DK141935B - Analogifremgangsmåde til fremstilling af aryloxyaminobutanoler eller deres stereoisomere eller syreadditionssalte deraf. - Google Patents
Analogifremgangsmåde til fremstilling af aryloxyaminobutanoler eller deres stereoisomere eller syreadditionssalte deraf. Download PDFInfo
- Publication number
- DK141935B DK141935B DK60875AA DK60875A DK141935B DK 141935 B DK141935 B DK 141935B DK 60875A A DK60875A A DK 60875AA DK 60875 A DK60875 A DK 60875A DK 141935 B DK141935 B DK 141935B
- Authority
- DK
- Denmark
- Prior art keywords
- compounds
- general formula
- hydroxy
- group
- carbon atoms
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 8
- 239000002253 acid Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 48
- 238000000034 method Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- -1 nitro-substituted phenyl group Chemical group 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- 239000000203 mixture Substances 0.000 description 16
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 10
- 239000011976 maleic acid Substances 0.000 description 10
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 229910000033 sodium borohydride Inorganic materials 0.000 description 9
- 239000012279 sodium borohydride Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- DURULFYMVIFBIR-UHFFFAOYSA-N practolol Chemical compound CC(C)NCC(O)COC1=CC=C(NC(C)=O)C=C1 DURULFYMVIFBIR-UHFFFAOYSA-N 0.000 description 8
- 239000013558 reference substance Substances 0.000 description 7
- 208000009079 Bronchial Spasm Diseases 0.000 description 6
- 208000014181 Bronchial disease Diseases 0.000 description 6
- 206010006482 Bronchospasm Diseases 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229960003712 propranolol Drugs 0.000 description 6
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 5
- LVFKCUIDAJFWBY-UHFFFAOYSA-N 4-amino-1-naphthalen-1-yloxybutan-2-ol Chemical compound C1=CC=C2C(OCC(O)CCN)=CC=CC2=C1 LVFKCUIDAJFWBY-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229960001749 practolol Drugs 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- SCSDWHLOEXNMJE-BTJKTKAUSA-N (z)-but-2-enedioic acid;4-(cyclohexylamino)-1-naphthalen-1-yloxybutan-2-ol Chemical compound OC(=O)\C=C/C(O)=O.C=1C=CC2=CC=CC=C2C=1OCC(O)CCNC1CCCCC1 SCSDWHLOEXNMJE-BTJKTKAUSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 206010003119 arrhythmia Diseases 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 3
- HLPYFDDNEAROPY-UHFFFAOYSA-N 4-amino-1-phenoxybutan-2-ol Chemical compound NCCC(O)COC1=CC=CC=C1 HLPYFDDNEAROPY-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- 241000700198 Cavia Species 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 229960001340 histamine Drugs 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229940095990 inderal Drugs 0.000 description 3
- 230000000053 inderal effect Effects 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- OBAGDHZPZLEISV-TXZACQIRSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-5,14-dihydroxy-3-[(4r,6r)-4-methoxy-6-methyl-5-[(1s,2s,3r,4s,5s)-2,3,4-trihydroxy-5-(hydroxymethyl)cyclohexyl]oxyoxan-2-yl]oxy-8,9,13-trimethyl-17-(5-oxo-2h-furan-3-yl)-2,3,4,6,7,11,12,15,16,17-decahydro-1h-cyclopenta[a]phena Chemical compound C1([C@H]2CC[C@@]3(O)[C@]4(C)CC[C@]5([C@]([C@]4(CC[C@@]32C)C)(C=O)CC[C@@H](C5)OC2C[C@H](C([C@@H](C)O2)O[C@@H]2[C@H]([C@H](O)[C@@H](O)[C@H](CO)C2)O)OC)O)=CC(=O)OC1 OBAGDHZPZLEISV-TXZACQIRSA-N 0.000 description 2
- LCFBGNXJJRJTSX-UHFFFAOYSA-N 4-amino-1-(2,3-dichlorophenoxy)butan-2-ol Chemical compound ClC1=C(OCC(CCN)O)C=CC=C1Cl LCFBGNXJJRJTSX-UHFFFAOYSA-N 0.000 description 2
- YBYYFFPWZCKVDN-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.C1(=CC=CC2=CC=CC=C12)OCC(CCNC(C)C)O Chemical compound C(C=C/C(=O)O)(=O)O.C1(=CC=CC2=CC=CC=C12)OCC(CCNC(C)C)O YBYYFFPWZCKVDN-UHFFFAOYSA-N 0.000 description 2
- CVXSWGCTAFPKNU-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.ClC1=C(OCC(CCNC(C)C)O)C=CC=C1Cl Chemical compound C(C=C/C(=O)O)(=O)O.ClC1=C(OCC(CCNC(C)C)O)C=CC=C1Cl CVXSWGCTAFPKNU-UHFFFAOYSA-N 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000000219 Sympatholytic Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000002057 chronotropic effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000297 inotrophic effect Effects 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 239000003791 organic solvent mixture Substances 0.000 description 2
- 229960004570 oxprenolol Drugs 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical compound CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 description 2
- 229910052697 platinum Inorganic materials 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-UHFFFAOYSA-N 2-bromopropane Chemical compound CC(C)Br NAMYKGVDVNBCFQ-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- MYZWSRUOOJLLNM-UHFFFAOYSA-N 4-(2,3-dichlorophenoxy)-3-hydroxybutanenitrile Chemical compound N#CCC(O)COC1=CC=CC(Cl)=C1Cl MYZWSRUOOJLLNM-UHFFFAOYSA-N 0.000 description 1
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- RLDGXGJNGNAFMN-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.O(C1=CC=CC=C1)CC(CCNC1CCCCC1)O Chemical compound C(C=C/C(=O)O)(=O)O.O(C1=CC=CC=C1)CC(CCNC1CCCCC1)O RLDGXGJNGNAFMN-UHFFFAOYSA-N 0.000 description 1
- IRLYOIJLBQQILQ-BTJKTKAUSA-N C(\C=C/C(=O)O)(=O)O.C1(=CC=C(C=C1)OCC(CCNC1CCCCC1)O)C Chemical compound C(\C=C/C(=O)O)(=O)O.C1(=CC=C(C=C1)OCC(CCNC1CCCCC1)O)C IRLYOIJLBQQILQ-BTJKTKAUSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033799 Paralysis Diseases 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241000287181 Sturnus vulgaris Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XFSBVAOIAHNAPC-NPVHKAFCSA-N aconitin Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45[C@H]6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-NPVHKAFCSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical group 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000740 bleeding effect Effects 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 210000000621 bronchi Anatomy 0.000 description 1
- PVUZZTZATFQPBK-BTJKTKAUSA-N butylazanium;(z)-4-hydroxy-4-oxobut-2-enoate Chemical compound CCCC[NH3+].OC(=O)\C=C/C([O-])=O PVUZZTZATFQPBK-BTJKTKAUSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 231100000640 hair analysis Toxicity 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
- C07C217/32—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted
- C07C217/34—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring the six-membered aromatic ring or condensed ring system containing that ring being further substituted by halogen atoms, by trihalomethyl, nitro or nitroso groups, or by singly-bound oxygen atoms
-
- 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
- A61K31/138—Aryloxyalkylamines, e.g. propranolol, tamoxifen, phenoxybenzamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/52—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups or amino groups bound to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUCI001449 | 1974-02-20 | ||
HUCI1449A HU169464B (is") | 1974-02-20 | 1974-02-20 |
Publications (3)
Publication Number | Publication Date |
---|---|
DK60875A DK60875A (is") | 1975-10-20 |
DK141935B true DK141935B (da) | 1980-07-21 |
DK141935C DK141935C (is") | 1980-12-08 |
Family
ID=10994508
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DK60875AA DK141935B (da) | 1974-02-20 | 1975-02-19 | Analogifremgangsmåde til fremstilling af aryloxyaminobutanoler eller deres stereoisomere eller syreadditionssalte deraf. |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS5929063B2 (is") |
AT (1) | AT339281B (is") |
BE (1) | BE825745A (is") |
BG (2) | BG26366A3 (is") |
CA (1) | CA1074338A (is") |
CH (1) | CH619684A5 (is") |
CS (1) | CS199578B2 (is") |
DD (1) | DD119414A5 (is") |
DE (1) | DE2506355C2 (is") |
DK (1) | DK141935B (is") |
ES (2) | ES434784A1 (is") |
FI (1) | FI61304C (is") |
FR (1) | FR2261001B1 (is") |
GB (1) | GB1457086A (is") |
HU (1) | HU169464B (is") |
IL (1) | IL46634A (is") |
NL (1) | NL182698C (is") |
NO (1) | NO141754C (is") |
PL (2) | PL99025B1 (is") |
SE (1) | SE433935B (is") |
SU (1) | SU1025327A3 (is") |
YU (2) | YU36916B (is") |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK154288B (da) * | 1974-10-25 | 1988-10-31 | Robins Co Inc A H | Analogifremgangsmaade til fremstilling af 1-aryloxy-4-amino-2-butanoler |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0097000B1 (en) * | 1982-06-10 | 1987-09-09 | Beecham Wuelfing GmbH & Co KG | Amine derivatives |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
SE368197B (is") * | 1968-11-18 | 1974-06-24 | Pfizer | |
GB1245148A (en) * | 1968-11-18 | 1971-09-08 | Pfizer Ltd | Propanolamine derivatives |
SE384853B (sv) * | 1972-04-04 | 1976-05-24 | Haessle Ab | Forfarande for framstellning av nya aminer |
AT305245B (de) * | 1969-09-24 | 1973-02-12 | Ici Ltd | Verfahren zur Herstellung von neuen substituierten 1-Phenoxy-2-hydroxy-3-alkylaminopropanen und von deren Säureadditionssalzen |
