NO801024L - Nye flavonderivater, fremstilling og preparater av disse - Google Patents

Nye flavonderivater, fremstilling og preparater av disse

Info

Publication number: NO801024L
Authority: NO; Norway
Prior art keywords: hydroxy; lower alkoxy; dihydroxy; alkoxy; acid
Prior art date: 1979-04-10

Application number

NO801024A

Other languages

English (en)

Norwegian (no)

Inventor

Hideo Ishitsuka

Haruyoshi Shirai

Isao Umeda

Yasuji Suhara

Original Assignee

Hoffmann La Roche

Priority date (The priority date 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 date listed.)

1979-04-10

Filing date

1980-04-09

Publication date

1980-10-13

1980-04-09 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1980-10-13 Publication of NO801024L publication Critical patent/NO801024L/no

Links

238000004519 manufacturing process Methods 0.000 title claims description 4
VHBFFQKBGNRLFZ-UHFFFAOYSA-N flavone Chemical class O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 title claims 2
238000002360 preparation method Methods 0.000 title description 2
-1 nicotinoyloxy Chemical group 0.000 claims description 26
125000003545 alkoxy group Chemical group 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
150000001875 compounds Chemical class 0.000 claims description 22
239000000203 mixture Substances 0.000 claims description 17
238000000034 method Methods 0.000 claims description 11
125000004423 acyloxy group Chemical group 0.000 claims description 9
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
239000000825 pharmaceutical preparation Substances 0.000 claims description 8
150000001991 dicarboxylic acids Chemical class 0.000 claims description 7
QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 claims description 6
125000003051 glycosyloxy group Chemical group 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
239000007787 solid Substances 0.000 claims description 5
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical class OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 4
238000006243 chemical reaction Methods 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
150000002772 monosaccharides Chemical class 0.000 claims description 3
DGIHNQMHJUSGBB-UHFFFAOYSA-N (4-acetamidobenzoyl) 4-acetamidobenzoate Chemical compound C1=CC(NC(=O)C)=CC=C1C(=O)OC(=O)C1=CC=C(NC(C)=O)C=C1 DGIHNQMHJUSGBB-UHFFFAOYSA-N 0.000 claims description 2
239000002253 acid Substances 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
239000012876 carrier material Substances 0.000 claims description 2
239000011664 nicotinic acid Chemical class 0.000 claims description 2
229960003512 nicotinic acid Drugs 0.000 claims description 2
235000001968 nicotinic acid Nutrition 0.000 claims description 2
AMZYHFOAWQBRRS-UHFFFAOYSA-N 3-ethoxy-5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-7-methoxychromen-4-one Chemical compound O1C2=CC(OC)=CC(O)=C2C(=O)C(OCC)=C1C1=CC=C(O)C(OC)=C1 AMZYHFOAWQBRRS-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 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 claims 1
229930003944 flavone Natural products 0.000 claims 1
235000011949 flavones Nutrition 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
239000007788 liquid Substances 0.000 claims 1
231100000252 nontoxic Toxicity 0.000 claims 1
230000003000 nontoxic effect Effects 0.000 claims 1
125000002924 primary amino group Chemical class [H]N([H])* 0.000 claims 1
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 24
238000002844 melting Methods 0.000 description 23
