CA2561896A1 - Antiviral agents - Google Patents
Antiviral agents Download PDFInfo
- Publication number
- CA2561896A1 CA2561896A1 CA002561896A CA2561896A CA2561896A1 CA 2561896 A1 CA2561896 A1 CA 2561896A1 CA 002561896 A CA002561896 A CA 002561896A CA 2561896 A CA2561896 A CA 2561896A CA 2561896 A1 CA2561896 A1 CA 2561896A1
- Authority
- CA
- Canada
- Prior art keywords
- 6alkyl
- dimethyl
- dione
- pyran
- 6alkynyl
- 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
- 239000003443 antiviral agent Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- 238000000034 method Methods 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 238000011282 treatment Methods 0.000 claims abstract description 12
- 229940002612 prodrug Drugs 0.000 claims abstract description 8
- 239000000651 prodrug Substances 0.000 claims abstract description 8
- 238000011321 prophylaxis Methods 0.000 claims abstract description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 3
- 125000003118 aryl group Chemical group 0.000 claims description 39
- 229910052799 carbon Inorganic materials 0.000 claims description 30
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
- 125000000539 amino acid group Chemical group 0.000 claims description 7
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 208000006454 hepatitis Diseases 0.000 claims description 5
- 231100000283 hepatitis Toxicity 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 241000701076 Macacine alphaherpesvirus 1 Species 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 44
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 40
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 39
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 38
- 125000001475 halogen functional group Chemical group 0.000 claims 16
- HTZRTRPVVFIREC-UHFFFAOYSA-N CC1(C)Oc2ccc3C(=O)C(O)=C(Br)C(=O)c3c2C=C1 Chemical compound CC1(C)Oc2ccc3C(=O)C(O)=C(Br)C(=O)c3c2C=C1 HTZRTRPVVFIREC-UHFFFAOYSA-N 0.000 claims 6
- WNQNLZFNNHMNKX-UHFFFAOYSA-N 10-hydroxy-3,3-dimethylbenzo[f]chromene-7,8-dione Chemical compound O=C1C(=O)C=C(O)C2=C(C=CC(C)(C)O3)C3=CC=C21 WNQNLZFNNHMNKX-UHFFFAOYSA-N 0.000 claims 4
- XKQSAMDDFUTTAF-UHFFFAOYSA-N (9-bromo-3,3-dimethyl-7,10-dioxo-1,2-dihydrobenzo[f]chromen-8-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=C(Br)C(=O)C2=C(CCC(C)(C)O3)C3=CC=C2C1=O XKQSAMDDFUTTAF-UHFFFAOYSA-N 0.000 claims 3
- RBIHDDLENIMIRM-UHFFFAOYSA-N (9-bromo-3,3-dimethyl-7,10-dioxobenzo[f]chromen-8-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC(C1=O)=C(Br)C(=O)C2=C1C=CC1=C2C=CC(C)(C)O1 RBIHDDLENIMIRM-UHFFFAOYSA-N 0.000 claims 3
- LEYKGBIFLZXMGU-UHFFFAOYSA-N CC1(C)CCc2c(O1)ccc1C(=O)C(O)=CC(=O)c21 Chemical compound CC1(C)CCc2c(O1)ccc1C(=O)C(O)=CC(=O)c21 LEYKGBIFLZXMGU-UHFFFAOYSA-N 0.000 claims 3
- WPXIHSYZOAWPCN-UHFFFAOYSA-N (7,8-diacetyloxy-3,3-dimethylbenzo[f]chromen-10-yl) acetate Chemical compound C1=CC(C)(C)OC2=C1C1=C(OC(C)=O)C=C(OC(=O)C)C(OC(C)=O)=C1C=C2 WPXIHSYZOAWPCN-UHFFFAOYSA-N 0.000 claims 2
- DGJUXQHBMRKPAW-UHFFFAOYSA-N (8-bromo-3,3-dimethyl-7,10-dioxobenzo[f]chromen-9-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=C(Br)C(=O)C2=CC=C(OC(C)(C)C=C3)C3=C2C1=O DGJUXQHBMRKPAW-UHFFFAOYSA-N 0.000 claims 2
- GOLKLHZWYPWWIQ-UHFFFAOYSA-N CC1(C)Oc2ccc3C(=O)C(O)=C(Br)C(=O)c3c2C(O)C1Br Chemical compound CC1(C)Oc2ccc3C(=O)C(O)=C(Br)C(=O)c3c2C(O)C1Br GOLKLHZWYPWWIQ-UHFFFAOYSA-N 0.000 claims 2
- FUELOUDOBJXBIW-UHFFFAOYSA-M sodium;3,3-dimethyl-7,10-dioxobenzo[f]chromen-8-olate Chemical compound [Na+].O=C1C([O-])=CC(=O)C2=C(C=CC(C)(C)O3)C3=CC=C21 FUELOUDOBJXBIW-UHFFFAOYSA-M 0.000 claims 2
