CH650768A5 - Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten. - Google Patents
Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten. Download PDFInfo
- Publication number
- CH650768A5 CH650768A5 CH5116/82A CH511682A CH650768A5 CH 650768 A5 CH650768 A5 CH 650768A5 CH 5116/82 A CH5116/82 A CH 5116/82A CH 511682 A CH511682 A CH 511682A CH 650768 A5 CH650768 A5 CH 650768A5
- Authority
- CH
- Switzerland
- Prior art keywords
- acetanilides
- basic
- formula
- compounds
- methyl
- Prior art date
Links
- 150000008061 acetanilides Chemical class 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 7
- 229940126601 medicinal product Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 18
- 238000001816 cooling Methods 0.000 claims description 14
- -1 nitro, amino Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 241000251730 Chondrichthyes Species 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 239000003416 antiarrhythmic agent Substances 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003589 local anesthetic agent Substances 0.000 claims description 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 1
- 230000003288 anthiarrhythmic effect Effects 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 150000001649 bromium compounds Chemical class 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 150000001805 chlorine compounds Chemical class 0.000 claims 1
- 125000006312 cyclopentyl amino group Chemical group [H]N(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 claims 1
- 150000003840 hydrochlorides Chemical class 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 150000002688 maleic acid derivatives Chemical class 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- WJXVVJBMBBAWQI-UHFFFAOYSA-N n-(2-amino-6-methylphenyl)-2-(diethylamino)acetamide Chemical compound CCN(CC)CC(=O)NC1=C(C)C=CC=C1N WJXVVJBMBBAWQI-UHFFFAOYSA-N 0.000 description 4
- GWVVXBJLIITIRU-UHFFFAOYSA-N 2-(diethylamino)-N-(2-methyl-6-nitrophenyl)acetamide Chemical compound C(C)N(CC(=O)NC1=C(C=CC=C1[N+](=O)[O-])C)CC GWVVXBJLIITIRU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 150000004820 halides Chemical class 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- RWRXLGIHJKXIQY-UHFFFAOYSA-N 1-(2-amino-3-methylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=CC(C)=C1N RWRXLGIHJKXIQY-UHFFFAOYSA-N 0.000 description 2
- PQXGRUUJIFRFGC-UHFFFAOYSA-N 2-amino-3-methylbenzonitrile Chemical compound CC1=CC=CC(C#N)=C1N PQXGRUUJIFRFGC-UHFFFAOYSA-N 0.000 description 2
- DCEPUXBREZCBOH-UHFFFAOYSA-N 2-chloro-n-(2-ethoxy-6-methylphenyl)acetamide Chemical compound CCOC1=CC=CC(C)=C1NC(=O)CCl DCEPUXBREZCBOH-UHFFFAOYSA-N 0.000 description 2
- HHQVWQLHIHVNGR-UHFFFAOYSA-N 2-chloro-n-(2-methyl-6-nitrophenyl)acetamide Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC(=O)CCl HHQVWQLHIHVNGR-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- BAFUTTWRYOSVMT-UHFFFAOYSA-N N-(2-bromo-6-methylphenyl)-2-(diethylamino)acetamide Chemical compound C(C)N(CC(=O)NC1=C(C=CC=C1C)Br)CC BAFUTTWRYOSVMT-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- IFYZUHPFZSHBIW-UHFFFAOYSA-N n-(2-methyl-6-nitrophenyl)-2-piperidin-1-ylacetamide Chemical compound CC1=CC=CC([N+]([O-])=O)=C1NC(=O)CN1CCCCC1 IFYZUHPFZSHBIW-UHFFFAOYSA-N 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- KWQFZJHENVVLKO-UHFFFAOYSA-N 2-(diethylamino)-N-(2-ethoxy-6-methylphenyl)acetamide Chemical compound C(C)N(CC(=O)NC1=C(C=CC=C1C)OCC)CC KWQFZJHENVVLKO-UHFFFAOYSA-N 0.000 description 1
- CWFVSMFYNPGGFM-UHFFFAOYSA-N 2-(diethylamino)-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound CCN(CC)CC(=O)NC1=CC=CC=C1C(F)(F)F CWFVSMFYNPGGFM-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- LDUCMSVRKKDATH-UHFFFAOYSA-N 2-bromo-6-methylaniline Chemical compound CC1=CC=CC(Br)=C1N LDUCMSVRKKDATH-UHFFFAOYSA-N 0.000 description 1
- UENGBOCGGKLVJJ-UHFFFAOYSA-N 2-chloro-1-(2,4-difluorophenyl)ethanone Chemical compound FC1=CC=C(C(=O)CCl)C(F)=C1 UENGBOCGGKLVJJ-UHFFFAOYSA-N 0.000 description 1
- XIIQMFOFZWGXOF-UHFFFAOYSA-N 2-chloro-n-(2-methyl-6-propanoylphenyl)acetamide Chemical compound CCC(=O)C1=CC=CC(C)=C1NC(=O)CCl XIIQMFOFZWGXOF-UHFFFAOYSA-N 0.000 description 1
- BZNNHUKHVZUGGQ-UHFFFAOYSA-N 2-chloro-n-(2-propanoylphenyl)acetamide Chemical compound CCC(=O)C1=CC=CC=C1NC(=O)CCl BZNNHUKHVZUGGQ-UHFFFAOYSA-N 0.000 description 1
- GCSXEMRXTRHXIS-UHFFFAOYSA-N 2-chloro-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)CCl GCSXEMRXTRHXIS-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- YDPXZINXUVCZKH-UHFFFAOYSA-N 2-ethoxy-6-methylaniline Chemical compound CCOC1=CC=CC(C)=C1N YDPXZINXUVCZKH-UHFFFAOYSA-N 0.000 description 1
- PLLAJAIUQAEKKD-UHFFFAOYSA-N 2-pyrrolidin-1-yl-n-[2-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC=C1NC(=O)CN1CCCC1 PLLAJAIUQAEKKD-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 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
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- RPVSUGBUDNVQAJ-UHFFFAOYSA-N N-(2-ethoxy-6-methylphenyl)-2-piperidin-1-ylacetamide Chemical compound N1(CCCCC1)CC(=O)NC1=C(C=CC=C1C)OCC RPVSUGBUDNVQAJ-UHFFFAOYSA-N 0.000 description 1
- DKFSVJLTJMBBOU-UHFFFAOYSA-N N-(2-ethoxy-6-methylphenyl)-2-pyrrolidin-1-ylacetamide Chemical compound N1(CCCC1)CC(=O)NC1=C(C=CC=C1C)OCC DKFSVJLTJMBBOU-UHFFFAOYSA-N 0.000 description 1
- VFFBKGIWYOIKIS-UHFFFAOYSA-N N-(2-propanoylphenyl)-2-pyrrolidin-1-ylacetamide Chemical compound N1(CCCC1)CC(=O)NC1=C(C=CC=C1)C(CC)=O VFFBKGIWYOIKIS-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 238000000297 Sandmeyer reaction Methods 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- BDVSONRJQWXMHG-UHFFFAOYSA-N cyclopentylazanium;chloride Chemical compound Cl.NC1CCCC1 BDVSONRJQWXMHG-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- FRIJBUGBVQZNTB-UHFFFAOYSA-M magnesium;ethane;bromide Chemical compound [Mg+2].[Br-].[CH2-]C FRIJBUGBVQZNTB-UHFFFAOYSA-M 0.000 description 1
- LOQKSYGVWNTCHM-UHFFFAOYSA-N n-(2-amino-6-methylphenyl)-2-piperidin-1-ylacetamide Chemical compound CC1=CC=CC(N)=C1NC(=O)CN1CCCCC1 LOQKSYGVWNTCHM-UHFFFAOYSA-N 0.000 description 1
