CA2331526C - Purification of (s,s)-8-benzyl-2,8-diazabicyclo[4.3.o]nonane using l-(+) tartaric acid in alcohol/water solvent mixture - Google Patents
Purification of (s,s)-8-benzyl-2,8-diazabicyclo[4.3.o]nonane using l-(+) tartaric acid in alcohol/water solvent mixture Download PDFInfo
- Publication number
- CA2331526C CA2331526C CA2331526A CA2331526A CA2331526C CA 2331526 C CA2331526 C CA 2331526C CA 2331526 A CA2331526 A CA 2331526A CA 2331526 A CA2331526 A CA 2331526A CA 2331526 C CA2331526 C CA 2331526C
- Authority
- CA
- Canada
- Prior art keywords
- benzyl
- nonane
- diazabicyclo
- process according
- mixture
- 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 87
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims abstract description 77
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 title claims abstract description 64
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 title claims abstract description 42
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 title claims abstract description 41
- 239000001358 L(+)-tartaric acid Substances 0.000 title claims abstract description 39
- 235000011002 L(+)-tartaric acid Nutrition 0.000 title claims abstract description 39
- FEWJPZIEWOKRBE-LWMBPPNESA-N L-(+)-Tartaric acid Natural products OC(=O)[C@@H](O)[C@H](O)C(O)=O FEWJPZIEWOKRBE-LWMBPPNESA-N 0.000 title claims abstract description 39
- 239000011877 solvent mixture Substances 0.000 title claims abstract description 35
- 238000000746 purification Methods 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 55
- 239000000203 mixture Substances 0.000 claims abstract description 53
- AFYZAHZKOFBVLE-UONOGXRCSA-N (4as,7as)-6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@H]1NCCC[C@H]1C1)N1CC1=CC=CC=C1 AFYZAHZKOFBVLE-UONOGXRCSA-N 0.000 claims abstract description 51
- QAPHOFIEVHTDAB-QYDSKQJFSA-N (4as,7as)-6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine;(2r,3r)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O.C([C@H]1NCCC[C@H]1C1)N1CC1=CC=CC=C1 QAPHOFIEVHTDAB-QYDSKQJFSA-N 0.000 claims abstract description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 71
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- AFYZAHZKOFBVLE-KGLIPLIRSA-N (4ar,7ar)-6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C([C@@H]1NCCC[C@@H]1C1)N1CC1=CC=CC=C1 AFYZAHZKOFBVLE-KGLIPLIRSA-N 0.000 claims description 19
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 17
- 239000002904 solvent Substances 0.000 claims description 16
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 12
- 238000001953 recrystallisation Methods 0.000 claims description 10
- 238000010899 nucleation Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- KSCPLKVBWDOSAI-NKWVEPMBSA-N (4as,7as)-2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCC[C@H]2CNC[C@H]21 KSCPLKVBWDOSAI-NKWVEPMBSA-N 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 229940095064 tartrate Drugs 0.000 description 18
- 239000013078 crystal Substances 0.000 description 9
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 7
- DJWOBYLOYYIQRM-UHFFFAOYSA-N 2-benzyl-4,5,6,7-tetrahydro-1h-pyrrolo[3,2-b]pyridine Chemical class C=1C=2NCCCC=2NC=1CC1=CC=CC=C1 DJWOBYLOYYIQRM-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 238000001291 vacuum drying Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- AUONNNVJUCSETH-UHFFFAOYSA-N icosanoyl icosanoate Chemical compound CCCCCCCCCCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCCCCCCCCCC AUONNNVJUCSETH-UHFFFAOYSA-N 0.000 description 2
