CA1176643A - 1-¬3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl|-3- phenyl-1-propanones and their salts and a process for the preparation thereof - Google Patents
1-¬3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl|-3- phenyl-1-propanones and their salts and a process for the preparation thereofInfo
- Publication number
- CA1176643A CA1176643A CA000391069A CA391069A CA1176643A CA 1176643 A CA1176643 A CA 1176643A CA 000391069 A CA000391069 A CA 000391069A CA 391069 A CA391069 A CA 391069A CA 1176643 A CA1176643 A CA 1176643A
- Authority
- CA
- Canada
- Prior art keywords
- thienyl
- phenyl
- propanone
- hydroxy
- chlorohydrate
- 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
- 150000003839 salts Chemical class 0.000 title claims abstract description 12
- 238000000034 method Methods 0.000 title claims description 26
- 238000002360 preparation method Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 45
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 8
- 239000001257 hydrogen Substances 0.000 claims abstract description 8
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 9
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 4
- PVVSRISLNYSAKL-UHFFFAOYSA-N 1-[3-[2-hydroxy-3-(propylamino)propoxy]-5-methylthiophen-2-yl]-3-phenylpropan-1-one;hypochlorous acid Chemical compound ClO.C1=C(C)SC(C(=O)CCC=2C=CC=CC=2)=C1OCC(O)CNCCC PVVSRISLNYSAKL-UHFFFAOYSA-N 0.000 claims description 3
- -1 alkali metal cation Chemical class 0.000 claims description 3
- KTIGJGKPBULVFS-UHFFFAOYSA-N 1-[4,5-dimethyl-3-(oxiran-2-ylmethoxy)thiophen-2-yl]-3-phenylpropan-1-one Chemical compound C1OC1COC=1C(C)=C(C)SC=1C(=O)CCC1=CC=CC=C1 KTIGJGKPBULVFS-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- NGNQVLBGOQRLFL-UHFFFAOYSA-N 1-[3-(oxiran-2-ylmethoxy)thiophen-2-yl]-3-phenylpropan-1-one Chemical compound S1C=CC(OCC2OC2)=C1C(=O)CCC1=CC=CC=C1 NGNQVLBGOQRLFL-UHFFFAOYSA-N 0.000 claims 2
- GJACKNUPVZDHQQ-UHFFFAOYSA-N 1-[3-[2-hydroxy-3-(propylamino)propoxy]-4,5-dimethylthiophen-2-yl]-3-phenylpropan-1-one;hypochlorous acid Chemical compound ClO.CC1=C(C)SC(C(=O)CCC=2C=CC=CC=2)=C1OCC(O)CNCCC GJACKNUPVZDHQQ-UHFFFAOYSA-N 0.000 claims 2
- HDGBVLOEKJOBRH-UHFFFAOYSA-N 1-[3-[2-hydroxy-3-(propylamino)propoxy]-4-methylthiophen-2-yl]-3-phenylpropan-1-one;hypochlorous acid Chemical compound ClO.CC1=CSC(C(=O)CCC=2C=CC=CC=2)=C1OCC(O)CNCCC HDGBVLOEKJOBRH-UHFFFAOYSA-N 0.000 claims 2
- UJPYHJRAMUEQKL-UHFFFAOYSA-N 1-[3-[2-hydroxy-3-(propylamino)propoxy]thiophen-2-yl]-3-phenylpropan-1-one;hypochlorous acid Chemical compound ClO.C1=CSC(C(=O)CCC=2C=CC=CC=2)=C1OCC(O)CNCCC UJPYHJRAMUEQKL-UHFFFAOYSA-N 0.000 claims 2
- QJQCCYRQBPKXSP-UHFFFAOYSA-N 1-[3-[3-(butylamino)-2-hydroxypropoxy]thiophen-2-yl]-3-phenylpropan-1-one;hypochlorous acid Chemical compound ClO.C1=CSC(C(=O)CCC=2C=CC=CC=2)=C1OCC(O)CNCCCC QJQCCYRQBPKXSP-UHFFFAOYSA-N 0.000 claims 2
- JEZAEGDBHVGRKC-UHFFFAOYSA-N 1-[4-methyl-3-(oxiran-2-ylmethoxy)thiophen-2-yl]-3-phenylpropan-1-one Chemical compound C1OC1COC=1C(C)=CSC=1C(=O)CCC1=CC=CC=C1 JEZAEGDBHVGRKC-UHFFFAOYSA-N 0.000 claims 1
