NO126374B - - Google Patents
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- Publication number
- NO126374B NO126374B NO03717/68A NO371768A NO126374B NO 126374 B NO126374 B NO 126374B NO 03717/68 A NO03717/68 A NO 03717/68A NO 371768 A NO371768 A NO 371768A NO 126374 B NO126374 B NO 126374B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- formula
- methanol
- solution
- compounds
- Prior art date
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- -1 dimethylamino, diethylamino Chemical group 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 29
- 239000002253 acid Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 7
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 114
- 150000001875 compounds Chemical class 0.000 description 44
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 26
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000007787 solid Substances 0.000 description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 14
- 238000001953 recrystallisation Methods 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 8
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- 241000699670 Mus sp. Species 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- DATXHLPRESKQJK-UHFFFAOYSA-N 4-pyrrolidin-1-ylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1N1CCCC1 DATXHLPRESKQJK-UHFFFAOYSA-N 0.000 description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- KGHGZRVXCKCJGX-UHFFFAOYSA-N 2-bromo-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CBr)=CC=C1C1=CC=CC=C1 KGHGZRVXCKCJGX-UHFFFAOYSA-N 0.000 description 4
- APMJLRLMIRSDQT-UHFFFAOYSA-N 2-methyl-4-(2-phenylphenyl)-1,3-thiazole Chemical compound S1C(C)=NC(C=2C(=CC=CC=2)C=2C=CC=CC=2)=C1 APMJLRLMIRSDQT-UHFFFAOYSA-N 0.000 description 4
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- CSECVTPZRPEWMJ-UHFFFAOYSA-N N,N-dimethyl-4-[2-[4-(2-phenylphenyl)-1,3-thiazol-2-yl]ethenyl]aniline Chemical compound CN(C1=CC=C(C=CC=2SC=C(N2)C2=C(C=CC=C2)C2=CC=CC=C2)C=C1)C CSECVTPZRPEWMJ-UHFFFAOYSA-N 0.000 description 4
- 230000000507 anthelmentic effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000376 reactant Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 150000002496 iodine Chemical class 0.000 description 3
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 3
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 3
- KXYJNSJYQCRPRE-UHFFFAOYSA-N 2-chloro-1-(4-phenoxyphenyl)ethanone Chemical compound C1=CC(C(=O)CCl)=CC=C1OC1=CC=CC=C1 KXYJNSJYQCRPRE-UHFFFAOYSA-N 0.000 description 2
- XROORURTAQOYLW-UHFFFAOYSA-N 2-methyl-4-phenyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=CC=CC=2)=C1 XROORURTAQOYLW-UHFFFAOYSA-N 0.000 description 2
- JPWVQUNJAKZADY-UHFFFAOYSA-N 3-(4-pyrrolidin-1-ylphenyl)prop-2-enoic acid Chemical compound C1=CC(C=CC(=O)O)=CC=C1N1CCCC1 JPWVQUNJAKZADY-UHFFFAOYSA-N 0.000 description 2
- HIJXCSPSAVIBMJ-UHFFFAOYSA-N 3-phenylprop-2-enethioamide Chemical compound NC(=S)C=CC1=CC=CC=C1 HIJXCSPSAVIBMJ-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 241001465677 Ancylostomatoidea Species 0.000 description 2
- CERFXEIVTOQFAS-UHFFFAOYSA-M CC[N+]1=C(C=CC(C=C2)=CC=C2N2CCCC2)SC=C1C(C=CC=C1)=C1C1=CC=CC=C1.[Br-] Chemical compound CC[N+]1=C(C=CC(C=C2)=CC=C2N2CCCC2)SC=C1C(C=CC=C1)=C1C1=CC=CC=C1.[Br-] CERFXEIVTOQFAS-UHFFFAOYSA-M 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- AEZBRXICRCDPKV-UHFFFAOYSA-N N,N-dimethyl-4-[2-[3-methyl-4-(2-phenylphenyl)-1,3-thiazol-3-ium-2-yl]ethenyl]aniline Chemical class CN(C1=CC=C(C=CC=2SC=C([N+]=2C)C2=C(C=CC=C2)C2=CC=CC=C2)C=C1)C AEZBRXICRCDPKV-UHFFFAOYSA-N 0.000 description 2
- DGBIYNDAYMAJFV-UHFFFAOYSA-M N,N-dimethyl-4-[2-[3-methyl-4-(2-phenylphenyl)-1,3-thiazol-3-ium-2-yl]ethenyl]aniline chloride Chemical compound [Cl-].CN(C1=CC=C(C=CC=2SC=C([N+]=2C)C2=C(C=CC=C2)C2=CC=CC=C2)C=C1)C DGBIYNDAYMAJFV-UHFFFAOYSA-M 0.000 description 2
- OWAIKXMFBSJDCJ-UHFFFAOYSA-M N,N-dimethyl-4-[2-[3-methyl-4-(2-phenylphenyl)-1,3-thiazol-3-ium-2-yl]ethenyl]aniline iodide Chemical compound [I-].CN(C1=CC=C(C=CC=2SC=C([N+]=2C)C2=C(C=CC=C2)C2=CC=CC=C2)C=C1)C OWAIKXMFBSJDCJ-UHFFFAOYSA-M 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 description 2
- 229940124339 anthelmintic agent Drugs 0.000 description 2
- 239000000921 anthelmintic agent Substances 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 150000003842 bromide salts Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 150000004694 iodide salts Chemical class 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000005956 quaternization reaction Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 150000003556 thioamides Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- CQNPVMCASGWEHM-VMPITWQZSA-N (e)-3-[4-(dimethylamino)phenyl]prop-2-enoic acid Chemical compound CN(C)C1=CC=C(\C=C\C(O)=O)C=C1 CQNPVMCASGWEHM-VMPITWQZSA-N 0.000 description 1
- DDGHBOLOCQWPKE-UHFFFAOYSA-N 1,3-thiazole;hydrobromide Chemical compound [Br-].C1=CSC=[NH+]1 DDGHBOLOCQWPKE-UHFFFAOYSA-N 0.000 description 1
- AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
- CFZFXNQQXFMCIG-UHFFFAOYSA-M 2,3-dimethyl-4-(2-phenylphenyl)-1,3-thiazol-3-ium 4-methylbenzenesulfonate Chemical compound C1(=CC=C(C=C1)S(=O)(=O)[O-])C.CC=1SC=C([N+]1C)C1=C(C=CC=C1)C1=CC=CC=C1 CFZFXNQQXFMCIG-UHFFFAOYSA-M 0.000 description 1
- XSLHNXBPPDZDAU-UHFFFAOYSA-M 2-[(e)-2-(2,5-dimethyl-1-phenylpyrrol-3-yl)ethenyl]-n,n,1-trimethylquinolin-1-ium-6-amine;hydroxide Chemical class [OH-].C1=CC2=CC(N(C)C)=CC=C2[N+](C)=C1\C=C\C(=C1C)C=C(C)N1C1=CC=CC=C1 XSLHNXBPPDZDAU-UHFFFAOYSA-M 0.000 description 1
- FLAYZKKEOIAALB-UHFFFAOYSA-N 2-bromo-1-(4-chlorophenyl)ethanone Chemical compound ClC1=CC=C(C(=O)CBr)C=C1 FLAYZKKEOIAALB-UHFFFAOYSA-N 0.000 description 1
- PORHVHVVIKTURJ-UHFFFAOYSA-N 2-bromo-1-[4-(4-methoxyphenyl)phenyl]ethanone Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)CBr)C=C1 PORHVHVVIKTURJ-UHFFFAOYSA-N 0.000 description 1
- IQEIGQFNDLINOT-UHFFFAOYSA-N 2-chloro-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CCl)=CC=C1C1=CC=CC=C1 IQEIGQFNDLINOT-UHFFFAOYSA-N 0.000 description 1
