NO780558L - Benzoesyre og dens derivater samt fremgangsmaate til deres fremstilling - Google Patents
Benzoesyre og dens derivater samt fremgangsmaate til deres fremstillingInfo
- Publication number
- NO780558L NO780558L NO780558A NO780558A NO780558L NO 780558 L NO780558 L NO 780558L NO 780558 A NO780558 A NO 780558A NO 780558 A NO780558 A NO 780558A NO 780558 L NO780558 L NO 780558L
- Authority
- NO
- Norway
- Prior art keywords
- benzoic acid
- alkyl
- atoms
- ethyl
- acid
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 15
- 239000002253 acid Substances 0.000 title claims description 8
- 238000002360 preparation method Methods 0.000 title claims description 5
- 239000005711 Benzoic acid Substances 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- -1 amino compound Chemical class 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 239000008280 blood Substances 0.000 claims description 5
- 210000004369 blood Anatomy 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 150000001558 benzoic acid derivatives Chemical class 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 238000003756 stirring Methods 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- 235000010233 benzoic acid Nutrition 0.000 description 8
- 239000000155 melt Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- WCLAVUGBGKPHOR-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid;sodium Chemical compound [Na].NCCC1=CC=C(C(O)=O)C=C1 WCLAVUGBGKPHOR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000000052 vinegar Substances 0.000 description 3
- 235000021419 vinegar Nutrition 0.000 description 3
- PTLIJJIFWPKVBO-UHFFFAOYSA-N 2-butoxy-6-methylpyridine-3-carboxylic acid Chemical compound CCCCOC1=NC(C)=CC=C1C(O)=O PTLIJJIFWPKVBO-UHFFFAOYSA-N 0.000 description 2
- IBRSSZOHCGUTHI-UHFFFAOYSA-N 2-chloropyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1Cl IBRSSZOHCGUTHI-UHFFFAOYSA-N 0.000 description 2
- ROYGTXYAIRANJK-UHFFFAOYSA-N 5-chloro-2-cyclohexyloxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CN=C1OC1CCCCC1 ROYGTXYAIRANJK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- YFLWCZIVJVCWNQ-UHFFFAOYSA-N ethyl 4-(2-aminoethyl)benzoate;hydrochloride Chemical compound Cl.CCOC(=O)C1=CC=C(CCN)C=C1 YFLWCZIVJVCWNQ-UHFFFAOYSA-N 0.000 description 2
- 235000019439 ethyl acetate Nutrition 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 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
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KWQCKCPGTVWZNS-UHFFFAOYSA-N 1-(4-methylcyclohexyl)-2-oxopyridine-3-carbonyl chloride Chemical compound C1CC(C)CCC1N1C(=O)C(C(Cl)=O)=CC=C1 KWQCKCPGTVWZNS-UHFFFAOYSA-N 0.000 description 1
- PJRXTBHNOYATHD-UHFFFAOYSA-N 1-benzyl-2-oxopyridine-3-carbonyl chloride Chemical compound O=C1C(C(=O)Cl)=CC=CN1CC1=CC=CC=C1 PJRXTBHNOYATHD-UHFFFAOYSA-N 0.000 description 1
