PL97061B1 - Sposob wytwarzania nowych podstawionych p-alkoksyalkoksyfenoksyhydroksypropyloamin - Google Patents
Sposob wytwarzania nowych podstawionych p-alkoksyalkoksyfenoksyhydroksypropyloamin Download PDFInfo
- Publication number
- PL97061B1 PL97061B1 PL1970189884A PL18988470A PL97061B1 PL 97061 B1 PL97061 B1 PL 97061B1 PL 1970189884 A PL1970189884 A PL 1970189884A PL 18988470 A PL18988470 A PL 18988470A PL 97061 B1 PL97061 B1 PL 97061B1
- Authority
- PL
- Poland
- Prior art keywords
- formula
- compound
- propanol
- defined above
- isopropylamino
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 29
- -1 p-methoxyethoxy-phenoxy Chemical group 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 4
- 230000010247 heart contraction Effects 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 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 claims description 2
- 241000700199 Cavia porcellus Species 0.000 claims description 2
- 241000699670 Mus sp. Species 0.000 claims description 2
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 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 claims description 2
- 229960003147 reserpine Drugs 0.000 claims description 2
- 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 claims description 2
- HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical group C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 claims 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 230000036513 peripheral conductance Effects 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 229960001317 isoprenaline Drugs 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- YOVIHUPQPSJARA-UHFFFAOYSA-N 2-[[4-(2-methoxyethoxy)phenoxy]methyl]oxirane Chemical compound C1=CC(OCCOC)=CC=C1OCC1OC1 YOVIHUPQPSJARA-UHFFFAOYSA-N 0.000 description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- 230000000903 blocking effect Effects 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 208000006673 asthma Diseases 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000282326 Felis catus Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 230000036772 blood pressure Effects 0.000 description 2
- 210000004204 blood vessel Anatomy 0.000 description 2
- 210000000621 bronchi Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 230000002093 peripheral effect Effects 0.000 description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 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
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000002792 vascular Effects 0.000 description 2
- ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-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
- GCFQBKAQFZQKFR-UHFFFAOYSA-N 2-[[4-(2-ethoxyethoxy)phenyl]-[[4-(2-ethoxyethoxy)phenyl]-(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound C(C)OCCOC1=CC=C(C=C1)C(C1CO1)OC(C1CO1)C1=CC=C(C=C1)OCCOCC GCFQBKAQFZQKFR-UHFFFAOYSA-N 0.000 description 1
- WZZLWDIURDVSMW-UHFFFAOYSA-N 2-[[4-[2-(2-methoxyethoxy)ethoxy]phenyl]-[[4-[2-(2-methoxyethoxy)ethoxy]phenyl]-(oxiran-2-yl)methoxy]methyl]oxirane Chemical compound COCCOCCOC1=CC=C(C=C1)C(C1CO1)OC(C1CO1)C1=CC=C(C=C1)OCCOCCOC WZZLWDIURDVSMW-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
- NIGIGWPNXVNZRK-UHFFFAOYSA-N 4-(2-methoxyethoxy)phenol Chemical compound COCCOC1=CC=C(O)C=C1 NIGIGWPNXVNZRK-UHFFFAOYSA-N 0.000 description 1
- KZUHCFQPADLISK-UHFFFAOYSA-N 4-(2-propan-2-yloxyethoxy)phenol Chemical compound CC(C)OCCOC1=CC=C(O)C=C1 KZUHCFQPADLISK-UHFFFAOYSA-N 0.000 description 1
- JHTVLTCTJRDPSF-UHFFFAOYSA-N 4-(3-methoxypropoxy)phenol Chemical compound COCCCOC1=CC=C(O)C=C1 JHTVLTCTJRDPSF-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
- 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 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000009079 Bronchial Spasm 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
- KPUUDULFHAUIMB-UHFFFAOYSA-N CC(C)OCCOC1=CC=C(C(C2OC2)OC(C2OC2)C(C=C2)=CC=C2OCCOC(C)C)C=C1 Chemical compound CC(C)OCCOC1=CC=C(C(C2OC2)OC(C2OC2)C(C=C2)=CC=C2OCCOC(C)C)C=C1 KPUUDULFHAUIMB-UHFFFAOYSA-N 0.000 description 1
- VATVBBVANZMSAS-UHFFFAOYSA-N COCCCOC1=CC=C(C(C2OC2)OC(C2OC2)C(C=C2)=CC=C2OCCCOC)C=C1 Chemical compound COCCCOC1=CC=C(C(C2OC2)OC(C2OC2)C(C=C2)=CC=C2OCCCOC)C=C1 VATVBBVANZMSAS-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 206010049816 Muscle tightness Diseases 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
- 206010029333 Neurosis Diseases 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical class C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-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
