CS199578B2 - Process for preparing new aryloxyaminobutanoles,stereoisomers thereof and non-toxic additive salts with acids - Google Patents
Process for preparing new aryloxyaminobutanoles,stereoisomers thereof and non-toxic additive salts with acids Download PDFInfo
- Publication number
- CS199578B2 CS199578B2 CS751129A CS112975A CS199578B2 CS 199578 B2 CS199578 B2 CS 199578B2 CS 751129 A CS751129 A CS 751129A CS 112975 A CS112975 A CS 112975A CS 199578 B2 CS199578 B2 CS 199578B2
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- Czechoslovakia
- Prior art keywords
- compounds
- general formula
- formula
- hydroxy
- stereoisomers
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 14
- 231100000252 nontoxic Toxicity 0.000 title claims abstract description 10
- 230000003000 nontoxic effect Effects 0.000 title claims abstract description 10
- 239000002253 acid Substances 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000007513 acids Chemical class 0.000 title 1
- 239000000654 additive Substances 0.000 title 1
- 230000000996 additive effect Effects 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 41
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 230000009467 reduction Effects 0.000 claims description 7
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000004344 phenylpropyl group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 abstract description 2
- 239000007858 starting material Substances 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000002876 beta blocker Substances 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 14
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol hydrochloride Natural products C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N chloroform Substances ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 9
- 239000011976 maleic acid Substances 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 229910000033 sodium borohydride Inorganic materials 0.000 description 8
- 239000012279 sodium borohydride Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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 7
- 239000013558 reference substance Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CEMAWMOMDPGJMB-UHFFFAOYSA-N (+-)-Oxprenolol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1OCC=C CEMAWMOMDPGJMB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 206010010904 Convulsion Diseases 0.000 description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229960001749 practolol Drugs 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 229960003712 propranolol Drugs 0.000 description 5
- 125000005978 1-naphthyloxy group Chemical group 0.000 description 4
- -1 3- (1-naphthyloxy) -3-hydroxybutyric acid nitrile Chemical class 0.000 description 4
- 239000007868 Raney catalyst Substances 0.000 description 4
- 229910000564 Raney nickel Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 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 3
- 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 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 239000002262 Schiff base Substances 0.000 description 3
- 150000004753 Schiff bases Chemical class 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 230000006793 arrhythmia Effects 0.000 description 3
- 206010003119 arrhythmia Diseases 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
- 230000036461 convulsion Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000002474 experimental method 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
- 229960004570 oxprenolol Drugs 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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
- 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
- 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 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 239000000219 Sympatholytic Substances 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 230000000747 cardiac effect Effects 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
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229940095990 inderal Drugs 0.000 description 2
- 230000000053 inderal effect Effects 0.000 description 2
- 230000000297 inotrophic effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- OKRJGUKZYSEUOY-UHFFFAOYSA-N n-propan-2-ylbutan-1-amine Chemical compound CCCCNC(C)C OKRJGUKZYSEUOY-UHFFFAOYSA-N 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
- 239000007787 solid Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MEAPRSDUXBHXGD-UHFFFAOYSA-N 3-chloro-n-(4-propan-2-ylphenyl)propanamide Chemical compound CC(C)C1=CC=C(NC(=O)CCCl)C=C1 MEAPRSDUXBHXGD-UHFFFAOYSA-N 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
- POGMHKKITHUWJG-UHFFFAOYSA-N 4-amino-1-(4-methylphenoxy)butan-2-ol Chemical compound CC1=CC=C(OCC(O)CCN)C=C1 POGMHKKITHUWJG-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
- 208000009079 Bronchial Spasm Diseases 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- MMIAEARGZOTOMA-UHFFFAOYSA-N C(C=C/C(=O)O)(=O)O.O(C1=CC=CC=C1)C(C(CCC(CC1=CC=CC=C1)C)O)N Chemical compound C(C=C/C(=O)O)(=O)O.O(C1=CC=CC=C1)C(C(CCC(CC1=CC=CC=C1)C)O)N MMIAEARGZOTOMA-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