- HIUQUJPKXXCPCM-UHFFFAOYSA-N 1-cyclohexyl-2-oxopyridine-3-carbonyl chloride Chemical compound O=C1C(C(=O)Cl)=CC=CN1C1CCCCC1 HIUQUJPKXXCPCM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VXZBYIWNGKSFOJ-UHFFFAOYSA-N 2-[4-[5-(2,3-dihydro-1H-inden-2-ylamino)pyrazin-2-yl]pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC=1N=CC(=NC=1)C=1C=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2 VXZBYIWNGKSFOJ-UHFFFAOYSA-N 0.000 description 1
- UNJYEEUNZNUDMH-UHFFFAOYSA-N 2-butoxy-5-chloro-6-methylpyridine-3-carboxylic acid Chemical compound CCCCOC1=NC(C)=C(Cl)C=C1C(O)=O UNJYEEUNZNUDMH-UHFFFAOYSA-N 0.000 description 1
- RKMZJKICIRHTOE-UHFFFAOYSA-N 2-butoxy-5-chloropyridine-3-carboxylic acid Chemical compound CCCCOC1=NC=C(Cl)C=C1C(O)=O RKMZJKICIRHTOE-UHFFFAOYSA-N 0.000 description 1
- FKIQXAJOJKMRJI-UHFFFAOYSA-N 2-butoxypyridine-3-carboxylic acid Chemical compound CCCCOC1=NC=CC=C1C(O)=O FKIQXAJOJKMRJI-UHFFFAOYSA-N 0.000 description 1
- ACQXHCHKMFYDPM-UHFFFAOYSA-N 2-chloro-6-methylpyridine-3-carboxylic acid Chemical compound CC1=CC=C(C(O)=O)C(Cl)=N1 ACQXHCHKMFYDPM-UHFFFAOYSA-N 0.000 description 1
- DTAUTMCCLAWIDK-UHFFFAOYSA-N 2-cyclohexyloxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1CCCCC1 DTAUTMCCLAWIDK-UHFFFAOYSA-N 0.000 description 1
- XCMJQQOMGWGGSI-UHFFFAOYSA-N 2-ethoxypyridine-3-carboxylic acid Chemical compound CCOC1=NC=CC=C1C(O)=O XCMJQQOMGWGGSI-UHFFFAOYSA-N 0.000 description 1
- FCHZXTVVRIZEIW-UHFFFAOYSA-N 2-octoxypyridine-3-carboxylic acid Chemical compound CCCCCCCCOC1=NC=CC=C1C(O)=O FCHZXTVVRIZEIW-UHFFFAOYSA-N 0.000 description 1
- IXAGPDBXJBZELX-UHFFFAOYSA-N 2-pentoxypyridine-3-carboxylic acid Chemical compound CCCCCOC1=NC=CC=C1C(O)=O IXAGPDBXJBZELX-UHFFFAOYSA-N 0.000 description 1
- CQGAXJGXGLVFGJ-UHFFFAOYSA-N 2-phenoxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OC1=CC=CC=C1 CQGAXJGXGLVFGJ-UHFFFAOYSA-N 0.000 description 1
- FUNQFOUBLCEFIK-UHFFFAOYSA-N 2-phenylmethoxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1OCC1=CC=CC=C1 FUNQFOUBLCEFIK-UHFFFAOYSA-N 0.000 description 1
- UETCSFANSYKLNJ-UHFFFAOYSA-N 2-propoxypyridine-3-carboxylic acid Chemical compound CCCOC1=NC=CC=C1C(O)=O UETCSFANSYKLNJ-UHFFFAOYSA-N 0.000 description 1
- BANRONBXBRYLQF-UHFFFAOYSA-N 4-(2-aminoethyl)-2-methoxybenzoic acid Chemical compound COC1=CC(CCN)=CC=C1C(O)=O BANRONBXBRYLQF-UHFFFAOYSA-N 0.000 description 1
- MRBFWTDIRYEDBQ-UHFFFAOYSA-N 4-(2-aminoethyl)benzoic acid Chemical compound NCCC1=CC=C(C(O)=O)C=C1 MRBFWTDIRYEDBQ-UHFFFAOYSA-N 0.000 description 1
- KKWWQFUWIBHMJS-UHFFFAOYSA-N 4-[2-[(2-pentoxypyridine-3-carbonyl)amino]ethyl]benzoic acid Chemical compound C(CCCC)OC1=C(C(=O)NCCC2=CC=C(C(=O)O)C=C2)C=CC=N1 KKWWQFUWIBHMJS-UHFFFAOYSA-N 0.000 description 1
- CVICEEPAFUYBJG-UHFFFAOYSA-N 5-chloro-2,2-difluoro-1,3-benzodioxole Chemical group C1=C(Cl)C=C2OC(F)(F)OC2=C1 CVICEEPAFUYBJG-UHFFFAOYSA-N 0.000 description 1
- GHWHXENNEIKRJU-UHFFFAOYSA-N 5-chloro-2-(4-methylcyclohexyl)oxypyridine-3-carboxylic acid Chemical compound C1CC(C)CCC1OC1=NC=C(Cl)C=C1C(O)=O GHWHXENNEIKRJU-UHFFFAOYSA-N 0.000 description 1
