DE2746166A1 - 6-carboxy-flavon-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel - Google Patents
6-carboxy-flavon-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittelInfo
- Publication number
- DE2746166A1 DE2746166A1 DE19772746166 DE2746166A DE2746166A1 DE 2746166 A1 DE2746166 A1 DE 2746166A1 DE 19772746166 DE19772746166 DE 19772746166 DE 2746166 A DE2746166 A DE 2746166A DE 2746166 A1 DE2746166 A1 DE 2746166A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxy
- flavone
- salt
- isopropoxy
- methyl
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 12
- ZWQMQNRKCRVLHW-UHFFFAOYSA-N 4-oxo-2-phenylchromene-6-carboxylic acid Chemical class C=1C(=O)C2=CC(C(=O)O)=CC=C2OC=1C1=CC=CC=C1 ZWQMQNRKCRVLHW-UHFFFAOYSA-N 0.000 title claims description 7
- 239000008177 pharmaceutical agent Substances 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 60
- 150000003839 salts Chemical class 0.000 claims description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- YLTVMVPQDVIYER-UHFFFAOYSA-N 2-(5-methyl-2-propan-2-yloxyphenyl)-4-oxochromene-6-carboxylic acid Chemical compound CC(C)OC1=CC=C(C)C=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 YLTVMVPQDVIYER-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- CCCXWWHGGRBMBF-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)-4-oxochromene-6-carboxylic acid Chemical compound COC1=CC=C(C)C=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 CCCXWWHGGRBMBF-UHFFFAOYSA-N 0.000 claims description 4
- LLEQVOQPQJJXRU-UHFFFAOYSA-N 2-(4-methyl-2-propan-2-yloxyphenyl)-4-oxochromene-6-carboxylic acid Chemical compound CC(C)OC1=CC(C)=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 LLEQVOQPQJJXRU-UHFFFAOYSA-N 0.000 claims description 4
- -1 2-ethoxyethyl Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- FPKZSBVVPHQFRN-UHFFFAOYSA-N 2-(2-methoxy-3-methylphenyl)-4-oxochromene-6-carboxylic acid Chemical compound COC1=C(C)C=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 FPKZSBVVPHQFRN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- UFLZLPNPZUTXTQ-UHFFFAOYSA-N 2-(5-ethyl-2-propan-2-yloxyphenyl)-4-oxochromene-6-carboxylic acid Chemical compound CCC1=CC=C(OC(C)C)C(C=2OC3=CC=C(C=C3C(=O)C=2)C(O)=O)=C1 UFLZLPNPZUTXTQ-UHFFFAOYSA-N 0.000 claims 1
- OLOSDTXMJDVCTD-UHFFFAOYSA-N 4-oxo-2-(2-propan-2-yloxy-3-propylphenyl)chromene-6-carboxylic acid Chemical compound CCCC1=CC=CC(C=2OC3=CC=C(C=C3C(=O)C=2)C(O)=O)=C1OC(C)C OLOSDTXMJDVCTD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
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- 238000010992 reflux Methods 0.000 description 8
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
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- 238000006243 chemical reaction Methods 0.000 description 6
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- 239000002253 acid Substances 0.000 description 5
- 239000012442 inert solvent Substances 0.000 description 5
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
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- 239000002585 base Substances 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000008101 lactose Substances 0.000 description 4
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 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 3
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 2
- HLBUIVARRPNNSN-UHFFFAOYSA-N 2-(3-methyl-2-propan-2-yloxyphenyl)-4-oxochromene-6-carboxylic acid Chemical compound CC(C)OC1=C(C)C=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 HLBUIVARRPNNSN-UHFFFAOYSA-N 0.000 description 2
- WJGAPNSNJXZBPQ-UHFFFAOYSA-N 2-(3-methylphenyl)chromen-4-one Chemical compound CC1=CC=CC(C=2OC3=CC=CC=C3C(=O)C=2)=C1 WJGAPNSNJXZBPQ-UHFFFAOYSA-N 0.000 description 2
- GDBUZIKSJGRBJP-UHFFFAOYSA-N 4-acetoxy benzoic acid Chemical compound CC(=O)OC1=CC=C(C(O)=O)C=C1 GDBUZIKSJGRBJP-UHFFFAOYSA-N 0.000 description 2
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
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- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 102000036639 antigens Human genes 0.000 description 1
- 108091007433 antigens Proteins 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 235000001465 calcium Nutrition 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 235000013539 calcium stearate Nutrition 0.000 description 1
- 239000008116 calcium stearate Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000812 cholinergic antagonist Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- VOYAPKKWTPXTMU-UHFFFAOYSA-N ethyl 2-(4-methyl-2-propan-2-yloxyphenyl)-4-oxochromene-6-carboxylate Chemical compound C=1C(=O)C2=CC(C(=O)OCC)=CC=C2OC=1C1=CC=C(C)C=C1OC(C)C VOYAPKKWTPXTMU-UHFFFAOYSA-N 0.000 description 1
- XZDVCBGAJVUGNC-UHFFFAOYSA-N ethyl 2-(5-methyl-2-propan-2-yloxyphenyl)-4-oxochromene-6-carboxylate Chemical compound C=1C(=O)C2=CC(C(=O)OCC)=CC=C2OC=1C1=CC(C)=CC=C1OC(C)C XZDVCBGAJVUGNC-UHFFFAOYSA-N 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- FVIZARNDLVOMSU-UHFFFAOYSA-N ginsenoside K Natural products C1CC(C2(CCC3C(C)(C)C(O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC1OC(CO)C(O)C(O)C1O FVIZARNDLVOMSU-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- LLWHVIBMCLUXGY-UHFFFAOYSA-N methyl 2-(2-methoxy-5-methylphenyl)-4-oxochromene-6-carboxylate Chemical compound C=1C(=O)C2=CC(C(=O)OC)=CC=C2OC=1C1=CC(C)=CC=C1OC LLWHVIBMCLUXGY-UHFFFAOYSA-N 0.000 description 1
- HRIFAUHCKFFZKB-UHFFFAOYSA-N methyl 2-methoxy-5-methylbenzoate Chemical compound COC(=O)C1=CC(C)=CC=C1OC HRIFAUHCKFFZKB-UHFFFAOYSA-N 0.000 description 1
- LYZNEHUOUJKWHL-UHFFFAOYSA-N methyl 4-hydroxy-3-[3-(5-methyl-2-propan-2-yloxyphenyl)-3-oxopropanoyl]benzoate Chemical compound COC(=O)C1=CC=C(O)C(C(=O)CC(=O)C=2C(=CC=C(C)C=2)OC(C)C)=C1 LYZNEHUOUJKWHL-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000005406 washing Methods 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pulmonology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT28527/76A IT1069041B (it) | 1976-10-21 | 1976-10-21 | Acidi falvon-6-carbossilici sostituiti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2746166A1 true DE2746166A1 (de) | 1978-04-27 |
Family
ID=11223738
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772746166 Withdrawn DE2746166A1 (de) | 1976-10-21 | 1977-10-14 | 6-carboxy-flavon-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
Country Status (13)
| Country | Link |
|---|---|
| AT (1) | AT356104B (cs) |
| AU (1) | AU508555B2 (cs) |
| BE (1) | BE859940R (cs) |
| CA (1) | CA1117957A (cs) |
| DE (1) | DE2746166A1 (cs) |
| FR (1) | FR2368484A2 (cs) |
| GB (1) | GB1542986A (cs) |
| IT (1) | IT1069041B (cs) |
| NL (1) | NL7711215A (cs) |
| NZ (1) | NZ185454A (cs) |
| SU (1) | SU795474A3 (cs) |
| YU (1) | YU242577A (cs) |
| ZA (1) | ZA776161B (cs) |
-
1976
- 1976-10-21 IT IT28527/76A patent/IT1069041B/it active
-
1977
- 1977-10-10 YU YU02425/77A patent/YU242577A/xx unknown
- 1977-10-12 GB GB42541/77A patent/GB1542986A/en not_active Expired
- 1977-10-12 NL NL7711215A patent/NL7711215A/xx not_active Application Discontinuation
- 1977-10-12 AT AT729877A patent/AT356104B/de not_active IP Right Cessation
- 1977-10-13 AU AU29675/77A patent/AU508555B2/en not_active Expired
- 1977-10-14 ZA ZA00776161A patent/ZA776161B/xx unknown
- 1977-10-14 DE DE19772746166 patent/DE2746166A1/de not_active Withdrawn
- 1977-10-18 NZ NZ185454A patent/NZ185454A/xx unknown
- 1977-10-20 CA CA000289123A patent/CA1117957A/en not_active Expired
- 1977-10-20 BE BE181918A patent/BE859940R/xx active
- 1977-10-20 SU SU772531357A patent/SU795474A3/ru active
- 1977-10-21 FR FR7731797A patent/FR2368484A2/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| YU242577A (en) | 1982-08-31 |
| BE859940R (fr) | 1978-02-15 |
| ATA729877A (de) | 1979-09-15 |
| AU2967577A (en) | 1979-04-26 |
| FR2368484A2 (fr) | 1978-05-19 |
| ZA776161B (en) | 1978-06-28 |
| NZ185454A (en) | 1980-08-26 |
| FR2368484B2 (cs) | 1980-06-20 |
| SU795474A3 (ru) | 1981-01-07 |
| AT356104B (de) | 1980-04-10 |
| AU508555B2 (en) | 1980-03-27 |
| NL7711215A (nl) | 1978-04-25 |
| GB1542986A (en) | 1979-03-28 |
| CA1117957A (en) | 1982-02-09 |
| IT1069041B (it) | 1985-03-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: FARMITALIA CARLO ERBA S.P.A., 20159 MILANO, IT |
|
| 8110 | Request for examination paragraph 44 | ||
| 8130 | Withdrawal |