ES2062049T3 - Semicarbazonas sustituidas artropodicidas. - Google Patents
Semicarbazonas sustituidas artropodicidas.Info
- Publication number
- ES2062049T3 ES2062049T3 ES89313369T ES89313369T ES2062049T3 ES 2062049 T3 ES2062049 T3 ES 2062049T3 ES 89313369 T ES89313369 T ES 89313369T ES 89313369 T ES89313369 T ES 89313369T ES 2062049 T3 ES2062049 T3 ES 2062049T3
- Authority
- ES
- Spain
- Prior art keywords
- carbons
- substituted semi
- semi
- substituted
- chem
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans 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 carbon atoms of the hetero ring
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/34—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the groups, e.g. biuret; Thio analogues thereof; Urea-aldehyde condensation products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/06—Compounds containing any of the groups, e.g. semicarbazides
- C07C281/08—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
- C07C281/12—Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones the carbon atom being part of a ring other than a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/68—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with nitrogen atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Pest Control & Pesticides (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Grinding And Polishing Of Tertiary Curved Surfaces And Surfaces With Complex Shapes (AREA)
- Finish Polishing, Edge Sharpening, And Grinding By Specific Grinding Devices (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Battery Electrode And Active Subsutance (AREA)
- Photoreceptors In Electrophotography (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Un procedimiento para la preparación de un compuesto de fórmula donde: Q es A es(CH2)t, O,S(O)q, NR7, OCH2 o S(O)qCH2, donde cada carbono puede estar individualmente sustituido con1 o 2 sustituyentes seleccionados entre 1 o 2 halógenos o grupos alquilo C1-6, cicloalquilo C3-6, halocicloalquilo C3-6, alquilcicloalquilo C4-7, alcoxicarbonilo C2-4 o fenilo opcionalmente sustituido con 1 a 3 sustituyentes independientemente seleccionados entre W; R1 y R2 son independientemente R8, halógeno, CN, NO2, N3, SCN, OR8, SR8, SOR8, SO2R8, NR8R9, C(O)R8, CO2R8, C(O)NR8R9, OC(O)R8, OCO2R8, OC(O)NR8R9, NR9C(O)R8, NR9C(O)NR8R9, OSO2R8, NR9SO2R8 o cuando m es 2, los grupos R1 están opcionalmente unidos entre sí para formar un anillo condensado de 5 o 6 miembros como OCH2O, OCH2CH2O oCH2CH2O, cada uno de ellos opcionalmente sustituido con 1 a 4 átomos de halógeno o 1 o 2 grupos metilo o cuando n es 2,los grupos R2 están opcionalmente unidos entre sí para formar un anillo condensado de 5 o 6 miembros como OCH2O, OCH2CH2O oCH2CH2O cada uno de ellos opcionalmente sustituido con 1 a 4 halógenos o 1 o 2 grupos metilo; siendo R2 distinto de CH3 cuando R1, R3 y R4 son H y A es CH2; R3 es H, alquilo C1-6, haloalquilo C1-6, alquilcicloalquilo C4-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, alcoxialquilo C2-6, cianoalquilo C2-6, alcoxicarbonilalquilo C3-8, OR8, S(O)qR8, NR8R9, CN,CO2R8, C(O)R8, C(O)NR8R9, C(S)NR8R9, C(S)R8, C(S)SR8, fenilo opcionalmente sustituido con (R10)p o bencilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W o R3 es cicloalquilo C3-6 opcionalmente sustituido con 1 o 2 halógenoso 1 o 2 grupos metilo; R4 es H, alquilo C1-6, haloalquilo C1-6, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, alcoxialquilo C2-6, cianoalquilo C2-6, fenilo opcionalmente sustituido con (R10)p o bencilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W; R5 y R6 son independientemente H, alquilo C1-22, alcoxialquilo C2-22, alquilcarbonilo C2-22, alcoxicarbonilo