CA1090366A - N-substituted aralkylanilines having hypolipidaemic activity - Google Patents
N-substituted aralkylanilines having hypolipidaemic activityInfo
- Publication number
- CA1090366A CA1090366A CA295,386A CA295386A CA1090366A CA 1090366 A CA1090366 A CA 1090366A CA 295386 A CA295386 A CA 295386A CA 1090366 A CA1090366 A CA 1090366A
- Authority
- CA
- Canada
- Prior art keywords
- group
- compound
- alkyl
- formulae
- chlorobenzyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 230000000055 hyoplipidemic effect Effects 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 37
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 150000002148 esters Chemical class 0.000 claims abstract description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
- 239000001257 hydrogen Substances 0.000 claims abstract description 18
- 238000002360 preparation method Methods 0.000 claims abstract description 18
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract description 17
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 15
- 150000002367 halogens Chemical class 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 7
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
- 150000001733 carboxylic acid esters Chemical group 0.000 claims abstract description 6
- LJDZFAPLPVPTBD-UHFFFAOYSA-N nitroformic acid Chemical compound OC(=O)[N+]([O-])=O LJDZFAPLPVPTBD-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- KMCKWPLCLFTTHO-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCC1=CC=C(Cl)C=C1 KMCKWPLCLFTTHO-UHFFFAOYSA-N 0.000 claims description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000002904 solvent Substances 0.000 claims 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 claims description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 4
- SGISGADIVHZDDD-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-formylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N(C=O)CC1=CC=C(Cl)C=C1 SGISGADIVHZDDD-UHFFFAOYSA-N 0.000 claims description 4
- SQFHRURLSSDTKM-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-methylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N(C)CC1=CC=C(Cl)C=C1 SQFHRURLSSDTKM-UHFFFAOYSA-N 0.000 claims description 4
- NAAOIPKZZWJUTI-UHFFFAOYSA-N ethyl 4-[acetyl-[(4-chlorophenyl)methyl]amino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N(C(C)=O)CC1=CC=C(Cl)C=C1 NAAOIPKZZWJUTI-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 3
- BPLAUSJLIYAACY-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-ethoxycarbonylamino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1N(C(=O)OCC)CC1=CC=C(Cl)C=C1 BPLAUSJLIYAACY-UHFFFAOYSA-N 0.000 claims description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 claims description 2
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 claims description 2
- RENSEAZRACAORT-UHFFFAOYSA-N methyl 4-[(4-fluorophenyl)methylamino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NCC1=CC=C(F)C=C1 RENSEAZRACAORT-UHFFFAOYSA-N 0.000 claims description 2
- 239000012312 sodium hydride Substances 0.000 claims description 2
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 6
- 150000002431 hydrogen Chemical class 0.000 claims 5
- DEKLNEJTQWIVAB-UHFFFAOYSA-N ethyl 4-[3-(4-chlorophenyl)propylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1NCCCC1=CC=C(Cl)C=C1 DEKLNEJTQWIVAB-UHFFFAOYSA-N 0.000 claims 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 235000019256 formaldehyde Nutrition 0.000 claims 1
- 229960004279 formaldehyde Drugs 0.000 claims 1
- NRLJDXXASNTYLV-UHFFFAOYSA-N methyl 4-[ethoxycarbonyl-[(4-fluorophenyl)methyl]amino]benzoate Chemical compound C=1C=C(C(=O)OC)C=CC=1N(C(=O)OCC)CC1=CC=C(F)C=C1 NRLJDXXASNTYLV-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 18
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 239000000460 chlorine Substances 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 239000003981 vehicle Substances 0.000 description 7
