CS216238B2 - Ektoparaziticide means and method of making the active substances - Google Patents
Ektoparaziticide means and method of making the active substances Download PDFInfo
- Publication number
- CS216238B2 CS216238B2 CS809021A CS902180A CS216238B2 CS 216238 B2 CS216238 B2 CS 216238B2 CS 809021 A CS809021 A CS 809021A CS 902180 A CS902180 A CS 902180A CS 216238 B2 CS216238 B2 CS 216238B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- align
- trifluoromethyl
- test
- compound
- hydroxy
- Prior art date
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- 239000013543 active substance Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical class C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 75
- 239000000203 mixture Substances 0.000 claims description 39
- 239000004480 active ingredient Substances 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
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- 230000001984 ectoparasiticidal effect Effects 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 239000011591 potassium Substances 0.000 claims description 6
- 229910052700 potassium Inorganic materials 0.000 claims description 6
- VHGCOZZUQUVMMG-UHFFFAOYSA-N 4-nitro-2-(1,1,2,2-tetrafluoroethyl)-6-(trifluoromethyl)-1,3-dihydrobenzimidazol-2-ol;sodium Chemical group [Na].FC(F)(F)C1=CC([N+]([O-])=O)=C2NC(O)(C(F)(F)C(F)F)NC2=C1 VHGCOZZUQUVMMG-UHFFFAOYSA-N 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
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- 241000256248 Spodoptera Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000255632 Tabanus atratus Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241001584775 Tunga penetrans Species 0.000 description 1
- 241000251539 Vertebrata <Metazoa> Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 150000003974 aralkylamines Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 229910001622 calcium bromide Inorganic materials 0.000 description 1
- WGEFECGEFUFIQW-UHFFFAOYSA-L calcium dibromide Chemical compound [Ca+2].[Br-].[Br-] WGEFECGEFUFIQW-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 244000078703 ectoparasite Species 0.000 description 1
- 230000002500 effect on skin Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000037406 food intake Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 238000002513 implantation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 210000004705 lumbosacral region Anatomy 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical compound CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- ZDHURYWHEBEGHO-UHFFFAOYSA-N potassiopotassium Chemical compound [K].[K] ZDHURYWHEBEGHO-UHFFFAOYSA-N 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000004945 silicone rubber Substances 0.000 description 1
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 1
- 238000005245 sintering Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000012178 vegetable wax Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles 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 in position 2
- C07D235/26—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/106,990 US4265901A (en) | 1979-12-26 | 1979-12-26 | 2-Oxybenzimidazoline compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216238B2 true CS216238B2 (en) | 1982-10-29 |
Family
ID=22314286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS809021A CS216238B2 (en) | 1979-12-26 | 1980-12-18 | Ektoparaziticide means and method of making the active substances |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4265901A (ro) |
| EP (1) | EP0031699A1 (ro) |
| JP (1) | JPS56108771A (ro) |
| KR (1) | KR840001051B1 (ro) |
| AR (1) | AR225482A1 (ro) |
| AT (1) | AT375929B (ro) |
| AU (1) | AU6539980A (ro) |
| BE (1) | BE886728A (ro) |
| BR (1) | BR8008506A (ro) |
| CA (1) | CA1156243A (ro) |
| CS (1) | CS216238B2 (ro) |
| DD (1) | DD159544A5 (ro) |
| DK (1) | DK542480A (ro) |
| ES (1) | ES498009A0 (ro) |
| FR (1) | FR2472566A1 (ro) |
| GB (1) | GB2066248B (ro) |
| GR (1) | GR72300B (ro) |
| IL (1) | IL61707A (ro) |
| IT (1) | IT1193393B (ro) |
| NZ (1) | NZ195835A (ro) |
| OA (1) | OA06672A (ro) |
| PT (1) | PT72204B (ro) |
| RO (1) | RO81209A (ro) |
| YU (1) | YU323980A (ro) |
| ZA (1) | ZA807948B (ro) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4421759A (en) * | 1981-07-27 | 1983-12-20 | Eli Lilly And Company | Methods for controlling fire ants |
| EP0113945A1 (en) * | 1983-01-19 | 1984-07-25 | Eli Lilly And Company | Amine salts |
| US5331003A (en) * | 1993-03-26 | 1994-07-19 | Eli Lilly And Company | Anticoccidial methods |
| WO2020178804A1 (en) * | 2019-03-07 | 2020-09-10 | Oti Lumionics Inc. | Materials for forming a nucleation-inhibiting coating and devices incorporating same |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| USRE20508E (en) | 1937-09-14 | Selective clutch mechanism | ||
| US3705174A (en) * | 1970-02-27 | 1972-12-05 | Merck & Co Inc | Polyhaloalkyl benzimidazoles |
| US3813407A (en) * | 1970-03-19 | 1974-05-28 | Lilly Co Eli | Process for the preparation of 1-hydroxy-2-(1,1-difluoroalkyl)benzimidazoles and 1-hydroxy-2-(1,1-difluoroalkyl)-1h-imidazo(4,5-b)pyridines |
| US3875173A (en) * | 1970-12-28 | 1975-04-01 | Lilly Co Eli | Method for introducing halogen into benzimidazole and imidazopyridine compounds |
| ZA718532B (en) * | 1970-12-28 | 1973-08-29 | Lilly Co Eli | A process for rearrangement or reduction of 1-derivatives of 1-hydroxybenzimidazoles and 1-hydroxyimidazo(4,5-b)pyriines |
| US4122184A (en) * | 1973-09-14 | 1978-10-24 | Eli Lilly And Company | Benzimidazole insecticides |
| US3980784A (en) * | 1974-12-02 | 1976-09-14 | Eli Lilly And Company | Control of animal parasites with benzimidazoles |
| FR2312495A1 (fr) * | 1975-05-27 | 1976-12-24 | Lilly Co Eli | Esters ou ethers de 1-hydroxy-2(1,1-difluoroalkyl)-benzimidazoles pesticides |
| US3989840A (en) * | 1975-07-18 | 1976-11-02 | Eli Lilly And Company | Control of animal parasites with ring-substituted N-(2,2-difluoroalkanoyl)-O-phenylenediamines |
-
1979
- 1979-12-26 US US06/106,990 patent/US4265901A/en not_active Expired - Lifetime
-
1980
- 1980-12-15 NZ NZ195835A patent/NZ195835A/xx unknown
- 1980-12-15 IL IL61707A patent/IL61707A/xx unknown
- 1980-12-15 AT AT0609280A patent/AT375929B/de not_active IP Right Cessation
- 1980-12-15 CA CA000366783A patent/CA1156243A/en not_active Expired
- 1980-12-15 AU AU65399/80A patent/AU6539980A/en not_active Abandoned
- 1980-12-16 PT PT72204A patent/PT72204B/pt unknown
- 1980-12-17 FR FR8026804A patent/FR2472566A1/fr active Granted
- 1980-12-18 BE BE1/10081A patent/BE886728A/fr not_active IP Right Cessation
- 1980-12-18 CS CS809021A patent/CS216238B2/cs unknown
- 1980-12-19 GR GR63725A patent/GR72300B/el unknown
- 1980-12-19 ZA ZA00807948A patent/ZA807948B/xx unknown
- 1980-12-19 ES ES498009A patent/ES498009A0/es active Granted
- 1980-12-19 EP EP80304645A patent/EP0031699A1/en not_active Ceased
- 1980-12-19 DK DK542480A patent/DK542480A/da not_active Application Discontinuation
- 1980-12-19 GB GB8040730A patent/GB2066248B/en not_active Expired
- 1980-12-22 YU YU03239/80A patent/YU323980A/xx unknown
- 1980-12-22 RO RO80102914A patent/RO81209A/ro unknown
- 1980-12-23 DD DD80226588A patent/DD159544A5/de unknown
- 1980-12-23 IT IT26935/80A patent/IT1193393B/it active
- 1980-12-23 BR BR8008506A patent/BR8008506A/pt unknown
- 1980-12-23 AR AR283772A patent/AR225482A1/es active
- 1980-12-24 KR KR1019800004921A patent/KR840001051B1/ko not_active Expired
- 1980-12-25 JP JP18940580A patent/JPS56108771A/ja active Pending
- 1980-12-26 OA OA57285A patent/OA06672A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ATA609280A (de) | 1984-02-15 |
| IL61707A0 (en) | 1981-01-30 |
| NZ195835A (en) | 1983-09-30 |
| IT8026935A0 (it) | 1980-12-23 |
| IT1193393B (it) | 1988-06-15 |
| US4265901A (en) | 1981-05-05 |
| AR225482A1 (es) | 1982-03-31 |
| GB2066248A (en) | 1981-07-08 |
| AT375929B (de) | 1984-09-25 |
| BE886728A (fr) | 1981-06-18 |
| DK542480A (da) | 1981-06-27 |
| RO81209A (ro) | 1983-02-01 |
| OA06672A (fr) | 1981-09-30 |
| RO81209B (ro) | 1983-01-30 |
| BR8008506A (pt) | 1981-07-21 |
| KR830004262A (ko) | 1983-07-09 |
| PT72204A (en) | 1981-01-01 |
| KR840001051B1 (ko) | 1984-07-27 |
| GB2066248B (en) | 1984-05-23 |
| ZA807948B (en) | 1982-07-28 |
| JPS56108771A (en) | 1981-08-28 |
| YU323980A (en) | 1983-09-30 |
| CA1156243A (en) | 1983-11-01 |
| AU6539980A (en) | 1981-07-02 |
| PT72204B (en) | 1981-10-28 |
| EP0031699A1 (en) | 1981-07-08 |
| IL61707A (en) | 1984-05-31 |
| FR2472566B1 (ro) | 1983-03-18 |
| ES8301222A1 (es) | 1982-12-01 |
| FR2472566A1 (fr) | 1981-07-03 |
| DD159544A5 (de) | 1983-03-16 |
| ES498009A0 (es) | 1982-12-01 |
| GR72300B (ro) | 1983-10-18 |
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