DE2048838A1 - Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung - Google Patents
Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellungInfo
- Publication number
- DE2048838A1 DE2048838A1 DE19702048838 DE2048838A DE2048838A1 DE 2048838 A1 DE2048838 A1 DE 2048838A1 DE 19702048838 DE19702048838 DE 19702048838 DE 2048838 A DE2048838 A DE 2048838A DE 2048838 A1 DE2048838 A1 DE 2048838A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- group
- hydroxy
- compounds
- compound
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 49
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 title description 2
- -1 alkyl radical Chemical class 0.000 claims description 62
- 150000001875 compounds Chemical class 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 22
- 239000004480 active ingredient Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 19
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 19
- 239000000126 substance Substances 0.000 claims description 18
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000002431 hydrogen Chemical class 0.000 claims description 6
- 150000003254 radicals Chemical class 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000006239 protecting group Chemical group 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 150000003672 ureas Chemical class 0.000 claims description 4
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- 150000005840 aryl radicals Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 125000004043 oxo group Chemical group O=* 0.000 claims description 2
- 238000011321 prophylaxis Methods 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims 5
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 239000012876 carrier material Substances 0.000 claims 1
- 238000001640 fractional crystallisation Methods 0.000 claims 1
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 210000001550 testis Anatomy 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 68
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 59
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 25
- 239000002585 base Substances 0.000 description 22
- 239000000243 solution Substances 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 12
- 238000001704 evaporation Methods 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- 238000001035 drying Methods 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
- 239000012071 phase Substances 0.000 description 8
- 238000010992 reflux Methods 0.000 description 8
- 238000006722 reduction reaction Methods 0.000 description 7
- BKMMTJMQCTUHRP-UHFFFAOYSA-N 2-aminopropan-1-ol Chemical compound CC(N)CO BKMMTJMQCTUHRP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000007098 aminolysis reaction Methods 0.000 description 6
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- 229940058020 2-amino-2-methyl-1-propanol Drugs 0.000 description 5
- 229920002261 Corn starch Polymers 0.000 description 5
- 239000008120 corn starch Substances 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- PYNUOAIJIQGACY-UHFFFAOYSA-N propylazanium;chloride Chemical compound Cl.CCCN PYNUOAIJIQGACY-UHFFFAOYSA-N 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 229920000623 Cellulose acetate phthalate Polymers 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229940081734 cellulose acetate phthalate Drugs 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 235000019359 magnesium stearate Nutrition 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 238000006193 diazotization reaction Methods 0.000 description 3
- 239000008298 dragée Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- BARKHCPMEPSMHY-UHFFFAOYSA-N (2-prop-1-enoxyphenyl)methanol Chemical group CC=COC1=CC=CC=C1CO BARKHCPMEPSMHY-UHFFFAOYSA-N 0.000 description 2
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 2
- MFKJRCZRAWTCHS-UHFFFAOYSA-N 2-(1-amino-2,5-dihydroxy-4,4-dimethylpentoxy)benzonitrile Chemical compound C(#N)C1=C(OC(C(CC(CO)(C)C)O)N)C=CC=C1 MFKJRCZRAWTCHS-UHFFFAOYSA-N 0.000 description 2
- OCDHRUIARWXIBR-UHFFFAOYSA-N 2-[(2-prop-2-ynoxyphenoxy)methyl]oxirane Chemical compound C#CCOC1=CC=CC=C1OCC1OC1 OCDHRUIARWXIBR-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000004103 aminoalkyl group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229910000389 calcium phosphate Inorganic materials 0.000 description 2
- 235000011010 calcium phosphates Nutrition 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000005660 chlorination reaction Methods 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 239000008119 colloidal silica Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000007903 gelatin capsule Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- 235000006408 oxalic acid Nutrition 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 150000003141 primary amines Chemical class 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
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- LTIZQAANULHFEW-UHFFFAOYSA-N 1-nitro-2-prop-1-enoxybenzene Chemical group CC=COC1=CC=CC=C1[N+]([O-])=O LTIZQAANULHFEW-UHFFFAOYSA-N 0.000 description 1
- JFUBFTVIDOXELL-UHFFFAOYSA-N 2-(3-amino-2-hydroxypropoxy)benzonitrile Chemical compound NCC(O)COC1=CC=CC=C1C#N JFUBFTVIDOXELL-UHFFFAOYSA-N 0.000 description 1
- HUHXLHLWASNVDB-UHFFFAOYSA-N 2-(oxan-2-yloxy)oxane Chemical compound O1CCCCC1OC1OCCCC1 HUHXLHLWASNVDB-UHFFFAOYSA-N 0.000 description 1
- JCBPETKZIGVZRE-UHFFFAOYSA-N 2-aminobutan-1-ol Chemical compound CCC(N)CO JCBPETKZIGVZRE-UHFFFAOYSA-N 0.000 description 1
- VZIQXGLTRZLBEX-UHFFFAOYSA-N 2-chloro-1-propanol Chemical compound CC(Cl)CO VZIQXGLTRZLBEX-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- UQKCKPROSFGNIU-UHFFFAOYSA-N 3-amino-2-methylpentan-1-ol Chemical compound CCC(N)C(C)CO UQKCKPROSFGNIU-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
- VHHSSWHGQQTOBV-UHFFFAOYSA-N 4-methyl-2-(oxiran-2-ylmethoxy)benzonitrile Chemical compound CC1=CC=C(C#N)C(OCC2OC2)=C1 VHHSSWHGQQTOBV-UHFFFAOYSA-N 0.000 description 1
- ZOOPONUAQQEUQX-UHFFFAOYSA-N 5-amino-2,2-dimethylpentan-1-ol Chemical compound OCC(C)(C)CCCN ZOOPONUAQQEUQX-UHFFFAOYSA-N 0.000 description 1
- WJLNNOBWGNFQCH-UHFFFAOYSA-N 5-prop-1-enoxy-1,3-benzodioxole Chemical group CC=COC1=CC=C2OCOC2=C1 WJLNNOBWGNFQCH-UHFFFAOYSA-N 0.000 description 1
- YIUIVFFUEVPRIU-UHFFFAOYSA-N 8-chlorotheophylline Chemical compound O=C1N(C)C(=O)N(C)C2=NC(Cl)=N[C]21 YIUIVFFUEVPRIU-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical group OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- RVUYFVDARIQGFE-UHFFFAOYSA-N C(#C)C1=C(OC=CC)C=CC=C1 Chemical group C(#C)C1=C(OC=CC)C=CC=C1 RVUYFVDARIQGFE-UHFFFAOYSA-N 0.000 description 1
- NYIAPPUULRVFQP-UHFFFAOYSA-N C(#N)C1=C(OC=CC)C=CC=C1 Chemical group C(#N)C1=C(OC=CC)C=CC=C1 NYIAPPUULRVFQP-UHFFFAOYSA-N 0.000 description 1
- YSSYDORKLPKEIR-UHFFFAOYSA-N C(C)OC(=O)C1=CC=C(OC(C(CC(CO)C)O)N)C=C1 Chemical compound C(C)OC(=O)C1=CC=C(OC(C(CC(CO)C)O)N)C=C1 YSSYDORKLPKEIR-UHFFFAOYSA-N 0.000 description 1
- NLSJUEIOZQCRGX-UHFFFAOYSA-N CC(CC(C(N)OC1=CC([N+]([O-])=O)=CC=C1)O)CO Chemical compound CC(CC(C(N)OC1=CC([N+]([O-])=O)=CC=C1)O)CO NLSJUEIOZQCRGX-UHFFFAOYSA-N 0.000 description 1
- ILUATABHSYELLY-UHFFFAOYSA-N CC=COC1=CC=CC(CO)=C1 Chemical group CC=COC1=CC=CC(CO)=C1 ILUATABHSYELLY-UHFFFAOYSA-N 0.000 description 1
- WBJFXNNTNXTLBP-UHFFFAOYSA-N COC(=O)C1=C(OC=CC)C=CC=C1 Chemical group COC(=O)C1=C(OC=CC)C=CC=C1 WBJFXNNTNXTLBP-UHFFFAOYSA-N 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical compound [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-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
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- 238000005642 Gabriel synthesis reaction Methods 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000001828 Gelatine Substances 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 208000010496 Heart Arrest Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- UJCZEEZOUAQXJG-UHFFFAOYSA-N OCC1=C(OC(C(CC(CO)C)O)N)C=CC=C1 Chemical compound OCC1=C(OC(C(CC(CO)C)O)N)C=CC=C1 UJCZEEZOUAQXJG-UHFFFAOYSA-N 0.000 description 1
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical class CCC ATUOYWHBWRKTHZ-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
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000001871 Tachycardia Diseases 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
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001266 acyl halides Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 229940105329 carboxymethylcellulose Drugs 0.000 description 1
- 229940096529 carboxypolymethylene Drugs 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000003218 coronary vasodilator agent Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 229940109275 cyclamate Drugs 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-O diazynium Chemical compound [NH+]#N IJGRMHOSHXDMSA-UHFFFAOYSA-O 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960005150 glycerol Drugs 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- BYXYCUABYHCYLY-UHFFFAOYSA-N isoindole-1,3-dione;potassium Chemical compound [K].C1=CC=C2C(=O)NC(=O)C2=C1 BYXYCUABYHCYLY-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000000314 lubricant Substances 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
- 229940126601 medicinal product Drugs 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- QYWYGVROYHZRFV-UHFFFAOYSA-N oxalic acid;propan-1-amine Chemical compound CCCN.OC(=O)C(O)=O QYWYGVROYHZRFV-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 229940031826 phenolate Drugs 0.000 description 1
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229940075065 polyvinyl acetate Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MTURGQJJIULABB-UHFFFAOYSA-N propan-1-amine;dihydrochloride Chemical compound Cl.Cl.CCCN MTURGQJJIULABB-UHFFFAOYSA-N 0.000 description 1
- 235000013849 propane Nutrition 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 239000003204 tranquilizing agent Substances 0.000 description 1
- 230000002936 tranquilizing effect Effects 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
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical group COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/64—Oxygen atoms
-
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (80)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702048838 DE2048838A1 (de) | 1970-10-05 | 1970-10-05 | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung |
| SE7112536*A SE383631B (sv) | 1970-10-05 | 1971-04-10 | Forfarande for framstellning av nya 1-fenoxi-2-hydroxid-3-hydroxialkylaminopropaner |
| SU1700834A SU419024A3 (ru) | 1970-10-05 | 1971-09-30 | СПОСОБ ПОЛУЧЕНИЯ 1-ФЕНОКСИ-2-ОКСИ-3-ОКСИ- АЛКИЛАМИНОПРОПАНОВ1Изобретение относитс к способу получени новых, не описанных в литературе 1-фенокси- 2-окси-З-оксиалкиламинопропанов, которые обладают фармакологической активностью и могут найти применение ,в медицине.Известен способ получени 1-изопропил- амино-2-окси-3- |
| CH424575A CH563342A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH423875A CH587223A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| IL37830A IL37830A (en) | 1970-10-05 | 1971-10-01 | Derivatives of 1-phenoxy-2-hydroxy-3-amino-propane,their preparation and pharmaceutical compositions containing them |
| CH424075A CH583686A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH424175A CH584185A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH423975A CH583685A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH1430971A CH564507A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH424375A CH563341A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH424275A CH583687A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| CH424675A CH564516A5 (en, 2012) | 1970-10-05 | 1971-10-01 | |
| PL1971174910A PL84396B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| GB4610371A GB1364280A (en) | 1970-10-05 | 1971-10-04 | 1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes an processes for their preparation |
| ZA716643A ZA716643B (en) | 1970-10-05 | 1971-10-04 | Improvements relating to 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropanes |
| PL1971174909A PL84267B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| BG20289A BG19134A3 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| PL1971174903A PL84212B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| YU2505/71A YU35576B (en) | 1970-10-05 | 1971-10-04 | Process for preparing novel 1-phenoxy-2-hydroxy-3-hydroxy alkylamino propanes |
| PH12895A PH9959A (en) | 1970-10-05 | 1971-10-04 | 1-phenoxy-2-hydroxy-3-hydroxyalkylamino-propanes and salts thereof |
| BG020287A BG20100A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-фенокси-2-хидрокси-3- хидроалкил-аминопропани |
| BG020290A BG19793A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-фенокси-2-хидрокси-3- хидроксиалкиламинопропани |
| ES395671A ES395671A1 (es) | 1970-10-05 | 1971-10-04 | Procedimiento para la preparacion de 1-fenoxi - 2 - hidroxi-3-hidroxialcohilaminopropanos. |
| BG020285A BG19133A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-фенил-2-хидрокси-3-хидроксилалкиламинопропани |
| PL1971174912A PL84276B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| JP7778571A JPS5710097B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| NO3632/71A NO132835C (en, 2012) | 1970-10-05 | 1971-10-04 | |
| BG020288A BG18858A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-фенокси-2-хидрокси-3- хидроксиалкил аминопропани |
| BG020286A BG18857A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-фенокси-2-хидрокси-3- хидроксиалкиламинопропани |
| BG018670A BG20338A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-фенокси-2-хидрокси-3- хидроксиалкил-аминопропани |
| PL1971150902A PL82037B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| BG020291A BG18859A3 (bg) | 1970-10-05 | 1971-10-04 | Метод за получаване на 1-(2-циано-4-хлорфенокси)- 2-хидрокси-3-(1,1-диметил-2-хидроксилетил)- аминопропан |
| PL1971174911A PL84227B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| PL1971174908A PL84223B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| CA124,290A CA1008866A (en) | 1970-10-05 | 1971-10-04 | 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropanes and processes for the production thereof |
| PL1971174907A PL84224B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| BE773472A BE773472A (fr) | 1970-10-05 | 1971-10-04 | Nouveaux 1-phenoxy-2-hydroxy-3-hydroxyalcoylaminopropanes et procedes pour les fabriquer |
| PL1971174905A PL84226B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| DK481671AA DK130958B (da) | 1970-10-05 | 1971-10-04 | Analogifremgangsmåde til fremstilling af racemiske eller optisk aktive 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropaner eller fysiologisk tålelige syreadditionssalte heraf. |
| FI2769/71A FI55491C (fi) | 1970-10-05 | 1971-10-04 | Analogifoerfarande foer framstaellning av racemiska eller optiskt aktiva 1-fenoxi-2-hydroxi-3-hydroxialkylaminopropaner och deras fysiologiskt laempliga syraadditionssalter |
| PL1971174906A PL84225B1 (en, 2012) | 1970-10-05 | 1971-10-04 | |
