NO129792B - - Google Patents
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- Publication number
- NO129792B NO129792B NO01714/70A NO171470A NO129792B NO 129792 B NO129792 B NO 129792B NO 01714/70 A NO01714/70 A NO 01714/70A NO 171470 A NO171470 A NO 171470A NO 129792 B NO129792 B NO 129792B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- formula
- same meaning
- hydrolyzes
- formation
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims description 64
- 238000000034 method Methods 0.000 claims description 15
- 239000000203 mixture Substances 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 7
- 208000019622 heart disease Diseases 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 230000003287 optical effect Effects 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 150000007513 acids Chemical class 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims description 2
- 150000008046 alkali metal hydrides Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 11
- 229960001317 isoprenaline Drugs 0.000 description 11
- 239000000126 substance Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000019441 ethanol Nutrition 0.000 description 9
- -1 p- hydroxy- hydroxy-substituted phenoxy-hydroxypropylamines Chemical class 0.000 description 9
- 238000009835 boiling Methods 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 5
- 229960002213 alprenolol Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 210000003205 muscle Anatomy 0.000 description 5
- NIGIGWPNXVNZRK-UHFFFAOYSA-N 4-(2-methoxyethoxy)phenol Chemical compound COCCOC1=CC=C(O)C=C1 NIGIGWPNXVNZRK-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000282326 Felis catus Species 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 210000004204 blood vessel Anatomy 0.000 description 4
- 210000000621 bronchi Anatomy 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 230000001225 therapeutic effect Effects 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- YOVIHUPQPSJARA-UHFFFAOYSA-N 2-[[4-(2-methoxyethoxy)phenoxy]methyl]oxirane Chemical compound C1=CC(OCCOC)=CC=C1OCC1OC1 YOVIHUPQPSJARA-UHFFFAOYSA-N 0.000 description 2
- LBSOXWCAEGGPDY-UHFFFAOYSA-N 3-(phenoxyamino)propan-1-ol Chemical class OCCCNOC1=CC=CC=C1 LBSOXWCAEGGPDY-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical class C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000002057 chronotropic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 230000001965 increasing effect Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- 239000001294 propane Substances 0.000 description 2
- 239000003087 receptor blocking agent Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 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
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 1
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- KNTZCGBYFGEMFR-UHFFFAOYSA-N (propan-2-ylazaniumyl)formate Chemical compound CC(C)NC(O)=O KNTZCGBYFGEMFR-UHFFFAOYSA-N 0.000 description 1
- JGKUSJQXMQBLHE-UHFFFAOYSA-N 2-[[4-(2-ethoxyethoxy)phenoxy]methyl]oxirane Chemical compound C1=CC(OCCOCC)=CC=C1OCC1OC1 JGKUSJQXMQBLHE-UHFFFAOYSA-N 0.000 description 1
- NOINXHTVSPBTHE-UHFFFAOYSA-N 2-[[4-(2-methoxyethoxy)phenyl]-[[4-(2-methoxyethoxy)phenyl]-(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound COCCOC1=CC=C(C=C1)C(C1CO1)OC(C1CO1)C1=CC=C(C=C1)OCCOC NOINXHTVSPBTHE-UHFFFAOYSA-N 0.000 description 1
- DXWCOLYKOCDGSR-UHFFFAOYSA-N 2-[[4-(2-propan-2-yloxyethoxy)phenoxy]methyl]oxirane Chemical compound C1=CC(OCCOC(C)C)=CC=C1OCC1OC1 DXWCOLYKOCDGSR-UHFFFAOYSA-N 0.000 description 1
- KMGUEILFFWDGFV-UHFFFAOYSA-N 2-benzoyl-2-benzoyloxy-3-hydroxybutanedioic acid Chemical compound C=1C=CC=CC=1C(=O)C(C(C(O)=O)O)(C(O)=O)OC(=O)C1=CC=CC=C1 KMGUEILFFWDGFV-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- YCNXLAJVXGTQEL-UHFFFAOYSA-N 4-(2-ethoxyethoxy)phenol Chemical compound CCOCCOC1=CC=C(O)C=C1 YCNXLAJVXGTQEL-UHFFFAOYSA-N 0.000 description 1
- YOZSDUPFXGVCCI-UHFFFAOYSA-N 4-[2-(2-methoxyethoxy)ethoxy]phenol Chemical compound COCCOCCOC1=CC=C(O)C=C1 YOZSDUPFXGVCCI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 208000014181 Bronchial disease Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- YOQDWENIELRQAK-UHFFFAOYSA-N C(C1=CC=CC=C1)OCOCCOC1=CC=CC=C1 Chemical compound C(C1=CC=CC=C1)OCOCCOC1=CC=CC=C1 YOQDWENIELRQAK-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-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
