SI9011710B - 13-alkil-23-imino in 13-halo-23-imino derivati makrolidnih spojin - Google Patents

13-alkil-23-imino in 13-halo-23-imino derivati makrolidnih spojin Download PDF

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Publication number
SI9011710B
SI9011710B SI9011710A SI9011710A SI9011710B SI 9011710 B SI9011710 B SI 9011710B SI 9011710 A SI9011710 A SI 9011710A SI 9011710 A SI9011710 A SI 9011710A SI 9011710 B SI9011710 B SI 9011710B
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Slovenia
Prior art keywords
alkyl
hydrogen
methyl
isopropyl
ethyl
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SI9011710A
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SI9011710A (sl
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Brian Lee Buckwalter
Shin-Shyong Tseng
Timothy Claude Barden
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American Cyanamid Company
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Priority claimed from US07/405,808 external-priority patent/US5030650A/en
Priority claimed from US07/455,686 external-priority patent/US5055486A/en
Application filed by American Cyanamid Company filed Critical American Cyanamid Company
Publication of SI9011710A publication Critical patent/SI9011710A/sl
Publication of SI9011710B publication Critical patent/SI9011710B/sl

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    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D493/00Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/22Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H19/00Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
    • C07H19/01Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
    • 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
    • A01N43/00Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/90Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00Antiparasitic agents
    • A61P33/10Anthelmintics

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Pest Control & Pesticides (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Agronomy & Crop Science (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Saccharide Compounds (AREA)

Claims (8)

1 American Cynamid Company One Cynamid Plaza Wayne, NJ 07470-8426 USA 13-alkil-23-imino in 13-halo-23-imino derivati spojin LL-F28249 in kot endo in ektoparaziticidna insekticidna, akaricidna in nematocidna sredstva PATENTNI ZAHTEVKI 1. Spojina značilna po tem, da ima formulo: W
kj er: Ri je metil, etil ali izopropil; R7 je vodik in R8 je 0R2, ali kadar sta vzeta skupaj z ogljikovim atomom na katerega sta vezana R7 in Re predstavljata C=0; 2 R2 je vodik, Cx-C4 alkil ali O II C —R4 ; R4 je vodik, Ci-C4 alkil, C1-C4 haloalkil, Ci-C4 alkoksi, fenoksi, Cx-C4 alkoksimetil, fenoksimetil ali fenil, neobvezno substituiran z 1 nitro, 1-3 halogeni, 1-3 Ci~C4 alkilom, ali 1-3 Ci-C4 alkoksi; R3 je vodik metil ali etil; X je fluor, brom, klor ali jod; W je =N-Y; Y je OR5 or NHR6; R5 je Ci-C4 alkil ali Ci-C4 acil; R6 je Ci-C4 acil; in črtkana linija, ki tvori trikotnik s kisikom pri C26—č27 pomeni, da je prisotna ali dvojna vez ali epoksid.
2. Spojina po zahtevku 1, značilna po tem, da je Ri izopropil; R7 je vodik in R8 je 0R2; R2 je vodik, Ci-C4 alkil ali 0 II C R 4 r R4 je vodik, metil, klorometil, diklorometil, triklorometil ali metoksimetil R3 je metil; X je fluor W je Ν-Υ; Y je OR5; in R5 je Ci-C4 alkil. 3
3. Metoda zaščite pridelka, dreves, grmičevja, vskladiščenih zrn in okrasnih rastlin pred insekti, akaridi in nematodi, značilna po tem, da na omenjene pridelke, drevesa, grmičevje, vskladiščena zrna in okrasnihe rastline apliciramo insekticidno, akaricidno ali nematocidno učinkovito količino spojino s formulo po zahtevku 1.
4. Metoda po zahtevku 3, značilna po tem, da ima spojina formulo po spodnjem zahtevku 6 in da: Ri je izopropil; R7 je vodik; R8 je 0R2; R2 je vodik, C1-C4 alkil, ali 0 II C R 4 / R4 je vodik, metil, klorometil, diklorometil, triklorometil ali metoksimetil R3 je metil; X je fluor W je Ν-Υ; Y je 0R5; in R5 je Ci-C4 alkil.
5. Sestavek za nadzor endo- in ektoparazitov, insektov, akaridov in nematodov, značilen po tem, da obsega agronomsko sprejemljiv nosilec, ki vsebuje profilaktično, terapevtsko, farmacevtsko ali insekticidno učinkovito količino spojine s formulo po zahtevku 1. 4 r « • ·
6. Spojina, značilna po tem da ima strukturno formulo: X
kj er: Ri je C1-C4 alkil; R2 je vodik metil ali etil R3 je vodik, C1-C4 alkil, ali 0 tl c—r5 ; Rs je vodik, C1-C4 alkil, C1-C4 haloalkil, C1-C4 alkoksi, fenoksi, C1-C4 alkoksimetil, fenoksimetil ali fenil, neobvezno substituiran z 1 nitro, 1-3 halogeni, 1-3 C1-C4 alkil, ali 1-3 C1-C4 alkoksi; R4 je metil, etil ali izopropil; X je kisik, NOR6 ali N-NHR7; R6 je vodik, C1-C4 alkil, C1-C4 alkoksimetil, C1-C4 alkanoil, benzil ali fenil; in R7 je C1-C4 acil, C1-C4 alkil ali benzoil. 5 r. m · · · r e f, f # 9 i* c * β · • « c · ·. · e r- · • r r * r r r c
7. Spojina po zahtevku 6, značilna po tem, da je Ri metil, etil ali izopropil; R.2 metil; R3 je vodik, C1-C4 alkil, ali 0 II c—r5 ; R5 je vodik, Cx-C4 alkoksimetil, C1-C4 halometil ali formil; R4 je izopropil; X je N0R6,' in R6 je C1-C4 alkil.
8. Sestavek za nadzor endo- in ektoparazitov, insektov, akaridov in nematodov, značilen po tem, da obsega agronomsko sprejemljiv nosilec, ki vsebuje profilaktično, terapevtsko, farmacevtsko ali insekticidno učinkovito količino spojine po zahtevku 6. American Cynamid Company One Cynamid Plaza Wayne, NJ 07470-8426
SI9011710A 1989-09-11 1990-09-10 13-alkil-23-imino in 13-halo-23-imino derivati makrolidnih spojin SI9011710B (sl)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US07/405,808 US5030650A (en) 1989-09-11 1989-09-11 13-halo-23-imino derivatives of LL-F28249 compounds and their use as endo- and ectoparasiticidal, insecticidal, acaricidal and nematocidal agents
US07/455,686 US5055486A (en) 1989-12-22 1989-12-22 13-alkyl-23-imino derivative of LL-F28249 compounds and their use as endo- and ectoparasiticidal, insecticidal, acaricidal and nematocidal agents
YU171090A YU47592B (sh) 1989-09-11 1990-09-10 13-alkil-23-imino i 13-halo-23-imino derivati makrolidnih jedinjenja

Publications (2)

Publication Number Publication Date
SI9011710A SI9011710A (sl) 1998-02-28
SI9011710B true SI9011710B (sl) 2000-12-31

Family

ID=27019245

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Application Number Title Priority Date Filing Date
SI9011710A SI9011710B (sl) 1989-09-11 1990-09-10 13-alkil-23-imino in 13-halo-23-imino derivati makrolidnih spojin

Country Status (21)

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EP (1) EP0423445B1 (sl)
JP (1) JP3026827B2 (sl)
KR (2) KR0160972B1 (sl)
CN (2) CN1032004C (sl)
AT (1) ATE130006T1 (sl)
AU (1) AU631454B2 (sl)
BG (1) BG60271B1 (sl)
BR (1) BR9004494A (sl)
DE (1) DE69023454T2 (sl)
DK (1) DK0423445T3 (sl)
ES (1) ES2081880T3 (sl)
GR (1) GR3018033T3 (sl)
HU (1) HU217357B (sl)
IE (1) IE71210B1 (sl)
IL (1) IL109791A (sl)
PL (1) PL164168B1 (sl)
PT (1) PT95241B (sl)
RU (1) RU2070885C1 (sl)
SI (1) SI9011710B (sl)
UA (1) UA41246C2 (sl)
YU (1) YU47592B (sl)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4988824A (en) * 1989-09-11 1991-01-29 Maulding Donald R Process for the preparation of 23-(C1-C6 alkyloxime)-LL-F28249 compounds
US5229416A (en) * 1992-04-29 1993-07-20 Merck & Co., Inc. Avermectin difluoro derivatives
DE19654079A1 (de) 1996-12-23 1998-06-25 Bayer Ag Endo-ekto-parasitizide Mittel
DE102004053964A1 (de) 2004-11-09 2006-05-11 Bayer Healthcare Ag Mittel gegen Demodikose
CN106831811B (zh) * 2015-08-12 2018-10-26 内蒙古佳瑞米精细化工有限公司 一种制备高含量尼莫克汀的方法
US20210137960A1 (en) 2018-02-01 2021-05-13 Yale University Compositions and methods for inhibition of nuclear-penetrating antibodies

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0253378A3 (de) * 1986-07-18 1988-03-23 Ciba-Geigy Ag 13Beta-Alkyl-derivate von S541-Antibiotika zur Bekämpfung von Parasiten an Nutztieren und Pflanzen
ES2058082T3 (es) * 1986-09-12 1994-11-01 American Cyanamid Co Derivados 23-oxo (ceto) y 23-imino de compuestos ll-f28249.
US4831016A (en) * 1986-10-31 1989-05-16 Merck & Co., Inc. Reduced avermectin derivatives
US4886829A (en) * 1987-03-06 1989-12-12 American Cyanamid Company 23-Oxo (keto) and 23-imino derivatives of mono- and diepoxy LL-F28249 compounds
US4806527A (en) * 1987-03-16 1989-02-21 Merck & Co., Inc. Avermectin derivatives
US5830875A (en) * 1989-10-30 1998-11-03 Merck & Co., Inc. 24-and 25-substituted avermectin and milbemycin derivatives

Also Published As

Publication number Publication date
PT95241A (pt) 1991-06-25
JP3026827B2 (ja) 2000-03-27
BG60271B2 (bg) 1994-03-31
AU6235790A (en) 1991-03-14
PT95241B (pt) 1997-06-30
CN1115600A (zh) 1996-01-31
BR9004494A (pt) 1991-09-10
CN1050193A (zh) 1991-03-27
KR910006491A (ko) 1991-04-29
ATE130006T1 (de) 1995-11-15
KR0168751B1 (ko) 1999-01-15
DK0423445T3 (da) 1995-12-11
CN1053556C (zh) 2000-06-21
JPH03106886A (ja) 1991-05-07
DE69023454T2 (de) 1996-06-05
RU2070885C1 (ru) 1996-12-27
IL109791A (en) 1996-06-18
UA41246C2 (uk) 2001-09-17
ES2081880T3 (es) 1996-03-16
DE69023454D1 (de) 1995-12-14
AU631454B2 (en) 1992-11-26
CN1032004C (zh) 1996-06-12
BG60271B1 (bg) 1994-03-31
SI9011710A (sl) 1998-02-28
PL286823A1 (en) 1991-10-07
KR0160972B1 (ko) 1998-12-01
PL164168B1 (pl) 1994-06-30
YU171090A (sh) 1992-12-21
EP0423445B1 (en) 1995-11-08
HUT54691A (en) 1991-03-28
EP0423445A1 (en) 1991-04-24
IE71210B1 (en) 1997-02-12
HU217357B (hu) 2000-01-28
GR3018033T3 (en) 1996-02-29
IE903274A1 (en) 1991-03-27
YU47592B (sh) 1995-10-24

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