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- 125000001309 chloro group Chemical group Cl* 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 235000005911 diet Nutrition 0.000 description 5
- 230000037213 diet Effects 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 229960001866 silicon dioxide Drugs 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- GGHHPQCHXDLICT-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-ethylamino]benzoate Chemical compound C1=CC(C(=O)OCC)=CC=C1N(CC)CC1=CC=C(Cl)C=C1 GGHHPQCHXDLICT-UHFFFAOYSA-N 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
- 235000010356 sorbitol Nutrition 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 240000007472 Leucaena leucocephala Species 0.000 description 2
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- OZEFEPJVYTWOLN-UHFFFAOYSA-N ethyl 4-[(4-fluorophenyl)methyl-hexylamino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1N(CCCCCC)CC1=CC=C(F)C=C1 OZEFEPJVYTWOLN-UHFFFAOYSA-N 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 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
- 125000002887 hydroxy group Chemical group [H]O* 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
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 2
- 238000006386 neutralization reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000001117 sulphuric acid Substances 0.000 description 2
- 235000011149 sulphuric acid Nutrition 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- XINQFOMFQFGGCQ-UHFFFAOYSA-L (2-dodecoxy-2-oxoethyl)-[6-[(2-dodecoxy-2-oxoethyl)-dimethylazaniumyl]hexyl]-dimethylazanium;dichloride Chemical compound [Cl-].[Cl-].CCCCCCCCCCCCOC(=O)C[N+](C)(C)CCCCCC[N+](C)(C)CC(=O)OCCCCCCCCCCCC XINQFOMFQFGGCQ-UHFFFAOYSA-L 0.000 description 1
- GRNXGBGHNMMWMF-UHFFFAOYSA-N (4-chlorophenyl)methyl-(4-ethoxycarbonylphenyl)carbamic acid Chemical compound CCOC(=O)C1=CC=C(C=C1)N(CC2=CC=C(C=C2)Cl)C(=O)O GRNXGBGHNMMWMF-UHFFFAOYSA-N 0.000 description 1
- IZXWCDITFDNEBY-UHFFFAOYSA-N 1-(chloromethyl)-4-fluorobenzene Chemical compound FC1=CC=C(CCl)C=C1 IZXWCDITFDNEBY-UHFFFAOYSA-N 0.000 description 1
- UBUQFSINNOCKJE-UHFFFAOYSA-N 1-[4-[(4-chlorophenyl)methyl-methylamino]phenyl]propan-2-one Chemical compound C=1C=C(CC(C)=O)C=CC=1N(C)CC1=CC=C(Cl)C=C1 UBUQFSINNOCKJE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- 239000004150 EU approved colour Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 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 1
- 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 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 239000004141 Sodium laurylsulphate Substances 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000005205 alkoxycarbonyloxyalkyl group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 235000018823 dietary intake Nutrition 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000008157 edible vegetable oil Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- AREHURDQIAGEHR-UHFFFAOYSA-N ethyl 3-[4-[(4-chlorophenyl)methyl-methylamino]phenyl]propanoate Chemical compound C1=CC(CCC(=O)OCC)=CC=C1N(C)CC1=CC=C(Cl)C=C1 AREHURDQIAGEHR-UHFFFAOYSA-N 0.000 description 1
- GBULBVLBVDIQMK-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-decylamino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1N(CCCCCCCCCC)CC1=CC=C(Cl)C=C1 GBULBVLBVDIQMK-UHFFFAOYSA-N 0.000 description 1
- LDXLITUAOXAJBX-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-heptylamino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1N(CCCCCCC)CC1=CC=C(Cl)C=C1 LDXLITUAOXAJBX-UHFFFAOYSA-N 0.000 description 1
- UAVCWILDJOBOEN-UHFFFAOYSA-N ethyl 4-[(4-chlorophenyl)methyl-propylamino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1N(CCC)CC1=CC=C(Cl)C=C1 UAVCWILDJOBOEN-UHFFFAOYSA-N 0.000 description 1