- XIYYANGEXAUUCT-UHFFFAOYSA-N 1-[5-methyl-3-(oxiran-2-ylmethoxy)thiophen-2-yl]-3-phenylpropan-1-one Chemical compound C=1C=CC=CC=1CCC(=O)C=1SC(C)=CC=1OCC1CO1 XIYYANGEXAUUCT-UHFFFAOYSA-N 0.000 claims 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 230000008018 melting Effects 0.000 description 14
- 238000002844 melting Methods 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 206010003119 arrhythmia Diseases 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 7
- 230000006793 arrhythmia Effects 0.000 description 7
- 239000001110 calcium chloride Substances 0.000 description 7
- 229910001628 calcium chloride Inorganic materials 0.000 description 7
- XFSBVAOIAHNAPC-XTHSEXKGSA-N 16-Ethyl-1alpha,6alpha,19beta-trimethoxy-4-(methoxymethyl)-aconitane-3alpha,8,10alpha,11,18alpha-pentol, 8-acetate 10-benzoate Chemical compound O([C@H]1[C@]2(O)C[C@H]3[C@@]45C6[C@@H]([C@@]([C@H]31)(OC(C)=O)[C@@H](O)[C@@H]2OC)[C@H](OC)[C@@H]4[C@]([C@@H](C[C@@H]5OC)O)(COC)CN6CC)C(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-XTHSEXKGSA-N 0.000 description 6
- XFSBVAOIAHNAPC-UHFFFAOYSA-N Aconitin Natural products CCN1CC(C(CC2OC)O)(COC)C3C(OC)C(C(C45)(OC(C)=O)C(O)C6OC)C1C32C4CC6(O)C5OC(=O)C1=CC=CC=C1 XFSBVAOIAHNAPC-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940039750 aconitine Drugs 0.000 description 6
- STDXGNLCJACLFY-UHFFFAOYSA-N aconitine Natural products CCN1CC2(COC)C(O)CC(O)C34C5CC6(O)C(OC)C(O)C(OC(=O)C)(C5C6OC(=O)c7ccccc7)C(C(OC)C23)C14 STDXGNLCJACLFY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 230000003288 anthiarrhythmic effect Effects 0.000 description 4
- 239000003416 antiarrhythmic agent Substances 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000007832 Na2SO4 Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000033764 rhythmic process Effects 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RFSKGCVUDQRZSD-UHFFFAOYSA-N 3-methoxythiophene Chemical compound COC=1C=CSC=1 RFSKGCVUDQRZSD-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 206010022998 Irritability Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000009729 Ventricular Premature Complexes Diseases 0.000 description 2
- 206010047281 Ventricular arrhythmia Diseases 0.000 description 2
- 206010047289 Ventricular extrasystoles Diseases 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000010253 intravenous injection Methods 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 208000003663 ventricular fibrillation Diseases 0.000 description 2
- JAMUQJWODRUNEV-UHFFFAOYSA-N 1-(3-hydroxy-4-methylthiophen-2-yl)-3-phenylpropan-1-one Chemical compound CC1=CSC(C(=O)CCC=2C=CC=CC=2)=C1O JAMUQJWODRUNEV-UHFFFAOYSA-N 0.000 description 1
- QMLTUPMRSDKBDK-UHFFFAOYSA-N 1-(3-hydroxy-5-methylthiophen-2-yl)-3-phenylpropan-1-one Chemical compound S1C(C)=CC(O)=C1C(=O)CCC1=CC=CC=C1 QMLTUPMRSDKBDK-UHFFFAOYSA-N 0.000 description 1
- DDFHBXJFDQAGJB-UHFFFAOYSA-N 1-(3-hydroxythiophen-2-yl)-3-phenylpropan-1-one Chemical compound C1=CSC(C(=O)CCC=2C=CC=CC=2)=C1O DDFHBXJFDQAGJB-UHFFFAOYSA-N 0.000 description 1
- YWMOXFOYIVUYTD-UHFFFAOYSA-N 1-(3-hydroxythiophen-2-yl)-3-phenylpropan-2-one Chemical compound C1=CSC(CC(=O)CC=2C=CC=CC=2)=C1O YWMOXFOYIVUYTD-UHFFFAOYSA-N 0.000 description 1
