LU83830A1 - Neue phenylalkylamine,ihre herstellung und ihre verwendung als arzneimittel - Google Patents
Neue phenylalkylamine,ihre herstellung und ihre verwendung als arzneimittel Download PDFInfo
- Publication number
- LU83830A1 LU83830A1 LU83830A LU83830A LU83830A1 LU 83830 A1 LU83830 A1 LU 83830A1 LU 83830 A LU83830 A LU 83830A LU 83830 A LU83830 A LU 83830A LU 83830 A1 LU83830 A1 LU 83830A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- group
- carbon atoms
- phenyl
- amino
- ethanol
- Prior art date
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- 238000004519 manufacturing process Methods 0.000 title claims description 8
- 229940126601 medicinal product Drugs 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 638
- -1 hydroxymethylene group Chemical group 0.000 claims description 172
- 125000004432 carbon atom Chemical group C* 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 53
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 41
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- 239000001257 hydrogen Substances 0.000 claims description 35
- 239000002253 acid Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 31
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 31
- 239000002904 solvent Substances 0.000 claims description 31
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 239000012279 sodium borohydride Substances 0.000 claims description 29
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 29
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000003277 amino group Chemical group 0.000 claims description 19
- 239000000460 chlorine Chemical group 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 229910052740 iodine Chemical group 0.000 claims description 18
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000012280 lithium aluminium hydride Substances 0.000 claims description 16
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 13
- 150000004678 hydrides Chemical class 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 239000000126 substance Substances 0.000 claims description 13
- 150000001412 amines Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 9
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 9
- 230000003287 optical effect Effects 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 229910052987 metal hydride Inorganic materials 0.000 claims description 8
- 150000004681 metal hydrides Chemical class 0.000 claims description 8
- 230000003647 oxidation Effects 0.000 claims description 8
- 238000007254 oxidation reaction Methods 0.000 claims description 8
- 230000001681 protective effect Effects 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 235000019253 formic acid Nutrition 0.000 claims description 7
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 6
- 230000029936 alkylation Effects 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 6
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 5
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 5
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- 239000003513 alkali Substances 0.000 claims description 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 4
- 239000007800 oxidant agent Substances 0.000 claims description 4
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical group CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000005695 dehalogenation reaction Methods 0.000 claims description 3
- 201000010099 disease Diseases 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000005984 hydrogenation reaction Methods 0.000 claims description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims description 2
- 238000007069 methylation reaction Methods 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims description 2
- 150000003333 secondary alcohols Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 4
- 150000007522 mineralic acids Chemical class 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 150000008051 alkyl sulfates Chemical class 0.000 claims 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- AGDHSWAZTKYTNX-UHFFFAOYSA-N 3-phenyl-n-propan-2-ylpropan-1-amine Chemical compound CC(C)NCCCC1=CC=CC=C1 AGDHSWAZTKYTNX-UHFFFAOYSA-N 0.000 claims 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 125000004414 alkyl thio group Chemical group 0.000 claims 1
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims 1
- 229940125898 compound 5 Drugs 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000006627 ethoxycarbonylamino group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 125000000075 primary alcohol group Chemical group 0.000 claims 1
- QTZZYFLLQVLUNF-UHFFFAOYSA-N sodium;lithium Chemical compound [Li].[Na+] QTZZYFLLQVLUNF-UHFFFAOYSA-N 0.000 claims 1
- 239000008096 xylene Chemical group 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 276
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 176
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 117
- 238000001228 spectrum Methods 0.000 description 114
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 96
- 239000003921 oil Substances 0.000 description 95
- 238000002329 infrared spectrum Methods 0.000 description 69
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 62
- 238000002844 melting Methods 0.000 description 60
- 230000008018 melting Effects 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 55
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 51
