JPS6031831B2 - ７−置換−８−アミノメチル−イソフラボン誘導体の製造方法 - Google Patents
７−置換−８−アミノメチル−イソフラボン誘導体の製造方法Info
- Publication number
- JPS6031831B2 JPS6031831B2 JP50052599A JP5259975A JPS6031831B2 JP S6031831 B2 JPS6031831 B2 JP S6031831B2 JP 50052599 A JP50052599 A JP 50052599A JP 5259975 A JP5259975 A JP 5259975A JP S6031831 B2 JPS6031831 B2 JP S6031831B2
- Authority
- JP
- Japan
- Prior art keywords
- isoflavone
- general formula
- group
- isopropoxy
- formula
- 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.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- -1 7-substituted-8-aminomethyl-isoflavone Chemical class 0.000 title description 25
- 150000001875 compounds Chemical class 0.000 claims description 45
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- 238000007265 chloromethylation reaction Methods 0.000 claims description 2
- 235000019260 propionic acid Nutrition 0.000 claims description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 65
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- 239000000203 mixture Substances 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 239000000243 solution Substances 0.000 description 30
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 239000013078 crystal Substances 0.000 description 21
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 17
- 239000000725 suspension Substances 0.000 description 17
- 239000000843 powder Substances 0.000 description 14
- 238000009835 boiling Methods 0.000 description 13
- 235000001968 nicotinic acid Nutrition 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000011664 nicotinic acid Substances 0.000 description 12
- 241001465754 Metazoa Species 0.000 description 10
- VTKOIVKQOOIMEJ-UHFFFAOYSA-N 8-(morpholin-4-ylmethyl)-3-phenyl-7-propan-2-yloxychromen-4-one Chemical compound CC(C)OC1=CC=C2C(=O)C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1 VTKOIVKQOOIMEJ-UHFFFAOYSA-N 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 8
- 239000004480 active ingredient Substances 0.000 description 8
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 229960003512 nicotinic acid Drugs 0.000 description 6
- 235000013343 vitamin Nutrition 0.000 description 6
- 239000011782 vitamin Substances 0.000 description 6
- 229940088594 vitamin Drugs 0.000 description 6
- 229930003231 vitamin Natural products 0.000 description 6
- GIBWIWCQZADDCC-UHFFFAOYSA-N 7-hexadecoxy-8-(morpholin-4-ylmethyl)-3-phenylchromen-4-one Chemical compound CCCCCCCCCCCCCCCCOC1=CC=C2C(=O)C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1 GIBWIWCQZADDCC-UHFFFAOYSA-N 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RAULIAHRYVMDHP-UHFFFAOYSA-N 7-methoxy-8-(morpholin-4-ylmethyl)-3-phenylchromen-4-one Chemical compound COC1=CC=C2C(=O)C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1 RAULIAHRYVMDHP-UHFFFAOYSA-N 0.000 description 4
- QFOILJZOWCPCGC-UHFFFAOYSA-N 8-(chloromethyl)-3-phenyl-7-propan-2-yloxychromen-4-one Chemical compound ClCC=1C(OC(C)C)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 QFOILJZOWCPCGC-UHFFFAOYSA-N 0.000 description 4
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 4
- 235000019742 Vitamins premix Nutrition 0.000 description 4
- 239000003674 animal food additive Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 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 4
- 235000008696 isoflavones Nutrition 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 239000008194 pharmaceutical composition Substances 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 150000003722 vitamin derivatives Chemical class 0.000 description 4
- 239000011592 zinc chloride Substances 0.000 description 4
- 235000005074 zinc chloride Nutrition 0.000 description 4
- LEGMBEQCGGUNGX-UHFFFAOYSA-N 3-phenyl-7-propan-2-yloxy-8-(pyrrolidin-1-ylmethyl)chromen-4-one Chemical compound CC(C)OC1=CC=C2C(=O)C(=COC2=C1CN1CCCC1)C1=CC=CC=C1 LEGMBEQCGGUNGX-UHFFFAOYSA-N 0.000 description 3
- LNSBUEBEDMIYIC-UHFFFAOYSA-N 8-(chloromethyl)-7-methoxy-3-phenylchromen-4-one Chemical compound ClCC=1C(OC)=CC=C(C2=O)C=1OC=C2C1=CC=CC=C1 LNSBUEBEDMIYIC-UHFFFAOYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229940050410 gluconate Drugs 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- ZLACZVOVAPXJCV-UHFFFAOYSA-N 7-hexadecoxy-8-(morpholin-4-ylmethyl)-3-phenylchromen-4-one hydrochloride Chemical compound Cl.CCCCCCCCCCCCCCCCOC1=CC=C2C(=O)C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1 ZLACZVOVAPXJCV-UHFFFAOYSA-N 0.000 description 2
