NO126014B - - Google Patents
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- Publication number
- NO126014B NO126014B NO169835A NO16983567A NO126014B NO 126014 B NO126014 B NO 126014B NO 169835 A NO169835 A NO 169835A NO 16983567 A NO16983567 A NO 16983567A NO 126014 B NO126014 B NO 126014B
- Authority
- NO
- Norway
- Prior art keywords
- alpha
- group
- hydroxy
- solution
- hydrogen
- Prior art date
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 132
- -1 methylmagnesium halide Chemical class 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 60
- 229910052739 hydrogen Inorganic materials 0.000 claims description 43
- 239000001257 hydrogen Substances 0.000 claims description 43
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 39
- 230000002829 reductive effect Effects 0.000 claims description 34
- 238000002360 preparation method Methods 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 230000009467 reduction Effects 0.000 claims description 13
- 238000006722 reduction reaction Methods 0.000 claims description 13
- 150000002576 ketones Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 102000012740 beta Adrenergic Receptors Human genes 0.000 claims description 6
- 108010079452 beta Adrenergic Receptors Proteins 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000006239 protecting group Chemical group 0.000 claims description 6
- 230000001225 therapeutic effect Effects 0.000 claims description 3
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000001041 indolyl group Chemical group 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 238000005932 reductive alkylation reaction Methods 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 129
- 239000000243 solution Substances 0.000 description 115
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 111
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical class CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 98
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 61
- 239000007787 solid Substances 0.000 description 57
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 40
- 239000003054 catalyst Substances 0.000 description 38
- 239000000203 mixture Substances 0.000 description 34
- 239000003921 oil Substances 0.000 description 31
- 235000019198 oils Nutrition 0.000 description 31
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 30
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 30
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 230000000694 effects Effects 0.000 description 23
- 238000001953 recrystallisation Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- 238000003756 stirring Methods 0.000 description 15
- 239000013078 crystal Substances 0.000 description 14
- 239000000706 filtrate Substances 0.000 description 14
- 239000012280 lithium aluminium hydride Substances 0.000 description 14
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 10
- 238000010521 absorption reaction Methods 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 10
- 229960001317 isoprenaline Drugs 0.000 description 10
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- 238000001035 drying Methods 0.000 description 9
- 239000007789 gas Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000009835 boiling Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000001665 trituration Methods 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
- 150000002009 diols Chemical class 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 229940073735 4-hydroxy acetophenone Drugs 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910003445 palladium oxide Inorganic materials 0.000 description 6
- JQPTYAILLJKUCY-UHFFFAOYSA-N palladium(ii) oxide Chemical compound [O-2].[Pd+2] JQPTYAILLJKUCY-UHFFFAOYSA-N 0.000 description 6
- 229910000029 sodium carbonate Inorganic materials 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 238000007327 hydrogenolysis reaction Methods 0.000 description 5
- 229960003712 propranolol Drugs 0.000 description 5
- 239000012279 sodium borohydride Substances 0.000 description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 description 5
- 230000004936 stimulating effect Effects 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229940124630 bronchodilator Drugs 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 210000003205 muscle Anatomy 0.000 description 4
- 210000004165 myocardium Anatomy 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 150000003141 primary amines Chemical class 0.000 description 4
- 229960000581 salicylamide Drugs 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 241000282472 Canis lupus familiaris Species 0.000 description 3
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
- 208000001871 Tachycardia Diseases 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 230000003197 catalytic effect Effects 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 238000010828 elution Methods 0.000 description 3
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 3
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 3
- 238000010253 intravenous injection Methods 0.000 description 3
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 230000006794 tachycardia Effects 0.000 description 3
- PEHKIYKLNBXJJT-UHFFFAOYSA-N (2-methylphenyl)methanediol Chemical compound CC1=CC=CC=C1C(O)O PEHKIYKLNBXJJT-UHFFFAOYSA-N 0.000 description 2
- ZNPSVQGEQWUYTK-UHFFFAOYSA-N (3-methylphenyl)methanediol Chemical compound CC1=CC=CC(C(O)O)=C1 ZNPSVQGEQWUYTK-UHFFFAOYSA-N 0.000 description 2
- LVZNXBFKYXZNIS-UHFFFAOYSA-N 2-hydroxy-4-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzamide Chemical compound CC(C)NCC(O)C1=CC=C(C(N)=O)C(O)=C1 LVZNXBFKYXZNIS-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- PCBSXBYCASFXTM-UHFFFAOYSA-N 4-(4-Methoxyphenyl)-2-butanone Chemical compound COC1=CC=C(CCC(C)=O)C=C1 PCBSXBYCASFXTM-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 208000009079 Bronchial Spasm Diseases 0.000 description 2
- 208000014181 Bronchial disease Diseases 0.000 description 2
- 206010006482 Bronchospasm Diseases 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- 240000001414 Eucalyptus viminalis Species 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 208000010412 Glaucoma Diseases 0.000 description 2
- NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- FIDLYNBSMRFNLL-UHFFFAOYSA-N benzyl(propan-2-yl)azanium;bromide Chemical compound Br.CC(C)NCC1=CC=CC=C1 FIDLYNBSMRFNLL-UHFFFAOYSA-N 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 230000002526 effect on cardiovascular system Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004678 hydrides Chemical class 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- FVWZMDORPRMMDU-UHFFFAOYSA-N methyl 4-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC=C(C(=O)CBr)C=C1O FVWZMDORPRMMDU-UHFFFAOYSA-N 0.000 description 2
- YRPHNSODVHXAOP-UHFFFAOYSA-N methyl 5-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound COC(=O)C1=CC(C(=O)CBr)=CC=C1O YRPHNSODVHXAOP-UHFFFAOYSA-N 0.000 description 2
- PIDGASBUYKWVIL-UHFFFAOYSA-N methyl 5-[2-(dibenzylamino)acetyl]-2-hydroxybenzoate hydrochloride Chemical compound Cl.COC(C=1C(O)=CC=C(C1)C(CN(CC1=CC=CC=C1)CC1=CC=CC=C1)=O)=O PIDGASBUYKWVIL-UHFFFAOYSA-N 0.000 description 2
- AWXOSGITYMTEBI-UHFFFAOYSA-N methyl 5-[2-[benzyl(propan-2-yl)amino]acetyl]-2-hydroxybenzoate;hydrochloride Chemical compound Cl.C1=C(O)C(C(=O)OC)=CC(C(=O)CN(CC=2C=CC=CC=2)C(C)C)=C1 AWXOSGITYMTEBI-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- DLSOILHAKCBARI-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine Chemical compound CC(C)(C)NCC1=CC=CC=C1 DLSOILHAKCBARI-UHFFFAOYSA-N 0.000 description 2
- MMNNFMKNCOKXLZ-UHFFFAOYSA-N n-benzyl-2-methylpropan-2-amine;hydrobromide Chemical compound Br.CC(C)(C)NCC1=CC=CC=C1 MMNNFMKNCOKXLZ-UHFFFAOYSA-N 0.000 description 2
- 230000001962 neuropharmacologic effect Effects 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-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
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000003389 potentiating effect Effects 0.000 description 2
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- LDVHYJKRIKBISQ-UHFFFAOYSA-N 1-(1h-indol-3-yl)propan-2-one Chemical compound C1=CC=C2C(CC(=O)C)=CNC2=C1 LDVHYJKRIKBISQ-UHFFFAOYSA-N 0.000 description 1
- UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 description 1
- WFWKNGZODAOLEO-UHFFFAOYSA-N 1-(4-Methoxyphenyl)-2-propanone Chemical compound COC1=CC=C(CC(C)=O)C=C1 WFWKNGZODAOLEO-UHFFFAOYSA-N 0.000 description 1
- LAMHAMBOLINJML-UHFFFAOYSA-N 1-[3-(chloromethyl)-4-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=CC=C(O)C(CCl)=C1 LAMHAMBOLINJML-UHFFFAOYSA-N 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- QWAVNXZAQASOML-UHFFFAOYSA-N 1-phenoxypropan-2-one Chemical compound CC(=O)COC1=CC=CC=C1 QWAVNXZAQASOML-UHFFFAOYSA-N 0.000 description 1
- ABFCOJLLBHXNOU-UHFFFAOYSA-N 2-(2-hydroxyphenyl)ethanol Chemical compound OCCC1=CC=CC=C1O ABFCOJLLBHXNOU-UHFFFAOYSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- OCLIQASIQHOWRE-UHFFFAOYSA-N 2-[benzyl(tert-butyl)amino]-1-[4-hydroxy-3-(hydroxymethyl)phenyl]ethanone Chemical compound C=1C=CC=CC=1CN(C(C)(C)C)CC(=O)C1=CC=C(O)C(CO)=C1 OCLIQASIQHOWRE-UHFFFAOYSA-N 0.000 description 1
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- WWEHSHLGYLLHQS-UHFFFAOYSA-N 5-butanoyl-2-hydroxybenzoic acid Chemical compound CCCC(=O)C1=CC=C(O)C(C(O)=O)=C1 WWEHSHLGYLLHQS-UHFFFAOYSA-N 0.000 description 1
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- 206010062119 Sympathomimetic effect Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
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- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 1
- 229960004373 acetylcholine Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
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- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
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- 229940054051 antipsychotic indole derivative Drugs 0.000 description 1
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- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
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- 229910000085 borane Inorganic materials 0.000 description 1
- 230000007883 bronchodilation Effects 0.000 description 1
- 239000000168 bronchodilator agent Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
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- 229910052681 coesite Inorganic materials 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 1
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
- VKMGSWIFEHZQRS-UHFFFAOYSA-N dichloroisoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(Cl)C(Cl)=C1 VKMGSWIFEHZQRS-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- CHDFNIZLAAFFPX-UHFFFAOYSA-N ethoxyethane;oxolane Chemical compound CCOCC.C1CCOC1 CHDFNIZLAAFFPX-UHFFFAOYSA-N 0.000 description 1
- OUFLMGGBKDKXKJ-UHFFFAOYSA-N ethyl 5-(2-bromoacetyl)-2-hydroxybenzoate Chemical compound CCOC(=O)C1=CC(C(=O)CBr)=CC=C1O OUFLMGGBKDKXKJ-UHFFFAOYSA-N 0.000 description 1
- WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 239000012362 glacial acetic acid Substances 0.000 description 1
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- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 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
