NO135244B - - Google Patents
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- Publication number
- NO135244B NO135244B NO4113/72A NO411372A NO135244B NO 135244 B NO135244 B NO 135244B NO 4113/72 A NO4113/72 A NO 4113/72A NO 411372 A NO411372 A NO 411372A NO 135244 B NO135244 B NO 135244B
- Authority
- NO
- Norway
- Prior art keywords
- propanol
- dimethoxyphenethylamine
- chloro
- product
- acid
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- -1 cyano, hydroxymethyl Chemical group 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000012458 free base Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 34
- 229960004592 isopropanol Drugs 0.000 description 27
- 239000000047 product Substances 0.000 description 20
- 238000002425 crystallisation Methods 0.000 description 19
- 230000008025 crystallization Effects 0.000 description 19
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000747 cardiac effect Effects 0.000 description 5
- 210000002837 heart atrium Anatomy 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- 210000001519 tissue Anatomy 0.000 description 5
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 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
- 238000002156 mixing Methods 0.000 description 3
- 239000001294 propane Substances 0.000 description 3
- 230000035484 reaction time Effects 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
- WYAFQPYCJBLWAS-UHFFFAOYSA-N 2-[(3-methylphenoxy)methyl]oxirane Chemical compound CC1=CC=CC(OCC2OC2)=C1 WYAFQPYCJBLWAS-UHFFFAOYSA-N 0.000 description 2
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LJAWKPRZRRCPFH-UHFFFAOYSA-N COC1(CC(=CC=C1)CCN)OC Chemical compound COC1(CC(=CC=C1)CCN)OC LJAWKPRZRRCPFH-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
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000674 adrenergic antagonist 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
- 239000002876 beta blocker Substances 0.000 description 2
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 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
- 150000002576 ketones Chemical class 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 150000003511 tertiary amides Chemical class 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000003437 trachea Anatomy 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- VKRXNGBHRQVOQV-UHFFFAOYSA-N 1-(3-tert-butylphenoxy)-3-chloropropan-2-ol Chemical compound C(C)(C)(C)C=1C=C(OCC(CCl)O)C=CC1 VKRXNGBHRQVOQV-UHFFFAOYSA-N 0.000 description 1
- OVEPNAHYQINONH-UHFFFAOYSA-N 1-[2-(3-chloro-2-hydroxypropoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC(O)CCl OVEPNAHYQINONH-UHFFFAOYSA-N 0.000 description 1
- KGRFDQPMJNJEQB-UHFFFAOYSA-N 1-[3-(oxiran-2-ylmethoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=CC(OCC2OC2)=C1 KGRFDQPMJNJEQB-UHFFFAOYSA-N 0.000 description 1
- HBJRNQOAQXJYPB-UHFFFAOYSA-N 1-[4-(oxiran-2-ylmethoxy)phenyl]ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1OC1 HBJRNQOAQXJYPB-UHFFFAOYSA-N 0.000 description 1
- HBZFZWZRHMJQRV-UHFFFAOYSA-N 1-chloro-3-(2-ethoxyphenoxy)propan-2-ol Chemical compound ClCC(COC1=C(C=CC=C1)OCC)O HBZFZWZRHMJQRV-UHFFFAOYSA-N 0.000 description 1
- JNLRDAZOIOYMGZ-UHFFFAOYSA-N 1-chloro-3-(2-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=CC=C1OCC(O)CCl JNLRDAZOIOYMGZ-UHFFFAOYSA-N 0.000 description 1
- KCALVOJZPVBWTD-UHFFFAOYSA-N 1-chloro-3-(3-ethylphenoxy)propan-2-ol Chemical compound ClCC(COC1=CC(=CC=C1)CC)O KCALVOJZPVBWTD-UHFFFAOYSA-N 0.000 description 1
- BNQQDHHUNXPXSB-UHFFFAOYSA-N 1-chloro-3-(3-methylphenoxy)propan-2-ol Chemical compound CC1=CC=CC(OCC(O)CCl)=C1 BNQQDHHUNXPXSB-UHFFFAOYSA-N 0.000 description 1
