DD209812A5 - Verfahren zur herstellung von carbazinsaeurederivaten - Google Patents
Verfahren zur herstellung von carbazinsaeurederivaten Download PDFInfo
- Publication number
- DD209812A5 DD209812A5 DD83250605A DD25060583A DD209812A5 DD 209812 A5 DD209812 A5 DD 209812A5 DD 83250605 A DD83250605 A DD 83250605A DD 25060583 A DD25060583 A DD 25060583A DD 209812 A5 DD209812 A5 DD 209812A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- item
- acid
- alkyl
- reaction
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 28
- HJCUTNIGJHJGCF-UHFFFAOYSA-N acridan acid Natural products C1=CC=C2CC3=CC=CC=C3NC2=C1 HJCUTNIGJHJGCF-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- -1 indanylidene Chemical group 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 4
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 3
- 125000001041 indolyl group Chemical group 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
- 239000007858 starting material Substances 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000002576 ketones Chemical class 0.000 claims description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 238000002955 isolation Methods 0.000 claims description 6
- 150000002429 hydrazines Chemical class 0.000 claims description 5
- 150000002431 hydrogen Chemical group 0.000 claims description 5
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- 239000003849 aromatic solvent Substances 0.000 claims 1
- 235000019786 weight gain Nutrition 0.000 abstract description 11
- 230000004584 weight gain Effects 0.000 abstract description 11
- 238000003975 animal breeding Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- PERZMHJGZKHNGU-JGYWJTCASA-N bambermycin Chemical compound O([C@H]1[C@H](NC(C)=O)[C@@H](O)[C@@H]([C@H](O1)CO[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@@H]1O[C@@H]([C@H]([C@H](O)[C@H]1NC(C)=O)O[C@H]1[C@@H]([C@@H](O)[C@@H](O)[C@H](O1)C(=O)NC=1C(CCC=1O)=O)O)C)[C@H]1[C@@H](OP(O)(=O)OC[C@@H](OC\C=C(/C)CC\C=C\C(C)(C)CCC(=C)C\C=C(/C)CCC=C(C)C)C(O)=O)O[C@H](C(O)=O)[C@@](C)(O)[C@@H]1OC(N)=O PERZMHJGZKHNGU-JGYWJTCASA-N 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 240000008042 Zea mays Species 0.000 description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000011782 vitamin Substances 0.000 description 6
- 235000013343 vitamin Nutrition 0.000 description 6
- 229940088594 vitamin Drugs 0.000 description 6
- 229930003231 vitamin Natural products 0.000 description 6
- 239000004181 Flavomycin Substances 0.000 description 5
- 241000282887 Suidae Species 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 235000019374 flavomycin Nutrition 0.000 description 5
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 5
- 239000003549 soybean oil Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000011573 trace mineral Substances 0.000 description 5
- 235000013619 trace mineral Nutrition 0.000 description 5
- 150000003722 vitamin derivatives Chemical class 0.000 description 5
- 235000019733 Fish meal Nutrition 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 235000019764 Soybean Meal Nutrition 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 239000001506 calcium phosphate Substances 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000004467 fishmeal Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 229960003512 nicotinic acid Drugs 0.000 description 4
- 235000001968 nicotinic acid Nutrition 0.000 description 4
- 239000011664 nicotinic acid Substances 0.000 description 4
- 239000012429 reaction media Substances 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 239000004455 soybean meal Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000000080 wetting agent Substances 0.000 description 4
