SK287275B6 - 1-Arylpyrazoly, kompozícia s ich obsahom a ich použitie na prípravu liečiva na potláčanie parazitov na alebo vo zvieratách - Google Patents

1-Arylpyrazoly, kompozícia s ich obsahom a ich použitie na prípravu liečiva na potláčanie parazitov na alebo vo zvieratách Download PDF

Info

Publication number: SK287275B6
Authority: SK; Slovakia
Prior art keywords: formula; compound; haloalkyl; cyano; alkyl
Prior art date: 1998-12-11

Application number

SK790-2001A

Other languages

English (en)

Slovak (sk)

Other versions

SK7902001A3 (en

Inventor

Yves Ribeill

Scot Kevin Huber

Susan Marie Mccomb

Michael James Malaska

David Chou

De Leon Adalberto Perez

Original Assignee

Merial Limited

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.)

1998-12-11

Filing date

1999-12-10

Publication date

2010-05-07

1999-12-10 Application filed by Merial Limited filed Critical Merial Limited

2003-02-04 Publication of SK7902001A3 publication Critical patent/SK7902001A3/sk

2010-05-07 Publication of SK287275B6 publication Critical patent/SK287275B6/sk

Links

241001465754 Metazoa Species 0.000 title claims abstract description 52
125000004961 1-arylpyrazolyl group Chemical group 0.000 title claims abstract description 26
244000045947 parasite Species 0.000 title claims abstract description 15
239000000203 mixture Substances 0.000 title claims description 26
239000003814 drug Substances 0.000 title claims description 20
238000004519 manufacturing process Methods 0.000 title 1
239000002895 emetic Substances 0.000 claims abstract description 17
150000001875 compounds Chemical class 0.000 claims description 143
125000006414 CCl Chemical group ClC* 0.000 claims description 48
150000003839 salts Chemical class 0.000 claims description 46
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
125000004093 cyano group Chemical group *C#N 0.000 claims description 28
239000000460 chlorine Substances 0.000 claims description 24
238000002360 preparation method Methods 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical group 0.000 claims description 16
230000003071 parasitic effect Effects 0.000 claims description 16
125000003118 aryl group Chemical group 0.000 claims description 14
238000011282 treatment Methods 0.000 claims description 13
125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 12
125000000217 alkyl group Chemical group 0.000 claims description 12
-1 C 1 -C 6 -alkoxy Chemical group 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
125000001188 haloalkyl group Chemical group 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
125000004076 pyridyl group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
238000000034 method Methods 0.000 description 14
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238000006243 chemical reaction Methods 0.000 description 11
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
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239000007787 solid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
238000009472 formulation Methods 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241000607479 Yersinia pestis Species 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
230000015572 biosynthetic process Effects 0.000 description 5
IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
229940079593 drug Drugs 0.000 description 5
125000004438 haloalkoxy group Chemical group 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 4
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125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 3
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HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
239000005899 Fipronil Substances 0.000 description 3
241000282412 Homo Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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RDOXTESZEPMUJZ-UHFFFAOYSA-N methyl phenyl ether Natural products COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 3
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239000012279 sodium borohydride Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
