.000 claims 1
- 208000021386 Sjogren Syndrome Diseases 0.000 claims 1
- 102100026308 TLR4 interactor with leucine rich repeats Human genes 0.000 claims 1
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 1
- 206010046851 Uveitis Diseases 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- 125000004686 alkyl sulfanyl alkyl group Chemical group 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 230000007815 allergy Effects 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 125000002431 aminoalkoxy group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 1
- 201000003710 autoimmune thrombocytopenic purpura Diseases 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 208000015114 central nervous system disease Diseases 0.000 claims 1
- 208000016644 chronic atrophic gastritis Diseases 0.000 claims 1
- 208000025302 chronic primary adrenal insufficiency Diseases 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000005366 cycloalkylthio group Chemical group 0.000 claims 1
- 125000004663 dialkyl amino group Chemical group 0.000 claims 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 1
- 125000004473 dialkylaminocarbonyl group Chemical group 0.000 claims 1
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 208000006454 hepatitis Diseases 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims 1
- 206010025135 lupus erythematosus Diseases 0.000 claims 1
- 125000004312 morpholin-2-yl group Chemical group [H]N1C([H])([H])C([H])([H])OC([H])(*)C1([H])[H] 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- 201000006417 multiple sclerosis Diseases 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 201000009395 primary hyperaldosteronism Diseases 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 208000002574 reactive arthritis Diseases 0.000 claims 1
- 230000000306 recurrent effect Effects 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 125000004426 substituted alkynyl group Chemical group 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 230000002889 sympathetic effect Effects 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 229930192474 thiophene Natural products 0.000 claims 1
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 1
- 0 *Oc(ccc(-c1n[o]c(I*)n1)c1)c1Cl Chemical compound *Oc(ccc(-c1n[o]c(I*)n1)c1)c1Cl 0.000 description 1
- LMDJGVPLCKWXHO-UHFFFAOYSA-N CC(C)Oc(ccc(-c1n[o]c(-c2ccc(C(C)(C)NCCC(O)=O)cc2)n1)c1)c1Cl Chemical compound CC(C)Oc(ccc(-c1n[o]c(-c2ccc(C(C)(C)NCCC(O)=O)cc2)n1)c1)c1Cl LMDJGVPLCKWXHO-UHFFFAOYSA-N 0.000 description 1
- CWBUHAXVYQYCHL-UHFFFAOYSA-N CCCC(C)CNC(CC1)CCC1C(O)=O Chemical compound CCCC(C)CNC(CC1)CCC1C(O)=O CWBUHAXVYQYCHL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
- C07D271/07—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
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| MY149853A (en) | 2006-09-07 | 2013-10-31 | Actelion Pharmaceuticals Ltd | Pyridin-4-yl derivatives as immunomodulating agents |
| TWI408139B (zh) | 2006-09-07 | 2013-09-11 | Actelion Pharmaceuticals Ltd | 新穎噻吩衍生物 |
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| CA2689282A1 (en) | 2007-06-03 | 2008-12-11 | Vanderbilt University | Benzamide mglur5 positive allosteric modulators and methods of making and using same |
-
2007
- 2007-12-14 AU AU2007334436A patent/AU2007334436A1/en not_active Abandoned
- 2007-12-14 BR BRPI0720043-9A patent/BRPI0720043A2/pt not_active IP Right Cessation
- 2007-12-14 US US12/002,196 patent/US7834039B2/en active Active
- 2007-12-14 RU RU2009127095/04A patent/RU2009127095A/ru not_active Application Discontinuation
- 2007-12-14 SG SG2011094539A patent/SG177221A1/en unknown
- 2007-12-14 WO PCT/US2007/025602 patent/WO2008076356A1/en not_active Ceased
- 2007-12-14 MX MX2009006304A patent/MX2009006304A/es not_active Application Discontinuation
- 2007-12-14 NZ NZ577111A patent/NZ577111A/en not_active IP Right Cessation
- 2007-12-14 EP EP07867755A patent/EP2109364A4/en not_active Withdrawn
- 2007-12-14 CN CNA2007800463459A patent/CN101562977A/zh active Pending
- 2007-12-14 KR KR1020097014830A patent/KR20090095648A/ko not_active Withdrawn
- 2007-12-14 JP JP2009541394A patent/JP2010513283A/ja not_active Withdrawn
- 2007-12-14 CA CA002672616A patent/CA2672616A1/en not_active Abandoned
- 2007-12-17 TW TW096148339A patent/TW200840567A/zh unknown
-
2009
- 2009-05-27 ZA ZA200903693A patent/ZA200903693B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2109364A1 (en) | 2009-10-21 |
| ZA200903693B (en) | 2010-03-31 |
| MX2009006304A (es) | 2009-06-23 |
| JP2010513283A (ja) | 2010-04-30 |
| AU2007334436A1 (en) | 2008-06-26 |
| NZ577111A (en) | 2012-05-25 |
| CN101562977A (zh) | 2009-10-21 |
| CA2672616A1 (en) | 2008-06-26 |
| SG177221A1 (en) | 2012-01-30 |
| TW200840567A (en) | 2008-10-16 |
| BRPI0720043A2 (pt) | 2014-01-07 |
| US7834039B2 (en) | 2010-11-16 |
| EP2109364A4 (en) | 2010-04-14 |
| KR20090095648A (ko) | 2009-09-09 |
| US20080280876A1 (en) | 2008-11-13 |
| WO2008076356A1 (en) | 2008-06-26 |
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| FA94 | Acknowledgement of application withdrawn (non-payment of fees) |
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