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 235000019759 Maize starch Nutrition 0.000 description 1
- 241000699670 Mus sp. Species 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
- 230000001133 acceleration Effects 0.000 description 1
- 229960001413 acetanilide Drugs 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
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- LHMHCLYDBQOYTO-UHFFFAOYSA-N bromofluoromethane Chemical compound FCBr LHMHCLYDBQOYTO-UHFFFAOYSA-N 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
- KMQAPZBMEMMKSS-UHFFFAOYSA-K calcium;magnesium;phosphate Chemical compound [Mg+2].[Ca+2].[O-]P([O-])([O-])=O KMQAPZBMEMMKSS-UHFFFAOYSA-K 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 239000012043 crude product Substances 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
- 230000000994 depressogenic effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940039009 isoproterenol Drugs 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229960001834 oxprenolol hydrochloride Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 230000004526 pharmaceutical effect Effects 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZMRUPTIKESYGQW-UHFFFAOYSA-N propranolol hydrochloride Chemical compound [H+].[Cl-].C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 ZMRUPTIKESYGQW-UHFFFAOYSA-N 0.000 description 1
- 229960004604 propranolol hydrochloride Drugs 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
- 238000011160 research Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000036387 respiratory rate Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000000948 sympatholitic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 238000005303 weighing 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)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (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)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CS774232A CS199579B2 (cs) | 1974-02-20 | 1977-06-27 | Způsob výroby nových aryloxyamlnobntanolů, Jejich stereoisomerů a netoxických adičních solí s kyselinami |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
HUCI1449A HU169464B (is") | 1974-02-20 | 1974-02-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CS199578B2 true CS199578B2 (en) | 1980-07-31 |
Family
ID=10994508
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CS751129A CS199578B2 (en) | 1974-02-20 | 1975-02-20 | Process for preparing new aryloxyaminobutanoles,stereoisomers thereof and non-toxic additive salts with acids |
Country Status (22)
Country | Link |
---|---|
JP (1) | JPS5929063B2 (is") |
AT (1) | AT339281B (is") |
BE (1) | BE825745A (is") |
BG (2) | BG26367A4 (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") |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL48309A (en) * | 1974-10-25 | 1980-01-31 | Robins Co Inc A H | 1-aryloxy-4-amino-2-butanols and pharmaceutical compositions containing them |
DE3373466D1 (de) * | 1982-06-10 | 1987-10-15 | Beecham Wuelfing Gmbh & Co Kg | Amine derivatives |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1245148A (en) * | 1968-11-18 | 1971-09-08 | Pfizer Ltd | Propanolamine derivatives |
ES373606A1 (es) * | 1968-11-18 | 1972-06-01 | Pfizer | Un procedimiento para la preparacion de nuevos derivados depropanolamina. |
SE384853B (sv) * | 1972-04-04 | 1976-05-24 | Haessle Ab | Forfarande for framstellning av nya aminer |
CH561174A5 (is") * | 1969-09-24 | 1975-04-30 | Ici Ltd |
-
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 ES ES434784A patent/ES434784A1/es not_active Expired
- 1975-02-17 DD DD184260A patent/DD119414A5/xx unknown
- 1975-02-17 AT AT114075A patent/AT339281B/de not_active IP Right Cessation
- 1975-02-18 YU YU0373/75A patent/YU36916B/xx unknown
- 1975-02-18 BG BG030300A patent/BG26367A4/xx unknown
- 1975-02-18 FI FI750443A patent/FI61304C/fi not_active IP Right Cessation
- 1975-02-18 FR FR7504961A patent/FR2261001B1/fr not_active Expired
- 1975-02-18 BG BG029004A patent/BG26366A3/xx unknown
- 1975-02-18 SE SE7501801A patent/SE433935B/xx not_active IP Right Cessation
- 1975-02-19 SU SU752108001A patent/SU1025327A3/ru active
- 1975-02-19 DK DK60875AA patent/DK141935B/da not_active IP Right Cessation
- 1975-02-19 NL NLAANVRAGE7501951,A patent/NL182698C/xx not_active IP Right Cessation
- 1975-02-19 GB GB705075A patent/GB1457086A/en not_active Expired
- 1975-02-19 CH CH206475A patent/CH619684A5/de not_active IP Right Cessation
- 1975-02-19 CA CA220,429A patent/CA1074338A/en not_active Expired
- 1975-02-19 NO NO750566A patent/NO141754C/no unknown
- 1975-02-19 PL PL1975193962A patent/PL99025B1/pl unknown
- 1975-02-19 PL PL1975178154A patent/PL99023B1/pl unknown
- 1975-02-20 CS CS751129A patent/CS199578B2/cs unknown
- 1975-02-20 JP JP50020452A patent/JPS5929063B2/ja not_active Expired
- 1975-02-20 BE BE153530A patent/BE825745A/xx not_active IP Right Cessation
-
1976
- 1976-11-15 ES ES453326A patent/ES453326A1/es not_active Expired
-
1981
- 1981-07-08 YU YU1676/81A patent/YU37116B/xx unknown
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