JPH0255418B2 - - Google Patents
Info
- Publication number
- JPH0255418B2 JPH0255418B2 JP9201081A JP9201081A JPH0255418B2 JP H0255418 B2 JPH0255418 B2 JP H0255418B2 JP 9201081 A JP9201081 A JP 9201081A JP 9201081 A JP9201081 A JP 9201081A JP H0255418 B2 JPH0255418 B2 JP H0255418B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- methylethyl
- ethylamino
- methanol
- methoxyphenoxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 150000001875 compounds Chemical class 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- -1 methylsulfinyl compound Chemical class 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000000921 elemental analysis Methods 0.000 description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 102000004305 alpha Adrenergic Receptors Human genes 0.000 description 3
- 108090000861 alpha Adrenergic Receptors Proteins 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- LAAVBXWIEVCLGO-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfanylphenyl)-n-[2-(2-methoxyphenoxy)ethyl]propan-2-amine Chemical compound COC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(SC)=C1 LAAVBXWIEVCLGO-UHFFFAOYSA-N 0.000 description 2
- CMSDSFTUZAJMNS-UHFFFAOYSA-N 1-(4-methoxy-3-sulfanylphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1S CMSDSFTUZAJMNS-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- OVKDOXKZHSZVOQ-UHFFFAOYSA-N 1-(3-methoxy-4-methylphenyl)propan-2-one Chemical compound COC1=CC(CC(C)=O)=CC=C1C OVKDOXKZHSZVOQ-UHFFFAOYSA-N 0.000 description 1
- LBUHGVUVERQFFW-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfanylphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1SC LBUHGVUVERQFFW-UHFFFAOYSA-N 0.000 description 1
- AMZVJACDWALPSN-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfinylphenyl)-n-[2-(2-methoxyphenoxy)ethyl]propan-2-amine Chemical compound COC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(C)=O)=C1 AMZVJACDWALPSN-UHFFFAOYSA-N 0.000 description 1
- YMKOCAZJUJXMBR-UHFFFAOYSA-N 1-(4-methoxy-3-methylsulfonylphenyl)-n-[2-(2-methoxyphenoxy)ethyl]propan-2-amine Chemical compound COC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(S(C)(=O)=O)=C1 YMKOCAZJUJXMBR-UHFFFAOYSA-N 0.000 description 1
- YCUXDIFPTHNTSR-UHFFFAOYSA-N 1-methoxy-2-methylsulfanylbenzene Chemical compound COC1=CC=CC=C1SC YCUXDIFPTHNTSR-UHFFFAOYSA-N 0.000 description 1
- CKJRKLKVCHMWLV-UHFFFAOYSA-N 2-(2-methoxyphenoxy)ethanamine Chemical compound COC1=CC=CC=C1OCCN CKJRKLKVCHMWLV-UHFFFAOYSA-N 0.000 description 1
- PKSHOAJHMZSFCW-UHFFFAOYSA-N 3-(3-methoxyphenyl)butan-2-one Chemical compound COC1=CC=CC(C(C)C(C)=O)=C1 PKSHOAJHMZSFCW-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- FKXAPHPAKWOJBG-UHFFFAOYSA-N n-[2-(2-ethoxyphenoxy)ethyl]-1-(4-methoxy-3-methylsulfanylphenyl)propan-2-amine;hydrochloride Chemical compound Cl.CCOC1=CC=CC=C1OCCNC(C)CC1=CC=C(OC)C(SC)=C1 FKXAPHPAKWOJBG-UHFFFAOYSA-N 0.000 description 1
- GEVPUGOOGXGPIO-UHFFFAOYSA-N oxalic acid;dihydrate Chemical compound O.O.OC(=O)C(O)=O GEVPUGOOGXGPIO-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- DLRJIFUOBPOJNS-UHFFFAOYSA-N phenetole Chemical compound CCOC1=CC=CC=C1 DLRJIFUOBPOJNS-UHFFFAOYSA-N 0.000 description 1
- SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
- 229960001802 phenylephrine Drugs 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000002315 pressor effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9201081A JPS57206652A (en) | 1981-06-15 | 1981-06-15 | Substituted phenyl ether derivative |
| DE19813128117 DE3128117A1 (de) | 1980-07-29 | 1981-07-16 | Neue phenyl-aethylaminderivate, verfahren zu ihrer herstellung |
| GB8122797A GB2083022B (en) | 1980-07-29 | 1981-07-23 | Phenethylamine derivatives and their production |
| CA000382575A CA1224494A (en) | 1980-07-29 | 1981-07-27 | Process of producing novel phenethylamine derivatives |
| IT68052/81A IT1172230B (it) | 1980-07-29 | 1981-07-28 | Derivati della fenetilammina e procentimento per la loro produzione |
| ES504376A ES8301882A1 (es) | 1980-07-29 | 1981-07-28 | Un procedimiento para la preparacion de un derivado de fene-tilamina |
| FR8114716A FR2487827A1 (fr) | 1980-07-29 | 1981-07-29 | Nouveaux derives de la phenetylamine et procede pour leur production |
| ES514426A ES514426A0 (es) | 1981-06-15 | 1982-07-27 | Un procedimiento para la preparacion de un derivado de fenetilamina. |
| US07/307,200 US4880841A (en) | 1980-07-29 | 1989-02-03 | Process of producing phenethylamine derivatives |
| US07/569,780 US5063246A (en) | 1980-07-29 | 1990-08-21 | Phenethylamine derivative compositions and use |
| US07/737,976 US5198587A (en) | 1980-07-29 | 1991-07-30 | Phenethylamine derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9201081A JPS57206652A (en) | 1981-06-15 | 1981-06-15 | Substituted phenyl ether derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57206652A JPS57206652A (en) | 1982-12-18 |
| JPH0255418B2 true JPH0255418B2 (ru) | 1990-11-27 |
Family
ID=14042505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9201081A Granted JPS57206652A (en) | 1980-07-29 | 1981-06-15 | Substituted phenyl ether derivative |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS57206652A (ru) |
| ES (1) | ES514426A0 (ru) |
-
1981
- 1981-06-15 JP JP9201081A patent/JPS57206652A/ja active Granted
-
1982
- 1982-07-27 ES ES514426A patent/ES514426A0/es active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| ES8306084A1 (es) | 1983-05-01 |
| JPS57206652A (en) | 1982-12-18 |
| ES514426A0 (es) | 1983-05-01 |
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