- WRYADRGFDISCSG-UHFFFAOYSA-N n-(2-chloro-6-methylphenyl)-2-(cyclopropylamino)acetamide Chemical compound CC1=CC=CC(Cl)=C1NC(=O)CNC1CC1 WRYADRGFDISCSG-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229940094025 potassium bicarbonate Drugs 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229940093956 potassium carbonate Drugs 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- CBPYOHALYYGNOE-UHFFFAOYSA-M potassium;3,5-dinitrobenzoate Chemical compound [K+].[O-]C(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 CBPYOHALYYGNOE-UHFFFAOYSA-M 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- 239000007974 sodium acetate buffer Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229940001593 sodium carbonate Drugs 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/16—Amides, e.g. hydroxamic acids
- A61K31/165—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide
- A61K31/167—Amides, e.g. hydroxamic acids having aromatic rings, e.g. colchicine, atenolol, progabide having the nitrogen of a carboxamide group directly attached to the aromatic ring, e.g. lidocaine, paracetamol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/15—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Heart & Thoracic Surgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5116/82A CH650768A5 (de) | 1982-08-27 | 1982-08-27 | Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten. |
| DE19833328186 DE3328186A1 (de) | 1982-08-27 | 1983-08-01 | Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten |
| GB08321953A GB2129424B (en) | 1982-08-27 | 1983-08-15 | Basic acetanilides |
| SE8304456A SE8304456L (sv) | 1982-08-27 | 1983-08-17 | Basiska acetanilider, forfarandr for deras framstellning och lekemedel, som innehaller dessa acetanilider |
| CA000435457A CA1214776A (fr) | 1982-08-27 | 1983-08-26 | Acetanilides, procede de preparation et compose pharmacologique les contenant |
| FR838313761A FR2532306B1 (fr) | 1982-08-27 | 1983-08-26 | Acetanilides basiques, procede pour leur preparation et medicaments en contenant |
| IT48886/83A IT1168212B (it) | 1982-08-27 | 1983-08-26 | Acetanilidi basiche, procedimento per la loro produzione e medicamenti che le contengono |
| JP58157050A JPS59130250A (ja) | 1982-08-27 | 1983-08-27 | 塩基性アセトアニリド、その製造方法およびこのアセトアニリドを含む医薬 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5116/82A CH650768A5 (de) | 1982-08-27 | 1982-08-27 | Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH650768A5 true CH650768A5 (de) | 1985-08-15 |
Family
ID=4288192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH5116/82A CH650768A5 (de) | 1982-08-27 | 1982-08-27 | Basische acetanilide, verfahren zu deren herstellung und arzneimittel, die diese acetanilide enthalten. |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS59130250A (fr) |
| CA (1) | CA1214776A (fr) |
| CH (1) | CH650768A5 (fr) |
| DE (1) | DE3328186A1 (fr) |
| FR (1) | FR2532306B1 (fr) |
| GB (1) | GB2129424B (fr) |
| IT (1) | IT1168212B (fr) |
| SE (1) | SE8304456L (fr) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7067666B2 (en) * | 2003-06-27 | 2006-06-27 | Research Triangle Institute | 7-substituted camptothecin and camptothecin analogs and methods for producing the same |
| BRPI0404222A (pt) * | 2004-06-07 | 2006-02-07 | Fundacao Oswaldo Cruz | Compostos derivados da lidocaìna, composições farmacêuticas contendo os mesmos, uso das respectivas composições farmacêuticas no tratamento, prevenção ou inibição de doenças bem como o método de tratamento, prevenção ou inibição de doenças com as ditas composições farmacêuticas |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE534406A (fr) * | ||||
| GB859355A (fr) * | ||||
| US2689853A (en) * | 1954-09-21 | Certain i | ||
| BE517755A (fr) * | ||||
| NL73080C (fr) * | 1950-03-03 | |||
| GB726864A (en) * | 1952-05-13 | 1955-03-23 | Geistlich Soehne Ag | New ª‰-dialkyl-aminobutyric acid anilide derivatives and a process for preparing thesame |
| GB782971A (en) * | 1952-08-18 | 1957-09-18 | Hoechst Ag | Basically substituted carboxylic acid amides and a process for making them |
| DE1005075B (de) * | 1952-08-18 | 1957-03-28 | Hoechst Ag | Verfahren zur Herstellung von neuen lokalanaesthetisch wirkenden basisch substituierten Carbonsaeureamiden |
| GB726050A (en) * | 1953-10-16 | 1955-03-16 | James Arthur Cooke | A holder for chisels and plane irons whilst honing |
| GB759744A (en) * | 1953-12-24 | 1956-10-24 | Cilag Ltd | Process for the production of mono- and di-substituted amino fatty acid-2-halogeno-6-methyl-anilides |
| GB809286A (en) * | 1954-07-05 | 1959-02-18 | Hoechst Ag | Basically substituted butyric acid anilides and process for their manufacture |
| CH329572A (de) * | 1954-07-29 | 1958-04-30 | Cilag Ag | Verfahren zur Herstellung basischer Amide |
| CH306793A (de) * | 1955-04-30 | 1955-04-30 | Cilag Ag | Verfahren zur Herstellung eines neuen Salzes. |
| US2948736A (en) * | 1957-08-05 | 1960-08-09 | Cilag Chemie | New anilides and process for their production |
| BE601542A (fr) * | 1960-03-23 | |||
| NL6704169A (fr) * | 1966-04-06 | 1967-10-09 | ||
| GB1187118A (en) * | 1967-07-06 | 1970-04-08 | Shell Int Research | Electrodeposition of Synthetic Resin Coatings |
| GB1307250A (en) * | 1970-06-16 | 1973-02-14 | May & Baker Ltd | Benzene derivatives |
| SE410732B (sv) * | 1971-12-13 | 1979-10-29 | Sumitomo Chemical Co | Analogiforfarande for framstellning av anilidderivat med terapeutisk verkan |
| CS195321B2 (en) * | 1975-12-23 | 1980-01-31 | Ciba Geigy Ag | Plant growth suppressing agents |
| GB1514151A (en) * | 1977-01-24 | 1978-06-14 | Gallardo Antonio Sa | Piperidine derivatives |
-
1982
- 1982-08-27 CH CH5116/82A patent/CH650768A5/de not_active IP Right Cessation
-
1983
- 1983-08-01 DE DE19833328186 patent/DE3328186A1/de not_active Withdrawn
- 1983-08-15 GB GB08321953A patent/GB2129424B/en not_active Expired
- 1983-08-17 SE SE8304456A patent/SE8304456L/xx not_active Application Discontinuation
- 1983-08-26 FR FR838313761A patent/FR2532306B1/fr not_active Expired
- 1983-08-26 CA CA000435457A patent/CA1214776A/fr not_active Expired
- 1983-08-26 IT IT48886/83A patent/IT1168212B/it active
- 1983-08-27 JP JP58157050A patent/JPS59130250A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB2129424B (en) | 1986-07-09 |
| DE3328186A1 (de) | 1984-03-01 |
| GB2129424A (en) | 1984-05-16 |
| SE8304456L (sv) | 1984-02-28 |
| SE8304456D0 (sv) | 1983-08-17 |
| FR2532306B1 (fr) | 1989-03-10 |
| GB8321953D0 (en) | 1983-09-14 |
| IT1168212B (it) | 1987-05-20 |
| CA1214776A (fr) | 1986-12-02 |
| IT8348886A0 (it) | 1983-08-26 |
| JPS59130250A (ja) | 1984-07-26 |
| FR2532306A1 (fr) | 1984-03-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |