BG61056B2 - Заместени пропаноламинови и морфолинови производни - Google Patents
Заместени пропаноламинови и морфолинови производни Download PDFInfo
- Publication number
- BG61056B2 BG61056B2 BG098513A BG9851394A BG61056B2 BG 61056 B2 BG61056 B2 BG 61056B2 BG 098513 A BG098513 A BG 098513A BG 9851394 A BG9851394 A BG 9851394A BG 61056 B2 BG61056 B2 BG 61056B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- phenoxy
- methyl
- methoxy
- morpholine
- benzyl
- Prior art date
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- 150000002780 morpholines Chemical class 0.000 title description 6
- 150000003152 propanolamines Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 228
- 239000000935 antidepressant agent Substances 0.000 claims abstract description 4
- 229940005513 antidepressants Drugs 0.000 claims abstract description 4
- -1 2-ethoxyphenoxy Chemical group 0.000 claims description 147
- 239000000203 mixture Substances 0.000 claims description 122
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 44
- 238000000034 method Methods 0.000 claims description 42
- 150000003839 salts Chemical class 0.000 claims description 31
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 28
- 238000002360 preparation method Methods 0.000 claims description 27
- 230000009467 reduction Effects 0.000 claims description 25
- 238000006722 reduction reaction Methods 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 11
- 238000007363 ring formation reaction Methods 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 6
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- RJSYPKWVIJGNLO-UHFFFAOYSA-N CCOClOC Chemical compound CCOClOC RJSYPKWVIJGNLO-UHFFFAOYSA-N 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- TWCIUSHYTJSYBR-UHFFFAOYSA-N 1-(2-chlorophenyl)-1-(2-ethoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound CCOC1=CC=CC=C1OC(C(O)CNC)C1=CC=CC=C1Cl TWCIUSHYTJSYBR-UHFFFAOYSA-N 0.000 claims description 3
- CXKJYAQAJNKLMM-UHFFFAOYSA-N 1-(2-methoxyphenoxy)-3-(methylamino)-1-[4-(trifluoromethyl)phenyl]propan-2-ol Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C(O)CNC)OC1=CC=CC=C1OC CXKJYAQAJNKLMM-UHFFFAOYSA-N 0.000 claims description 3
- KQQJTWCMYHRUNO-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1-(2-ethoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound CCOC1=CC=CC=C1OC(C(O)CNC)C1=CC=C(Cl)C(Cl)=C1 KQQJTWCMYHRUNO-UHFFFAOYSA-N 0.000 claims description 3
- OUUJVXDNKNIJCD-UHFFFAOYSA-N 1-(3,4-dichlorophenyl)-1-(2-methoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(O)CNC)OC1=CC=CC=C1OC OUUJVXDNKNIJCD-UHFFFAOYSA-N 0.000 claims description 3
- FYOGDVVFPCEJCH-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-(2-methoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound C=1C=CC(Cl)=CC=1C(C(O)CNC)OC1=CC=CC=C1OC FYOGDVVFPCEJCH-UHFFFAOYSA-N 0.000 claims description 3
- COWCLJGORHWMAU-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3-(methylamino)-1-phenylpropan-2-ol Chemical compound C=1C=CC=CC=1C(C(O)CNC)OC1=CC=C(Cl)C=C1 COWCLJGORHWMAU-UHFFFAOYSA-N 0.000 claims description 3
- BFWCANQXUYEFLH-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-(2-ethoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound CCOC1=CC=CC=C1OC(C(O)CNC)C1=CC=C(Cl)C=C1 BFWCANQXUYEFLH-UHFFFAOYSA-N 0.000 claims description 3
- QLNPTAKPHJHHBI-UHFFFAOYSA-N 1-(4-chlorophenyl)-1-(2-methoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound C=1C=C(Cl)C=CC=1C(C(O)CNC)OC1=CC=CC=C1OC QLNPTAKPHJHHBI-UHFFFAOYSA-N 0.000 claims description 3
- ZZOKZBZOODPZFP-UHFFFAOYSA-N 2-[phenoxy(phenyl)methyl]morpholine Chemical compound C1NCCOC1C(C=1C=CC=CC=1)OC1=CC=CC=C1 ZZOKZBZOODPZFP-UHFFFAOYSA-N 0.000 claims description 3
- JWMBBEUWFPTUGO-UHFFFAOYSA-N 2-methoxy-3-(2-methoxyphenoxy)-n-methyl-3-[4-(trifluoromethyl)phenyl]propan-1-amine Chemical compound C=1C=C(C(F)(F)F)C=CC=1C(C(OC)CNC)OC1=CC=CC=C1OC JWMBBEUWFPTUGO-UHFFFAOYSA-N 0.000 claims description 3
- TYPDTPUNFBSWEA-UHFFFAOYSA-N 2-methoxy-3-(2-methoxyphenoxy)-n-methyl-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(OC)CNC)OC1=CC=CC=C1OC TYPDTPUNFBSWEA-UHFFFAOYSA-N 0.000 claims description 3
- HEXQGAFLRYIIIU-UHFFFAOYSA-N 2-methoxy-n-methyl-3-phenoxy-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(OC)CNC)OC1=CC=CC=C1 HEXQGAFLRYIIIU-UHFFFAOYSA-N 0.000 claims description 3
- FXDIELOGQYMTIV-UHFFFAOYSA-N 3-(1,3-benzodioxol-5-yloxy)-2-methoxy-n-methyl-3-phenylpropan-1-amine Chemical compound C=1C=C2OCOC2=CC=1OC(C(OC)CNC)C1=CC=CC=C1 FXDIELOGQYMTIV-UHFFFAOYSA-N 0.000 claims description 3
- ZXFAZONLOCMIAN-UHFFFAOYSA-N 3-(2-chlorophenyl)-3-(2-ethoxyphenoxy)-2-methoxy-n-methylpropan-1-amine Chemical compound CCOC1=CC=CC=C1OC(C(CNC)OC)C1=CC=CC=C1Cl ZXFAZONLOCMIAN-UHFFFAOYSA-N 0.000 claims description 3
- XGACUQOULOCEJW-UHFFFAOYSA-N 3-(2-ethoxyphenoxy)-2-methoxy-n-methyl-3-phenylpropan-1-amine Chemical compound CCOC1=CC=CC=C1OC(C(CNC)OC)C1=CC=CC=C1 XGACUQOULOCEJW-UHFFFAOYSA-N 0.000 claims description 3
- XZNAQDAONAMRLY-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-2-methoxy-3-(2-methoxyphenoxy)-n-methylpropan-1-amine Chemical compound C=1C=C(Cl)C(Cl)=CC=1C(C(OC)CNC)OC1=CC=CC=C1OC XZNAQDAONAMRLY-UHFFFAOYSA-N 0.000 claims description 3
- GHOWGZFJHDUWJS-UHFFFAOYSA-N 3-(3-chlorophenyl)-3-(2-ethoxyphenoxy)-2-methoxy-n-methylpropan-1-amine Chemical compound CCOC1=CC=CC=C1OC(C(CNC)OC)C1=CC=CC(Cl)=C1 GHOWGZFJHDUWJS-UHFFFAOYSA-N 0.000 claims description 3
- IADKWGUDBSSMLG-UHFFFAOYSA-N 3-(4-chlorophenoxy)-2-methoxy-n-methyl-3-phenylpropan-1-amine Chemical compound C=1C=CC=CC=1C(C(OC)CNC)OC1=CC=C(Cl)C=C1 IADKWGUDBSSMLG-UHFFFAOYSA-N 0.000 claims description 3
- FIDVWNBOKNAEKY-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-methoxy-3-(2-methoxyphenoxy)-n-methylpropan-1-amine Chemical compound C=1C=C(Cl)C=CC=1C(C(OC)CNC)OC1=CC=CC=C1OC FIDVWNBOKNAEKY-UHFFFAOYSA-N 0.000 claims description 3
- WIGGVXFJHLMEEF-UHFFFAOYSA-N 3-(4-chlorophenyl)-3-(2-ethoxyphenoxy)-2-methoxy-n-methylpropan-1-amine Chemical compound CCOC1=CC=CC=C1OC(C(CNC)OC)C1=CC=C(Cl)C=C1 WIGGVXFJHLMEEF-UHFFFAOYSA-N 0.000 claims description 3
- ZGLQATIREDVCAS-UHFFFAOYSA-N 3-(methylamino)-1-phenoxy-1-phenylpropan-2-ol Chemical compound C=1C=CC=CC=1C(C(O)CNC)OC1=CC=CC=C1 ZGLQATIREDVCAS-UHFFFAOYSA-N 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- 229910052700 potassium Inorganic materials 0.000 claims description 3
- YVJORJBZWDVQDX-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yloxy)-3-(methylamino)-1-phenylpropan-2-ol Chemical compound C=1C=C2OCOC2=CC=1OC(C(O)CNC)C1=CC=CC=C1 YVJORJBZWDVQDX-UHFFFAOYSA-N 0.000 claims description 2
- LBTMITASNVAIGI-UHFFFAOYSA-N 1-(2-chlorophenyl)-1-(2-methoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound C=1C=CC=C(Cl)C=1C(C(O)CNC)OC1=CC=CC=C1OC LBTMITASNVAIGI-UHFFFAOYSA-N 0.000 claims description 2
- PEZKUCRACGWNFT-UHFFFAOYSA-N 1-(2-ethoxyphenoxy)-3-(methylamino)-1-phenylpropan-2-ol Chemical compound CCOC1=CC=CC=C1OC(C(O)CNC)C1=CC=CC=C1 PEZKUCRACGWNFT-UHFFFAOYSA-N 0.000 claims description 2
- CHUYSUQFSSGZLB-UHFFFAOYSA-N 1-(3-chlorophenyl)-1-(2-ethoxyphenoxy)-3-(methylamino)propan-2-ol Chemical compound CCOC1=CC=CC=C1OC(C(O)CNC)C1=CC=CC(Cl)=C1 CHUYSUQFSSGZLB-UHFFFAOYSA-N 0.000 claims description 2
- PSQXTCVLHUNXDB-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-methoxy-3-(2-methoxyphenoxy)-n-methylpropan-1-amine Chemical compound C=1C=CC=C(Cl)C=1C(C(OC)CNC)OC1=CC=CC=C1OC PSQXTCVLHUNXDB-UHFFFAOYSA-N 0.000 claims description 2
- YNXZJBQMPWDBEI-UHFFFAOYSA-N 3-(2-chlorophenyl)-2-methoxy-n-methyl-3-phenoxypropan-1-amine Chemical compound C=1C=CC=C(Cl)C=1C(C(OC)CNC)OC1=CC=CC=C1 YNXZJBQMPWDBEI-UHFFFAOYSA-N 0.000 claims description 2
- FGRVCIDDMRDVEP-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-3-(2-ethoxyphenoxy)-2-methoxy-n-methylpropan-1-amine Chemical compound CCOC1=CC=CC=C1OC(C(CNC)OC)C1=CC=C(Cl)C(Cl)=C1 FGRVCIDDMRDVEP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052777 Praseodymium Inorganic materials 0.000 claims description 2
- 230000001430 anti-depressive effect Effects 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 230000002265 prevention Effects 0.000 claims description 2
- 238000006476 reductive cyclization reaction Methods 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- GZKLUZUJZGXMPU-UHFFFAOYSA-N 3-(2-ethoxyphenoxy)-2-methoxy-n-methyl-3-[4-(trifluoromethyl)phenyl]propan-1-amine Chemical compound CCOC1=CC=CC=C1OC(C(CNC)OC)C1=CC=C(C(F)(F)F)C=C1 GZKLUZUJZGXMPU-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 154
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 102
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 72
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 70
- 239000000243 solution Substances 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
- 239000002904 solvent Substances 0.000 description 55
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 50
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 45
- 235000019441 ethanol Nutrition 0.000 description 42
- 239000011734 sodium Substances 0.000 description 35
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 238000003756 stirring Methods 0.000 description 28
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 27
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 27
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 26
- 239000003921 oil Substances 0.000 description 25
- 238000010992 reflux Methods 0.000 description 25
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 25
- 235000019439 ethyl acetate Nutrition 0.000 description 24
- 239000000460 chlorine Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 21
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002585 base Substances 0.000 description 18
- 230000002829 reductive effect Effects 0.000 description 17
- 239000000284 extract Substances 0.000 description 15
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 14
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 13
- 230000008020 evaporation Effects 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 12
- 229910000104 sodium hydride Inorganic materials 0.000 description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical group CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- 229910010082 LiAlH Inorganic materials 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000012299 nitrogen atmosphere Substances 0.000 description 9
- 230000029936 alkylation Effects 0.000 description 8
- 238000005804 alkylation reaction Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical compound O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical class CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 7
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 7
- 150000004678 hydrides Chemical class 0.000 description 7
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Substances [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 7
- 230000007935 neutral effect Effects 0.000 description 7
- 125000001424 substituent group Chemical group 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 6
- 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 6
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 125000001931 aliphatic group Chemical group 0.000 description 6
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 238000007796 conventional method Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 238000001035 drying Methods 0.000 description 6
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 238000006268 reductive amination reaction Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000003638 chemical reducing agent Substances 0.000 description 5
- 150000001805 chlorine compounds Chemical class 0.000 description 5
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 239000012312 sodium hydride Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
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- AQEFLFZSWDEAIP-UHFFFAOYSA-N di-tert-butyl ether Chemical compound CC(C)(C)OC(C)(C)C AQEFLFZSWDEAIP-UHFFFAOYSA-N 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 125000006286 dichlorobenzyl group Chemical group 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- WBZKQQHYRPRKNJ-UHFFFAOYSA-L disulfite Chemical compound [O-]S(=O)S([O-])(=O)=O WBZKQQHYRPRKNJ-UHFFFAOYSA-L 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012156 elution solvent Substances 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- QTHZIALFBVAOTO-UHFFFAOYSA-N ethyl 2-(2-ethoxy-2-oxoethoxy)-3-(2-methoxyphenoxy)-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(OCC(=O)OCC)C(=O)OCC)OC1=CC=CC=C1OC QTHZIALFBVAOTO-UHFFFAOYSA-N 0.000 description 1
- HEVHOFPRKLMGMV-UHFFFAOYSA-N ethyl 2-[3-(2-methoxyphenoxy)-1-nitro-3-phenylprop-1-en-2-yl]oxyacetate Chemical compound C=1C=CC=CC=1C(C(=C[N+]([O-])=O)OCC(=O)OCC)OC1=CC=CC=C1OC HEVHOFPRKLMGMV-UHFFFAOYSA-N 0.000 description 1
- KLWKDMVWTIZBRK-UHFFFAOYSA-N ethyl 2-hydroxy-3-(2-nitrophenoxy)-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(O)C(=O)OCC)OC1=CC=CC=C1[N+]([O-])=O KLWKDMVWTIZBRK-UHFFFAOYSA-N 0.000 description 1
- BJBQBCHFEPXALG-UHFFFAOYSA-N ethyl 2-methoxy-3-(2-methoxyphenoxy)-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(OC)C(=O)OCC)OC1=CC=CC=C1OC BJBQBCHFEPXALG-UHFFFAOYSA-N 0.000 description 1
- KCDOGJLQPJHCPX-UHFFFAOYSA-N ethyl 2-methoxy-3-(2-nitrophenoxy)-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(OC)C(=O)OCC)OC1=CC=CC=C1[N+]([O-])=O KCDOGJLQPJHCPX-UHFFFAOYSA-N 0.000 description 1
- AIZBJJXPAKWJSL-UHFFFAOYSA-N ethyl 3-(2-aminophenoxy)-2-methoxy-3-phenylpropanoate;hydrochloride Chemical compound Cl.C=1C=CC=CC=1C(C(OC)C(=O)OCC)OC1=CC=CC=C1N AIZBJJXPAKWJSL-UHFFFAOYSA-N 0.000 description 1
- IKLSZPYSYSQTTB-UHFFFAOYSA-N ethyl 3-(2-hydroxyphenoxy)-2-methoxy-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C(C(OC)C(=O)OCC)OC1=CC=CC=C1O IKLSZPYSYSQTTB-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- OTGHWLKHGCENJV-UHFFFAOYSA-N glycidic acid Chemical compound OC(=O)C1CO1 OTGHWLKHGCENJV-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000006289 hydroxybenzyl group Chemical group 0.000 description 1
- 230000002631 hypothermal effect Effects 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- SXQFCVDSOLSHOQ-UHFFFAOYSA-N lactamide Chemical class CC(O)C(N)=O SXQFCVDSOLSHOQ-UHFFFAOYSA-N 0.000 description 1