230000008018 melting Effects 0.000 description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
241000699670 Mus sp. Species 0.000 description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 12
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
238000003756 stirring Methods 0.000 description 10
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000013078 crystal Substances 0.000 description 9
230000000840 anti-viral effect Effects 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 8
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
229910052938 sodium sulfate Inorganic materials 0.000 description 7
235000011152 sodium sulphate Nutrition 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
241000700605 Viruses Species 0.000 description 6
208000015181 infectious disease Diseases 0.000 description 6
KQFUXLQBMQGNRT-UHFFFAOYSA-N pachypodol Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(O)C(OC)=C1 KQFUXLQBMQGNRT-UHFFFAOYSA-N 0.000 description 6
UOJMTSCORVQOHS-UHFFFAOYSA-N pachypodol Natural products COc1cc(ccc1O)C2=C(C)C(=O)c3c(O)cc(C)cc3O2 UOJMTSCORVQOHS-UHFFFAOYSA-N 0.000 description 6
239000000843 powder Substances 0.000 description 6
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230000000694 effects Effects 0.000 description 5
229910000042 hydrogen bromide Inorganic materials 0.000 description 5
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 5
239000000725 suspension Substances 0.000 description 5
241000709687 Coxsackievirus Species 0.000 description 4
BJBUTJQYZDYRMJ-UHFFFAOYSA-N Kaempferol 3,7-dimethyl ether Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(O)C=C1 BJBUTJQYZDYRMJ-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
230000003612 virological effect Effects 0.000 description 4
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000709677 Coxsackievirus B1 Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
238000001816 cooling Methods 0.000 description 3
230000000120 cytopathologic effect Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
YGMHIBLUWGDWKP-UHFFFAOYSA-N (4-methoxybenzoyl) 4-methoxybenzoate Chemical compound C1=CC(OC)=CC=C1C(=O)OC(=O)C1=CC=C(OC)C=C1 YGMHIBLUWGDWKP-UHFFFAOYSA-N 0.000 description 2
RKFVMFXMOKRKHI-UHFFFAOYSA-N 2-(4-aminophenyl)-5,7-dihydroxy-3-methoxychromen-4-one Chemical compound O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=C(N)C=C1 RKFVMFXMOKRKHI-UHFFFAOYSA-N 0.000 description 2
WSQWAMGRHJQANC-UHFFFAOYSA-N 3,4',7-Trimethylkaempferol Natural products C1=CC(OC)=CC=C1C1=C(OC)C(=O)C2=C(O)C=C(OC)C=C2O1 WSQWAMGRHJQANC-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
AUHSZRKTVWRTAA-UHFFFAOYSA-N [4-(5-ethoxycarbonyloxy-3,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] ethyl carbonate Chemical compound C1=C(OC)C(OC(=O)OCC)=CC=C1C1=C(OC)C(=O)C2=C(OC(=O)OCC)C=C(OC)C=C2O1 AUHSZRKTVWRTAA-UHFFFAOYSA-N 0.000 description 2
JMNWVSMCCHOWRN-UHFFFAOYSA-N [4-(5-hydroxy-3,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] 2,2-dimethylpropanoate Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC(=O)C(C)(C)C)C(OC)=C1 JMNWVSMCCHOWRN-UHFFFAOYSA-N 0.000 description 2
OHYCXRVUXQZCQX-UHFFFAOYSA-N [4-[3,7-dimethoxy-5-(2-methylpropanoyloxy)-4-oxochromen-2-yl]-2-methoxyphenyl] 2,2-dimethylpropanoate Chemical compound C=1C(OC)=CC(OC(=O)C(C)C)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC(=O)C(C)(C)C)C(OC)=C1 OHYCXRVUXQZCQX-UHFFFAOYSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
244000309466 calf Species 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
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231100000518 lethal Toxicity 0.000 description 2