- BXRNCRJLMAFNEG-UHFFFAOYSA-N 2-iodo-1-(4-phenylphenyl)ethanone Chemical compound C1=CC(C(=O)CI)=CC=C1C1=CC=CC=C1 BXRNCRJLMAFNEG-UHFFFAOYSA-N 0.000 description 1
- HGLJWSMTJVFZDR-UHFFFAOYSA-M 3-methyl-4-(4-phenoxyphenyl)-2-[2-(4-pyrrolidin-1-ylphenyl)ethenyl]-1,3-thiazol-3-ium chloride Chemical compound [Cl-].N1(CCCC1)C1=CC=C(C=CC=2SC=C([N+]=2C)C2=CC=C(C=C2)OC2=CC=CC=C2)C=C1 HGLJWSMTJVFZDR-UHFFFAOYSA-M 0.000 description 1
- FOCILOSWFFTFNL-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=CC(Cl)=CC=2)=C1 FOCILOSWFFTFNL-UHFFFAOYSA-N 0.000 description 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 241001147672 Ancylostoma caninum Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000243780 Heligmosomoides polygyrus Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
- QQDCVPJEMZRARQ-UHFFFAOYSA-N N1(CCCC1)C1=CC=C(C=CC=2SC=C([N+]=2CC)C2=C(C=CC=C2)C2=CC=CC=C2)C=C1 Chemical class N1(CCCC1)C1=CC=C(C=CC=2SC=C([N+]=2CC)C2=C(C=CC=C2)C2=CC=CC=C2)C=C1 QQDCVPJEMZRARQ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- FJCOPNWXENNMNR-UHFFFAOYSA-N O=C(CI)C(C=C1)=CC=C1OC1=CC=CC=C1 Chemical compound O=C(CI)C(C=C1)=CC=C1OC1=CC=CC=C1 FJCOPNWXENNMNR-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 229910021607 Silver chloride Inorganic materials 0.000 description 1
- 241001480236 Strongyloides ratti Species 0.000 description 1
- 241000975692 Syphacia obvelata Species 0.000 description 1
- 241000571980 Uncinaria stenocephala Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- AVWWVJUMXRXPNF-UHFFFAOYSA-N bephenium Chemical class C=1C=CC=CC=1C[N+](C)(C)CCOC1=CC=CC=C1 AVWWVJUMXRXPNF-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000031709 bromination Effects 0.000 description 1
- 238000005893 bromination reaction Methods 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000011928 denatured alcohol Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- MNQDKWZEUULFPX-UHFFFAOYSA-M dithiazanine iodide Chemical compound [I-].S1C2=CC=CC=C2[N+](CC)=C1C=CC=CC=C1N(CC)C2=CC=CC=C2S1 MNQDKWZEUULFPX-UHFFFAOYSA-M 0.000 description 1
- 229950005765 dithiazanine iodide Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical class COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000007306 turnover Effects 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
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/14—Styryl dyes
- C09B23/145—Styryl dyes the ethylene chain carrying an heterocyclic residue, e.g. heterocycle-CH=CH-C6H5
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB43366/67A GB1244961A (en) | 1967-09-22 | 1967-09-22 | Thiazole derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126374B true NO126374B (ja) | 1973-01-29 |
Family
ID=10428460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03717/68A NO126374B (ja) | 1967-09-22 | 1968-09-20 |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3641012A (ja) |
| AT (2) | AT287708B (ja) |
| BE (2) | BE721121A (ja) |
| CA (1) | CA961852A (ja) |
| CH (1) | CH505136A (ja) |
| CS (1) | CS161846B2 (ja) |
| DE (2) | DE1795380A1 (ja) |
| DK (1) | DK135287B (ja) |
| DO (1) | DOP1968001560A (ja) |