- BCZXFFBUYPCTSJ-UHFFFAOYSA-L Calcium propionate Chemical compound [Ca+2].CCC([O-])=O.CCC([O-])=O BCZXFFBUYPCTSJ-UHFFFAOYSA-L 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 235000021052 average daily weight gain Nutrition 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 3
- 239000004330 calcium propionate Substances 0.000 description 3
- 235000010331 calcium propionate Nutrition 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 3
- 229940038472 dicalcium phosphate Drugs 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052742 iron Inorganic materials 0.000 description 3
- 244000144972 livestock Species 0.000 description 3
- 235000010446 mineral oil Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000011701 zinc Substances 0.000 description 3
- 229910052725 zinc Inorganic materials 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- IUNJCFABHJZSKB-UHFFFAOYSA-N 2,4-dihydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C(O)=C1 IUNJCFABHJZSKB-UHFFFAOYSA-N 0.000 description 2
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 235000019743 Choline chloride Nutrition 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- SXVPOSFURRDKBO-UHFFFAOYSA-N Cyclododecanone Chemical compound O=C1CCCCCCCCCCC1 SXVPOSFURRDKBO-UHFFFAOYSA-N 0.000 description 2
- 240000005979 Hordeum vulgare Species 0.000 description 2
- 235000007340 Hordeum vulgare Nutrition 0.000 description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- AUNGANRZJHBGPY-SCRDCRAPSA-N Riboflavin Chemical compound OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O AUNGANRZJHBGPY-SCRDCRAPSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- 239000003674 animal food additive Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical class NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 2
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 2
- 229960003178 choline chloride Drugs 0.000 description 2
- 239000002285 corn oil Substances 0.000 description 2
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- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- CBOQJANXLMLOSS-UHFFFAOYSA-N ethyl vanillin Chemical compound CCOC1=CC(C=O)=CC=C1O CBOQJANXLMLOSS-UHFFFAOYSA-N 0.000 description 2
- NGAZZOYFWWSOGK-UHFFFAOYSA-N ethyl-n-butyl-ketone Natural products CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
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- 229910052748 manganese Inorganic materials 0.000 description 2
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- 235000012054 meals Nutrition 0.000 description 2
- RARSHUDCJQSEFJ-UHFFFAOYSA-N p-Hydroxypropiophenone Chemical compound CCC(=O)C1=CC=C(O)C=C1 RARSHUDCJQSEFJ-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 238000001953 recrystallisation Methods 0.000 description 2
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- 235000019155 vitamin A Nutrition 0.000 description 2
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- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 2
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 1
- ADCYRBXQAJXJTD-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Cl)C=C1 ADCYRBXQAJXJTD-UHFFFAOYSA-N 0.000 description 1
- GKDLTXYXODKDEA-UHFFFAOYSA-N 1-phenylbutan-2-one Chemical compound CCC(=O)CC1=CC=CC=C1 GKDLTXYXODKDEA-UHFFFAOYSA-N 0.000 description 1
- FPIPGXGPPPQFEQ-UHFFFAOYSA-N 13-cis retinol Natural products OCC=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-UHFFFAOYSA-N 0.000 description 1
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- CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 1