230000001665 lethal effect Effects 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
229940056360 penicillin g Drugs 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
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LOQXTRPEVWKWKG-UHFFFAOYSA-N (2-methoxy-4-phenylmethoxybenzoyl) 2-methoxy-4-phenylmethoxybenzoate Chemical compound C=1C=C(C(=O)OC(=O)C=2C(=CC(OCC=3C=CC=CC=3)=CC=2)OC)C(OC)=CC=1OCC1=CC=CC=C1 LOQXTRPEVWKWKG-UHFFFAOYSA-N 0.000 description 1
JIMLDJNLXLMGLX-JTQLQIEISA-N (2s)-5-amino-5-oxo-2-(phenylmethoxycarbonylamino)pentanoic acid Chemical compound NC(=O)CC[C@@H](C(O)=O)NC(=O)OCC1=CC=CC=C1 JIMLDJNLXLMGLX-JTQLQIEISA-N 0.000 description 1
ZSKPRSCIVQDZDS-UHFFFAOYSA-N (3-methoxy-4-phenylmethoxybenzoyl) 3-methoxy-4-phenylmethoxybenzoate Chemical compound COC1=CC(C(=O)OC(=O)C=2C=C(OC)C(OCC=3C=CC=CC=3)=CC=2)=CC=C1OCC1=CC=CC=C1 ZSKPRSCIVQDZDS-UHFFFAOYSA-N 0.000 description 1
MCWOIFCXBMZSBD-UHFFFAOYSA-N (4-methoxy-3-phenylmethoxybenzoyl) 4-methoxy-3-phenylmethoxybenzoate Chemical compound COC1=CC=C(C(=O)OC(=O)C=2C=C(OCC=3C=CC=CC=3)C(OC)=CC=2)C=C1OCC1=CC=CC=C1 MCWOIFCXBMZSBD-UHFFFAOYSA-N 0.000 description 1
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SGQLQPOIEQFQTN-ZOWNYOTGSA-N (4s)-4-amino-5-[4-(5-hydroxy-3,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenoxy]-5-oxopentanoic acid;hydrobromide Chemical compound Br.C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC(=O)[C@@H](N)CCC(O)=O)C(OC)=C1 SGQLQPOIEQFQTN-ZOWNYOTGSA-N 0.000 description 1
ICLYJLBTOGPLMC-KVVVOXFISA-N (z)-octadec-9-enoate;tris(2-hydroxyethyl)azanium Chemical compound OCCN(CCO)CCO.CCCCCCCC\C=C/CCCCCCCC(O)=O ICLYJLBTOGPLMC-KVVVOXFISA-N 0.000 description 1
MKLYGUJAWHZWFN-UHFFFAOYSA-N 1-(2,6-dihydroxy-4-methoxyphenyl)-2-propan-2-yloxyethanone Chemical compound COC1=CC(O)=C(C(=O)COC(C)C)C(O)=C1 MKLYGUJAWHZWFN-UHFFFAOYSA-N 0.000 description 1
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CYAYKKUWALRRPA-RGDJUOJXSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-bromooxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@H](Br)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O CYAYKKUWALRRPA-RGDJUOJXSA-N 0.000 description 1
CHHHDBIYMPJYLB-UHFFFAOYSA-N [4-(3,7-dimethoxy-4-oxo-5-propanoyloxychromen-2-yl)-2-methoxyphenyl] propanoate Chemical compound C1=C(OC)C(OC(=O)CC)=CC=C1C1=C(OC)C(=O)C2=C(OC(=O)CC)C=C(OC)C=C2O1 CHHHDBIYMPJYLB-UHFFFAOYSA-N 0.000 description 1
KKLNIZIIWNRCNN-JTQLQIEISA-N [4-(5-hydroxy-3,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] (2s)-2-aminopropanoate Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC(=O)[C@H](C)N)C(OC)=C1 KKLNIZIIWNRCNN-JTQLQIEISA-N 0.000 description 1
JBWVEEJCIGBJQO-UHFFFAOYSA-N [4-(5-hydroxy-3,7-dimethoxy-4-oxochromen-2-yl)-2-methoxyphenyl] acetate Chemical compound C=1C(OC)=CC(O)=C(C(C=2OC)=O)C=1OC=2C1=CC=C(OC(C)=O)C(OC)=C1 JBWVEEJCIGBJQO-UHFFFAOYSA-N 0.000 description 1
IUJKWETXANBZPF-UHFFFAOYSA-N [4-[3,7-dimethoxy-4-oxo-5-(pyridine-3-carbonyloxy)chromen-2-yl]-2-methoxyphenyl] pyridine-3-carboxylate Chemical compound O1C(C=2C=C(OC)C(OC(=O)C=3C=NC=CC=3)=CC=2)=C(OC)C(=O)C=2C1=CC(OC)=CC=2OC(=O)C1=CC=CN=C1 IUJKWETXANBZPF-UHFFFAOYSA-N 0.000 description 1
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
238000001720 action spectrum Methods 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
230000007059 acute toxicity Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000000266 alpha-aminoacyl group Chemical group 0.000 description 1
DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
229960003805 amantadine Drugs 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
230000001754 anti-pyretic effect Effects 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
239000002221 antipyretic Substances 0.000 description 1
229940125716 antipyretic agent Drugs 0.000 description 1
239000003443 antiviral agent Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000001569 carbon dioxide Substances 0.000 description 1
229910002092 carbon dioxide Inorganic materials 0.000 description 1
238000004113 cell culture Methods 0.000 description 1
230000010261 cell growth Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000001332 colony forming effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
230000013595 glycosylation Effects 0.000 description 1
238000006206 glycosylation reaction Methods 0.000 description 1
239000008187 granular material Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000001727 in vivo Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
229940079322 interferon Drugs 0.000 description 1
239000008101 lactose Substances 0.000 description 1
210000005265 lung cell Anatomy 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
TYRGLVWXHJRKMT-QMMMGPOBSA-N n-benzyloxycarbonyl-l-serine-betalactone Chemical compound OC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1 TYRGLVWXHJRKMT-QMMMGPOBSA-N 0.000 description 1
231100001083 no cytotoxicity Toxicity 0.000 description 1
239000002674 ointment Substances 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229940124641 pain reliever Drugs 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
235000019271 petrolatum Nutrition 0.000 description 1
239000002953 phosphate buffered saline Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
ZLASJWLZBYSLDG-UHFFFAOYSA-M potassium;4-methoxybenzoate Chemical compound [K+].COC1=CC=C(C([O-])=O)C=C1 ZLASJWLZBYSLDG-UHFFFAOYSA-M 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
IIXVGSLUOUGCNU-UHFFFAOYSA-M sodium;2-methoxy-4-phenylmethoxybenzoate Chemical compound [Na+].C1=C(C([O-])=O)C(OC)=CC(OCC=2C=CC=CC=2)=C1 IIXVGSLUOUGCNU-UHFFFAOYSA-M 0.000 description 1
OGRZCYWSKAPOSR-UHFFFAOYSA-M sodium;3-methoxy-4-phenylmethoxybenzoate Chemical compound [Na+].COC1=CC(C([O-])=O)=CC=C1OCC1=CC=CC=C1 OGRZCYWSKAPOSR-UHFFFAOYSA-M 0.000 description 1
QCTHGBUDZUJILN-UHFFFAOYSA-M sodium;4-acetamidobenzoate Chemical compound [Na+].CC(=O)NC1=CC=C(C([O-])=O)C=C1 QCTHGBUDZUJILN-UHFFFAOYSA-M 0.000 description 1
AETSDHMVQHOYPB-UHFFFAOYSA-M sodium;4-methoxybenzoate Chemical compound [Na+].COC1=CC=C(C([O-])=O)C=C1 AETSDHMVQHOYPB-UHFFFAOYSA-M 0.000 description 1
WOUZNSRCJPRTHA-UHFFFAOYSA-M sodium;4-phenylmethoxybenzoate Chemical compound [Na+].C1=CC(C(=O)[O-])=CC=C1OCC1=CC=CC=C1 WOUZNSRCJPRTHA-UHFFFAOYSA-M 0.000 description 1
235000014347 soups Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
229960005322 streptomycin Drugs 0.000 description 1
229960002385 streptomycin sulfate Drugs 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000003826 tablet Substances 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
239000011975 tartaric acid Substances 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 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
- C07D311/28—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 2 only
- C07D311/30—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 2 only not hydrogenated in the hetero ring, e.g. flavones
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Virology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pyrane Compounds (AREA)
Saccharide Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