| NLAANVRAGE7113581,A NL174249C (nl) | 1970-10-05 | 1971-10-04 | Werkwijze voor het bereiden of vervaardigen van een geneesmiddel met beta-adrenolytische en bloeddrukverlagende werking dat een 1-fenoxy-2-hydroxy-3-alkylaminopropaanderivaat en/of een zuuradditiezout daarvan bevat en werkwijze voor het bereiden van een dergelijk derivaat of zuuradditiezout daarvan. |
| RO7100073333A RO62355A (fr) | 1970-10-05 | 1971-10-05 | Procede pour la preparation des 1-phenoxy-2-hydroxy-3-hydroxyalkyleaminopropanes |
| AT735073A AT318567B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| CS4618A CS172950B2 (en, 2012) | 1970-10-05 | 1971-10-05 | |
| AT734873A AT318565B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| RO7100073335A RO62357A (fr) | 1970-10-05 | 1971-10-05 | Procede pour la preparation des 1-phenoxy-2-hydroxy-3-hydroxyalkyleaminopropanes |
| IE1246/71A IE35693B1 (en) | 1970-10-05 | 1971-10-05 | 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropanes and processes for their preparation |
| AT734773A AT318564B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| RO7100073339A RO62359A (fr) | 1970-10-05 | 1971-10-05 | Procede pour la preparation des 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropanes |
| AT735473A AT318571B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze |
| RO73334A RO62356A (en, 2012) | 1970-10-05 | 1971-10-05 | |
| AT735573A AT318572B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze |
| AT734973A AT318566B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| RO73336A RO62313A (en, 2012) | 1970-10-05 | 1971-10-05 | |
| CS7034A CS172932B2 (en, 2012) | 1970-10-05 | 1971-10-05 | |
| AU34182/71A AU469119B2 (en) | 1970-10-05 | 1971-10-05 | 1-phenoxy-2-hydroxy-3-hydroxyalkyl-aminopropanes |
| RO68372A RO61540A (en, 2012) | 1970-10-05 | 1971-10-05 | |
| AT735273A AT318569B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| HUBO1319A HU163226B (en, 2012) | 1970-10-05 | 1971-10-05 | |
| AT735173A AT318568B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| AT859371A AT318561B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| RO7100073338A RO62358A (fr) | 1970-10-05 | 1971-10-05 | Procede pour la preparation des 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropanes |
| AT735373A AT318570B (de) | 1970-10-05 | 1971-10-05 | Verfahren zur Herstellung neuer 1-Phenoxy-2-hydroxy-3-hydroxyalkylaminopropane sowie deren Säureadditionssalze und Ester |
| FR7135823A FR2110230B1 (en, 2012) | 1970-10-05 | 1971-10-05 | |
| RO7100073337A RO62267A (fr) | 1970-10-05 | 1971-10-05 | Procede pour la preparation des 1-phenoxy-2-hydroxy-3-hydroxyalkylaminopropanes |
| ES399870A ES399870A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos 1-fenoxi - 2 - hidroxi - 3 - alcohilaminopropanos racemicos u opticamente activos. |
| ES399873A ES399873A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos i-fenoxi-2- idroxi-3-alcahilamino propanos recemicos u opticamenacti- vos. |
| ES399868A ES399868A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi-3-alcohilaminopropanos racemicos u opticamenteactivos. |
| ES399871A ES399871A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi-3-alcohilaminopropanos racemicos u opticamenteactivos. |
| ES399874A ES399874A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos i-fenoxi-2- hidroxi-3-alcohilamino propanos racemicos u opticamente ac- tivos. |
| ES399872A ES399872A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos i-fenoxi-2-hi- droxi-3-alcohilaminopropanos recemicos u opticamenteacti- vos. |
| ES399869A ES399869A1 (es) | 1970-10-05 | 1972-02-17 | Procedimiento para la preparacion de nuevos 1-fenoxi-2-hi- droxi-3-alcohilaminopropanos racemicos u opticamenteactivos. |
