BE693739A - - Google Patents
Info
- Publication number
- BE693739A BE693739A BE693739DA BE693739A BE 693739 A BE693739 A BE 693739A BE 693739D A BE693739D A BE 693739DA BE 693739 A BE693739 A BE 693739A
- Authority
- BE
- Belgium
- Prior art keywords
- sep
- complex
- compound
- chloride
- dimethylaminophenyl
- Prior art date
Links
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 69
- 241001465754 Metazoa Species 0.000 claims description 45
- -1 benzothiazolium compound Chemical class 0.000 claims description 42
- 150000001875 compounds Chemical class 0.000 claims description 33
- 239000004202 carbamide Substances 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 27
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 23
- 244000045947 parasite Species 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 15
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- JADVWWSKYZXRGX-UHFFFAOYSA-M thioflavine T Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JADVWWSKYZXRGX-UHFFFAOYSA-M 0.000 claims description 15
- 239000000460 chlorine Chemical group 0.000 claims description 14
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 229910052801 chlorine Chemical group 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 239000007787 solid Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 229960000789 guanidine hydrochloride Drugs 0.000 claims description 9
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 claims description 9
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 8
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 8
- 229960004198 guanidine Drugs 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000002989 phenols Chemical class 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 230000037396 body weight Effects 0.000 claims description 6
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 244000000054 animal parasite Species 0.000 claims description 5
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 239000004094 surface-active agent Substances 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- WMPDQLXFSCRILT-UHFFFAOYSA-M 4-(3,6-dimethyl-1,3-benzothiazol-3-ium-2-yl)-n,n-dimethylaniline;bromide Chemical compound [Br-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 WMPDQLXFSCRILT-UHFFFAOYSA-M 0.000 claims description 3
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 241000607479 Yersinia pestis Species 0.000 claims description 2
- 150000001805 chlorine compounds Chemical group 0.000 claims description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 claims description 2
- JUUWYQFWTIMCNM-UHFFFAOYSA-M 4-(3,6-dimethyl-1,3-benzothiazol-3-ium-2-yl)-n,n-dimethylaniline;iodide Chemical compound [I-].C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 JUUWYQFWTIMCNM-UHFFFAOYSA-M 0.000 claims 1
- WBRPALKQWDSAPL-UHFFFAOYSA-N n,n-dimethyl-4-(3-methyl-1,3-benzothiazol-3-ium-2-yl)aniline Chemical compound C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=CC=C2S1 WBRPALKQWDSAPL-UHFFFAOYSA-N 0.000 claims 1
- 241000282887 Suidae Species 0.000 description 25
- 239000000047 product Substances 0.000 description 20
- 235000013601 eggs Nutrition 0.000 description 19
- 241001494479 Pecora Species 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 241000244185 Ascaris lumbricoides Species 0.000 description 13
- 241000244186 Ascaris Species 0.000 description 12
- 208000024891 symptom Diseases 0.000 description 12
- 210000003608 fece Anatomy 0.000 description 11
- 235000013305 food Nutrition 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000011081 inoculation Methods 0.000 description 9
- 239000007788 liquid Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000011149 active material Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 239000000376 reactant Substances 0.000 description 7
- 230000003071 parasitic effect Effects 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 230000001617 migratory effect Effects 0.000 description 5
- 206010011224 Cough Diseases 0.000 description 4
- 208000022531 anorexia Diseases 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 206010061428 decreased appetite Diseases 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000009548 growth disturbance Effects 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 210000004185 liver Anatomy 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 230000029058 respiratory gaseous exchange Effects 0.000 description 4
- 210000002345 respiratory system Anatomy 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 206010013975 Dyspnoeas Diseases 0.000 description 3
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000003902 lesion Effects 0.000 description 3
- FXEKRIDRIFBJOR-UHFFFAOYSA-N thioflavin T cation Chemical compound C1=CC(N(C)C)=CC=C1C1=[N+](C)C2=CC=C(C)C=C2S1 FXEKRIDRIFBJOR-UHFFFAOYSA-N 0.000 description 3
- VGMJYYDKPUPTID-UHFFFAOYSA-N 4-ethylbenzene-1,3-diol Chemical compound CCC1=CC=C(O)C=C1O VGMJYYDKPUPTID-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- 241000931178 Bunostomum Species 0.000 description 2
- 241000243976 Haemonchus Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000510960 Oesophagostomum Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000731783 Strongyloides papillosus Species 0.000 description 2
- 241000243797 Trichostrongylus Species 0.000 description 2
- 241001489151 Trichuris Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- GGNQRNBDZQJCCN-UHFFFAOYSA-N benzene-1,2,4-triol Chemical compound OC1=CC=C(O)C(O)=C1 GGNQRNBDZQJCCN-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000036541 health Effects 0.000 description 2
- XLYOFNOQVPJJNP-ZSJDYOACSA-N heavy water Substances [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 2
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 230000001418 larval effect Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000004682 monohydrates Chemical class 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 230000000590 parasiticidal effect Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 241000894007 species Species 0.000 description 2
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 1
- XIRABDOOVRWLFU-UHFFFAOYSA-N 2,4-dimethylbenzene-1,3,5-triol Chemical compound CC1=C(O)C=C(O)C(C)=C1O XIRABDOOVRWLFU-UHFFFAOYSA-N 0.000 description 1
- UFBJCMHMOXMLKC-UHFFFAOYSA-N 2,4-dinitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O UFBJCMHMOXMLKC-UHFFFAOYSA-N 0.000 description 1
- GLJCPHKWYYCHCQ-UHFFFAOYSA-N 2,5-dimethoxybenzene-1,4-diol Chemical compound COC1=CC(O)=C(OC)C=C1O GLJCPHKWYYCHCQ-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- CJQALGPVJPPULG-UHFFFAOYSA-N 4,5,6-trichlorobenzene-1,2,3-triol Chemical compound OC1=C(O)C(Cl)=C(Cl)C(Cl)=C1O CJQALGPVJPPULG-UHFFFAOYSA-N 0.000 description 1
- GPOQODYGMUTOQL-UHFFFAOYSA-N 4-bromo-3-methylphenol Chemical compound CC1=CC(O)=CC=C1Br GPOQODYGMUTOQL-UHFFFAOYSA-N 0.000 description 1
- WFJIVOKAWHGMBH-UHFFFAOYSA-N 4-hexylbenzene-1,3-diol Chemical compound CCCCCCC1=CC=C(O)C=C1O WFJIVOKAWHGMBH-UHFFFAOYSA-N 0.000 description 1
- VSMDINRNYYEDRN-UHFFFAOYSA-N 4-iodophenol Chemical compound OC1=CC=C(I)C=C1 VSMDINRNYYEDRN-UHFFFAOYSA-N 0.000 description 1
- XJNPNXSISMKQEX-UHFFFAOYSA-N 4-nitrocatechol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1O XJNPNXSISMKQEX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001147657 Ancylostoma Species 0.000 description 1
- 241000244188 Ascaris suum Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000893172 Chabertia Species 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 241001126268 Cooperia Species 0.000 description 1
- 241000935794 Dipylidium Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 244000078958 Gardenia weissichii Species 0.000 description 1
- 241000404582 Hymenolepis <angiosperm> Species 0.000 description 1
- 241001137878 Moniezia Species 0.000 description 1
- 241000498270 Necator americanus Species 0.000 description 1
- 241000243795 Ostertagia Species 0.000 description 1
- 241000282320 Panthera leo Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 description 1
- 241001277123 Physaloptera Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000244174 Strongyloides Species 0.000 description 1
- 241000975704 Syphacia Species 0.000 description 1
- 241000244155 Taenia Species 0.000 description 1
- 241000607216 Toxascaris Species 0.000 description 1
- 241000244031 Toxocara Species 0.000 description 1
- 241000244030 Toxocara canis Species 0.000 description 1
- 241000571986 Uncinaria Species 0.000 description 1
- VWPUAXALDFFXJW-UHFFFAOYSA-N benzenehexol Chemical compound OC1=C(O)C(O)=C(O)C(O)=C1O VWPUAXALDFFXJW-UHFFFAOYSA-N 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 230000036449 good health Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 244000000053 intestinal parasite Species 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 210000004324 lymphatic system Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 229940079877 pyrogallol Drugs 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- RRBMVWQICIXSEO-UHFFFAOYSA-N tetrachlorocatechol Chemical compound OC1=C(O)C(Cl)=C(Cl)C(Cl)=C1Cl RRBMVWQICIXSEO-UHFFFAOYSA-N 0.000 description 1
- XJVIPPHGDPEDJL-UHFFFAOYSA-N thiourea;hydrochloride Chemical compound Cl.NC(N)=S XJVIPPHGDPEDJL-UHFFFAOYSA-N 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
- C07D277/66—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2 with aromatic rings or ring systems directly attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US35235564A | 1964-03-16 | 1964-03-16 | |
| US43178865A | 1965-02-11 | 1965-02-11 | |
| US43178765A | 1965-02-11 | 1965-02-11 | |
| ZA651190 | 1965-03-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE693739A true BE693739A (https=) | 1967-08-07 |
Family
ID=27502837
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE693739D BE693739A (https=) | 1964-03-16 | 1967-02-07 |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE693739A (https=) |
-
1967
- 1967-02-07 BE BE693739D patent/BE693739A/fr unknown
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