JPS6221343B2 - - Google Patents
Info
- Publication number
- JPS6221343B2 JPS6221343B2 JP57149025A JP14902582A JPS6221343B2 JP S6221343 B2 JPS6221343 B2 JP S6221343B2 JP 57149025 A JP57149025 A JP 57149025A JP 14902582 A JP14902582 A JP 14902582A JP S6221343 B2 JPS6221343 B2 JP S6221343B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- mono
- dimethoxylated
- amine
- solution
- 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
- 150000001875 compounds Chemical class 0.000 claims description 26
- 150000003839 salts Chemical class 0.000 claims description 24
- 239000011541 reaction mixture Substances 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 14
- -1 secondary amine compound Chemical class 0.000 claims description 12
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 claims description 11
- WUAXWQRULBZETB-UHFFFAOYSA-N homoveratric acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC WUAXWQRULBZETB-UHFFFAOYSA-N 0.000 claims description 8
- 230000002829 reductive effect Effects 0.000 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical class CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical class NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 claims description 3
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical class CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 claims description 3
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical class CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 claims description 3
- 150000007925 phenylethylamine derivatives Chemical class 0.000 claims description 3
- WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical class O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 18
- 150000001412 amines Chemical class 0.000 description 17
- 239000007795 chemical reaction product Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 14
- 150000003335 secondary amines Chemical class 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 12
- 238000006722 reduction reaction Methods 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 10
- 230000000747 cardiac effect Effects 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 8
- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 7
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 229960002748 norepinephrine Drugs 0.000 description 7
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000001408 amides Chemical class 0.000 description 6
- 229910000085 borane Inorganic materials 0.000 description 6
- 239000003610 charcoal Substances 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000000921 elemental analysis Methods 0.000 description 5
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 5
- 229940039009 isoproterenol Drugs 0.000 description 5
- 230000004118 muscle contraction Effects 0.000 description 5
- 229940117803 phenethylamine Drugs 0.000 description 5
- 238000005932 reductive alkylation reaction Methods 0.000 description 5
- 230000035939 shock Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 206010003119 arrhythmia Diseases 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- 230000002861 ventricular Effects 0.000 description 4
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical class COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
- 229910000564 Raney nickel Inorganic materials 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- 230000017531 blood circulation Effects 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 210000003205 muscle Anatomy 0.000 description 3
- 210000000056 organ Anatomy 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- HIRLSMKURCRARB-UHFFFAOYSA-N 1-(4-methoxyphenyl)but-2-en-1-one Chemical compound COC1=CC=C(C(=O)C=CC)C=C1 HIRLSMKURCRARB-UHFFFAOYSA-N 0.000 description 2
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VYWQTJWGWLKBQA-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;chloride Chemical compound Cl.NC(N)=O VYWQTJWGWLKBQA-UHFFFAOYSA-N 0.000 description 2
- KSRGADMGIRTXAF-UHFFFAOYSA-N a-Methyldopamine Chemical class CC(N)CC1=CC=C(O)C(O)=C1 KSRGADMGIRTXAF-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229960003638 dopamine Drugs 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000001939 inductive effect Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 210000004165 myocardium Anatomy 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 210000002027 skeletal muscle Anatomy 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 229960001367 tartaric acid Drugs 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- WRRZKDVBPZBNJN-ONEGZZNKSA-N (e)-4-(4-methoxyphenyl)but-3-en-2-one Chemical compound COC1=CC=C(\C=C\C(C)=O)C=C1 WRRZKDVBPZBNJN-ONEGZZNKSA-N 0.000 description 1
- AASYBPPOAOIQPL-UHFFFAOYSA-N 1-(2-bromopropyl)-3-methoxybenzene Chemical compound COC1=CC=CC(CC(C)Br)=C1 AASYBPPOAOIQPL-UHFFFAOYSA-N 0.000 description 1
- YSAXSWPDOFHENC-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]ethanamine Chemical compound C1=C(OC)C(OC)=CC=C1CCNCCC1=CC=C(OC)C(OC)=C1 YSAXSWPDOFHENC-UHFFFAOYSA-N 0.000 description 1
- PMKQAJYOSZNVAA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(3,4-dimethoxyphenyl)ethyl]ethanamine;hydrochloride Chemical compound [Cl-].C1=C(OC)C(OC)=CC=C1CC[NH2+]CCC1=CC=C(OC)C(OC)=C1 PMKQAJYOSZNVAA-UHFFFAOYSA-N 0.000 description 1
- YSOHJBZHRAHOGY-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-[2-(4-methoxyphenyl)butan-2-yl]acetamide Chemical compound C=1C=C(OC)C=CC=1C(C)(CC)NC(=O)CC1=CC=C(OC)C(OC)=C1 YSOHJBZHRAHOGY-UHFFFAOYSA-N 0.000 description 1
- LGDHZCLREKIGKJ-UHFFFAOYSA-N 3,4-dimethoxyaniline Chemical compound COC1=CC=C(N)C=C1OC LGDHZCLREKIGKJ-UHFFFAOYSA-N 0.000 description 1
- MQPDJPHJUHRPAZ-UHFFFAOYSA-N 3-[2-(3,4-dimethoxyphenyl)ethylamino]-1-(4-methoxyphenyl)butan-1-one Chemical compound C1=CC(OC)=CC=C1C(=O)CC(C)NCCC1=CC=C(OC)C(OC)=C1 MQPDJPHJUHRPAZ-UHFFFAOYSA-N 0.000 description 1
- LTAGXVMHLFYRNK-UHFFFAOYSA-N 4-(2-bromoethyl)-1,2-dimethoxybenzene Chemical compound COC1=CC=C(CCBr)C=C1OC LTAGXVMHLFYRNK-UHFFFAOYSA-N 0.000 description 1
- JMHAKVPFYWWNOW-UHFFFAOYSA-N 4-(4-methoxyphenyl)butan-2-amine Chemical compound COC1=CC=C(CCC(C)N)C=C1 JMHAKVPFYWWNOW-UHFFFAOYSA-N 0.000 description 1
- SDTHIDMOBRXVOQ-UHFFFAOYSA-N 5-[bis(2-chloroethyl)amino]-6-methyl-1h-pyrimidine-2,4-dione Chemical compound CC=1NC(=O)NC(=O)C=1N(CCCl)CCCl SDTHIDMOBRXVOQ-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical group OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- WDOZNWXGJADJAJ-UHFFFAOYSA-N N-[2-(3,4-dimethoxyphenyl)ethyl]-3-(3-methoxyphenyl)propan-1-amine hydrochloride Chemical compound Cl.COC1=CC=CC(CCCNCCC=2C=C(OC)C(OC)=CC=2)=C1 WDOZNWXGJADJAJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000000150 Sympathomimetic Substances 0.000 description 1
- 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 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- WVHBHPATSLQXGC-UHFFFAOYSA-N benzene;ethanol Chemical compound CCO.C1=CC=CC=C1 WVHBHPATSLQXGC-UHFFFAOYSA-N 0.000 description 1
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical class CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 208000035850 clinical syndrome Diseases 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005661 deetherification reaction Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XQBYLOYJNLQCLU-UHFFFAOYSA-N hepta-2,5-dien-4-one Chemical compound CC=CC(=O)C=CC XQBYLOYJNLQCLU-UHFFFAOYSA-N 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000036543 hypotension Effects 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000002107 myocardial effect Effects 0.000 description 1
- FRJMDYSVLCJWQC-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-4-(4-methoxyphenyl)butan-2-amine Chemical compound C1=CC(OC)=CC=C1CCC(C)NCCC1=CC=C(OC)C(OC)=C1 FRJMDYSVLCJWQC-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- WSDQIHATCCOMLH-UHFFFAOYSA-N phenyl n-(3,5-dichlorophenyl)carbamate Chemical class ClC1=CC(Cl)=CC(NC(=O)OC=2C=CC=CC=2)=C1 WSDQIHATCCOMLH-UHFFFAOYSA-N 0.000 description 1