- FABPRXSRWADJSP-MEDUHNTESA-N moxifloxacin Chemical compound COC1=C(N2C[C@H]3NCCC[C@H]3C2)C(F)=CC(C(C(C(O)=O)=C2)=O)=C1N2C1CC1 FABPRXSRWADJSP-MEDUHNTESA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- QAPHOFIEVHTDAB-DXLMOZQFSA-N (4as,7as)-6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine;(2s,3s)-2,3-dihydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)[C@H](O)C(O)=O.C([C@H]1NCCC[C@H]1C1)N1CC1=CC=CC=C1 QAPHOFIEVHTDAB-DXLMOZQFSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AFYZAHZKOFBVLE-UHFFFAOYSA-N 6-benzyl-1,2,3,4,4a,5,7,7a-octahydropyrrolo[3,4-b]pyridine Chemical compound C1C2CCCNC2CN1CC1=CC=CC=C1 AFYZAHZKOFBVLE-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- 206010067125 Liver injury Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- -1 for example Substances 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229960003702 moxifloxacin Drugs 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19821039.6 | 1998-05-11 | ||
| DE19821039A DE19821039A1 (de) | 1998-05-11 | 1998-05-11 | Verfahren zur Herstellung von (S,S)-Benzyl-2,8-diazabicyclo[4.3.0]nonan |
| PCT/EP1999/002860 WO1999058532A1 (de) | 1998-05-11 | 1999-04-28 | Verfahren zur herstellung von (s,s)-benzyl-2,8-diazabicyclo[4.3.0]nonan |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2331526A1 CA2331526A1 (en) | 1999-11-18 |
| CA2331526C true CA2331526C (en) | 2011-09-13 |
Family
ID=7867389
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2331526A Expired - Lifetime CA2331526C (en) | 1998-05-11 | 1999-04-28 | Purification of (s,s)-8-benzyl-2,8-diazabicyclo[4.3.o]nonane using l-(+) tartaric acid in alcohol/water solvent mixture |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6235908B1 (https=) |
| EP (1) | EP1077979B1 (https=) |
| JP (1) | JP4554076B2 (https=) |
| AR (1) | AR019123A1 (https=) |
| AU (1) | AU3824599A (https=) |
| CA (1) | CA2331526C (https=) |
| CO (1) | CO4830459A1 (https=) |
| DE (2) | DE19821039A1 (https=) |
| ES (1) | ES2245101T3 (https=) |
| PE (1) | PE20000477A1 (https=) |
| SV (1) | SV1999000060A (https=) |
| UY (1) | UY25501A1 (https=) |
| WO (1) | WO1999058532A1 (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU230030B1 (hu) * | 1999-10-08 | 2015-05-28 | Debiopharm International Sa | Fab I inhibitorok |
| US6476046B1 (en) | 2000-12-04 | 2002-11-05 | Sepracor, Inc. | Diazabicyclo[4.3.0]nonanes, and methods of use thereof |
| EP1560584B1 (en) * | 2001-04-06 | 2009-01-14 | Affinium Pharmaceuticals, Inc. | Fab i inhibitors |
| EP1575951B1 (en) * | 2002-12-06 | 2014-06-25 | Debiopharm International SA | Heterocyclic compounds, methods of making them and their use in therapy |
| WO2004082586A2 (en) | 2003-03-17 | 2004-09-30 | Affinium Pharmaceuticals, Inc. | Phamaceutical compositions comprising inhibitors of fab i and further antibiotics |
| DK1828167T3 (da) * | 2004-06-04 | 2014-10-20 | Debiopharm Int Sa | Acrylamidderivater som antibiotiske midler |
| KR20080075027A (ko) * | 2005-12-05 | 2008-08-13 | 아피늄 파마슈티컬스, 인크. | Ｆａｂｉ 억제제 및 항박테리아제로서의헤테로시클릴아크릴아미드 화합물 |
| JP5468899B2 (ja) | 2006-07-20 | 2014-04-09 | アフィニウム ファーマシューティカルズ， インク． | Ｆａｂｉインヒビターとしてのアクリルアミド誘導体 |
| JP2010509305A (ja) * | 2006-11-13 | 2010-03-25 | シプラ・リミテッド | モキシフロキサシン塩酸塩の合成方法 |
| US7692015B2 (en) * | 2007-01-05 | 2010-04-06 | Zheqing Wang | Economical process for preparing (S, S)-2, 8-diazabicyclo[4.3.0]nonane and its enantiomer |
| EP2125802A4 (en) | 2007-02-16 | 2014-08-20 | Debiopharm Int Sa | SALTS, PRODRUGS AND POLYMORPHES OF FAB I INHIBITORS |
| WO2009125425A2 (en) * | 2008-02-08 | 2009-10-15 | Neuland Laboratories Ltd | Improved process for the preparation of (s.s)-2.8-diazabicyclo[4.3.0]nonane |
| IT1393337B1 (it) | 2009-03-06 | 2012-04-20 | Italiana Sint Spa | Sintesi di (4as, 7as)-ottaidro-1h-pirrolo[3,4-b]piridina |
| CN103044418B (zh) * | 2011-10-14 | 2015-02-04 | 上海朴颐化学科技有限公司 | (s,s)-2,8-二氮杂双环[4,3,0]壬烷的不对称合成方法、相关原料及制备方法 |
| AU2013279021C1 (en) | 2012-06-19 | 2017-03-16 | Debiopharm International Sa | Prodrug derivatives of (E)-N-methyl-N-((3-methylbenzofuran-2-yl)methyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide |
| RS61312B1 (sr) | 2016-02-26 | 2021-02-26 | Debiopharm Int Sa | Lek za lečenje infekcija dijabetskog stopala |
| TN2021000159A1 (en) | 2019-02-14 | 2023-04-04 | Debiopharm Int Sa | Afabicin formulation, method for making the same and uses thereof |
| SG11202113174SA (en) | 2019-06-14 | 2021-12-30 | Debiopharm Int Sa | Medicament and use thereof for treating bacterial infections involving biofilm |
| CN112574197B (zh) * | 2020-12-07 | 2021-12-31 | 泰安汉威集团有限公司 | 一种化合物c的手性纯化方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB354975A (en) * | 1929-07-19 | 1931-08-20 | Ig Farbenindustrie Ag | Manufacture of optically active phenylpropanol-methylamines |
| HU194221B (en) * | 1985-04-19 | 1988-01-28 | Richter Gedeon Vegyeszet | Process for preparing novel octahydro-indolo/2,3-a/quinoline derivative and pharmaceutical comprising this compound |
| JPH0285235A (ja) * | 1988-09-22 | 1990-03-26 | Kohjin Co Ltd | 光学活性アミノアルコール類の製法 |
| JP2995704B2 (ja) * | 1989-02-17 | 1999-12-27 | 東京化成工業株式会社 | 光学活性な１ｈ−３−アミノピロリジン化合物の製造法 |
| IT1231158B (it) * | 1989-07-20 | 1991-11-19 | Dompe Farmaceutici Spa | Procedimento per la risoluzione ottica della dropropizina. |
| DE69108743T2 (de) * | 1991-01-31 | 1995-08-17 | Pfizer | Recematspaltung von trans-2-(2-pyrimidinyl)-7-(hydroxymethyl)octahydro-2h-pyrido[1,2-a]-pyrazin. |
| TW209865B (https=) * | 1992-01-10 | 1993-07-21 | Bayer Ag | |
| DE4234078A1 (de) * | 1992-10-09 | 1994-04-14 | Bayer Ag | Chinoloncarbonsäuren |
| DE4234330A1 (de) * | 1992-10-12 | 1994-04-14 | Bayer Ag | Chinoloncarbonsäuren |
| CA2112165C (en) * | 1992-12-25 | 2003-04-08 | Makoto Takemura | Bicyclic amine derivatives |
| US5686614A (en) * | 1995-04-11 | 1997-11-11 | Neurogen Corporation | Preparation of chiral 5-aminocarbonyl-5H-dibenzo a,d!cyclohepten-5,10-imines by optical resolution |
| DE19601745C1 (de) * | 1996-01-19 | 1997-10-09 | Gruenenthal Gmbh | Verfahren zur Racematspaltung von Tramadol |
-
1998
- 1998-05-11 DE DE19821039A patent/DE19821039A1/de not_active Ceased
-
1999
- 1999-04-28 DE DE59912242T patent/DE59912242D1/de not_active Expired - Lifetime
- 1999-04-28 AU AU38245/99A patent/AU3824599A/en not_active Abandoned
- 1999-04-28 CA CA2331526A patent/CA2331526C/en not_active Expired - Lifetime
- 1999-04-28 WO PCT/EP1999/002860 patent/WO1999058532A1/de not_active Ceased
- 1999-04-28 EP EP99920805A patent/EP1077979B1/de not_active Expired - Lifetime
- 1999-04-28 ES ES99920805T patent/ES2245101T3/es not_active Expired - Lifetime
- 1999-04-28 JP JP2000548336A patent/JP4554076B2/ja not_active Expired - Lifetime
- 1999-04-28 US US09/700,107 patent/US6235908B1/en not_active Expired - Lifetime
- 1999-04-30 AR ARP990102026A patent/AR019123A1/es unknown
- 1999-05-07 UY UY25501A patent/UY25501A1/es not_active Application Discontinuation
- 1999-05-10 PE PE1999000379A patent/PE20000477A1/es not_active Application Discontinuation
- 1999-05-10 CO CO99028729A patent/CO4830459A1/es unknown
- 1999-05-11 SV SV1999000060A patent/SV1999000060A/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SV1999000060A (es) | 1999-10-27 |
| US6235908B1 (en) | 2001-05-22 |
| WO1999058532A1 (de) | 1999-11-18 |
| JP4554076B2 (ja) | 2010-09-29 |
| DE59912242D1 (de) | 2005-08-11 |
| EP1077979B1 (de) | 2005-07-06 |
| ES2245101T3 (es) | 2005-12-16 |
| AU3824599A (en) | 1999-11-29 |
| CA2331526A1 (en) | 1999-11-18 |
| PE20000477A1 (es) | 2000-07-07 |
| JP2002514648A (ja) | 2002-05-21 |
| UY25501A1 (es) | 1999-11-17 |
| CO4830459A1 (es) | 1999-08-30 |
| AR019123A1 (es) | 2001-12-26 |
| DE19821039A1 (de) | 1999-11-18 |
| EP1077979A1 (de) | 2001-02-28 |
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