AZSNMRSAGSSBNP-UHFFFAOYSA-N 22,23-dihydroavermectin B1a Natural products C1CC(C)C(C(C)CC)OC21OC(CC=C(C)C(OC1OC(C)C(OC3OC(C)C(O)C(OC)C3)C(OC)C1)C(C)C=CC=C1C3(C(C(=O)O4)C=C(C)C(O)C3OC1)O)CC4C2 AZSNMRSAGSSBNP-UHFFFAOYSA-N 0.000 description 2
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VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
SPBDXSGPUHCETR-JFUDTMANSA-N 8883yp2r6d Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](OC)C[C@H](O[C@@H]2C(=C/C[C@@H]3C[C@@H](C[C@@]4(O[C@@H]([C@@H](C)CC4)C(C)C)O3)OC(=O)[C@@H]3C=C(C)[C@@H](O)[C@H]4OC\C([C@@]34O)=C/C=C/[C@@H]2C)/C)O[C@H]1C.C1C[C@H](C)[C@@H]([C@@H](C)CC)O[C@@]21O[C@H](C\C=C(C)\[C@@H](O[C@@H]1O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C1)[C@@H](C)\C=C\C=C/1[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\1)O)C[C@H]4C2 SPBDXSGPUHCETR-JFUDTMANSA-N 0.000 description 2
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239000002253 acid Substances 0.000 description 2
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230000008451 emotion Effects 0.000 description 1
244000079386 endoparasite Species 0.000 description 1
JUHMHPOXZAYYJP-UHFFFAOYSA-N ethyl 5-amino-1-(4-methylphenyl)sulfonylpyrazole-4-carboxylate Chemical class NC1=C(C(=O)OCC)C=NN1S(=O)(=O)C1=CC=C(C)C=C1 JUHMHPOXZAYYJP-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
YDUDYGXZQSYYMF-UHFFFAOYSA-N ethyl n-[5-cyano-2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethylsulfonyl)pyrazol-3-yl]methanimidate Chemical compound CCOC=NC1=C(S(=O)(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl YDUDYGXZQSYYMF-UHFFFAOYSA-N 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
235000013305 food Nutrition 0.000 description 1
235000012041 food component Nutrition 0.000 description 1
239000005417 food ingredient Substances 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002949 juvenile hormone Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
150000002596 lactones Chemical class 0.000 description 1
239000012669 liquid formulation Substances 0.000 description 1
230000007774 longterm Effects 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000000463 material Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
239000003094 microcapsule Substances 0.000 description 1
FXWHFKOXMBTCMP-WMEDONTMSA-N milbemycin Natural products COC1C2OCC3=C/C=C/C(C)CC(=CCC4CC(CC5(O4)OC(C)C(C)C(OC(=O)C(C)CC(C)C)C5O)OC(=O)C(C=C1C)C23O)C FXWHFKOXMBTCMP-WMEDONTMSA-N 0.000 description 1
ZLBGSRMUSVULIE-GSMJGMFJSA-N milbemycin A3 Chemical class O1[C@H](C)[C@@H](C)CC[C@@]11O[C@H](C\C=C(C)\C[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 ZLBGSRMUSVULIE-GSMJGMFJSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
201000002266 mite infestation Diseases 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000002808 molecular sieve Substances 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000008016 pharmaceutical coating Substances 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
239000006187 pill Substances 0.000 description 1
229940068196 placebo Drugs 0.000 description 1
239000000902 placebo Substances 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
230000003449 preventive effect Effects 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
208000005687 scabies Diseases 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003462 sulfoxides Chemical group 0.000 description 1
FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000003826 tablet Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
210000004916 vomit Anatomy 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- 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
- A01N47/02—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 no bond to a nitrogen atom
- 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
- A61P33/14—Ectoparasiticides, e.g. scabicides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole 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
- C07D231/44—Oxygen and nitrogen or sulfur and nitrogen atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Dentistry (AREA)
Agronomy & Crop Science (AREA)
Environmental Sciences (AREA)
Zoology (AREA)
Wood Science & Technology (AREA)
Engineering & Computer Science (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Tropical Medicine & Parasitology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)