- QGRUJUCGIQGDBO-UHFFFAOYSA-N 1-chloro-3-(3-propan-2-ylphenoxy)propan-2-ol Chemical compound ClCC(COC1=CC(=CC=C1)C(C)C)O QGRUJUCGIQGDBO-UHFFFAOYSA-N 0.000 description 1
- OOZBNYBOYJYSNZ-UHFFFAOYSA-N 1-chloro-3-(4-methoxyphenoxy)propan-2-ol Chemical compound COC1=CC=C(OCC(O)CCl)C=C1 OOZBNYBOYJYSNZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- XQJAHZMRYGGGNY-UHFFFAOYSA-N 4-(3-chloro-2-hydroxypropoxy)benzonitrile Chemical compound ClCC(COC1=CC=C(C=C1)C#N)O XQJAHZMRYGGGNY-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 229960001413 acetanilide Drugs 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000464 adrenergic agent Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 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
- 235000015165 citric acid Nutrition 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 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
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical compound [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 210000005092 tracheal tissue Anatomy 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
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US00207954A US3857891A (en) | 1971-12-14 | 1971-12-14 | New aminoalkanol compounds and methods for their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135244B true NO135244B (nl) | 1976-11-29 |
| NO135244C NO135244C (nl) | 1977-03-09 |
Family
ID=22772656
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO4113/72A NO135244C (nl) | 1971-12-14 | 1972-11-14 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3857891A (nl) |
| JP (1) | JPS5233621B2 (nl) |
| AR (2) | AR195896A1 (nl) |
| AT (1) | AT317182B (nl) |
| AU (1) | AU475446B2 (nl) |
| BE (1) | BE790165A (nl) |
| CA (1) | CA993889A (nl) |
| CH (1) | CH551371A (nl) |
| DK (1) | DK134906B (nl) |
| ES (1) | ES409565A1 (nl) |
| FI (1) | FI55650C (nl) |
| FR (1) | FR2163486B1 (nl) |
| GB (1) | GB1344976A (nl) |
| HU (1) | HU164953B (nl) |
| IE (1) | IE37701B1 (nl) |
| IL (1) | IL40833A (nl) |
| NL (1) | NL150101B (nl) |
| NO (1) | NO135244C (nl) |
| SE (1) | SE393104B (nl) |
| YU (2) | YU35871B (nl) |
| ZA (1) | ZA727078B (nl) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2119843B1 (nl) * | 1970-12-28 | 1974-03-22 | Laroche Navarro Labo | |
| JPS5653534B2 (nl) * | 1973-10-25 | 1981-12-19 | ||
| SE388849B (sv) * | 1974-02-14 | 1976-10-18 | Haessle Ab | Forfarande for framstellning av nya aminer med beta-receptorstimulerande verkan |
| US4081447A (en) * | 1975-04-09 | 1978-03-28 | Abbott Laboratories | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof |
| US4080471A (en) * | 1976-06-25 | 1978-03-21 | Aktiebolaget Hassle | Use of substituted isopropylaminopropanols for inducing inotropic effects of the human heart |
| JPS56158868A (en) * | 1980-05-13 | 1981-12-07 | Satake Eng Co Ltd | Ion nitriding treatment device |
| ZA852843B (en) * | 1984-05-15 | 1985-11-27 | Warner Lambert Co | Bevantolol preparation |
| US5095151A (en) * | 1985-05-21 | 1992-03-10 | American Home Products Corporation | Preparation of propranolol hydrochloride macrocrystals |
| US4789751A (en) * | 1985-10-01 | 1988-12-06 | University Patents, Inc. | Synthesis of new liquid crystal materials possessing phenylbenzoate or biphenyl core units and (2,3)-epoalkyloxirane methanol chiral tails |
| JP2587336B2 (ja) * | 1991-10-03 | 1997-03-05 | 日本ケミファ株式会社 | 塩酸ベバントロールの製造方法 |
| US5482964A (en) * | 1994-10-11 | 1996-01-09 | Warner-Lambert Company | Substituted phenoxyhydroxypropyl amines as central nervous system agents |
| TW467881B (en) * | 1997-07-31 | 2001-12-11 | Ying-Jiun Chen | Guaiacoxypropanolamines with Α/β-adrenergic blocking activity |
