DE2414612A1 - 1-aryluracile, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel - Google Patents
1-aryluracile, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittelInfo
- Publication number
- DE2414612A1 DE2414612A1 DE2414612A DE2414612A DE2414612A1 DE 2414612 A1 DE2414612 A1 DE 2414612A1 DE 2414612 A DE2414612 A DE 2414612A DE 2414612 A DE2414612 A DE 2414612A DE 2414612 A1 DE2414612 A1 DE 2414612A1
- Authority
- DE
- Germany
- Prior art keywords
- uracil
- phenyl
- dichloro
- chloro
- phenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title description 6
- 229940126601 medicinal product Drugs 0.000 title 1
- 229940035893 uracil Drugs 0.000 claims description 231
- -1 acyl isocyanate Chemical class 0.000 claims description 112
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical class O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 76
- 150000001875 compounds Chemical class 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 208000003495 Coccidiosis Diseases 0.000 claims description 17
- 206010023076 Isosporiasis Diseases 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 13
- 239000012948 isocyanate Substances 0.000 claims description 10
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000003342 alkenyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 150000002825 nitriles Chemical class 0.000 claims description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 238000006114 decarboxylation reaction Methods 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 150000002081 enamines Chemical class 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 6
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 235000021190 leftovers Nutrition 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 description 33
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 31
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 28
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 26
- 239000000243 solution Substances 0.000 description 21
- 239000000460 chlorine Substances 0.000 description 19
- 239000000203 mixture Substances 0.000 description 17
- 239000004202 carbamide Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 208000015181 infectious disease Diseases 0.000 description 15
- 235000013877 carbamide Nutrition 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229960000583 acetic acid Drugs 0.000 description 11
- 239000004480 active ingredient Substances 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 244000144977 poultry Species 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 235000013594 poultry meat Nutrition 0.000 description 10
- 239000002904 solvent Substances 0.000 description 9
- 239000003826 tablet Substances 0.000 description 9
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- DOQQTKLDEQSKIE-UHFFFAOYSA-N silver;isocyanate Chemical compound [Ag+].[N-]=C=O DOQQTKLDEQSKIE-UHFFFAOYSA-N 0.000 description 8
- 150000003672 ureas Chemical class 0.000 description 8
- 210000003250 oocyst Anatomy 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 239000003208 petroleum Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 241000223932 Eimeria tenella Species 0.000 description 5
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 150000002431 hydrogen Chemical class 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
- 241000287828 Gallus gallus Species 0.000 description 4
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 235000013330 chicken meat Nutrition 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WOYZXEVUWXQVNV-UHFFFAOYSA-N 4-phenoxyaniline Chemical compound C1=CC(N)=CC=C1OC1=CC=CC=C1 WOYZXEVUWXQVNV-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- 241001465977 Coccoidea Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000335654 Uracis Species 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000011630 iodine Substances 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000011321 prophylaxis Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 3
