FI62065C - Foerfarande foer framstaellning av terapeutiskt anvaendbara alylsulfonylfenoxipropanolaminer och deras syra-additionssa ltr - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara alylsulfonylfenoxipropanolaminer och deras syra-additionssa ltr Download PDFInfo
- Publication number
- FI62065C FI62065C FI750875A FI750875A FI62065C FI 62065 C FI62065 C FI 62065C FI 750875 A FI750875 A FI 750875A FI 750875 A FI750875 A FI 750875A FI 62065 C FI62065 C FI 62065C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- alkyl
- compound
- alkylsulfonyl
- methylsulfonyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 35
- -1 1-phenoxymethylethyl Chemical group 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical group 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 238000009472 formulation Methods 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 9
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 7
- 150000003945 chlorohydrins Chemical class 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 4
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 230000000747 cardiac effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 239000000706 filtrate Substances 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
- NCNBIKGGTLJPCI-UHFFFAOYSA-N 1-(5-methyl-2-methylsulfonylphenoxy)-3-(propan-2-ylamino)propan-2-ol;hydrochloride Chemical compound Cl.CC(C)NCC(O)COC1=CC(C)=CC=C1S(C)(=O)=O NCNBIKGGTLJPCI-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 3
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 2
- 241000700199 Cavia porcellus Species 0.000 description 2
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 230000002057 chronotropic effect Effects 0.000 description 2
- 235000015165 citric acid Nutrition 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000174 gluconic acid Substances 0.000 description 2
- 235000012208 gluconic acid Nutrition 0.000 description 2
- 208000019622 heart disease Diseases 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000000297 inotrophic effect Effects 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 229940039009 isoproterenol Drugs 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CTOXXLRUDZFYNZ-UHFFFAOYSA-N n-benzyl-n-(oxiran-2-ylmethyl)propan-2-amine Chemical compound C=1C=CC=CC=1CN(C(C)C)CC1CO1 CTOXXLRUDZFYNZ-UHFFFAOYSA-N 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 150000002924 oxiranes Chemical class 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 230000036515 potency Effects 0.000 description 2
- 229960003712 propranolol Drugs 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000006318 tert-butyl amino group Chemical group [H]N(*)C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- YONLFQNRGZXBBF-ZIAGYGMSSA-N (2r,3r)-2,3-dibenzoyloxybutanedioic acid Chemical compound O([C@@H](C(=O)O)[C@@H](OC(=O)C=1C=CC=CC=1)C(O)=O)C(=O)C1=CC=CC=C1 YONLFQNRGZXBBF-ZIAGYGMSSA-N 0.000 description 1
- 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
- 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 description 1
- VDBRPDLPBNDQPO-UHFFFAOYSA-N 1-(4-methylsulfonylphenoxy)-3-(propan-2-ylamino)propan-2-ol hydrochloride Chemical compound Cl.CC(C)NCC(O)COC1=CC=C(S(C)(=O)=O)C=C1 VDBRPDLPBNDQPO-UHFFFAOYSA-N 0.000 description 1
- VNIJAPHAFCSQPT-UHFFFAOYSA-N 1-(5-methyl-2-methylsulfonylphenoxy)propan-2-ol Chemical compound CS(=O)(=O)C1=C(C=C(C=C1)C)OCC(C)O VNIJAPHAFCSQPT-UHFFFAOYSA-N 0.000 description 1
- BVXMEZSLCMAANF-UHFFFAOYSA-N 1-(tert-butylamino)-3-(4-methylsulfonylphenoxy)propan-2-ol Chemical compound CC(C)(C)NCC(O)COC1=CC=C(S(C)(=O)=O)C=C1 BVXMEZSLCMAANF-UHFFFAOYSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- WHLMTNMNXHKIIH-UHFFFAOYSA-N 1-[benzyl(propan-2-yl)amino]-3-(5-methyl-2-methylsulfonylphenoxy)propan-2-ol Chemical compound C=1C=CC=CC=1CN(C(C)C)CC(O)COC1=CC(C)=CC=C1S(C)(=O)=O WHLMTNMNXHKIIH-UHFFFAOYSA-N 0.000 description 1
- IKYFHRVPKIFGMH-UHFFFAOYSA-N 1-phenoxypropan-2-amine Chemical compound CC(N)COC1=CC=CC=C1 IKYFHRVPKIFGMH-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 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
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris 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
- QXUIQNLUAZQJLQ-UHFFFAOYSA-N CC1=C(C=CC(=C1C(=O)O)O)S(=O)(=O)C Chemical compound CC1=C(C=CC(=C1C(=O)O)O)S(=O)(=O)C QXUIQNLUAZQJLQ-UHFFFAOYSA-N 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
- HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 208000007443 Neurasthenia Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 239000000674 adrenergic antagonist Substances 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940124630 bronchodilator Drugs 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 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
- 238000002288 cocrystallisation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 125000006317 cyclopropyl amino group Chemical group 0.000 description 1
- 229960001270 d- tartaric acid Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 150000003944 halohydrins Chemical class 0.000 description 1
- 210000002837 heart atrium Anatomy 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([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
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 210000002464 muscle smooth vascular Anatomy 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 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
- 150000007524 organic acids Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 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
- 230000002265 prevention Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 230000004648 relaxation of smooth muscle Effects 0.000 description 1
- 210000002460 smooth muscle Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 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
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 210000005090 tracheal smooth muscle Anatomy 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
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45509974A | 1974-03-27 | 1974-03-27 | |
| US45509974 | 1974-03-27 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI750875A7 FI750875A7 (en(2012)) | 1975-09-28 |
| FI62065B FI62065B (fi) | 1982-07-30 |
| FI62065C true FI62065C (fi) | 1982-11-10 |
Family
ID=23807402
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI750875A FI62065C (fi) | 1974-03-27 | 1975-03-24 | Foerfarande foer framstaellning av terapeutiskt anvaendbara alylsulfonylfenoxipropanolaminer och deras syra-additionssa ltr |
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 |
| 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 |
| CA1055528A (en) | 1979-05-29 |
| 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 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4824963A (en) | Process for the preparation of optically-active carbazole derivatives | |
| US4081447A (en) | 5-[2-Hydroxy-3-(3,4-dimethoxy phenethylamino)]-propoxy-3,4-dihydro carbostyril and pharmaceutically acceptable salts thereof | |
| JP2637737B2 (ja) | 新規な薬剤 | |
| EP0399504B1 (en) | Aryloxyphenylpropylamines their preparation and use | |
| US4067904A (en) | Alkylsulfonylphenoxypropanolamine derivatives | |
| PL90695B1 (en(2012)) | ||
| FI77224B (fi) | Foerfarande foer framstaellning av nya, terapeutiskt anvaendbara aminopropanolderivat av 2-hydroxi- -fenylpropiofenoner. | |
| EP0467325A2 (en) | Carbostyril derivatives | |
| PH26828A (en) | Benzonitrile derivatives pharmaceutical preparations and use thereof | |
| FI62065C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara alylsulfonylfenoxipropanolaminer och deras syra-additionssa ltr | |
| NZ196086A (en) | 1-phenyl-2-cyclohexene-1-alkylamine derivatives and pharmaceutical compositions | |
| EP0025727A1 (fr) | Dérivés de l'indole, procédé pour leur préparation et médicaments les contenant | |
| US4880841A (en) | Process of producing phenethylamine derivatives | |
| US6214882B1 (en) | Benzenesulphonamide derivatives, preparation thereof and therapeutical uses thereof | |
| NZ195702A (en) | 7-(3-(isopropyl or t-butyl)amino-2-hydroxypropoxy)-indolin-2,3-diones | |
| EP0625981A1 (en) | Azabicyclo compounds as calcium channel antagonists | |
| US5198587A (en) | Phenethylamine derivatives | |
| EP0467435A2 (en) | Benzhydryl derivatives having calmodulin inhibitor properties | |
| NZ197184A (en) | 1-(4-(2-phenethyloxyethoxy)phenoxy)-3-(branchedalkyl)-aminoprpan-2-ols | |
| JPS58116434A (ja) | 置換されたフエノキシアルカノ−ルアミン類及びフエノキシアルカノ−ル−シクロアルキルアミン類 | |
| US4119729A (en) | Alkylsulfonylphenoxypropanolamine therapeutic process | |
| GB2065645A (en) | Novel derivatives of 2-aminoethanol | |
| FI92482C (fi) | Menetelmä terapeuttisesti käyttökelpoisten 3-(3-hydroksifenyyli)-1-propanoniyhdisteiden aminopropanolijohdannaisten valmistamiseksi | |
| US4201790A (en) | Benzophenone derivatives | |
| GB2044251A (en) | Phenoxypropanolamine derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: BRISTOL-MYERS CO |