- GQIKDXGNPODHIA-UHFFFAOYSA-N (3,3-dimethyl-7,10-dioxobenzo[f]chromen-8-yl) acetate Chemical compound O1C(C)(C)C=CC2=C1C=CC1=C2C(=O)C=C(OC(=O)C)C1=O GQIKDXGNPODHIA-UHFFFAOYSA-N 0.000 claims 1
- ZHNSKQWXBCTNON-UHFFFAOYSA-N (8-bromo-3,3-dimethyl-7,10-dioxo-1,2-dihydrobenzo[f]chromen-9-yl) 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OC1=C(Br)C(=O)C2=CC=C(OC(C)(C)CC3)C3=C2C1=O ZHNSKQWXBCTNON-UHFFFAOYSA-N 0.000 claims 1
- MOLZRLBYUWSXBQ-UHFFFAOYSA-N 8,9-dichloro-3,3-dimethyl-1,2-dihydrobenzo[f]chromene-7,10-dione Chemical compound O=C1C(Cl)=C(Cl)C(=O)C2=C1C=CC1=C2CCC(C)(C)O1 MOLZRLBYUWSXBQ-UHFFFAOYSA-N 0.000 claims 1
- PYSZMCLQABISDZ-UHFFFAOYSA-N CC1(C)CCc2c(O1)ccc1C(=O)C(O)=C(Br)C(=O)c21 Chemical compound CC1(C)CCc2c(O1)ccc1C(=O)C(O)=C(Br)C(=O)c21 PYSZMCLQABISDZ-UHFFFAOYSA-N 0.000 claims 1
- DNLCMBCMBNMRJB-UHFFFAOYSA-N CC1(Oc2ccc3C(=O)C(O)=CC(=O)c3c2C=C1)c1ccccc1 Chemical compound CC1(Oc2ccc3C(=O)C(O)=CC(=O)c3c2C=C1)c1ccccc1 DNLCMBCMBNMRJB-UHFFFAOYSA-N 0.000 claims 1
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims 1
- SJGULVFMZKDDDB-UHFFFAOYSA-N OC1=CC(=O)c2c(ccc3OC(C=Cc23)(c2ccccc2)c2ccccc2)C1=O Chemical compound OC1=CC(=O)c2c(ccc3OC(C=Cc23)(c2ccccc2)c2ccccc2)C1=O SJGULVFMZKDDDB-UHFFFAOYSA-N 0.000 claims 1
- WIMISEOIQWRBER-UHFFFAOYSA-M OC=1C(C2=C(C=3C=CC(OC3C=C2)(C2=CC=CC=C2)C)C(C1)=O)=O.CC1(OC=2C=CC3=C(C2C=C1)C(=CC(C3=O)=O)[O-])C.[Na+] Chemical compound OC=1C(C2=C(C=3C=CC(OC3C=C2)(C2=CC=CC=C2)C)C(C1)=O)=O.CC1(OC=2C=CC3=C(C2C=C1)C(=CC(C3=O)=O)[O-])C.[Na+] WIMISEOIQWRBER-UHFFFAOYSA-M 0.000 claims 1
- GNBGQMHHLQEXBF-UHFFFAOYSA-M sodium;3,3-dimethyl-7,8-dioxobenzo[f]chromen-10-olate Chemical compound [Na+].O=C1C(=O)C=C([O-])C2=C(C=CC(C)(C)O3)C3=CC=C21 GNBGQMHHLQEXBF-UHFFFAOYSA-M 0.000 claims 1
- 241000700721 Hepatitis B virus Species 0.000 abstract description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 239000000203 mixture Substances 0.000 description 52
- 239000000243 solution Substances 0.000 description 42
- 125000000217 alkyl group Chemical group 0.000 description 33
- 239000007787 solid Substances 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- 229910052739 hydrogen Inorganic materials 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 22
- 239000002253 acid Substances 0.000 description 21
- 239000003795 chemical substances by application Substances 0.000 description 20
- -1 C~.~oycloalkyl Chemical group 0.000 description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 16
- 238000006243 chemical reaction Methods 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 239000004480 active ingredient Substances 0.000 description 13
- 230000000840 anti-viral effect Effects 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 125000000304 alkynyl group Chemical group 0.000 description 11
- 125000005843 halogen group Chemical group 0.000 description 11
- 150000001721 carbon Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001413 amino acids Chemical group 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 238000005481 NMR spectroscopy Methods 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000001301 oxygen Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 244000269722 Thea sinensis Species 0.000 description 7
- 230000037396 body weight Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 241000700605 Viruses Species 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 235000015424 sodium Nutrition 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- NQZPUYGKQPAUPO-UHFFFAOYSA-N 3h-benzo[f]chromen-1-ol Chemical compound C1=CC=CC2=C3C(O)=CCOC3=CC=C21 NQZPUYGKQPAUPO-UHFFFAOYSA-N 0.000 description 5
- 239000000969 carrier Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
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- 238000006722 reduction reaction Methods 0.000 description 5
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- 239000003826 tablet Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- VCMLCMCXCRBSQO-UHFFFAOYSA-N 3h-benzo[f]chromene Chemical compound C1=CC=CC2=C(C=CCO3)C3=CC=C21 VCMLCMCXCRBSQO-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/92—Naphthopyrans; Hydrogenated naphthopyrans
-
- 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
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Virology (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Communicable Diseases (AREA)
- Gastroenterology & Hepatology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyrane Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2004901755 | 2004-03-31 | ||
| AU2004901755A AU2004901755A0 (en) | 2004-03-31 | Antiviral agents | |
| PCT/AU2005/000453 WO2005095376A1 (en) | 2004-03-31 | 2005-03-31 | Antiviral agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2561896A1 true CA2561896A1 (en) | 2005-10-13 |
Family
ID=35063698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002561896A Abandoned CA2561896A1 (en) | 2004-03-31 | 2005-03-31 | Antiviral agents |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1737836A1 (es) |
| JP (1) | JP2007530600A (es) |
| KR (1) | KR20070009655A (es) |
| CN (1) | CN101018775A (es) |
| BR (1) | BRPI0509533A (es) |
| CA (1) | CA2561896A1 (es) |
| MX (1) | MXPA06011205A (es) |
| WO (1) | WO2005095376A1 (es) |
| ZA (1) | ZA200608992B (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2010251272A1 (en) * | 2009-05-20 | 2011-12-15 | F. Hoffmann-La Roche Ag | Heterocyclic antiviral compounds |
| CN106866609B (zh) * | 2017-02-08 | 2018-11-16 | 江西本草天工科技有限责任公司 | 小花清风藤中一种新化合物的制备方法及应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029920A1 (en) * | 1994-04-29 | 1995-11-09 | The University Of North Carolina At Chapel Hill | Khellactone derivatives and related compounds, process for their preparation and their use as antiviral and immunostimulating agents |
-
2005
- 2005-03-31 CA CA002561896A patent/CA2561896A1/en not_active Abandoned
- 2005-03-31 BR BRPI0509533-6A patent/BRPI0509533A/pt not_active IP Right Cessation
- 2005-03-31 JP JP2007505333A patent/JP2007530600A/ja active Pending
- 2005-03-31 KR KR1020067022683A patent/KR20070009655A/ko not_active Application Discontinuation
- 2005-03-31 WO PCT/AU2005/000453 patent/WO2005095376A1/en active Application Filing
- 2005-03-31 ZA ZA200608992A patent/ZA200608992B/en unknown
- 2005-03-31 EP EP05714322A patent/EP1737836A1/en not_active Withdrawn
- 2005-03-31 MX MXPA06011205A patent/MXPA06011205A/es not_active Application Discontinuation
- 2005-03-31 CN CNA2005800176510A patent/CN101018775A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| WO2005095376A1 (en) | 2005-10-13 |
| JP2007530600A (ja) | 2007-11-01 |
| BRPI0509533A (pt) | 2007-09-18 |
| KR20070009655A (ko) | 2007-01-18 |
| ZA200608992B (en) | 2008-05-28 |
| MXPA06011205A (es) | 2007-07-19 |
| EP1737836A1 (en) | 2007-01-03 |
| CN101018775A (zh) | 2007-08-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |