FI67216C - Foerfarande foer framstaellning av terapeutiskt anvaendbara 1,-ditiolanyl(2)- och 1,3-ditianyl(2)-foereningar - Google Patents
Foerfarande foer framstaellning av terapeutiskt anvaendbara 1,-ditiolanyl(2)- och 1,3-ditianyl(2)-foereningar Download PDFInfo
- Publication number
- FI67216C FI67216C FI3527/74A FI352774A FI67216C FI 67216 C FI67216 C FI 67216C FI 3527/74 A FI3527/74 A FI 3527/74A FI 352774 A FI352774 A FI 352774A FI 67216 C FI67216 C FI 67216C
- Authority
- FI
- Finland
- Prior art keywords
- dithian
- methyl
- dimethoxyphenethyl
- propylamine
- compound
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 130
- -1 methylenedioxy, ethylenedioxy Chemical group 0.000 claims description 64
- 239000002253 acid Substances 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 229910052727 yttrium Inorganic materials 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- ILWJAOPQHOZXAN-UHFFFAOYSA-N 1,3-dithianyl Chemical group [CH]1SCCCS1 ILWJAOPQHOZXAN-UHFFFAOYSA-N 0.000 claims description 3
- LERKMAFHYXHGCO-UHFFFAOYSA-N 5-[2-(3,4-dimethoxyphenyl)-1,3-dithian-2-yl]-n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methylpentan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCCCC1(C=2C=C(OC)C(OC)=CC=2)SCCCS1 LERKMAFHYXHGCO-UHFFFAOYSA-N 0.000 claims description 3
- ZROUQTNYPCANTN-UHFFFAOYSA-N Tiapamil Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C(OC)C(OC)=CC=2)S(=O)(=O)CCCS1(=O)=O ZROUQTNYPCANTN-UHFFFAOYSA-N 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- FLOJNXXFMHCMMR-UHFFFAOYSA-N 1,3-dithiolanyl Chemical group [CH]1SCCS1 FLOJNXXFMHCMMR-UHFFFAOYSA-N 0.000 claims description 2
- CQPADMCCOBLYBU-UHFFFAOYSA-N C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC(C)=CC=2)S(=O)(=O)CCCS1(=O)=O Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC(C)=CC=2)S(=O)(=O)CCCS1(=O)=O CQPADMCCOBLYBU-UHFFFAOYSA-N 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 230000001590 oxidative effect Effects 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- JLHAICPRACKIFB-UHFFFAOYSA-N C=1C=C(OC)C(OC)=CC=1CCN(CC)CCCC1(C=2C=C(OC)C(OC)=CC=2)S(=O)(=O)CCCS1(=O)=O Chemical compound C=1C=C(OC)C(OC)=CC=1CCN(CC)CCCC1(C=2C=C(OC)C(OC)=CC=2)S(=O)(=O)CCCS1(=O)=O JLHAICPRACKIFB-UHFFFAOYSA-N 0.000 claims 1
- VZFKQPFXWPKCEY-UHFFFAOYSA-N N-[2-(3,4-dimethoxyphenyl)ethyl]-3-[2-(4-methoxyphenyl)-1,3-dithian-2-yl]-N-methylpropan-1-amine Chemical compound COC=1C=C(C=CC1OC)CCN(CCCC1(SCCCS1)C1=CC=C(C=C1)OC)C VZFKQPFXWPKCEY-UHFFFAOYSA-N 0.000 claims 1
- YEXYNWAZYPPKQD-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-(2-naphthalen-2-yl-1,3-dithian-2-yl)propan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C3C=CC=CC3=CC=2)SCCCS1 YEXYNWAZYPPKQD-UHFFFAOYSA-N 0.000 claims 1
- KYWLWDDYCGVZCY-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-(2-phenyl-1,3-dithian-2-yl)propan-1-amine Chemical compound C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC=CC=2)SCCCS1 KYWLWDDYCGVZCY-UHFFFAOYSA-N 0.000 claims 1
- CESARNHNESBGSG-UHFFFAOYSA-N n-[2-(4-chlorophenyl)ethyl]-n-methyl-3-(2-phenyl-1,3-dithian-2-yl)propan-1-amine Chemical compound C=1C=C(Cl)C=CC=1CCN(C)CCCC1(C=2C=CC=CC=2)SCCCS1 CESARNHNESBGSG-UHFFFAOYSA-N 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 183
