CA1055528A - Alkylsulfonylphenoxypropanolamines - Google Patents
AlkylsulfonylphenoxypropanolaminesInfo
- Publication number
- CA1055528A CA1055528A CA221,803A CA221803A CA1055528A CA 1055528 A CA1055528 A CA 1055528A CA 221803 A CA221803 A CA 221803A CA 1055528 A CA1055528 A CA 1055528A
- Authority
- CA
- Canada
- Prior art keywords
- methylsulfonyl
- propanol
- acid addition
- pharmaceutically acceptable
- addition salt
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 claims abstract description 48
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 150000001875 compounds Chemical class 0.000 claims abstract description 33
- 239000002253 acid Substances 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 28
- 231100000252 nontoxic Toxicity 0.000 claims description 24
- 230000003000 nontoxic effect Effects 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 13
- 239000007795 chemical reaction product Substances 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 10
- -1 phenoxyisopropyl Chemical group 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- KGPGKOSHODHUSR-UHFFFAOYSA-N 3-methyl-4-methylsulfonylphenol Chemical compound CC1=CC(O)=CC=C1S(C)(=O)=O KGPGKOSHODHUSR-UHFFFAOYSA-N 0.000 claims description 6
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000012458 free base Substances 0.000 claims description 4
- 150000002989 phenols Chemical class 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- IKYFHRVPKIFGMH-UHFFFAOYSA-N 1-phenoxypropan-2-amine Chemical compound CC(N)COC1=CC=CC=C1 IKYFHRVPKIFGMH-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- YDEYSUHFFPVVEU-UHFFFAOYSA-N 1-(5-methyl-2-methylsulfonylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(C)=CC=C1S(C)(=O)=O YDEYSUHFFPVVEU-UHFFFAOYSA-N 0.000 claims 2
- KECCFSZFXLAGJS-UHFFFAOYSA-N 4-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=C(O)C=C1 KECCFSZFXLAGJS-UHFFFAOYSA-N 0.000 claims 2
- ZWPDLYUJFRYTKN-UHFFFAOYSA-N 1-(2-methyl-5-methylsulfonylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC(S(C)(=O)=O)=CC=C1C ZWPDLYUJFRYTKN-UHFFFAOYSA-N 0.000 claims 1
- ACPNTKLYQRFQJN-UHFFFAOYSA-N 1-(4-methylsulfonylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=C(S(C)(=O)=O)C=C1 ACPNTKLYQRFQJN-UHFFFAOYSA-N 0.000 claims 1
- JVHYYNCSPAFJMI-UHFFFAOYSA-N 2-methyl-4-methylsulfonylphenol Chemical compound CC1=CC(S(C)(=O)=O)=CC=C1O JVHYYNCSPAFJMI-UHFFFAOYSA-N 0.000 claims 1
- ZWTZHHHSRDUVRT-UHFFFAOYSA-N 2-methylsulfonylphenol Chemical compound CS(=O)(=O)C1=CC=CC=C1O ZWTZHHHSRDUVRT-UHFFFAOYSA-N 0.000 claims 1
- 230000000903 blocking effect Effects 0.000 abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 5
- 238000011282 treatment Methods 0.000 abstract description 4
- 208000019622 heart disease Diseases 0.000 abstract description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- 150000003945 chlorohydrins Chemical class 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000037396 body weight Effects 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 230000036515 potency Effects 0.000 description 4
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000674 adrenergic antagonist Substances 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 230000002057 chronotropic effect Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000000297 inotrophic effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical compound O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 description 2
- 229960003712 propranolol Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 210000002460 smooth muscle Anatomy 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BNIITVMZJJEYHV-UHFFFAOYSA-N 1-(2-methylsulfonylphenoxy)-3-(propan-2-ylamino)propan-2-ol Chemical compound CC(C)NCC(O)COC1=CC=CC=C1S(C)(=O)=O BNIITVMZJJEYHV-UHFFFAOYSA-N 0.000 description 1
- SVRSFQXERGLUFF-UHFFFAOYSA-N 1-(5-methyl-2-methylsulfonylphenoxy)-3-[phenoxy(propan-2-yl)amino]propan-2-ol Chemical compound C=1C=CC=CC=1ON(C(C)C)CC(O)COC1=CC(C)=CC=C1S(C)(=O)=O SVRSFQXERGLUFF-UHFFFAOYSA-N 0.000 description 1
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 1
- JPPFLCUUYBYBGZ-UHFFFAOYSA-N 3-methyl-4-methylsulfonylphenol;sodium Chemical compound [Na].CC1=CC(O)=CC=C1S(C)(=O)=O JPPFLCUUYBYBGZ-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 240000001546 Byrsonima crassifolia Species 0.000 description 1
- 235000003197 Byrsonima crassifolia Nutrition 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 101150065749 Churc1 gene Proteins 0.000 description 1
- PXTOZBMKFACODY-UHFFFAOYSA-N Cl.C1(CCCC1)NCC(COC=1C=C(C=CC1S(=O)(=O)C)C)O Chemical compound Cl.C1(CCCC1)NCC(COC=1C=C(C=CC1S(=O)(=O)C)C)O PXTOZBMKFACODY-UHFFFAOYSA-N 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000007443 Neurasthenia Diseases 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 102100038239 Protein Churchill Human genes 0.000 description 1
- 244000000231 Sesamum indicum Species 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000048 adrenergic agonist Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 230000001746 atrial effect Effects 0.000 description 1
- 238000010009 beating Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003182 bronchodilatating effect Effects 0.000 description 1
- UVZGOOXAARJPHD-UHFFFAOYSA-N butan-2-one;methanol Chemical compound OC.CCC(C)=O UVZGOOXAARJPHD-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000001722 carbon compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 150000003943 catecholamines Chemical class 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 229910003480 inorganic solid Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- LYBKPDDZTNUNNM-UHFFFAOYSA-N isopropylbenzylamine Chemical compound CC(C)NCC1=CC=CC=C1 LYBKPDDZTNUNNM-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000007788 liquid Substances 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
- 210000003205 muscle Anatomy 0.000 description 1
- PEIJPMBOGRPKQJ-UHFFFAOYSA-N n-benzylpropan-2-amine;hydrochloride Chemical compound Cl.CC(C)NCC1=CC=CC=C1 PEIJPMBOGRPKQJ-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- RAIYODFGMLZUDF-UHFFFAOYSA-N piperidin-1-ium;acetate Chemical compound CC([O-])=O.C1CC[NH2+]CC1 RAIYODFGMLZUDF-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 229960004063 propylene glycol Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C315/00—Preparation of sulfones; Preparation of sulfoxides
- C07C315/04—Preparation of sulfones; Preparation of sulfoxides by reactions not involving the formation of sulfone or sulfoxide groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45509974A | 1974-03-27 | 1974-03-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1055528A true CA1055528A (en) | 1979-05-29 |
Family