| AU8527798A (en) * | 1998-07-23 | 2000-02-14 | Ing-Jun Chen | Guaiacoxypropanolamine derivatives with alpha/beta-adrenergic blocking activity |
| AP2005003232A0 (en) | 2002-08-19 | 2005-03-31 | Pfizer Prod Inc | Combination therapy for hyperproliferative diseases. |
| JP4901474B2 (ja) | 2003-05-30 | 2012-03-21 | ランバクシー ラボラトリーズ リミテッド | 置換ピロール誘導体 |
| CN1884251B (zh) * | 2005-06-22 | 2010-06-23 | 北京德众万全医药科技有限公司 | 一种盐酸贝凡洛尔的精制方法 |
| KR101329112B1 (ko) | 2005-11-08 | 2013-11-14 | 랜박시 래보러터리스 리미티드 | (3ｒ,5ｒ)-7-〔2-(4-플루오로페닐)-5-이소프로필-3-페닐-4-〔(4-히드록시 메틸 페닐 아미노)카르보닐〕-피롤-1-일〕-3,5-디히드록시 헵탄산 헤미 칼슘염의 제조 방법 |
| KR102254542B1 (ko) * | 2013-06-19 | 2021-05-24 | 솜 이노베이션 바이오테크, 에스.엘. | 과다운동성 운동 장애의 예방 및/또는 치료에 사용하기 위한 치료제 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL300886A (nl) * | 1962-11-23 | |||
| NL301580A (nl) * | 1962-12-11 | |||
| GB1069343A (en) * | 1963-09-10 | 1967-05-17 | Ici Ltd | Propanolamine derivatives |
-
0
- BE BE790165D patent/BE790165A/xx not_active IP Right Cessation
-
1971
- 1971-12-14 US US00207954A patent/US3857891A/en not_active Expired - Lifetime
-
1972
- 1972-10-03 ZA ZA727078A patent/ZA727078B/xx unknown
- 1972-11-10 CA CA156,190A patent/CA993889A/en not_active Expired
- 1972-11-14 IE IE1562/72A patent/IE37701B1/xx unknown
- 1972-11-14 NO NO4113/72A patent/NO135244C/no unknown
- 1972-11-14 IL IL40833A patent/IL40833A/xx unknown
- 1972-11-14 FI FI3180/72A patent/FI55650C/fi active
- 1972-11-23 AU AU49186/72A patent/AU475446B2/en not_active Expired
- 1972-11-23 GB GB5426172A patent/GB1344976A/en not_active Expired
- 1972-11-28 AT AT1010572A patent/AT317182B/de not_active IP Right Cessation
- 1972-11-30 CH CH1746772A patent/CH551371A/fr not_active IP Right Cessation
- 1972-11-30 NL NL727216281A patent/NL150101B/nl not_active IP Right Cessation
- 1972-12-06 YU YU3019/72A patent/YU35871B/xx unknown
- 1972-12-07 FR FR7243545A patent/FR2163486B1/fr not_active Expired
- 1972-12-11 AR AR245573A patent/AR195896A1/es active
- 1972-12-12 JP JP47124055A patent/JPS5233621B2/ja not_active Expired
- 1972-12-12 DK DK619172AA patent/DK134906B/da not_active IP Right Cessation
- 1972-12-13 HU HUPA1153A patent/HU164953B/hu unknown
- 1972-12-13 ES ES409565A patent/ES409565A1/es not_active Expired
- 1972-12-13 SE SE7216240A patent/SE393104B/xx unknown
-
1973
- 1973-10-15 AR AR250507A patent/AR198442A1/es active
-
1979
- 1979-12-03 YU YU2939/79A patent/YU36007B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU301972A (en) | 1981-02-28 |
| JPS4867232A (nl) | 1973-09-13 |
| US3857891A (en) | 1974-12-31 |
| NL7216281A (nl) | 1973-06-18 |
| HU164953B (nl) | 1974-05-28 |
| AT317182B (de) | 1974-08-12 |
| CA993889A (en) | 1976-07-27 |
| AU475446B2 (en) | 1976-08-26 |
| FR2163486B1 (nl) | 1976-03-05 |
| AR195896A1 (es) | 1973-11-15 |
| DE2259489A1 (de) | 1973-07-05 |
| YU293979A (en) | 1981-04-30 |
| ES409565A1 (es) | 1975-12-01 |
| GB1344976A (en) | 1974-01-23 |
| IE37701B1 (en) | 1977-09-28 |
| FI55650C (fi) | 1979-09-10 |
| JPS5233621B2 (nl) | 1977-08-30 |
| BE790165A (fr) | 1973-02-15 |
| AU4918672A (en) | 1974-05-23 |
| AR198442A1 (es) | 1974-06-21 |
| FI55650B (fi) | 1979-05-31 |
| CH551371A (fr) | 1974-07-15 |
| IE37701L (en) | 1973-05-14 |
| IL40833A0 (en) | 1973-01-30 |
| ZA727078B (en) | 1973-06-27 |
| DE2259489B2 (de) | 1976-02-26 |
| DK134906B (da) | 1977-02-07 |
| YU35871B (en) | 1981-08-31 |
| DK134906C (nl) | 1977-06-27 |
| YU36007B (en) | 1981-11-13 |
| NO135244C (nl) | 1977-03-09 |
| SE393104B (sv) | 1977-05-02 |
| FR2163486A1 (nl) | 1973-07-27 |
| NL150101B (nl) | 1976-07-15 |
| IL40833A (en) | 1976-01-30 |
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