C2-22, haloalquilcarbonilo C2-22, haloalcoxicarbonilo C2-22, SR11, CHO, alquilsulfonilo C1-4, fenilsulfonil opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W, fenoxicarbonilo C7-15 opcionalmente sustituido con1 a 3 sustituyentes seleccionados entre W, fenilcarbonilo C7-15 opionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W, C(O)CO2 alquilo C1-4, benciloxicarbonilo C8-12 opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W, o R5 y R6 son independientemente fenil opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W o bencilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W; R7 es H, alquilo C1-4 o fenilo opcionalmente sustituido con W; SR8, SOR8, SO2R8, C(O)R8, CO2R8, C(O)NR8R9, C(S)NR8R9, C(S)R8, C(S)OR8, P(O)(OR8)2, P(S)(OR8)2, P(O)(R8) OR8 o P(O) (R8) SR8; con la condición de que cuando R7 es distinto de COR8, C(O)NR8R9 o C(S)NR8R9, entonces R8 es distinto de H; R8 es H, alquilo C1-6, haloalquilo C1-6, cicloalquilalquilo C4-7, halocicloalquilalquilo C4-7, alquenilo C2-6, haloalquenilo C2-6, alquinilo C2-6, haloalquinilo C2-6, alcoxialquilo C2-6, alquiltioalquilo C2-6, nitroalquilo C1-6, cianoalquilo C2-6, alcoxicarbonilalquilo C3-8, cicloalquilo C3-6, halocicloalquilo C3-6,feniloopcionalmentesustituido con1 a 3 sustituyentesseleccionados independientementeentreW o benciloopcionalmentesustituido con1 a 3 sustituyentesseleccionados independientemente entre W; R9 es H, alquilo C1-4, alquenilo C2-4, alquinilo C2-4 o bienR8 y R9 están opcionalmente unidos entre sí para formar (CH2)4, (CH2)5 o (CH2CH2OCH2CH2); R10 es R8, halógeno, CN, NO2, N3, SCN, OR8, SR8, SOR8, SO2R8, NR8R9, COR8, CO2R8, CONR8R9, SO2NR8R9, OC(O)R8, OCO2R8, OC(O)NR8R9, NR9C(O) R8, NR9C(O) NR8R9, OSO2R8, NR9SO2R8 o cuando p es 2, los grupos R10 están opcionalmente unidos entre sí para formar un anillo condensado de 5 o 6 miembros como OCH2O, OCH2CH2O oCH2CH2O, cada uno de ellos opcionalmente sustituido independientemente con 1 a 4 átomos de halógeno o 1 o2 grupos metilo; R11 es alquilo C1-22, haloalquilo C1-22, fenilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W o R11 es NR12C(O)R13, NR12S(O)aR13, C(O)R13, NR12R16, SR14, ZR14 / NR12P k n Y ZR15 , ZR14 / NR12 P k n Y R15 o OR14 / P k n O OR15 R12 y R16 están seleccionados independientemente entre alquilo C1-6, haloalquilo C1-6, cicloalquilo C3-6, cicloalquilalquilo C4-7, cianoalquilo C2-6, alcoxialquilo C2-6, alcoxicarbonilalquilo C3-8, dialquilaminocarbonilalquilo C4-8, fenilo opcionalmente sustituido con 1 o 2 sustituyentes seleccionados entre W, bencilo opcionalmente sustituido con1 o 2 sustituyentes seleccionados entre W y fenetilo opcionalmente sustituido con 1 o 2 sustituyentes seleccionados entre W o R12 R16 están opcionalmente unidos entre sí para formar (CH2)4, (CH2)5 o (CH2)2O(CH2)2, cada anillo opcionalmente sustituido con 1 o 2 grupos metilo; R13 es F, alquilo C1-20, haloalquilo C1-6, dialquilamino C2-8, piperidinilo, pirrolidinilo, morfolinilo o fenilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados entre W o bien R13 es alcoxi C1-20, haloalcoxi C1-6 o alcoxiC1-4 sustituidos con ciano, nitro, alcoxi C1-4, alcoxialcoxi C4-8, alquiltio C1-2, alcoxicarbonilo C2-3, dialquilaminocarbonilo C3-5 o fenilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W o bien R13 es fenoxi opcionalmente sustituido con 1 a 3 sustituyentes seleccionados entre W; R14 y R15 están seleccionados independientemente entre alquilo C1-4, haloalquilo C2-4, fenilo opcionalmente sustituido con 1 a 3 sustituyentes seleccionados independientemente entre W o bien R14 y R15 están opcionalmente unidos entre sí para formar (CH2)2, (CH2)3 o CH2C(CH3)2CH2; W es halógeno, CN, NO2, alquilo C1-2, haloalquilol C1-2, alcoxi