NO134239B - - Google Patents
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- Publication number
- NO134239B NO134239B NO1986/71A NO198671A NO134239B NO 134239 B NO134239 B NO 134239B NO 1986/71 A NO1986/71 A NO 1986/71A NO 198671 A NO198671 A NO 198671A NO 134239 B NO134239 B NO 134239B
- Authority
- NO
- Norway
- Prior art keywords
- isoflavone
- melting point
- compounds
- effect
- active ingredient
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000000654 additive Substances 0.000 claims description 10
- 239000002243 precursor Substances 0.000 claims description 8
- SFBODOKJTYAUCM-UHFFFAOYSA-N Ipriflavone Chemical compound C=1C(OC(C)C)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 SFBODOKJTYAUCM-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- -1 nitro, sulfo Chemical group 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001589 carboacyl group Chemical group 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- SJMVMVDTJPFWRU-UHFFFAOYSA-N 7-[(4-nitrophenyl)methoxy]-3-phenylchromen-4-one Chemical compound C1=CC([N+](=O)[O-])=CC=C1COC1=CC=C2C(=O)C(C=3C=CC=CC=3)=COC2=C1 SJMVMVDTJPFWRU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000002844 melting Methods 0.000 description 32
- 230000008018 melting Effects 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 241001465754 Metazoa Species 0.000 description 21
- 230000000694 effects Effects 0.000 description 20
- 230000037396 body weight Effects 0.000 description 17
- 239000000203 mixture Substances 0.000 description 17
- 239000000243 solution Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 241000700159 Rattus Species 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000001076 estrogenic effect Effects 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 10
- 150000002515 isoflavone derivatives Chemical class 0.000 description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- 238000011835 investigation Methods 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000001965 increasing effect Effects 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- WMKOZARWBMFKAS-UHFFFAOYSA-N 7-hydroxyisoflavone Chemical compound C=1C(O)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 WMKOZARWBMFKAS-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 206010067572 Oestrogenic effect Diseases 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 230000004584 weight gain Effects 0.000 description 6
- 235000019786 weight gain Nutrition 0.000 description 6
- UGTLQORHXBTVEQ-UHFFFAOYSA-N 7-butoxy-3-phenylchromen-4-one Chemical compound C=1C(OCCCC)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 UGTLQORHXBTVEQ-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 241000287828 Gallus gallus Species 0.000 description 5
- 230000001195 anabolic effect Effects 0.000 description 5
- 235000013330 chicken meat Nutrition 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 229910052791 calcium Inorganic materials 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 230000000384 rearing effect Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ROSLGMBGAIDTPC-UHFFFAOYSA-N 1,3-bis(2-hydroxy-4-propan-2-yloxyphenyl)-1,3-diphenylpropan-2-one Chemical compound OC1=CC(OC(C)C)=CC=C1C(C=1C=CC=CC=1)C(=O)C(C=1C(=CC(OC(C)C)=CC=1)O)C1=CC=CC=C1 ROSLGMBGAIDTPC-UHFFFAOYSA-N 0.000 description 3
- CCOKRTXERADBIO-UHFFFAOYSA-N 1,3-bis(4-butoxy-2-hydroxyphenyl)-1,3-diphenylpropan-2-one Chemical compound OC1=CC(OCCCC)=CC=C1C(C=1C=CC=CC=1)C(=O)C(C=1C(=CC(OCCCC)=CC=1)O)C1=CC=CC=C1 CCOKRTXERADBIO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 235000019742 Vitamins premix Nutrition 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 3
