FI79297C - Foerfarande foer framstaellning av farmakologiskt aktiva benzamidderivat. - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiva benzamidderivat. Download PDFInfo
- Publication number
- FI79297C FI79297C FI840734A FI840734A FI79297C FI 79297 C FI79297 C FI 79297C FI 840734 A FI840734 A FI 840734A FI 840734 A FI840734 A FI 840734A FI 79297 C FI79297 C FI 79297C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- compound
- acid
- iii
- aminoethyl
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 14
- 238000002360 preparation method Methods 0.000 title claims description 11
- 150000003936 benzamides Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 49
- 239000002253 acid Substances 0.000 claims description 22
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 16
- -1 methylenedioxy group Chemical group 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000000460 chlorine Substances 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000007858 starting material Substances 0.000 claims description 6
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 150000001408 amides Chemical class 0.000 claims description 4
- 229910021529 ammonia Inorganic materials 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- ZUTHWPYPIXUPDI-UHFFFAOYSA-N benzyl N-(1,3-dioxoisoindol-4-yl)carbamate Chemical compound O=C(Nc1cccc2C(=O)NC(=O)c12)OCc1ccccc1 ZUTHWPYPIXUPDI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- MALIONKMKPITBV-UHFFFAOYSA-N 2-(3-chloro-4-hydroxyphenyl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)CC1=CC=C(O)C(Cl)=C1 MALIONKMKPITBV-UHFFFAOYSA-N 0.000 claims 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 102000010909 Monoamine Oxidase Human genes 0.000 description 7
- 108010062431 Monoamine oxidase Proteins 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000000155 melt Substances 0.000 description 7
- 239000008346 aqueous phase Substances 0.000 description 6
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012458 free base Substances 0.000 description 5
- GBARCMIFTACERW-UHFFFAOYSA-N n-(2-aminoethyl)-p-chlorobenzamide Chemical compound OCCNC(=O)C1=CC=C(Cl)C=C1 GBARCMIFTACERW-UHFFFAOYSA-N 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000001828 Gelatine Substances 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229920000159 gelatin Polymers 0.000 description 4
- 235000019322 gelatine Nutrition 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- ARUMZUNJBHSOQQ-UHFFFAOYSA-N 2-[(4-chlorobenzoyl)amino]ethylazanium;chloride Chemical compound Cl.NCCNC(=O)C1=CC=C(Cl)C=C1 ARUMZUNJBHSOQQ-UHFFFAOYSA-N 0.000 description 3
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 3
- 208000018737 Parkinson disease Diseases 0.000 description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000003001 depressive effect Effects 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- QGAYWUBUAABRKY-UHFFFAOYSA-N n-(2-aminoethyl)-2,4-dichlorobenzamide Chemical compound NCCNC(=O)C1=CC=C(Cl)C=C1Cl QGAYWUBUAABRKY-UHFFFAOYSA-N 0.000 description 3
- BVSYYNFOBNEAHX-UHFFFAOYSA-N n-(2-aminoethyl)-3,4-dichlorobenzamide Chemical compound NCCNC(=O)C1=CC=C(Cl)C(Cl)=C1 BVSYYNFOBNEAHX-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000011975 tartaric acid Substances 0.000 description 3
- 235000002906 tartaric acid Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ATCRIUVQKHMXSH-UHFFFAOYSA-N 2,4-dichlorobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1Cl ATCRIUVQKHMXSH-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- AGSAITDBACWAIH-UHFFFAOYSA-N 4-chloro-n-[2-[(4-chlorobenzoyl)amino]ethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCCNC(=O)C1=CC=C(Cl)C=C1 AGSAITDBACWAIH-UHFFFAOYSA-N 0.000 description 2
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- AIHKMGLJGLKLSI-UHFFFAOYSA-N N-(2-aminoethyl)-4-chlorobenzamide Chemical compound NCCNC(=O)C1=CC=C(Cl)C=C1 AIHKMGLJGLKLSI-UHFFFAOYSA-N 0.000 description 2
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
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- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 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
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- RWBYCMPOFNRISR-UHFFFAOYSA-N ethyl 4-chlorobenzoate Chemical compound CCOC(=O)C1=CC=C(Cl)C=C1 RWBYCMPOFNRISR-UHFFFAOYSA-N 0.000 description 2
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- 150000004820 halides Chemical class 0.000 description 2
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
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- 235000010755 mineral Nutrition 0.000 description 2
- OTSNCERWNGFUEG-UHFFFAOYSA-N n-(2-aminoethyl)-4-fluorobenzamide Chemical compound NCCNC(=O)C1=CC=C(F)C=C1 OTSNCERWNGFUEG-UHFFFAOYSA-N 0.000 description 2
- ZKSYUNLBFSOENV-UHFFFAOYSA-N n-(2-hydroxyethyl)benzamide Chemical compound OCCNC(=O)C1=CC=CC=C1 ZKSYUNLBFSOENV-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 2
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- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
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- XRKIHUXCUIFHAS-UHFFFAOYSA-N [4-(3-methoxy-3-oxopropyl)phenyl]boronic acid Chemical compound COC(=O)CCC1=CC=C(B(O)O)C=C1 XRKIHUXCUIFHAS-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- 238000007098 aminolysis reaction Methods 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 229940054066 benzamide antipsychotics Drugs 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- VRJSPTBHYIWFEV-UHFFFAOYSA-N carbonochloridic acid ethyl acetate Chemical compound C(C)(=O)OCC.C(O)(=O)Cl VRJSPTBHYIWFEV-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 239000004312 hexamethylene tetramine Substances 0.000 description 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 230000000147 hypnotic effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- QCHGUEIECOASJU-UHFFFAOYSA-N methyl 1,3-benzodioxole-5-carboxylate Chemical compound COC(=O)C1=CC=C2OCOC2=C1 QCHGUEIECOASJU-UHFFFAOYSA-N 0.000 description 1
- CZNGTXVOZOWWKM-UHFFFAOYSA-N methyl 4-bromobenzoate Chemical compound COC(=O)C1=CC=C(Br)C=C1 CZNGTXVOZOWWKM-UHFFFAOYSA-N 0.000 description 1
- MSEBQGULDWDIRW-UHFFFAOYSA-N methyl 4-fluorobenzoate Chemical compound COC(=O)C1=CC=C(F)C=C1 MSEBQGULDWDIRW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- HRKSQNAYPHEBQO-UHFFFAOYSA-N n-(2-acetamidoethyl)-4-chlorobenzamide Chemical compound CC(=O)NCCNC(=O)C1=CC=C(Cl)C=C1 HRKSQNAYPHEBQO-UHFFFAOYSA-N 0.000 description 1
- WJOIKYGQPWYFRI-UHFFFAOYSA-N n-(2-aminoethyl)-1,3-benzodioxole-5-carboxamide Chemical compound NCCNC(=O)C1=CC=C2OCOC2=C1 WJOIKYGQPWYFRI-UHFFFAOYSA-N 0.000 description 1
- CRPCNDLGQJSKQD-UHFFFAOYSA-N n-(2-aminoethyl)-2,4-dichlorobenzamide;hydrochloride Chemical compound Cl.NCCNC(=O)C1=CC=C(Cl)C=C1Cl CRPCNDLGQJSKQD-UHFFFAOYSA-N 0.000 description 1
- NAZZZOYVGVVJEB-UHFFFAOYSA-N n-(2-aminoethyl)-4-bromobenzamide Chemical compound NCCNC(=O)C1=CC=C(Br)C=C1 NAZZZOYVGVVJEB-UHFFFAOYSA-N 0.000 description 1
- SOXPGUJSBKPZMV-UHFFFAOYSA-N n-(2-aminoethyl)-4-bromobenzamide;hydrochloride Chemical compound Cl.NCCNC(=O)C1=CC=C(Br)C=C1 SOXPGUJSBKPZMV-UHFFFAOYSA-N 0.000 description 1
- TYICFMRRICBNNF-UHFFFAOYSA-N n-(2-aminoethyl)-4-cyanobenzamide Chemical compound NCCNC(=O)C1=CC=C(C#N)C=C1 TYICFMRRICBNNF-UHFFFAOYSA-N 0.000 description 1
- RYEDBWKZIZOALG-UHFFFAOYSA-N n-(2-aminoethyl)-4-cyanobenzamide;hydrochloride Chemical compound Cl.NCCNC(=O)C1=CC=C(C#N)C=C1 RYEDBWKZIZOALG-UHFFFAOYSA-N 0.000 description 1
- DAKZISABEDGGSV-UHFFFAOYSA-N n-(2-aminoethyl)acetamide Chemical compound CC(=O)NCCN DAKZISABEDGGSV-UHFFFAOYSA-N 0.000 description 1
- NHWKHNPRDPAXLM-UHFFFAOYSA-N n-(2-aminoethyl)benzamide Chemical class NCCNC(=O)C1=CC=CC=C1 NHWKHNPRDPAXLM-UHFFFAOYSA-N 0.000 description 1
- FYQJUYCGPLFWQR-UHFFFAOYSA-N n-(2-chloroethyl)benzamide Chemical compound ClCCNC(=O)C1=CC=CC=C1 FYQJUYCGPLFWQR-UHFFFAOYSA-N 0.000 description 1
- PPKGFSZXBXLTQX-UHFFFAOYSA-N n-(2-methylsulfonylethyl)benzamide Chemical compound CS(=O)(=O)CCNC(=O)C1=CC=CC=C1 PPKGFSZXBXLTQX-UHFFFAOYSA-N 0.000 description 1
- JCDIVGGDJCLJAR-UHFFFAOYSA-N n-[2-(4-methylphenyl)sulfonylethyl]benzamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CCNC(=O)C1=CC=CC=C1 JCDIVGGDJCLJAR-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 229940117803 phenethylamine Drugs 0.000 description 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical compound OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- AOCSUUGBCMTKJH-UHFFFAOYSA-N tert-butyl n-(2-aminoethyl)carbamate Chemical compound CC(C)(C)OC(=O)NCCN AOCSUUGBCMTKJH-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 229960003732 tyramine Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/77—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/16—Agglomerates; Granulates; Microbeadlets ; Microspheres; Pellets; Solid products obtained by spray drying, spray freeze drying, spray congealing,(multiple) emulsion solvent evaporation or extraction
- A61K9/1605—Excipients; Inactive ingredients
- A61K9/1617—Organic compounds, e.g. phospholipids, fats
- A61K9/1623—Sugars or sugar alcohols, e.g. lactose; Derivatives thereof; Homeopathic globules
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/20—Pills, tablets, discs, rods
- A61K9/2004—Excipients; Inactive ingredients
- A61K9/2013—Organic compounds, e.g. phospholipids, fats
- A61K9/2018—Sugars, or sugar alcohols, e.g. lactose, mannitol; Derivatives thereof, e.g. polysorbates
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
- A61K9/4841—Filling excipients; Inactive ingredients
- A61K9/4858—Organic compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH115083 | 1983-03-03 | ||
| CH1150/83A CH653670A5 (de) | 1983-03-03 | 1983-03-03 | Benzamid-derivate. |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| FI840734A0 FI840734A0 (fi) | 1984-02-22 |
| FI840734L FI840734L (fi) | 1984-09-04 |
| FI79297B FI79297B (fi) | 1989-08-31 |
| FI79297C true FI79297C (fi) | 1989-12-11 |
Family
ID=4203649
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI840734A FI79297C (fi) | 1983-03-03 | 1984-02-22 | Foerfarande foer framstaellning av farmakologiskt aktiva benzamidderivat. |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS59167552A (en, 2012) |
| KR (1) | KR910008202B1 (en, 2012) |
| AR (1) | AR243155A1 (en, 2012) |
| AT (1) | AT390948B (en, 2012) |
| AU (2) | AU570431B2 (en, 2012) |
| BE (1) | BE899059A (en, 2012) |
| CA (1) | CA1252794A (en, 2012) |
| CH (1) | CH653670A5 (en, 2012) |
| DE (1) | DE3407654C2 (en, 2012) |
| DK (1) | DK166382C (en, 2012) |
| ES (3) | ES530230A0 (en, 2012) |
| FI (1) | FI79297C (en, 2012) |
| FR (1) | FR2541996B1 (en, 2012) |
| GB (1) | GB2135998B (en, 2012) |
| GR (1) | GR81866B (en, 2012) |
| HU (1) | HU193556B (en, 2012) |
| IE (1) | IE57004B1 (en, 2012) |
| IL (1) | IL71078A (en, 2012) |
| IT (1) | IT1173365B (en, 2012) |
| LU (1) | LU85231A1 (en, 2012) |
| MC (1) | MC1568A1 (en, 2012) |
| NL (1) | NL8400459A (en, 2012) |
| NO (1) | NO165999C (en, 2012) |
| NZ (1) | NZ207272A (en, 2012) |
| PH (1) | PH19623A (en, 2012) |
| PT (1) | PT78187B (en, 2012) |
| SE (1) | SE466447B (en, 2012) |
| ZA (1) | ZA841394B (en, 2012) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1261335A (en) * | 1984-08-29 | 1989-09-26 | Hoffmann-La Roche Limited/Hoffmann-La Roche Limitee | Ethylenediamine monoamide derivatives |
| US4772630A (en) * | 1984-11-23 | 1988-09-20 | Ciba-Geigy Corp. | Benzamides and their salts |
| NZ219974A (en) * | 1986-04-22 | 1989-08-29 | Goedecke Ag | N-(2'-aminophenyl)-benzamide derivatives, process for their preparation and their use in the control of neoplastic diseases |
| FR2642972B1 (fr) * | 1989-02-14 | 1994-08-05 | Inst Nat Sante Rech Med | Agents pour le diagnostic et le traitement des melanomes, derives halogenes aromatiques utilisables comme de tels agents et leur preparation |
| WO2014155184A1 (en) * | 2013-03-28 | 2014-10-02 | Rhenovia Pharma | Treatment for parkinson's disease |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3342679A (en) * | 1967-09-19 | Parts by weight of acid chloride to react with parts of amine in | ||
| FR6557M (en, 2012) * | 1967-06-20 | 1968-12-23 | Ile De France | |
| GB1455116A (en) * | 1972-12-15 | 1976-11-10 | Ici Ltd | Pharmaceutical compositions |
| GB1520584A (en) * | 1975-04-02 | 1978-08-09 | Yamanouchi Pharma Co Ltd | 2 - alkoxy - 5 substituted benzamide derivatives and their use in pharmaceutical compositions |
| DE2616486A1 (de) * | 1976-04-14 | 1977-11-03 | Basf Ag | Farbstoffe der perylentetracarbonsaeurediimidreihe |
| CA1206964A (en) * | 1980-11-12 | 1986-07-02 | Nobuo Shinma | Tetra-substituted benzene derivatives |
| DE3200258A1 (de) * | 1982-01-07 | 1983-07-21 | Lentia GmbH Chem. u. pharm. Erzeugnisse - Industriebedarf, 8000 München | Substituierte 1-benzoyl-2-phenylimino-imidazolidine, deren saeureadditionssalze, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| IL69997A0 (en) * | 1983-01-03 | 1984-01-31 | Miles Lab | Procainamide and n-acetylprocainamide immunogens,antibodies prepared therefrom,labeled conjugates,and the use of such antibodies and labeled conjugates in immunoassays |
| US4808624A (en) * | 1984-06-28 | 1989-02-28 | Bristol-Myers Company | Pharmacologically active substituted benzamides |
-
1983
- 1983-03-03 CH CH1150/83A patent/CH653670A5/de not_active IP Right Cessation
-
1984
- 1984-01-13 CA CA000445296A patent/CA1252794A/en not_active Expired
- 1984-02-13 NL NL8400459A patent/NL8400459A/nl not_active Application Discontinuation
- 1984-02-22 FI FI840734A patent/FI79297C/fi not_active IP Right Cessation
- 1984-02-23 IT IT19778/84A patent/IT1173365B/it active
- 1984-02-24 NZ NZ207272A patent/NZ207272A/en unknown
- 1984-02-24 ZA ZA841394A patent/ZA841394B/xx unknown
- 1984-02-27 HU HU84767A patent/HU193556B/hu not_active IP Right Cessation
- 1984-02-27 IL IL71078A patent/IL71078A/xx not_active IP Right Cessation
- 1984-02-27 AU AU25066/84A patent/AU570431B2/en not_active Ceased
- 1984-02-29 DK DK147584A patent/DK166382C/da not_active IP Right Cessation
- 1984-02-29 LU LU85231A patent/LU85231A1/de unknown
- 1984-02-29 PH PH30315A patent/PH19623A/en unknown
- 1984-03-01 JP JP59037410A patent/JPS59167552A/ja active Granted
- 1984-03-01 MC MC841696A patent/MC1568A1/xx unknown
- 1984-03-01 DE DE3407654A patent/DE3407654C2/de not_active Expired - Fee Related
- 1984-03-01 GR GR73975A patent/GR81866B/el unknown
- 1984-03-01 FR FR8403219A patent/FR2541996B1/fr not_active Expired
- 1984-03-02 AR AR84295901A patent/AR243155A1/es active
- 1984-03-02 NO NO840797A patent/NO165999C/no unknown
- 1984-03-02 SE SE8401190A patent/SE466447B/sv not_active IP Right Cessation
- 1984-03-02 GB GB08405486A patent/GB2135998B/en not_active Expired
- 1984-03-02 IE IE512/84A patent/IE57004B1/en not_active IP Right Cessation
- 1984-03-02 BE BE0/212488A patent/BE899059A/fr not_active IP Right Cessation
- 1984-03-02 ES ES530230A patent/ES530230A0/es active Granted
- 1984-03-02 AT AT0072484A patent/AT390948B/de not_active IP Right Cessation
- 1984-03-02 PT PT78187A patent/PT78187B/pt not_active IP Right Cessation
- 1984-03-03 KR KR1019840001083A patent/KR910008202B1/ko not_active Expired
- 1984-10-25 ES ES537045A patent/ES8506600A1/es not_active Expired
- 1984-10-25 ES ES537046A patent/ES537046A0/es active Granted
-
1987
- 1987-12-24 AU AU83079/87A patent/AU609758B2/en not_active Ceased
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Owner name: F. HOFFMANN-LA ROCHE AG |