- WOFDVDFSGLBFAC-UHFFFAOYSA-N lactonitrile Chemical class CC(O)C#N WOFDVDFSGLBFAC-UHFFFAOYSA-N 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910000103 lithium hydride Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- NRUBUZBAZRTHHX-UHFFFAOYSA-N lithium;propan-2-ylazanide Chemical compound [Li+].CC(C)[NH-] NRUBUZBAZRTHHX-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 1
- 239000000391 magnesium silicate Substances 0.000 description 1
- 229910052919 magnesium silicate Inorganic materials 0.000 description 1
- 235000019792 magnesium silicate Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 230000001333 moisturizer Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- MXAJVDHGJCYEKL-UHFFFAOYSA-N morpholine-3,5-dione Chemical class O=C1COCC(=O)N1 MXAJVDHGJCYEKL-UHFFFAOYSA-N 0.000 description 1
- CFZUIIKEGAIPQS-UHFFFAOYSA-N n-(2-chloroethyl)propan-1-amine Chemical class CCCNCCCl CFZUIIKEGAIPQS-UHFFFAOYSA-N 0.000 description 1
- GQKLTNAIFDFUDN-UHFFFAOYSA-N n-(2-hydroxyethyl)propanamide Chemical class CCC(=O)NCCO GQKLTNAIFDFUDN-UHFFFAOYSA-N 0.000 description 1
- WVSHIBLVYUVCBG-UHFFFAOYSA-N n-[3-(2-methoxyphenoxy)-3-phenylpropyl]hydroxylamine Chemical compound COC1=CC=CC=C1OC(CCNO)C1=CC=CC=C1 WVSHIBLVYUVCBG-UHFFFAOYSA-N 0.000 description 1
- UWMSSKGWQQTTRK-UHFFFAOYSA-N n-benzyl-2-chloro-n-[2-hydroxy-3-(2-methoxyphenoxy)-3-phenylpropyl]acetamide Chemical compound COC1=CC=CC=C1OC(C=1C=CC=CC=1)C(O)CN(C(=O)CCl)CC1=CC=CC=C1 UWMSSKGWQQTTRK-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229940068965 polysorbates Drugs 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 125000006308 propyl amino group Chemical class 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000009495 sugar coating Methods 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- 125000006493 trifluoromethyl benzyl group Chemical group 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/32—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups bound to acyclic carbon atoms and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/37—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to an acyclic carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
-
- 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
- C07C45/41—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenolysis or reduction of carboxylic groups or functional derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/58—Unsaturated compounds containing ether groups, groups, groups, or groups
- C07C59/64—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings
- C07C59/66—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings
- C07C59/68—Unsaturated compounds containing ether groups, groups, groups, or groups containing six-membered aromatic rings the non-carboxylic part of the ether containing six-membered aromatic rings the oxygen atom of the ether group being bound to a non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
- C07D265/33—Two oxygen atoms, in positions 3 and 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
- C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
- C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (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 That Contain Two Or More Ring Oxygen Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT1944978A IT1093255B (it) | 1978-01-20 | 1978-01-20 | Derivati fenossialcanolaminici |
IT1945078A IT1111676B (it) | 1978-01-20 | 1978-01-20 | Derivati della 2-fenossimetil-morfolina |
IT3053478A IT1160302B (it) | 1978-12-05 | 1978-12-05 | Derivati della 2-fenossimentil-morfolina |
IT30535/78A IT1101724B (it) | 1978-12-05 | 1978-12-05 | Derivati morfolinici e fenossiprofanolaminici e procedimento per la loro preparazione |
IT3053378A IT1160301B (it) | 1978-12-05 | 1978-12-05 | Derivati fenossialcanolaminici |
Publications (1)
Publication Number | Publication Date |
---|---|
BG61056B2 true BG61056B2 (bg) | 1996-09-30 |
Family
ID=27517788
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
BG098513A BG61056B2 (bg) | 1978-01-20 | 1994-02-22 | Заместени пропаноламинови и морфолинови производни |
Country Status (24)
Country | Link |
---|---|
US (2) | US4229449A (cs) |
JP (1) | JPS54148739A (cs) |
AT (1) | AT371813B (cs) |
AU (1) | AU525954B2 (cs) |
BG (1) | BG61056B2 (cs) |
CA (1) | CA1128942A (cs) |
CH (1) | CH650245A5 (cs) |
CS (1) | CS413391A3 (cs) |
CY (1) | CY1172A (cs) |
DE (2) | DE19875005I2 (cs) |
DK (1) | DK156565C (cs) |
FI (1) | FI71135C (cs) |
FR (2) | FR2442839A1 (cs) |
GB (1) | GB2014981B (cs) |
HK (1) | HK5783A (cs) |
IE (1) | IE47727B1 (cs) |
IL (1) | IL56369A (cs) |
KE (1) | KE3243A (cs) |
MY (1) | MY8400018A (cs) |
NO (1) | NO146953C (cs) |
NZ (1) | NZ189418A (cs) |
SE (1) | SE446727B (cs) |
SI (1) | SI7910096A8 (cs) |
YU (1) | YU42094B (cs) |
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GB1138405A (en) * | 1966-12-28 | 1969-01-01 | Ici Ltd | Morpholine derivatives |
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CA1085841A (en) * | 1976-05-19 | 1980-09-16 | Jean-Marie Ferland | Aryloxy proplamines, their preparation and use thereof |
-
1979
- 1979-01-04 IL IL56369A patent/IL56369A/xx unknown
- 1979-01-08 US US06/001,604 patent/US4229449A/en not_active Expired - Lifetime
- 1979-01-11 GB GB7901130A patent/GB2014981B/en not_active Expired
- 1979-01-11 CY CY1172A patent/CY1172A/xx unknown
- 1979-01-12 DE DE1998175005 patent/DE19875005I2/de active Active
- 1979-01-12 DE DE2901032A patent/DE2901032C2/de not_active Expired - Lifetime
- 1979-01-12 AU AU43327/79A patent/AU525954B2/en not_active Expired
- 1979-01-17 SI SI7910096A patent/SI7910096A8/sl unknown
- 1979-01-17 YU YU96/79A patent/YU42094B/xx unknown
- 1979-01-17 NZ NZ189418A patent/NZ189418A/xx unknown
- 1979-01-18 DK DK022679A patent/DK156565C/da not_active IP Right Cessation
- 1979-01-19 CH CH582/79A patent/CH650245A5/de not_active IP Right Cessation
- 1979-01-19 AT AT0040679A patent/AT371813B/de not_active IP Right Cessation
- 1979-01-19 NO NO790205A patent/NO146953C/no unknown
- 1979-01-19 SE SE7900498A patent/SE446727B/sv active Protection Beyond IP Right Term
- 1979-01-19 CA CA319,931A patent/CA1128942A/en not_active Expired
- 1979-01-19 FR FR7901413A patent/FR2442839A1/fr active Granted
- 1979-01-19 FI FI790177A patent/FI71135C/fi not_active IP Right Cessation
- 1979-01-20 JP JP449479A patent/JPS54148739A/ja active Granted
- 1979-01-30 IE IE107/79A patent/IE47727B1/en active Protection Beyond IP Right Term
- 1979-09-11 FR FR7922678A patent/FR2430412B1/fr not_active Expired
-
1980
- 1980-06-20 US US06/161,509 patent/US4271160A/en not_active Expired - Lifetime
-
1982
- 1982-10-25 KE KE3243A patent/KE3243A/xx unknown
-
1983
- 1983-02-08 HK HK57/83A patent/HK5783A/xx not_active IP Right Cessation
-
1984
- 1984-12-31 MY MY8418A patent/MY8400018A/xx unknown
-
1991
- 1991-12-30 CS CS914133A patent/CS413391A3/cs unknown
-
1994
- 1994-02-22 BG BG098513A patent/BG61056B2/bg unknown
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