- YUDHPJZWEQJREQ-UHFFFAOYSA-N 7-methoxy-8-(morpholin-4-ylmethyl)-3-phenylchromen-4-one hydrochloride Chemical compound Cl.COC1=CC=C2C(=O)C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1 YUDHPJZWEQJREQ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JCSUKZFMRRZJHT-UHFFFAOYSA-N C(C1=CN=CC=C1)(=O)O.C(C)(C)OC1=CC=C2C(C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1)=O Chemical compound C(C1=CN=CC=C1)(=O)O.C(C)(C)OC1=CC=C2C(C(=COC2=C1CN1CCOCC1)C1=CC=CC=C1)=O JCSUKZFMRRZJHT-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000282693 Cercopithecidae Species 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000019750 Crude protein Nutrition 0.000 description 2
- 235000019733 Fish meal Nutrition 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 244000068988 Glycine max Species 0.000 description 2
- 235000010469 Glycine max Nutrition 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 240000004658 Medicago sativa Species 0.000 description 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 2
- QXRXXHZHMSFPAO-UHFFFAOYSA-N O1CCN(CC1)CC=1C=CC=C2C(C(=COC12)C1=CC=CC=C1)=O Chemical compound O1CCN(CC1)CC=1C=CC=C2C(C(=COC12)C1=CC=CC=C1)=O QXRXXHZHMSFPAO-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 229930003270 Vitamin B Natural products 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
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 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
- 238000006243 chemical reaction Methods 0.000 description 2
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- 239000003085 diluting agent Substances 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000004467 fishmeal Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 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
- 230000002438 mitochondrial effect Effects 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- GNTPADWHXGNJPC-UHFFFAOYSA-N pyridine-3-carboxylic acid;hydrate Chemical compound O.OC(=O)C1=CC=CN=C1 GNTPADWHXGNJPC-UHFFFAOYSA-N 0.000 description 2
- SMUQFGGVLNAIOZ-UHFFFAOYSA-N quinaldine Chemical compound C1=CC=CC2=NC(C)=CC=C21 SMUQFGGVLNAIOZ-UHFFFAOYSA-N 0.000 description 2
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- 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
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- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
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- 239000001763 2-hydroxyethyl(trimethyl)azanium Substances 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
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- 230000001488 breeding effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 229960003178 choline chloride Drugs 0.000 description 1
- SGMZJAMFUVOLNK-UHFFFAOYSA-M choline chloride Chemical compound [Cl-].C[N+](C)(C)CCO SGMZJAMFUVOLNK-UHFFFAOYSA-M 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000000378 dietary effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 230000001729 effect on metabolism Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 239000000262 estrogen Substances 0.000 description 1
- 229940011871 estrogen Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000008713 feedback mechanism Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- PLHJDBGFXBMTGZ-WEVVVXLNSA-N furazolidone Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)OCC1 PLHJDBGFXBMTGZ-WEVVVXLNSA-N 0.000 description 1
- 229960001625 furazolidone Drugs 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000002414 glycolytic effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 230000007954 hypoxia Effects 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 229960005431 ipriflavone Drugs 0.000 description 1
- 229910052742 iron Inorganic materials 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
- 150000007517 lewis acids Chemical class 0.000 description 1
- 210000002311 liver mitochondria Anatomy 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 210000003470 mitochondria Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000010627 oxidative phosphorylation Effects 0.000 description 1
- 235000020232 peanut Nutrition 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 210000001685 thyroid gland Anatomy 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 235000019168 vitamin K Nutrition 0.000 description 1
- 239000011712 vitamin K Substances 0.000 description 1