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- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
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- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
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- 229940036811 bone meal Drugs 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
- YYRMJZQKEFZXMX-UHFFFAOYSA-L calcium bis(dihydrogenphosphate) Chemical compound [Ca+2].OP(O)([O-])=O.OP(O)([O-])=O YYRMJZQKEFZXMX-UHFFFAOYSA-L 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical class OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- FDJOLVPMNUYSCM-UVKKECPRSA-L cobalt(3+);[(2r,3s,4r,5s)-5-(5,6-dimethylbenzimidazol-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl] [(2r)-1-[3-[(2r,3r,4z,7s,9z,12s,13s,14z,17s,18s,19r)-2,13,18-tris(2-amino-2-oxoethyl)-7,12,17-tris(3-amino-3-oxopropyl)-3,5,8,8,13,15,18,19-octamethyl-2,7, Chemical compound [Co+3].N#[C-].C1([C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)[N-]\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O FDJOLVPMNUYSCM-UVKKECPRSA-L 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- IIRFCWANHMSDCG-UHFFFAOYSA-N cyclooctanone Chemical compound O=C1CCCCCCC1 IIRFCWANHMSDCG-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- IDAGXRIGDWCIET-SDFKWCIISA-L disodium;(2s,3s,4s,5r)-2,3,4,5-tetrahydroxyhexanedioate Chemical compound [Na+].[Na+].[O-]C(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O IDAGXRIGDWCIET-SDFKWCIISA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- XSMGVELVBJSIDK-UHFFFAOYSA-N ethyl n-(cyclododecylideneamino)carbamate Chemical compound CCOC(=O)NN=C1CCCCCCCCCCC1 XSMGVELVBJSIDK-UHFFFAOYSA-N 0.000 description 1
- 244000144993 groups of animals Species 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- LIAWOTKNAVAKCX-UHFFFAOYSA-N hydrazine;dihydrochloride Chemical compound Cl.Cl.NN LIAWOTKNAVAKCX-UHFFFAOYSA-N 0.000 description 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 description 1
- OLNJUISKUQQNIM-UHFFFAOYSA-N indole-3-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CNC2=C1 OLNJUISKUQQNIM-UHFFFAOYSA-N 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- TYQCGQRIZGCHNB-JLAZNSOCSA-N l-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(O)=C(O)C1=O TYQCGQRIZGCHNB-JLAZNSOCSA-N 0.000 description 1
- 159000000003 magnesium salts Chemical class 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- ZIEROCRNWRMODY-UHFFFAOYSA-N methyl N-[(3-ethoxy-4-hydroxyphenyl)methylideneamino]carbamate Chemical compound CCOc1cc(C=NNC(=O)OC)ccc1O ZIEROCRNWRMODY-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- JWXFBWMLDZPHOI-UHFFFAOYSA-N methyl n-(1-phenylbutan-2-ylideneamino)carbamate Chemical compound COC(=O)NN=C(CC)CC1=CC=CC=C1 JWXFBWMLDZPHOI-UHFFFAOYSA-N 0.000 description 1
- QTRWZVQQCJPXGW-UHFFFAOYSA-N methyl n-(1-phenylhexadecylideneamino)carbamate Chemical compound CCCCCCCCCCCCCCCC(=NNC(=O)OC)C1=CC=CC=C1 QTRWZVQQCJPXGW-UHFFFAOYSA-N 0.000 description 1
- BOHLDNPMHREUCY-UHFFFAOYSA-N methyl n-[(4-nitrophenyl)methylideneamino]carbamate Chemical compound COC(=O)NN=CC1=CC=C([N+]([O-])=O)C=C1 BOHLDNPMHREUCY-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 229910000150 monocalcium phosphate Inorganic materials 0.000 description 1
- 235000019691 monocalcium phosphate Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 150000005621 tetraalkylammonium salts Chemical class 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940100445 wheat starch Drugs 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K50/00—Feeding-stuffs specially adapted for particular animals
- A23K50/30—Feeding-stuffs specially adapted for particular animals for swines
-
- 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
- A23K20/105—Aliphatic or alicyclic 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
- A23K20/111—Aromatic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU821381A HU190795B (en) | 1982-05-04 | 1982-05-04 | Process for producing carbazinic derivatives and compositions containing them for increasing weight yield |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD209812A5 true DD209812A5 (de) | 1984-05-23 |
Family
ID=10954201
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83250605A DD209812A5 (de) | 1982-05-04 | 1983-05-04 | Verfahren zur herstellung von carbazinsaeurederivaten |
Country Status (25)
| Country | Link |
|---|---|
| US (2) | US4570002A (forum.php) |
| JP (1) | JPS5936655A (forum.php) |
| AR (1) | AR231531A1 (forum.php) |
| AT (2) | AT384804B (forum.php) |
| AU (1) | AU565379B2 (forum.php) |
| BE (1) | BE896629A (forum.php) |
| CA (1) | CA1194885A (forum.php) |
| CH (1) | CH659244A5 (forum.php) |
| CS (1) | CS240967B2 (forum.php) |
| DD (1) | DD209812A5 (forum.php) |
| DE (1) | DE3316316A1 (forum.php) |
| DK (1) | DK196983A (forum.php) |
| ES (1) | ES8501370A1 (forum.php) |
| FI (1) | FI78815C (forum.php) |
| FR (1) | FR2526424B1 (forum.php) |
| GB (1) | GB2119381B (forum.php) |
| GR (1) | GR78250B (forum.php) |
| HU (1) | HU190795B (forum.php) |
| IT (1) | IT1221914B (forum.php) |
| NL (1) | NL8301544A (forum.php) |
| PH (1) | PH19991A (forum.php) |
| PL (1) | PL138376B1 (forum.php) |
| SE (1) | SE8302481L (forum.php) |
| SU (1) | SU1299503A3 (forum.php) |
| YU (1) | YU42855B (forum.php) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU192633B (en) * | 1984-12-12 | 1987-06-29 | Egyt Gyogyszervegyeszeti Gyar | Process for producing carbazinic acid derivatives and compositions containing them for increasing weight-yield |
| DE3624349A1 (de) * | 1986-07-17 | 1988-01-28 | Schering Ag | Substituierte hydrazone, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel |
| FR2615188B1 (fr) * | 1987-05-14 | 1989-11-17 | Meram Laboratoires Sa | Derives d'hydrazine, procede d'obtention et compositions pharmaceutiques les contenant |
| JPH0482870A (ja) * | 1990-07-24 | 1992-03-16 | Kureha Chem Ind Co Ltd | ヒドラゾン誘導体の製造方法 |
| FR2715155B1 (fr) * | 1994-01-19 | 1996-07-26 | Mayoly Spindler | Inhibiteurs de la monoamine oxydase B et leurs procédés de préparation. |
| CN110563751B (zh) * | 2019-07-16 | 2021-01-15 | 杭州职业技术学院 | 一种苯腙类荧光探针及其制备和应用 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB970978A (forum.php) * | ||||
| FR1085028A (fr) * | 1952-10-08 | 1955-01-26 | Lepetit Spa | Procédé pour la préparation de cycloalcoylidène-hydrazides des acides monocarboxyliques |
| GB904681A (en) * | 1959-11-05 | 1962-08-29 | Warner Lambert Pharmaceutical | Substituted hydrazines and process for their preparation |
| GB924600A (en) * | 1960-06-09 | 1963-04-24 | Smith & Nephew | Substituted benzyl hydrazines and semicarbazides and processes for making them |
| US3654294A (en) * | 1967-07-27 | 1972-04-04 | R & L Molecular Research Ltd | Certain isothiazolylacetylenemercaptides |
| GB1268907A (en) * | 1968-12-10 | 1972-03-29 | Ciba Geigy U K Ltd | Novel dihydrazides and their preparation |
| DE2122572A1 (de) * | 1971-05-07 | 1972-11-23 | Farbenfabriken Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von neuen Derivaten von 2-Formyl-3-carbonatnido-chinoxalin-di-N-oxiden sowie ihre Verwendung als Arzneimittel und Futtermittelzusatz |
| US3862116A (en) * | 1972-01-03 | 1975-01-21 | Du Pont | Dehydrothio-p-toluidinesulfonic acid azo-hexahydro-4,6-dioxopyrimidineurea or cyanamide direct dyes for paper |