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 69
- 239000000203 mixture Substances 0.000 description 62
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 51
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 48
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 46
- 238000006243 chemical reaction Methods 0.000 description 37
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 35
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 28
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000007858 starting material Substances 0.000 description 27
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- HNJWKRMESUMDQE-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-n-methylethanamine Chemical compound CNCCC1=CC=C(OC)C(OC)=C1 HNJWKRMESUMDQE-UHFFFAOYSA-N 0.000 description 18
- 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 18
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 18
- 238000009835 boiling Methods 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000002585 base Substances 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 229960000583 acetic acid Drugs 0.000 description 15
- 239000000284 extract Substances 0.000 description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 14
- 239000012362 glacial acetic acid Substances 0.000 description 14
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 14
- 235000019341 magnesium sulphate Nutrition 0.000 description 14
- 230000009467 reduction Effects 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
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- 239000003960 organic solvent Substances 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- 230000008020 evaporation Effects 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- 239000002244 precipitate Substances 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 8
- 238000004458 analytical method Methods 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- 150000002170 ethers Chemical class 0.000 description 6
- 239000012280 lithium aluminium hydride Substances 0.000 description 6
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- CATQBTMIAAXXND-UHFFFAOYSA-N 2-(3-chloropropyl)-2-(3,4-dimethoxyphenyl)-1,3-dithiane 1,1,3,3-tetraoxide Chemical compound C1=C(OC)C(OC)=CC=C1C1(CCCCl)S(=O)(=O)CCCS1(=O)=O CATQBTMIAAXXND-UHFFFAOYSA-N 0.000 description 5
- GXKPARDRBFURON-UHFFFAOYSA-N 2-phenyl-1,3-dithiane Chemical compound S1CCCSC1C1=CC=CC=C1 GXKPARDRBFURON-UHFFFAOYSA-N 0.000 description 5
- HJBBKVHYQQUPQW-UHFFFAOYSA-N 3-chloro-n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methylpropan-1-amine Chemical compound COC1=CC=C(CCN(C)CCCCl)C=C1OC HJBBKVHYQQUPQW-UHFFFAOYSA-N 0.000 description 5
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 5
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- 238000003756 stirring Methods 0.000 description 5
- 150000003512 tertiary amines Chemical class 0.000 description 5
- BYSFFOIEDQTZBD-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,3-dithiane Chemical compound C1=C(OC)C(OC)=CC=C1C1SCCCS1 BYSFFOIEDQTZBD-UHFFFAOYSA-N 0.000 description 4
- ODNGPQOKPLSWSJ-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1,3-dithiane 1,1,3,3-tetraoxide Chemical compound C1=C(OC)C(OC)=CC=C1C1S(=O)(=O)CCCS1(=O)=O ODNGPQOKPLSWSJ-UHFFFAOYSA-N 0.000 description 4