| ES (1) | ES358405A1 (ja) |
| FI (1) | FI50415C (ja) |
| FR (3) | FR7927M (ja) |
| GB (1) | GB1244961A (ja) |
| IE (1) | IE32360B1 (ja) |
| IL (2) | IL30743A (ja) |
| IN (1) | IN117777B (ja) |
| LU (1) | LU56934A1 (ja) |
| MC (1) | MC727A1 (ja) |
| MY (1) | MY7500005A (ja) |
| NL (2) | NL6813488A (ja) |
| NO (1) | NO126374B (ja) |
| OA (1) | OA02893A (ja) |
| PH (1) | PH9310A (ja) |
| SE (1) | SE368208B (ja) |
| YU (1) | YU83573A (ja) |
| ZM (1) | ZM11268A1 (ja) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3883658A (en) * | 1968-09-19 | 1975-05-13 | Burroughs Wellcome Co | Method of treating nematode infestations |
| GB1304174A (ja) * | 1969-03-07 | 1973-01-24 | ||
| CA2590932A1 (en) * | 2004-12-17 | 2006-06-22 | Mycosol, Inc. | Thiazolium compounds and uses thereof |
| CA2628817A1 (en) * | 2005-12-01 | 2007-06-07 | Sumitomo Chemical Company, Limited | Iminopropene compound and use thereof |
| CN109503509B (zh) * | 2018-12-17 | 2021-10-19 | 湘潭大学 | 4-苯乙烯基噻唑及衍生物及其合成方法 |
-
1967
- 1967-09-22 GB GB43366/67A patent/GB1244961A/en not_active Expired
-
1968
- 1968-09-13 IE IE1113/68A patent/IE32360B1/en unknown
- 1968-09-18 DO DO1968001560A patent/DOP1968001560A/es unknown
- 1968-09-19 BE BE721121D patent/BE721121A/xx unknown
- 1968-09-19 MC MC778A patent/MC727A1/xx unknown
- 1968-09-19 AT AT1127469A patent/AT287708B/de not_active IP Right Cessation
- 1968-09-19 IL IL30743A patent/IL30743A/en unknown
- 1968-09-19 DK DK452468AA patent/DK135287B/da unknown
- 1968-09-19 US US760966A patent/US3641012A/en not_active Expired - Lifetime
- 1968-09-19 BE BE721120D patent/BE721120A/xx unknown
- 1968-09-19 IL IL30742A patent/IL30742A/en unknown
- 1968-09-19 FI FI682645A patent/FI50415C/fi active
- 1968-09-19 OA OA53371A patent/OA02893A/xx unknown
- 1968-09-19 AT AT914468A patent/AT286293B/de not_active IP Right Cessation
- 1968-09-19 ZM ZM112/68A patent/ZM11268A1/xx unknown
- 1968-09-20 FR FR167022A patent/FR7927M/fr not_active Expired
- 1968-09-20 CS CS6614A patent/CS161846B2/cs unknown
- 1968-09-20 NO NO03717/68A patent/NO126374B/no unknown
- 1968-09-20 IN IN117777A patent/IN117777B/en unknown
- 1968-09-20 LU LU56934D patent/LU56934A1/xx unknown
- 1968-09-20 NL NL6813488A patent/NL6813488A/xx unknown
- 1968-09-20 NL NL6813487A patent/NL6813487A/xx unknown
- 1968-09-20 FR FR167023A patent/FR8213M/fr not_active Expired
- 1968-09-20 CA CA030,571A patent/CA961852A/en not_active Expired
- 1968-09-20 FR FR1591630D patent/FR1591630A/fr not_active Expired
- 1968-09-21 ES ES358405A patent/ES358405A1/es not_active Expired
- 1968-09-23 CH CH1419668A patent/CH505136A/de not_active IP Right Cessation
- 1968-09-23 DE DE19681795380 patent/DE1795380A1/de active Pending
- 1968-09-23 PH PH9578*UA patent/PH9310A/en unknown
- 1968-09-23 DE DE1795381A patent/DE1795381C3/de not_active Expired
- 1968-09-23 SE SE12777/68A patent/SE368208B/xx unknown
-
1973
- 1973-03-28 YU YU00835/73A patent/YU83573A/xx unknown
-
1975
- 1975-12-30 MY MY5/75A patent/MY7500005A/xx unknown
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