DD243491A5 - Verfahren zur herstellung neuer 3-phenyl-2-propanamin-derivate - Google Patents
Verfahren zur herstellung neuer 3-phenyl-2-propanamin-derivate Download PDFInfo
- Publication number
- DD243491A5 DD243491A5 DD85287682A DD28768285A DD243491A5 DD 243491 A5 DD243491 A5 DD 243491A5 DD 85287682 A DD85287682 A DD 85287682A DD 28768285 A DD28768285 A DD 28768285A DD 243491 A5 DD243491 A5 DD 243491A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- radical
- general formula
- alkyl
- phenyl
- dimethylamino
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical class CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 14
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 14
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 11
- 125000001424 substituent group Chemical group 0.000 claims abstract description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 5
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 4
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 3
- 230000003287 optical effect Effects 0.000 claims abstract description 3
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
- -1 alkyl radical Chemical class 0.000 claims description 67
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 34
- 150000003254 radicals Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 25
- 125000005843 halogen group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 150000001412 amines Chemical class 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000004434 sulfur atom Chemical group 0.000 claims description 13
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical group F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical compound O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- RDAFNSMYPSHCBK-UHFFFAOYSA-N 3-phenylprop-2-en-1-amine Chemical class NCC=CC1=CC=CC=C1 RDAFNSMYPSHCBK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 239000000935 antidepressant agent Substances 0.000 abstract description 5
- 229940005513 antidepressants Drugs 0.000 abstract description 5
- 229910052736 halogen Inorganic materials 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 abstract description 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 2
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 abstract 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 100
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 62
- 239000000243 solution Substances 0.000 description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 38
- 239000007787 solid Substances 0.000 description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 239000013078 crystal Substances 0.000 description 24
- 239000000843 powder Substances 0.000 description 20
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 17
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 16
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 230000008018 melting Effects 0.000 description 11
- 238000002844 melting Methods 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 238000004587 chromatography analysis Methods 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 239000000543 intermediate Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007983 Tris buffer Substances 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
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- OFPSZXABEUGMAH-UHFFFAOYSA-N (4-chloro-1,2-diphenylbut-2-enyl) ethyl carbonate Chemical compound C=1C=CC=CC=1C(OC(=O)OCC)C(=CCCl)C1=CC=CC=C1 OFPSZXABEUGMAH-UHFFFAOYSA-N 0.000 description 4
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
- PQVAFRGRAJGSLP-UHFFFAOYSA-N 4-(dimethylamino)-1,2-diphenylbut-2-en-1-ol Chemical compound C=1C=CC=CC=1C(=CCN(C)C)C(O)C1=CC=CC=C1 PQVAFRGRAJGSLP-UHFFFAOYSA-N 0.000 description 4
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- 230000006978 adaptation Effects 0.000 description 4
- 230000001430 anti-depressive effect Effects 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
- KHNDCBPVBIONAE-UHFFFAOYSA-N (3-chloro-1-phenylprop-1-enyl)sulfanylbenzene Chemical compound C=1C=CC=CC=1C(=CCCl)SC1=CC=CC=C1 KHNDCBPVBIONAE-UHFFFAOYSA-N 0.000 description 3
- DDTDBJYOPYFBQV-UHFFFAOYSA-N (4-amino-1,2-diphenylbut-2-enyl) ethyl carbonate Chemical compound C=1C=CC=CC=1C(OC(=O)OCC)C(=CCN)C1=CC=CC=C1 DDTDBJYOPYFBQV-UHFFFAOYSA-N 0.000 description 3
- HLOUJKQAGQBDCX-UHFFFAOYSA-N (4-azido-1,2-diphenylbut-2-enyl) ethyl carbonate Chemical compound C=1C=CC=CC=1C(OC(=O)OCC)C(=CCN=[N+]=[N-])C1=CC=CC=C1 HLOUJKQAGQBDCX-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- SHPWXAIZADBCLR-UHFFFAOYSA-N 4-amino-1,2-diphenylbut-2-en-1-ol Chemical compound C=1C=CC=CC=1C(=CCN)C(O)C1=CC=CC=C1 SHPWXAIZADBCLR-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CHYXQVPUAVQLTN-UHFFFAOYSA-N [4-(dimethylamino)-1,2-diphenylbut-2-enyl] ethyl carbonate Chemical compound C=1C=CC=CC=1C(OC(=O)OCC)C(=CCN(C)C)C1=CC=CC=C1 CHYXQVPUAVQLTN-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 125000002524 organometallic group Chemical group 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- LDBZHHVGVAIVBT-UHFFFAOYSA-N 1-(3-chlorophenyl)-3-(dimethylamino)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CC(Cl)=C1 LDBZHHVGVAIVBT-UHFFFAOYSA-N 0.000 description 2
- GMHRGALEPZVQKD-UHFFFAOYSA-N 1-cyclohexyl-4-(dimethylamino)-2-phenylbut-2-en-1-ol Chemical compound C=1C=CC=CC=1C(=CCN(C)C)C(O)C1CCCCC1 GMHRGALEPZVQKD-UHFFFAOYSA-N 0.000 description 2
- UGRVYFQFDZRNMQ-UHFFFAOYSA-N 2,4,6-tri(propan-2-yl)benzenesulfonohydrazide Chemical compound CC(C)C1=CC(C(C)C)=C(S(=O)(=O)NN)C(C(C)C)=C1 UGRVYFQFDZRNMQ-UHFFFAOYSA-N 0.000 description 2
- UGACQGVWGMEAEU-UHFFFAOYSA-N 2-(3-chlorophenyl)-4-(dimethylamino)-1-(3-fluorophenyl)but-2-en-1-ol Chemical compound C=1C=CC(Cl)=CC=1C(=CCN(C)C)C(O)C1=CC=CC(F)=C1 UGACQGVWGMEAEU-UHFFFAOYSA-N 0.000 description 2
- YWJFOZWVPZFJQA-UHFFFAOYSA-N 3-(2-chlorophenyl)sulfanyl-n,n-dimethyl-3-phenylprop-2-en-1-amine Chemical compound C=1C=CC=CC=1C(=CCN(C)C)SC1=CC=CC=C1Cl YWJFOZWVPZFJQA-UHFFFAOYSA-N 0.000 description 2
- HUTKDPINCSJXAA-UHFFFAOYSA-N 3-(dimethylamino)-1-phenylprop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC=CC=C1 HUTKDPINCSJXAA-UHFFFAOYSA-N 0.000 description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 2
- RUQLCWAQVDYNCJ-UHFFFAOYSA-N 4-(dimethylamino)-1-(2-fluorophenyl)-2-phenylbut-2-en-1-ol Chemical compound C=1C=CC=CC=1C(=CCN(C)C)C(O)C1=CC=CC=C1F RUQLCWAQVDYNCJ-UHFFFAOYSA-N 0.000 description 2
- CKPGUWZDUCMRBP-UHFFFAOYSA-N 4-(dimethylamino)-1-(2-methylphenyl)-2-phenylbut-2-en-1-ol Chemical compound C=1C=CC=CC=1C(=CCN(C)C)C(O)C1=CC=CC=C1C CKPGUWZDUCMRBP-UHFFFAOYSA-N 0.000 description 2
- HFCMCANFIHDARP-UHFFFAOYSA-N 4-(methylamino)-1,2-diphenylbut-2-en-1-ol Chemical compound C=1C=CC=CC=1C(=CCNC)C(O)C1=CC=CC=C1 HFCMCANFIHDARP-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical class NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 2
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000012948 isocyanate Substances 0.000 description 2
- 150000002513 isocyanates Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 125000002734 organomagnesium group Chemical group 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- JKANAVGODYYCQF-UHFFFAOYSA-N prop-2-yn-1-amine Chemical compound NCC#C JKANAVGODYYCQF-UHFFFAOYSA-N 0.000 description 2
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/20—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an acyclic unsaturated carbon skeleton
- C07C211/21—Monoamines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
-
- 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
- C07D295/092—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 with aromatic radicals attached to the chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D307/32—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Pain & Pain Management (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)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8402338A FR2559765B1 (fr) | 1984-02-16 | 1984-02-16 | Nouveaux derives de la phenyl-3 propene-2 amine, leur preparation et les medicaments qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD243491A5 true DD243491A5 (de) | 1987-03-04 |
Family
ID=9301090
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85287682A DD243491A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propanamin-derivate |
| DD85287135A DD243024A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD85287060A DD243022A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD85287313A DD243277A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD85273319A DD239403A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD86287435A DD243494A5 (de) | 1984-02-16 | 1986-01-14 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD85287135A DD243024A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD85287060A DD243022A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD85287313A DD243277A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD85273319A DD239403A5 (de) | 1984-02-16 | 1985-02-15 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
| DD86287435A DD243494A5 (de) | 1984-02-16 | 1986-01-14 | Verfahren zur herstellung neuer 3-phenyl-2-propenamin-derivate |
Country Status (20)
| Country | Link |
|---|---|
| US (2) | US4686309A (cs) |
| EP (1) | EP0153890B1 (cs) |
| JP (1) | JPS60208948A (cs) |
| KR (1) | KR850006934A (cs) |
| AT (1) | ATE39682T1 (cs) |
| AU (1) | AU576347B2 (cs) |
| CA (1) | CA1250298A (cs) |
| CS (1) | CS252826B2 (cs) |
| DD (6) | DD243491A5 (cs) |
| DE (1) | DE3567201D1 (cs) |
| DK (1) | DK74185A (cs) |
| ES (6) | ES540471A0 (cs) |
| FR (1) | FR2559765B1 (cs) |
| GR (1) | GR850388B (cs) |
| HU (1) | HUT41714A (cs) |
| IL (1) | IL74324A (cs) |
| MA (1) | MA20349A1 (cs) |
| PT (1) | PT79975B (cs) |
| SU (2) | SU1402251A3 (cs) |
| ZA (1) | ZA851127B (cs) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4826844A (en) * | 1987-09-30 | 1989-05-02 | American Home Products Corporation | Substituted 1-(aralkyl-piperazinoalkyl) cycloalkanols |
| US4745191A (en) * | 1987-09-30 | 1988-05-17 | American Home Products Corporation | 1-((A-substituted phenyl-ω-substituted piperazinyl)alkenyl) cyclohexanol |
| US4996235A (en) * | 1987-11-25 | 1991-02-26 | Eli Lilly And Company | 3,4-diphenylbutanamines |
| US4902710A (en) * | 1988-12-14 | 1990-02-20 | Eli Lilly And Company | Serotonin and norepinephrine uptake inhibitors |
| DE19609847A1 (de) * | 1996-03-13 | 1997-09-18 | Gruenenthal Gmbh | Dimethyl-(3-aryl-but-3-enyl)-aminverbindungen als pharmazeutische Wirkstoffe |
| DE10048714A1 (de) * | 2000-09-30 | 2002-04-11 | Gruenenthal Gmbh | 5-Amino-1-penlen-3-ol-Derivate |
| US20050176136A1 (en) * | 2003-11-19 | 2005-08-11 | Dexcom, Inc. | Afinity domain for analyte sensor |
| CN103819400B (zh) * | 2013-09-16 | 2016-05-04 | 江西师范大学 | 一种多组分反应合成具有不对称结构1.4-二氢吡啶及其衍生物的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3978129A (en) * | 1972-01-28 | 1976-08-31 | A. H. Robins Company, Incorporated | Alkenyl- and alkanylamines |
| US4056630A (en) * | 1973-02-24 | 1977-11-01 | Beecham Group Limited | Diphenylpropylamines for treating depression |
| US4018895A (en) * | 1974-01-10 | 1977-04-19 | Eli Lilly And Company | Aryloxyphenylpropylamines in treating depression |
| US4018845A (en) * | 1975-06-06 | 1977-04-19 | Uop Inc. | Hydrocarbon isomerization process |
| JPS5896045A (ja) * | 1981-11-30 | 1983-06-07 | Sumitomo Chem Co Ltd | 新規なジフエニルアルカノアミン誘導体およびその製造法 |
-
1984
- 1984-02-16 FR FR8402338A patent/FR2559765B1/fr not_active Expired
-
1985
- 1985-02-08 MA MA20573A patent/MA20349A1/fr unknown
- 1985-02-12 IL IL74324A patent/IL74324A/xx unknown
- 1985-02-13 GR GR850388A patent/GR850388B/el unknown
- 1985-02-14 AT AT85400254T patent/ATE39682T1/de active
- 1985-02-14 AU AU38726/85A patent/AU576347B2/en not_active Ceased
- 1985-02-14 ZA ZA851127A patent/ZA851127B/xx unknown
- 1985-02-14 EP EP85400254A patent/EP0153890B1/fr not_active Expired
- 1985-02-14 DE DE8585400254T patent/DE3567201D1/de not_active Expired
- 1985-02-15 US US06/702,088 patent/US4686309A/en not_active Expired - Fee Related
- 1985-02-15 DD DD85287682A patent/DD243491A5/de unknown
- 1985-02-15 DK DK74185A patent/DK74185A/da not_active Application Discontinuation
- 1985-02-15 HU HU85576A patent/HUT41714A/hu unknown
- 1985-02-15 KR KR1019850000935A patent/KR850006934A/ko not_active Withdrawn
- 1985-02-15 CA CA000474436A patent/CA1250298A/fr not_active Expired
- 1985-02-15 DD DD85287135A patent/DD243024A5/de unknown
- 1985-02-15 DD DD85287060A patent/DD243022A5/de unknown
- 1985-02-15 CS CS851089A patent/CS252826B2/cs unknown
- 1985-02-15 ES ES540471A patent/ES540471A0/es active Granted
- 1985-02-15 JP JP60028164A patent/JPS60208948A/ja active Pending
- 1985-02-15 PT PT79975A patent/PT79975B/pt unknown
- 1985-02-15 DD DD85287313A patent/DD243277A5/de unknown
- 1985-02-15 DD DD85273319A patent/DD239403A5/de unknown
- 1985-07-17 ES ES545314A patent/ES8604519A1/es not_active Expired
- 1985-07-17 ES ES545313A patent/ES8604486A1/es not_active Expired
- 1985-07-17 ES ES545310A patent/ES8700224A1/es not_active Expired
- 1985-07-17 ES ES545312A patent/ES8604485A1/es not_active Expired
- 1985-07-17 ES ES545311A patent/ES8604484A1/es not_active Expired
-
1986
- 1986-01-14 DD DD86287435A patent/DD243494A5/de unknown
- 1986-03-14 SU SU864027084A patent/SU1402251A3/ru active
- 1986-03-14 SU SU864027077A patent/SU1391495A3/ru active
-
1987
- 1987-02-03 US US07/010,558 patent/US4755599A/en not_active Expired - Fee Related
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