| SU731888527A SU677649A3 (ru) | 1970-10-05 | 1973-02-28 | Способ получени 1-фенокси-2-гидрокси3-гидрокси-алкиламинопропанов,их сложных эфиров или солей |
| US05/451,820 US3959338A (en) | 1970-10-05 | 1974-03-18 | 1-(Cyano-phenoxy)-2-hydroxy-3-hydroxyalkylamino-propanes and salts thereof |
| CH414475A CH564515A5 (en, 2012) | 1970-10-05 | 1975-04-03 | |
| US05/652,113 US4025646A (en) | 1970-10-05 | 1976-01-26 | Pharmaceutical compositions containing a 1-(cyano-phenoxy)-2-hydroxy-3-hydroxyalkylamino-propane and method of use |
| CH1430971A CH587227A5 (en, 2012) | 1970-10-05 | 1976-12-06 | |
| YU236/79A YU35577B (en) | 1970-10-05 | 1979-02-02 | Process for preparing novel 1-phenoxy-2-hydroxy-3-hydroxy alkylamino propanes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702048838 DE2048838A1 (de) | 1970-10-05 | 1970-10-05 | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2048838A1 true DE2048838A1 (de) | 1972-04-06 |
Family
ID=5784228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702048838 Withdrawn DE2048838A1 (de) | 1970-10-05 | 1970-10-05 | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung |
Country Status (26)
| Country | Link |
|---|---|
| JP (1) | JPS5710097B1 (en, 2012) |
| AT (10) | AT318571B (en, 2012) |
| AU (1) | AU469119B2 (en, 2012) |
| BE (1) | BE773472A (en, 2012) |
| BG (8) | BG19133A3 (en, 2012) |
| CA (1) | CA1008866A (en, 2012) |
| CH (11) | CH583686A5 (en, 2012) |
| CS (2) | CS172950B2 (en, 2012) |
| DE (1) | DE2048838A1 (en, 2012) |
| DK (1) | DK130958B (en, 2012) |
| ES (8) | ES395671A1 (en, 2012) |
| FI (1) | FI55491C (en, 2012) |
| FR (1) | FR2110230B1 (en, 2012) |
| GB (1) | GB1364280A (en, 2012) |
| HU (1) | HU163226B (en, 2012) |
| IE (1) | IE35693B1 (en, 2012) |
| IL (1) | IL37830A (en, 2012) |
| NL (1) | NL174249C (en, 2012) |
| NO (1) | NO132835C (en, 2012) |
| PH (1) | PH9959A (en, 2012) |
| PL (10) | PL84225B1 (en, 2012) |
| RO (8) | RO62357A (en, 2012) |
| SE (1) | SE383631B (en, 2012) |
| SU (2) | SU419024A3 (en, 2012) |
| YU (2) | YU35576B (en, 2012) |
| ZA (1) | ZA716643B (en, 2012) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055658A (en) * | 1976-05-17 | 1977-10-25 | Mead Johnson & Company | Cyanomethylphenethanolamines |
| US4454154A (en) * | 1981-06-23 | 1984-06-12 | American Hospital Supply Corporation | Method for treating glaucoma by the topical administration of selectively metabolized beta-blocking agents |
| DE3248835A1 (de) * | 1981-06-23 | 1983-06-30 | American Hospital Supply Corp | Zusammensetzungen fuer die behandlung von glaukom |
| US4652584A (en) * | 1984-07-13 | 1987-03-24 | Mcneilab, Inc. | Acetylenic phenoxypropanol derivatives and pharmaceutical compositions for the treatment of hypertension |
| DE4422707A1 (de) * | 1994-06-29 | 1996-01-04 | Hoechst Ag | Verfahren zum Färben aminierter Cellulose-/Polyester-Mischgewebe mit faserreaktiven Dispersionsfarbstoffen |
| JP4934287B2 (ja) * | 2005-04-05 | 2012-05-16 | 花王株式会社 | 美白剤 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD45360A (en, 2012) * | ||||
| DE2007751A1 (en, 2012) * | 1969-02-21 | 1970-09-10 |
-
1970
- 1970-10-05 DE DE19702048838 patent/DE2048838A1/de not_active Withdrawn
-
1971
- 1971-04-10 SE SE7112536*A patent/SE383631B/xx unknown
- 1971-09-30 SU SU1700834A patent/SU419024A3/ru active
- 1971-10-01 CH CH424075A patent/CH583686A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH423875A patent/CH587223A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424275A patent/CH583687A5/xx not_active IP Right Cessation
- 1971-10-01 IL IL37830A patent/IL37830A/xx unknown
- 1971-10-01 CH CH424175A patent/CH584185A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH1430971A patent/CH564507A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH423975A patent/CH583685A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424675A patent/CH564516A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424575A patent/CH563342A5/xx not_active IP Right Cessation