- 229960003529 diazepam Drugs 0.000 description 3
- 230000029142 excretion Effects 0.000 description 3
- 238000009313 farming Methods 0.000 description 3
- 235000013312 flour Nutrition 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229930012930 isoflavone derivative Natural products 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 3
- 239000010452 phosphate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 238000007920 subcutaneous administration Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- 230000009182 swimming Effects 0.000 description 3
- ANTPLZFFFWCICZ-UHFFFAOYSA-N 2-methyl-3-phenyl-7-phenylmethoxychromen-4-one Chemical compound C=1C=C2C(=O)C(C=3C=CC=CC=3)=C(C)OC2=CC=1OCC1=CC=CC=C1 ANTPLZFFFWCICZ-UHFFFAOYSA-N 0.000 description 2
- PCCKAQNSDCEGBC-UHFFFAOYSA-N 2-methyl-3-phenyl-7-propan-2-yloxychromen-4-one Chemical compound C=1C(OC(C)C)=CC=C(C2=O)C=1OC(C)=C2C1=CC=CC=C1 PCCKAQNSDCEGBC-UHFFFAOYSA-N 0.000 description 2
- BBCDTCKKROIGAB-UHFFFAOYSA-N 7-Hydroxy-2-methylisoflavone Chemical compound CC=1OC2=CC(O)=CC=C2C(=O)C=1C1=CC=CC=C1 BBCDTCKKROIGAB-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000019750 Crude protein Nutrition 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 235000019733 Fish meal Nutrition 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- DPCMZUHKNHLUKT-UHFFFAOYSA-N OC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 Chemical class OC=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 DPCMZUHKNHLUKT-UHFFFAOYSA-N 0.000 description 2
- 208000001132 Osteoporosis Diseases 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- 101710124728 Protein 19.5 Proteins 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003263 anabolic agent Substances 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000001548 androgenic effect Effects 0.000 description 2
- 238000010171 animal model Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009395 breeding Methods 0.000 description 2
- 230000001488 breeding effect Effects 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000004467 fishmeal Substances 0.000 description 2
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229960005431 ipriflavone Drugs 0.000 description 2
- CJWQYWQDLBZGPD-UHFFFAOYSA-N isoflavone Natural products C1=C(OC)C(OC)=CC(OC)=C1C1=COC2=C(C=CC(C)(C)O3)C3=C(OC)C=C2C1=O CJWQYWQDLBZGPD-UHFFFAOYSA-N 0.000 description 2
- 235000008696 isoflavones Nutrition 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229930182817 methionine Natural products 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 235000016709 nutrition Nutrition 0.000 description 2
- 230000035764 nutrition Effects 0.000 description 2
- 210000000056 organ Anatomy 0.000 description 2
- 238000009304 pastoral farming Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- 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 2
- 230000007306 turnover Effects 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- PCXVKRLGYPNMKJ-UHFFFAOYSA-N (5-acetyloxy-2-methyl-4-oxo-3-phenylchromen-7-yl) acetate Chemical compound C=1C(OC(=O)C)=CC(OC(C)=O)=C(C2=O)C=1OC(C)=C2C1=CC=CC=C1 PCXVKRLGYPNMKJ-UHFFFAOYSA-N 0.000 description 1
- WYMYJTSWNPZKHM-UHFFFAOYSA-N 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone Chemical compound OC1=CC(OC)=CC=C1C(=O)CC1=CC=CC=C1 WYMYJTSWNPZKHM-UHFFFAOYSA-N 0.000 description 1
- INKNHBKFSPIMKS-UHFFFAOYSA-N 1-(iodomethyl)-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(CI)C=C1 INKNHBKFSPIMKS-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 1
- UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- WSUOZOGQANJFSP-UHFFFAOYSA-N 2-methyl-3-phenyl-7-propoxychromen-4-one Chemical compound C=1C(OCCC)=CC=C(C2=O)C=1OC(C)=C2C1=CC=CC=C1 WSUOZOGQANJFSP-UHFFFAOYSA-N 0.000 description 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 description 1
- YPZVSKLCKHLPOH-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-7-(2-ethoxyethoxy)-2-methylchromen-4-one Chemical compound C=1C(OCCOCC)=CC=C(C2=O)C=1OC(C)=C2C1=CC=C(OC)C(OC)=C1 YPZVSKLCKHLPOH-UHFFFAOYSA-N 0.000 description 1
- AOTCTMIPOGWDRM-UHFFFAOYSA-N 3-(3,4-dimethoxyphenyl)-7-(2-hydroxyethoxy)chromen-4-one Chemical compound C1=C(OC)C(OC)=CC=C1C1=COC2=CC(OCCO)=CC=C2C1=O AOTCTMIPOGWDRM-UHFFFAOYSA-N 0.000 description 1
- MTWVQPZFIMUYQQ-UHFFFAOYSA-N 3-phenyl-7-propoxychromen-4-one Chemical compound C=1C(OCCC)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 MTWVQPZFIMUYQQ-UHFFFAOYSA-N 0.000 description 1
- MXFHUAREZRSXMW-UHFFFAOYSA-N 5,7-dihydroxy-2-methyl-3-phenylchromen-4-one Chemical compound CC=1OC2=CC(O)=CC(O)=C2C(=O)C=1C1=CC=CC=C1 MXFHUAREZRSXMW-UHFFFAOYSA-N 0.000 description 1
- FUTDGSLPTJOHRU-UHFFFAOYSA-N 7-(2-ethoxyethoxy)-2-methyl-3-phenylchromen-4-one Chemical compound C=1C(OCCOCC)=CC=C(C2=O)C=1OC(C)=C2C1=CC=CC=C1 FUTDGSLPTJOHRU-UHFFFAOYSA-N 0.000 description 1
- CYHIOMLTMVDTEG-UHFFFAOYSA-N 7-(2-ethoxyethoxy)-3-phenylchromen-4-one Chemical compound C=1C(OCCOCC)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 CYHIOMLTMVDTEG-UHFFFAOYSA-N 0.000 description 1
- YHOVOFWAWRPGKP-UHFFFAOYSA-N 7-(2-hydroxyethoxy)-3-phenylchromen-4-one Chemical compound C=1C(OCCO)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 YHOVOFWAWRPGKP-UHFFFAOYSA-N 0.000 description 1
- FCCHLEMIHIORFS-UHFFFAOYSA-N 7-(3-chloropropoxy)-3-phenylchromen-4-one Chemical compound C=1C(OCCCCl)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 FCCHLEMIHIORFS-UHFFFAOYSA-N 0.000 description 1
- IXIOBOGKPFCHFD-UHFFFAOYSA-N 7-[(4-chlorophenyl)methoxy]-2-methyl-3-phenylchromen-4-one Chemical compound C=1C=C2C(=O)C(C=3C=CC=CC=3)=C(C)OC2=CC=1OCC1=CC=C(Cl)C=C1 IXIOBOGKPFCHFD-UHFFFAOYSA-N 0.000 description 1
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- IDKRUDUYTUQYKK-UHFFFAOYSA-N 7-butoxy-2-methyl-3-phenylchromen-4-one Chemical compound C=1C(OCCCC)=CC=C(C2=O)C=1OC(C)=C2C1=CC=CC=C1 IDKRUDUYTUQYKK-UHFFFAOYSA-N 0.000 description 1
- RDHOMIWPBOEDIW-UHFFFAOYSA-N 7-hexoxy-2-methyl-3-phenylchromen-4-one Chemical compound C=1C(OCCCCCC)=CC=C(C2=O)C=1OC(C)=C2C1=CC=CC=C1 RDHOMIWPBOEDIW-UHFFFAOYSA-N 0.000 description 1
- VDWJVKIWHSYPNG-UHFFFAOYSA-N 7-hexoxy-3-phenylchromen-4-one Chemical compound C=1C(OCCCCCC)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 VDWJVKIWHSYPNG-UHFFFAOYSA-N 0.000 description 1
- AKCARYLMYMMQGQ-UHFFFAOYSA-N 7-methoxy-4-oxo-3-phenylchromene-2-carboxylic acid Chemical compound C=1C(OC)=CC=C(C2=O)C=1OC(C(O)=O)=C2C1=CC=CC=C1 AKCARYLMYMMQGQ-UHFFFAOYSA-N 0.000 description 1
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 235000019743 Choline chloride Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 1
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- 241000699800 Cricetinae Species 0.000 description 1
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- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 238000007696 Kjeldahl method Methods 0.000 description 1
- 235000010624 Medicago sativa Nutrition 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 231100000229 OECD 452 Chronic Toxicity Study Toxicity 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 208000008425 Protein deficiency Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000000692 Student's t-test Methods 0.000 description 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 description 1