- OFBMDVVAAUKWHE-UHFFFAOYSA-N ethyl 4-[butyl-[(4-chlorophenyl)methyl]amino]benzoate Chemical compound C=1C=C(C(=O)OCC)C=CC=1N(CCCC)CC1=CC=C(Cl)C=C1 OFBMDVVAAUKWHE-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000000350 glycoloyl group Chemical group O=C([*])C([H])([H])O[H] 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 230000000999 hypotriglyceridemic effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002500 ions Chemical class 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
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000000686 lactone group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000008176 lyophilized powder Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 229940006093 opthalmologic coloring agent diagnostic Drugs 0.000 description 1
- 239000003182 parenteral nutrition solution Substances 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000009938 salting Methods 0.000 description 1
- 238000007789 sealing 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical group CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2659/77A GB1576841A (en) | 1977-01-22 | 1977-01-22 | Substituted n-acyl phenylamine compounds having hypolipidaemic activity |
| GB2659/77 | 1977-01-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1090366A true CA1090366A (en) | 1980-11-25 |
Family
ID=9743494
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA295,386A Expired CA1090366A (en) | 1977-01-22 | 1978-01-20 | N-substituted aralkylanilines having hypolipidaemic activity |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4271188A (en, 2012) |
| JP (1) | JPS53105446A (en, 2012) |
| AU (1) | AU519414B2 (en, 2012) |
| BE (1) | BE863156A (en, 2012) |
| CA (1) | CA1090366A (en, 2012) |
| DE (1) | DE2802444A1 (en, 2012) |
| DK (1) | DK31478A (en, 2012) |
| ES (1) | ES466257A1 (en, 2012) |
| FI (1) | FI780185A7 (en, 2012) |
| FR (1) | FR2377997A1 (en, 2012) |
| GB (1) | GB1576841A (en, 2012) |
| IE (1) | IE46647B1 (en, 2012) |
| IL (1) | IL53861A (en, 2012) |
| NL (1) | NL7800709A (en, 2012) |
| NZ (1) | NZ186258A (en, 2012) |
| SE (1) | SE7800676L (en, 2012) |
| ZA (1) | ZA78358B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4375478A (en) * | 1982-03-02 | 1983-03-01 | Abbott Laboratories | Aminobenzoic acid derivatives |
| JPS59152348A (ja) * | 1983-02-19 | 1984-08-31 | Kaken Pharmaceut Co Ltd | ビフエニリルプロピオン酸エステル誘導体およびその製造法 |
| US5196567A (en) * | 1983-02-19 | 1993-03-23 | Kaken Pharmaceutical Co., Ltd. | Biphenylylpropionic acid derivative, process for preparing the same and pharmaceutical composition containing the same |
| IT1201113B (it) * | 1986-01-10 | 1989-01-27 | Fmc Corp | Composti erbicidi |
| US5741926A (en) * | 1997-02-12 | 1998-04-21 | Shaman Pharmaceuticals, Inc. | Aniline derivatives having antihyperglycemic activity |
| EP1542967A1 (en) * | 2002-09-20 | 2005-06-22 | Pfizer Products Inc. | Amide and sulfonamide ligands for the estrogen receptor |
| JP2010512415A (ja) * | 2006-12-11 | 2010-04-22 | ワイス エルエルシー | イオンチャネルモジュレータ− |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2137211B1 (en, 2012) * | 1971-05-17 | 1974-08-02 | Bouchara Emile | |
| FR2193579A2 (en) * | 1972-07-25 | 1974-02-22 | Bouchara Emile | Para amino phenyl acetic acids - analgesics and antiinflammatories, prepd. by alkylation of prim amino acid |
| US4185115A (en) * | 1975-03-12 | 1980-01-22 | American Cyanamid Company | Antilipidemic para-[aryl(alkyl or alkenyl)amino]-benzoic acid derivatives |
-
1977
- 1977-01-22 GB GB2659/77A patent/GB1576841A/en not_active Expired
-
1978
- 1978-01-18 NZ NZ186258A patent/NZ186258A/xx unknown
- 1978-01-19 SE SE7800676A patent/SE7800676L/xx unknown
- 1978-01-19 ZA ZA00780358A patent/ZA78358B/xx unknown
- 1978-01-20 DE DE19782802444 patent/DE2802444A1/de not_active Withdrawn
- 1978-01-20 DK DK31478A patent/DK31478A/da unknown
- 1978-01-20 IE IE128/78A patent/IE46647B1/en unknown
- 1978-01-20 AU AU32612/78A patent/AU519414B2/en not_active Expired
- 1978-01-20 BE BE184518A patent/BE863156A/xx unknown
- 1978-01-20 NL NL7800709A patent/NL7800709A/xx not_active Application Discontinuation
- 1978-01-20 IL IL53861A patent/IL53861A/xx unknown
- 1978-01-20 CA CA295,386A patent/CA1090366A/en not_active Expired
- 1978-01-20 FI FI780185A patent/FI780185A7/fi not_active Application Discontinuation
- 1978-01-23 JP JP608878A patent/JPS53105446A/ja active Pending
- 1978-01-23 FR FR7801750A patent/FR2377997A1/fr active Granted
- 1978-01-23 ES ES466257A patent/ES466257A1/es not_active Expired
-
1979
- 1979-12-17 US US06/104,418 patent/US4271188A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SE7800676L (sv) | 1978-07-23 |
| ZA78358B (en) | 1979-01-31 |
| DK31478A (da) | 1978-07-23 |
| AU3261278A (en) | 1979-07-26 |
| NL7800709A (nl) | 1978-07-25 |
| NZ186258A (en) | 1979-10-25 |
| IL53861A (en) | 1981-07-31 |
| DE2802444A1 (de) | 1978-07-27 |
| FR2377997A1 (fr) | 1978-08-18 |
| JPS53105446A (en) | 1978-09-13 |
| BE863156A (fr) | 1978-07-20 |
| IE780128L (en) | 1978-07-22 |
| ES466257A1 (es) | 1979-01-16 |
| IL53861A0 (en) | 1978-04-30 |
| FI780185A7 (fi) | 1978-07-23 |
| AU519414B2 (en) | 1981-12-03 |
| FR2377997B1 (en, 2012) | 1980-04-25 |
| US4271188A (en) | 1981-06-02 |
| IE46647B1 (en) | 1983-08-10 |
| GB1576841A (en) | 1980-10-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR910002892B1 (ko) | 술포늄 화합물의 제조방법 | |
| CA2083597A1 (en) | Antitussive and mucus regulating agent, a process for the preparation thereof and pharmaceutical compositions containing it | |
| US4320137A (en) | Derivatives of perhydro-aza-heterocycles | |
| CA1090366A (en) | N-substituted aralkylanilines having hypolipidaemic activity | |
| SU664561A3 (ru) | Способ получени производных 2-/4(ациламиноалкил)-фенокси/-алкилкарбоновой кислоты или их солей | |
| GB1576007A (en) | Hypolipidaemic compositions | |
| EP0272478B1 (en) | Glycyrrhetic acid derivatives and use thereof | |
| US2901507A (en) | Alkylaminoalkyl 2,4,6-trimethylbenzamide | |
| CA1043806A (en) | Phenoxy-alkyl-carboxylic acid derivatives | |
| IE57702B1 (en) | P-oxybenzoic acid derivatives,methods for preparing them and their use for the preparation of medicaments with hypolipemic activity | |
| CA1040213A (en) | Cycloalkyl phenoxy carboxylic acid derivatives | |
| US4409240A (en) | Derivatives of dihydroxybenzoic acid and pharmaceutical composition thereof | |
| US4450172A (en) | Antihypertensive polyhalohydroxyisopropyl phenylalka(e)noic acid esters of alkylaminohydroxypropyloxyphenylalkyl alcohols | |
| US3513201A (en) | Process for preparing 5-(3-alkylaminopropyl)-5h-dibenzo(a,d)cycloheptenes | |
| EP0806412B1 (en) | Benzene derivatives | |
| EP0044541B1 (en) | Aminocarboxylic acids, amino alcohols, or the derivatives thereof, processes for production thereof, and pharmaceutical composition, containing at least one of these compounds | |
| US4758585A (en) | Saturated cycloalkyl (B) pyrrol-1 (2H)- acetic acid amides and derivatives thereof | |
| US4621097A (en) | Saturated cycloalkyl[c] pyrrole-2(1H)-acetic acid amides and derivatives thereof | |
| US4091029A (en) | N-pentafluoropropionyl and n-heptafluorobutyryl proline | |
| EP0066254B1 (en) | Mercapto amino acids, process for their preparation and pharmaceutical compositions containing them | |
| KR100273603B1 (ko) | 치환된 벤조에이트 유도체 | |
| EP0365210A1 (en) | Hydroxamic acid derivatives | |
| US3465002A (en) | (succinimidoaryloxy)alkanoic acids,esters and amides thereof | |
| US3686291A (en) | Thio derivatives of 2-hydroxy-3-naphthioc acid | |
| US4161532A (en) | N-(1'-ethyl-2'-oxo-5'-pyrrolidinylmethyl) benzamide compounds and derivatives, method of preparation and pharmaceutical preparations |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |