NO129903B - - Google Patents
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- NO129903B NO129903B NO01048/70A NO104870A NO129903B NO 129903 B NO129903 B NO 129903B NO 01048/70 A NO01048/70 A NO 01048/70A NO 104870 A NO104870 A NO 104870A NO 129903 B NO129903 B NO 129903B
- Authority
- NO
- Norway
- Prior art keywords
- tert
- butylaminomethyl
- acid
- grams
- bis
- Prior art date
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- WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 69
- -1 1-methyl-cyclopropanecarbonyl Chemical group 0.000 claims description 59
- 239000002253 acid Chemical group 0.000 claims description 40
- 235000019445 benzyl alcohol Nutrition 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 16
- 239000012458 free base Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 229910052727 yttrium Inorganic materials 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 125000001589 carboacyl group Chemical group 0.000 claims description 2
- NKLCHDQGUHMCGL-UHFFFAOYSA-N cyclohexylidenemethanone Chemical group O=C=C1CCCCC1 NKLCHDQGUHMCGL-UHFFFAOYSA-N 0.000 claims description 2
- YZVUSXWBAYOTBX-UHFFFAOYSA-N CC(C)(C)C(=O)OCC1=C(C=CC(=C1)C(C(=O)C(C2=CC(=C(C=C2)OC(=O)C(C)(C)C)COC(=O)C(C)(C)C)NC(C)(C)C)NC(C)(C)C)OC(=O)C(C)(C)C Chemical compound CC(C)(C)C(=O)OCC1=C(C=CC(=C1)C(C(=O)C(C2=CC(=C(C=C2)OC(=O)C(C)(C)C)COC(=O)C(C)(C)C)NC(C)(C)C)NC(C)(C)C)OC(=O)C(C)(C)C YZVUSXWBAYOTBX-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 80
- 238000002844 melting Methods 0.000 description 44
- 230000008018 melting Effects 0.000 description 44
- 239000000243 solution Substances 0.000 description 43
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 239000007787 solid Substances 0.000 description 29
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 19
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 241000282472 Canis lupus familiaris Species 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- 238000012360 testing method Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- 229940124630 bronchodilator Drugs 0.000 description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 8
- JQQYYKZPHGWVCC-UHFFFAOYSA-N 2-(tert-butylamino)-1-(3,4-dihydroxyphenyl)ethanone;hydrochloride Chemical compound Cl.CC(C)(C)NCC(=O)C1=CC=C(O)C(O)=C1 JQQYYKZPHGWVCC-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 7
- 229960004484 carbachol Drugs 0.000 description 7
- AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical compound [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 229940098779 methanesulfonic acid Drugs 0.000 description 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000443 aerosol Substances 0.000 description 6
- 229960001340 histamine Drugs 0.000 description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 6
- 229940011051 isopropyl acetate Drugs 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- 239000000908 ammonium hydroxide Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 5
- 230000007883 bronchodilation Effects 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000011084 recovery Methods 0.000 description 5
- 230000009467 reduction Effects 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 230000001975 sympathomimetic effect Effects 0.000 description 5
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- 206010006482 Bronchospasm Diseases 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 230000002526 effect on cardiovascular system Effects 0.000 description 4
- 239000012259 ether extract Substances 0.000 description 4
- 150000004820 halides Chemical class 0.000 description 4
- 235000011167 hydrochloric acid Nutrition 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 206010062119 Sympathomimetic effect Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229940095564 anhydrous calcium sulfate Drugs 0.000 description 3
- WVYBKVIVGZLWOS-UHFFFAOYSA-N benzyloxidanium;chloride Chemical compound Cl.OCC1=CC=CC=C1 WVYBKVIVGZLWOS-UHFFFAOYSA-N 0.000 description 3
- XZXMWAHILBWKBI-UHFFFAOYSA-N bis(3,4-dihydroxyphenyl)methanone Chemical compound C1=C(O)C(O)=CC=C1C(=O)C1=CC=C(O)C(O)=C1 XZXMWAHILBWKBI-UHFFFAOYSA-N 0.000 description 3
- 230000007885 bronchoconstriction Effects 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
- 238000001704 evaporation Methods 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000001802 infusion Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- DZKNJOTUIRCMMA-UHFFFAOYSA-N 1-[3,4-bis(4-methylphenoxy)phenyl]-2-(tert-butylamino)ethanone;hydrochloride Chemical compound Cl.C1=CC(C)=CC=C1OC1=CC=C(C(=O)CNC(C)(C)C)C=C1OC1=CC=C(C)C=C1 DZKNJOTUIRCMMA-UHFFFAOYSA-N 0.000 description 2
- XYHKNCXZYYTLRG-UHFFFAOYSA-N 1h-imidazole-2-carbaldehyde Chemical compound O=CC1=NC=CN1 XYHKNCXZYYTLRG-UHFFFAOYSA-N 0.000 description 2
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 2
- ISULZYQDGYXDFW-UHFFFAOYSA-N 3-methylbutanoyl chloride Chemical compound CC(C)CC(Cl)=O ISULZYQDGYXDFW-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- YZZJUBCFAXOSSW-UHFFFAOYSA-N CC(C)CC(=O)OCC1=C(C=CC(=C1)C(C(=O)C(C2=CC(=C(C=C2)OC(=O)CC(C)C)COC(=O)CC(C)C)NC(C)(C)C)NC(C)(C)C)OC(=O)CC(C)C Chemical compound CC(C)CC(=O)OCC1=C(C=CC(=C1)C(C(=O)C(C2=CC(=C(C=C2)OC(=O)CC(C)C)COC(=O)CC(C)C)NC(C)(C)C)NC(C)(C)C)OC(=O)CC(C)C YZZJUBCFAXOSSW-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- OQAGVSWESNCJJT-UHFFFAOYSA-N Methyl 3-methylbutanoate Chemical compound COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000150 Sympathomimetic Substances 0.000 description 2
- 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 2
- XJBFCHHXDKQZMP-UHFFFAOYSA-N [4-[2-(tert-butylamino)acetyl]-2-(3,3-dimethylbutanoyloxy)phenyl] 3,3-dimethylbutanoate;hydrochloride Chemical compound Cl.CC(C)(C)CC(=O)OC1=CC=C(C(=O)CNC(C)(C)C)C=C1OC(=O)CC(C)(C)C XJBFCHHXDKQZMP-UHFFFAOYSA-N 0.000 description 2
- RFYBXWBIHNZUEZ-UHFFFAOYSA-N [4-[2-(tert-butylamino)acetyl]-2-hydroxyphenyl] 3-methylbutanoate;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC(C)CC(=O)OC1=CC=C(C(=O)CNC(C)(C)C)C=C1O RFYBXWBIHNZUEZ-UHFFFAOYSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 230000036772 blood pressure Effects 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
- 230000003182 bronchodilatating effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 210000000038 chest Anatomy 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 2
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 230000004936 stimulating effect Effects 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
- AAWZDTNXLSGCEK-LNVDRNJUSA-N (3r,5r)-1,3,4,5-tetrahydroxycyclohexane-1-carboxylic acid Chemical compound O[C@@H]1CC(O)(C(O)=O)C[C@@H](O)C1O AAWZDTNXLSGCEK-LNVDRNJUSA-N 0.000 description 1
- DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-UHFFFAOYSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- KFUONKMBTFJUHV-UHFFFAOYSA-N 1-[3,4-bis(2-methylphenoxy)phenyl]-2-(tert-butylamino)ethanone;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.CC1=CC=CC=C1OC1=CC=C(C(=O)CNC(C)(C)C)C=C1OC1=CC=CC=C1C KFUONKMBTFJUHV-UHFFFAOYSA-N 0.000 description 1
- YPZWWLCFEIXARW-UHFFFAOYSA-N 1-[3,4-bis(2-methylphenoxy)phenyl]-2-(tert-butylamino)ethanone;methanesulfonic acid Chemical compound CS(O)(=O)=O.CC1=CC=CC=C1OC1=CC=C(C(=O)CNC(C)(C)C)C=C1OC1=CC=CC=C1C YPZWWLCFEIXARW-UHFFFAOYSA-N 0.000 description 1
- IUMIJXIFRRTSKZ-UHFFFAOYSA-N 1-[3,4-bis(4-methylphenoxy)phenyl]-2-(tert-butylamino)ethanone;methanesulfonic acid Chemical compound CS(O)(=O)=O.C1=CC(C)=CC=C1OC1=CC=C(C(=O)CNC(C)(C)C)C=C1OC1=CC=C(C)C=C1 IUMIJXIFRRTSKZ-UHFFFAOYSA-N 0.000 description 1
- LAMHAMBOLINJML-UHFFFAOYSA-N 1-[3-(chloromethyl)-4-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=CC=C(O)C(CCl)=C1 LAMHAMBOLINJML-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81237069A | 1969-04-01 | 1969-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129903B true NO129903B (es) | 1974-06-10 |
Family
ID=25209368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01048/70A NO129903B (es) | 1969-04-01 | 1970-03-20 |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS5314544B1 (es) |
| AT (1) | AT300762B (es) |
| BE (1) | BE748178A (es) |
| CH (1) | CH522589A (es) |
| DE (1) | DE2015573C3 (es) |
| DK (1) | DK131459B (es) |
| ES (1) | ES378092A1 (es) |
| FI (1) | FI54796C (es) |
| FR (1) | FR2042295B1 (es) |
| GB (1) | GB1298771A (es) |
| IE (1) | IE34583B1 (es) |
| IL (2) | IL42029A (es) |
| NL (1) | NL171155C (es) |
| NO (1) | NO129903B (es) |
| PH (2) | PH9407A (es) |
| SE (2) | SE381039B (es) |
| ZA (1) | ZA702065B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138581A (en) | 1969-04-01 | 1979-02-06 | Sterling Drugs Inc. | 3(Hydroxy or hydroxymethyl)-4(hydroxy)-α-(aminomethyl)benzyl alcohols |
| US3809714A (en) * | 1972-08-31 | 1974-05-07 | Interx Research Corp | Novel ester of ((methylamino)methyl) benzyl alcohol |
| US3868461A (en) * | 1972-11-22 | 1975-02-25 | Interx Research Corp | Ester of 3,4-dihydroxy-alpha (isopropylamino) methyl benzyl alcohol, composition and anti-asthma use thereof |
| US4046913A (en) | 1973-08-18 | 1977-09-06 | Boehringer Ingelheim Gmbh | 1-(M-alkanoyloxy-phenyl)-1-hydroxy-2-(N-lower alkyl-amino)-ethanes and salts thereof |
| LU71637A1 (es) * | 1974-01-15 | 1975-06-17 | ||
| US4000315A (en) * | 1974-09-09 | 1976-12-28 | Zoecon Corporation | Cyclopropane esters for the control of mites |
| US3957849A (en) * | 1974-09-09 | 1976-05-18 | Zoecon Corporation | Cyclopropane esters |
| CY1273A (en) | 1980-07-09 | 1985-03-08 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives;preparation,compositions and intermediates |
| DE3163114D1 (en) * | 1980-07-09 | 1984-05-17 | Draco Ab | Therapeutically active derivatives of phenylethanol amines |
| FR2541999B1 (fr) * | 1983-03-04 | 1986-09-19 | Bristol Myers Co | Phenethanolamines et leurs utilisations |
| US4614830A (en) * | 1985-08-09 | 1986-09-30 | Sterling Drug Inc. | Esterification process |
