ZA200608992B - Antiviral agents - Google Patents
Antiviral agents Download PDFInfo
- Publication number
- ZA200608992B ZA200608992B ZA200608992A ZA200608992A ZA200608992B ZA 200608992 B ZA200608992 B ZA 200608992B ZA 200608992 A ZA200608992 A ZA 200608992A ZA 200608992 A ZA200608992 A ZA 200608992A ZA 200608992 B ZA200608992 B ZA 200608992B
- Authority
- ZA
- South Africa
- Prior art keywords
- dimethyl
- dione
- naphtho
- pyran
- independently selected
- Prior art date
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- 239000003443 antiviral agent Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 73
- 229910052799 carbon Inorganic materials 0.000 claims description 55
- 125000003118 aryl group Chemical group 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 27
- -1 Cs.scycloalkyl Chemical group 0.000 claims description 20
- 229940002612 prodrug Drugs 0.000 claims description 13
- 239000000651 prodrug Substances 0.000 claims description 13
- 239000003814 drug Substances 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- 229920006395 saturated elastomer Polymers 0.000 claims description 12
- 125000000539 amino acid group Chemical group 0.000 claims description 11
- 241000700721 Hepatitis B virus Species 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 229940124597 therapeutic agent Drugs 0.000 claims description 9
- 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 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- 239000011734 sodium Substances 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 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 description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 25
- 125000002837 carbocyclic group Chemical group 0.000 claims 8
- 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 5
- 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 5
- 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 4
- 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
- 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 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
- 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 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
- 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 1
- 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 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
- 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
- 239000011575 calcium Substances 0.000 description 13
- 125000005843 halogen group Chemical group 0.000 description 12
- 125000001424 substituent group Chemical group 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 11
- 235000001014 amino acid Nutrition 0.000 description 9
- 150000001413 amino acids Chemical group 0.000 description 9
- 230000037396 body weight Effects 0.000 description 9
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 7
- 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 6
- 239000002253 acid Substances 0.000 description 6
- 230000000840 anti-viral effect Effects 0.000 description 6
- 125000000623 heterocyclic group Chemical group 0.000 description 6
- KDKYADYSIPSCCQ-UHFFFAOYSA-N but-1-yne Chemical class CCC#C KDKYADYSIPSCCQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- 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
- WULRWFUSCFAPSR-UHFFFAOYSA-N benzo[f]chromene-1,2-dione Chemical group C1=CC=CC2=C(C(C(=O)CO3)=O)C3=CC=C21 WULRWFUSCFAPSR-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 125000001183 hydrocarbyl group Chemical group 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical class C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- XQSPYNMVSIKCOC-NTSWFWBYSA-N Emtricitabine Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1O[C@@H](CO)SC1 XQSPYNMVSIKCOC-NTSWFWBYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- 229960000366 emtricitabine Drugs 0.000 description 3
- 238000006735 epoxidation reaction Methods 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229960001627 lamivudine Drugs 0.000 description 3
