IL108306A - DE-O-(alpha-oleandrosyl)-5-demethoxy-avermectin-5-oximes their preparation and pharmaceutical antiparasitic compounds containing them - Google Patents

DE-O-(alpha-oleandrosyl)-5-demethoxy-avermectin-5-oximes their preparation and pharmaceutical antiparasitic compounds containing them

Info

Publication number: IL108306A
Authority: IL; Israel
Prior art keywords: monosaccharide; compound; dihydroavermectin; cyclohexyl; oximino
Prior art date: 1993-01-18

Application number

IL10830694A

Other languages

English (en)

Other versions

IL108306A0 (en

Original Assignee

Pfizer

Priority date (The priority date 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 date listed.)

1993-01-18

Filing date

1994-01-10

Publication date

1998-08-16

1994-01-10 Application filed by Pfizer filed Critical Pfizer

1994-04-12 Publication of IL108306A0 publication Critical patent/IL108306A0/xx

1998-08-16 Publication of IL108306A publication Critical patent/IL108306A/en

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 99
239000003096 antiparasitic agent Substances 0.000 title claims abstract description 6
238000002360 preparation method Methods 0.000 title claims description 8
230000002141 anti-parasite Effects 0.000 title abstract description 4
238000001727 in vivo Methods 0.000 claims abstract description 10
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims abstract description 3
150000002772 monosaccharides Chemical class 0.000 claims description 69
239000000203 mixture Substances 0.000 claims description 33
-1 t-butyloxycarbonyl Chemical group 0.000 claims description 26
238000000034 method Methods 0.000 claims description 20
239000005660 Abamectin Substances 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 8
229940125687 antiparasitic agent Drugs 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
238000011321 prophylaxis Methods 0.000 claims description 2
239000003814 drug Substances 0.000 claims 2
208000006004 Flea Infestations Diseases 0.000 claims 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
125000006253 t-butylcarbonyl group Chemical group [H]C([H])([H])C(C(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
238000011282 treatment Methods 0.000 claims 1
229920006395 saturated elastomer Polymers 0.000 abstract description 7
125000002252 acyl group Chemical group 0.000 abstract description 2
125000005843 halogen group Chemical group 0.000 abstract description 2
125000005646 oximino group Chemical group 0.000 abstract description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 3
125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
239000005864 Sulphur Substances 0.000 abstract 1
125000004430 oxygen atom Chemical group O* 0.000 abstract 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 78
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 40
239000000243 solution Substances 0.000 description 31
239000000377 silicon dioxide Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 23
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
238000001819 mass spectrum Methods 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
239000000843 powder Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
BJDCWCLMFKKGEE-CMDXXVQNSA-N chembl252518 Chemical compound C([C@@](OO1)(C)O2)C[C@H]3[C@H](C)CC[C@@H]4[C@@]31[C@@H]2O[C@H](O)[C@@H]4C BJDCWCLMFKKGEE-CMDXXVQNSA-N 0.000 description 11
241001465754 Metazoa Species 0.000 description 10
RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical class C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 10
238000004128 high performance liquid chromatography Methods 0.000 description 10
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 9
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239000012043 crude product Substances 0.000 description 8
238000009472 formulation Methods 0.000 description 8
239000000463 material Substances 0.000 description 8
GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 8
239000012044 organic layer Substances 0.000 description 8
239000000047 product Substances 0.000 description 8
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
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238000006243 chemical reaction Methods 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
229910052943 magnesium sulfate Inorganic materials 0.000 description 6
235000019341 magnesium sulphate Nutrition 0.000 description 6
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 5
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238000004587 chromatography analysis Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
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125000004432 carbon atom Chemical group C* 0.000 description 4
229940093499 ethyl acetate Drugs 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
238000000855 fermentation Methods 0.000 description 4
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NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 4
244000045947 parasite Species 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
241000238421 Arthropoda Species 0.000 description 3
241000282472 Canis lupus familiaris Species 0.000 description 3
241000607479 Yersinia pestis Species 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
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239000001257 hydrogen Substances 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
241000894007 species Species 0.000 description 3
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YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 2
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241000282326 Felis catus Species 0.000 description 2
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
241000244206 Nematoda Species 0.000 description 2
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
241000258242 Siphonaptera Species 0.000 description 2
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GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000037396 body weight Effects 0.000 description 2
239000002775 capsule Substances 0.000 description 2
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
125000001589 carboacyl group Chemical group 0.000 description 2
239000013078 crystal Substances 0.000 description 2
150000002016 disaccharides Chemical class 0.000 description 2
244000078703 ectoparasite Species 0.000 description 2
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208000015181 infectious disease Diseases 0.000 description 2
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HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
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238000002156 mixing Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
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125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
210000000056 organ Anatomy 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000003544 oxime group Chemical group 0.000 description 1
150000002923 oximes Chemical class 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
244000144977 poultry Species 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FMBOFMNHMFFBBD-UHFFFAOYSA-N pyridine-3-carbohydrazide;dihydrochloride Chemical compound Cl.Cl.NNC(=O)C1=CC=CN=C1 FMBOFMNHMFFBBD-UHFFFAOYSA-N 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002453 shampoo Substances 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000005017 substituted alkenyl group Chemical group 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000012049 topical pharmaceutical composition Substances 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/01—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing oxygen
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
General Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Molecular Biology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Tropical Medicine & Parasitology (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL10830694A 1993-01-18 1994-01-10 DE-O-(alpha-oleandrosyl)-5-demethoxy-avermectin-5-oximes their preparation and pharmaceutical antiparasitic compounds containing them IL108306A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB939300883A GB9300883D0 (en)	1993-01-18	1993-01-18	Antiparasitic agents

