DE2461670A1 - 5,6-benzo-gamma-pyronderivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen - Google Patents
5,6-benzo-gamma-pyronderivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungenInfo
- Publication number
- DE2461670A1 DE2461670A1 DE19742461670 DE2461670A DE2461670A1 DE 2461670 A1 DE2461670 A1 DE 2461670A1 DE 19742461670 DE19742461670 DE 19742461670 DE 2461670 A DE2461670 A DE 2461670A DE 2461670 A1 DE2461670 A1 DE 2461670A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxy
- chromone
- flavone
- pyridyl
- general 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 24
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 111
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical compound C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 108
- -1 cyano, carboxy Chemical group 0.000 claims description 80
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 51
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
- 229920002554 vinyl polymer Polymers 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 238000002360 preparation method Methods 0.000 claims description 17
- YLQMFQKRHQCFBI-UHFFFAOYSA-N 4-oxo-2-(2-propan-2-yloxyphenyl)chromene-6-carboxylic acid Chemical compound CC(C)OC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 YLQMFQKRHQCFBI-UHFFFAOYSA-N 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 235000011949 flavones Nutrition 0.000 claims description 13
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 claims description 13
- 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 description 12
- 229930003944 flavone Natural products 0.000 claims description 12
- 150000002212 flavone derivatives Chemical class 0.000 claims description 11
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 11
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000001331 3-methylbutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 150000001204 N-oxides Chemical class 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- CPEONABTMRSIKA-UHFFFAOYSA-N 1,4$l^{2}-oxazinane Chemical compound C1COCC[N]1 CPEONABTMRSIKA-UHFFFAOYSA-N 0.000 claims description 3
- QFWHGFWLTJVPHG-UHFFFAOYSA-N 2-[2-(dimethylamino)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound CN(C)C1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 QFWHGFWLTJVPHG-UHFFFAOYSA-N 0.000 claims description 3
- CACYIXYLZLKFJO-UHFFFAOYSA-N 4-oxo-2-(2-propan-2-yloxyphenyl)chromene-7-carboxylic acid Chemical compound CC(C)OC1=CC=CC=C1C1=CC(=O)C2=CC=C(C(O)=O)C=C2O1 CACYIXYLZLKFJO-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical group C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- MALPGDSEBULKPW-UHFFFAOYSA-N 2-(2-aminophenyl)-4-oxochromene-6-carboxylic acid Chemical compound NC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 MALPGDSEBULKPW-UHFFFAOYSA-N 0.000 claims description 2
- FNOGVKQMXXVLIH-UHFFFAOYSA-N 2-(2-butoxyphenyl)-4-oxochromene-6-carboxylic acid Chemical compound CCCCOC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 FNOGVKQMXXVLIH-UHFFFAOYSA-N 0.000 claims description 2
- DSLVTOWJYVIYKG-UHFFFAOYSA-N 2-[2-(2-hydroxybutoxy)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound CCC(O)COC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 DSLVTOWJYVIYKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 2
- RWBCSOJJSOOSPA-UHFFFAOYSA-N 4-oxo-2-(2-propoxyphenyl)chromene-6-carboxylic acid Chemical compound CCCOC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 RWBCSOJJSOOSPA-UHFFFAOYSA-N 0.000 claims description 2
- OHCNSTOLJWDQMJ-UHFFFAOYSA-N 4-oxo-2-phenylchromene-7-carboxylic acid Chemical compound C=1C(C(=O)O)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1 OHCNSTOLJWDQMJ-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- JVYMKTAPCLSXLC-UHFFFAOYSA-N COClO Chemical compound COClO JVYMKTAPCLSXLC-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 229910052760 oxygen Chemical group 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 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 description 2
- ILJVECQFLJHCCG-UHFFFAOYSA-N 2-(4-oxo-2-phenylchromen-3-yl)acetic acid Chemical compound O1C2=CC=CC=C2C(=O)C(CC(=O)O)=C1C1=CC=CC=C1 ILJVECQFLJHCCG-UHFFFAOYSA-N 0.000 claims 1
- SVLCHSFCKRQQBJ-UHFFFAOYSA-N 2-[2-(2,3-dihydroxypropoxy)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound OCC(O)COC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 SVLCHSFCKRQQBJ-UHFFFAOYSA-N 0.000 claims 1
- GKWXNIZHVQLKQY-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound CCOCCOC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 GKWXNIZHVQLKQY-UHFFFAOYSA-N 0.000 claims 1
- SLONTNWWEGEUDU-UHFFFAOYSA-N 2-[2-(2-hydroxy-2-methylbutoxy)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound CCC(C)(O)COC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 SLONTNWWEGEUDU-UHFFFAOYSA-N 0.000 claims 1
- ABOMOLAFCBXXGB-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound CC(O)COC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 ABOMOLAFCBXXGB-UHFFFAOYSA-N 0.000 claims 1
- QSUAFVVBDVEYER-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)phenyl]-4-oxochromene-7-carboxylic acid Chemical compound CC(O)COC1=CC=CC=C1C1=CC(=O)C2=CC=C(C(O)=O)C=C2O1 QSUAFVVBDVEYER-UHFFFAOYSA-N 0.000 claims 1
- VTYLDVVZTWOICJ-UHFFFAOYSA-N 2-[2-(2-methylpropoxy)phenyl]-4-oxochromene-7-carboxylic acid Chemical compound CC(C)COC1=CC=CC=C1C1=CC(=O)C2=CC=C(C(O)=O)C=C2O1 VTYLDVVZTWOICJ-UHFFFAOYSA-N 0.000 claims 1
- BHMHAZWBOPIELQ-UHFFFAOYSA-N 2-[2-(3-hydroxypropoxy)phenyl]-4-oxochromene-6-carboxylic acid Chemical compound OCCCOC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 BHMHAZWBOPIELQ-UHFFFAOYSA-N 0.000 claims 1
- IJRWYPMSOQRREY-UHFFFAOYSA-N 4-oxo-2-[2-(propan-2-ylamino)phenyl]chromene-6-carboxylic acid Chemical compound CC(C)NC1=CC=CC=C1C1=CC(=O)C2=CC(C(O)=O)=CC=C2O1 IJRWYPMSOQRREY-UHFFFAOYSA-N 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 238000007911 parenteral administration Methods 0.000 claims 1
- 238000011200 topical administration Methods 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 101
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000010992 reflux Methods 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 22
- 238000001816 cooling Methods 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 20
- 239000002244 precipitate Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 17
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 238000002425 crystallisation Methods 0.000 description 14
- 230000008025 crystallization Effects 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 229910000027 potassium carbonate Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000010790 dilution Methods 0.000 description 10
- 239000012895 dilution Substances 0.000 description 10
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 238000007865 diluting Methods 0.000 description 8
- 229910052740 iodine Inorganic materials 0.000 description 8
- 150000003254 radicals Chemical class 0.000 description 8
- 239000012312 sodium hydride Substances 0.000 description 8
- 229910000104 sodium hydride Inorganic materials 0.000 description 8
- 159000000000 sodium salts Chemical class 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- 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 5
- ZWQMQNRKCRVLHW-UHFFFAOYSA-N 4-oxo-2-phenylchromene-6-carboxylic acid Chemical compound C=1C(=O)C2=CC(C(=O)O)=CC=C2OC=1C1=CC=CC=C1 ZWQMQNRKCRVLHW-UHFFFAOYSA-N 0.000 description 5
- 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 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 150000001350 alkyl halides Chemical class 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 235000019253 formic acid Nutrition 0.000 description 5
- 239000008101 lactose 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
- 230000020477 pH reduction Effects 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000003380 propellant Substances 0.000 description 5
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 5
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 239000008120 corn starch Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 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
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 3
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000000787 lecithin Substances 0.000 description 3
- 235000010445 lecithin Nutrition 0.000 description 3
- 229940067606 lecithin Drugs 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- NTSMIVYANJBXBU-UHFFFAOYSA-N methyl 2-(2-hydroxyphenyl)-4-oxochromene-6-carboxylate Chemical compound C=1C(=O)C2=CC(C(=O)OC)=CC=C2OC=1C1=CC=CC=C1O NTSMIVYANJBXBU-UHFFFAOYSA-N 0.000 description 3
- FPYAQSSSRQZXMS-UHFFFAOYSA-N methyl 3-acetyl-4-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(O)C(C(C)=O)=C1 FPYAQSSSRQZXMS-UHFFFAOYSA-N 0.000 description 3
- 150000003222 pyridines Chemical class 0.000 description 3
- 125000004076 pyridyl group Chemical group 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
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- 208000030603 inherited susceptibility to asthma Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000007517 lewis acids Chemical class 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
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- PFTQDRBATQRZEV-UHFFFAOYSA-N methyl 2-(2-hydroxyphenyl)-4-oxochromene-7-carboxylate Chemical compound C=1C(C(=O)OC)=CC=C(C(C=2)=O)C=1OC=2C1=CC=CC=C1O PFTQDRBATQRZEV-UHFFFAOYSA-N 0.000 description 1
- VPLIRLKVRXJBHG-UHFFFAOYSA-N methyl 2-(2-nitrophenyl)-4-oxo-2,3-dihydrochromene-6-carboxylate Chemical compound C1C(=O)C2=CC(C(=O)OC)=CC=C2OC1C1=CC=CC=C1[N+]([O-])=O VPLIRLKVRXJBHG-UHFFFAOYSA-N 0.000 description 1
- KGZYMRFJKMHAKX-UHFFFAOYSA-N methyl 2-[2-(2-benzoyloxypropoxy)phenyl]-4-oxochromene-6-carboxylate Chemical compound C=1C(=O)C2=CC(C(=O)OC)=CC=C2OC=1C1=CC=CC=C1OCC(C)OC(=O)C1=CC=CC=C1 KGZYMRFJKMHAKX-UHFFFAOYSA-N 0.000 description 1
- MTGWPWPIDLQCPQ-UHFFFAOYSA-N methyl 2-[2-(2-ethoxyethoxy)phenyl]-4-oxochromene-6-carboxylate Chemical compound CCOCCOC1=CC=CC=C1C1=CC(=O)C2=CC(C(=O)OC)=CC=C2O1 MTGWPWPIDLQCPQ-UHFFFAOYSA-N 0.000 description 1
- VFRPYBIGSSNAJS-UHFFFAOYSA-N methyl 2-benzoyloxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1 VFRPYBIGSSNAJS-UHFFFAOYSA-N 0.000 description 1
- RDAALIJZJHPRRP-UHFFFAOYSA-N methyl 2-propan-2-yloxybenzoate Chemical compound COC(=O)C1=CC=CC=C1OC(C)C RDAALIJZJHPRRP-UHFFFAOYSA-N 0.000 description 1
- JDGVFXOHSDRXGK-UHFFFAOYSA-N methyl 3-acetyl-4-hydroxy-5-propylbenzoate Chemical compound CCCC1=CC(C(=O)OC)=CC(C(C)=O)=C1O JDGVFXOHSDRXGK-UHFFFAOYSA-N 0.000 description 1
- BWMZRJNKUBWRFP-UHFFFAOYSA-N methyl 4-oxo-2-(2-propan-2-yloxyphenyl)chromene-6-carboxylate Chemical compound C=1C(=O)C2=CC(C(=O)OC)=CC=C2OC=1C1=CC=CC=C1OC(C)C BWMZRJNKUBWRFP-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
- 229960001238 methylnicotinate Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- 230000003472 neutralizing 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
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus 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
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 201000004193 respiratory failure Diseases 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940076279 serotonin 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
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 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
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000004094 surface-active agent Substances 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
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT3208973 | 1973-12-27 | ||
| IT2477774A IT1045480B (it) | 1974-07-04 | 1974-07-04 | Acidi 2 vinil cromon carbossilici sostituiti |
| IT2524474 | 1974-07-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2461670A1 true DE2461670A1 (de) | 1975-07-10 |
Family
ID=27273401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742461670 Withdrawn DE2461670A1 (de) | 1973-12-27 | 1974-12-27 | 5,6-benzo-gamma-pyronderivate, verfahren zu ihrer herstellung und ihre verwendung in pharmazeutischen zubereitungen |