- 241000219793 Trifolium Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940124325 anabolic agent Drugs 0.000 description 1
- 229940070021 anabolic steroids Drugs 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 238000003975 animal breeding Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003160 anti-catabolic effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 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
- 230000004071 biological effect Effects 0.000 description 1
- 238000004159 blood analysis Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- 231100000160 chronic toxicity Toxicity 0.000 description 1
- 230000007665 chronic toxicity Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 229960004544 cortisone Drugs 0.000 description 1
- 235000007240 daidzein Nutrition 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002124 endocrine Effects 0.000 description 1
- 210000003372 endocrine gland Anatomy 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- OWZFULPEVHKEKS-UHFFFAOYSA-N ethyl 2-chloro-2-oxoacetate Chemical compound CCOC(=O)C(Cl)=O OWZFULPEVHKEKS-UHFFFAOYSA-N 0.000 description 1
- SKNJZPZRJOUDOZ-UHFFFAOYSA-N ethyl 3-(3,4-dimethoxyphenyl)-2-methoxy-4-oxochromene-7-carboxylate Chemical compound C=1C(C(=O)OCC)=CC=C(C2=O)C=1OC(OC)=C2C1=CC=C(OC)C(OC)=C1 SKNJZPZRJOUDOZ-UHFFFAOYSA-N 0.000 description 1
- KSOXGOZMJVXJIK-UHFFFAOYSA-N ethyl 7-methoxy-4-oxo-3-phenylchromene-2-carboxylate Chemical compound CCOC(=O)C=1OC2=CC(OC)=CC=C2C(=O)C=1C1=CC=CC=C1 KSOXGOZMJVXJIK-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930003944 flavone Natural products 0.000 description 1
- 150000002212 flavone derivatives Chemical class 0.000 description 1
- 235000011949 flavones Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- TZBJGXHYKVUXJN-UHFFFAOYSA-N genistein Natural products C1=CC(O)=CC=C1C1=COC2=CC(O)=CC(O)=C2C1=O TZBJGXHYKVUXJN-UHFFFAOYSA-N 0.000 description 1
- 235000006539 genistein Nutrition 0.000 description 1
- 229940045109 genistein Drugs 0.000 description 1
- ZCOLJUOHXJRHDI-CMWLGVBASA-N genistein 7-O-beta-D-glucoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=C2C(=O)C(C=3C=CC(O)=CC=3)=COC2=C1 ZCOLJUOHXJRHDI-CMWLGVBASA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000036732 histological change Effects 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 230000003054 hormonal effect Effects 0.000 description 1
- 231100000508 hormonal effect Toxicity 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000003100 immobilizing effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- GOMNOOKGLZYEJT-UHFFFAOYSA-N isoflavone Chemical compound C=1OC2=CC=CC=C2C(=O)C=1C1=CC=CC=C1 GOMNOOKGLZYEJT-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000015255 meat loaf Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 239000000401 methanolic extract Substances 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
- 238000000465 moulding Methods 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000009372 pisciculture Methods 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- LBUSGXDHOHEPQQ-UHFFFAOYSA-N propane-1,1,1-triol Chemical compound CCC(O)(O)O LBUSGXDHOHEPQQ-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 231100000456 subacute toxicity Toxicity 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 231100000820 toxicity test Toxicity 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- GTLDTDOJJJZVBW-UHFFFAOYSA-N zinc cyanide Chemical compound [Zn+2].N#[C-].N#[C-] GTLDTDOJJJZVBW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- 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