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- WXNXCEHXYPACJF-SSDOTTSWSA-N N-acetyl-D-leucine Chemical compound CC(C)C[C@H](C(O)=O)NC(C)=O WXNXCEHXYPACJF-SSDOTTSWSA-N 0.000 description 1
- WXNXCEHXYPACJF-ZETCQYMHSA-M N-acetyl-L-leucinate Chemical compound CC(C)C[C@@H](C([O-])=O)NC(C)=O WXNXCEHXYPACJF-ZETCQYMHSA-M 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 description 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 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
- 230000001154 acute effect Effects 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 210000003423 ankle Anatomy 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 230000006793 arrhythmia Effects 0.000 description 1
- 210000001367 artery Anatomy 0.000 description 1
- 230000002146 bilateral effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 230000004531 blood pressure lowering effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 210000001105 femoral artery Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 210000002683 foot Anatomy 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 238000001361 intraarterial administration Methods 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- NZWOPGCLSHLLPA-UHFFFAOYSA-N methacholine Chemical compound C[N+](C)(C)CC(C)OC(C)=O NZWOPGCLSHLLPA-UHFFFAOYSA-N 0.000 description 1
- 229960002329 methacholine Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229960004570 oxprenolol Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000036581 peripheral resistance Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- BOTNYLSAWDQNEX-UHFFFAOYSA-N phenoxymethylbenzene Chemical class C=1C=CC=CC=1COC1=CC=CC=C1 BOTNYLSAWDQNEX-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
- 229960003147 reserpine Drugs 0.000 description 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-M sulfamate Chemical compound NS([O-])(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-M 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 230000003422 vasoregulatory effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- 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
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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 |
|---|---|---|---|
| SE6907153A SE372762B (ja) | 1969-05-21 | 1969-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129792B true NO129792B (ja) | 1974-05-27 |
Family
ID=20270562
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01714/70A NO129792B (ja) | 1969-05-21 | 1970-05-05 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3674840A (ja) |
| JP (2) | JPS5123488B1 (ja) |
| AT (3) | AT310145B (ja) |
| BE (1) | BE749244A (ja) |
| CA (1) | CA979460A (ja) |
| CH (3) | CH562776A5 (ja) |
| CS (3) | CS167284B2 (ja) |
| DE (1) | DE2020864C3 (ja) |
| DK (1) | DK136527B (ja) |
| ES (3) | ES379062A1 (ja) |
| FI (1) | FI55175C (ja) |
| FR (1) | FR2044806B1 (ja) |
| GB (1) | GB1298017A (ja) |
| IE (1) | IE34201B1 (ja) |
| NL (1) | NL166462C (ja) |
| NO (1) | NO129792B (ja) |
| PL (3) | PL72300B1 (ja) |
| SE (1) | SE372762B (ja) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE384853B (sv) * | 1972-04-04 | 1976-05-24 | Haessle Ab | Forfarande for framstellning av nya aminer |
| GB1312555A (en) * | 1971-02-09 | 1973-04-04 | Ici Ltd | Alkanolamine derivatives |
| GB1387630A (en) * | 1971-05-07 | 1975-03-19 | Ici Ltd | Phenoxyalkanolamine derivatives |
| SE386892B (sv) * | 1972-07-06 | 1976-08-23 | Haessle Ab | Forfarande for framstellning av oxaminoforeningar |
| CH585693A5 (ja) * | 1974-02-08 | 1977-03-15 | Ciba Geigy Ag | |
| FR2330383A1 (fr) * | 1975-11-06 | 1977-06-03 | Synthelabo | Nouveaux ethers de phenols substitues, leurs sels, leur preparation et les medicaments qui les renferment |
| DE2645710C2 (de) * | 1976-10-09 | 1985-06-27 | Merck Patent Gmbh, 6100 Darmstadt | Phenoxy-amino-propanole, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitung |
| IT1147311B (it) * | 1980-02-13 | 1986-11-19 | Stabil Bioterapico Farmachim | Eteri basici di 4-idrossi-benzofenoni con attivita' quali agenti betabloccanti e relativi procedimento di preparazione |
| ZW9881A1 (en) * | 1980-06-02 | 1981-12-23 | Hoffmann La Roche | Substituted phenoxyaminopropanol derivatives |