- IPZWKXNUJHIVKJ-UHFFFAOYSA-N 1-(3-methoxythiophen-2-yl)-3-phenylpropan-1-one Chemical compound C1=CSC(C(=O)CCC=2C=CC=CC=2)=C1OC IPZWKXNUJHIVKJ-UHFFFAOYSA-N 0.000 description 1
- VSGMXBVOHKACCP-UHFFFAOYSA-N 2,3,4-trimethoxythiophene Chemical compound COC1=CSC(OC)=C1OC VSGMXBVOHKACCP-UHFFFAOYSA-N 0.000 description 1
- UOBYKYZJUGYBDK-UHFFFAOYSA-N 2-naphthoic acid Chemical compound C1=CC=CC2=CC(C(=O)O)=CC=C21 UOBYKYZJUGYBDK-UHFFFAOYSA-N 0.000 description 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- RVDUJCGAAPQDBO-UHFFFAOYSA-N 3-hydroxythiophene-2-carboxylic acid Chemical compound OC(=O)C=1SC=CC=1O RVDUJCGAAPQDBO-UHFFFAOYSA-N 0.000 description 1
- WSHWKCQZDNZGFV-UHFFFAOYSA-N 3-methoxy-4,5-dimethylthiophene-2-carboxylic acid Chemical compound COC=1C(C)=C(C)SC=1C(O)=O WSHWKCQZDNZGFV-UHFFFAOYSA-N 0.000 description 1
- HGDGACBSGVRCSM-UHFFFAOYSA-N 3-methoxy-4-methylthiophene Chemical compound COC1=CSC=C1C HGDGACBSGVRCSM-UHFFFAOYSA-N 0.000 description 1
- IYTOVCKSPJGCOJ-UHFFFAOYSA-N 3-methoxy-5-methylthiophene-2-carboxylic acid Chemical compound COC=1C=C(C)SC=1C(O)=O IYTOVCKSPJGCOJ-UHFFFAOYSA-N 0.000 description 1
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 1
- MFEILWXBDBCWKF-UHFFFAOYSA-N 3-phenylpropanoyl chloride Chemical compound ClC(=O)CCC1=CC=CC=C1 MFEILWXBDBCWKF-UHFFFAOYSA-N 0.000 description 1
- ICQPBAWSBLMHGD-UHFFFAOYSA-N 4-methoxy-2-methylthiophene Chemical compound COC1=CSC(C)=C1 ICQPBAWSBLMHGD-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical compound C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 description 1
- 241000134884 Ericales Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 1
- 206010038669 Respiratory arrest Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229960000836 amitriptyline Drugs 0.000 description 1
- KRMDCWKBEZIMAB-UHFFFAOYSA-N amitriptyline Chemical compound C1CC2=CC=CC=C2C(=CCCN(C)C)C2=CC=CC=C21 KRMDCWKBEZIMAB-UHFFFAOYSA-N 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 230000001387 anti-histamine Effects 0.000 description 1
- 239000000739 antihistaminic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229960003914 desipramine Drugs 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- BCGWQEUPMDMJNV-UHFFFAOYSA-N imipramine Chemical compound C1CC2=CC=CC=C2N(CCCN(C)C)C2=CC=CC=C21 BCGWQEUPMDMJNV-UHFFFAOYSA-N 0.000 description 1
- 229960004801 imipramine Drugs 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 231100000518 lethal Toxicity 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- MWADWXJPBMFRGL-UHFFFAOYSA-N methyl 3-methoxythiophene-2-carboxylate Chemical compound COC(=O)C=1SC=CC=1OC MWADWXJPBMFRGL-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- JWHAUXFOSRPERK-UHFFFAOYSA-N propafenone Chemical compound CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 JWHAUXFOSRPERK-UHFFFAOYSA-N 0.000 description 1
- 229960000203 propafenone Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001519 thymoleptic effect Effects 0.000 description 1
- 230000002861 ventricular Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/32—Oxygen atoms
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/16—Radicals substituted by singly bound hetero atoms other than halogen by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0581880A AT369739B (de) | 1980-11-28 | 1980-11-28 | Verfahren zur herstellung neuer 1-(3-(2-hydroxy-3alkylaminopropoxy)-2-thienyl)-3-phenyl-1- propanone und ihrer saeureadditionssalze |
| ATA5818/80 | 1980-11-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1176643A true CA1176643A (en) | 1984-10-23 |
Family
ID=3579917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000391069A Expired CA1176643A (en) | 1980-11-28 | 1981-11-27 | 1-¬3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl|-3- phenyl-1-propanones and their salts and a process for the preparation thereof |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4352819A (en, 2012) |
| EP (1) | EP0053603B1 (en, 2012) |
| JP (1) | JPS57118582A (en, 2012) |
| AT (1) | AT369739B (en, 2012) |
| CA (1) | CA1176643A (en, 2012) |
| DE (1) | DE3169736D1 (en, 2012) |
| DK (1) | DK154216C (en, 2012) |
| FI (1) | FI72725C (en, 2012) |
| PT (1) | PT74051B (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3316155A1 (de) * | 1983-05-03 | 1984-11-08 | Helopharm W. Petrik & Co Kg, 1000 Berlin | 2-(2'hydroxy-3'-(1,1-dimethylpropylamino)-propoxy)-1-thienylpropiophenon, seine saeureadditionssalze, verfahren zu seiner herstellung und arzneimittel |
| JPS62178585A (ja) * | 1986-01-29 | 1987-08-05 | レフオ−サン−ゲゼルシヤフト エム・ベ−・ハ− | １−〔３−（２−ヒドロキシ−３−アルキルアミノプロポキシ）−２−チエニル〕−３−フエニル−１−プロパノン及びそれらの酸付加塩並びにそれらの製造法及びそれらを含む薬学的組成物 |
| ES2036600T3 (es) * | 1986-10-29 | 1993-06-01 | Dieter Prof. Dr. Binder | Procedimiento para preparar 1-(3-(2-dialquilaminoetoxi)-2-tienil)-3-fenil-1-propanonas. |
| AT392967B (de) * | 1989-01-24 | 1991-07-25 | Laevosan Gmbh & Co Kg | Neue 1-(3-(2-hydroxy-3-alkylaminopropoxy)-2- thienyl)-3-phenyl-1-propanone und verfahren zu deren herstellung |
| DE3907512C2 (de) * | 1989-03-08 | 1997-08-14 | Laevosan Gmbh & Co Kg | Neue Aryloxy-alkylamine, deren Herstellung und diese enthaltende Arzneimittel |
| FI90540C (fi) * | 1991-03-28 | 1994-02-25 | Neste Oy | Menetelmä 3-asemassa substituoidun tiofeenin valmistamiseksi |
| JP4608372B2 (ja) | 2005-06-09 | 2011-01-12 | パイオニア株式会社 | 保持装置およびディスク装置 |
| WO2016153094A1 (ko) * | 2015-03-26 | 2016-09-29 | 비스메르 주식회사 | 3-알콕시싸이오펜 유도체의 신규한 제조방법 |
| CN106146455A (zh) * | 2015-03-30 | 2016-11-23 | 维斯曼株式会社 | 3-烷氧基噻吩衍生物及其制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2720613A1 (de) * | 1977-05-07 | 1978-11-16 | Basf Ag | Aminoderivate von substituierten hydroxy-thiophenen |
| US4123550A (en) * | 1977-10-31 | 1978-10-31 | Syntex (U.S.A.) Inc. | Bicyclo[3.1.0]hexylethylaminocarbonyl-substituted heteroaryl cardiovascular agents |
-
1980
- 1980-11-28 AT AT0581880A patent/AT369739B/de not_active IP Right Cessation
-
1981
- 1981-11-17 EP EP81890190A patent/EP0053603B1/de not_active Expired
- 1981-11-17 DE DE8181890190T patent/DE3169736D1/de not_active Expired
- 1981-11-25 US US06/324,760 patent/US4352819A/en not_active Expired - Lifetime