Publications (2)

Publication Number	Publication Date
IL108306A0 IL108306A0 (en)	1994-04-12
IL108306A true IL108306A (en)	1998-08-16

Family

ID=10728869

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10830694A IL108306A (en)	1993-01-18	1994-01-10	DE-O-(alpha-oleandrosyl)-5-demethoxy-avermectin-5-oximes their preparation and pharmaceutical antiparasitic compounds containing them

Country Status (35)

Country	Link
EP (1)	EP0677054B1 (fr)
JP (1)	JP2732548B2 (fr)
KR (1)	KR0185480B1 (fr)
CN (1)	CN1043768C (fr)
AP (1)	AP522A (fr)
AT (1)	ATE164586T1 (fr)
AU (1)	AU679033B2 (fr)
BR (2)	BR9405811A (fr)
CA (1)	CA2152819C (fr)
CZ (1)	CZ284849B6 (fr)
DE (2)	DE10075003I1 (fr)
DK (1)	DK0677054T3 (fr)
EG (1)	EG20582A (fr)
ES (1)	ES2113639T3 (fr)
FI (1)	FI111727B (fr)
GB (1)	GB9300883D0 (fr)
GR (1)	GR3026710T3 (fr)
HR (1)	HRP940110B1 (fr)
HU (1)	HU221505B (fr)
IL (1)	IL108306A (fr)
LU (1)	LU90518I2 (fr)
MA (1)	MA23091A1 (fr)
MY (1)	MY141106A (fr)
NL (1)	NL300003I2 (fr)
NO (2)	NO304835B1 (fr)
NZ (1)	NZ259868A (fr)
OA (1)	OA10223A (fr)
PL (1)	PL176733B1 (fr)
RU (1)	RU2125059C1 (fr)
SG (1)	SG45131A1 (fr)
SK (1)	SK282031B6 (fr)
UA (1)	UA42707C2 (fr)
WO (1)	WO1994015944A1 (fr)
YU (1)	YU49169B (fr)
ZA (1)	ZA94310B (fr)

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CN109890209B (zh)	2016-10-06	2021-11-19	先正达参股股份有限公司	杀微生物的噁二唑衍生物
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BR112019020734B1 (pt)	2017-04-05	2023-12-05	Syngenta Participations Ag	Compostos derivados de oxadiazol, composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso dos referidos compostos
BR112019020756B1 (pt)	2017-04-05	2023-11-28	Syngenta Participations Ag	Compostos derivados de oxadiazol microbicidas, composição agroquímica compreendendo os mesmos, método para controlar ou prevenir a infestação de plantas úteis por microrganismos fitopatogênicos e uso desses compostos
BR112019020819B1 (pt)	2017-04-05	2023-12-05	Syngenta Participations Ag	Composto de fórmula (i), composição agroquímica, método para controlar ou prevenir a infestação de plantas úteis por micro-organismos fitopatogênicos e uso de um composto de fórmula (i)
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BR112020000371A2 (pt)	2017-07-12	2020-07-14	Syngenta Participations Ag	derivados de oxadiazol microbiocidas
BR112020000414A2 (pt)	2017-07-12	2020-07-21	Syngenta Participations Ag	derivados de oxadiazol microbicidas
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WO2019053026A1 (fr)	2017-09-13	2019-03-21	Syngenta Participations Ag	Dérivés microbiocides de quinoléine (thio)carboxamide
ES2904910T3 (es)	2017-09-13	2022-04-06	Syngenta Participations Ag	Derivados de quinolina (tio)carboxamida microbiocidas
BR112020004933A2 (pt)	2017-09-13	2020-09-15	Syngenta Participations Ag	derivados microbiocidas de (tio)carboxamida de quinolina
CN111094248A (zh)	2017-09-13	2020-05-01	先正达参股股份有限公司	杀微生物的喹啉(硫代)羧酰胺衍生物
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BR112020004926A2 (pt)	2017-09-13	2020-09-15	Syngenta Participations Ag	derivados de quinolino(tio)carboxamida microbiocidas
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CN112714764A (zh)	2018-07-02	2021-04-27	先正达农作物保护股份公司	作为农用化学杀真菌剂的3-(2-噻吩基)-5-(三氟甲基)-1,2,4-噁二唑衍生物
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GB201812692D0 (en)	2018-08-03	2018-09-19	Syngenta Participations Ag	Microbiocidal compounds
EP3853207B1 (fr)	2018-09-19	2022-10-19	Syngenta Crop Protection AG	Dérivés de carboxamide de quinoline microbiocide
WO2020070132A1 (fr)	2018-10-06	2020-04-09	Syngenta Participations Ag	Dérivés de quinoléine dihydro-(thiazine) oxazine microbiocides
EP3860993B1 (fr)	2018-10-06	2022-08-10	Syngenta Participations Ag	Dérivés de quinoléine dihydro-(thiazine)oxazine microbiocides
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GB201903942D0 (en)	2019-03-22	2019-05-08	Syngenta Crop Protection Ag	Microbiocidal compounds
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CN113924294B (zh)	2019-05-29	2024-12-06	先正达农作物保护股份公司	杀微生物衍生物
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WO2021004968A1 (fr)	2019-07-05	2021-01-14	Syngenta Crop Protection Ag	Dérivés de picolinamide microbiocides
GB201910037D0 (en)	2019-07-12	2019-08-28	Syngenta Crop Protection Ag	Microbiocidal compounds
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- 1994-01-12 CA CA002152819A patent/CA2152819C/fr not_active Expired - Lifetime
- 1994-01-12 MY MYPI94000081A patent/MY141106A/en unknown
- 1994-01-12 BR BR9405811A patent/BR9405811A/pt not_active Application Discontinuation
- 1994-01-12 SK SK895-95A patent/SK282031B6/sk not_active IP Right Cessation
- 1994-01-12 SG SG1995002217A patent/SG45131A1/en unknown
- 1994-01-12 JP JP6515697A patent/JP2732548B2/ja not_active Expired - Lifetime
- 1994-01-12 AT AT94905061T patent/ATE164586T1/de active
- 1994-01-12 DE DE2000175003 patent/DE10075003I1/de active Pending
- 1994-01-12 DK DK94905061.1T patent/DK0677054T3/da active
- 1994-01-12 PL PL94309916A patent/PL176733B1/pl unknown
- 1994-01-12 WO PCT/EP1994/000095 patent/WO1994015944A1/fr not_active Ceased
- 1994-01-12 CZ CZ951817A patent/CZ284849B6/cs not_active IP Right Cessation
- 1994-01-12 NZ NZ259868A patent/NZ259868A/en not_active IP Right Cessation
- 1994-01-12 EP EP94905061A patent/EP0677054B1/fr not_active Expired - Lifetime
- 1994-01-12 ES ES94905061T patent/ES2113639T3/es not_active Expired - Lifetime
- 1994-01-12 UA UA95073243A patent/UA42707C2/uk unknown
- 1994-01-12 DE DE69409360T patent/DE69409360T2/de not_active Expired - Lifetime
- 1994-01-12 AU AU58835/94A patent/AU679033B2/en not_active Expired
- 1994-01-12 RU RU95117100A patent/RU2125059C1/ru active
- 1994-01-13 AP APAP/P/1994/000610A patent/AP522A/en active
- 1994-01-17 YU YU1894A patent/YU49169B/sh unknown
- 1994-01-17 MA MA23397A patent/MA23091A1/fr unknown
- 1994-01-17 HU HU9400131A patent/HU221505B/hu unknown
- 1994-01-17 EG EG3094A patent/EG20582A/xx active
- 1994-01-17 ZA ZA94310A patent/ZA94310B/xx unknown
- 1994-01-17 FI FI940218A patent/FI111727B/fi not_active IP Right Cessation
- 1994-01-18 CN CN94101917A patent/CN1043768C/zh not_active Expired - Lifetime
- 1994-02-15 HR HR9300883.7 patent/HRP940110B1/xx not_active IP Right Cessation
1995
- 1995-07-15 KR KR1019950702924A patent/KR0185480B1/ko not_active Expired - Lifetime
- 1995-07-17 OA OA60688A patent/OA10223A/en unknown
- 1995-07-17 NO NO19952832A patent/NO304835B1/no not_active IP Right Cessation
1996
- 1996-08-21 BR BR1100033-3A patent/BR1100033A/pt active IP Right Grant
1998
- 1998-04-23 GR GR980400898T patent/GR3026710T3/el unknown
2000
- 2000-02-01 NL NL300003C patent/NL300003I2/nl unknown
- 2000-02-09 LU LU90518C patent/LU90518I2/fr unknown
2001
- 2001-06-11 NO NO2001010C patent/NO2001010I1/no unknown

Also Published As

Publication number	Publication date
ZA94310B (en)	1995-07-17
NL300003I1 (nl)	2000-04-03
JP2732548B2 (ja)	1998-03-30
CA2152819A1 (fr)	1994-07-21
RU2125059C1 (ru)	1999-01-20
GR3026710T3 (en)	1998-07-31
HU221505B (en)	2002-10-28
SK89595A3 (en)	1996-04-03
FI111727B (fi)	2003-09-15
DE69409360D1 (de)	1998-05-07
BR1100033A (pt)	2000-06-20
DE10075003I1 (de)	2000-06-29
YU49169B (sh)	2004-05-12
ES2113639T3 (es)	1998-05-01
AU679033B2 (en)	1997-06-19
EP0677054B1 (fr)	1998-04-01
MY141106A (en)	2010-03-15
JPH08500842A (ja)	1996-01-30
SG45131A1 (en)	1998-01-16
DE69409360T2 (de)	1998-07-23
ATE164586T1 (de)	1998-04-15
NZ259868A (en)	1997-01-29
SK282031B6 (sk)	2001-10-08
NO952832L (no)	1995-07-28
YU1894A (sh)	1997-01-08
UA42707C2 (uk)	2001-11-15
LU90518I2 (fr)	2000-04-10
PL176733B1 (pl)	1999-07-30
AP9400610A0 (en)	1994-01-31
CZ284849B6 (cs)	1999-03-17
AU5883594A (en)	1994-08-15
HRP940110B1 (en)	2001-02-28
CN1043768C (zh)	1999-06-23
NL300003I2 (nl)	2000-08-01
MA23091A1 (fr)	1994-10-01
FI940218A0 (fi)	1994-01-17
HRP940110A2 (en)	1996-12-31
IL108306A0 (en)	1994-04-12
NO2001010I1 (no)	2001-07-02
GB9300883D0 (en)	1993-03-10
DK0677054T3 (da)	1998-06-02
WO1994015944A1 (fr)	1994-07-21
HUT70411A (en)	1995-10-30
NO952832D0 (no)	1995-07-17
KR960700259A (ko)	1996-01-19
EP0677054A1 (fr)	1995-10-18
BR9405811A (pt)	1995-12-05
FI940218L (fi)	1994-07-19
NO304835B1 (no)	1999-02-22
AP522A (en)	1996-09-05
CN1099394A (zh)	1995-03-01
HU9400131D0 (en)	1994-05-30
EG20582A (en)	1999-08-30
OA10223A (en)	1997-10-07
CA2152819C (fr)	1999-03-16
CZ181795A3 (en)	1996-02-14
KR0185480B1 (en)	1999-04-01
PL309916A1 (en)	1995-11-13

Legal Events

Date	Code	Title
1998-12-27	FF	Patent granted
1999-06-20	KB	Patent renewed
2000-07-16	FF	Patent granted
2004-02-19	KB	Patent renewed
2008-02-10	KB	Patent renewed
2012-01-31	KB	Patent renewed
2014-09-30	EXP	Patent expired

Publication	Publication Date	Title
CA2152819C (fr)	1999-03-16	Nouveaux agents antiparasitaires apparentes aux milbemycines et aux avermectines
US5981500A (en)	1999-11-09	Antiparasitic agents related to the milbemycins and avermectins
DE69034222T2 (de)	2006-10-19	Avermectinderivate
US5595991A (en)	1997-01-21	Anthelmintic use of nodulisporic acid and analogs thereof
US5556868A (en)	1996-09-17	Antiparasitic avermectin and milbemycin derivatives
AU683906B2 (en)	1997-11-27	Antiparasitic agents
JPH02212491A (ja)	1990-08-23	アベルメクチン誘導体
EP0623137B1 (fr)	1999-03-10	Agents antiparasitaires
JPH0386885A (ja)	1991-04-11	アベルメクチン誘導体
EP0710242B1 (fr)	1998-05-06	Agents antiparasitaires
EP0712411B1 (fr)	1997-06-11	Agents antiparasitaires
EP0674649B1 (fr)	1997-09-10	Agents antiparasitaires
SI9400118A (sl)	1995-10-31	Sredstva proti parazitom, ki so v sorodu z milbemicini in avermektini