- 210000004100 adrenal gland Anatomy 0.000 description 1
- PAZJSJFMUHDSTF-UHFFFAOYSA-N alprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1CC=C PAZJSJFMUHDSTF-UHFFFAOYSA-N 0.000 description 1
- 229960002213 alprenolol Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 210000000544 articulatio talocruralis Anatomy 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 210000001715 carotid artery Anatomy 0.000 description 1
- 230000002057 chronotropic effect Effects 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000000994 depressogenic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method 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
- 210000004013 groin Anatomy 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 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
- 210000005036 nerve Anatomy 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 210000001331 nose Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000012071 phase 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
- 229960003712 propranolol Drugs 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QGMRQYFBGABWDR-UHFFFAOYSA-N sodium;5-ethyl-5-pentan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)NC1=O QGMRQYFBGABWDR-UHFFFAOYSA-N 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid group Chemical class S(N)(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 230000024883 vasodilation 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (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)
- Epidemiology (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 (en, 2012) | 1969-05-21 | 1969-05-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL97061B1 true PL97061B1 (pl) | 1978-02-28 |
Family
ID=20270562
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970189884A PL97061B1 (pl) | 1969-05-21 | 1970-04-27 | Sposob wytwarzania nowych podstawionych p-alkoksyalkoksyfenoksyhydroksypropyloamin |
| PL1970140271A PL72300B1 (en, 2012) | 1969-05-21 | 1970-04-27 | |
| PL1970189885A PL94849B1 (pl) | 1969-05-21 | 1970-04-27 | Sposob wytwarzania nowych,podstawionych p-alkoksyalkoksyfenoksyhydroksypropyloamin |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1970140271A PL72300B1 (en, 2012) | 1969-05-21 | 1970-04-27 | |
| PL1970189885A PL94849B1 (pl) | 1969-05-21 | 1970-04-27 | Sposob wytwarzania nowych,podstawionych p-alkoksyalkoksyfenoksyhydroksypropyloamin |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3674840A (en, 2012) |
| JP (2) | JPS5123488B1 (en, 2012) |
| AT (3) | AT307384B (en, 2012) |
| BE (1) | BE749244A (en, 2012) |
| CA (1) | CA979460A (en, 2012) |
| CH (3) | CH564514A5 (en, 2012) |
| CS (3) | CS167284B2 (en, 2012) |
| DE (1) | DE2020864C3 (en, 2012) |
| DK (1) | DK136527B (en, 2012) |
| ES (3) | ES379062A1 (en, 2012) |
| FI (1) | FI55175C (en, 2012) |
| FR (1) | FR2044806B1 (en, 2012) |
| GB (1) | GB1298017A (en, 2012) |
| IE (1) | IE34201B1 (en, 2012) |
| NL (1) | NL166462C (en, 2012) |
| NO (1) | NO129792B (en, 2012) |
| PL (3) | PL97061B1 (en, 2012) |
| SE (1) | SE372762B (en, 2012) |
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 (en, 2012) * | 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 |
| US9233165B2 (en) * | 2008-04-11 | 2016-01-12 | Nektar Therapeutics | Oligomer-aryloxy-substituted propanamine conjugates |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL300886A (en, 2012) * | 1962-11-23 | |||
| US3275629A (en) * | 1963-03-20 | 1966-09-27 | Monsanto Co | Substituted aryloxyalkylene amines |
| GB1095378A (en, 2012) * | 1965-06-22 | |||
| JPS5318117B2 (en, 2012) * | 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 CS CS8729*A patent/CS167283B2/cs unknown
- 1970-04-21 CS CS2692A patent/CS167282B2/cs unknown
- 1970-04-21 BE BE749244D patent/BE749244A/xx not_active IP Right Cessation
- 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 DK DK212670AA patent/DK136527B/da not_active IP Right Cessation
- 1970-04-27 PL PL1970189884A patent/PL97061B1/pl unknown
- 1970-04-27 PL PL1970140271A patent/PL72300B1/pl unknown
- 1970-04-27 PL PL1970189885A patent/PL94849B1/pl unknown
- 1970-04-29 DE DE2020864A patent/DE2020864C3/de not_active Expired
- 1970-05-05 CH CH1685974A patent/CH564514A5/xx not_active IP Right Cessation
- 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 CH669170A patent/CH564512A5/xx not_active IP Right Cessation
- 1970-05-08 AT AT414570A patent/AT307384B/de active
- 1970-05-08 AT AT764172A patent/AT310145B/de not_active IP Right Cessation
- 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
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