ZA200304646B - Dihydroindole and tetrahydroquinoline derivatives. - Google Patents
Dihydroindole and tetrahydroquinoline derivatives. Download PDFInfo
- Publication number
- ZA200304646B ZA200304646B ZA200304646A ZA200304646A ZA200304646B ZA 200304646 B ZA200304646 B ZA 200304646B ZA 200304646 A ZA200304646 A ZA 200304646A ZA 200304646 A ZA200304646 A ZA 200304646A ZA 200304646 B ZA200304646 B ZA 200304646B
- Authority
- ZA
- South Africa
- Prior art keywords
- methyl
- alkyl
- dihydro
- amino
- allyl
- Prior art date
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- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 title description 3
- 125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 150000002148 esters Chemical class 0.000 claims description 16
- 238000011321 prophylaxis Methods 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 14
- -1 aryl- lower-alkyl Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 239000000460 chlorine Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical group CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Chemical group 0.000 claims description 7
- 201000010099 disease Diseases 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 206010012601 diabetes mellitus Diseases 0.000 claims description 6
- 230000003463 hyperproliferative effect Effects 0.000 claims description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical group CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 208000019553 vascular disease Diseases 0.000 claims description 6
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 208000031888 Mycoses Diseases 0.000 claims description 5
- 208000030852 Parasitic disease Diseases 0.000 claims description 5
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 201000001883 cholelithiasis Diseases 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 201000005577 familial hyperlipidemia Diseases 0.000 claims description 5
- 208000001130 gallstones Diseases 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 230000036281 parasite infection Effects 0.000 claims description 5
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 16
- 239000000203 mixture Substances 0.000 claims 10
- 206010003210 Arteriosclerosis Diseases 0.000 claims 4
- 208000002705 Glucose Intolerance Diseases 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 4
- 201000009104 prediabetes syndrome Diseases 0.000 claims 4
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical group [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 claims 4
- 229910052740 iodine Inorganic materials 0.000 claims 3
- 239000013543 active substance Substances 0.000 claims 2
- VJROPLWGFCORRM-UHFFFAOYSA-N 2-methylbutan-1-amine Chemical compound CCC(C)CN VJROPLWGFCORRM-UHFFFAOYSA-N 0.000 claims 1
- 239000002671 adjuvant Substances 0.000 claims 1
- MSZJEPVVQWJCIF-UHFFFAOYSA-N butylazanide Chemical compound CCCC[NH-] MSZJEPVVQWJCIF-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- KEOLJAPWYNIYSB-UHFFFAOYSA-N phenyl 6-fluoro-5-[5-[methyl(propyl)amino]pentyl]-2,3-dihydroindole-1-carboxylate Chemical compound C1=2C=C(F)C(CCCCCN(C)CCC)=CC=2CCN1C(=O)OC1=CC=CC=C1 KEOLJAPWYNIYSB-UHFFFAOYSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 23
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 22
- 108010028554 LDL Cholesterol Proteins 0.000 description 12
- 125000000217 alkyl group Chemical group 0.000 description 11
- 235000012000 cholesterol Nutrition 0.000 description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 208000029078 coronary artery disease Diseases 0.000 description 6
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
- UHBGYFCCKRAEHA-UHFFFAOYSA-N P-toluamide Chemical compound CC1=CC=C(C(N)=O)C=C1 UHBGYFCCKRAEHA-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229930182558 Sterol Natural products 0.000 description 4
- JPYQFYIEOUVJDU-UHFFFAOYSA-N beclamide Chemical compound ClCCC(=O)NCC1=CC=CC=C1 JPYQFYIEOUVJDU-UHFFFAOYSA-N 0.000 description 4
- 150000002632 lipids Chemical class 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 150000003432 sterols Chemical class 0.000 description 4
- 235000003702 sterols Nutrition 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 3
- OSENKJZWYQXHBN-XVYZBDJZSA-N 24(S),25-epoxycholesterol Chemical compound C([C@@H](C)[C@@H]1[C@]2(CC[C@@H]3[C@@]4(C)CC[C@H](O)CC4=CC[C@H]3[C@@H]2CC1)C)C[C@@H]1OC1(C)C OSENKJZWYQXHBN-XVYZBDJZSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 201000001320 Atherosclerosis Diseases 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- 108010023302 HDL Cholesterol Proteins 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000004450 alkenylene group Chemical group 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229940125753 fibrate Drugs 0.000 description 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 description 2
- RQOCXCFLRBRBCS-UHFFFAOYSA-N (22E)-cholesta-5,7,22-trien-3beta-ol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CCC(C)C)CCC33)C)C3=CC=C21 RQOCXCFLRBRBCS-UHFFFAOYSA-N 0.000 description 2
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical class C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 2
- 101710158485 3-hydroxy-3-methylglutaryl-coenzyme A reductase Proteins 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
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 2
- KRZCOLNOCZKSDF-UHFFFAOYSA-N 4-fluoroaniline Chemical compound NC1=CC=C(F)C=C1 KRZCOLNOCZKSDF-UHFFFAOYSA-N 0.000 description 2
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 2
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 description 2
- BPYKTIZUTYGOLE-IFADSCNNSA-N Bilirubin Chemical compound N1C(=O)C(C)=C(C=C)\C1=C\C1=C(C)C(CCC(O)=O)=C(CC2=C(C(C)=C(\C=C/3C(=C(C=C)C(=O)N\3)C)N2)CCC(O)=O)N1 BPYKTIZUTYGOLE-IFADSCNNSA-N 0.000 description 2
- 101710095468 Cyclase Proteins 0.000 description 2
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- 125000004429 atom Chemical group 0.000 description 2
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- 230000001364 causal effect Effects 0.000 description 2
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- ACTIUHUUMQJHFO-UPTCCGCDSA-N coenzyme Q10 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)=C(C)C1=O ACTIUHUUMQJHFO-UPTCCGCDSA-N 0.000 description 2
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- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
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- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 2
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Classifications
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- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
Landscapes
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- Tropical Medicine & Parasitology (AREA)
- Urology & Nephrology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
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| EP00128063 | 2000-12-21 |
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| CN (1) | CN1208322C (enExample) |
| AR (1) | AR035408A1 (enExample) |
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| HRP20050181A2 (en) * | 2002-08-29 | 2006-03-31 | Merck & Co. Inc. | Indoles having anti-diabetic activity |
| JP4479656B2 (ja) * | 2003-08-08 | 2010-06-09 | 宇部興産株式会社 | アルキニル基置換縮合ヘテロ環化合物及びその製法並びにそれを使用する有機エレクトロルミネッセンス素子 |
| TWI329102B (en) * | 2006-08-15 | 2010-08-21 | Nat Health Research Institutes | Thiourea compounds and method for inhibiting hepatitis c virus infection |
| WO2008124300A1 (en) * | 2007-04-10 | 2008-10-16 | National Health Research Institutes | Hepatitis c virus inhibitors |
| WO2008154091A1 (en) * | 2007-06-08 | 2008-12-18 | National Health Research Institutes | Thiourea derivatives |
| TWI361808B (en) * | 2008-01-08 | 2012-04-11 | Nat Health Research Institutes | Imidazolidinone and imidazolidinethione derivatives |
| US8198284B2 (en) * | 2008-04-30 | 2012-06-12 | National Health Research Institutes | Treatment of neurodegenerative disorders with thiourea compounds |
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| US3997542A (en) * | 1975-06-23 | 1976-12-14 | Sterling Drug Inc. | 1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof |
| NZ227042A (en) | 1987-11-27 | 1991-05-28 | Banyu Pharma Co Ltd | Substituted alkylamine derivatives and pharmaceutical compositions |
| US5288749A (en) | 1991-12-20 | 1994-02-22 | Abbott Laboratories | Tertiary and secondary amines as alpha-2 antagonists and serotonin uptake inhibitors |
| TW438774B (en) | 1993-07-14 | 2001-06-07 | Hoffmann La Roche | Pharmaceutical composition for lowering cholesterol containing phenalkylamines and certain novel phenalkylamines |
| AU1608397A (en) | 1996-02-02 | 1997-08-22 | Zeneca Limited | Heterocyclic compounds useful as pharmaceutical agents |
| DE19727117A1 (de) | 1997-06-26 | 1999-01-07 | Boehringer Ingelheim Pharma | Phenylalkylderivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US7229986B2 (en) | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
-
2001
- 2001-12-11 US US10/014,959 patent/US6706751B2/en not_active Expired - Fee Related
- 2001-12-12 AU AU1917602A patent/AU1917602A/xx active Pending
- 2001-12-12 DE DE60117096T patent/DE60117096T2/de not_active Expired - Lifetime
- 2001-12-12 MX MXPA03005395A patent/MXPA03005395A/es active IP Right Grant
- 2001-12-12 KR KR10-2003-7008393A patent/KR100530408B1/ko not_active Expired - Fee Related
- 2001-12-12 WO PCT/EP2001/014620 patent/WO2002050041A1/en not_active Ceased
- 2001-12-12 ES ES01271362T patent/ES2257381T3/es not_active Expired - Lifetime
- 2001-12-12 JP JP2002551538A patent/JP4068459B2/ja not_active Expired - Fee Related
- 2001-12-12 AT AT01271362T patent/ATE317386T1/de not_active IP Right Cessation
- 2001-12-12 AU AU2002219176A patent/AU2002219176B2/en not_active Ceased
- 2001-12-12 BR BR0116263-2A patent/BR0116263A/pt not_active IP Right Cessation
- 2001-12-12 CA CA002431100A patent/CA2431100C/en not_active Expired - Fee Related
- 2001-12-12 EP EP01271362A patent/EP1358162B1/en not_active Expired - Lifetime
- 2001-12-12 CN CNB018210120A patent/CN1208322C/zh not_active Expired - Fee Related
- 2001-12-20 AR ARP010105925A patent/AR035408A1/es unknown
-
2003
- 2003-06-13 ZA ZA200304646A patent/ZA200304646B/en unknown
- 2003-08-26 US US10/648,451 patent/US7102007B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2004519441A (ja) | 2004-07-02 |
| US7102007B2 (en) | 2006-09-05 |
| AR035408A1 (es) | 2004-05-26 |
| CN1481366A (zh) | 2004-03-10 |
| ATE317386T1 (de) | 2006-02-15 |
| CA2431100C (en) | 2009-03-24 |
| BR0116263A (pt) | 2003-12-30 |
| US20030004156A1 (en) | 2003-01-02 |
| DE60117096D1 (de) | 2006-04-20 |
| EP1358162A1 (en) | 2003-11-05 |
| KR100530408B1 (ko) | 2005-11-22 |
| WO2002050041A1 (en) | 2002-06-27 |
| AU2002219176B2 (en) | 2006-02-09 |
| JP4068459B2 (ja) | 2008-03-26 |
| US20050020624A1 (en) | 2005-01-27 |
| KR20030063453A (ko) | 2003-07-28 |
| EP1358162B1 (en) | 2006-02-08 |
| AU1917602A (en) | 2002-07-01 |
| MXPA03005395A (es) | 2003-09-25 |
| CN1208322C (zh) | 2005-06-29 |
| CA2431100A1 (en) | 2002-06-27 |
| US6706751B2 (en) | 2004-03-16 |
| DE60117096T2 (de) | 2006-11-23 |
| ES2257381T3 (es) | 2006-08-01 |
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