C1-2, haloalcoxi C1-2, alquiltio C1-2, haloalquiltio C1-2, alquilsulfonilo C1-2 o haloalquilsulfonilo C1-2; m es 1 a 5; n es 1a 4; t es 0 a 3; q es 0 a 2; p es 1 a 3; a es 0 a 2; V es O os; X es O o S; siendo X = O cuando A es CH2 y R2, R3 y R4 son H; Y es O o Sy Z es O o S; con las condiciones de que: i) cuando R1 es OCO2R8, R8 no es H y ii) cuando R1 es NR8R9 y R8 es haloalquilo C1-6, el sustituyente halógeno no se encuentra en el átomo de carbono adyacente al átomo de nitrógeno. procedimiento que consiste en: (a) hacer reaccionar una hidrazona de fórmula (II) con un isocianato de fórmula (III) Q NHR5 (II) donde Q, R1, myR5 son los definidos anteriormente; o (b) condensar una semicarbazida sustituida con fenilo de fórmula (VI) con una cetona de fórmula (IV) donde R1m R2, R3, R4, R5, m y n son los definidos anteriormente; o (c) hacer reaccionar un compuesto de fórmula (I) donde R5 y R6 son hidrógeno con un reactivo electrófilo para preparar un compuesto de fórmula (I) donde R5 y R6 son distintos de hidrógeno.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US29040488A | 1988-12-27 | 1988-12-27 | |
US43636189A | 1989-11-13 | 1989-11-13 |
Publications (1)
Publication Number | Publication Date |
---|---|
ES2062049T3 true ES2062049T3 (es) | 1994-12-16 |
Family
ID=26966165
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES89313369T Expired - Lifetime ES2062049T3 (es) | 1988-12-27 | 1989-12-20 | Semicarbazonas sustituidas artropodicidas. |
Country Status (17)
Country | Link |
---|---|
EP (2) | EP0452406A1 (es) |
JP (1) | JP2894363B2 (es) |
KR (1) | KR910700231A (es) |
CN (1) | CN1043935A (es) |
AT (1) | ATE102606T1 (es) |
AU (1) | AU632093B2 (es) |
BR (1) | BR8907842A (es) |
DE (1) | DE68913706T2 (es) |
DK (1) | DK121991A (es) |
ES (1) | ES2062049T3 (es) |
HU (1) | HUT58695A (es) |
IL (1) | IL92870A (es) |
NZ (1) | NZ231999A (es) |
PE (1) | PE24491A1 (es) |
RU (1) | RU2067092C1 (es) |
WO (2) | WO1990007495A1 (es) |
YU (1) | YU245589A (es) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5238941A (en) * | 1988-03-25 | 1993-08-24 | Ciba-Geigy Corporation | Arylhydrazones and pharmaceutical compositions thereof |
US5395855A (en) * | 1990-05-07 | 1995-03-07 | Ciba-Geigy Corporation | Hydrazones |
AU645799B2 (en) * | 1990-05-07 | 1994-01-27 | Novartis Ag | Hydrazones |
WO1992003421A2 (en) * | 1990-08-17 | 1992-03-05 | E.I. Du Pont De Nemours And Company | Arthropodicidal pyrazolines, pyrazolidines and hydrazines |
EP0553284A1 (en) * | 1990-10-05 | 1993-08-04 | E.I. Du Pont De Nemours And Company | Semicarbazone arthropodicides |
US5462938A (en) * | 1990-12-21 | 1995-10-31 | Annus; Gary D. | Arthropodicidal oxadiazinyl, thiadiazinyl and triazinyl carboxanilides |
EP0781768B1 (en) * | 1991-05-24 | 2001-11-21 | E.I. Du Pont De Nemours And Company | Arthropodicidal anilides |
US5514678A (en) * | 1992-03-26 | 1996-05-07 | E. I. Du Pont De Nemours And Company | Arthropodicidal 1,2,4-triazinyl amides |
IL105208A0 (en) * | 1992-04-23 | 1993-07-08 | Sumitomo Chemical Co | Hydrazone derivatives,process for producing same,insecticides and/or acaricides containing same as active ingredient and intermediate compounds thereof |
WO1993022289A1 (en) * | 1992-05-06 | 1993-11-11 | E.I. Du Pont De Nemours And Company | Arthropodicidal imidazolidines |
ES2103166B1 (es) * | 1992-08-26 | 1998-04-01 | Ciba Geigy Ag | Procedimiento para la obtencion de amidinohidrazonas biciclicas. |
US5328915A (en) * | 1992-09-17 | 1994-07-12 | E. I. Du Pont De Nemours And Company | Arthropodicidal amidrazone ureas |
AU5299493A (en) * | 1992-10-19 | 1994-05-09 | E.I. Du Pont De Nemours And Company | Arthropodicidal semicarbazones |