- 1971-10-01 CH CH424375A patent/CH563341A5/xx not_active IP Right Cessation
- 1971-10-04 BG BG020285A patent/BG19133A3/xx unknown
- 1971-10-04 CA CA124,290A patent/CA1008866A/en not_active Expired
- 1971-10-04 ZA ZA716643A patent/ZA716643B/xx unknown
- 1971-10-04 BE BE773472A patent/BE773472A/xx not_active IP Right Cessation
- 1971-10-04 NO NO3632/71A patent/NO132835C/no unknown
- 1971-10-04 PL PL1971174906A patent/PL84225B1/pl unknown
- 1971-10-04 PL PL1971174905A patent/PL84226B1/pl unknown
- 1971-10-04 PL PL1971174908A patent/PL84223B1/pl unknown
- 1971-10-04 YU YU2505/71A patent/YU35576B/xx unknown
- 1971-10-04 BG BG20289A patent/BG19134A3/xx unknown
- 1971-10-04 BG BG020286A patent/BG18857A3/xx unknown
- 1971-10-04 BG BG020287A patent/BG20100A3/xx unknown
- 1971-10-04 PL PL1971174910A patent/PL84396B1/pl unknown
- 1971-10-04 DK DK481671AA patent/DK130958B/da not_active IP Right Cessation
- 1971-10-04 GB GB4610371A patent/GB1364280A/en not_active Expired
- 1971-10-04 BG BG020288A patent/BG18858A3/xx unknown
- 1971-10-04 PL PL1971174909A patent/PL84267B1/pl unknown
- 1971-10-04 PL PL1971174907A patent/PL84224B1/pl unknown
- 1971-10-04 JP JP7778571A patent/JPS5710097B1/ja active Pending
- 1971-10-04 FI FI2769/71A patent/FI55491C/fi active
- 1971-10-04 BG BG020291A patent/BG18859A3/xx unknown
- 1971-10-04 BG BG018670A patent/BG20338A3/xx unknown
- 1971-10-04 PL PL1971174911A patent/PL84227B1/pl unknown
- 1971-10-04 ES ES395671A patent/ES395671A1/es not_active Expired
- 1971-10-04 BG BG020290A patent/BG19793A3/xx unknown
- 1971-10-04 PL PL1971174912A patent/PL84276B1/pl unknown
- 1971-10-04 PL PL1971174903A patent/PL84212B1/pl unknown
- 1971-10-04 PL PL1971150902A patent/PL82037B1/pl unknown
- 1971-10-04 PH PH12895A patent/PH9959A/en unknown
- 1971-10-04 NL NLAANVRAGE7113581,A patent/NL174249C/xx not_active IP Right Cessation
- 1971-10-05 AT AT735473A patent/AT318571B/de not_active IP Right Cessation
- 1971-10-05 FR FR7135823A patent/FR2110230B1/fr not_active Expired
- 1971-10-05 RO RO7100073335A patent/RO62357A/ro unknown
- 1971-10-05 AT AT734873A patent/AT318565B/de not_active IP Right Cessation
- 1971-10-05 CS CS4618A patent/CS172950B2/cs unknown
- 1971-10-05 RO RO73336A patent/RO62313A/ro unknown
- 1971-10-05 AT AT734773A patent/AT318564B/de not_active IP Right Cessation
- 1971-10-05 RO RO7100073338A patent/RO62358A/ro unknown
- 1971-10-05 HU HUBO1319A patent/HU163226B/hu unknown
- 1971-10-05 RO RO68372A patent/RO61540A/ro unknown
- 1971-10-05 AT AT735573A patent/AT318572B/de not_active IP Right Cessation
- 1971-10-05 RO RO73334A patent/RO62356A/ro unknown
- 1971-10-05 AU AU34182/71A patent/AU469119B2/en not_active Expired
- 1971-10-05 AT AT735073A patent/AT318567B/de not_active IP Right Cessation
- 1971-10-05 AT AT735373A patent/AT318570B/de not_active IP Right Cessation
- 1971-10-05 CS CS7034A patent/CS172932B2/cs unknown
- 1971-10-05 AT AT735173A patent/AT318568B/de not_active IP Right Cessation
- 1971-10-05 RO RO7100073333A patent/RO62355A/ro unknown
- 1971-10-05 RO RO7100073337A patent/RO62267A/ro unknown
- 1971-10-05 AT AT735273A patent/AT318569B/de not_active IP Right Cessation
- 1971-10-05 RO RO7100073339A patent/RO62359A/ro unknown
- 1971-10-05 AT AT734973A patent/AT318566B/de not_active IP Right Cessation
- 1971-10-05 IE IE1246/71A patent/IE35693B1/xx unknown
- 1971-10-05 AT AT859371A patent/AT318561B/de not_active IP Right Cessation
-
1972
- 1972-02-17 ES ES399873A patent/ES399873A1/es not_active Expired
- 1972-02-17 ES ES399870A patent/ES399870A1/es not_active Expired
- 1972-02-17 ES ES399872A patent/ES399872A1/es not_active Expired