- 150000005334 phenylbutanes Chemical class 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940127230 sympathomimetic drug Drugs 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 229940064707 sympathomimetics Drugs 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- WCJYTPVNMWIZCG-UHFFFAOYSA-N xylylcarb Chemical compound CNC(=O)OC1=CC=C(C)C(C)=C1 WCJYTPVNMWIZCG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- 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
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
-
- 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
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24346672A | 1972-04-12 | 1972-04-12 | |
| US243466 | 1972-04-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS58131945A JPS58131945A (ja) | 1983-08-06 |
| JPS6221343B2 true JPS6221343B2 (US07223432-20070529-C00017.png) | 1987-05-12 |
Family
ID=22918877
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48041750A Expired JPS5825656B2 (ja) | 1972-04-12 | 1973-04-12 | ドパミンユウドウタイ ノ セイゾウホウ |
| JP57149025A Granted JPS58131945A (ja) | 1972-04-12 | 1982-08-27 | 第二アミン化合物およびその塩の製造方法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP48041750A Expired JPS5825656B2 (ja) | 1972-04-12 | 1973-04-12 | ドパミンユウドウタイ ノ セイゾウホウ |
Country Status (31)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH585693A5 (US07223432-20070529-C00017.png) * | 1974-02-08 | 1977-03-15 | Ciba Geigy Ag | |
| US4342692A (en) * | 1980-10-20 | 1982-08-03 | Usv Pharmaceutical Corporation | Pyrrolidines |
| EP0071399A3 (en) * | 1981-07-22 | 1983-12-07 | Syntex (U.S.A.) Inc. | Substituted pyrrolidine cardiovascular system regulators and antihypertensives, their preparation and use |
| JPS6061523A (ja) * | 1983-09-16 | 1985-04-09 | Shionogi & Co Ltd | 経口用ドブタミン製剤 |
| ZA881076B (en) * | 1987-02-24 | 1989-10-25 | Lilly Co Eli | Dobutamine salts |
| JPH0383364U (US07223432-20070529-C00017.png) * | 1989-12-18 | 1991-08-23 | ||
| CA2103367A1 (en) * | 1991-05-20 | 1992-11-21 | Akihide Koda | Phellodendrine analogs and allergy type iv suppressor containing the same as active ingredient |
| EP0620208B1 (en) * | 1993-04-13 | 1997-07-09 | Duphar International Research B.V | Production of dobutamine compounds |
| DE69404063T2 (de) * | 1993-04-13 | 1998-01-22 | Duphar Int Res | Herstellung von Dobutamin Verbindungen |
| EP1546088B1 (en) | 2002-10-03 | 2014-12-17 | Novaremed Ltd. | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| JP4939396B2 (ja) * | 2004-03-26 | 2012-05-23 | ノヴァレメッド リミテッド | Ａｉｄｓ及び他のウイルス性疾患及びｈｉｖ関連感染症の改善又はその治療用化合物及びそのような化合物を含む組成物、そのような疾患及び感染症の治療方法及びそのような化合物及び組成物の製造方法 |
| GB0804213D0 (en) | 2008-03-06 | 2008-04-16 | New Era Biotech Ltd | A method of printing or preventing pain |
| SG178191A1 (en) | 2009-07-31 | 2012-03-29 | Cognition Therapeutics Inc | Inhibitors of cognitive decline |
| US8802734B2 (en) | 2009-09-09 | 2014-08-12 | Novaremed Limited | Method of treating or preventing pain |
| CA2846604A1 (en) * | 2011-08-25 | 2013-02-28 | Cognition Therapeutics, Inc. | Compositions and methods for treating neurodegenerative disease |
| ES2915833T3 (es) | 2014-01-31 | 2022-06-27 | Cognition Therapeutics Inc | Composiciones de isoindolina y métodos para tratar una enfermedad neurodegenerativa y una degeneración macular |
| CA3061787A1 (en) | 2017-05-15 | 2018-11-22 | Cognition Therapeutics, Inc. | Compositions for treating neurodegenerative diseases |
| CN114524734B (zh) * | 2021-12-27 | 2024-04-26 | 嘉实（湖南）医药科技有限公司 | 一种盐酸多巴酚丁胺的制备方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2276619A (en) * | 1942-03-17 | N-phentlaliphatic-dihtoroxyphentnl |
-
1973
- 1973-03-28 ZA ZA732136A patent/ZA732136B/xx unknown
- 1973-04-09 CY CY963A patent/CY963A/xx unknown
- 1973-04-09 DE DE2317710A patent/DE2317710C2/de not_active Expired
- 1973-04-09 GB GB1683573A patent/GB1392674A/en not_active Expired
- 1973-04-10 IE IE563/73A patent/IE37511B1/xx unknown
- 1973-04-10 FR FR7312845A patent/FR2182947B1/fr not_active Expired
- 1973-04-10 SE SE7305032A patent/SE399064B/xx unknown
- 1973-04-11 AT AT318773A patent/AT323719B/de not_active IP Right Cessation
- 1973-04-11 DK DK196773A patent/DK142750C/da not_active IP Right Cessation