- SUHDJAXKVRGRJF-ONEGZZNKSA-N (e)-3-ethoxyprop-2-enoyl isocyanate Chemical compound CCO\C=C\C(=O)N=C=O SUHDJAXKVRGRJF-ONEGZZNKSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
- SFMFACMIOWQIPR-UHFFFAOYSA-N 3-ethoxyprop-2-enoyl chloride Chemical compound CCOC=CC(Cl)=O SFMFACMIOWQIPR-UHFFFAOYSA-N 0.000 description 2
- VZXOZSQDJJNBRC-UHFFFAOYSA-N 4-chlorobenzenethiol Chemical compound SC1=CC=C(Cl)C=C1 VZXOZSQDJJNBRC-UHFFFAOYSA-N 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- JDYPXXWEUHBHLV-UHFFFAOYSA-N C(C)OC=CC(=O)NC(=O)N Chemical compound C(C)OC=CC(=O)NC(=O)N JDYPXXWEUHBHLV-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 241000224483 Coccidia Species 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 241001662550 Eimeria falciformis Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- 208000032843 Hemorrhage Diseases 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 201000005485 Toxoplasmosis Diseases 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 230000000740 bleeding effect Effects 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- NSNHWTBQMQIDCF-UHFFFAOYSA-N dihydrate;hydrochloride Chemical compound O.O.Cl NSNHWTBQMQIDCF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 231100000915 pathological change Toxicity 0.000 description 2
- 230000036285 pathological change Effects 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 235000011118 potassium hydroxide Nutrition 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- ZNAGIFMERHEVFP-VURMDHGXSA-N (Z)-3-butoxybut-2-enoyl isocyanate Chemical compound C(CCC)O\C(=C/C(=O)N=C=O)\C ZNAGIFMERHEVFP-VURMDHGXSA-N 0.000 description 1
- KOKYINVGEFXZIA-FPLPWBNLSA-N (Z)-3-ethoxy-2-ethylbut-2-enoyl isocyanate Chemical compound C(C)O\C(=C(/C(=O)N=C=O)\CC)\C KOKYINVGEFXZIA-FPLPWBNLSA-N 0.000 description 1
- ZQILPOKKXROZCZ-SREVYHEPSA-N (Z)-3-ethoxy-2-methylbut-2-enoyl isocyanate Chemical compound C(C)O\C(=C(/C(=O)N=C=O)\C)\C ZQILPOKKXROZCZ-SREVYHEPSA-N 0.000 description 1
- PLFOVGOVCQCNLE-PLNGDYQASA-N (Z)-3-ethoxybut-2-enoyl chloride Chemical compound C(C)O\C(=C/C(=O)Cl)\C PLFOVGOVCQCNLE-PLNGDYQASA-N 0.000 description 1
- XAOANQDEQRLFDZ-XQRVVYSFSA-N (Z)-3-ethoxybut-2-enoyl isocyanate Chemical compound C(C)O\C(=C/C(=O)N=C=O)\C XAOANQDEQRLFDZ-XQRVVYSFSA-N 0.000 description 1
- NIIPNAJXERMYOG-UHFFFAOYSA-N 1,1,2-trimethylhydrazine Chemical compound CNN(C)C NIIPNAJXERMYOG-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- AKLYERMMCABILW-UHFFFAOYSA-N 1,2,3-tribromo-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Br)=C(Br)C(Br)=C1 AKLYERMMCABILW-UHFFFAOYSA-N 0.000 description 1
- HHLCSFGOTLUREE-UHFFFAOYSA-N 1,2,3-trichloro-5-nitrobenzene Chemical compound [O-][N+](=O)C1=CC(Cl)=C(Cl)C(Cl)=C1 HHLCSFGOTLUREE-UHFFFAOYSA-N 0.000 description 1
- DLLDRYLYVHKDKK-UHFFFAOYSA-N 1,2-dibromo-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C(Br)=C1 DLLDRYLYVHKDKK-UHFFFAOYSA-N 0.000 description 1
- ZGHQUYZPMWMLBM-UHFFFAOYSA-N 1,2-dichloro-4-phenylbenzene Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CC=CC=C1 ZGHQUYZPMWMLBM-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- RJCBYBQJVXVVKB-UHFFFAOYSA-N 1-nitro-4-phenylsulfanylbenzene Chemical compound C1=CC([N+](=O)[O-])=CC=C1SC1=CC=CC=C1 RJCBYBQJVXVVKB-UHFFFAOYSA-N 0.000 description 1
- NNWAARLSYSBVPB-UHFFFAOYSA-N 1h-imidazole-4,5-dicarboxamide Chemical compound NC(=O)C=1N=CNC=1C(N)=O NNWAARLSYSBVPB-UHFFFAOYSA-N 0.000 description 1
- IDQNBVFPZMCDDN-UHFFFAOYSA-N 2-Amino-4,6-dimethylpyrimidine Chemical compound CC1=CC(C)=NC(N)=N1 IDQNBVFPZMCDDN-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- FICQFRCPSFCFBY-UHFFFAOYSA-N 2-[bis(methylsulfanyl)methylidene]propanedinitrile Chemical compound CSC(SC)=C(C#N)C#N FICQFRCPSFCFBY-UHFFFAOYSA-N 0.000 description 1
- LAXBNTIAOJWAOP-UHFFFAOYSA-N 2-chlorobiphenyl Chemical group ClC1=CC=CC=C1C1=CC=CC=C1 LAXBNTIAOJWAOP-UHFFFAOYSA-N 0.000 description 1
- YLZYSVYZMDJYOT-UHFFFAOYSA-N 2-methoxypyrimidine Chemical class COC1=NC=CC=N1 YLZYSVYZMDJYOT-UHFFFAOYSA-N 0.000 description 1
- CUUJSCZRXAFXIP-UHFFFAOYSA-N 2-methyl-4,6-dinitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1N CUUJSCZRXAFXIP-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
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- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/263—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms
- C07D207/27—2-Pyrrolidones with only hydrogen atoms or radicals containing only hydrogen and carbon atoms directly attached to other ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- 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
-
- 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
- C07D239/54—Two oxygen atoms as doubly bound oxygen atoms or as unsubstituted hydroxy radicals
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)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
Priority Applications (23)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2414612A DE2414612A1 (de) | 1974-03-26 | 1974-03-26 | 1-aryluracile, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
PH16935A PH12431A (en) | 1974-03-26 | 1975-03-19 | 1-aryl-uracil,derivatives,pharmaceutical composition and method of use |
CA222,621A CA1036604A (en) | 1974-03-26 | 1975-03-20 | 1-aryl-uracils |
IL46890A IL46890A0 (en) | 1974-03-26 | 1975-03-21 | New-1-aryl-uracils,their production and pharmaceutical compositions containing them |
FI750870A FI750870A7 (en, 2012) | 1974-03-26 | 1975-03-24 | |
LU72124A LU72124A1 (en, 2012) | 1974-03-26 | 1975-03-24 | |
AT223675A AT336039B (de) | 1974-03-26 | 1975-03-24 | Verfahren zur herstellung von neuen 1-(aryl(oxy bzw. thio)-phenyl)-uracilen |
JP50034576A JPS50140467A (en, 2012) | 1974-03-26 | 1975-03-24 | |
DD184981A DD119232A5 (en, 2012) | 1974-03-26 | 1975-03-24 | |
JP50034577A JPS50129720A (en, 2012) | 1974-03-26 | 1975-03-24 | |
DK128175A DK139138C (da) | 1974-03-26 | 1975-03-25 | Analogifremgangsmaade til fremstilling af 1-aryluraciler |
ZA00751883A ZA751883B (en) | 1974-03-26 | 1975-03-25 | New 1-aryl-uracils, their production and their medicinal use |
BE154706A BE827119A (fr) | 1974-03-26 | 1975-03-25 | Nouveaux 1-arylucaciles, leur procede de preparation et medicament les contenant |
GB1241175A GB1456964A (en) | 1974-03-26 | 1975-03-25 | 1-aryl-uracils their production and their medicinal use |
SE7503470A SE7503470L (en, 2012) | 1974-03-26 | 1975-03-25 | |
IE660/75A IE41222B1 (en) | 1974-03-26 | 1975-03-25 | New 1-aryl-uracils their production and their medicinal use |
ES436034A ES436034A1 (es) | 1974-03-26 | 1975-03-25 | Procedimiento para la obtencion de 1-ariluracilos. |
CS752053A CS188945B2 (en) | 1974-03-26 | 1975-03-26 | Method of producing 1-aryluracils |
AU79520/75A AU487388B2 (en) | 1974-03-26 | 1975-03-26 | 1-aryl-uracils, their production and their medicinal use |
NL7503630A NL7503630A (nl) | 1974-03-26 | 1975-03-26 | Werkwijze voor het bereiden van 1-aryluracilen, alsmede de toepassing daarvan als geneesmiddel. |
HU75BA00003235A HU170782B (hu) | 1974-03-26 | 1975-03-26 | Sposob poluchenija proizvodnykh l-aril-uracila |
FR7509510A FR2265388B1 (en, 2012) | 1974-03-26 | 1975-03-26 | |
