CA1214776A - Basic acetanilides, a process for their preparation and a pharmacological composition containing these acetanilides - Google Patents
Basic acetanilides, a process for their preparation and a pharmacological composition containing these acetanilidesInfo
- Publication number
- CA1214776A CA1214776A CA000435457A CA435457A CA1214776A CA 1214776 A CA1214776 A CA 1214776A CA 000435457 A CA000435457 A CA 000435457A CA 435457 A CA435457 A CA 435457A CA 1214776 A CA1214776 A CA 1214776A
- Authority
- CA
- Canada
- Prior art keywords
- acetanilide
- methyl
- chloro
- produced
- process according
- 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
- 150000008061 acetanilides Chemical class 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 34
- 230000008569 process Effects 0.000 title claims description 34
- 238000002360 preparation method Methods 0.000 title description 2
- 239000008196 pharmacological composition Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 13
- -1 nitro, amino Chemical group 0.000 claims abstract description 11
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 7
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000004953 trihalomethyl group Chemical group 0.000 claims abstract 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 39
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- 238000001816 cooling Methods 0.000 claims description 13
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 11
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 8
- 229960001413 acetanilide Drugs 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 4
- 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 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- BBQZKZIIRKKRBD-UHFFFAOYSA-N 2-chloro-n-(2-chloro-6-methylphenyl)acetamide Chemical compound CC1=CC=CC(Cl)=C1NC(=O)CCl BBQZKZIIRKKRBD-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 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 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000008064 anhydrides Chemical group 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- 150000002367 halogens Chemical group 0.000 claims description 3
- 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 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 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 claims description 2
- 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 claims description 2
- 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 claims description 2
- BZNNHUKHVZUGGQ-UHFFFAOYSA-N 2-chloro-n-(2-propanoylphenyl)acetamide Chemical compound CCC(=O)C1=CC=CC=C1NC(=O)CCl BZNNHUKHVZUGGQ-UHFFFAOYSA-N 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
- SFLXGLGYWMEIHB-UHFFFAOYSA-N N-(2-methyl-6-propanoylphenyl)-2-pyrrolidin-1-ylacetamide Chemical compound N1(CCCC1)CC(=O)NC1=C(C=CC=C1C(CC)=O)C SFLXGLGYWMEIHB-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 150000002366 halogen compounds Chemical class 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 13
- 238000010992 reflux Methods 0.000 claims 10
- 229940076134 benzene Drugs 0.000 claims 9
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 6
- 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 claims 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 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 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 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 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
- 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 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 206010002091 Anaesthesia Diseases 0.000 abstract description 2
- 238000001949 anaesthesia Methods 0.000 abstract description 2
- 230000037005 anaesthesia Effects 0.000 abstract description 2
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
- 239000003416 antiarrhythmic agent Substances 0.000 abstract description 2
- 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 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- 229960000443 hydrochloric acid Drugs 0.000 description 7
- 235000011167 hydrochloric acid Nutrition 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 238000001035 drying Methods 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000002955 isolation Methods 0.000 description 3
- 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 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
- YDPXZINXUVCZKH-UHFFFAOYSA-N 2-ethoxy-6-methylaniline Chemical compound CCOC1=CC=CC(C)=C1N YDPXZINXUVCZKH-UHFFFAOYSA-N 0.000 description 2
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-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
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 229940039407 aniline Drugs 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000013078 crystal Substances 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
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 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
- LDUCMSVRKKDATH-UHFFFAOYSA-N 2-bromo-6-methylaniline Chemical compound CC1=CC=CC(Br)=C1N LDUCMSVRKKDATH-UHFFFAOYSA-N 0.000 description 1
- FCMRHMPITHLLLA-UHFFFAOYSA-N 2-methyl-6-nitroaniline Chemical compound CC1=CC=CC([N+]([O-])=O)=C1N FCMRHMPITHLLLA-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 229910021589 Copper(I) bromide Inorganic materials 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960001040 ammonium chloride Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 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
- 229960001701 chloroform Drugs 0.000 description 1
- 235000019628 coolness Nutrition 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
- 150000002148 esters Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 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
- 239000011521 glass Substances 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 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
- 239000000463 material Substances 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
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 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
- 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
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000007858 starting material 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
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
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- 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)
Applications Claiming Priority (2)
| 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. |
| CH5116/82-8 | 1982-08-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1214776A true CA1214776A (en) | 1986-12-02 |
Family
ID=4288192
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000435457A Expired CA1214776A (en) | 1982-08-27 | 1983-08-26 | Basic acetanilides, a process for their preparation and a pharmacological composition containing these acetanilides |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS59130250A (xx) |
| CA (1) | CA1214776A (xx) |
| CH (1) | CH650768A5 (xx) |
| DE (1) | DE3328186A1 (xx) |
| FR (1) | FR2532306B1 (xx) |
| GB (1) | GB2129424B (xx) |
| IT (1) | IT1168212B (xx) |
| SE (1) | SE8304456L (xx) |
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 (xx) * | ||||
| GB859355A (xx) * | ||||
| US2689853A (en) * | 1954-09-21 | Certain i | ||
| BE517755A (xx) * | ||||
| NL73080C (xx) * | 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 (xx) * | 1960-03-23 | |||
| NL6704169A (xx) * | 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/en 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 |
| IT8348886A0 (it) | 1983-08-26 |
| CH650768A5 (de) | 1985-08-15 |
| JPS59130250A (ja) | 1984-07-26 |
| FR2532306A1 (fr) | 1984-03-02 |
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| Date | Code | Title | Description |
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| MKEX | Expiry |