ID=23807402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA221,803A Expired CA1055528A (en) | 1974-03-27 | 1975-03-11 | Alkylsulfonylphenoxypropanolamines |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS5822478B2 (en(2012)) |
| BE (1) | BE826873A (en(2012)) |
| CA (1) | CA1055528A (en(2012)) |
| CH (1) | CH612932A5 (en(2012)) |
| DE (1) | DE2513806A1 (en(2012)) |
| DK (1) | DK144246C (en(2012)) |
| FI (1) | FI62065C (en(2012)) |
| FR (2) | FR2265358B1 (en(2012)) |
| GB (1) | GB1451180A (en(2012)) |
| IE (1) | IE40887B1 (en(2012)) |
| LU (1) | LU72100A1 (en(2012)) |
| NL (1) | NL7503489A (en(2012)) |
| NO (1) | NO140856C (en(2012)) |
| SE (1) | SE424548B (en(2012)) |
| YU (2) | YU59175A (en(2012)) |
| ZA (1) | ZA751853B (en(2012)) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4117128A (en) | 1976-08-03 | 1978-09-26 | Smithkline Corporation | Sulfonyl benzofurans and benzothiophenes having coronary vasodilator activity |
| PL176532B1 (pl) * | 1993-12-07 | 1999-06-30 | S & R Maschbau Gmbh | Sposób pieczenia ciast oraz ruszt piekarnika i ramka do pieczenia ciast |
| WO1998033771A1 (fr) * | 1997-01-30 | 1998-08-06 | Senju Pharmaceutical Co., Ltd. | Derives d'hydroquinone |
-
1975
- 1975-03-11 CA CA221,803A patent/CA1055528A/en not_active Expired
- 1975-03-12 YU YU00591/75A patent/YU59175A/xx unknown
- 1975-03-19 BE BE154495A patent/BE826873A/xx unknown
- 1975-03-20 LU LU72100A patent/LU72100A1/xx unknown
- 1975-03-20 JP JP50033124A patent/JPS5822478B2/ja not_active Expired
- 1975-03-24 NO NO750993A patent/NO140856C/no unknown
- 1975-03-24 FI FI750875A patent/FI62065C/fi not_active IP Right Cessation
- 1975-03-24 DK DK123875A patent/DK144246C/da active
- 1975-03-24 FR FR7509047A patent/FR2265358B1/fr not_active Expired
- 1975-03-24 NL NL7503489A patent/NL7503489A/xx not_active Application Discontinuation
- 1975-03-24 ZA ZA00751853A patent/ZA751853B/xx unknown
- 1975-03-26 IE IE670/75A patent/IE40887B1/xx unknown
- 1975-03-26 SE SE7503582A patent/SE424548B/xx unknown
- 1975-03-26 GB GB1265275A patent/GB1451180A/en not_active Expired
- 1975-03-27 CH CH399675A patent/CH612932A5/xx not_active IP Right Cessation
- 1975-03-27 DE DE19752513806 patent/DE2513806A1/de not_active Ceased
-
1978
- 1978-08-31 FR FR7825229A patent/FR2391725A1/fr active Granted
-
1982
- 1982-06-03 YU YU01171/82A patent/YU117182A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IE40887B1 (en) | 1979-09-12 |
| YU117182A (en) | 1982-10-31 |
| NO140856C (no) | 1979-11-28 |
| NL7503489A (nl) | 1975-09-30 |
| FI62065C (fi) | 1982-11-10 |
| DK144246C (da) | 1982-06-28 |
| AU7839175A (en) | 1976-08-26 |
| FR2265358B1 (en(2012)) | 1980-02-08 |
| DK144246B (da) | 1982-01-25 |
| CH612932A5 (en) | 1979-08-31 |
| FI750875A7 (en(2012)) | 1975-09-28 |
| BE826873A (fr) | 1975-09-19 |
| JPS5822478B2 (ja) | 1983-05-09 |
| GB1451180A (en) | 1976-09-29 |
| YU59175A (en) | 1982-10-31 |
| JPS50130736A (en(2012)) | 1975-10-16 |
| IE40887L (en) | 1975-09-27 |
| FR2391725B1 (en(2012)) | 1981-07-17 |
| SE7503582L (en(2012)) | 1975-09-29 |
| NO750993L (en(2012)) | 1975-09-30 |
| NO140856B (no) | 1979-08-20 |
| LU72100A1 (en(2012)) | 1976-02-04 |
| DK123875A (en(2012)) | 1975-09-28 |
| SE424548B (sv) | 1982-07-26 |
| FR2265358A1 (en(2012)) | 1975-10-24 |
| FR2391725A1 (fr) | 1978-12-22 |
| FI62065B (fi) | 1982-07-30 |
| ZA751853B (en) | 1976-02-25 |
| DE2513806A1 (de) | 1975-10-09 |
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