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- CBHGGHGLDABLAR-UHFFFAOYSA-N methyl 5-(2-amino-1-hydroxyethyl)-2-hydroxybenzoate;hydrochloride Chemical compound Cl.COC(=O)C1=CC(C(O)CN)=CC=C1O CBHGGHGLDABLAR-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000013081 microcrystal Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WZBCIFZVBDLSDN-UHFFFAOYSA-N n-benzyl-1-phenylmethanamine;hydrobromide Chemical compound Br.C=1C=CC=CC=1CNCC1=CC=CC=C1 WZBCIFZVBDLSDN-UHFFFAOYSA-N 0.000 description 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- GYCKQBWUSACYIF-UHFFFAOYSA-N o-hydroxybenzoic acid ethyl ester Natural products CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
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- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 238000010583 slow cooling Methods 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
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- 239000010902 straw Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- 238000010998 test method Methods 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
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/12—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms
- C07D295/125—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/13—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
- C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB18383/67A GB1200886A (en) | 1966-09-23 | 1966-09-23 | Phenylaminoethanol derivatives |
| GB1838367 | 1967-04-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO126014B true NO126014B (cs) | 1972-12-11 |
Family
ID=26253347
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO169835A NO126014B (cs) | 1966-09-23 | 1967-09-22 |
Country Status (15)
| Country | Link |
|---|---|
| US (3) | US3644353A (cs) |
| AT (1) | AT280996B (cs) |
| BE (1) | BE704037A (cs) |
| CH (1) | CH492676A (cs) |
| CS (1) | CS167874B2 (cs) |
| CY (1) | CY713A (cs) |
| DE (1) | DE1643224C3 (cs) |
| DK (1) | DK133618B (cs) |
| FR (2) | FR8010M (cs) |
| GB (1) | GB1200886A (cs) |
| IL (1) | IL28643A (cs) |
| NL (2) | NL160805C (cs) |
| NO (1) | NO126014B (cs) |
| PL (1) | PL70430B1 (cs) |
| SE (1) | SE354061B (cs) |
Families Citing this family (149)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE741762A (cs) * | 1968-11-18 | 1970-05-19 | ||
| US4101579A (en) * | 1969-02-06 | 1978-07-18 | Allen & Hanburys Limited | Phenethanolamine ethers |
| US4012444A (en) * | 1969-07-08 | 1977-03-15 | Allen & Hanburys Limited | 5-[1-Hydroxy-2-(1-methyl-3-phenylpropyl)aminoethyl] salicylamide and physiologically acceptable acid addition salts thereof |
| GB1266058A (cs) * | 1969-07-08 | 1972-03-08 | ||
| GB1298494A (en) * | 1970-06-17 | 1972-12-06 | Allen & Hanburys Ltd | Phenylethanolamine derivatives |
| AT310146B (de) * | 1971-04-26 | 1973-09-25 | Boehringer Sohn Ingelheim | Verfahren zur Herstellung von neuen N,N'-Bis-(β-hydroxyaryläthyl)-diaminoalkanen und deren Säureadditionssalzen |
| BE794414A (fr) * | 1972-01-25 | 1973-07-23 | Sandoz Sa | Nouveaux amino-alcools, leur preparation et leur application comme medicament |
| US4018825A (en) * | 1972-07-27 | 1977-04-19 | Warner-Lambert Company | 5-Hydroxy-α-(substituted aminomethyl)-m-xylene-α,α'-diols |
| US4024255A (en) * | 1973-04-05 | 1977-05-17 | Allen & Hanburys Limited | Tetrazole containing naphthyridine-3-carboxamides |
| US4000192A (en) * | 1973-05-07 | 1976-12-28 | Allen & Hanburys Limited | Pharmacologically active compounds |
| GB1468673A (en) * | 1973-05-07 | 1977-03-30 | Allen & Hanburys Ltd | Substituted benzamides |
| US3883560A (en) * | 1973-07-05 | 1975-05-13 | Colgate Palmolive Co | Salicylamidophenethanolamines |
| US4046913A (en) * | 1973-08-18 | 1977-09-06 | Boehringer Ingelheim Gmbh | 1-(M-alkanoyloxy-phenyl)-1-hydroxy-2-(N-lower alkyl-amino)-ethanes and salts thereof |
| US4022776A (en) * | 1974-01-31 | 1977-05-10 | Otsuka Pharmaceutical Company Limited | 5-[1-Hydroxy-2-(substituted-amino)]ethyl-8-hydroxycarbostyril derivatives |
| US4093628A (en) * | 1974-04-18 | 1978-06-06 | American Home Products Corporation | Thiophene ethanolamines |
| US4012528A (en) * | 1974-06-03 | 1977-03-15 | Smithkline Corporation | α-AMINOALKYL-3-(1,2-DIHYDROXYETHYL)-4-HYDROXY-BENZYL ALCOHOLS HAVING β-ADRENERGIC STIMULANT ACTIVITY |
| US4173583A (en) * | 1975-04-17 | 1979-11-06 | Schering Corporation | Diastereoisomers of 5-(1-hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide |
| GB1529972A (en) * | 1975-07-29 | 1978-10-25 | Allen & Hanburys Ltd | Basic alcohols |
| US4160036A (en) * | 1975-07-29 | 1979-07-03 | Allen & Hanburys Limited | 4-Hydroxy-1,3-benzenedimethanol derivatives |
| US4154761A (en) * | 1976-02-09 | 1979-05-15 | Allen & Hanburys Limited | Pharmacologically active compounds |
| JPS52113934A (en) * | 1976-03-19 | 1977-09-24 | Eisai Co Ltd | Phenethylamine derivatives and bronchodilator containing the same |
| US4055658A (en) * | 1976-05-17 | 1977-10-25 | Mead Johnson & Company | Cyanomethylphenethanolamines |
| US4127674A (en) * | 1977-03-21 | 1978-11-28 | Allergan Pharmaceuticals, Inc. | Method of treatment for glaucoma |
| US4163053A (en) * | 1977-12-27 | 1979-07-31 | Schering Corporation | Anti-hypertensive 5-[2-(substituted anilinoalkylamino)-1-hydroxyalkyl]salicylamides |
| DK160936C (da) * | 1978-07-03 | 1991-10-21 | Lilly Co Eli | Analogifremgangsmaade til fremstilling af optisk aktive phenethanolaminer |
| DE2833140A1 (de) * | 1978-07-28 | 1980-02-07 | Boehringer Sohn Ingelheim | Neue n-substituierte heterocyclen |
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-
1966
- 1966-09-23 GB GB18383/67A patent/GB1200886A/en not_active Expired
-
1967
- 1967-09-18 IL IL28643A patent/IL28643A/en unknown
- 1967-09-19 BE BE704037D patent/BE704037A/xx not_active IP Right Cessation
- 1967-09-20 PL PL1967122667A patent/PL70430B1/pl unknown
- 1967-09-20 US US669263A patent/US3644353A/en not_active Expired - Lifetime
- 1967-09-22 DE DE1643224A patent/DE1643224C3/de not_active Expired
- 1967-09-22 SE SE13078/67A patent/SE354061B/xx unknown
- 1967-09-22 NL NL6713016.A patent/NL160805C/xx not_active IP Right Cessation
- 1967-09-22 NO NO169835A patent/NO126014B/no unknown
- 1967-09-22 DK DK473167AA patent/DK133618B/da not_active IP Right Cessation
- 1967-09-22 AT AT864367A patent/AT280996B/de not_active IP Right Cessation
- 1967-09-22 CS CS6767*BA patent/CS167874B2/cs unknown
- 1967-09-25 FR FR122101A patent/FR8010M/fr not_active Expired
- 1967-09-25 CH CH1333967A patent/CH492676A/de not_active IP Right Cessation
- 1967-09-25 FR FR1557677D patent/FR1557677A/fr not_active Expired
-
1968
- 1968-04-15 US US721214A patent/US3642896A/en not_active Expired - Lifetime
-
1971
- 1971-06-02 US US149356A patent/US3705233A/en not_active Expired - Lifetime
-
1973
- 1973-11-26 CY CY71373A patent/CY713A/xx unknown
-
1978
- 1978-10-02 NL NL7809942A patent/NL7809942A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| US3642896A (en) | 1972-02-15 |
| SE354061B (cs) | 1973-02-26 |
| BE704037A (cs) | 1968-02-01 |
| NL6713016A (cs) | 1968-03-25 |
| DE1643224B2 (de) | 1978-11-23 |
| CY713A (en) | 1973-11-26 |
| NL160805C (nl) | 1979-12-17 |
| US3644353A (en) | 1972-02-22 |
| NL7809942A (nl) | 1979-01-31 |
| DK133618C (cs) | 1976-11-08 |
| NL160805B (nl) | 1979-07-16 |
| US3705233A (en) | 1972-12-05 |
| PL70430B1 (en) | 1974-02-28 |
| DK133618B (da) | 1976-06-21 |
| DE1643224A1 (de) | 1972-03-02 |
| DE1643224C3 (de) | 1979-08-09 |
| IL28643A (en) | 1971-12-29 |
| CH492676A (de) | 1970-06-30 |
| FR8010M (cs) | 1970-07-27 |
| AT280996B (de) | 1970-05-11 |
| GB1200886A (en) | 1970-08-05 |
| FR1557677A (cs) | 1969-02-21 |
| CS167874B2 (cs) | 1976-05-28 |
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