- A23K20/121—Heterocyclic compounds containing oxygen or sulfur as hetero 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
- A23K20/137—Heterocyclic compounds containing two hetero atoms, of which at least one is nitrogen
-
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Zoology (AREA)
- Animal Husbandry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Birds (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fodder In General (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUCI996A HU162377B (sv) | 1970-05-27 | 1970-05-27 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134239B true NO134239B (sv) | 1976-05-31 |
| NO134239C NO134239C (sv) | 1976-09-08 |
Family
ID=10994379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO1986/71A NO134239C (sv) | 1970-05-27 | 1971-05-26 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3833730A (sv) |
| JP (3) | JPS5413391B1 (sv) |
| AT (3) | AT311778B (sv) |
| BG (1) | BG21260A1 (sv) |
| CA (1) | CA998057A (sv) |
| CH (2) | CH567499A5 (sv) |
| CS (3) | CS165840B1 (sv) |
| DE (3) | DE2166458A1 (sv) |
| DK (1) | DK137362B (sv) |
| EG (1) | EG10589A (sv) |
| ES (3) | ES391486A1 (sv) |
| FI (1) | FI57406C (sv) |
| FR (1) | FR2100692B1 (sv) |
| GB (2) | GB1360461A (sv) |
| HU (1) | HU162377B (sv) |
| IL (1) | IL36929A (sv) |
| NL (1) | NL170539C (sv) |
| NO (1) | NO134239C (sv) |
| PL (3) | PL98591B1 (sv) |
| RO (1) | RO62749A (sv) |
| SE (2) | SE389001B (sv) |
| SU (2) | SU402176A3 (sv) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3949085A (en) * | 1970-05-27 | 1976-04-06 | Chinoin Gyogyszer-Es Vegyeszeti Termakek Gyara Rt | Anabolic-weight-gain promoting compositions containing isoflavone derivatives and method using same |
| US4166862A (en) * | 1971-05-25 | 1979-09-04 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt. | Animal feed containing anabolic isoflavones |
| HU166380B (sv) * | 1973-07-09 | 1975-03-28 | ||
| US4117149A (en) * | 1975-09-12 | 1978-09-26 | Pfizer Inc. | 4-oxo-4h-benzopyrans as animal growth promotants |
| SU997646A1 (ru) * | 1978-11-27 | 1983-02-23 | Ордена Трудового Красного Знамени Институт Органического Синтеза Ан Латвсср | Кормова добавка |
| JPS59199630A (ja) * | 1983-04-26 | 1984-11-12 | Takeda Chem Ind Ltd | 卵巣機能低下症治療剤 |
| JPS6054379A (ja) * | 1983-09-05 | 1985-03-28 | Takeda Chem Ind Ltd | 新規４ｈ−１−ベンゾピラン−４−オン誘導体，その製法および用途 |
| ZA873745B (en) * | 1986-06-04 | 1988-10-26 | Daiichi Seiyaku Co | Benzopyran derivatives |
| IT1241079B (it) * | 1990-03-23 | 1993-12-29 | Chiesi Farma Spa | Composizioni farmaceutiche contenenti ipriflavone,procedimento per la loro preparazione e relativo impiego terapeutico |
| DE69006502T2 (de) * | 1990-04-06 | 1994-05-19 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt., Budapest | Verbessertes verfahren zur darstellung substituierter isoflavonderivate. |
| ATE169924T1 (de) * | 1993-05-18 | 1998-09-15 | Takeda Chemical Industries Ltd | Benzopyran-derivate und ihre verwendung |
| HUT68396A (en) * | 1993-07-20 | 1995-04-25 | Chinoin Gyogyszer Es Vegyeszet | Method for preparing pharmaceutical preparation containing isoflavone derivative or salt of it |
| HU212932B (en) * | 1993-08-02 | 1996-12-30 | Chinoin Gyogyszer Es Vegyeszet | Parmaceutical composition containing ipriflavone, hydroxyapatit and tricalciumphosphate for treating lack of bones and process for producing the composition |
| IT1289154B1 (it) * | 1997-01-03 | 1998-09-29 | Chiesi Farma Spa | Derivati di isoflavone loro preparazione e loro impiego terapeutico |
| US5981775A (en) * | 1998-09-16 | 1999-11-09 | Board Of Trustees Operating Michigan State University | Process for the preparation of isoflavones |
| GB0412768D0 (en) * | 2004-06-08 | 2004-07-07 | Novartis Ag | Organic compounds |
| DE102007062199A1 (de) * | 2007-12-21 | 2009-06-25 | Evonik Degussa Gmbh | 2-Methylthioethyl-substituierte Heterocyclen als Futtermitteladditive |
| MX2010008111A (es) * | 2008-01-24 | 2010-11-30 | Endowment For Res In Human Biology Inc | Inhibidores de aldh-2 en el tratamiento de adicciones. |
| CN102715353A (zh) * | 2012-05-11 | 2012-10-10 | 北京农学院 | 植物多酚类化合物在畜禽养殖中的应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE586723A (fr) * | 1960-01-19 | 1960-07-19 | Sarec S A | Nouveaux composes chimiques et thérapeutiques dérives des isoflavones, et leurs procédés de préparation. |
| FR1370795A (fr) * | 1963-07-17 | 1964-08-28 | Chimie Et Synthese De Picardie | Procédé de préparation de benzo-gamma-pyrones substituées en 3 |
-
1970
- 1970-05-27 HU HUCI996A patent/HU162377B/hu unknown
-
1971
- 1971-05-20 IL IL36929A patent/IL36929A/xx unknown
- 1971-05-21 DE DE19712166458 patent/DE2166458A1/de active Pending
- 1971-05-21 DE DE2125245A patent/DE2125245C3/de not_active Expired
- 1971-05-21 DE DE2166085A patent/DE2166085C3/de not_active Expired
- 1971-05-22 EG EG218/71A patent/EG10589A/xx active
- 1971-05-24 ES ES391486A patent/ES391486A1/es not_active Expired
- 1971-05-24 AT AT1028171A patent/AT311778B/de active
- 1971-05-24 AT AT0444/71*[A patent/AT311342B/de not_active IP Right Cessation
- 1971-05-24 AT AT690972A patent/AT318613B/de not_active IP Right Cessation
- 1971-05-25 NL NLAANVRAGE7107128,A patent/NL170539C/xx not_active IP Right Cessation
- 1971-05-25 SE SE7106745A patent/SE389001B/sv unknown
- 1971-05-25 US US00146773A patent/US3833730A/en not_active Expired - Lifetime
- 1971-05-26 GB GB1729371A patent/GB1360461A/en not_active Expired
- 1971-05-26 DK DK254371AA patent/DK137362B/da not_active IP Right Cessation
- 1971-05-26 SU SU1667729A patent/SU402176A3/ru active
- 1971-05-26 PL PL1971148411A patent/PL98591B1/pl unknown
- 1971-05-26 CH CH770471A patent/CH567499A5/xx not_active IP Right Cessation
- 1971-05-26 CH CH606874A patent/CH565786A5/xx not_active IP Right Cessation
- 1971-05-26 NO NO1986/71A patent/NO134239C/no unknown
- 1971-05-26 PL PL1971175267A patent/PL99030B1/pl unknown
- 1971-05-26 GB GB158374A patent/GB1360462A/en not_active Expired
- 1971-05-26 BG BG18841A patent/BG21260A1/xx unknown
- 1971-05-26 PL PL1971160121A patent/PL84997B1/pl unknown
- 1971-05-26 SU SU1717079A patent/SU508205A3/ru active
- 1971-05-27 JP JP3594071A patent/JPS5413391B1/ja active Pending
- 1971-05-27 FR FR7119257A patent/FR2100692B1/fr not_active Expired
- 1971-05-27 CA CA114,041A patent/CA998057A/en not_active Expired
- 1971-05-27 FI FI1463/71A patent/FI57406C/fi active
- 1971-05-27 CS CS4398*A patent/CS165840B1/cs unknown
- 1971-05-27 CS CS6392*A patent/CS165839B1/cs unknown
- 1971-05-27 CS CS388871A patent/CS157871B1/cs unknown
- 1971-05-27 RO RO70509A patent/RO62749A/ro unknown
- 1971-12-23 ES ES398289A patent/ES398289A1/es not_active Expired
-
1974
- 1974-05-02 ES ES425900A patent/ES425900A1/es not_active Expired
- 1974-06-04 SE SE7407325A patent/SE412586B/sv not_active IP Right Cessation
-
1977
- 1977-09-27 JP JP52115994A patent/JPS593998B2/ja not_active Expired
-
1982
- 1982-12-10 JP JP57216782A patent/JPS5925791B2/ja not_active Expired
Also Published As
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