- JTEGQNOMFQHVDC-NKWVEPMBSA-N lamivudine Chemical compound O=C1N=C(N)C=CN1[C@H]1O[C@@H](CO)SC1 JTEGQNOMFQHVDC-NKWVEPMBSA-N 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RTJUXLYUUDBAJN-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-3h-purin-6-one Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@H]1C[C@H](F)[C@@H](CO)O1 RTJUXLYUUDBAJN-KVQBGUIXSA-N 0.000 description 2
- DFVFTMTWCUHJBL-UHFFFAOYSA-N 4-azaniumyl-3-hydroxy-6-methylheptanoate Chemical compound CC(C)CC(N)C(O)CC(O)=O DFVFTMTWCUHJBL-UHFFFAOYSA-N 0.000 description 2
- JXQUAHHUSMJUFV-HZPZRMRQSA-N 9-[2-[[(2r,4s)-4-(3-chlorophenyl)-2-oxo-1,3,2$l^{5}-dioxaphosphinan-2-yl]methoxy]ethyl]purin-6-amine;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1([C@@H]2CCO[P@](O2)(=O)COCCN2C=3N=CN=C(C=3N=C2)N)=CC=CC(Cl)=C1 JXQUAHHUSMJUFV-HZPZRMRQSA-N 0.000 description 2
- VDBGPMJFHCJMOL-UHFFFAOYSA-N 9-[2-[bis(2,2,2-trifluoroethoxy)phosphorylmethoxy]ethyl]-6-(4-methoxyphenyl)sulfanylpurin-2-amine Chemical compound C1=CC(OC)=CC=C1SC1=NC(N)=NC2=C1N=CN2CCOCP(=O)(OCC(F)(F)F)OCC(F)(F)F VDBGPMJFHCJMOL-UHFFFAOYSA-N 0.000 description 2
- 108010078233 Thymalfasin Proteins 0.000 description 2
- 102400000800 Thymosin alpha-1 Human genes 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
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- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- WHBIGIKBNXZKFE-UHFFFAOYSA-N delavirdine Chemical compound CC(C)NC1=CC=CN=C1N1CCN(C(=O)C=2NC3=CC=C(NS(C)(=O)=O)C=C3C=2)CC1 WHBIGIKBNXZKFE-UHFFFAOYSA-N 0.000 description 2
- 238000001212 derivatisation Methods 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 2
- 239000002955 immunomodulating agent Substances 0.000 description 2
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- 230000003308 immunostimulating effect Effects 0.000 description 2
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 2
- NQDJXKOVJZTUJA-UHFFFAOYSA-N nevirapine Chemical compound C12=NC=CC=C2C(=O)NC=2C(C)=CC=NC=2N1C1CC1 NQDJXKOVJZTUJA-UHFFFAOYSA-N 0.000 description 2
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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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
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- 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
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- A—HUMAN NECESSITIES
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- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
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- 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 (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2004901755A AU2004901755A0 (en) | 2004-03-31 | Antiviral agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200608992B true ZA200608992B (en) | 2008-05-28 |
Family
ID=35063698
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200608992A ZA200608992B (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 |
|---|---|---|---|---|
| CA2761279A1 (en) * | 2009-05-20 | 2010-11-25 | 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 |
|---|---|---|---|---|
| AU8132094A (en) * | 1994-04-29 | 1995-11-29 | Biotech Research Laboratories | Khellactone derivatives and related compounds, process for their preparation and their use as antiviral and immunostimulating agents |
-
2005
- 2005-03-31 EP EP05714322A patent/EP1737836A1/en not_active Withdrawn
- 2005-03-31 WO PCT/AU2005/000453 patent/WO2005095376A1/en active Application Filing
- 2005-03-31 JP JP2007505333A patent/JP2007530600A/ja active Pending
- 2005-03-31 CN CNA2005800176510A patent/CN101018775A/zh active Pending
- 2005-03-31 ZA ZA200608992A patent/ZA200608992B/en unknown
- 2005-03-31 MX MXPA06011205A patent/MXPA06011205A/es not_active Application Discontinuation
- 2005-03-31 CA CA002561896A patent/CA2561896A1/en not_active Abandoned
- 2005-03-31 KR KR1020067022683A patent/KR20070009655A/ko not_active Application Discontinuation
- 2005-03-31 BR BRPI0509533-6A patent/BRPI0509533A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| KR20070009655A (ko) | 2007-01-18 |
| WO2005095376A1 (en) | 2005-10-13 |
| CN101018775A (zh) | 2007-08-15 |
| BRPI0509533A (pt) | 2007-09-18 |
| JP2007530600A (ja) | 2007-11-01 |
| EP1737836A1 (en) | 2007-01-03 |
| MXPA06011205A (es) | 2007-07-19 |
| CA2561896A1 (en) | 2005-10-13 |
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