AU4953796A (en) * | 1995-03-15 | 1996-10-02 | Sanyko Company, Limited | Dipeptide compounds having ahpba structure |
AU2002952453A0 (en) * | 2002-11-01 | 2002-11-21 | Novogen Research Pty Ltd | Aminated isoflavonoid derivatives and uses thereof |
CN101434595B (zh) * | 2008-12-19 | 2014-06-25 | 沈阳药科大学 | 抗真菌剂-硫色满酮缩氨基(硫)脲系列物 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL31161A (en) * | 1968-01-02 | 1972-08-30 | Bayer Ag | Carbonic acid derivatives of 1,2-dicarbonylphenylhydrazones and their preparation,and their use as pesticides |
GB1314899A (en) * | 1970-07-28 | 1973-04-26 | Sterling Winthrop Group Ltd | Thiosemicarbazones processes for their preparations and compositions incorporating them |
BE795111A (fr) * | 1972-02-09 | 1973-08-07 | Philips Nv | Composes de benzylidene-semicarbazide et leur activite insecticide |
US3920437A (en) * | 1973-03-09 | 1975-11-18 | Stauffer Chemical Co | Biocidal active carbamyl hydrazones |
NZ189705A (en) * | 1978-03-01 | 1981-07-13 | Boots Co Ltd | Benzophenone-hydrazone derivatives and pesticidal compositions intermediates |
EP0026040B1 (en) * | 1979-08-31 | 1985-03-13 | Fbc Limited | Substituted benzophenone hydrazones, pesticidal compositions containing them and method of combating pests |
JPS5829297B2 (ja) * | 1981-08-14 | 1983-06-22 | 北興化学工業株式会社 | ベンゾイルヒドラゾン誘導体および殺虫剤 |
DE3624349A1 (de) * | 1986-07-17 | 1988-01-28 | Schering Ag | Substituierte hydrazone, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
-
1989
- 1989-12-20 WO PCT/US1989/005597 patent/WO1990007495A1/en not_active Application Discontinuation
- 1989-12-20 BR BR898907842A patent/BR8907842A/pt not_active Application Discontinuation
- 1989-12-20 HU HU901521A patent/HUT58695A/hu unknown
- 1989-12-20 RU SU894895829A patent/RU2067092C1/ru active
- 1989-12-20 ES ES89313369T patent/ES2062049T3/es not_active Expired - Lifetime
- 1989-12-20 AT AT89313369T patent/ATE102606T1/de not_active IP Right Cessation
- 1989-12-20 EP EP90902098A patent/EP0452406A1/en active Pending
- 1989-12-20 AU AU50246/90A patent/AU632093B2/en not_active Ceased
- 1989-12-20 DE DE68913706T patent/DE68913706T2/de not_active Expired - Fee Related
- 1989-12-20 EP EP89313369A patent/EP0377304B1/en not_active Expired - Lifetime
- 1989-12-23 CN CN89109410A patent/CN1043935A/zh active Pending
- 1989-12-25 IL IL9287089A patent/IL92870A/en not_active IP Right Cessation
- 1989-12-26 PE PE1989163237A patent/PE24491A1/es unknown
- 1989-12-26 YU YU02455/89A patent/YU245589A/xx unknown
-
1990
- 1990-01-04 NZ NZ231999A patent/NZ231999A/en unknown
- 1990-06-20 WO PCT/US1990/003347 patent/WO1991007382A1/en unknown
- 1990-06-20 JP JP2515832A patent/JP2894363B2/ja not_active Expired - Fee Related
- 1990-08-27 KR KR1019900701910A patent/KR910700231A/ko not_active Application Discontinuation
-
1991
- 1991-06-21 DK DK121991A patent/DK121991A/da unknown
Also Published As
Publication number | Publication date |
---|---|
CN1043935A (zh) | 1990-07-18 |
PE24491A1 (es) | 1991-08-22 |
IL92870A0 (en) | 1990-09-17 |
EP0377304A2 (en) | 1990-07-11 |
AU5024690A (en) | 1990-08-01 |
JP2894363B2 (ja) | 1999-05-24 |
YU245589A (en) | 1991-06-30 |
ATE102606T1 (de) | 1994-03-15 |
RU2067092C1 (ru) | 1996-09-27 |
BR8907842A (pt) | 1991-12-03 |
DK121991D0 (da) | 1991-06-21 |
WO1990007495A1 (en) | 1990-07-12 |
WO1991007382A1 (en) | 1991-05-30 |
IL92870A (en) | 1994-05-30 |
EP0377304A3 (en) | 1990-07-25 |
EP0452406A1 (en) | 1991-10-23 |
JPH05501556A (ja) | 1993-03-25 |
DE68913706T2 (de) | 1994-08-04 |
EP0377304B1 (en) | 1994-03-09 |
HUT58695A (en) | 1992-03-30 |
KR910700231A (ko) | 1991-03-14 |
AU632093B2 (en) | 1992-12-17 |
DK121991A (da) | 1991-06-21 |
NZ231999A (en) | 1992-08-26 |
DE68913706D1 (de) | 1994-04-14 |
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