- PLTFOXPXBITHOG-UHFFFAOYSA-N 5-chloro-2-(cyclohexylmethoxy)pyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CN=C1OCC1CCCCC1 PLTFOXPXBITHOG-UHFFFAOYSA-N 0.000 description 1
- DGGFVLDNJPOVKG-UHFFFAOYSA-N 5-chloro-2-cyclopentyloxypyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC(Cl)=CN=C1OC1CCCC1 DGGFVLDNJPOVKG-UHFFFAOYSA-N 0.000 description 1
- DTIBPOFHVJBUSH-UHFFFAOYSA-N 5-chloro-2-ethoxypyridine-3-carboxylic acid Chemical compound CCOC1=NC=C(Cl)C=C1C(O)=O DTIBPOFHVJBUSH-UHFFFAOYSA-N 0.000 description 1
- LYCKNKNFIXFTNQ-UHFFFAOYSA-N 5-chloro-2-pentoxypyridine-3-carboxylic acid Chemical compound CCCCCOC1=NC=C(Cl)C=C1C(O)=O LYCKNKNFIXFTNQ-UHFFFAOYSA-N 0.000 description 1
- YYAWQOUZICTGSQ-UHFFFAOYSA-N 5-chloro-2-propoxypyridine-3-carboxylic acid Chemical compound CCCOC1=NC=C(Cl)C=C1C(O)=O YYAWQOUZICTGSQ-UHFFFAOYSA-N 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001540 azides Chemical class 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- VSSAZBXXNIABDN-UHFFFAOYSA-N cyclohexylmethanol Chemical compound OCC1CCCCC1 VSSAZBXXNIABDN-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000002497 iodine compounds Chemical class 0.000 description 1
- 150000004715 keto acids Chemical class 0.000 description 1
- 239000006166 lysate Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 235000013336 milk Nutrition 0.000 description 1
- 239000008267 milk Substances 0.000 description 1
- 210000004080 milk Anatomy 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000011664 nicotinic acid Substances 0.000 description 1
- 229960003512 nicotinic acid Drugs 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229940127017 oral antidiabetic Drugs 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- ILUJQPXNXACGAN-UHFFFAOYSA-N ortho-methoxybenzoic acid Natural products COC1=CC=CC=C1C(O)=O ILUJQPXNXACGAN-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 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
- 238000004809 thin layer chromatography Methods 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
- 230000009466 transformation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
-
- 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772706977 DE2706977A1 (de) | 1977-02-18 | 1977-02-18 | Benzoesaeuren und deren derivate sowie verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO780558L true NO780558L (no) | 1978-08-21 |
Family
ID=6001556
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO780558A NO780558L (no) | 1977-02-18 | 1978-02-17 | Benzoesyre og dens derivater samt fremgangsmaate til deres fremstilling |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US4181658A (de) |
| JP (1) | JPS53103477A (de) |
| AT (1) | AT360534B (de) |
| AU (1) | AU3337678A (de) |
| BE (1) | BE864112A (de) |
| CA (1) | CA1113473A (de) |
| CH (1) | CH645625A5 (de) |
| DE (1) | DE2706977A1 (de) |
| DK (1) | DK71278A (de) |
| ES (1) | ES466910A1 (de) |
| FI (1) | FI780491A7 (de) |
| FR (1) | FR2381028A1 (de) |
| GB (1) | GB1601195A (de) |
| GR (1) | GR78247B (de) |