Country Status (16)
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0834510A3 (en) * | 1996-10-04 | 1998-04-29 | Kowa Co. Ltd. | Flavone derivative and medicine comprising the same |
| WO2013076315A3 (en) * | 2012-04-27 | 2013-07-18 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
| WO2014184073A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4160028A (en) * | 1977-08-02 | 1979-07-03 | Carlo Erba S.P.A. | Substituted 2-cyclopropyl-chromones and pharmaceutical compositions and use thereof |
| IT1134205B (it) * | 1980-11-11 | 1986-08-13 | Bonomelli Spa | Processo per la produzione di derivati flavonici ad attivita' medicinale |
| FR2516922A1 (fr) * | 1981-11-25 | 1983-05-27 | Lipha | Acides (oxo-4-4h-(1)-benzopyran-8-yl) alcanoiques, sels et derives, preparation et medicament les contenant |
| US4525356A (en) * | 1982-11-02 | 1985-06-25 | Hokuriku Pharmaceutical Co., Ltd. | N-substituted flavone-8-carboxamides |
| IL108841A0 (en) * | 1993-03-10 | 1994-06-24 | Pfizer Res & Dev | Benzopyrans |
-
1974
- 1974-12-17 GB GB54453/74A patent/GB1479518A/en not_active Expired
- 1974-12-23 HU HU74EA00000142A patent/HU171874B/hu unknown
- 1974-12-23 SE SE7416231A patent/SE417427B/xx unknown
- 1974-12-23 DK DK680474A patent/DK680474A/da not_active Application Discontinuation
- 1974-12-24 CH CH1731074A patent/CH616934A5/de not_active IP Right Cessation
- 1974-12-24 NL NL7416873A patent/NL7416873A/xx not_active Application Discontinuation
- 1974-12-27 CS CS749033A patent/CS202543B2/cs unknown
- 1974-12-27 JP JP753008A patent/JPS5634595B2/ja not_active Expired
- 1974-12-27 AT AT1034174A patent/AT345830B/de not_active IP Right Cessation
- 1974-12-27 SU SU742098258A patent/SU611590A3/ru active
- 1974-12-27 DE DE19742461670 patent/DE2461670A1/de not_active Withdrawn
- 1974-12-27 CA CA216,961A patent/CA1061353A/en not_active Expired
- 1974-12-27 FI FI3742/74A patent/FI67080C/fi active
- 1974-12-27 FR FR7443125A patent/FR2255894B1/fr not_active Expired
- 1974-12-27 NO NO744714A patent/NO144110C/no unknown
-
1975
- 1975-01-10 IL IL46423A patent/IL46423A/xx unknown
-
1978
- 1978-03-13 CH CH388578A patent/CH616935A5/de not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0834510A3 (en) * | 1996-10-04 | 1998-04-29 | Kowa Co. Ltd. | Flavone derivative and medicine comprising the same |
| US6136848A (en) * | 1996-10-04 | 2000-10-24 | Kowa Co., Ltd. | Flavone derivative and medicine comprising the same |
| WO2013076315A3 (en) * | 2012-04-27 | 2013-07-18 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
| WO2014184073A1 (en) * | 2013-05-15 | 2014-11-20 | Basf Se | Substituted n-(tetrazol-5-yl)- and n-(triazol-5-yl)arylcarboxamide compounds and their use as herbicides |
Also Published As
| Publication number | Publication date |
|---|---|
| SE417427B (sv) | 1981-03-16 |
| AU7687874A (en) | 1976-06-24 |
| HU171874B (hu) | 1978-04-28 |
| CS202543B2 (en) | 1981-01-30 |
| ATA1034174A (de) | 1978-02-15 |
| AT345830B (de) | 1978-10-10 |
| JPS5634595B2 (enrdf_load_stackoverflow) | 1981-08-11 |
| IL46423A0 (en) | 1975-05-22 |
| CH616935A5 (en) | 1980-04-30 |
| IL46423A (en) | 1979-03-12 |
| FI67080C (fi) | 1985-01-10 |
| CA1061353A (en) | 1979-08-28 |
| CH616934A5 (en) | 1980-04-30 |
| JPS50129568A (enrdf_load_stackoverflow) | 1975-10-13 |
| FR2255894B1 (enrdf_load_stackoverflow) | 1978-07-21 |
| SU611590A3 (ru) | 1978-06-15 |
| FI374274A7 (enrdf_load_stackoverflow) | 1975-06-28 |
| NL7416873A (nl) | 1975-07-01 |
| DK680474A (enrdf_load_stackoverflow) | 1975-08-25 |
| NO744714L (enrdf_load_stackoverflow) | 1975-07-21 |
| NO144110C (no) | 1981-06-24 |
| FI67080B (fi) | 1984-09-28 |
| GB1479518A (en) | 1977-07-13 |
| SE7416231L (enrdf_load_stackoverflow) | 1975-06-30 |
| NO144110B (no) | 1981-03-16 |
| FR2255894A1 (enrdf_load_stackoverflow) | 1975-07-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| 8127 | New person/name/address of the applicant |
Owner name: FARMITALIA CARLO ERBA S.P.A., 20159 MILANO, IT |
|
| 8130 | Withdrawal |