- 239000000243 solution Substances 0.000 description 50
- 238000002211 ultraviolet spectrum Methods 0.000 description 47
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 44
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 28
- 239000000203 mixture Substances 0.000 description 24
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 23
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 21
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 19
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 238000003756 stirring Methods 0.000 description 17
- 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 16
- 239000011734 sodium Substances 0.000 description 16
- 229910052708 sodium Inorganic materials 0.000 description 16
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 14
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 230000008020 evaporation Effects 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 10
- BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 241001024304 Mino Species 0.000 description 8
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 101150052863 THY1 gene Proteins 0.000 description 8
- 239000012362 glacial acetic acid Substances 0.000 description 8
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 description 8
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 229910021529 ammonia Inorganic materials 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 6
- 229930040373 Paraformaldehyde Natural products 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 229960003424 phenylacetic acid Drugs 0.000 description 6
- 239000003279 phenylacetic acid Substances 0.000 description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 6
- 238000005245 sintering Methods 0.000 description 6
- 101150041968 CDC13 gene Proteins 0.000 description 5
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 125000000068 chlorophenyl group Chemical group 0.000 description 5
- 238000004140 cleaning Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 229940050176 methyl chloride Drugs 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 229910000104 sodium hydride Inorganic materials 0.000 description 5
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229920002261 Corn starch Polymers 0.000 description 4
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
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Classifications
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- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
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- 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
- C07D295/12—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 or doubly bound nitrogen atoms
- C07D295/135—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 or doubly bound nitrogen atoms with the ring nitrogen atoms and the substituent nitrogen atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
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- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/58—Radicals substituted by nitrogen atoms
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- G11B23/00—Record carriers not specific to the method of recording or reproducing; Accessories, e.g. containers, specially adapted for co-operation with the recording or reproducing apparatus ; Intermediate mediums; Apparatus or processes specially adapted for their manufacture
- G11B23/02—Containers; Storing means both adapted to cooperate with the recording or reproducing means
- G11B23/04—Magazines; Cassettes for webs or filaments
- G11B23/08—Magazines; Cassettes for webs or filaments for housing webs or filaments having two distinct ends
- G11B23/087—Magazines; Cassettes for webs or filaments for housing webs or filaments having two distinct ends using two different reels or cores
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Landscapes
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- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3046465 | 1980-12-10 | ||
| DE3046465 | 1980-12-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU83830A1 true LU83830A1 (de) | 1983-04-13 |
Family
ID=6118763
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU83830A LU83830A1 (de) | 1980-12-10 | 1981-12-10 | Neue phenylalkylamine,ihre herstellung und ihre verwendung als arzneimittel |
Country Status (32)
| Country | Link |
|---|---|
| JP (1) | JPS57122048A (hu) |
| KR (1) | KR870000183B1 (hu) |
| AR (1) | AR227802A1 (hu) |
| AT (1) | AT379378B (hu) |
| AU (1) | AU547655B2 (hu) |
| BE (1) | BE891416A (hu) |
| CA (1) | CA1202636A (hu) |
| CH (1) | CH651541A5 (hu) |
| CS (1) | CS229924B2 (hu) |
| DD (1) | DD202867A5 (hu) |
| DE (1) | DE3146623A1 (hu) |
| DK (1) | DK541981A (hu) |
| ES (4) | ES8301890A1 (hu) |
| FI (1) | FI813934L (hu) |
| FR (1) | FR2498596B1 (hu) |
| GB (1) | GB2088873B (hu) |
| GR (1) | GR77323B (hu) |
| HU (1) | HU185676B (hu) |
| IE (1) | IE52007B1 (hu) |
| IL (1) | IL64498A (hu) |
| IT (1) | IT1172129B (hu) |
| LU (1) | LU83830A1 (hu) |
| NL (1) | NL8105170A (hu) |
| NO (1) | NO152649C (hu) |
| NZ (1) | NZ199215A (hu) |
| PH (1) | PH21599A (hu) |
| PL (1) | PL129385B1 (hu) |
| PT (1) | PT74112B (hu) |
| SE (1) | SE8107387L (hu) |
| SU (1) | SU1172449A3 (hu) |
| YU (1) | YU290381A (hu) |
| ZA (1) | ZA818529B (hu) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4720586A (en) * | 1983-12-06 | 1988-01-19 | Fisons, Plc | Substituted 3,4-dihydroxy-phenylethylamino compounds |
| GB8419963D0 (en) * | 1984-08-06 | 1984-09-12 | Lundbeck & Co As H | Intermediate compound and method |
| US4943591A (en) * | 1984-10-17 | 1990-07-24 | Glaxo Group Limited | Dichloroaniline derivatives |
| GB8426191D0 (en) * | 1984-10-17 | 1984-11-21 | Glaxo Holdings Ltd | Chemical compounds |
| GB8603475D0 (en) * | 1986-02-12 | 1986-03-19 | Glaxo Group Ltd | Chemical compounds |
| JPS63290852A (ja) * | 1987-02-10 | 1988-11-28 | グラクソ、グループ、リミテッド | 化合物 |
| GB8703007D0 (en) * | 1987-02-10 | 1987-03-18 | Glaxo Group Ltd | Chemical compounds |
| US4906645A (en) * | 1988-09-12 | 1990-03-06 | Merck & Co., Inc. | Pyridyl aminoethanol compounds with growth promotion and an increase in feed efficiency |
| DE4028398A1 (de) * | 1990-09-07 | 1992-03-12 | Thomae Gmbh Dr K | Phenylethanolamine, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE69227596T2 (de) * | 1991-10-04 | 1999-04-08 | Taisho Pharmaceutical Co Ltd | Alkoxyphenylalkylaminderivat |
| WO2010059711A1 (en) * | 2008-11-18 | 2010-05-27 | Wisconsin Alumni Research Foundation | Sigma-1 receptor ligands and methods of use |
| GB201208775D0 (en) * | 2012-05-18 | 2012-07-04 | Uni I Oslo | Chemical compounds |
| US10668030B2 (en) * | 2016-04-21 | 2020-06-02 | University Of Kentucky Research Foundation | Vesicular monoamine transporter-2 ligands and their use in the treatment of psychostimulant abuse |
| US11999676B2 (en) | 2016-04-21 | 2024-06-04 | University Of Kentucky Research Foundation | Vesicular monoamine transporter-2 ligands and their use in the treatment of psychostimulant abuse |
| WO2023235153A1 (en) * | 2022-05-31 | 2023-12-07 | Corteva Agriscience Llc | Crystalline forms of picolinamide fungicide compound |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1618007A1 (de) * | 1967-05-09 | 1970-10-29 | Thomae Gmbh Dr K | Verfahren zur Herstellung von neuen Amino-monohalogenphenylaethanolaminen |
| DE2351281C3 (de) * | 1973-10-12 | 1981-07-30 | Dr. Karl Thomae Gmbh, 7950 Biberach | Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung |
| NL176168C (nl) * | 1972-12-18 | 1985-03-01 | Thomae Gmbh Dr K | Werkwijze ter bereiding respectievelijk vervaardiging van een farmaceutisch preparaat en werkwijze ter bereiding van daarbij bruikbare nieuwe gesubstitueerde 1-(4-aminofenyl)-2-amino-ethanol-derivaten die, behalve een analgetische, uterusspasmolytische en anti-spastische werking op de dwarsgestreepte spieren, in het bijzonder een beta2-mimetische en/of beta1-blokkerende werking bezitten. |
| JPS51125232A (en) * | 1975-02-05 | 1976-11-01 | Yamanouchi Pharmaceut Co Ltd | Process for preparing 4-substituted amido-3,5-dihalogeno-alpha-substituted aminomethylbenzyl alcohols |
| GB1523974A (en) * | 1975-02-05 | 1978-09-06 | Yamanouchi Pharma Co Ltd | 4-substituted amino- -aminomethylbenzyl alcohol derivatives |
| DK58679A (da) * | 1978-02-21 | 1979-08-22 | Sandoz Ag | Fremgangsmaade til fremstilling af phenylethylaminer |
| CA1120058A (en) * | 1978-07-03 | 1982-03-16 | Jack Mills | Phenethanolamines, formulations and potentiation of oncolytic drugs |
-
1981
- 1981-11-16 NL NL8105170A patent/NL8105170A/nl not_active Application Discontinuation
- 1981-11-25 DE DE19813146623 patent/DE3146623A1/de not_active Withdrawn
- 1981-11-27 SU SU813358171A patent/SU1172449A3/ru active
- 1981-11-30 AT AT0512981A patent/AT379378B/de not_active IP Right Cessation
- 1981-12-02 ES ES507635A patent/ES8301890A1/es not_active Expired
- 1981-12-07 CH CH7800/81A patent/CH651541A5/de not_active IP Right Cessation
- 1981-12-07 IT IT49853/81A patent/IT1172129B/it active
- 1981-12-07 DD DD81235491A patent/DD202867A5/de unknown
- 1981-12-07 GR GR66712A patent/GR77323B/el unknown
- 1981-12-08 FI FI813934A patent/FI813934L/fi not_active Application Discontinuation
- 1981-12-08 DK DK541981A patent/DK541981A/da not_active Application Discontinuation
- 1981-12-09 AU AU78414/81A patent/AU547655B2/en not_active Ceased
- 1981-12-09 GB GB8137051A patent/GB2088873B/en not_active Expired
- 1981-12-09 IL IL64498A patent/IL64498A/xx unknown
- 1981-12-09 NO NO814194A patent/NO152649C/no unknown
- 1981-12-09 JP JP56198337A patent/JPS57122048A/ja active Pending
- 1981-12-09 IE IE2888/81A patent/IE52007B1/en unknown
- 1981-12-09 NZ NZ199215A patent/NZ199215A/en unknown
- 1981-12-09 SE SE8107387A patent/SE8107387L/xx not_active Application Discontinuation
- 1981-12-09 CA CA000391831A patent/CA1202636A/en not_active Expired
- 1981-12-09 HU HU813708A patent/HU185676B/hu unknown
- 1981-12-09 ZA ZA818529A patent/ZA818529B/xx unknown
- 1981-12-09 PL PL1981234155A patent/PL129385B1/pl unknown
- 1981-12-09 BE BE0/206788A patent/BE891416A/fr not_active IP Right Cessation
- 1981-12-10 FR FR8123106A patent/FR2498596B1/fr not_active Expired
- 1981-12-10 PH PH26726A patent/PH21599A/en unknown
- 1981-12-10 AR AR287754A patent/AR227802A1/es active
- 1981-12-10 CS CS819178A patent/CS229924B2/cs unknown
- 1981-12-10 PT PT74112A patent/PT74112B/pt unknown
- 1981-12-10 KR KR1019810004912A patent/KR870000183B1/ko active IP Right Grant
- 1981-12-10 LU LU83830A patent/LU83830A1/de unknown
- 1981-12-10 YU YU02903/81A patent/YU290381A/xx unknown
-
1982
- 1982-06-08 ES ES512915A patent/ES8304538A1/es not_active Expired
- 1982-06-08 ES ES512913A patent/ES512913A0/es active Granted
- 1982-06-08 ES ES512914A patent/ES512914A0/es active Granted
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