- 150000003721 vitamin K derivatives Chemical class 0.000 description 1
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940046010 vitamin k Drugs 0.000 description 1
- 230000003442 weekly effect Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1474/75 | 1974-05-03 | ||
| HUCI1474A HU168753B (cs) | 1974-05-03 | 1974-05-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS51125082A JPS51125082A (en) | 1976-11-01 |
| JPS6031831B2 true JPS6031831B2 (ja) | 1985-07-24 |
Family
ID=10994519
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50052599A Expired JPS6031831B2 (ja) | 1974-05-03 | 1975-05-02 | ７−置換−８−アミノメチル−イソフラボン誘導体の製造方法 |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS6031831B2 (cs) |
| AR (1) | AR205818A1 (cs) |
| AT (1) | AT344167B (cs) |
| CH (1) | CH611289A5 (cs) |
| CS (1) | CS183794B2 (cs) |
| DD (1) | DD119587A1 (cs) |
| DE (1) | DE2518986A1 (cs) |
| DK (1) | DK191375A (cs) |
| FI (1) | FI63568C (cs) |
| FR (1) | FR2269340B1 (cs) |
| GB (1) | GB1482238A (cs) |
| HU (1) | HU168753B (cs) |
| IL (1) | IL47196A (cs) |
| NL (1) | NL7505214A (cs) |
| NO (2) | NO147485C (cs) |
| PL (1) | PL99666B1 (cs) |
| SU (1) | SU576938A3 (cs) |
| YU (1) | YU37335B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2516921A1 (fr) * | 1981-11-25 | 1983-05-27 | Lipha | Haloalkyl-8-4h-(1) benzopyran-4-ones, et procedes de preparation |
| EP1477178A3 (en) | 1992-05-19 | 2005-02-16 | KELLY, Graham Edmund | Health supplements containing phyto-oestrogens, analogues or metabolites thereof |
| AUPO203996A0 (en) | 1996-08-30 | 1996-09-26 | Novogen Research Pty Ltd | Therapeutic uses |
| US6146668A (en) | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
| AUPP260798A0 (en) | 1998-03-26 | 1998-04-23 | Novogen Research Pty Ltd | Treatment of medical related conditions with isoflavone containing extracts of clover |
| AUPQ266199A0 (en) | 1999-09-06 | 1999-09-30 | Novogen Research Pty Ltd | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| AUPR363301A0 (en) | 2001-03-08 | 2001-04-05 | Novogen Research Pty Ltd | Dimeric isoflavones |
| CN101429186B (zh) * | 2007-11-08 | 2012-11-21 | 中国医学科学院药物研究所 | 松属素外消旋体的拆分方法 |
-
1974
- 1974-05-03 HU HUCI1474A patent/HU168753B/hu unknown
-
1975
- 1975-01-01 AR AR258616A patent/AR205818A1/es active
- 1975-04-28 FI FI751272A patent/FI63568C/fi not_active IP Right Cessation
- 1975-04-29 DE DE19752518986 patent/DE2518986A1/de not_active Ceased
- 1975-04-29 IL IL47196A patent/IL47196A/xx unknown
- 1975-04-30 AT AT332075A patent/AT344167B/de not_active IP Right Cessation
- 1975-04-30 SU SU7502132902A patent/SU576938A3/ru active
- 1975-04-30 YU YU1117/75A patent/YU37335B/xx unknown
- 1975-04-30 CS CS7500003024A patent/CS183794B2/cs unknown
- 1975-05-02 GB GB18523/75A patent/GB1482238A/en not_active Expired
- 1975-05-02 NL NL7505214A patent/NL7505214A/xx not_active Application Discontinuation
- 1975-05-02 JP JP50052599A patent/JPS6031831B2/ja not_active Expired
- 1975-05-02 NO NO751567A patent/NO147485C/no unknown
- 1975-05-02 PL PL1975180099A patent/PL99666B1/pl unknown
- 1975-05-02 DK DK191375A patent/DK191375A/da not_active Application Discontinuation
- 1975-05-02 CH CH564975A patent/CH611289A5/xx not_active IP Right Cessation
- 1975-05-05 FR FR7513942A patent/FR2269340B1/fr not_active Expired
- 1975-06-20 DD DD185801A patent/DD119587A1/xx unknown
-
1981
- 1981-03-18 NO NO810931A patent/NO151177C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU111775A (en) | 1983-04-27 |
| ATA332075A (de) | 1977-11-15 |
| NO751567L (cs) | 1975-11-04 |
| IL47196A (en) | 1978-07-31 |
| FR2269340B1 (cs) | 1980-01-25 |
| FR2269340A1 (cs) | 1975-11-28 |
| NO810931L (no) | 1975-11-04 |
| NO147485B (no) | 1983-01-10 |
| NO151177C (no) | 1985-02-27 |
| GB1482238A (en) | 1977-08-10 |
| NO147485C (no) | 1983-04-20 |
| DE2518986A1 (de) | 1975-11-20 |
| AT344167B (de) | 1978-07-10 |
| IL47196A0 (en) | 1975-06-25 |
| FI751272A7 (cs) | 1975-11-04 |
| FI63568B (fi) | 1983-03-31 |
| FI63568C (fi) | 1983-07-11 |
| YU37335B (en) | 1984-08-31 |
| HU168753B (cs) | 1976-07-28 |
| PL99666B1 (pl) | 1978-07-31 |
| AR205818A1 (es) | 1976-06-07 |
| JPS51125082A (en) | 1976-11-01 |
| NO151177B (no) | 1984-11-19 |
| CH611289A5 (en) | 1979-05-31 |
| DK191375A (da) | 1975-11-04 |
| SU576938A3 (ru) | 1977-10-15 |
| CS183794B2 (en) | 1978-07-31 |
| NL7505214A (nl) | 1975-11-05 |
| DD119587A1 (cs) | 1976-05-05 |
| AU8072375A (en) | 1976-11-04 |
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