- 1972-02-17 ES ES399874A patent/ES399874A1/es not_active Expired
- 1972-02-17 ES ES399871A patent/ES399871A1/es not_active Expired
- 1972-02-17 ES ES399869A patent/ES399869A1/es not_active Expired
- 1972-02-17 ES ES399868A patent/ES399868A1/es not_active Expired
-
1973
- 1973-02-28 SU SU731888527A patent/SU677649A3/ru active
-
1975
- 1975-04-03 CH CH414475A patent/CH564515A5/xx not_active IP Right Cessation
-
1976
- 1976-12-06 CH CH1430971A patent/CH587227A5/xx not_active IP Right Cessation
-
1979
- 1979-02-02 YU YU236/79A patent/YU35577B/xx unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD45360A (en, 2012) * | ||||
| DE2007751A1 (en, 2012) * | 1969-02-21 | 1970-09-10 |
Non-Patent Citations (1)
| Title |
|---|
| J.Med.Chem., 12, 1969, S. 641 * |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2645710A1 (de) | Phenoxy-amino-propanole und verfahren zu ihrer herstellung | |
| DE1643262A1 (de) | Neue 1-Phenoxy-2-hydroxy-3-alkylaminopropane und Verfahren zu ihrer Herstellung | |
| DE1937477A1 (de) | Neue 1-Phenoxy-2-hydroxy-3-cycloalkylaminopropane und Verfahren zu ihrer Herstellung | |
| DD201305A5 (de) | Verfahren zur herstellung von in 7-stellung substituierten benzopyranen | |
| DE3026534A1 (de) | 3,1-benzoxazin-2-one, ihre herstellung und verwendung | |
| EP0025192A2 (de) | Substituierte Oxirancarbonsäuren, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende Arzneimittel | |
| EP0039771B1 (de) | Cyclopropanderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung | |
| DE2048838A1 (de) | Neue 1 Phenoxy 2 hydroxy 3 hydroxyal kylaminopropane und Verfahren zu ihrer Her stellung | |
| DE3320394A1 (de) | Optisch aktive n-arylierte oxazolidinon-(2)-derivate, deren verwendung als spezifische und reversible inhibitoren von monoaminooxydase des b-typs sowie verfahren zu deren herstellung | |
| DE3242344A1 (de) | Neue alkylendiaminoderivate, ihre herstellung und diese verbindungen enthaltende arzneimittel | |
| DE1940566A1 (de) | 1-(2-Nitrilophenoxy)-2-hydroxy-3-aethylaminopropan und dessen Salze | |
| EP0011747B1 (de) | Aminopropanolderivate des 6-Hydroxy-2,3,4,5-tetrahydro-1H-1-benzazepin-2-ons, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Zubereitungen | |
| DE1593762A1 (de) | Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen | |
| EP0038936B1 (de) | Neue 1-Aryloxy-3-alkylamino-2-propanole und Verfahren zu ihrer Herstellung | |
| DE2814168A1 (de) | Neue 1- eckige klammer auf 3-(3,4,5- trimethoxyphenoxy)-2-hydroxypropyl eckige klammer zu -4-aryl-piperazin-derivate und verfahren zu ihrer herstellung | |
| DE2309887C2 (de) | 1-Aryloxy-2-hydroxy-3-alkinylaminopropan-Derivate und deren physiologisch verträgliche Säureadditionssalze, pharmazeutische Präparate und Herstellungsverfahren für die Verbindungen | |
| DE2421165A1 (de) | N-substituierte dihydroxyphenylaethylamine | |
| DE2403809C2 (de) | 1-Aryloxy-2-hydroxy-3-alkinylaminopropane und Verfahren zu ihrer Herstellung und pharmazeutische Präparate | |
| EP0035733B1 (de) | Neue 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-aminopropane und Verfahren zu ihrer Herstellung | |
| DE2324584A1 (de) | Neue amine und verfahren zu ihrer herstellung | |
| EP0035734B1 (de) | Neue 1-(Acylamino-aryloxy-)2-hydroxy-3-alkinyl-aminopropane und Verfahren zu ihrer Herstellung | |
| DE1593782A1 (de) | Neue nitrilsubstituierte 1-Phenoxy-2-hydroxy-3-tert.-butylaminopropane und Verfahren zu ihrer Herstellung | |
| DE2944222A1 (de) | Neue aminoderivate des 1,2-benzisothiazols | |
| DE2239606A1 (de) | 4-phenoxy 3-hydroxy-butyramidine und derivate | |
| EP0031910B1 (de) | Anilinderivate, diese enthaltende pharmazeutische Zubereitungen und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8178 | Suspension cancelled | ||
| 8130 | Withdrawal |