| US3855276A (en) * | 1973-12-17 | 1974-12-17 | American Cyanamid Co | Phenanthryl ethylidene carbazic acid esters |
| US3856838A (en) * | 1973-12-17 | 1974-12-24 | American Cyanamid Co | Beta-naphthyl alkylidene carbazic acid esters |
| US3852334A (en) * | 1973-12-17 | 1974-12-03 | American Cyanamid Co | Substituted carbazic acid esters |
| US3867425A (en) * | 1974-01-09 | 1975-02-18 | American Cyanamid Co | Substituted benzyl carbazic acid esters |
| DE2422548C2 (de) * | 1974-05-09 | 1982-08-26 | Bayer Ag, 5090 Leverkusen | 0-Triazolyl-(thiono)-phosphor(phosphon)-säureester und -esteramide, Verfahren zu ihrer Herstellung sowieihre Verwendung als Insektizide, Akarizide und Nematizide |
| HU171738B (hu) * | 1975-03-14 | 1978-03-28 | Egyt Gyogyszervegyeszeti Gyar | Sposob poluchenija proizvodnykh kinoksalin-1,4-dioksid-azometina |
| GB1504151A (en) * | 1975-04-17 | 1978-03-15 | Ici Ltd | Methods using and compositions containing quinone derivatives for use in animal husbandry |
| US4041070A (en) * | 1976-07-14 | 1977-08-09 | American Cyanamid Company | Tetrahydro-4-imino-1-naphthylureas |
| US4236017A (en) * | 1979-07-27 | 1980-11-25 | Montedison S.P.A., | Process for synthesizing 2-substituted semicarbazones and carbalkoxy hydrazones |
| GB2058057A (en) * | 1979-08-31 | 1981-04-08 | Boots Co Ltd | Pesticidal substituted benzophenone hydrazones |
| HU190384B (en) * | 1982-05-04 | 1986-08-28 | Egyt Gyogyszervegyeszeti Gyar,Hu | Process for preparing cycloalkane derivatives and compositions for weight increasing containing such compounds |
-
1982
- 1982-05-04 HU HU821381A patent/HU190795B/hu not_active IP Right Cessation
-
1983
- 1983-04-26 FI FI831429A patent/FI78815C/fi not_active IP Right Cessation
- 1983-04-28 YU YU965/83A patent/YU42855B/xx unknown
- 1983-05-02 CH CH2347/83A patent/CH659244A5/de not_active IP Right Cessation
- 1983-05-02 BE BE1/10780A patent/BE896629A/fr not_active IP Right Cessation
- 1983-05-02 SE SE8302481A patent/SE8302481L/ not_active Application Discontinuation
- 1983-05-03 DK DK196983A patent/DK196983A/da not_active Application Discontinuation
- 1983-05-03 NL NL8301544A patent/NL8301544A/nl not_active Application Discontinuation
- 1983-05-03 FR FR838307327A patent/FR2526424B1/fr not_active Expired
- 1983-05-03 AT AT0162583A patent/AT384804B/de not_active IP Right Cessation
- 1983-05-03 CA CA000427272A patent/CA1194885A/en not_active Expired
- 1983-05-03 ES ES522058A patent/ES8501370A1/es not_active Expired
- 1983-05-03 IT IT20921/83A patent/IT1221914B/it active
- 1983-05-03 GB GB08312050A patent/GB2119381B/en not_active Expired
- 1983-05-03 PL PL1983241758A patent/PL138376B1/pl unknown
- 1983-05-03 AR AR292911A patent/AR231531A1/es active
- 1983-05-03 GR GR71281A patent/GR78250B/el unknown
- 1983-05-03 PH PH28846A patent/PH19991A/en unknown
- 1983-05-03 AU AU14192/83A patent/AU565379B2/en not_active Ceased
- 1983-05-04 DE DE19833316316 patent/DE3316316A1/de not_active Withdrawn
- 1983-05-04 JP JP58077653A patent/JPS5936655A/ja active Pending
- 1983-05-04 CS CS833169A patent/CS240967B2/cs unknown
- 1983-05-04 SU SU833593065A patent/SU1299503A3/ru active
- 1983-05-04 DD DD83250605A patent/DD209812A5/de not_active IP Right Cessation
-
1984
- 1984-01-24 US US06/573,586 patent/US4570002A/en not_active Expired - Fee Related
-
1985
- 1985-05-23 US US06/737,388 patent/US4618623A/en not_active Expired - Fee Related
-
1986
- 1986-10-06 AT AT0263986A patent/AT387891B/de not_active IP Right Cessation
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| Date | Code | Title | Description |
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| ENJ | Ceased due to non-payment of renewal fee |