- 1973-04-11 CH CH1112475A patent/CH580563A5/xx not_active IP Right Cessation
- 1973-04-11 YU YU00976/73A patent/YU36483B/xx unknown
- 1973-04-11 KR KR7300573A patent/KR790000113B1/ko active
- 1973-04-11 SU SU1908277A patent/SU496719A3/ru active
- 1973-04-11 AU AU54385/73A patent/AU472734B2/en not_active Expired
- 1973-04-11 BG BG26268A patent/BG23001A3/xx unknown
- 1973-04-11 BE BE1004956A patent/BE798051A/xx not_active IP Right Cessation
- 1973-04-11 NL NLAANVRAGE7305097,A patent/NL174459C/xx not_active IP Right Cessation
- 1973-04-11 CA CA168,428A patent/CA1018188A/en not_active Expired
- 1973-04-11 CH CH517473A patent/CH569691A5/xx not_active IP Right Cessation
- 1973-04-12 RO RO7374457A patent/RO65105A/ro unknown
- 1973-04-12 PL PL1973161874A patent/PL90695B1/pl unknown
- 1973-04-12 DD DD73170118A patent/DD107670B3/de unknown
- 1973-04-12 PL PL1973183808A patent/PL94207B1/pl unknown
- 1973-04-12 PH PH14508A patent/PH11041A/en unknown
- 1973-04-12 HU HUEI552A patent/HU167597B/hu unknown
- 1973-04-12 CS CS732601A patent/CS190406B2/cs unknown
- 1973-04-12 AR AR247523A patent/AR203822A1/es active
- 1973-04-12 HU HUEI469A patent/HU166213B/hu unknown
- 1973-04-12 CS CS77171A patent/CS190448B2/cs unknown
- 1973-04-12 JP JP48041750A patent/JPS5825656B2/ja not_active Expired
- 1973-04-12 ES ES413639A patent/ES413639A1/es not_active Expired
- 1973-04-12 IL IL42016A patent/IL42016A/en unknown
- 1973-04-12 RO RO7383749A patent/RO70892A/ro unknown
-
1978
- 1978-08-10 KE KE2870A patent/KE2870A/xx unknown
- 1978-09-07 HK HK501/78A patent/HK50178A/xx unknown
- 1978-12-30 MY MY381/78A patent/MY7800381A/xx unknown
-
1979
- 1979-12-28 YU YU3212/79A patent/YU37113B/xx unknown
-
1982
- 1982-08-27 JP JP57149025A patent/JPS58131945A/ja active Granted
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPS6221343B2 (US07223432-20070529-C00017.png) | ||
| US3987200A (en) | Method for increasing cardiac contractility | |
| DE2649605C3 (de) | p-substituierte 1-Phenoxy-3-amino-2-propanole, Verfahren zu ihrer Herstellung und sie enthaltende Arzneimittel | |
| US4313896A (en) | Aryloxyphenylpropylamines | |
| JP2637737B2 (ja) | 新規な薬剤 | |
| US4081447A (en) | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof | |
| US4289787A (en) | Quaternary ammonium antiarrhythmic drugs | |
| JPH02167253A (ja) | フェニルアルキルアミノサリチルアミド及びその製造方法 | |
| PL90026B1 (US07223432-20070529-C00017.png) | ||
| US4460605A (en) | 2-[2'-Hydroxy-3'-(1,1-dimethylpropylamino)-propoxy]-β-phenylpropiophenone, its physiologically acceptable acid addition salts, and pharmaceutical compositions | |
| JPS6326099B2 (US07223432-20070529-C00017.png) | ||
| EP0074903B1 (fr) | Dérivés d'amino-2 tétrahydro-1,2,3,4 naphtalène, leur préparation et leur application en thérapeutique | |
| FI65425C (fi) | Foerfarande foer framstaellning av ett terapeutiskt anvaendbart kvaternaert ammoniumsalt av fenylalkylamin | |
| EP0076669A1 (en) | Novel 3-phenyl-1-indanamines, pharmaceutical compositions and methods of preparation | |
| US4490392A (en) | Benzylalcohol derivative and process for preparing | |
| DE2619617C2 (US07223432-20070529-C00017.png) | ||
| RU2032663C1 (ru) | 4-(3-этил-(3-(пропилсульфинил) -пропил)-амино)-2-гидроксипропокси) -бензонитрил в виде стереоизомеров или их фармацевтически приемлемые соли и способ их получения | |
| JPS6360750B2 (US07223432-20070529-C00017.png) | ||
| US3720714A (en) | 2-alkoxy-2(naphthyl)-alkanamidoximes | |
| KR830001683B1 (ko) | 4급 암모늄 부정맥 치료제의 제조방법 | |
| US4395410A (en) | Quaternary ammonium antiarrhythmic drugs | |
| DD153682A1 (de) | Verfahren zur herstellung neuer alkanolamine | |
| FR2653999A1 (fr) | Nouveaux derives de la morpholine, leur procede de preparation et les compositions pharmaceutiques les renfermant. | |
| DK145041B (da) | Analogifremgangsmaade til fremstilling af et benzophenonderivat eller syreadditionssalte deraf | |
| DK142076B (da) | Sekundære 3,4-dimethoxyphenethylamin-forbindelser til anvendelse som mellemprodukter ved fremstilling af dopaminderivater. |
