DE60102473T2 - Indolochinazolinone - Google Patents
Indolochinazolinone Download PDFInfo
- Publication number
- DE60102473T2 DE60102473T2 DE60102473T DE60102473T DE60102473T2 DE 60102473 T2 DE60102473 T2 DE 60102473T2 DE 60102473 T DE60102473 T DE 60102473T DE 60102473 T DE60102473 T DE 60102473T DE 60102473 T2 DE60102473 T2 DE 60102473T2
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- acid addition
- free base
- addition salt
- compound according
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 239000002253 acid Substances 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 11
- 229920000776 Poly(Adenosine diphosphate-ribose) polymerase Polymers 0.000 claims description 9
- -1 cyano, tetrazolyl Chemical group 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000000304 alkynyl group Chemical group 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- MUCVVURUYXBTPX-UHFFFAOYSA-N 7-(2h-tetrazol-5-ylmethyl)-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C12=CC=CC=C2N2C3=CC=CC=C3C(=O)NC2=C1CC1=NN=NN1 MUCVVURUYXBTPX-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 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 description 3
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005242 carbamoyl alkyl group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000003386 piperidinyl group Chemical group 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
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- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- INSBKYCYLCEBOD-UHFFFAOYSA-N (5-oxo-5,6-dihydro-indolo[1,2-a]quinazolin-7-yl)-acetic acid Chemical compound C1=CC=C2N3C4=CC=CC=C4C(CC(=O)O)=C3NC(=O)C2=C1 INSBKYCYLCEBOD-UHFFFAOYSA-N 0.000 description 5
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- JUGKQCJQHACNBE-UHFFFAOYSA-N 5-oxo-6h-benzo[b][1]benzazepine-11-carbonitrile Chemical compound O=C1CC2=CC=CC=C2N(C#N)C2=CC=CC=C12 JUGKQCJQHACNBE-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 102100023712 Poly [ADP-ribose] polymerase 1 Human genes 0.000 description 3
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- OHBFRBSVXWHHOS-UHFFFAOYSA-N 2-(5-oxo-6h-indolo[1,2-a]quinazolin-7-yl)acetonitrile Chemical compound C1=CC=C2C(=O)NC3=C(CC#N)C4=CC=CC=C4N3C2=C1 OHBFRBSVXWHHOS-UHFFFAOYSA-N 0.000 description 2
- UHFGPTBDIOCKIW-UHFFFAOYSA-N 2-(5-oxo-6h-indolo[1,2-a]quinazolin-7-yl)butanenitrile Chemical compound C1=CC=C2N3C4=CC=CC=C4C(C(C#N)CC)=C3NC(=O)C2=C1 UHFGPTBDIOCKIW-UHFFFAOYSA-N 0.000 description 2
- IWGDCYSIZRGZLS-UHFFFAOYSA-N 7-ethyl-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C1=CC=C2N3C4=CC=CC=C4C(CC)=C3NC(=O)C2=C1 IWGDCYSIZRGZLS-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
- 239000012661 PARP inhibitor Substances 0.000 description 2
- 208000002193 Pain Diseases 0.000 description 2
- 229940121906 Poly ADP ribose polymerase inhibitor Drugs 0.000 description 2
- 102000012338 Poly(ADP-ribose) Polymerases Human genes 0.000 description 2
- 108010061844 Poly(ADP-ribose) Polymerases Proteins 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 206010040070 Septic Shock Diseases 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
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- 210000004027 cell Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 230000007574 infarction Effects 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 208000015122 neurodegenerative disease Diseases 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 229960001412 pentobarbital Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- JJDWJCXUXXUTGE-UHFFFAOYSA-N 7-(2-aminobutyl)-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C1=CC=C2N3C4=CC=CC=C4C(CC(N)CC)=C3NC(=O)C2=C1 JJDWJCXUXXUTGE-UHFFFAOYSA-N 0.000 description 1
- SMCWOYGQJBWVCG-UHFFFAOYSA-N 7-(2-aminoethyl)-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C1=CC=C2N3C4=CC=CC=C4C(CCN)=C3NC(=O)C2=C1 SMCWOYGQJBWVCG-UHFFFAOYSA-N 0.000 description 1
- FWJBOZTXDAXBHF-UHFFFAOYSA-N 7-(2-hydroxyethyl)-6h-indolo[1,2-a]quinazolin-5-one Chemical compound C1=CC=C2N3C4=CC=CC=C4C(CCO)=C3NC(=O)C2=C1 FWJBOZTXDAXBHF-UHFFFAOYSA-N 0.000 description 1
- NLCLQLBSAYPDBO-UHFFFAOYSA-N 7-[2-(2-oxopyrrolidin-1-yl)ethyl]-6h-indolo[1,2-a]quinazolin-5-one Chemical compound O=C1CCCN1CCC1=C(NC(=O)C=2C3=CC=CC=2)N3C2=CC=CC=C21 NLCLQLBSAYPDBO-UHFFFAOYSA-N 0.000 description 1
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- 239000012359 Methanesulfonyl chloride Substances 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
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- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- RFPSQXNAKXLFMW-UHFFFAOYSA-N pyrimido[5,4-c]carbazol-2-one Chemical class N1=C2C=CC=CC2=C2C1=CC=C1C=NC(=O)N=C12 RFPSQXNAKXLFMW-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0017508 | 2000-07-17 | ||
| GBGB0017508.3A GB0017508D0 (en) | 2000-07-17 | 2000-07-17 | Antimicrobials |
| PCT/EP2001/008192 WO2002006284A1 (en) | 2000-07-17 | 2001-07-16 | Indoloquinazolinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE60102473D1 DE60102473D1 (de) | 2004-04-29 |
| DE60102473T2 true DE60102473T2 (de) | 2005-02-03 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE60102473T Expired - Lifetime DE60102473T2 (de) | 2000-07-17 | 2001-07-16 | Indolochinazolinone |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6964960B2 (enExample) |
| EP (1) | EP1303517B1 (enExample) |
| JP (1) | JP3939246B2 (enExample) |
| CN (1) | CN1183136C (enExample) |
| AR (1) | AR031379A1 (enExample) |
| AT (1) | ATE262530T1 (enExample) |
| AU (1) | AU2001279754A1 (enExample) |
| BR (1) | BR0112521A (enExample) |
| CA (1) | CA2415683C (enExample) |
| DE (1) | DE60102473T2 (enExample) |
| DK (1) | DK1303517T3 (enExample) |
| ES (1) | ES2218439T3 (enExample) |
| GB (1) | GB0017508D0 (enExample) |
| MY (1) | MY133969A (enExample) |
| PE (1) | PE20020210A1 (enExample) |
| PT (1) | PT1303517E (enExample) |
| TR (1) | TR200401026T4 (enExample) |
| WO (1) | WO2002006284A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6956035B2 (en) | 2001-08-31 | 2005-10-18 | Inotek Pharmaceuticals Corporation | Isoquinoline derivatives and methods of use thereof |
| JP2007501857A (ja) | 2003-02-28 | 2007-02-01 | イノテック ファーマシューティカルズ コーポレーション | 四環系ベンズアミド誘導体およびその使用方法 |
| US7381722B2 (en) | 2005-02-25 | 2008-06-03 | Inotek Pharmaceuticals Corporation | Tetracyclic amino and carboxamido compounds and methods of use thereof |
| CA2620052A1 (en) | 2005-08-24 | 2007-03-01 | Inotek Pharmaceuticals Corporation | Indenoisoquinolinone analogs and methods of use thereof |
| JP5284955B2 (ja) * | 2006-06-20 | 2013-09-11 | アボット・ラボラトリーズ | Ｐａｒｐ阻害剤としてのピラゾロキナゾリノン |
| GB0615809D0 (en) * | 2006-08-09 | 2006-09-20 | Istituto Di Ricerche D Biolog | Therapeutic compounds |
| GB0701273D0 (en) * | 2007-01-24 | 2007-02-28 | Angeletti P Ist Richerche Bio | New compounds |
| CA2677046A1 (en) | 2007-02-28 | 2008-09-04 | Inotek Pharmaceuticals Corporation | Indenoisoquinolinone analogs and methods of use thereof |
| TW200845962A (en) | 2007-05-08 | 2008-12-01 | Schering Corp | Methods of treatment using intravenous formulations comprising temozolomide |
| ES2562903T3 (es) * | 2011-07-13 | 2016-03-09 | Santen Pharmaceutical Co., Ltd | Nuevo compuesto que tiene actividad inhibidora de PARP |
| CN102766144B (zh) * | 2012-07-10 | 2014-04-23 | 浙江大学 | 一种吲哚并[1,2-c]喹唑啉化合物的制备方法 |
| JP6457696B2 (ja) | 2015-07-23 | 2019-01-23 | アンスティテュ・キュリＩｎｓｔｉｔｕｔ Ｃｕｒｉｅ | 癌を処置するためのＤｂａｉｔ分子とＰＡＲＰインヒビターとの組合せの使用 |
| GB201519573D0 (en) | 2015-11-05 | 2015-12-23 | King S College London | Combination |
| WO2018162439A1 (en) | 2017-03-08 | 2018-09-13 | Onxeo | New predictive biomarker for the sensitivity to a treatment of cancer with a dbait molecule |
| WO2019175132A1 (en) | 2018-03-13 | 2019-09-19 | Onxeo | A dbait molecule against acquired resistance in the treatment of cancer |
| CN113169274A (zh) * | 2018-11-30 | 2021-07-23 | 默克专利有限公司 | 用于电子器件的化合物 |
| EP3938367A1 (de) * | 2019-03-12 | 2022-01-19 | Merck Patent GmbH | Materialien für organische elektrolumineszenzvorrichtungen |
| CN110357892B (zh) * | 2019-07-10 | 2022-06-07 | 云南大学 | 四氢嘧啶并[1,2-a]吲哚衍生物及其合成方法与应用 |
| WO2021148581A1 (en) | 2020-01-22 | 2021-07-29 | Onxeo | Novel dbait molecule and its use |
| CN114195789B (zh) * | 2021-12-15 | 2022-09-09 | 广东海洋大学 | 一种无金属参与的多环吲哚衍生物的制备方法 |
| WO2024261243A1 (en) | 2023-06-21 | 2024-12-26 | Hemispherian As | Combination comprising a deoxycytidine derivative and a parp inhibitor for use in a method of treating hr proficient cancer |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3635966A (en) | 1969-10-22 | 1972-01-18 | Robins Co Inc A H | 6-substituted-indolo(1 2-c)quinazolines |
| DE2237372C3 (de) | 1972-07-29 | 1981-07-09 | Basf Ag, 6700 Ludwigshafen | Heterocyclische Farbstoffe, ihre Herstellung und ihre Verwendung |
| US5441955A (en) * | 1993-11-19 | 1995-08-15 | Pathogenesis Corporation | Indolo[2,1-biquinazoline-6,12-dione antibacterial compounds and methods of use thereof |
| GB9404485D0 (en) * | 1994-03-09 | 1994-04-20 | Cancer Res Campaign Tech | Benzamide analogues |
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2000
- 2000-07-17 GB GBGB0017508.3A patent/GB0017508D0/en not_active Ceased
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2001
- 2001-07-12 PE PE2001000700A patent/PE20020210A1/es not_active Application Discontinuation
- 2001-07-13 AR ARP010103339A patent/AR031379A1/es not_active Application Discontinuation
- 2001-07-13 MY MYPI20013343 patent/MY133969A/en unknown
- 2001-07-16 DK DK01957972T patent/DK1303517T3/da active
- 2001-07-16 JP JP2002512186A patent/JP3939246B2/ja not_active Expired - Fee Related
- 2001-07-16 US US10/333,186 patent/US6964960B2/en not_active Expired - Fee Related
- 2001-07-16 EP EP01957972A patent/EP1303517B1/en not_active Expired - Lifetime
- 2001-07-16 ES ES01957972T patent/ES2218439T3/es not_active Expired - Lifetime
- 2001-07-16 DE DE60102473T patent/DE60102473T2/de not_active Expired - Lifetime
- 2001-07-16 WO PCT/EP2001/008192 patent/WO2002006284A1/en not_active Ceased
- 2001-07-16 CA CA002415683A patent/CA2415683C/en not_active Expired - Fee Related
- 2001-07-16 PT PT01957972T patent/PT1303517E/pt unknown
- 2001-07-16 AT AT01957972T patent/ATE262530T1/de not_active IP Right Cessation
- 2001-07-16 CN CNB018126995A patent/CN1183136C/zh not_active Expired - Fee Related
- 2001-07-16 BR BR0112521-4A patent/BR0112521A/pt not_active Application Discontinuation
- 2001-07-16 AU AU2001279754A patent/AU2001279754A1/en not_active Abandoned
- 2001-07-16 TR TR2004/01026T patent/TR200401026T4/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP3939246B2 (ja) | 2007-07-04 |
| CA2415683C (en) | 2009-12-29 |
| BR0112521A (pt) | 2003-07-01 |
| AU2001279754A1 (en) | 2002-01-30 |
| AR031379A1 (es) | 2003-09-24 |
| EP1303517B1 (en) | 2004-03-24 |
| CN1183136C (zh) | 2005-01-05 |
| CN1441803A (zh) | 2003-09-10 |
| PT1303517E (pt) | 2004-07-30 |
| US6964960B2 (en) | 2005-11-15 |
| MY133969A (en) | 2007-11-30 |
| DK1303517T3 (da) | 2004-06-21 |
| EP1303517A1 (en) | 2003-04-23 |
| GB0017508D0 (en) | 2000-08-30 |
| WO2002006284A1 (en) | 2002-01-24 |
| HK1056872A1 (en) | 2004-03-05 |
| DE60102473D1 (de) | 2004-04-29 |
| TR200401026T4 (tr) | 2004-07-21 |
| ATE262530T1 (de) | 2004-04-15 |
| JP2004504323A (ja) | 2004-02-12 |
| HK1055426A1 (en) | 2004-01-09 |
| PE20020210A1 (es) | 2002-04-04 |
| ES2218439T3 (es) | 2004-11-16 |
| CA2415683A1 (en) | 2002-01-24 |
| US20030199502A1 (en) | 2003-10-23 |
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Representative=s name: DR. SCHOEN & PARTNER, 80336 MUENCHEN |