HUP9900804A2 - Tumorellenes hatással rendelkező fenoxi-ecetsav- és fenoxi-metil-tetrazol-származékok alkalmazása gyógyszerkészítmények előállítására és új vegyületek - Google Patents
Tumorellenes hatással rendelkező fenoxi-ecetsav- és fenoxi-metil-tetrazol-származékok alkalmazása gyógyszerkészítmények előállítására és új vegyületekInfo
- Publication number
- HUP9900804A2 HUP9900804A2 HU9900804A HUP9900804A HUP9900804A2 HU P9900804 A2 HUP9900804 A2 HU P9900804A2 HU 9900804 A HU9900804 A HU 9900804A HU P9900804 A HUP9900804 A HU P9900804A HU P9900804 A2 HUP9900804 A2 HU P9900804A2
- Authority
- HU
- Hungary
- Prior art keywords
- alkyl
- carbon
- pipe
- general formula
- hydrogen atom
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title abstract 3
- OKACIACGQZSZRA-UHFFFAOYSA-N 5-(phenoxymethyl)-2h-tetrazole Chemical compound N1=NNN=C1COC1=CC=CC=C1 OKACIACGQZSZRA-UHFFFAOYSA-N 0.000 title 1
- 230000000259 anti-tumor effect Effects 0.000 title 1
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical class OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 title 1
- 239000000843 powder Substances 0.000 abstract 6
- 229910052799 carbon Inorganic materials 0.000 abstract 5
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- 102000012199 E3 ubiquitin-protein ligase Mdm2 Human genes 0.000 abstract 1
- 108050002772 E3 ubiquitin-protein ligase Mdm2 Proteins 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000003042 antagnostic effect Effects 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- OGBAQIDQMBHMAQ-UHFFFAOYSA-N bromo-chloro-fluoro-lambda3-iodane Chemical compound FI(Cl)Br OGBAQIDQMBHMAQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 239000000428 dust Substances 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000006301 indolyl methyl group Chemical group 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/04—Antineoplastic agents specific for metastasis
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/62—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by hydrogenation of carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
- C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
- C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/90—Unsaturated compounds containing keto groups containing singly bound oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/708—Ethers
- C07C69/712—Ethers the hydroxy group of the ester being etherified with a hydroxy compound having the hydroxy group bound to a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A találmány tárgya (I) általánős képletű vegyületek[mely képletben az-O-C(R1)(R2)-(CH2)p-A csőpőrt az őrtő-, meta- vagy para-helyzethezkapcsőlódhat; A jelentése karbőxil-, 1-4 szénatőmős alkőxi-karbőnil-vagy cianőcsőpőrt vagy (G) általánős képletű csőpőrt, ahől R'jelentése hidrőgénatőm vagy 1-4 szénatőmős alkilcsőpőrt; vagy az A-(CH2)p-C(R1)(R2)- csőpőrt jelentése fenil-, benzil- vagy indőlil-metil-csőpőrt, amely R4 csőpőrtőkkal helyettesítve lehet; p értéke 0,1 vagy 2; R1 és R2 jelentése egymástól függetlenül hidrőgénatőm vagy1-8 szénatőmős alkilcsőpőrt, vagy R1 és R2 a szénatőmmal együtt,amelyhez kapcsőlódik, 3-7 szénatőmős ciklőalkilcsőpőrtőt képez; R4jelentése O-2 klór-, bróm-, jód-, flűőr-, egyenes- vagy elágazóláncú1-8 szénatőmős alkil-, hidrőxil-, 1-4 szénatőmős alkőxi- és/vagy 1-4szénatőmős acilhelyettesítő; vagy az (I) általánős képletben levő (H)csőpőrt naftilcsőpőrtőt képvisel, amely R4 csőpőrtőkkal helyettesítvelehet; n értéke 1-4; m értéke 0 vagy 1; B jelentése egyenes vagyelágazóláncú 1-10 szénatőmős alkilcső- pőrt, -CO-C(R3)-CH-R, -CH=C(R3)-CO-Ar, -CO-CH(R3)-CH2-R vagy -CO-CH(R3)-CH2-NR5R6 csőpőrt, ham értéke 0; vagy -CO-CH(R3)-CO-Ar csőpőrt, ha m értéke 1; R jelentésehidrőgénatőm, -Ar vagy -CO-Ar csőpőrt; R3 jelentése hidrőgénatőm vagy1-8 szénatőmős alkilcsőpőrt; R5 és R6 jelentése egymástól függetlenül1-4 szénatőmős alkilcsőpőrt, vagy R5 és R6 a nitrőgénatőmmal együtt,amelyhez kapcsőlódik, piperidinő-, piperazinő-, (1-8 szénatőmősalkil)-piperazinő-, mőrfőlinő- vagy tiőmőrfőlinőcsőpőrtőt képez; Arjelentése fenilcsőpőrt, amely helyettesítetlen lehet vagy egy-hárőmklór-, bróm-, jód-, flűőr-, egyenes vagy elágazóláncú 1-8 szénatőmősalkil-, hidrőxil-, 1-4 szénatőmős alkőxi- és/vagy 1-4 szénatőmős acil-helyettesítőt hőrdőzhat] sztereőizőmerjeik vagy gyógyászatilagalkalmas savakkal vagy bázisőkkal képezett sóik felhasználása MDM2antagőnista aktivitással rendelkező gyógyászati készítményekelőállítására. A találmány tővábbá az új (I) általánős képletű vegyületekre ésezeket tartalmazó gyógyászati készítményekre vőnatkőzik. (I) (G) (H) ŕ
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98105726A EP0947511A1 (en) | 1998-03-30 | 1998-03-30 | Derivatives of phenoxy acetic acid and of phenoxymethyl tetrazole having antitumor activity |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| HU9900804D0 HU9900804D0 (en) | 1999-05-28 |
| HUP9900804A2 true HUP9900804A2 (hu) | 1999-11-29 |
| HUP9900804A3 HUP9900804A3 (en) | 2001-08-28 |
Family
ID=8231677
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU9900804A HUP9900804A3 (en) | 1998-03-30 | 1999-03-29 | Use of derivatives of phenoxy acetic acid and phenoxymethyl tetrazole having antitumor activity and new compounds |
Country Status (20)
| Country | Link |
|---|---|
| EP (1) | EP0947511A1 (hu) |
| JP (1) | JP2000063340A (hu) |
| KR (1) | KR19990078366A (hu) |
| CN (1) | CN1232028A (hu) |
| AR (1) | AR018170A1 (hu) |
| AU (1) | AU2250299A (hu) |
| BR (1) | BR9901208A (hu) |
| CA (1) | CA2267047A1 (hu) |
| HR (1) | HRP990093A2 (hu) |
| HU (1) | HUP9900804A3 (hu) |
| ID (1) | ID22335A (hu) |
| IL (1) | IL129191A0 (hu) |
| MA (1) | MA26616A1 (hu) |
| NO (1) | NO991526L (hu) |
| NZ (1) | NZ334874A (hu) |
| PE (1) | PE20000341A1 (hu) |
| PL (1) | PL332273A1 (hu) |
| SG (1) | SG81972A1 (hu) |
| TR (1) | TR199900719A2 (hu) |
| ZA (1) | ZA992407B (hu) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2841900B1 (fr) | 2002-07-08 | 2007-03-02 | Genfit S A | Nouveaux derives de 1,3-diphenylprop-2-en-1-one substitues, preparation et utilisations |
| FR2841784B1 (fr) | 2002-07-08 | 2007-03-02 | Composition a base de derives de 1,3-diphenylprop-2en-1-one substitues, preparation et utilisations | |
| FR2857361B1 (fr) * | 2003-07-08 | 2005-09-09 | Genfit S A | PREPARATION DE DERIVES DE 1,3-DIPHENYPROP-2-¼n-1-one |
| WO2005063774A1 (en) * | 2003-12-22 | 2005-07-14 | Johns Hopkins University | Boronic acid aryl analogs |
| JP2007297283A (ja) * | 2004-07-28 | 2007-11-15 | Santen Pharmaceut Co Ltd | 新規桂皮酸関連化合物 |
| ES2425965T3 (es) * | 2006-08-30 | 2013-10-18 | The Regents Of The University Of Michigan | Nuevos inhibidores de moléculas pequeñas de MDM2 y usos de los mismos |
| JP2010504298A (ja) * | 2006-09-21 | 2010-02-12 | エフ．ホフマン−ラ ロシュ アーゲー | オキシンドール誘導体 |
| US7638548B2 (en) * | 2006-11-09 | 2009-12-29 | Hoffmann-La Roche Inc. | Spiroindolinone derivatives |
| US7553833B2 (en) * | 2007-05-17 | 2009-06-30 | Hoffmann-La Roche Inc. | 3,3-spiroindolinone derivatives |
| US7928233B2 (en) | 2009-02-10 | 2011-04-19 | Hoffmann-La Roche Inc. | Spiroindolinone pyridine derivatives |
| US8217051B2 (en) | 2009-02-17 | 2012-07-10 | Hoffmann-La Roche Inc. | Spiroindolinone derivatives |
| US8076482B2 (en) | 2009-04-23 | 2011-12-13 | Hoffmann-La Roche Inc. | 3,3′-spiroindolinone derivatives |
| US8017607B2 (en) | 2009-10-14 | 2011-09-13 | Hoffmann-La Roche Inc. | N-substituted-pyrrolidines as inhibitors of MDM2-P-53 interactions |
| US8088815B2 (en) | 2009-12-02 | 2012-01-03 | Hoffman-La Roche Inc. | Spiroindolinone pyrrolidines |
| US8288431B2 (en) | 2010-02-17 | 2012-10-16 | Hoffmann-La Roche Inc. | Substituted spiroindolinones |
| US8217044B2 (en) | 2010-04-28 | 2012-07-10 | Hoffmann-La Roche Inc. | Spiroindolinone pyrrolidines |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3255241A (en) * | 1961-01-19 | 1966-06-07 | Merck & Co Inc | (2-alkylidene acyl)phenoxy-and (2-alkylidene acyl)phenylmercaptocarboxylic acids |
| NL300456A (hu) * | 1962-11-13 | |||
| US3251064A (en) * | 1962-11-13 | 1966-05-10 | Everett M Schultz | beta-aminoacylphenoxy-and beta-aminoacylphenylmercapto-derivatives of monocarboxylicacids |
| US3994955A (en) * | 1975-01-20 | 1976-11-30 | G. D. Searle & Co. | Substituted phenoxydialkylacetic acids and esters |
| US4904697A (en) * | 1987-04-09 | 1990-02-27 | Merrell Dow Pharmaceuticals Inc. | Controlling the growth of certain tumor tissue with chalcone derivatives |
| JPH0624975A (ja) * | 1992-05-12 | 1994-02-01 | Dainippon Ink & Chem Inc | 制癌活性増強剤 |
| DE4327365A1 (de) * | 1993-08-14 | 1995-02-16 | Boehringer Mannheim Gmbh | Verwendung von Phenolen und Phenolderivaten als Arzneimittel mit fibrinogensenkender Wirkung |
-
1998
- 1998-03-30 EP EP98105726A patent/EP0947511A1/en not_active Withdrawn
-
1999
- 1999-03-26 ID IDP990274D patent/ID22335A/id unknown
- 1999-03-26 CA CA002267047A patent/CA2267047A1/en not_active Abandoned
- 1999-03-26 TR TR1999/00719A patent/TR199900719A2/xx unknown
- 1999-03-26 MA MA25510A patent/MA26616A1/fr unknown
- 1999-03-26 NZ NZ334874A patent/NZ334874A/xx unknown
- 1999-03-26 AR ARP990101366A patent/AR018170A1/es unknown
- 1999-03-26 IL IL12919199A patent/IL129191A0/xx unknown
- 1999-03-26 PE PE1999000244A patent/PE20000341A1/es not_active Application Discontinuation
- 1999-03-27 SG SG9901555A patent/SG81972A1/en unknown
- 1999-03-29 BR BR9901208-1A patent/BR9901208A/pt not_active Application Discontinuation
- 1999-03-29 HR HR98105726.8A patent/HRP990093A2/hr not_active Application Discontinuation
- 1999-03-29 KR KR1019990010823A patent/KR19990078366A/ko not_active Application Discontinuation
- 1999-03-29 HU HU9900804A patent/HUP9900804A3/hu unknown
- 1999-03-29 ZA ZA9902407A patent/ZA992407B/xx unknown
- 1999-03-29 PL PL99332273A patent/PL332273A1/xx unknown
- 1999-03-29 NO NO991526A patent/NO991526L/no not_active Application Discontinuation
- 1999-03-30 CN CN99104509A patent/CN1232028A/zh active Pending
- 1999-03-30 JP JP11087932A patent/JP2000063340A/ja active Pending
- 1999-03-30 AU AU22502/99A patent/AU2250299A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BR9901208A (pt) | 2000-04-25 |
| NO991526L (no) | 1999-10-01 |
| NO991526D0 (no) | 1999-03-29 |
| IL129191A0 (en) | 2000-02-17 |
| CN1232028A (zh) | 1999-10-20 |
| EP0947511A1 (en) | 1999-10-06 |
| HU9900804D0 (en) | 1999-05-28 |
| KR19990078366A (ko) | 1999-10-25 |
| JP2000063340A (ja) | 2000-02-29 |
| SG81972A1 (en) | 2001-07-24 |
| NZ334874A (en) | 2000-08-25 |
| AR018170A1 (es) | 2001-10-31 |
| ID22335A (id) | 1999-09-30 |
| HUP9900804A3 (en) | 2001-08-28 |
| PE20000341A1 (es) | 2000-05-08 |
| HRP990093A2 (en) | 2000-02-29 |
| TR199900719A2 (xx) | 1999-10-21 |
| ZA992407B (en) | 1999-09-30 |
| PL332273A1 (en) | 1999-10-11 |
| MA26616A1 (fr) | 2004-12-20 |
| AU2250299A (en) | 1999-10-14 |
| CA2267047A1 (en) | 1999-09-30 |
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