| IL (1) | IL54058A0 (de) |
| NL (1) | NL7801859A (de) |
| NO (1) | NO780558L (de) |
| PT (1) | PT67672B (de) |
| SE (1) | SE7801885L (de) |
| ZA (1) | ZA78946B (de) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3063878D1 (en) * | 1979-07-13 | 1983-07-28 | Thomae Gmbh Dr K | Derivatives of carboxylic acids, their preparation and medicaments containing them |
| DE3211934A1 (de) * | 1982-03-31 | 1983-10-13 | Hoechst Ag, 6230 Frankfurt | Salicylsaeurederivate, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen und ihre verwendung |
| EP0195582B1 (de) * | 1985-03-14 | 1990-01-24 | SMITH KLINE DAUELSBERG GmbH | 5-Aminosalicylsäurederivate von nicht-steroidalen entzündungshemmenden Sauren |
| CN1254335A (zh) * | 1997-04-04 | 2000-05-24 | 辉瑞产品公司 | 烟酰胺衍生物 |
| RU2290403C2 (ru) * | 2000-12-28 | 2006-12-27 | Дайити Фармасьютикал Ко., Лтд. | Ингибиторы vla-4 |
| ATE293109T1 (de) * | 2001-01-31 | 2005-04-15 | Pfizer Prod Inc | Nikotinsäureamid-derivate und ihre mimetika als inhibitoren von pde4-isozyms |
| US7250518B2 (en) * | 2001-01-31 | 2007-07-31 | Pfizer Inc. | Nicotinamide acids, amides, and their mimetics active as inhibitors of PDE4 isozymes |
| TW200500341A (en) * | 2002-11-12 | 2005-01-01 | Astrazeneca Ab | Novel compounds |
| US7691894B2 (en) * | 2003-07-24 | 2010-04-06 | Daiichi Pharmaceutical Co., Ltd. | Cyclohexanecarboxylic acid compound |
| SE0302323D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| SE0302324D0 (sv) * | 2003-08-28 | 2003-08-28 | Astrazeneca Ab | Novel compounds |
| WO2005021508A1 (en) | 2003-09-03 | 2005-03-10 | Pfizer Inc. | Phenyl or pyridyl amide compounds as prostaglandin e2 antagonists |
| SE0302486D0 (sv) * | 2003-09-18 | 2003-09-18 | Astrazeneca Ab | Novel compounds |
| TW200700392A (en) * | 2005-03-16 | 2007-01-01 | Astrazeneca Ab | Novel compounds |
| TW200808763A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds I |
| TW200808771A (en) * | 2006-05-08 | 2008-02-16 | Astrazeneca Ab | Novel compounds II |
| ES2431466T3 (es) * | 2006-06-30 | 2013-11-26 | Sunesis Pharmaceuticals, Inc. | Inhibidores de piridinonil pdk1 |
| KR20100096131A (ko) * | 2007-11-06 | 2010-09-01 | 아스트라제네카 아베 | 특정 2-피라지논 유도체 및 호중구 엘라스타제의 억제제로서의 이의 용도 |
| TW201036957A (en) * | 2009-02-20 | 2010-10-16 | Astrazeneca Ab | Novel salt 628 |
| TWI504395B (zh) | 2009-03-10 | 2015-10-21 | Substituted 3-amino-2-mercaptoquinoline as a KCNQ2 / 3 modifier | |
| TWI461197B (zh) | 2009-03-12 | 2014-11-21 | 2-mercaptoquinoline-3-carboxamide as a KCNQ2 / 3 modifier | |
| TW201038565A (en) | 2009-03-12 | 2010-11-01 | Gruenenthal Gmbh | Substituted 2-mercapto-3-aminopyridines as KCNQ2/3 modulators |
| KR20120099639A (ko) * | 2009-10-02 | 2012-09-11 | 아스트라제네카 아베 | 호중구 엘라스타제의 억제제로서 사용되는 2-피리돈 화합물 |
| DK2609083T3 (da) | 2010-08-27 | 2015-03-30 | Gruenenthal Gmbh | Substituerede 2-oxy-quinolin-3-carboxamider som KCNQ2/3 modulatorer |
| AU2011295406B2 (en) | 2010-08-27 | 2015-08-06 | Grunenthal Gmbh | Substituted 2-amino-quinoline-3-carboxamides as KCNQ2/3 modulators |