NO801024A 1979-04-10 1980-04-09 Nye flavonderivater, fremstilling og preparater av disse NO801024L (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB7912610		1979-04-10
GB8006259		1980-02-25

Publications (1)

Publication Number	Publication Date
NO801024L true NO801024L (no)	1980-10-13

Family

ID=26271208

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO801024A NO801024L (no)	1979-04-10	1980-04-09	Nye flavonderivater, fremstilling og preparater av disse

Country Status (16)

Country	Link
US (1)	US4352792A (fr)
EP (1)	EP0019081B1 (fr)
JP (1)	JPH01117879A (fr)
AU (1)	AU538214B2 (fr)
CU (1)	CU35257A (fr)
DE (1)	DE3069488D1 (fr)
DK (1)	DK152980A (fr)
FI (1)	FI801050A7 (fr)
IE (1)	IE49670B1 (fr)
IL (1)	IL59770A (fr)
MC (1)	MC1316A1 (fr)
NO (1)	NO801024L (fr)
NZ (1)	NZ193316A (fr)
PH (1)	PH17987A (fr)
PT (1)	PT71078B (fr)
ZW (1)	ZW8180A1 (fr)

Families Citing this family (21)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2543140B1 (fr) *	1983-03-24	1985-06-21	Cortial	Nouveaux acides flavone-carboxyliques-4', leur methode de preparation et leur application en therapeutique
FR2543550B1 (fr) *	1983-04-01	1985-08-09	Cortial	Nouveaux derives de la tetrahydroxy-3', 4',5,7 flavone, leur methode de preparation et leur emploi therapeutique
DE3505611A1 (de) *	1984-11-26	1986-05-28	Merck Patent Gmbh, 6100 Darmstadt	Halogen-hydroxy-flavone
FR2593066B1 (fr) *	1986-01-17	1989-06-30	Pasteur Institut	Compositions therapeutiques a base de derives de 3-alkoxyflavones et nouveaux derives de 3-alkoxyflavones.
USH1427H (en) *	1988-04-06	1995-04-04	Briet; Phillipe	Substituted flavonoid compounds, their salts, their manufacture and their use in combination with interleukin-2
US5185366A (en) *	1990-07-31	1993-02-09	Ohio State University Research Foundation	Method for treatment and prevention of diseases caused by enveloped viruses, including herpes simplex virus types 1 and 2 diseases, using 3,4-dihydroxy-2H-benzopyran-2H-one
US5449794A (en) *	1991-02-15	1995-09-12	Jasmine Fockerman	Benzopyran phenol derivatives for use as antibacterial agents
US5861430A (en) *	1991-12-17	1999-01-19	Jasmine Fockerman	Benzopyran phenol derivates for use as antibacterial, antiviral or immunostimulating agents
US5591771A (en) *	1991-12-17	1997-01-07	Michel Fockerman	Use of propolis components as an adjuvant
US5401503A (en) *	1992-03-12	1995-03-28	Sanwa Shoyaku Kabushiki Kaisha	Hair growth stimulant
GB9613455D0 (en)	1996-06-27	1996-08-28	Aston Molecules Ltd	Analogues or derivatives of quercetin
US6083921A (en) *	1998-01-12	2000-07-04	Xu; Kai Jian	Pharmaceutical compositions and method of using same
FR2778663B1 (fr) *	1998-05-15	2001-05-18	Coletica	Nouveaux esters de flavonoides,leur utilisation en cosmetique, dermopharmacie, en pharmacie et en agro-alimentaire
IT1304304B1 (it)	1998-10-30	2001-03-15	Euro Pharma S R L	Prodotti per l'igiene personale a base di estratti di lapachocontenenti quercetina ed eventuali altri chinoni presenti nel lapacho
US6555523B1 (en)	1999-07-08	2003-04-29	Patrick T. Prendergast	Use of cirsiliol and derivatives to treat infections
AU7561300A (en) *	1999-09-23	2001-04-24	Universiteit Van Maastricht	Novel flavonoids
DE602004020463D1 (de) *	2003-05-15	2009-05-20	Chengdu Dikang Pharmaceutical	Isoflavonderivative von tectoridin, deren herstellung und antivirale medikamente, die diese als wirksame bestandteile enthalten
JP2007516937A (ja) *	2003-06-20	2007-06-28	コグニス・フランス・ソシエテ・パール・アクシオン・サンプリフィエ	フラボノイドとω−置換Ｃ６〜Ｃ２２脂肪酸とのエステル
CN1990479A (zh) *	2005-12-29	2007-07-04	中国科学院上海药物研究所	3－烷氧取代－2,5,7－三取代苯并吡喃－4－酮类化合物及其制备方法和包含该类化合物的药物组合物
AU2006233256B2 (en) *	2006-10-30	2012-01-19	Armaron Bio Pty Ltd	Improved flavonols
EP3594209A1 (fr) *	2018-07-13	2020-01-15	Centre National De La Recherche Scientifique (Cnrs)	Dérivés de flavonoïdes lipophénoliques utiles pour réduire les contraintes carbonyles et oxydatives (cos)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3336198A (en) *	1964-02-14	1967-08-15	Ciba Geigy Corp	Aminomethyl derivatives of rutin and process for the manufacture thereof
FR1578715A (fr) *	1967-07-26	1969-08-22
FR95487E (fr)	1967-07-26	1971-01-15	Rech S Ind Sori Soc D	Nouveaux dérives flavoniques.
FR2088127B1 (fr) *	1970-05-21	1973-04-06	Biosedra Lab
US4105781A (en) *	1970-12-30	1978-08-08	Fujisawa Pharmaceutical Co., Ltd.	Chromone compounds and preparation thereof
GB1461777A (en) *	1973-06-08	1977-01-19	Fisons Ltd	2-phenyl-4-oxo-4h-1-benzopyran derivatives
HU166380B (fr) *	1973-07-09	1975-03-28
JPS5035393A (fr) *	1973-08-01	1975-04-04
US4150038A (en) *	1977-05-16	1979-04-17	Dynapol	Conversion of hesperidin into hesperetin
DE2740950A1 (de) *	1977-09-10	1979-03-22	Merck Patent Gmbh	Verfahren zur herstellung von flavonen
HU187755B (en) *	1978-03-15	1986-02-28	Wellcome Found	Process for producing flavane derivatives of antivirus activity and pharmaceutical compositions containing them as active agents

1980
- 1980-03-31 NZ NZ193316A patent/NZ193316A/en unknown
- 1980-04-02 FI FI801050A patent/FI801050A7/fi not_active Application Discontinuation
- 1980-04-03 MC MC801442A patent/MC1316A1/fr unknown
- 1980-04-03 ZW ZW81/80A patent/ZW8180A1/xx unknown
- 1980-04-03 AU AU57157/80A patent/AU538214B2/en not_active Ceased
- 1980-04-04 IL IL59770A patent/IL59770A/xx unknown
- 1980-04-07 US US06/137,637 patent/US4352792A/en not_active Expired - Lifetime
- 1980-04-09 PH PH23875A patent/PH17987A/en unknown
- 1980-04-09 EP EP80101894A patent/EP0019081B1/fr not_active Expired
- 1980-04-09 NO NO801024A patent/NO801024L/no unknown
- 1980-04-09 PT PT71078A patent/PT71078B/pt unknown
- 1980-04-09 DE DE8080101894T patent/DE3069488D1/de not_active Expired
- 1980-04-09 IE IE711/80A patent/IE49670B1/en unknown
- 1980-04-09 DK DK152980A patent/DK152980A/da not_active IP Right Cessation
- 1980-04-10 CU CU8035257A patent/CU35257A/es unknown
1988
- 1988-09-22 JP JP63236640A patent/JPH01117879A/ja active Pending

Also Published As

Publication number	Publication date
EP0019081B1 (fr)	1984-10-24
PT71078A (en)	1980-05-01
US4352792A (en)	1982-10-05
ZW8180A1 (en)	1980-11-05
PT71078B (en)	1981-08-03
DK152980A (da)	1980-10-15
EP0019081A1 (fr)	1980-11-26
IE800711L (en)	1980-10-10
MC1316A1 (fr)	1981-03-10
CU35257A (en)	1982-03-28
PH17987A (en)	1985-02-28
AU538214B2 (en)	1984-08-02
IL59770A (en)	1984-07-31
FI801050A7 (fi)	1981-01-01
IL59770A0 (en)	1980-06-30
AU5715780A (en)	1980-10-16
NZ193316A (en)	1984-07-31
DE3069488D1 (en)	1984-11-29
IE49670B1 (en)	1985-11-13
JPH01117879A (ja)	1989-05-10

Publication	Publication Date	Title
NO801024L (no)	1980-10-13	Nye flavonderivater, fremstilling og preparater av disse
US6627611B2 (en)	2003-09-30	C-glycosides and preparation of thereof as antidiabetic agents
CS172991A3 (en)	1992-08-12	Derivatives of hydroxy- and alkoxypyridines
Linardi et al.	1975	Lapachol derivative active against mouse lymphocytic leukemia P-388
JPH03188042A (ja)	1991-08-16	キノン誘導体
US4605674A (en)	1986-08-12	Substituted acetophenones and compositions containing them
Mateeva et al.	2002	Synthesis of novel flavonoid derivatives as potential HIV‐Integrase inhibitors
CN109223806A (zh)	2019-01-18	达玛烷型三萜衍生物的用途
JPH01131156A (ja)	1989-05-24	ピペリジン誘導体
US4327088A (en)	1982-04-27	Phosphonooxy- or glycosyloxy-substituted acrylophenones, compositions and uses thereof
JPH0118049B2 (fr)	1989-04-03
CN117466837B (zh)	2025-11-28	一种粉背蕨酸衍生物、制备方法及其应用
CN115160399B (zh)	2023-10-27	一种皂皮酸类化合物及其制备方法和医用用途
US5292751A (en)	1994-03-08	5,7-dihydroxy-2-methyl-8-(4-(3-hydroxy-1-(1-propyl))piperidinyl)-4H-1-benzopyran-4-one, its preparation and its use
Geissman	1951	Chromones. IV. The Conversion of Khellol into Visnagin. Derivatives of Khellol and Visnagin
US4013770A (en)	1977-03-22	Antiviral 5-(substituted benzal) hydantoins
EP1322632A1 (fr)	2003-07-02	Carbamoyloxy flavones n-disubstituees
CN108078993B (zh)	2020-02-21	6-硝基喹唑啉类化合物在制备治疗肺癌药物中的应用
US4371546A (en)	1983-02-01	Benzophenone derivatives
KR20250059517A (ko)	2025-05-02	케토아미드 유도체의 무정형 및 그 제조 방법
US4725620A (en)	1988-02-16	2H-pyran-2,6-(3H)-dione derivatives with anti-allergic activity
JPH02121982A (ja)	1990-05-09	エライオフイリン誘導体
JPS61257981A (ja)	1986-11-15	ジベンズ〔ｂ，ｅ〕オキセピン誘導体および抗アレルギ−剤
CA1074803A (fr)	1980-04-01	1-thiazolinyl-5(6)-substituant-ben-zimidazoles
HRP20020352A2 (en)	2004-02-29	Aromatic di-keto derivatives, processes for their production and their use as pharmaceutical