ES2062049T3 - Semicarbazonas sustituidas artropodicidas. - Google Patents

Semicarbazonas sustituidas artropodicidas.

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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
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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
Application number
ES89313369T
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English (en)
Inventor
John Powell Daub
George Philip Lahm
Bradford Senn Marlin
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
EIDP Inc
Original Assignee
EI Du Pont de Nemours and Co
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Application granted granted Critical
Publication of ES2062049T3 publication Critical patent/ES2062049T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D307/00Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77Heterocyclic 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
    • C07D307/78Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/82Benzo [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
    • AHUMAN NECESSITIES
    • A01AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01NPRESERVATION 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
    • A01N47/00Biocides, 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
    • A01N47/08Biocides, 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
    • A01N47/28Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
    • A01N47/34Ureas 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C281/00Derivatives 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
    • C07C281/06Compounds containing any of the groups, e.g. semicarbazides
    • C07C281/08Compounds containing any of the groups, e.g. semicarbazides the other nitrogen atom being further doubly-bound to a carbon atom, e.g. semicarbazones
    • C07C281/12Compounds 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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/04Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
    • C07D311/58Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
    • C07D311/68Benzo[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
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D311/00Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02Heterocyclic 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
    • C07D311/74Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D335/00Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06Benzothiopyrans; Hydrogenated benzothiopyrans
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
    • C07C2602/08One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00Systems containing two condensed rings
    • C07C2602/02Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/04One of the condensed rings being a six-membered aromatic ring
    • C07C2602/10One 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.
ES89313369T 1988-12-27 1989-12-20 Semicarbazonas sustituidas artropodicidas. Expired - Lifetime ES2062049T3 (es)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

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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