| IT1229846B (it) * | 1989-04-20 | 1991-09-13 | Simes | Esteri di catecolammine. |
| US5118683A (en) * | 1990-06-13 | 1992-06-02 | Schering Corporation | Esters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| US5011845A (en) * | 1990-06-13 | 1991-04-30 | Schering Corporation | Cyclic diesters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| WO2010121022A1 (en) | 2009-04-15 | 2010-10-21 | Research Triangle Institute | Monoamine reuptake inhibitors |
| ES2687095T3 (es) | 2010-05-21 | 2018-10-23 | Research Triangle Institute | Fenilimorfolinas y análogos de las mismas |
| ES2546492T3 (es) | 2010-05-21 | 2015-09-24 | Research Triangle Institute | Derivados de 1-fenilmorfolina como análogos de hidroxibupropion para tratar drogodependencia |
| US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| CN108997261B (zh) * | 2017-06-07 | 2022-01-07 | 东莞市凯法生物医药有限公司 | 一类化合物及其制备方法与应用 |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
-
1970
- 1970-03-20 NO NO01048/70A patent/NO129903B/no unknown
- 1970-03-20 GB GB03690/70A patent/GB1298771A/en not_active Expired
- 1970-03-24 IL IL42029A patent/IL42029A/xx unknown
- 1970-03-24 IL IL34148A patent/IL34148A/xx unknown
- 1970-03-25 PH PH11270*UA patent/PH9407A/en unknown
- 1970-03-26 CH CH467070A patent/CH522589A/fr not_active IP Right Cessation
- 1970-03-26 ZA ZA702065A patent/ZA702065B/xx unknown
- 1970-03-27 BE BE748178D patent/BE748178A/xx not_active IP Right Cessation
- 1970-03-31 DK DK160470AA patent/DK131459B/da not_active IP Right Cessation
- 1970-03-31 ES ES378092A patent/ES378092A1/es not_active Expired
- 1970-03-31 SE SE7004367A patent/SE381039B/xx unknown
- 1970-04-01 NL NLAANVRAGE7004671,A patent/NL171155C/xx not_active IP Right Cessation
- 1970-04-01 FI FI908/70A patent/FI54796C/fi active
- 1970-04-01 FR FR707011697A patent/FR2042295B1/fr not_active Expired
- 1970-04-01 DE DE2015573A patent/DE2015573C3/de not_active Expired
- 1970-04-01 IE IE394/70A patent/IE34583B1/xx unknown
- 1970-04-01 JP JP2779370A patent/JPS5314544B1/ja active Pending
- 1970-04-01 AT AT296170A patent/AT300762B/de not_active IP Right Cessation
-
1972
- 1972-07-14 PH PH13731A patent/PH14377A/en unknown
-
1973
- 1973-03-23 SE SE7304162A patent/SE413503B/xx unknown
- 1973-07-31 JP JP8630073A patent/JPS5414096B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2015573A1 (de) | 1970-10-08 |
| ZA702065B (en) | 1971-01-27 |
| DK131459B (da) | 1975-07-21 |
| IE34583L (en) | 1970-10-01 |
| IE34583B1 (en) | 1975-06-25 |
| BE748178A (fr) | 1970-09-28 |
| DK131459C (es) | 1975-12-08 |
| JPS5314544B1 (es) | 1978-05-18 |
| SE413503B (sv) | 1980-06-02 |
| NL171155B (nl) | 1982-09-16 |
| ES378092A1 (es) | 1973-01-01 |
| DE2015573B2 (de) | 1978-03-16 |
| CH522589A (fr) | 1972-06-30 |
| PH14377A (en) | 1981-06-17 |
| FR2042295A1 (es) | 1971-02-12 |
| GB1298771A (en) | 1972-12-06 |
| JPS5414096B1 (es) | 1979-06-05 |
| DE2015573C3 (de) | 1978-11-02 |
| NL171155C (nl) | 1983-02-16 |
| FI54796B (fi) | 1978-11-30 |
| IL34148A0 (en) | 1970-07-19 |
| IL34148A (en) | 1974-01-14 |
| PH9407A (en) | 1975-11-06 |
| IL42029A (en) | 1974-01-14 |
| AT300762B (de) | 1972-08-10 |
| FR2042295B1 (es) | 1974-06-14 |
| SE381039B (sv) | 1975-11-24 |
| FI54796C (fi) | 1979-03-12 |
| NL7004671A (es) | 1970-10-05 |
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