SK790-2001A 1998-12-11 1999-12-10 1-Arylpyrazoly, kompozícia s ich obsahom a ich použitie na prípravu liečiva na potláčanie parazitov na alebo vo zvieratách SK287275B6 (sk)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US11185798P	1998-12-11	1998-12-11
US14068099P	1999-06-24	1999-06-24
PCT/EP1999/010452 WO2000035884A1 (fr)	1998-12-11	1999-12-10	Lutte contre les arthropodes parasitant des animaux

Publications (2)

Publication Number	Publication Date
SK7902001A3 SK7902001A3 (en)	2003-02-04
SK287275B6 true SK287275B6 (sk)	2010-05-07

Family

ID=26809313

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK790-2001A SK287275B6 (sk)	1998-12-11	1999-12-10	1-Arylpyrazoly, kompozícia s ich obsahom a ich použitie na prípravu liečiva na potláčanie parazitov na alebo vo zvieratách

Country Status (32)

Country	Link
US (1)	US6160002A (fr)
EP (1)	EP1137639B1 (fr)
JP (1)	JP4757385B2 (fr)
KR (2)	KR100791407B1 (fr)
CN (1)	CN1154638C (fr)
AP (1)	AP1603A (fr)
AR (1)	AR021608A1 (fr)
AT (1)	ATE440086T1 (fr)
AU (1)	AU770796B2 (fr)
BG (1)	BG65289B1 (fr)
BR (1)	BRPI9916967B8 (fr)
CA (1)	CA2355214C (fr)
CO (1)	CO5140086A1 (fr)
CU (1)	CU23113A3 (fr)
CZ (1)	CZ303314B6 (fr)
DE (1)	DE69941303D1 (fr)
EA (1)	EA004144B1 (fr)
EE (1)	EE05363B1 (fr)
ES (1)	ES2331672T3 (fr)
HK (1)	HK1042900B (fr)
HR (1)	HRP20010437B1 (fr)
HU (1)	HUP0104636A3 (fr)
ID (1)	ID30036A (fr)
IL (4)	IL143140A0 (fr)
MA (1)	MA25274A1 (fr)
NO (1)	NO320018B1 (fr)
NZ (1)	NZ511706A (fr)
OA (1)	OA11809A (fr)
PL (1)	PL352400A1 (fr)
SK (1)	SK287275B6 (fr)
WO (1)	WO2000035884A1 (fr)
YU (1)	YU39201A (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6531501B1 (en)	1998-12-11	2003-03-11	Aventis Cropscience, S.A.	Control of arthropods in animals
JP4954425B2 (ja) *	2000-06-09	2012-06-13	メリアル・リミテツド	農薬化合物の調製方法
BR0111656B1 (pt) *	2000-06-09	2013-03-19		processos para a preparaÇço de compostos pesticidas e composto inovadores.
EP1223165A1 (fr) *	2001-01-16	2002-07-17	Aventis Cropscience S.A.	Procédé pour la préparation de pesticides
IL163790A0 (en)	2002-03-05	2005-12-18	Bayer Cropscience Sa	5-Substituted-alkylaminopyrazole derivatives as pesticides
SI1483245T1 (sl) *	2002-03-05	2007-02-28	Merial Ltd	5-substituirani alkilaminopirazolni derivati kot pesticidi
US20030215481A1 (en) *	2002-05-09	2003-11-20	Borchert Jeff N.	Control of ticks and fleas of rodents with systemic insecticides and insect growth regulators
GB0211924D0 (en)	2002-05-23	2002-07-03	Syngenta Ltd	Composition
WO2004049803A1 (fr) *	2002-12-03	2004-06-17	Bayer Cropscience S.A.	Derives pesticides de 5-(acylamino) pyrazole
BR0310113B1 (pt)	2002-12-03	2013-10-29		Composições pesticidas
CN100537545C (zh) *	2003-09-04	2009-09-09	梅里厄尔有限公司	农药
JP4875614B2 (ja)	2004-06-26	2012-02-15	メリアルリミテッド	殺虫剤としてのｎ−フェニルピラゾール誘導体
JP5765371B2 (ja) *	2013-06-14	2015-08-19	宇部興産株式会社	ペンタフルオロスルファニル基を有する複素環オリゴマー化合物
WO2017090746A1 (fr) *	2015-11-25	2017-06-01	宇部興産株式会社	Pentafluorosulfanylpyridine
CN105503829A (zh) *	2016-01-07	2016-04-20	河北蓝泰化工科技有限公司	一种氟虫腈-吡啶化合物及其制备方法和应用
CN105712933B (zh) *	2016-01-28	2019-01-11	中南民族大学	甲酰化芳基吡唑衍生物及其醚热合成方法和应用

Family Cites Families (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5232940A (en) *	1985-12-20	1993-08-03	Hatton Leslie R	Derivatives of N-phenylpyrazoles
GB8713768D0 (en) *	1987-06-12	1987-07-15	May & Baker Ltd	Compositions of matter
GB8531485D0 (en) *	1985-12-20	1986-02-05	May & Baker Ltd	Compositions of matter
DE3719732A1 (de) *	1987-06-12	1989-01-05	Bayer Ag	Substituierte 5-methylamino-1-arylpyrazole
DE3724919A1 (de) *	1987-07-28	1989-02-09	Bayer Ag	1-arylpyrazole
NO179282C (no) *	1991-01-18	1996-09-11	Rhone Poulenc Agrochimie	Nye 1-(2-pyridyl)pyrazolforbindelser til kontroll av skadeinsekter
CA2067282A1 (fr) *	1991-04-30	1992-10-31	Rhone-Poulenc Agrochimie	Pesticides de type 1-aryl-5-(alkylideneimino substitue)-pyrazoles
GB9120641D0 (en) *	1991-09-27	1991-11-06	Ici Plc	Heterocyclic compounds
US5556873A (en) *	1993-02-24	1996-09-17	Rhone-Poulenc Inc.	Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles
GB9306184D0 (en) *	1993-03-25	1993-05-19	Zeneca Ltd	Heteroaromatic compounds
DE4343832A1 (de) *	1993-12-22	1995-06-29	Bayer Ag	Substituierte 1-Arylpyrazole
GB9601128D0 (en) *	1995-08-11	1996-03-20	Pfizer Ltd	Parasiticidal compounds
US5814652A (en) *	1995-12-20	1998-09-29	Rhone-Poulenc Inc.	Pesticidal 5-amino-4-ethylsulfinyl-1-arylpyrazoles
EP0811615A1 (fr) *	1996-06-03	1997-12-10	Rhone-Poulenc Agrochimie	1-Aryle-5-((thio)amido alkyl substitué) pyrazoles et leur utilisation comme pesticides
JP3735159B2 (ja) *	1996-06-17	2006-01-18	ローヌ−プーラン・アグロシミ	新規な農薬
GB9625045D0 (en) *	1996-11-30	1997-01-22	Pfizer Ltd	Parasiticidal compounds
TW524667B (en) *	1996-12-05	2003-03-21	Pfizer	Parasiticidal pyrazoles
IL130533A (en) *	1996-12-24	2005-11-20	Rhone Poulenc Agrochimie	Insecticidal method and compositions comprising 1-phenyl or 1-pyridyl 3-acetylpyrazoles, some such compunds and process for their preparation
US6350771B1 (en) *	1996-12-24	2002-02-26	Rhone-Poulenc, Inc.	Pesticidal 1-arylpyrazoles
HUP0000464A3 (en) *	1996-12-24	2002-01-28	Rhone Poulenc Agrochimie	Pesticidal 1-aryl and pyridylpyrazole derivatives
ZA981776B (en) *	1997-03-10	1998-09-03	Rhone Poulenc Agrochimie	Pesticidal 1-arylpyrazoles
DE19824487A1 (de) *	1998-06-02	1999-12-09	Bayer Ag	Substituierte 3-Thiocarbamoylpyrazole

1999
- 1999-12-09 AR ARP990106282A patent/AR021608A1/es active IP Right Grant
- 1999-12-10 HU HU0104636A patent/HUP0104636A3/hu unknown
- 1999-12-10 PL PL99352400A patent/PL352400A1/xx not_active Application Discontinuation
- 1999-12-10 CN CNB998142689A patent/CN1154638C/zh not_active Expired - Lifetime
- 1999-12-10 DE DE69941303T patent/DE69941303D1/de not_active Expired - Lifetime
- 1999-12-10 WO PCT/EP1999/010452 patent/WO2000035884A1/fr not_active Ceased
- 1999-12-10 US US09/457,869 patent/US6160002A/en not_active Expired - Lifetime
- 1999-12-10 AT AT99964686T patent/ATE440086T1/de not_active IP Right Cessation
- 1999-12-10 ID IDW00200101414A patent/ID30036A/id unknown
- 1999-12-10 ES ES99964686T patent/ES2331672T3/es not_active Expired - Lifetime
- 1999-12-10 AP APAP/P/2001/002163A patent/AP1603A/en active
- 1999-12-10 HR HR20010437A patent/HRP20010437B1/xx not_active IP Right Cessation
- 1999-12-10 IL IL14314099A patent/IL143140A0/xx active IP Right Grant
- 1999-12-10 CZ CZ20012030A patent/CZ303314B6/cs not_active IP Right Cessation
- 1999-12-10 AU AU30442/00A patent/AU770796B2/en not_active Expired
- 1999-12-10 NZ NZ511706A patent/NZ511706A/en not_active IP Right Cessation
- 1999-12-10 HK HK02104424.6A patent/HK1042900B/zh not_active IP Right Cessation
- 1999-12-10 EA EA200100653A patent/EA004144B1/ru not_active IP Right Cessation
- 1999-12-10 EP EP99964686A patent/EP1137639B1/fr not_active Expired - Lifetime
- 1999-12-10 KR KR1020017007046A patent/KR100791407B1/ko not_active Expired - Lifetime
- 1999-12-10 CA CA2355214A patent/CA2355214C/fr not_active Expired - Lifetime
- 1999-12-10 KR KR1020077001923A patent/KR100859295B1/ko not_active Expired - Lifetime
- 1999-12-10 SK SK790-2001A patent/SK287275B6/sk not_active IP Right Cessation
- 1999-12-10 EE EEP200100307A patent/EE05363B1/xx unknown
- 1999-12-10 BR BRPI9916967A patent/BRPI9916967B8/pt not_active IP Right Cessation
- 1999-12-10 OA OA1200100145A patent/OA11809A/en unknown
- 1999-12-10 JP JP2000588146A patent/JP4757385B2/ja not_active Expired - Lifetime
- 1999-12-11 YU YU39201A patent/YU39201A/sh unknown
- 1999-12-13 CO CO99077824A patent/CO5140086A1/es unknown
2001
- 2001-05-14 IL IL143140A patent/IL143140A/en not_active IP Right Cessation
- 2001-06-07 NO NO20012820A patent/NO320018B1/no not_active IP Right Cessation
- 2001-06-11 CU CU135A patent/CU23113A3/es unknown
- 2001-06-14 BG BG105603A patent/BG65289B1/bg unknown
- 2001-07-04 MA MA26258A patent/MA25274A1/fr unknown
2007
- 2007-07-09 IL IL184500A patent/IL184500A/en not_active IP Right Cessation
- 2007-07-09 IL IL184501A patent/IL184501A/en not_active IP Right Cessation

Also Published As

Publication number	Publication date
CN1329600A (zh)	2002-01-02
EP1137639A1 (fr)	2001-10-04
HRP20010437B1 (hr)	2011-09-30
NO20012820D0 (no)	2001-06-07
NO20012820L (no)	2001-08-13
YU39201A (sh)	2004-07-15
CA2355214C (fr)	2010-02-23
BRPI9916967B1 (pt)	2016-04-12
EA004144B1 (ru)	2004-02-26
AR021608A1 (es)	2002-07-31
HUP0104636A3 (en)	2002-04-29
AU3044200A (en)	2000-07-03
KR100859295B1 (ko)	2008-09-19
CN1154638C (zh)	2004-06-23
IL143140A (en)	2008-08-07
EA200100653A1 (ru)	2001-12-24
HK1042900B (zh)	2005-04-01
CZ303314B6 (cs)	2012-08-01
BR9916967A (pt)	2001-09-25
ID30036A (id)	2001-11-01
DE69941303D1 (de)	2009-10-01
JP4757385B2 (ja)	2011-08-24
MA25274A1 (fr)	2001-10-01
NZ511706A (en)	2003-12-19
US6160002A (en)	2000-12-12
BG65289B1 (bg)	2007-12-28
OA11809A (en)	2005-08-17
CA2355214A1 (fr)	2000-06-22
ATE440086T1 (de)	2009-09-15
SK7902001A3 (en)	2003-02-04
ES2331672T3 (es)	2010-01-12
KR20010108006A (ko)	2001-12-07
CO5140086A1 (es)	2002-03-22
IL143140A0 (en)	2002-04-21
BG105603A (en)	2002-01-31
CU23113A3 (es)	2006-02-27
NO320018B1 (no)	2005-10-10
EE05363B1 (et)	2010-12-15
CZ20012030A3 (cs)	2002-03-13
IL184501A (en)	2008-08-07
HRP20010437A2 (en)	2002-06-30
KR100791407B1 (ko)	2008-01-07
AP1603A (en)	2006-04-28
HK1042900A1 (en)	2002-08-30
KR20070020145A (ko)	2007-02-16
HUP0104636A2 (hu)	2002-03-28
JP2002532477A (ja)	2002-10-02
BRPI9916967B8 (pt)	2022-07-26
WO2000035884A1 (fr)	2000-06-22
PL352400A1 (en)	2003-08-25
EE200100307A (et)	2002-12-16
EP1137639B1 (fr)	2009-08-19
AP2001002163A0 (en)	2001-06-30
AU770796B2 (en)	2004-03-04
IL184500A (en)	2008-08-07

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Date	Code	Title	Description
2020-02-04	MK4A	Expiry of patent	Expiry date: 20191210

Publication	Publication Date	Title
IL184500A (en)	2008-08-07	1-Aryphrazole compounds and a method for controlling parasites on or in non-human animals
AU676343B2 (en)	1997-03-06	Pesticidal 1-arylpyrroles
EP0235628B1 (fr)	1991-04-24	1-Arylpyrazoles
KR100815637B1 (ko)	2008-03-20	살충제로서 치환된 아릴피라졸
US6992099B2 (en)	2006-01-31	Control of arthropods in animals
US6630499B1 (en)	2003-10-07	Control of arthropods in animals
MXPA01005832A (en)	2002-03-26	Control of arthropods in animals
US20020016468A1 (en)	2002-02-07	Pesticidal 1-arylpyrazole derivatives