-
1974
- 1974-02-20 HU HUCI1449A patent/HU169464B/hu unknown
-
1975
- 1975-02-14 DE DE2506355A patent/DE2506355C2/de not_active Expired
- 1975-02-14 IL IL46634A patent/IL46634A/xx unknown
- 1975-02-17 AT AT114075A patent/AT339281B/de not_active IP Right Cessation
- 1975-02-17 DD DD184260A patent/DD119414A5/xx unknown
- 1975-02-17 ES ES434784A patent/ES434784A1/es not_active Expired
- 1975-02-18 BG BG029004A patent/BG26366A3/xx unknown
- 1975-02-18 FR FR7504961A patent/FR2261001B1/fr not_active Expired
- 1975-02-18 FI FI750443A patent/FI61304C/fi not_active IP Right Cessation
- 1975-02-18 BG BG030300A patent/BG26367A4/xx unknown
- 1975-02-18 SE SE7501801A patent/SE433935B/xx not_active IP Right Cessation
- 1975-02-18 YU YU0373/75A patent/YU36916B/xx unknown
- 1975-02-19 PL PL1975193962A patent/PL99025B1/pl unknown
- 1975-02-19 DK DK60875AA patent/DK141935B/da not_active IP Right Cessation
- 1975-02-19 CA CA220,429A patent/CA1074338A/en not_active Expired
- 1975-02-19 PL PL1975178154A patent/PL99023B1/pl unknown
- 1975-02-19 NL NLAANVRAGE7501951,A patent/NL182698C/xx not_active IP Right Cessation
- 1975-02-19 NO NO750566A patent/NO141754C/no unknown
- 1975-02-19 GB GB705075A patent/GB1457086A/en not_active Expired
- 1975-02-19 SU SU752108001A patent/SU1025327A3/ru active
- 1975-02-19 CH CH206475A patent/CH619684A5/de not_active IP Right Cessation
- 1975-02-20 JP JP50020452A patent/JPS5929063B2/ja not_active Expired
- 1975-02-20 BE BE153530A patent/BE825745A/xx not_active IP Right Cessation
- 1975-02-20 CS CS751129A patent/CS199578B2/cs unknown
-
1976
- 1976-11-15 ES ES453326A patent/ES453326A1/es not_active Expired
-
1981
- 1981-07-08 YU YU1676/81A patent/YU37116B/xx unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DK154288B (da) * | 1974-10-25 | 1988-10-31 | Robins Co Inc A H | Analogifremgangsmaade til fremstilling af 1-aryloxy-4-amino-2-butanoler |
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US4081447A (en) | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof | |
NO143046B (no) | Innretning for renskjaering av frukt og groennsaker | |
US3974156A (en) | 2-(Substituted anilino) methylmorpholine compounds | |
EP0004532A1 (de) | 1-Aryloxy-3-nitratoalkylamino-2-propanole, Verfahren zu ihrer Herstellung und ihre pharmazeutischen Zubereitungen | |
DE3881842T2 (de) | Substituierte alkylamin-derivate. | |
HU184359B (en) | Process for preparing substituted acyl-carbamides | |
DK141935B (da) | Analogifremgangsmåde til fremstilling af aryloxyaminobutanoler eller deres stereoisomere eller syreadditionssalte deraf. | |
US3255249A (en) | 2-branched lower alkyl-amino-1-(indan-, hydrogenated indan- and hydrogenated naphth-2-yl) lower alkanols | |
Casadio et al. | Synthesis and pharmacological properties of N-derivatives of 5, 6-dihydro-7H, 12H-dibenz [c, f] azocine, a new tricyclic system | |
JPS6360750B2 (is") | ||
IE59151B1 (en) | New derivatives of 4-phenylpropyl indole and their salts, their preparation process, their use as medicaments and the pharmaceutical compositions containing them | |
DE2409313A1 (de) | Neue pyrrolyl-verbindungen und verfahren zu ihrer herstellung | |
JPS5821624B2 (ja) | 3 カンジフエニルアミン − ユウドウタイノ セイホウ | |
NO142103B (no) | Soppdrepende middel for anvendelse i og paa landbruksprodukter | |
FI85465B (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-fenylpropyl-indolderivat. | |
DE2324584A1 (de) | Neue amine und verfahren zu ihrer herstellung | |
NO164771B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive aminopropanolderivater. | |
US3989844A (en) | Basic oximes and their preparation | |
NO800660L (no) | Fremgangsmaate for fremstilling av piperidinderivater | |
CS199579B2 (cs) | Způsob výroby nových aryloxyamlnobntanolů, Jejich stereoisomerů a netoxických adičních solí s kyselinami | |
NO843906L (no) | Nye 1-(alkyl-hydroksy-fenyl)-1-hydroksy-2-(alkylamino)-propaner | |
DD153682A1 (de) | Verfahren zur herstellung neuer alkanolamine | |
DK144299B (da) | Analogifremgangsmaade til fremstilling af 1-fenyl2-amino-1,3-propandiol-n-alkyl-derivater eller fysiologisk acceptable salte deraf | |
SU741796A3 (ru) | Способ получени замещенных - 2-(фурил-2)-этил -пропиниламина или их солей,или их оптических изомеров | |
CH581654A5 (en) | 1,10-trimethylene-8-methyl-tetrahydropyrazin - anti-depressant |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PBP | Patent lapsed |