AT358576A AT337204B (de) | 1974-03-26 | 1976-05-17 | Verfahren zur herstellung von neuen 1-(aryl(oxy bzw. thio)-phenyl)-uracilen |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2414612A DE2414612A1 (de) | 1974-03-26 | 1974-03-26 | 1-aryluracile, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2414612A1 true DE2414612A1 (de) | 1975-10-16 |
Family
ID=5911235
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE2414612A Pending DE2414612A1 (de) | 1974-03-26 | 1974-03-26 | 1-aryluracile, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
Country Status (20)
Country | Link |
---|---|
JP (2) | JPS50140467A (en, 2012) |
AT (1) | AT336039B (en, 2012) |
BE (1) | BE827119A (en, 2012) |
CA (1) | CA1036604A (en, 2012) |
CS (1) | CS188945B2 (en, 2012) |
DD (1) | DD119232A5 (en, 2012) |
DE (1) | DE2414612A1 (en, 2012) |
DK (1) | DK139138C (en, 2012) |
ES (1) | ES436034A1 (en, 2012) |
FI (1) | FI750870A7 (en, 2012) |
FR (1) | FR2265388B1 (en, 2012) |
GB (1) | GB1456964A (en, 2012) |
HU (1) | HU170782B (en, 2012) |
IE (1) | IE41222B1 (en, 2012) |
IL (1) | IL46890A0 (en, 2012) |
LU (1) | LU72124A1 (en, 2012) |
NL (1) | NL7503630A (en, 2012) |
PH (1) | PH12431A (en, 2012) |
SE (1) | SE7503470L (en, 2012) |
ZA (1) | ZA751883B (en, 2012) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10040174A1 (de) | 2000-08-17 | 2002-02-28 | Bayer Ag | Verwendung von Triazintrion-Sulfonen zur Bekämpfung von Coccidiosen |
CN108524482B (zh) * | 2017-03-02 | 2022-11-25 | 中国科学院上海药物研究所 | 2-(取代苯氨基)苯甲酸类fto抑制剂治疗白血病的用途 |
JP7539377B2 (ja) * | 2018-11-30 | 2024-08-23 | 大塚製薬株式会社 | てんかん治療用複素環化合物 |
-
1974
- 1974-03-26 DE DE2414612A patent/DE2414612A1/de active Pending
-
1975
- 1975-03-19 PH PH16935A patent/PH12431A/en unknown
- 1975-03-20 CA CA222,621A patent/CA1036604A/en not_active Expired
- 1975-03-21 IL IL46890A patent/IL46890A0/xx unknown
- 1975-03-24 JP JP50034576A patent/JPS50140467A/ja active Pending
- 1975-03-24 FI FI750870A patent/FI750870A7/fi not_active Application Discontinuation
- 1975-03-24 DD DD184981A patent/DD119232A5/xx unknown
- 1975-03-24 AT AT223675A patent/AT336039B/de not_active IP Right Cessation
- 1975-03-24 JP JP50034577A patent/JPS50129720A/ja active Pending
- 1975-03-24 LU LU72124A patent/LU72124A1/xx unknown
- 1975-03-25 ZA ZA00751883A patent/ZA751883B/xx unknown
- 1975-03-25 GB GB1241175A patent/GB1456964A/en not_active Expired
- 1975-03-25 IE IE660/75A patent/IE41222B1/xx unknown
- 1975-03-25 SE SE7503470A patent/SE7503470L/xx unknown
- 1975-03-25 BE BE154706A patent/BE827119A/xx unknown
- 1975-03-25 DK DK128175A patent/DK139138C/da active
- 1975-03-25 ES ES436034A patent/ES436034A1/es not_active Expired
- 1975-03-26 HU HU75BA00003235A patent/HU170782B/hu unknown
- 1975-03-26 FR FR7509510A patent/FR2265388B1/fr not_active Expired
- 1975-03-26 NL NL7503630A patent/NL7503630A/xx not_active Application Discontinuation
- 1975-03-26 CS CS752053A patent/CS188945B2/cs unknown
Also Published As
Publication number | Publication date |
---|---|
CA1036604A (en) | 1978-08-15 |
DD119232A5 (en, 2012) | 1976-04-12 |
AT336039B (de) | 1977-04-12 |
AU7952075A (en) | 1976-09-30 |
ES436034A1 (es) | 1977-01-01 |
NL7503630A (nl) | 1975-09-30 |
FR2265388B1 (en, 2012) | 1978-08-04 |
IE41222L (en) | 1975-09-26 |
ATA223675A (de) | 1976-08-15 |
DK128175A (en, 2012) | 1975-09-27 |
CS188945B2 (en) | 1979-03-30 |
FI750870A7 (en, 2012) | 1975-09-27 |
JPS50129720A (en, 2012) | 1975-10-14 |
FR2265388A1 (en, 2012) | 1975-10-24 |
BE827119A (fr) | 1975-09-25 |
HU170782B (hu) | 1977-09-28 |
GB1456964A (en) | 1976-12-01 |
JPS50140467A (en, 2012) | 1975-11-11 |
LU72124A1 (en, 2012) | 1976-02-04 |
PH12431A (en) | 1979-02-22 |
SE7503470L (en, 2012) | 1975-09-29 |
DK139138B (da) | 1978-12-27 |
DK139138C (da) | 1979-05-28 |
IE41222B1 (en) | 1979-11-21 |
ZA751883B (en) | 1976-02-25 |
IL46890A0 (en) | 1975-05-22 |
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