| SI2609086T1 (sl) | 2010-08-27 | 2015-04-30 | Gruenenthal Gmbh | Substituirani 2-okso in 2-tiokso-dihidrokinolin-3-karboksamidi kot KCNQ2/3 modulatorji |
| MX2013002295A (es) | 2010-09-01 | 2013-05-09 | Gruenenthal Gmbh | 1-oxo-dihidroisoquinolin-3-carboxamidas sustituidas como moduladores de kcnq2/3. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3879403A (en) * | 1973-05-04 | 1975-04-22 | Pfizer | Benzenesulfonylurea derivatives |
| DE2406200A1 (de) * | 1974-02-09 | 1975-08-14 | Bayer Ag | Verfahren zur herstellung von neuen 3,6-diamino-3,4-dihydropyridonen-2 und ihre verwendung als arzneimittel |
| DE2500157C2 (de) * | 1975-01-03 | 1983-09-15 | Hoechst Ag, 6230 Frankfurt | N-Acyl-4-(2-aminoäthyl)-benzoesäuren, deren Salze und Ester, Verfahren zu deren Herstellung und deren Verwendung |
-
1977
- 1977-02-18 DE DE19772706977 patent/DE2706977A1/de not_active Withdrawn
-
1978
- 1978-02-13 ES ES466910A patent/ES466910A1/es not_active Expired
- 1978-02-14 FR FR7804116A patent/FR2381028A1/fr active Granted
- 1978-02-15 CH CH165978A patent/CH645625A5/de not_active IP Right Cessation
- 1978-02-15 FI FI780491A patent/FI780491A7/fi not_active Application Discontinuation
- 1978-02-16 IL IL54058A patent/IL54058A0/xx unknown
- 1978-02-16 US US05/878,602 patent/US4181658A/en not_active Expired - Lifetime
- 1978-02-17 NL NL7801859A patent/NL7801859A/xx not_active Application Discontinuation
- 1978-02-17 AU AU33376/78A patent/AU3337678A/en active Pending
- 1978-02-17 AT AT118178A patent/AT360534B/de not_active IP Right Cessation
- 1978-02-17 SE SE7801885A patent/SE7801885L/xx unknown
- 1978-02-17 DK DK71278A patent/DK71278A/da unknown
- 1978-02-17 NO NO780558A patent/NO780558L/no unknown
- 1978-02-17 ZA ZA00780946A patent/ZA78946B/xx unknown
- 1978-02-17 CA CA297,158A patent/CA1113473A/en not_active Expired
- 1978-02-17 PT PT67672A patent/PT67672B/de unknown
- 1978-02-18 JP JP1714078A patent/JPS53103477A/ja active Pending
- 1978-02-20 GB GB6598/78A patent/GB1601195A/en not_active Expired
- 1978-02-20 BE BE185297A patent/BE864112A/xx not_active IP Right Cessation
-
1981
- 1981-03-06 GR GR55473A patent/GR78247B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU3337678A (en) | 1979-08-23 |
| NL7801859A (nl) | 1978-08-22 |
| AT360534B (de) | 1981-01-12 |
| FR2381028B1 (de) | 1980-10-24 |
| JPS53103477A (en) | 1978-09-08 |
| FR2381028A1 (fr) | 1978-09-15 |
| ZA78946B (en) | 1979-01-31 |
| ES466910A1 (es) | 1978-10-01 |
| DK71278A (da) | 1978-08-19 |
| IL54058A0 (en) | 1978-04-30 |
| CH645625A5 (de) | 1984-10-15 |
| PT67672A (de) | 1978-03-01 |
| PT67672B (de) | 1979-10-10 |
| US4181658A (en) | 1980-01-01 |
| DE2706977A1 (de) | 1978-08-24 |
| SE7801885L (sv) | 1978-08-19 |
| FI780491A7 (fi) | 1978-08-19 |
| GR78247B (de) | 1984-09-26 |
| GB1601195A (en) | 1981-10-28 |
| CA1113473A (en) | 1981-12-01 |
| BE864112A (fr) | 1978-08-21 |
| ATA118178A (de) | 1980-06-15 |
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