ES2172133T3 - Procedimiento para la obtencion de 2-nitroguanidinas 1,3-disubstituidas. - Google Patents
Procedimiento para la obtencion de 2-nitroguanidinas 1,3-disubstituidas.Info
- Publication number
- ES2172133T3 ES2172133T3 ES98919095T ES98919095T ES2172133T3 ES 2172133 T3 ES2172133 T3 ES 2172133T3 ES 98919095 T ES98919095 T ES 98919095T ES 98919095 T ES98919095 T ES 98919095T ES 2172133 T3 ES2172133 T3 ES 2172133T3
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- atoms
- halogen
- alkyl
- halogen atoms
- 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
- 125000004432 carbon atom Chemical group C* 0.000 abstract 41
- 125000005843 halogen group Chemical group 0.000 abstract 17
- 125000000217 alkyl group Chemical group 0.000 abstract 7
- 229910052736 halogen Inorganic materials 0.000 abstract 6
- 125000003342 alkenyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 4
- 125000000304 alkynyl group Chemical group 0.000 abstract 4
- -1 atoms halogen Chemical group 0.000 abstract 4
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 4
- 125000001188 haloalkyl group Chemical group 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- 125000004414 alkyl thio group Chemical group 0.000 abstract 3
- 125000005336 allyloxy group Chemical group 0.000 abstract 3
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 abstract 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 abstract 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 2
- CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 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
- 125000002619 bicyclic group Chemical group 0.000 abstract 1
- 239000004202 carbamide Substances 0.000 abstract 1
- 125000004802 cyanophenyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000004995 haloalkylthio group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000006501 nitrophenyl group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 239000011593 sulfur Substances 0.000 abstract 1
- 229930192474 thiophene Natural products 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/40—Acylated substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Pyridine Compounds (AREA)
- Furan Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Procedimiento para la obtención de compuestos de la fórmula (I) en la que R1 significa hidrógeno o alquilo con 1 a 4 átomos de carbono, R2 significa hidrógeno, alquilo con 1 a 6 átomos de carbono, cicloalquilo con 3 a 6 átomos de carbono o un resto -CH2R3, R3 significa alquenilo con 2 a 5 átomos de carbono, alquinilo con 2 a 5 átomos de carbono, fenilo, cianofenilo, nitrofenilo, halógenofenilo con 1 a 3 átomos de halógeno, fenilo, 3-piridilo, 5-tiazolilo substituido por alquilo con 1 a 3 átomos de carbono, halógenoalquilo con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, por alcoxi con 1 a 3 átomos de carbono o por halógenoalcoxi con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, 5-tiazolilo substituido por uno o dos substituyentes (preferentemente uno) del grupo formado por alquilo con 1 a 3 átomos de carbono, halógenoalquilo con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, ciclopropilo, halógenociclopropilo con 1 a 3 átomos de halógeno, alquenilo con 2 a 3 átomos de carbono, alquinilo con 2 a 3 átomos de carbono, alcoxi con 1 a 3 átomos de carbono, halógenoalquenilo con 2 a 3 átomos de carbono y halógenoalquinilo con 2 a 3 átomos de carbono con respectivamente 1 a 4 átomos de halógeno, halógenoalcoxi con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, alquiltio con 1 a 3 átomos de carbono, halógenoalquiltio con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, aliloxi, propargiloxi, aliltio, propargiltio, halógenoaliloxi y halógenoalquiltio con respectivamente 1 a 3 átomos de halógeno, halógeno, ciano y nitro; o 3-piridilo substituido por uno a cuatro restos (preferentemente 1 o 2) del grupo formado por halógenoalquilo con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, ciclopropilo, halógenociclopropilo con 1 a 3 átomos de halógeno, alquenilo con 2 a 3 átomos de carbono, alquinilo con 2 a 3 átomos de carbono, halógenoalquenilo con 2 a 3 átomos de carbono y halógenoalquinilo con 2 a 3 átomos de carbono con respectivamente 1 a 4 átomos de halógeno, halógenoalcoxi con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, alquiltio con 1 a 3 átomos de carbono, halógenoalquiltio con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, aliloxi, propargiloxi, aliltio, propargiltio, halógenoaliloxi y halógenoalquiltio con respectivamente 1 a 3 átomos de halógeno, ciano, nitro, alquilo con 1 a 3 átomos de carbono, alcoxi con 1 a 3 átomos de carbono y halógeno. Het significa un resto heterocíclico, monocíclico o bicíclico, aromático o no aromático, insubstituido o substituido, preferentemente de la serie que puede contener 1 o 2 substituyentes del grupo formado por halógenoalquilo con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, ciclopropilo, halógenociclopropilo con 1 a 3 átomos de halógeno, alquenilo con 2 a 3 átomos de carbono, alquinilo con 2 a 3 átomos de carbono, halógenoalquenilo con 2 a 3 átomos de carbono y halógenoalquinilo con 2 a 3 átomos de carbono con respectivamente 1 a 4 átomos de halógeno, halógenoalcoxi con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, alquiltio con 1 a 3 átomos de carbono, halógenoalquiltio con 1 a 3 átomos de carbono con 1 a 7 átomos de halógeno, aliloxi, propargiloxi, aliltio, propargiltio, halógenoaliloxi y halógenoaliltio con respectivamente 1 a 3 átomos de halógeno, ciano, nitro, alquilo con 1 a 3 átomos de carbono, alcoxi con 1 a 3 átomos de carbono y halógeno, caracterizado porque se hace reaccionar un compuesto de la fórmula (II) en la que R1, R2 y Het tienen los significados anteriormente indicados y R4 significa alquilo con 1 a 10 átomos de carbono, cicloalquilo con 3 a 6 átomos de carbono, fenilo, bencilo o heterociclilmetilo respectivamente substituidos o insubstituidos, significando heterociclilo un heterociclo con 5 o 6 miembros insaturado o saturado con 1 o 2 heteroátomos (preferentemente 1), de la serie formada por nitrógeno, oxígeno y azufre tal como por ejemplo furano, tetrahidrofurano, tiofeno o piridina, en presencia de un diluyente, con urea.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712411A DE19712411A1 (de) | 1997-03-25 | 1997-03-25 | Verfahren zur Herstellung von 1,3-disubstituierten 2-Nitroguanidinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2172133T3 true ES2172133T3 (es) | 2002-09-16 |
Family
ID=7824508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES98919095T Expired - Lifetime ES2172133T3 (es) | 1997-03-25 | 1998-03-13 | Procedimiento para la obtencion de 2-nitroguanidinas 1,3-disubstituidas. |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6194575B1 (es) |
| EP (1) | EP0971907B1 (es) |
| JP (1) | JP4231556B2 (es) |
| KR (1) | KR100528637B1 (es) |
| CN (1) | CN1084738C (es) |
| AT (1) | ATE213734T1 (es) |
| AU (1) | AU7206898A (es) |
| BR (1) | BR9808047B1 (es) |
| DE (2) | DE19712411A1 (es) |
| DK (1) | DK0971907T3 (es) |
| ES (1) | ES2172133T3 (es) |
| HK (1) | HK1027560A1 (es) |
| HU (1) | HU222622B1 (es) |
| IL (1) | IL131513A (es) |
| WO (1) | WO1998042690A1 (es) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010041996A (ko) * | 1998-03-19 | 2001-05-25 | 한스 루돌프 하우스, 헨리테 브룬너, 베아트리체 귄터 | 니트로구아니딘 유도체의 제조 방법 |
| DE19961604A1 (de) | 1999-12-21 | 2001-07-05 | Bayer Ag | Verfahren zur Herstellung von 1,3-disubstituierten 2-Nitroguanidinen |
| DE10121652A1 (de) * | 2001-05-03 | 2002-11-07 | Bayer Ag | Verfahren zur Herstellung von 1,3-disubstituierten 2-Nitroguanidinen |
| DE102004056626A1 (de) | 2004-11-24 | 2006-06-01 | Bayer Cropscience Ag | Substituierte Oxyguanidine |
| US9745274B2 (en) | 2013-07-03 | 2017-08-29 | Shin Nippon Biomedical Laboratories, Ltd. | Compound, organic cation transporter 3 detection agent, and organic cation transporter 3 activity inhibitor |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4221802A (en) | 1972-02-03 | 1980-09-09 | Smith Kline & French Laboratories Limited | Pharmacologically active guanidine compounds for inhibiting H-2 histamine receptors |
| US4804780A (en) | 1982-12-20 | 1989-02-14 | American Cyanamid Company | Substituted nitro and cyanoguanidines |
| JP2779403B2 (ja) | 1988-11-29 | 1998-07-23 | 日本バイエルアグロケム株式会社 | 殺虫性ニトロ化合物 |
| IE960442L (en) | 1988-12-27 | 1990-06-27 | Takeda Chemical Industries Ltd | Guanidine derivatives, their production and insecticides |
| DK0383091T3 (da) | 1989-02-13 | 1994-02-07 | Bayer Agrochem Kk | Insecticidt virksomme nitroforbindelser |
| JP2610988B2 (ja) * | 1989-03-09 | 1997-05-14 | 日本バイエルアグロケム 株式会社 | 新規ヘテロ環式化合物及び殺虫剤 |
| AU628229B2 (en) | 1989-11-10 | 1992-09-10 | Agro-Kanesho Co. Ltd. | Hexahydrotriazine compounds and insecticides |
| JPH0674249B2 (ja) | 1990-04-05 | 1994-09-21 | アグロカネショウ株式会社 | 置換ニトログアニジン類の製造法 |
| IL99576A0 (en) * | 1990-10-05 | 1992-08-18 | Ciba Geigy Ag | Triazacyclohexane derivatives |
| TW198724B (es) | 1990-10-24 | 1993-01-21 | Ciba Geigy Ag | |
| DE19611654A1 (de) | 1996-03-25 | 1997-10-02 | Bayer Ag | Verfahren zur Herstellung von N-Methyl-N'-nitroguanidin |
-
1997
- 1997-03-25 DE DE19712411A patent/DE19712411A1/de not_active Withdrawn
-
1998
- 1998-03-13 DE DE59803194T patent/DE59803194D1/de not_active Expired - Lifetime
- 1998-03-13 US US09/381,669 patent/US6194575B1/en not_active Expired - Lifetime
- 1998-03-13 CN CN98803614A patent/CN1084738C/zh not_active Expired - Lifetime
- 1998-03-13 AU AU72068/98A patent/AU7206898A/en not_active Abandoned
- 1998-03-13 DK DK98919095T patent/DK0971907T3/da active
- 1998-03-13 HU HU0001513A patent/HU222622B1/hu not_active IP Right Cessation
- 1998-03-13 EP EP98919095A patent/EP0971907B1/de not_active Expired - Lifetime
- 1998-03-13 JP JP54482298A patent/JP4231556B2/ja not_active Expired - Lifetime
- 1998-03-13 ES ES98919095T patent/ES2172133T3/es not_active Expired - Lifetime
- 1998-03-13 WO PCT/EP1998/001456 patent/WO1998042690A1/de active IP Right Grant
- 1998-03-13 BR BRPI9808047-4A patent/BR9808047B1/pt not_active IP Right Cessation
- 1998-03-13 KR KR10-1999-7007782A patent/KR100528637B1/ko not_active IP Right Cessation
- 1998-03-13 AT AT98919095T patent/ATE213734T1/de not_active IP Right Cessation
- 1998-03-13 IL IL13151398A patent/IL131513A/en not_active IP Right Cessation
-
2000
- 2000-10-17 HK HK00106575A patent/HK1027560A1/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CN1251096A (zh) | 2000-04-19 |
| ATE213734T1 (de) | 2002-03-15 |
| JP2001518106A (ja) | 2001-10-09 |
| EP0971907B1 (de) | 2002-02-27 |
| HUP0001513A2 (hu) | 2000-08-28 |
| JP4231556B2 (ja) | 2009-03-04 |
| BR9808047B1 (pt) | 2010-07-27 |
| HU222622B1 (hu) | 2003-09-29 |
| IL131513A0 (en) | 2001-01-28 |
| EP0971907A1 (de) | 2000-01-19 |
| IL131513A (en) | 2004-08-31 |
| US6194575B1 (en) | 2001-02-27 |
| DE59803194D1 (de) | 2002-04-04 |
| AU7206898A (en) | 1998-10-20 |
| DK0971907T3 (da) | 2002-06-10 |
| DE19712411A1 (de) | 1998-10-01 |
| KR20000075714A (ko) | 2000-12-26 |
| KR100528637B1 (ko) | 2005-11-16 |
| BR9808047A (pt) | 2000-03-08 |
| WO1998042690A1 (de) | 1998-10-01 |
| HUP0001513A3 (en) | 2000-11-28 |
| CN1084738C (zh) | 2002-05-15 |
| HK1027560A1 (en) | 2001-01-19 |
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