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- FJBDKCRAJPUCAJ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-[2-(3-methoxyphenyl)-1,3-dithian-2-yl]-n-methylpropan-1-amine;hydrochloride Chemical compound Cl.COC1=CC=CC(C2(CCCN(C)CCC=3C=C(OC)C(OC)=CC=3)SCCCS2)=C1 FJBDKCRAJPUCAJ-UHFFFAOYSA-N 0.000 description 1
- JLHUTWRIPVISTP-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-[2-(4-ethoxy-3-methoxyphenyl)-1,1,3,3-tetraoxo-1,3-dithian-2-yl]-n-methylpropan-1-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OCC)=CC=C1C1(CCCN(C)CCC=2C=C(OC)C(OC)=CC=2)S(=O)(=O)CCCS1(=O)=O JLHUTWRIPVISTP-UHFFFAOYSA-N 0.000 description 1
- NSNQCUMVSAEJDO-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-3-[2-(4-fluorophenyl)-1,1,3,3-tetraoxo-1,3-dithian-2-yl]-n-methylpropan-1-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC(F)=CC=2)S(=O)(=O)CCCS1(=O)=O NSNQCUMVSAEJDO-UHFFFAOYSA-N 0.000 description 1
- WRZOZSIQWLBJGB-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-(2-naphthalen-2-yl-1,1,3,3-tetraoxo-1,3-dithian-2-yl)propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C3C=CC=CC3=CC=2)S(=O)(=O)CCCS1(=O)=O WRZOZSIQWLBJGB-UHFFFAOYSA-N 0.000 description 1
- JRDMPXLLFKYYHX-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-(2-phenyl-1,3-dithian-2-yl)propan-1-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC=CC=2)SCCCS1 JRDMPXLLFKYYHX-UHFFFAOYSA-N 0.000 description 1
- ZKDHNCJBUZHARE-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[1,1,3,3-tetraoxo-2-(3,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C(OC)C(OC)=C(OC)C=2)S(=O)(=O)CCCS1(=O)=O ZKDHNCJBUZHARE-UHFFFAOYSA-N 0.000 description 1
- NZWLTVKBMLSXET-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[1,1,3,3-tetraoxo-2-[3-(trifluoromethyl)phenyl]-1,3-dithian-2-yl]propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=C(C=CC=2)C(F)(F)F)S(=O)(=O)CCCS1(=O)=O NZWLTVKBMLSXET-UHFFFAOYSA-N 0.000 description 1
- CQCGVYAMKCVRHZ-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[2-(2,4,5-trimethoxyphenyl)-1,3-dithian-2-yl]propan-1-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C(=CC(OC)=C(OC)C=2)OC)SCCCS1 CQCGVYAMKCVRHZ-UHFFFAOYSA-N 0.000 description 1
- NYONNZFKOGSEPO-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[2-(4-methylphenyl)-1,1,3,3-tetraoxo-1,3-dithian-2-yl]propan-1-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC(C)=CC=2)S(=O)(=O)CCCS1(=O)=O NYONNZFKOGSEPO-UHFFFAOYSA-N 0.000 description 1
- QASRZNOZHWAOGF-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[2-(4-methylphenyl)-1,3-dithian-2-yl]propan-1-amine;hydrochloride Chemical compound Cl.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC(C)=CC=2)SCCCS1 QASRZNOZHWAOGF-UHFFFAOYSA-N 0.000 description 1
- NBHWTCMBHOEVPD-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-n-methyl-3-[2-(4-phenylphenyl)-1,3-dithian-2-yl]propan-1-amine;oxalic acid Chemical compound OC(=O)C(O)=O.C1=C(OC)C(OC)=CC=C1CCN(C)CCCC1(C=2C=CC(=CC=2)C=2C=CC=CC=2)SCCCS1 NBHWTCMBHOEVPD-UHFFFAOYSA-N 0.000 description 1
- OPPAVYVGRMIILS-UHFFFAOYSA-N n-methyl-3-(2-phenyl-1,3-dithian-2-yl)-n-(2-phenylethyl)propan-1-amine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1CCN(C)CCCC1(C=2C=CC=CC=2)SCCCS1 OPPAVYVGRMIILS-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- NCNISYUOWMIOPI-UHFFFAOYSA-N propane-1,1-dithiol Chemical compound CCC(S)S NCNISYUOWMIOPI-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003459 sulfonic acid esters Chemical class 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
- 230000001960 triggered effect Effects 0.000 description 1
- 230000000304 vasodilatating effect Effects 0.000 description 1
- ABDKAPXRBAPSQN-UHFFFAOYSA-N veratrole Chemical compound COC1=CC=CC=C1OC ABDKAPXRBAPSQN-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/46—Friedel-Crafts reactions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/02—Five-membered rings
- C07D339/06—Five-membered rings having the hetero atoms in positions 1 and 3, e.g. cyclic dithiocarbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- General Health & Medical Sciences (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1803073 | 1973-12-21 | ||
| CH1803073A CH611614A5 (en) | 1973-12-21 | 1973-12-21 | Process for the preparation of heterocyclic compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI352774A7 FI352774A7 (no) | 1975-06-22 |
| FI67216B FI67216B (fi) | 1984-10-31 |
| FI67216C true FI67216C (fi) | 1985-02-11 |
Family
ID=4429892
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI3527/74A FI67216C (fi) | 1973-12-21 | 1974-12-05 | Foerfarande foer framstaellning av terapeutiskt anvaendbara 1,-ditiolanyl(2)- och 1,3-ditianyl(2)-foereningar |
| FI801053A FI801053A7 (fi) | 1973-12-21 | 1980-04-02 | Heterosyklisiä yhdisteitä. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI801053A FI801053A7 (fi) | 1973-12-21 | 1980-04-02 | Heterosyklisiä yhdisteitä. |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS595594B2 (no) |
| AT (5) | AT344693B (no) |
| AU (1) | AU511714B2 (no) |
| BE (1) | BE823625A (no) |
| CA (4) | CA1057295A (no) |
| CH (3) | CH611614A5 (no) |
| DD (1) | DD116829A5 (no) |
| DE (2) | DE2463173C2 (no) |
| DK (1) | DK148323C (no) |
| ES (5) | ES433172A1 (no) |
| FI (2) | FI67216C (no) |
| FR (1) | FR2255064B1 (no) |
| GB (3) | GB1489087A (no) |
| HK (1) | HK43380A (no) |
| HU (1) | HU170429B (no) |
| IE (1) | IE40788B1 (no) |
| IL (3) | IL46146A (no) |
| LU (1) | LU71530A1 (no) |
| NL (1) | NL158496B (no) |
| NO (1) | NO142669C (no) |
| PH (3) | PH19393A (no) |
| SE (2) | SE415763B (no) |
| YU (1) | YU39311B (no) |
| ZA (1) | ZA747526B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2515173A1 (fr) * | 1981-10-28 | 1983-04-29 | Delalande Sa | Nouveaux derives du benzaldehyde 3-4-diethere et leur procede de preparation |
| JPS60142297U (ja) * | 1984-02-29 | 1985-09-20 | 株式会社豊田自動織機製作所 | フオ−クリフトにおける旋回型運転席の回転装置 |
| JPS62171328U (no) * | 1986-04-23 | 1987-10-30 | ||
| DE3642331A1 (de) * | 1986-12-11 | 1988-06-23 | Basf Ag | Basisch substituierte phenylacetonitrile, ihre herstellung und diese enthaltende arzneimittel |
| US5434179A (en) * | 1989-06-06 | 1995-07-18 | Takeda Chemical Industries, Ltd. | Method for improving brain function using cholinesterase-inhibiting aminoketone compounds |
| US7132547B2 (en) | 2001-12-28 | 2006-11-07 | Takeda Pharmaceutical Company Limited | Preventives/remedies for urinary disturbance |
| US20100137403A1 (en) * | 2008-07-10 | 2010-06-03 | Scott Malstrom | Method for enhancing cognition or inhibiting cognitive decline |
-
1973
- 1973-12-21 CH CH1803073A patent/CH611614A5/xx not_active IP Right Cessation
-
1974
- 1974-07-19 PH PH20012A patent/PH19393A/en unknown
- 1974-11-25 ZA ZA00747526A patent/ZA747526B/xx unknown
- 1974-11-28 IL IL46146A patent/IL46146A/xx unknown
- 1974-12-05 FI FI3527/74A patent/FI67216C/fi active
- 1974-12-09 IE IE2531/74A patent/IE40788B1/xx unknown
- 1974-12-17 PH PH16639A patent/PH13326A/en unknown
- 1974-12-18 CA CA216,313A patent/CA1057295A/en not_active Expired
- 1974-12-18 NL NL7416507.A patent/NL158496B/xx not_active IP Right Cessation
- 1974-12-18 YU YU3368/74A patent/YU39311B/xx unknown
- 1974-12-19 DD DD183214A patent/DD116829A5/xx unknown
- 1974-12-19 DK DK668174A patent/DK148323C/da not_active IP Right Cessation
- 1974-12-19 LU LU71530A patent/LU71530A1/xx unknown
- 1974-12-19 SE SE7416086A patent/SE415763B/xx not_active IP Right Cessation
- 1974-12-20 NO NO744615A patent/NO142669C/no unknown
- 1974-12-20 GB GB23144/77A patent/GB1489087A/en not_active Expired
- 1974-12-20 GB GB55146/74A patent/GB1489086A/en not_active Expired
- 1974-12-20 ES ES433172A patent/ES433172A1/es not_active Expired
- 1974-12-20 DE DE2463173A patent/DE2463173C2/de not_active Expired
- 1974-12-20 HU HUHO1757A patent/HU170429B/hu unknown
- 1974-12-20 JP JP49145875A patent/JPS595594B2/ja not_active Expired
- 1974-12-20 GB GB23143/77A patent/GB1489088A/en not_active Expired
- 1974-12-20 DE DE2460593A patent/DE2460593C3/de not_active Expired
- 1974-12-20 AT AT1022674A patent/AT344693B/de not_active IP Right Cessation
- 1974-12-20 BE BE151729A patent/BE823625A/xx not_active IP Right Cessation
- 1974-12-23 FR FR7442521A patent/FR2255064B1/fr not_active Expired
-
1976
- 1976-09-01 ES ES451134A patent/ES451134A1/es not_active Expired
- 1976-09-01 ES ES451135A patent/ES451135A1/es not_active Expired
- 1976-09-01 ES ES451136A patent/ES451136A1/es not_active Expired
- 1976-09-01 ES ES451137A patent/ES451137A1/es not_active Expired
-
1977
- 1977-07-19 PH PH20013A patent/PH13396A/en unknown
- 1977-08-29 IL IL52843A patent/IL52843A0/xx not_active IP Right Cessation
- 1977-08-29 IL IL52844A patent/IL52844A0/xx unknown
-
1978
- 1978-01-06 AU AU32242/78A patent/AU511714B2/en not_active Expired
- 1978-01-19 AT AT38778A patent/AT349012B/de not_active IP Right Cessation
- 1978-01-19 AT AT38878A patent/AT349013B/de not_active IP Right Cessation
- 1978-01-19 AT AT38978A patent/AT350053B/de not_active IP Right Cessation
- 1978-01-19 AT AT39178A patent/AT349014B/de not_active IP Right Cessation
- 1978-04-27 SE SE7804879A patent/SE434746B/sv not_active IP Right Cessation
- 1978-06-15 CH CH654178A patent/CH620921A5/de not_active IP Right Cessation
- 1978-06-15 CH CH654078A patent/CH620920A5/de not_active IP Right Cessation
-
1979
- 1979-03-26 CA CA324,131A patent/CA1079290A/en not_active Expired
- 1979-03-26 CA CA324,130A patent/CA1086320A/en not_active Expired
- 1979-03-26 CA CA324,132A patent/CA1072966A/en not_active Expired
-
1980
- 1980-04-02 FI FI801053A patent/FI801053A7/fi not_active Application Discontinuation
- 1980-08-14 HK HK433/80A patent/HK43380A/xx unknown
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