- 1981-11-26 JP JP56188511A patent/JPS57118582A/ja active Granted
- 1981-11-26 FI FI813790A patent/FI72725C/fi not_active IP Right Cessation
- 1981-11-27 PT PT74051A patent/PT74051B/pt not_active IP Right Cessation
- 1981-11-27 DK DK526981A patent/DK154216C/da not_active IP Right Cessation
- 1981-11-27 CA CA000391069A patent/CA1176643A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| PT74051B (en) | 1983-04-26 |
| JPH036149B2 (en, 2012) | 1991-01-29 |
| DK526981A (da) | 1982-05-29 |
| PT74051A (en) | 1981-12-01 |
| EP0053603B1 (de) | 1985-04-03 |
| ATA581880A (de) | 1982-06-15 |
| DK154216B (da) | 1988-10-24 |
| JPS57118582A (en) | 1982-07-23 |
| DK154216C (da) | 1989-03-13 |
| FI72725C (fi) | 1987-07-10 |
| AT369739B (de) | 1983-01-25 |
| EP0053603A1 (de) | 1982-06-09 |
| FI72725B (fi) | 1987-03-31 |
| FI813790L (fi) | 1982-05-29 |
| US4352819A (en) | 1982-10-05 |
| DE3169736D1 (en) | 1985-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU578002A3 (ru) | Способ получени производных бензо(в)тиофена или их солей | |
| US3309406A (en) | 1-t-butylamino-3-phenoxy-2-propanols | |
| CA1176643A (en) | 1-¬3-(2-hydroxy-3-alkylaminopropoxy)-2-thienyl|-3- phenyl-1-propanones and their salts and a process for the preparation thereof | |
| Lavagnino et al. | Conidine—Synthesis, Polymerization and Derivatives | |
| EP0339671B1 (en) | Derivative of caffeic acid and pharmaceutical composition containing the same | |
| US4278796A (en) | Piperazines | |
| CA1161849A (en) | Derivatives of indole active on the cardiovascular system | |
| DK174505B1 (da) | Benzenderivater og fremgangsmåde til fremstilling deraf samt farmaceutiske midler indeholdende derivaterne | |
| US3223585A (en) | Pesticidal monosulfur heterocyclic compositions | |
| CA1129875A (en) | Chromone derivatives | |
| US3536723A (en) | P - (2 - alkyloxy - benzoyl) - aminobenzoates of n - dialkylamine - alkyl and their quaternary salts | |
| Weisbach et al. | Synthesis and Pharmacology of Some α-Oxy-and α-Hydroxy-1-benzyltetrahydroisoquinolines | |
| GB1599181A (en) | Oxyalkanoic acid derivatives | |
| US4034011A (en) | 1,1-Diphenyl-4-(substituted-amino)butanes | |
| CA1298832C (en) | 3-phenyl-1-propanones, process of preparing thereof and method of treating arrhythmias | |
| US3322778A (en) | Novel ether derivatives of benzmorphans | |
| JPH03167184A (ja) | Ｎ―ベンジルトロパンアミド類 | |
| CA1089866A (en) | Benzofuran derivatives, preparation thereof and pharmaceutical compositions thereof | |
| CA1327805C (en) | Pilocarpine derivatives | |
| JPH0227355B2 (ja) | 88benzoiruaminoarukirupirorichijinjudotai | |
| US4263430A (en) | 2-Methyl-5-(2-hydroxystyryl)-1,3,4-thiadiazole | |
| NO162461B (no) | Fremgangsm te for fremstilling av aminderivater. | |
| US3238242A (en) | Process for the preparation of phenyl (meta-and para-tolyl)-propionitriles | |
| CA1054152A (en) | Basic enol ethers, their salts, processes for their preparation and pharmaceutical preparations containing the same | |
| CA1101874A (en) | Thiophene compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEC | Expiry (correction) | ||
| MKEX | Expiry |