| US4342783A (en) * | 1980-06-30 | 1982-08-03 | Synthelabo | Anti-glaucoma agent |
| ATE19510T1 (de) * | 1981-12-17 | 1986-05-15 | Haessle Ab | Para-substituierte 3-phenoxy-1carbonylaminoalkylaminopropan-2-ole mit blockierenden wirkungen bei betarezeptoren. |
| US4968829A (en) * | 1984-07-18 | 1990-11-06 | Sandoz Ltd. | Novel substituted aromatic compounds |
| US4568354A (en) * | 1985-06-03 | 1986-02-04 | Texaco Inc. | Conversion of hazy gasoline to clear stable gasoline |
| EP0252007A3 (en) * | 1986-06-28 | 1989-07-05 | Ciba-Geigy Ag | 2-propanol derivatives as corrosion inhibitors |
| EP0283540B1 (de) * | 1987-03-26 | 1991-09-18 | Helopharm W. Petrik GmbH & Co.KG. | Verfahren zur Herstellung von 5-Hydroxydiprafenon und seiner Salze mit Säuren |
| MX2010011101A (es) * | 2008-04-11 | 2010-11-01 | Nektar Therapeutics | Conjugados de oligomero-propanamina sustituida con ariloxi. |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL300886A (ja) * | 1962-11-23 | |||
| US3275629A (en) * | 1963-03-20 | 1966-09-27 | Monsanto Co | Substituted aryloxyalkylene amines |
| GB1095378A (ja) * | 1965-06-22 | |||
| JPS5318117B2 (ja) * | 1972-07-31 | 1978-06-13 |
-
1969
- 1969-05-21 SE SE6907153A patent/SE372762B/xx unknown
-
1970
- 1970-04-08 CA CA079,530A patent/CA979460A/en not_active Expired
- 1970-04-17 FI FI1077/70A patent/FI55175C/fi active
- 1970-04-21 CS CS8730*A patent/CS167284B2/cs unknown
- 1970-04-21 BE BE749244D patent/BE749244A/xx not_active IP Right Cessation
- 1970-04-21 CS CS8729*A patent/CS167283B2/cs unknown
- 1970-04-21 CS CS2692A patent/CS167282B2/cs unknown
- 1970-04-24 FR FR7015123A patent/FR2044806B1/fr not_active Expired
- 1970-04-25 ES ES379062A patent/ES379062A1/es not_active Expired
- 1970-04-27 PL PL1970140271A patent/PL72300B1/pl unknown
- 1970-04-27 DK DK212670AA patent/DK136527B/da not_active IP Right Cessation
- 1970-04-27 PL PL1970189885A patent/PL94849B1/pl unknown
- 1970-04-27 PL PL1970189884A patent/PL97061B1/pl unknown
- 1970-04-29 DE DE2020864A patent/DE2020864C3/de not_active Expired
- 1970-05-05 CH CH1685874A patent/CH562776A5/xx not_active IP Right Cessation
- 1970-05-05 NO NO01714/70A patent/NO129792B/no unknown
- 1970-05-05 CH CH1685974A patent/CH564514A5/xx not_active IP Right Cessation
- 1970-05-05 CH CH669170A patent/CH564512A5/xx not_active IP Right Cessation
- 1970-05-08 AT AT764172A patent/AT310145B/de not_active IP Right Cessation
- 1970-05-08 AT AT414570A patent/AT307384B/de active
- 1970-05-08 AT AT149472A patent/AT308723B/de not_active IP Right Cessation
- 1970-05-19 JP JP45042518A patent/JPS5123488B1/ja active Pending
- 1970-05-19 US US38884A patent/US3674840A/en not_active Expired - Lifetime
- 1970-05-20 GB GB24499/70A patent/GB1298017A/en not_active Expired
- 1970-05-20 IE IE662/70A patent/IE34201B1/xx unknown
- 1970-05-21 NL NL7007379.A patent/NL166462C/xx not_active IP Right Cessation
-
1972
- 1972-10-16 ES ES407663A patent/ES407663A1/es not_active Expired
- 1972-10-16 ES ES407664A patent/ES407664A1/es not_active Expired
-
1975
- 1975-09-26 JP JP50115693A patent/JPS5247447B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK136527C (ja) | 1978-05-01 |
| IE34201B1 (en) | 1975-03-05 |
| CS167283B2 (ja) | 1976-04-29 |
| DE2020864C3 (de) | 1981-01-08 |
| CH564512A5 (ja) | 1975-07-31 |
| CA979460A (en) | 1975-12-09 |
| PL94849B1 (pl) | 1977-08-31 |
| ES407663A1 (es) | 1975-10-16 |
| DE2020864A1 (de) | 1970-11-26 |
| FI55175C (fi) | 1979-06-11 |
| FI55175B (fi) | 1979-02-28 |
| AT307384B (de) | 1973-05-25 |
| BE749244A (fr) | 1970-10-01 |
| IE34201L (en) | 1970-11-21 |
| DE2020864B2 (de) | 1980-05-08 |
| JPS5247447B1 (ja) | 1977-12-02 |
| AT310145B (de) | 1973-09-25 |
| DK136527B (da) | 1977-10-24 |
| CH562776A5 (ja) | 1975-06-13 |
| FR2044806A1 (ja) | 1971-02-26 |
| ES379062A1 (es) | 1973-02-01 |
| FR2044806B1 (ja) | 1974-08-30 |
| NL7007379A (ja) | 1970-11-24 |
| CH564514A5 (ja) | 1975-07-31 |
| SE372762B (ja) | 1975-01-13 |
| PL97061B1 (pl) | 1978-02-28 |
| GB1298017A (en) | 1972-11-29 |
| JPS5123488B1 (ja) | 1976-07-17 |
| US3674840A (en) | 1972-07-04 |
| CS167284B2 (ja) | 1976-04-29 |
| AT308723B (de) | 1973-07-25 |
| ES407664A1 (es) | 1975-10-16 |
| NL166462C (nl) | 1981-08-17 |
| CS167282B2 (ja) | 1976-04-29 |
| PL72300B1 (ja) | 1974-06-29 |
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