ZA200308629B - Tricyclic dihydro-quinoline derivatives, method for preparing same and pharmaceutical compositions containing same. - Google Patents
Tricyclic dihydro-quinoline derivatives, method for preparing same and pharmaceutical compositions containing same. Download PDFInfo
- Publication number
- ZA200308629B ZA200308629B ZA200308629A ZA200308629A ZA200308629B ZA 200308629 B ZA200308629 B ZA 200308629B ZA 200308629 A ZA200308629 A ZA 200308629A ZA 200308629 A ZA200308629 A ZA 200308629A ZA 200308629 B ZA200308629 B ZA 200308629B
- Authority
- ZA
- South Africa
- Prior art keywords
- group
- branched
- linear
- formula
- alkyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 15
- 239000008194 pharmaceutical composition Substances 0.000 title description 5
- 125000005044 dihydroquinolinyl group Chemical class N1(CC=CC2=CC=CC=C12)* 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 52
- 125000003118 aryl group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 125000005842 heteroatom Chemical group 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 12
- 230000003287 optical effect Effects 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 10
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 125000006684 polyhaloalkyl group Polymers 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- SMCYFWGSCBFUCR-UHFFFAOYSA-N 6-methoxy-4-methyl-9-(3,4,5-trimethoxyphenyl)-3,9-dihydrofuro[3,4-b]quinoline-1-thione Chemical compound C1OC(=S)C2=C1N(C)C1=CC(OC)=CC=C1C2C1=CC(OC)=C(OC)C(OC)=C1 SMCYFWGSCBFUCR-UHFFFAOYSA-N 0.000 claims description 3
- FQOUCLOASADFCF-UHFFFAOYSA-N 8-methyl-8-(3,4,5-trimethoxyphenyl)-5,12,14-trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one Chemical compound COC1=C(OC)C(OC)=CC(C2(C)C3=CC=4OCOC=4C=C3NC3=C2C(OC3)=O)=C1 FQOUCLOASADFCF-UHFFFAOYSA-N 0.000 claims description 3
- UEZKFETUOHLWQF-UHFFFAOYSA-N COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3N(CC=3C=CC=CC=3)C3=C2C(OC3)=S)=C1 Chemical compound COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3N(CC=3C=CC=CC=3)C3=C2C(OC3)=S)=C1 UEZKFETUOHLWQF-UHFFFAOYSA-N 0.000 claims description 3
- -1 biphenylyl Chemical group 0.000 claims description 3
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 3
- OBLWAYYWPBCNCD-UHFFFAOYSA-N 4,4-dimethyl-8-(3,4,5-trimethoxyphenyl)-5,12,14-trioxa-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one Chemical compound COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3NC3=C2C(OC3(C)C)=O)=C1 OBLWAYYWPBCNCD-UHFFFAOYSA-N 0.000 claims description 2
- QNVUMKZGGZLVQG-UHFFFAOYSA-N 4,4-dimethyl-8-(3,4,5-trimethoxyphenyl)-5,12,14-trioxa-6lambda6-thia-2-azatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraene 6,6-dioxide Chemical compound COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3NC3=C2S(OC3(C)C)(=O)=O)=C1 QNVUMKZGGZLVQG-UHFFFAOYSA-N 0.000 claims description 2
- DLXXHONHNKEVIU-UHFFFAOYSA-N C1OC(=O)C2=C1NC1=CC=3OCOC=3C=C1C2(C)C1=CC=CC=C1 Chemical compound C1OC(=O)C2=C1NC1=CC=3OCOC=3C=C1C2(C)C1=CC=CC=C1 DLXXHONHNKEVIU-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005864 Sulphur Substances 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- GETMSPZIIJLCJJ-UHFFFAOYSA-N chembl486110 Chemical compound COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3NC3=C2C(NC3)=O)=C1 GETMSPZIIJLCJJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 229920006395 saturated elastomer Chemical group 0.000 claims description 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- XGNXYCFREOZBOL-UHFFFAOYSA-N 1,3-benzodioxol-5-amine Chemical compound NC1=CC=C2OCOC2=C1 XGNXYCFREOZBOL-UHFFFAOYSA-N 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
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- PGRHXDWITVMQBC-UHFFFAOYSA-N dehydroacetic acid Natural products CC(=O)C1C(=O)OC(C)=CC1=O PGRHXDWITVMQBC-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- PEQJBOMPGWYIRO-UHFFFAOYSA-N n-ethyl-3,4-dimethoxyaniline Chemical compound CCNC1=CC=C(OC)C(OC)=C1 PEQJBOMPGWYIRO-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000004452 microanalysis Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
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- 239000004480 active ingredient Substances 0.000 description 2
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- 231100000135 cytotoxicity Toxicity 0.000 description 2
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- 238000000338 in vitro Methods 0.000 description 2
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- OFVNZOJVKWKSPT-UHFFFAOYSA-N n-benzyl-1,3-benzodioxol-5-amine Chemical compound C=1C=C2OCOC2=CC=1NCC1=CC=CC=C1 OFVNZOJVKWKSPT-UHFFFAOYSA-N 0.000 description 2
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- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- MJWDKAHWCMOBIQ-UHFFFAOYSA-N 11-(3,4,5-trimethoxyphenyl)-14-oxa-17-azatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,8,12(16)-hexaene-13-thione Chemical compound COC1=C(OC)C(OC)=CC(C2C3=C(C4=CC=CC=C4C=C3)NC3=C2C(OC3)=S)=C1 MJWDKAHWCMOBIQ-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
- VUGQIIQFXCXZJU-UHFFFAOYSA-N 3,4,5-trimethoxyacetophenone Chemical compound COC1=CC(C(C)=O)=CC(OC)=C1OC VUGQIIQFXCXZJU-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
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- ZFMZSZMUFWRAOG-UHFFFAOYSA-N 3-methoxy-n-methylaniline Chemical compound CNC1=CC=CC(OC)=C1 ZFMZSZMUFWRAOG-UHFFFAOYSA-N 0.000 description 1
- FZYGATLKLHAMAP-UHFFFAOYSA-N 3h-furo[3,4-b]quinolin-1-one Chemical class C1=CC=C2C=C3C(=O)OCC3=NC2=C1 FZYGATLKLHAMAP-UHFFFAOYSA-N 0.000 description 1
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- WXVSKXAVZMWHHX-UHFFFAOYSA-N 5-methyl-8-(3,4,5-trimethoxyphenyl)-12,14-dioxa-2,5-diazatetracyclo[7.7.0.03,7.011,15]hexadeca-1(16),3(7),9,11(15)-tetraen-6-one Chemical compound COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3NC3=C2C(N(C)C3)=O)=C1 WXVSKXAVZMWHHX-UHFFFAOYSA-N 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000003831 tetrazolyl 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
- 238000007280 thionation reaction Methods 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D497/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms
- C07D497/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having oxygen and sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D497/14—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0106792A FR2825091B1 (fr) | 2001-05-23 | 2001-05-23 | Nouveaux derives tricycliques de dihydro-quinnoleines, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200308629B true ZA200308629B (en) | 2004-11-05 |
Family
ID=8863589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200308629A ZA200308629B (en) | 2001-05-23 | 2003-11-05 | Tricyclic dihydro-quinoline derivatives, method for preparing same and pharmaceutical compositions containing same. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US20040198981A1 (pt) |
| EP (1) | EP1389210A1 (pt) |
| JP (1) | JP2004535405A (pt) |
| KR (1) | KR20030097898A (pt) |
| CN (1) | CN1511158A (pt) |
| AR (1) | AR033915A1 (pt) |
| BR (1) | BR0209974A (pt) |
| CA (1) | CA2448191A1 (pt) |
| CZ (1) | CZ20033495A3 (pt) |
| EA (1) | EA200301171A1 (pt) |
| FR (1) | FR2825091B1 (pt) |
| HU (1) | HUP0400436A2 (pt) |
| MX (1) | MXPA03010599A (pt) |
| NO (1) | NO20035215L (pt) |
| PL (1) | PL364082A1 (pt) |
| SK (1) | SK16022003A3 (pt) |
| WO (1) | WO2002094835A1 (pt) |
| ZA (1) | ZA200308629B (pt) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE455115T1 (de) * | 2005-07-20 | 2010-01-15 | Aventis Pharma Sa | 1,4-dihydropyridine-kondensierte heterocyclen verfahren zu deren herstellung sowie verwendung und zusammensetzungen dergleichen |
| WO2012076942A1 (en) * | 2010-12-06 | 2012-06-14 | Council Of Scientific & Industrial Research | 4-aza-2, 3-didehydropodophyllotoxin compounds and process for the preparation thereof |
| AU2015205995A1 (en) | 2014-01-15 | 2016-07-28 | Centre National De La Recherche Scientifique (Cnrs) | Water soluble 4-azapodophyllotoxin analogs |
| WO2017151947A1 (en) * | 2016-03-02 | 2017-09-08 | George Robert Pettit | 4-azapodophylotoxins compounds |
| CN111494374B (zh) * | 2020-06-12 | 2021-08-03 | 广东省微生物研究所（广东省微生物分析检测中心） | 香草木宁碱在制备破骨细胞分化抑制剂中的应用 |
| CN114989180B (zh) * | 2022-05-26 | 2024-06-04 | 广东海洋大学 | 杨叶肖槿内生真菌来源的化合物及其制备方法与应用 |
| WO2024015793A2 (en) * | 2022-07-12 | 2024-01-18 | Oregon Health & Science University | Enantiomer of azopodophyllotoxin derivative su056 |
| US11731980B1 (en) | 2023-03-22 | 2023-08-22 | King Faisal University | Furo[3,4-b]quinolone compounds as antibacterial agents |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2801310B1 (fr) * | 1999-11-24 | 2004-04-16 | Adir | NOUVEAUX DERIVES DE DIHYDROFURO-[3,4-b]QUINOLEIN-1-ONES, LEUR PROCEDE DE PREPARATION ET LES COMPOSITIONS PHARMACEUTIQUES QUI LES CONTIENNENT |
-
2001
- 2001-05-23 FR FR0106792A patent/FR2825091B1/fr not_active Expired - Fee Related
-
2002
- 2002-05-22 CA CA002448191A patent/CA2448191A1/fr not_active Abandoned
- 2002-05-22 BR BR0209974-8A patent/BR0209974A/pt not_active Application Discontinuation
- 2002-05-22 SK SK1602-2003A patent/SK16022003A3/sk unknown
- 2002-05-22 EA EA200301171A patent/EA200301171A1/ru unknown
- 2002-05-22 HU HU0400436A patent/HUP0400436A2/hu unknown
- 2002-05-22 CN CNA028102746A patent/CN1511158A/zh active Pending
- 2002-05-22 CZ CZ20033495A patent/CZ20033495A3/cs unknown
- 2002-05-22 US US10/477,258 patent/US20040198981A1/en not_active Abandoned
- 2002-05-22 KR KR10-2003-7015306A patent/KR20030097898A/ko not_active Application Discontinuation
- 2002-05-22 WO PCT/FR2002/001715 patent/WO2002094835A1/fr not_active Application Discontinuation
- 2002-05-22 PL PL02364082A patent/PL364082A1/xx unknown
- 2002-05-22 MX MXPA03010599A patent/MXPA03010599A/es unknown
- 2002-05-22 JP JP2002591508A patent/JP2004535405A/ja not_active Withdrawn
- 2002-05-22 EP EP02740805A patent/EP1389210A1/fr not_active Withdrawn
- 2002-05-23 AR ARP020101906A patent/AR033915A1/es not_active Application Discontinuation
-
2003
- 2003-11-05 ZA ZA200308629A patent/ZA200308629B/en unknown
- 2003-11-24 NO NO20035215A patent/NO20035215L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| WO2002094835A1 (fr) | 2002-11-28 |
| SK16022003A3 (sk) | 2004-05-04 |
| CN1511158A (zh) | 2004-07-07 |
| US20040198981A1 (en) | 2004-10-07 |
| MXPA03010599A (es) | 2004-03-09 |
| NO20035215D0 (no) | 2003-11-24 |
| JP2004535405A (ja) | 2004-11-25 |
| FR2825091B1 (fr) | 2003-07-04 |
| KR20030097898A (ko) | 2003-12-31 |
| EP1389210A1 (fr) | 2004-02-18 |
| FR2825091A1 (fr) | 2002-11-29 |
| AR033915A1 (es) | 2004-01-07 |
| BR0209974A (pt) | 2004-04-06 |
| EA200301171A1 (ru) | 2004-04-29 |
| HUP0400436A2 (hu) | 2004-09-28 |
| CZ20033495A3 (en) | 2004-05-12 |
| NO20035215L (no) | 2003-11-24 |
| CA2448191A1 (fr) | 2002-11-28 |
| PL364082A1 (en) | 2004-12-13 |
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