CH540281A - Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen - Google Patents
Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolenInfo
- Publication number
- CH540281A CH540281A CH378072A CH378072A CH540281A CH 540281 A CH540281 A CH 540281A CH 378072 A CH378072 A CH 378072A CH 378072 A CH378072 A CH 378072A CH 540281 A CH540281 A CH 540281A
- Authority
- CH
- Switzerland
- Prior art keywords
- thiazole
- isothiocyanatophenyl
- formula
- lower alkyl
- methyl
- Prior art date
Links
- 230000000507 anthelmentic effect Effects 0.000 title abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- SONZTNLGJRJRRW-UHFFFAOYSA-N 4-(2-isothiocyanatophenyl)-1,3-thiazole Chemical class N(=C=S)C1=C(C=CC=C1)C=1N=CSC1 SONZTNLGJRJRRW-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- 241001465754 Metazoa Species 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- DVJXGCAUVCBLIV-UHFFFAOYSA-N 2-(1,3-thiazol-4-yl)aniline Chemical compound NC1=CC=CC=C1C1=CSC=N1 DVJXGCAUVCBLIV-UHFFFAOYSA-N 0.000 claims description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 241000244206 Nematoda Species 0.000 abstract description 4
- 241000869417 Trematodes Species 0.000 abstract description 4
- 229910052794 bromium Inorganic materials 0.000 abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract description 3
- XPRSBMUZDXATCF-UHFFFAOYSA-N 4-(4-isothiocyanatophenyl)-2-methyl-1,3-thiazole Chemical compound S1C(C)=NC(C=2C=CC(=CC=2)N=C=S)=C1 XPRSBMUZDXATCF-UHFFFAOYSA-N 0.000 abstract description 2
- 229940124339 anthelmintic agent Drugs 0.000 abstract description 2
- 239000000921 anthelmintic agent Substances 0.000 abstract description 2
- ZGOFHPZQYOXFCP-UHFFFAOYSA-N 4-(1,3-thiazol-2-yl)aniline Chemical class C1=CC(N)=CC=C1C1=NC=CS1 ZGOFHPZQYOXFCP-UHFFFAOYSA-N 0.000 abstract 2
- JCRKEVDAEUPNAA-UHFFFAOYSA-N 4-(2-methyl-1,3-thiazol-4-yl)aniline Chemical compound S1C(C)=NC(C=2C=CC(N)=CC=2)=C1 JCRKEVDAEUPNAA-UHFFFAOYSA-N 0.000 abstract 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 21
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
- -1 aromatic halogenated hydrocarbons Chemical class 0.000 description 9
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- 241000699670 Mus sp. Species 0.000 description 8
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- 235000019198 oils Nutrition 0.000 description 7
- MXEAKFNUTHNKBQ-UHFFFAOYSA-N 2-chloro-4-(3-isothiocyanatophenyl)-5-methyl-1,3-thiazole Chemical compound ClC=1SC(=C(N1)C1=CC(=CC=C1)N=C=S)C MXEAKFNUTHNKBQ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 241000242711 Fasciola hepatica Species 0.000 description 6
- 206010061217 Infestation Diseases 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
- ZRXZDLLGOCTOPV-UHFFFAOYSA-N 4-(3-isothiocyanatophenyl)-2-methyl-1,3-thiazole Chemical compound CC=1SC=C(N1)C1=CC(=CC=C1)N=C=S ZRXZDLLGOCTOPV-UHFFFAOYSA-N 0.000 description 5
- BCTSKCYUNSYQAT-UHFFFAOYSA-N 4-(3-isothiocyanatophenyl)-2-methylsulfanyl-1,3-thiazole Chemical compound CSC=1SC=C(N1)C1=CC(=CC=C1)N=C=S BCTSKCYUNSYQAT-UHFFFAOYSA-N 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
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- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
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- 239000000203 mixture Substances 0.000 description 4
- RBFJQOOYZOALOV-UHFFFAOYSA-N 2-chloro-4-(4-isothiocyanatophenyl)-1,3-thiazole Chemical compound ClC=1SC=C(N1)C1=CC=C(C=C1)N=C=S RBFJQOOYZOALOV-UHFFFAOYSA-N 0.000 description 3
- FUMMYVGAPXJHMT-UHFFFAOYSA-N 2-ethoxy-4-(3-isothiocyanatophenyl)-1,3-thiazole Chemical compound C(C)OC=1SC=C(N1)C1=CC(=CC=C1)N=C=S FUMMYVGAPXJHMT-UHFFFAOYSA-N 0.000 description 3
- QDWLCBTWNDQKHQ-UHFFFAOYSA-N 4-(3-isothiocyanatophenyl)-1,3-thiazole Chemical compound N(=C=S)C=1C=C(C=CC1)C=1N=CSC1 QDWLCBTWNDQKHQ-UHFFFAOYSA-N 0.000 description 3
- LSWJAPNMIFJJOQ-UHFFFAOYSA-N 4-(3-isothiocyanatophenyl)-2-propyl-1,3-thiazole Chemical compound C(CC)C=1SC=C(N1)C1=CC(=CC=C1)N=C=S LSWJAPNMIFJJOQ-UHFFFAOYSA-N 0.000 description 3
- CHKCUVYYFAUVMI-UHFFFAOYSA-N 4-(4-bromo-3-isothiocyanatophenyl)-2-methyl-1,3-thiazole Chemical compound CC=1SC=C(N1)C1=CC(=C(C=C1)Br)N=C=S CHKCUVYYFAUVMI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 241001464384 Hymenolepis nana Species 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- HMABNTHGTIDWOU-UHFFFAOYSA-N 2-bromo-4-(3-isothiocyanatophenyl)-1,3-thiazole Chemical compound BrC=1SC=C(N1)C1=CC(=CC=C1)N=C=S HMABNTHGTIDWOU-UHFFFAOYSA-N 0.000 description 2
- VXTOBVXBSIKHEI-UHFFFAOYSA-N 2-chloro-4-(3-isothiocyanatophenyl)-1,3-thiazole Chemical compound ClC=1SC=C(N1)C1=CC(=CC=C1)N=C=S VXTOBVXBSIKHEI-UHFFFAOYSA-N 0.000 description 2
- DREZJZDGURVGEU-UHFFFAOYSA-N 2-chloro-4-(4-chloro-3-isothiocyanatophenyl)-1,3-thiazole Chemical compound ClC=1SC=C(N1)C1=CC(=C(C=C1)Cl)N=C=S DREZJZDGURVGEU-UHFFFAOYSA-N 0.000 description 2
- JGUFBXAFRCELCI-UHFFFAOYSA-N 2-ethoxy-4-(3-isothiocyanato-4-methoxyphenyl)-1,3-thiazole Chemical compound C(C)OC=1SC=C(N1)C1=CC(=C(C=C1)OC)N=C=S JGUFBXAFRCELCI-UHFFFAOYSA-N 0.000 description 2
- BVQGIJQRHQGPHD-UHFFFAOYSA-N 2-phenyl-1,3-thiazol-4-amine Chemical class NC1=CSC(C=2C=CC=CC=2)=N1 BVQGIJQRHQGPHD-UHFFFAOYSA-N 0.000 description 2
- VWLHKHHVOWOVHV-UHFFFAOYSA-N 4-(4-chloro-3-isothiocyanatophenyl)-2-methyl-1,3-thiazole Chemical compound CC=1SC=C(N1)C1=CC(=C(C=C1)Cl)N=C=S VWLHKHHVOWOVHV-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
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- CZMAXQOXGAWNDO-UHFFFAOYSA-N propane-1,1,2-triol Chemical compound CC(O)C(O)O CZMAXQOXGAWNDO-UHFFFAOYSA-N 0.000 description 2
- 229920005552 sodium lignosulfonate Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- IQKXMDSFPZADLJ-UHFFFAOYSA-N 2-butoxy-4-(4-nitrophenyl)-1,3-thiazole Chemical compound C(CCC)OC=1SC=C(N1)C1=CC=C(C=C1)[N+](=O)[O-] IQKXMDSFPZADLJ-UHFFFAOYSA-N 0.000 description 1
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- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000000022 bacteriostatic agent Substances 0.000 description 1
- 230000003385 bacteriostatic effect Effects 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- JIDPVZPXLORLJX-UHFFFAOYSA-N carbamothioyl carbamodithioate Chemical class NC(=S)SC(N)=S JIDPVZPXLORLJX-UHFFFAOYSA-N 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000010531 catalytic reduction reaction Methods 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 150000008050 dialkyl sulfates Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 235000021271 drinking Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002550 fecal effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- QPNPSTBCIKJUIR-UHFFFAOYSA-N formaldehyde;naphthalene-1-sulfonic acid;phenol Chemical class O=C.OC1=CC=CC=C1.C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 QPNPSTBCIKJUIR-UHFFFAOYSA-N 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- LPLVUJXQOOQHMX-QWBHMCJMSA-N glycyrrhizinic acid Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@H](O[C@@H]1O[C@@H]1C([C@H]2[C@]([C@@H]3[C@@]([C@@]4(CC[C@@]5(C)CC[C@@](C)(C[C@H]5C4=CC3=O)C(O)=O)C)(C)CC2)(C)CC1)(C)C)C(O)=O)[C@@H]1O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]1O LPLVUJXQOOQHMX-QWBHMCJMSA-N 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 235000011477 liquorice Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 235000013379 molasses Nutrition 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
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001993 poloxamer 188 Polymers 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 150000003557 thiazoles Chemical class 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 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
- C07D277/32—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 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Fodder In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH378072A CH540281A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH378072A CH540281A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH1624969A CH532606A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH540281A true CH540281A (de) | 1973-08-15 |
Family
ID=4415682
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH378272A CH540283A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378472A CH540285A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH1624969A CH532606A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378372A CH540284A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378172A CH540282A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378072A CH540281A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
Family Applications Before (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH378272A CH540283A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378472A CH540285A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH1624969A CH532606A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378372A CH540284A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
| CH378172A CH540282A (de) | 1969-10-30 | 1969-10-30 | Verfahren zur Herstellung von neuen 4-(Isothiocyanatophenyl)-thiazolen |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3676450A (enExample) |
| JP (1) | JPS4843847B1 (enExample) |
| CA (1) | CA960678A (enExample) |
| CH (6) | CH540283A (enExample) |
| DE (1) | DE2053178A1 (enExample) |
| FR (1) | FR2070179B1 (enExample) |
| GB (1) | GB1306396A (enExample) |
| ZA (1) | ZA707357B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4656047A (en) * | 1986-03-06 | 1987-04-07 | Kok Lanbrecht P | Rapid method for cell block preparation |
| WO2002051410A2 (en) * | 2000-12-22 | 2002-07-04 | Akzo Nobel N.V. | Phenylthiazole and thiazoline derivatives and their use as antiparasitics |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2603648A (en) * | 1951-10-18 | 1952-07-15 | Goodrich Co B F | Preparation of 2-mercapto thiazoles |
| US3127408A (en) * | 1960-06-08 | 1964-03-31 | Spencer Chem Co | 4-thiocyanato-2-butynyl carbamates |
-
1969
- 1969-10-30 CH CH378272A patent/CH540283A/de not_active IP Right Cessation
- 1969-10-30 CH CH378472A patent/CH540285A/de not_active IP Right Cessation
- 1969-10-30 CH CH1624969A patent/CH532606A/de not_active IP Right Cessation
- 1969-10-30 CH CH378372A patent/CH540284A/de not_active IP Right Cessation
- 1969-10-30 CH CH378172A patent/CH540282A/de not_active IP Right Cessation
- 1969-10-30 CH CH378072A patent/CH540281A/de not_active IP Right Cessation
-
1970
- 1970-10-19 US US82188A patent/US3676450A/en not_active Expired - Lifetime
- 1970-10-29 ZA ZA707357*A patent/ZA707357B/xx unknown
- 1970-10-29 FR FR7039042A patent/FR2070179B1/fr not_active Expired
- 1970-10-29 DE DE19702053178 patent/DE2053178A1/de active Pending
- 1970-10-29 JP JP45095019A patent/JPS4843847B1/ja active Pending
- 1970-10-29 GB GB5134070A patent/GB1306396A/en not_active Expired
- 1970-10-29 CA CA096,896A patent/CA960678A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH540283A (de) | 1973-08-15 |
| FR2070179A1 (enExample) | 1971-09-10 |
| GB1306396A (enExample) | 1973-02-07 |
| CA960678A (en) | 1975-01-07 |
| US3676450A (en) | 1972-07-11 |
| CH540284A (de) | 1973-08-15 |
| JPS4843847B1 (enExample) | 1973-12-21 |
| CH540285A (de) | 1973-08-15 |
| ZA707357B (en) | 1971-08-25 |
| CH532606A (de) | 1973-01-15 |
| CH540282A (de) | 1973-08-15 |
| FR2070179B1 (enExample) | 1974-03-22 |
| DE2053178A1 (de) | 1971-05-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |