HU204502B - Process for producing aminopropanol derivatives of 3-(3-hydroxy-phenyl)-1-propanones and pharmaceutical compositions containing them - Google Patents
Process for producing aminopropanol derivatives of 3-(3-hydroxy-phenyl)-1-propanones and pharmaceutical compositions containing them Download PDFInfo
- Publication number
- HU204502B HU204502B HU883183A HU318388A HU204502B HU 204502 B HU204502 B HU 204502B HU 883183 A HU883183 A HU 883183A HU 318388 A HU318388 A HU 318388A HU 204502 B HU204502 B HU 204502B
- Authority
- HU
- Hungary
- Prior art keywords
- hydroxy
- phenyl
- propoxy
- propanone
- methoxyphenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 12
- MXZROAOUCUVNHX-UHFFFAOYSA-N 2-Aminopropanol Chemical class CCC(N)O MXZROAOUCUVNHX-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 31
- 239000002253 acid Substances 0.000 claims abstract description 27
- 238000002360 preparation method Methods 0.000 claims abstract description 17
- -1 t-pentylamino Chemical group 0.000 claims description 46
- 239000000203 mixture Substances 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000007858 starting material Substances 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 4
- KPYOQGLZSGFUKM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-[2-hydroxy-3-(propan-2-ylamino)propoxy]-4-methoxyphenyl]propan-1-one;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1C(=O)CCC1=CC=C(OC)C(OCC(O)CNC(C)C)=C1 KPYOQGLZSGFUKM-UHFFFAOYSA-N 0.000 claims description 3
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 3
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- PLIOOGSVDCSAJI-UHFFFAOYSA-N 3-[3-[2-hydroxy-3-(2-methylbutan-2-ylamino)propoxy]phenyl]-1-(3,4,5-trimethoxyphenyl)propan-1-one;hydrochloride Chemical compound Cl.CCC(C)(C)NCC(O)COC1=CC=CC(CCC(=O)C=2C=C(OC)C(OC)=C(OC)C=2)=C1 PLIOOGSVDCSAJI-UHFFFAOYSA-N 0.000 claims description 3
- WFGPIFXWVUQVNB-UHFFFAOYSA-N 3-[3-[2-hydroxy-3-(propylamino)propoxy]-4-methoxyphenyl]-1-naphthalen-2-ylpropan-1-one;hydrochloride Chemical compound Cl.C1=C(OC)C(OCC(O)CNCCC)=CC(CCC(=O)C=2C=C3C=CC=CC3=CC=2)=C1 WFGPIFXWVUQVNB-UHFFFAOYSA-N 0.000 claims description 3
- XKZZMMKJVKWQGE-UHFFFAOYSA-N 3-[3-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1-(2,4,6-trimethylphenyl)propan-1-one;hydrochloride Chemical compound Cl.CC1=CC(C)=CC(C)=C1C(=O)CCC1=CC=CC(OCC(O)CNC(C)(C)C)=C1 XKZZMMKJVKWQGE-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- AMQRNDIFPLIQBP-UHFFFAOYSA-N 3-(3-hydroxyphenyl)propanal Chemical class OC1=CC=CC(CCC=O)=C1 AMQRNDIFPLIQBP-UHFFFAOYSA-N 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 15
- 239000003826 tablet Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000008298 dragée Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 239000011248 coating agent Substances 0.000 description 9
- 238000000576 coating method Methods 0.000 description 9
- 230000003288 anthiarrhythmic effect Effects 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- 239000000829 suppository Substances 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000002775 capsule Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 5
- 229960000203 propafenone Drugs 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000000454 talc Substances 0.000 description 5
- 229910052623 talc Inorganic materials 0.000 description 5
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 239000007941 film coated tablet Substances 0.000 description 4
- 239000012458 free base Substances 0.000 description 4
- 229940016286 microcrystalline cellulose Drugs 0.000 description 4
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 4
- 239000008108 microcrystalline cellulose Substances 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 3
- GCSCDVSACXBHOQ-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-phenylpropan-1-one Chemical compound OC1=CC=CC(CCC(=O)C=2C=CC=CC=2)=C1 GCSCDVSACXBHOQ-UHFFFAOYSA-N 0.000 description 3
- 244000215068 Acacia senegal Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 229920000084 Gum arabic Polymers 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 3
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 3
- 229930006000 Sucrose Natural products 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 239000000205 acacia gum Substances 0.000 description 3
- 235000010489 acacia gum Nutrition 0.000 description 3
- 239000003416 antiarrhythmic agent Substances 0.000 description 3
- 206010003119 arrhythmia Diseases 0.000 description 3
- ZOMBKNNSYQHRCA-UHFFFAOYSA-J calcium sulfate hemihydrate Chemical compound O.[Ca+2].[Ca+2].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O ZOMBKNNSYQHRCA-UHFFFAOYSA-J 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 235000013681 dietary sucrose Nutrition 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000007903 gelatin capsule Substances 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229940031705 hydroxypropyl methylcellulose 2910 Drugs 0.000 description 3
- 229960003511 macrogol Drugs 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229960004793 sucrose Drugs 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 235000010215 titanium dioxide Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- DKFNGTLKSWXBQS-UHFFFAOYSA-N 3-[3-[3-(cyclohexylamino)-2-hydroxypropoxy]-4-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)propan-1-one;hydrochloride Chemical compound Cl.C1=C(OCC(O)CNC2CCCCC2)C(OC)=CC=C1CCC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DKFNGTLKSWXBQS-UHFFFAOYSA-N 0.000 description 2
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 2
- 241000282465 Canis Species 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 230000006793 arrhythmia Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000001768 carboxy methyl cellulose Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- VDKMYSMWQCFYBQ-UHFFFAOYSA-N diprafenone Chemical compound CCC(C)(C)NCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 VDKMYSMWQCFYBQ-UHFFFAOYSA-N 0.000 description 2
- 229950002948 diprafenone Drugs 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 229940116364 hard fat Drugs 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 239000003701 inert diluent Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000007918 intramuscular administration Methods 0.000 description 2
- 238000001990 intravenous administration Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 210000003540 papillary muscle Anatomy 0.000 description 2
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 2
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 2
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 1
- WIYZLEZVKNGUOI-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(2-hydroxy-3-piperidin-1-ylpropoxy)phenyl]propan-1-one hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)C(CCC1=CC(=CC=C1)OCC(CN1CCCCC1)O)=O WIYZLEZVKNGUOI-UHFFFAOYSA-N 0.000 description 1
- DZMULNWWBSJCIS-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-(oxiran-2-ylmethoxy)phenyl]propan-1-one Chemical compound C1=C(OC)C(OC)=CC=C1C(=O)CCC1=CC=CC(OCC2OC2)=C1 DZMULNWWBSJCIS-UHFFFAOYSA-N 0.000 description 1
- ODFZCRONAFARII-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)-3-[3-[2-hydroxy-3-(propylamino)propoxy]phenyl]propan-1-one hydrochloride Chemical compound CCCNCC(COC1=CC=CC(=C1)CCC(=O)C2=CC(=C(C=C2)OC)OC)O.Cl ODFZCRONAFARII-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 1
- GELMWIVBBPAMIO-UHFFFAOYSA-N 2-methylbutan-2-amine Chemical compound CCC(C)(C)N GELMWIVBBPAMIO-UHFFFAOYSA-N 0.000 description 1
- WHSMCMZFALLCCD-UHFFFAOYSA-N 3-(3-hydroxy-4-methoxyphenyl)-1-naphthalen-2-ylpropan-1-one Chemical compound C1=C(O)C(OC)=CC=C1CCC(=O)C1=CC=C(C=CC=C2)C2=C1 WHSMCMZFALLCCD-UHFFFAOYSA-N 0.000 description 1
- KVQFREJFKHVJDP-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1-phenanthren-3-ylpropan-1-one Chemical compound OC1=CC=CC(CCC(=O)C=2C=C3C4=CC=CC=C4C=CC3=CC=2)=C1 KVQFREJFKHVJDP-UHFFFAOYSA-N 0.000 description 1
- HYKZUSHZIXHJRZ-UHFFFAOYSA-N 3-[3-(2-hydroxy-3-morpholin-4-ylpropoxy)-4-methoxyphenyl]-1-(4-methylphenyl)propan-1-one hydrochloride Chemical compound Cl.CC1=CC=C(C=C1)C(CCC1=CC(=C(C=C1)OC)OCC(CN1CCOCC1)O)=O HYKZUSHZIXHJRZ-UHFFFAOYSA-N 0.000 description 1
- CSLQKMQMZYPZNE-UHFFFAOYSA-N 3-[3-(oxiran-2-ylmethoxy)phenyl]-1-(3,4,5-trimethoxyphenyl)propan-1-one Chemical compound COC=1C=C(C=C(C=1OC)OC)C(CCC1=CC(=CC=C1)OCC1CO1)=O CSLQKMQMZYPZNE-UHFFFAOYSA-N 0.000 description 1
- ODIFGPQWOAPOHO-UHFFFAOYSA-N 3-[3-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-1-(3,4,5-trimethoxyphenyl)propan-1-one hydrochloride Chemical compound CC(C)NCC(COC1=CC=CC(=C1)CCC(=O)C2=CC(=C(C(=C2)OC)OC)OC)O.Cl ODIFGPQWOAPOHO-UHFFFAOYSA-N 0.000 description 1
- AQTLDYIXFQDLNF-UHFFFAOYSA-N 3-[3-[2-hydroxy-3-(propylamino)propoxy]-4-methoxyphenyl]-1-(2-methoxyphenyl)propan-1-one hydrochloride Chemical compound Cl.COC1=C(C=CC=C1)C(CCC1=CC(=C(C=C1)OC)OCC(CNCCC)O)=O AQTLDYIXFQDLNF-UHFFFAOYSA-N 0.000 description 1
- ZSRCWVHUPQLUMT-UHFFFAOYSA-N 3-[3-[2-hydroxy-3-(propylamino)propoxy]phenyl]-1-phenanthren-3-ylpropan-1-one hydrochloride Chemical compound Cl.C1=CC(=CC=2C3=CC=CC=C3C=CC12)C(CCC1=CC(=CC=C1)OCC(CNCCC)O)=O ZSRCWVHUPQLUMT-UHFFFAOYSA-N 0.000 description 1
- QXHUOMIOXFLLFZ-UHFFFAOYSA-N 3-[3-[3-(cyclohexylamino)-2-hydroxypropoxy]-4-methoxyphenyl]-1-(4-methylphenyl)propan-1-one hydrochloride Chemical compound Cl.CC1=CC=C(C=C1)C(CCC1=CC(=C(C=C1)OC)OCC(CNC1CCCCC1)O)=O QXHUOMIOXFLLFZ-UHFFFAOYSA-N 0.000 description 1
- DGAXQAODMCBVEB-UHFFFAOYSA-N 3-[3-[3-(tert-butylamino)-2-hydroxypropoxy]phenyl]-1-(3,4-dimethoxyphenyl)propan-1-one hydrochloride Chemical compound Cl.COC=1C=C(C=CC1OC)C(CCC1=CC(=CC=C1)OCC(CNC(C)(C)C)O)=O DGAXQAODMCBVEB-UHFFFAOYSA-N 0.000 description 1
- PDMRVWRDLARBKH-UHFFFAOYSA-N 3-[4-methoxy-3-(oxiran-2-ylmethoxy)phenyl]-1-(2,4,6-trimethylphenyl)propan-1-one Chemical compound CC1=C(C(=CC(=C1)C)C)C(CCC1=CC(=C(C=C1)OC)OCC1CO1)=O PDMRVWRDLARBKH-UHFFFAOYSA-N 0.000 description 1
- OWKVSPXNFHNZHA-UHFFFAOYSA-N 3-[4-methoxy-3-(oxiran-2-ylmethoxy)phenyl]-1-(4-methylphenyl)propan-1-one Chemical compound CC1=CC=C(C=C1)C(CCC1=CC(=C(C=C1)OC)OCC1CO1)=O OWKVSPXNFHNZHA-UHFFFAOYSA-N 0.000 description 1
- YUBVMXPANMVGBE-UHFFFAOYSA-N 3-[4-methoxy-3-(oxiran-2-ylmethoxy)phenyl]-1-naphthalen-2-ylpropan-1-one Chemical compound C1=C(C=CC2=CC=CC=C12)C(CCC1=CC(=C(C=C1)OC)OCC1CO1)=O YUBVMXPANMVGBE-UHFFFAOYSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical class OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
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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
- C07D295/08—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 bound oxygen or sulfur atoms
- C07D295/084—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—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 bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (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 |
|---|---|---|---|
| EP87109016A EP0296265A1 (de) | 1987-06-23 | 1987-06-23 | Aminopropanolderivate von 3-(3-Hydroxyphenyl)-1-propanon-derivaten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT51233A HUT51233A (en) | 1990-04-28 |
| HU204502B true HU204502B (en) | 1992-01-28 |
Family
ID=8197085
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU883183A HU204502B (en) | 1987-06-23 | 1988-06-22 | Process for producing aminopropanol derivatives of 3-(3-hydroxy-phenyl)-1-propanones and pharmaceutical compositions containing them |
Country Status (20)
| Country | Link |
|---|---|
| EP (2) | EP0296265A1 (en, 2012) |
| JP (1) | JPS6426541A (en, 2012) |
| KR (1) | KR890000401A (en, 2012) |
| AR (1) | AR246246A1 (en, 2012) |
| AT (1) | ATE68479T1 (en, 2012) |
| CA (1) | CA1331877C (en, 2012) |
| DD (1) | DD271108A5 (en, 2012) |
| DE (2) | DE3865547D1 (en, 2012) |
| DK (1) | DK342288A (en, 2012) |
| ES (1) | ES2008640T3 (en, 2012) |
| FI (1) | FI92482C (en, 2012) |
| GR (2) | GR890300050T1 (en, 2012) |
| HR (1) | HRP920925A2 (en, 2012) |
| HU (1) | HU204502B (en, 2012) |
| IL (1) | IL86813A (en, 2012) |
| NO (1) | NO167975C (en, 2012) |
| PT (1) | PT87793B (en, 2012) |
| SU (1) | SU1634135A3 (en, 2012) |
| YU (1) | YU120088A (en, 2012) |
| ZA (1) | ZA884437B (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH08508270A (ja) * | 1993-03-29 | 1996-09-03 | ビーエーエスエフ アクチエンゲゼルシャフト | マルチ・ドラッグ耐性のモジュレーターとしての１−アミノ−３−フェノキシ−プロパン誘導体 |
| US6025359A (en) * | 1996-06-17 | 2000-02-15 | Eli Lilly And Company | Drug resistance and multidrug resistance modulators |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT66890B (fr) * | 1976-08-21 | 1979-01-25 | Hexachimie | Procede pour la preparation des aryloxy-1 amino-3 propanol-2 |
| DE3226863A1 (de) * | 1981-09-18 | 1983-04-07 | Basf Ag, 6700 Ludwigshafen | Aminopropanolderivate von 2-hydroxy-ss-phenyl-propiophenonen, verfahren zu ihrer herstellung und diese enthaltende therapeutische mittel |
| US4540697A (en) * | 1982-09-09 | 1985-09-10 | Basf Aktiengesellschaft | Aminopropanol derivatives of 2-hydroxy-β-phenyl-propiophenones, pharmaceutical compositions and use |
-
1987
- 1987-06-23 EP EP87109016A patent/EP0296265A1/de not_active Withdrawn
-
1988
- 1988-06-21 IL IL86813A patent/IL86813A/xx not_active IP Right Cessation
- 1988-06-22 DK DK342288A patent/DK342288A/da not_active Application Discontinuation
- 1988-06-22 HU HU883183A patent/HU204502B/hu not_active IP Right Cessation
- 1988-06-22 DD DD88317034A patent/DD271108A5/de not_active IP Right Cessation
- 1988-06-22 ZA ZA884437A patent/ZA884437B/xx unknown
- 1988-06-22 CA CA000570097A patent/CA1331877C/en not_active Expired - Fee Related
- 1988-06-22 PT PT87793A patent/PT87793B/pt not_active IP Right Cessation
- 1988-06-22 AR AR88311194A patent/AR246246A1/es active
- 1988-06-22 FI FI883001A patent/FI92482C/fi not_active IP Right Cessation
- 1988-06-22 YU YU01200/88A patent/YU120088A/xx unknown
- 1988-06-22 JP JP63154577A patent/JPS6426541A/ja active Granted
- 1988-06-22 KR KR1019880007508A patent/KR890000401A/ko not_active Ceased
- 1988-06-22 NO NO882771A patent/NO167975C/no unknown
- 1988-06-22 SU SU884355989A patent/SU1634135A3/ru active
- 1988-06-23 DE DE8888110034T patent/DE3865547D1/de not_active Expired - Fee Related
- 1988-06-23 DE DE3821250A patent/DE3821250A1/de not_active Ceased
- 1988-06-23 EP EP88110034A patent/EP0297435B1/de not_active Expired - Lifetime
- 1988-06-23 ES ES198888110034T patent/ES2008640T3/es not_active Expired - Lifetime
- 1988-06-23 AT AT88110034T patent/ATE68479T1/de active
-
1989
- 1989-05-25 GR GR89300050T patent/GR890300050T1/el unknown
-
1991
- 1991-12-02 GR GR91401885T patent/GR3003257T3/el unknown
-
1992
- 1992-10-02 HR HR920925A patent/HRP920925A2/hr not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |