CH507195A - Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine - Google Patents
Verfahren zur Herstellung neuer Isothiocyanato-diphenylamineInfo
- Publication number
- CH507195A CH507195A CH987170A CH987170A CH507195A CH 507195 A CH507195 A CH 507195A CH 987170 A CH987170 A CH 987170A CH 987170 A CH987170 A CH 987170A CH 507195 A CH507195 A CH 507195A
- Authority
- CH
- Switzerland
- Prior art keywords
- isothiocyanato
- diphenylamine
- hydrogen
- formula
- nitro
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 230000000507 anthelmentic effect Effects 0.000 title abstract description 5
- -1 cyano, hydroxyl Chemical group 0.000 claims abstract description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 15
- 239000002253 acid Substances 0.000 claims abstract description 13
- CZZWBQGZVPSFEQ-UHFFFAOYSA-N n-isothiocyanato-n-phenylaniline Chemical class C=1C=CC=CC=1N(N=C=S)C1=CC=CC=C1 CZZWBQGZVPSFEQ-UHFFFAOYSA-N 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 241001465754 Metazoa Species 0.000 claims description 27
- DMBHHRLKUKUOEG-UHFFFAOYSA-N N-phenyl aniline Natural products C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 150000007513 acids Chemical class 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000004385 trihaloalkyl group Chemical group 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- 125000001810 isothiocyanato group Chemical group *N=C=S 0.000 claims description 3
- NYAZXHASVIWIRJ-UHFFFAOYSA-N nitridosulfidocarbon(.) Chemical compound [S]C#N NYAZXHASVIWIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- 125000006023 1-pentenyl group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims description 2
- 150000003335 secondary amines Chemical group 0.000 claims description 2
- 125000001302 tertiary amino group Chemical group 0.000 claims description 2
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000005108 alkenylthio group Chemical group 0.000 abstract description 2
- 125000004429 atom Chemical group 0.000 abstract 3
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 abstract 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 abstract 2
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 abstract 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 abstract 1
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 8
- 206010061217 Infestation Diseases 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000287828 Gallus gallus Species 0.000 description 5
- 235000013330 chicken meat Nutrition 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000242711 Fasciola hepatica Species 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 238000002224 dissection Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 244000000013 helminth Species 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 208000006275 fascioliasis Diseases 0.000 description 3
- 230000002496 gastric effect Effects 0.000 description 3
- 210000000936 intestine Anatomy 0.000 description 3
- 210000004185 liver Anatomy 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 241000204727 Ascaridia Species 0.000 description 2
- 241000204725 Ascaridia galli Species 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
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241001464384 Hymenolepis nana Species 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000869417 Trematodes Species 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003071 parasitic effect Effects 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 241000415078 Anemone hepatica Species 0.000 description 1
- 206010002942 Apathy Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- NHKWWADFZCTJFK-UHFFFAOYSA-N CC(C)C[C]=O Chemical compound CC(C)C[C]=O NHKWWADFZCTJFK-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000242722 Cestoda Species 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 241000283086 Equidae Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 239000005639 Lauric acid Substances 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 230000001195 anabolic effect Effects 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 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
- 125000004063 butyryl group Chemical group O=C([*])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
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 235000021271 drinking Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 244000079386 endoparasite Species 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 235000013905 glycine and its sodium salt Nutrition 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000005457 ice water 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
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 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
- 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
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- ATGUVEKSASEFFO-UHFFFAOYSA-N p-aminodiphenylamine Chemical compound C1=CC(N)=CC=C1NC1=CC=CC=C1 ATGUVEKSASEFFO-UHFFFAOYSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/26—Cyanate or isocyanate esters; Thiocyanate or isothiocyanate esters
Landscapes
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Fodder In General (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH987170A CH507195A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH987170A CH507195A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH1048268A CH498817A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH507195A true CH507195A (de) | 1971-05-15 |
Family
ID=4363708
Family Applications (7)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH987170A CH507195A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987370A CH507197A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987070A CH507194A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987570A CH507903A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987270A CH507196A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH1048268A CH498817A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987470A CH507198A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
Family Applications After (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH987370A CH507197A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987070A CH507194A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987570A CH507903A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987270A CH507196A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH1048268A CH498817A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
| CH987470A CH507198A (de) | 1968-07-12 | 1968-07-12 | Verfahren zur Herstellung neuer Isothiocyanato-diphenylamine |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS4843604B1 (enExample) |
| BE (1) | BE736010A (enExample) |
| CH (7) | CH507195A (enExample) |
| CY (1) | CY807A (enExample) |
| DE (1) | DE1935338C2 (enExample) |
| FR (1) | FR2012876A1 (enExample) |
| GB (1) | GB1280887A (enExample) |
| GT (1) | GT197640465A (enExample) |
| IE (1) | IE33446B1 (enExample) |
| IL (1) | IL32603A (enExample) |
| KE (1) | KE2541A (enExample) |
| MY (1) | MY7500156A (enExample) |
| NL (1) | NL162068C (enExample) |
| YU (4) | YU36160B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2631524A1 (de) * | 1975-07-18 | 1977-02-03 | Ciba Geigy Ag | Anthelminthische praeparate |
| US4826806A (en) * | 1986-07-31 | 1989-05-02 | Shin Nisso Kako Co., Ltd. | Fluoran compounds and color forming recording materials using same |
| DE102017008628A1 (de) * | 2017-09-14 | 2019-03-14 | Julius Montz Gmbh | Stoffaustauschmaschine |
-
1968
- 1968-07-12 CH CH987170A patent/CH507195A/de not_active IP Right Cessation
- 1968-07-12 CH CH987370A patent/CH507197A/de not_active IP Right Cessation
- 1968-07-12 CH CH987070A patent/CH507194A/de not_active IP Right Cessation
- 1968-07-12 CH CH987570A patent/CH507903A/de not_active IP Right Cessation
- 1968-07-12 CH CH987270A patent/CH507196A/de not_active IP Right Cessation
- 1968-07-12 CH CH1048268A patent/CH498817A/de not_active IP Right Cessation
- 1968-07-12 CH CH987470A patent/CH507198A/de not_active IP Right Cessation
-
1969
- 1969-07-10 YU YU1773/69A patent/YU36160B/xx unknown
- 1969-07-11 JP JP44054815A patent/JPS4843604B1/ja active Pending
- 1969-07-11 CY CY807A patent/CY807A/xx unknown
- 1969-07-11 FR FR6923793A patent/FR2012876A1/fr not_active Withdrawn
- 1969-07-11 DE DE1935338A patent/DE1935338C2/de not_active Expired
- 1969-07-11 BE BE736010A patent/BE736010A/xx not_active IP Right Cessation
- 1969-07-11 IE IE946/69A patent/IE33446B1/xx unknown
- 1969-07-11 GB GB34956/69A patent/GB1280887A/en not_active Expired
- 1969-07-11 IL IL32603A patent/IL32603A/en unknown
- 1969-07-11 NL NL6910729.A patent/NL162068C/xx not_active IP Right Cessation
-
1975
- 1975-01-14 YU YU83/75A patent/YU36161B/xx unknown
- 1975-07-10 KE KE2541*UA patent/KE2541A/xx unknown
- 1975-12-30 MY MY156/75A patent/MY7500156A/xx unknown
-
1976
- 1976-03-01 GT GT197640465A patent/GT197640465A/es unknown
-
1978
- 1978-06-23 YU YU1489/78A patent/YU36162B/xx unknown
-
1979
- 1979-12-06 YU YU02976/79A patent/YU297679A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4843604B1 (enExample) | 1973-12-19 |
| GB1280887A (en) | 1972-07-05 |
| YU148978A (en) | 1981-04-30 |
| CH498817A (de) | 1970-11-15 |
| YU177369A (en) | 1981-06-30 |
| DE1935338A1 (de) | 1970-01-22 |
| IL32603A (en) | 1972-11-28 |
| DE1935338C2 (de) | 1982-05-13 |
| YU36162B (en) | 1982-02-25 |
| CH507196A (de) | 1971-05-15 |
| IE33446L (en) | 1970-01-12 |
| IL32603A0 (en) | 1969-09-25 |
| YU8375A (en) | 1981-04-30 |
| CH507197A (de) | 1971-05-15 |
| NL162068C (nl) | 1980-04-15 |
| CH507198A (de) | 1971-05-15 |
| KE2541A (en) | 1975-07-18 |
| NL162068B (nl) | 1979-11-15 |
| IE33446B1 (en) | 1974-06-26 |
| CH507194A (de) | 1971-05-15 |
| MY7500156A (en) | 1975-12-31 |
| FR2012876A1 (enExample) | 1970-03-27 |
| CH507903A (de) | 1971-05-31 |
| BE736010A (enExample) | 1970-01-12 |
| CY807A (en) | 1976-12-01 |
| YU36160B (en) | 1982-02-25 |
| YU297679A (en) | 1983-01-21 |
| NL6910729A (enExample) | 1970-01-14 |
| YU36161B (en) | 1982-02-25 |
| GT197640465A (es) | 1977-08-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |