KR850001916B1 - 아미노-페닐-에탄올 아민의 제조방법 - Google Patents
아미노-페닐-에탄올 아민의 제조방법 Download PDFInfo
- Publication number
- KR850001916B1 KR850001916B1 KR7501095A KR750001095A KR850001916B1 KR 850001916 B1 KR850001916 B1 KR 850001916B1 KR 7501095 A KR7501095 A KR 7501095A KR 750001095 A KR750001095 A KR 750001095A KR 850001916 B1 KR850001916 B1 KR 850001916B1
- Authority
- KR
- South Korea
- Prior art keywords
- ethanol
- phenyl
- amino
- tert
- chloro
- 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
- BFAQNLRAFSBFGU-UHFFFAOYSA-N 1-amino-1-phenylethanol Chemical compound CC(N)(O)C1=CC=CC=C1 BFAQNLRAFSBFGU-UHFFFAOYSA-N 0.000 title claims 2
- 238000000034 method Methods 0.000 title description 8
- 229950006768 phenylethanolamine Drugs 0.000 title 1
- -1 cyano, carboxy Chemical group 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 2
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000005429 oxyalkyl group Chemical group 0.000 claims 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 230000008018 melting Effects 0.000 description 76
- 238000002844 melting Methods 0.000 description 76
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
- 238000000354 decomposition reaction Methods 0.000 description 55
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
- 239000000243 solution Substances 0.000 description 35
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- 239000000203 mixture Substances 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 10
- 239000010410 layer Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 125000002252 acyl group Chemical group 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000013078 crystal Substances 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 5
- MMCDXJOMPMIKGP-UHFFFAOYSA-N Mabuterol hydrochloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 MMCDXJOMPMIKGP-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 4
- 238000005984 hydrogenation reaction Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 125000006239 protecting group Chemical group 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- NGCIPBQOTTZMOD-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(cyclobutylamino)ethanol;hydrochloride Chemical group Cl.C1=C(Br)C(N)=C(F)C=C1C(O)CNC1CCC1 NGCIPBQOTTZMOD-UHFFFAOYSA-N 0.000 description 3
- WNHISWIZEMKFRF-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-nitrophenyl)-2-(tert-butylamino)ethanol Chemical group CC(C)(C)NCC(O)C1=CC(Br)=C(N)C([N+]([O-])=O)=C1 WNHISWIZEMKFRF-UHFFFAOYSA-N 0.000 description 3
- QQBVYZBOKKTSBP-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-(cyclopropylamino)ethanol;hydrochloride Chemical compound Cl.C1=C(Cl)C(N)=C(F)C=C1C(O)CNC1CC1 QQBVYZBOKKTSBP-UHFFFAOYSA-N 0.000 description 3
- SBIZLZBFKBWZKL-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-nitrophenyl)-2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C([N+]([O-])=O)=C1 SBIZLZBFKBWZKL-UHFFFAOYSA-N 0.000 description 3
- MHWMCEILWDYPJN-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(cyclobutylamino)ethanol;hydrochloride Chemical compound Cl.C1=C(C(F)(F)F)C(N)=C(Cl)C=C1C(O)CNC1CCC1 MHWMCEILWDYPJN-UHFFFAOYSA-N 0.000 description 3
- CGCHJJMCSJZEGH-UHFFFAOYSA-N 2-amino-5-[2-(tert-butylamino)-1-hydroxyethyl]-3-chlorobenzonitrile Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C#N)=C1 CGCHJJMCSJZEGH-UHFFFAOYSA-N 0.000 description 3
- 208000009079 Bronchial Spasm Diseases 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003610 charcoal Substances 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 210000000697 sensory organ Anatomy 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- KMQUMSBPELGREK-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(propan-2-ylamino)ethanol;hydrochloride Chemical compound Cl.CC(C)NCC(O)C1=CC(F)=C(N)C(Br)=C1 KMQUMSBPELGREK-UHFFFAOYSA-N 0.000 description 2
- ZGTOOFRSOGZQHS-UHFFFAOYSA-N 1-(4-amino-3-bromo-5-fluorophenyl)-2-(tert-butylamino)ethanol;hydrochloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(F)=C(N)C(Br)=C1 ZGTOOFRSOGZQHS-UHFFFAOYSA-N 0.000 description 2
- WBJVJEHWTDQIPX-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-(2-methylbutan-2-ylamino)ethanol;hydrochloride Chemical compound Cl.CCC(C)(C)NCC(O)C1=CC(F)=C(N)C(Cl)=C1 WBJVJEHWTDQIPX-UHFFFAOYSA-N 0.000 description 2
- CZJFFCHZGPFPRG-UHFFFAOYSA-N 1-(4-amino-3-chloro-5-fluorophenyl)-2-(tert-butylamino)ethanol;hydrochloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(F)=C(N)C(Cl)=C1 CZJFFCHZGPFPRG-UHFFFAOYSA-N 0.000 description 2
- MPGBRVHTGIDELO-UHFFFAOYSA-N 1-(4-amino-3-fluorophenyl)-2-(dimethylamino)ethanol Chemical compound NC1=C(C=C(C=C1)C(CN(C)C)O)F MPGBRVHTGIDELO-UHFFFAOYSA-N 0.000 description 2
- IPBUQGQOWCKZHO-UHFFFAOYSA-N 1-(4-amino-3-fluorophenyl)-2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=C(N)C(F)=C1 IPBUQGQOWCKZHO-UHFFFAOYSA-N 0.000 description 2
- DXAXTIXMJXEGNY-UHFFFAOYSA-N 1-[4-amino-3-(diethylaminomethyl)phenyl]-2-(tert-butylamino)ethanol Chemical compound NC1=C(C=C(C=C1)C(CNC(C)(C)C)O)CN(CC)CC DXAXTIXMJXEGNY-UHFFFAOYSA-N 0.000 description 2
- DCXVJZIGAUPQPB-UHFFFAOYSA-N 1-[4-amino-3-(trifluoromethyl)phenyl]-2-(tert-butylamino)ethanol Chemical compound CC(C)(C)NCC(O)C1=CC=C(N)C(C(F)(F)F)=C1 DCXVJZIGAUPQPB-UHFFFAOYSA-N 0.000 description 2
- GIZXRBFANOUKFV-UHFFFAOYSA-N 1-[4-amino-3-bromo-5-(trifluoromethyl)phenyl]-2-(propan-2-ylamino)ethanol;hydrochloride Chemical compound Cl.CC(C)NCC(O)C1=CC(Br)=C(N)C(C(F)(F)F)=C1 GIZXRBFANOUKFV-UHFFFAOYSA-N 0.000 description 2
- ADMVUCDLKDANSY-UHFFFAOYSA-N 1-[4-amino-3-chloro-5-(trifluoromethyl)phenyl]-2-(propan-2-ylamino)ethanol Chemical compound CC(C)NCC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 ADMVUCDLKDANSY-UHFFFAOYSA-N 0.000 description 2
- ULCKFCKQYYCNTC-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-(cyclobutylamino)-1-hydroxyethyl]benzonitrile;hydrochloride Chemical group Cl.C1=C(C#N)C(N)=C(Br)C=C1C(O)CNC1CCC1 ULCKFCKQYYCNTC-UHFFFAOYSA-N 0.000 description 2
- CNRVBHZYPJXYDD-UHFFFAOYSA-N 2-amino-3-bromo-5-[2-(tert-butylamino)-1-hydroxyethyl]benzonitrile;hydrochloride Chemical group [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(Br)=C(N)C(C#N)=C1 CNRVBHZYPJXYDD-UHFFFAOYSA-N 0.000 description 2
- PDTDQNZOKGDEJX-UHFFFAOYSA-N 2-amino-3-chloro-5-[1-hydroxy-2-(2-methylbutan-2-ylamino)ethyl]benzonitrile;hydrochloride Chemical group Cl.CCC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C#N)=C1 PDTDQNZOKGDEJX-UHFFFAOYSA-N 0.000 description 2
- KUTWILNHIDUVRS-UHFFFAOYSA-N 2-amino-3-chloro-5-[1-hydroxy-2-(propylamino)ethyl]benzonitrile;hydrochloride Chemical group Cl.CCCNCC(O)C1=CC(Cl)=C(N)C(C#N)=C1 KUTWILNHIDUVRS-UHFFFAOYSA-N 0.000 description 2
- GCOOAOCXKMHBOF-UHFFFAOYSA-N 2-amino-3-chloro-5-[2-(cyclopentylamino)-1-hydroxyethyl]benzonitrile;hydrochloride Chemical group Cl.C1=C(C#N)C(N)=C(Cl)C=C1C(O)CNC1CCCC1 GCOOAOCXKMHBOF-UHFFFAOYSA-N 0.000 description 2
- TVNWRWIXFJERNS-UHFFFAOYSA-N 2-amino-3-fluoro-5-[1-hydroxy-2-(propan-2-ylamino)ethyl]benzonitrile;hydrochloride Chemical group Cl.CC(C)NCC(O)C1=CC(F)=C(N)C(C#N)=C1 TVNWRWIXFJERNS-UHFFFAOYSA-N 0.000 description 2
- NESCJTFKQSIWRR-UHFFFAOYSA-N 2-amino-5-[1-hydroxy-2-(2-methylbutan-2-ylamino)ethyl]benzonitrile Chemical compound CCC(C)(C)NCC(O)C1=CC=C(N)C(C#N)=C1 NESCJTFKQSIWRR-UHFFFAOYSA-N 0.000 description 2
- MKYVGPFLFZQOAM-UHFFFAOYSA-N 2-amino-5-[2-(cyclobutylamino)-1-hydroxyethyl]benzonitrile;hydrobromide Chemical compound Br.C1=C(C#N)C(N)=CC=C1C(O)CNC1CCC1 MKYVGPFLFZQOAM-UHFFFAOYSA-N 0.000 description 2
- FZCUPXLOELNEJK-UHFFFAOYSA-N 2-amino-5-[2-(tert-butylamino)-1-hydroxyethyl]-3-fluorobenzonitrile;hydrochloride Chemical compound [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(F)=C(N)C(C#N)=C1 FZCUPXLOELNEJK-UHFFFAOYSA-N 0.000 description 2
- OMDDZLHQQVNNRL-UHFFFAOYSA-N 2-amino-5-[2-(tert-butylamino)-1-hydroxyethyl]benzene-1,3-dicarbonitrile;hydrochloride Chemical group [Cl-].CC(C)(C)[NH2+]CC(O)C1=CC(C#N)=C(N)C(C#N)=C1 OMDDZLHQQVNNRL-UHFFFAOYSA-N 0.000 description 2
- NJKULRKQHJWHCU-UHFFFAOYSA-N 2-amino-5-[2-[1-(1,3-benzodioxol-5-yl)propan-2-ylamino]-1-hydroxyethyl]-3-chlorobenzonitrile hydrochloride Chemical group Cl.NC1=C(C=C(C=C1C#N)C(CNC(CC1=CC2=C(C=C1)OCO2)C)O)Cl NJKULRKQHJWHCU-UHFFFAOYSA-N 0.000 description 2
- YYVOMLJFTZMOJM-UHFFFAOYSA-N 2-amino-5-[2-[tert-butyl(hydroxy)amino]-1-hydroxyethyl]-3-chlorobenzonitrile;hydrochloride Chemical compound Cl.CC(C)(C)N(O)CC(O)C1=CC(Cl)=C(N)C(C#N)=C1 YYVOMLJFTZMOJM-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- WFNYILGNVYDXKK-UHFFFAOYSA-N CC(C)(C)NCC(C(C=C1)=CC(C(O)=O)=C1N)O Chemical compound CC(C)(C)NCC(C(C=C1)=CC(C(O)=O)=C1N)O WFNYILGNVYDXKK-UHFFFAOYSA-N 0.000 description 2
- 241000700198 Cavia Species 0.000 description 2
- ZRXPIPPQMVDETO-UHFFFAOYSA-N Cl.NC1=C(C=C(C=C1)C(CNC(C)(C)CC)O)C(F)(F)F Chemical compound Cl.NC1=C(C=C(C=C1)C(CNC(C)(C)CC)O)C(F)(F)F ZRXPIPPQMVDETO-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- LWJSGOMCMMDPEN-UHFFFAOYSA-N Mapenterol hydrochloride Chemical compound Cl.CCC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 LWJSGOMCMMDPEN-UHFFFAOYSA-N 0.000 description 2
- BXNFMIQRFCGFEC-UHFFFAOYSA-N N-[4-[2-(dimethylamino)-1-hydroxyethyl]-2-fluorophenyl]acetamide Chemical compound C(C)(=O)NC1=C(C=C(C=C1)C(CN(C)C)O)F BXNFMIQRFCGFEC-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 2
- 229960004373 acetylcholine Drugs 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000011097 chromatography purification Methods 0.000 description 2
- 239000003245 coal Substances 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000013213 extrapolation Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
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- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
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- NTBIYBAYFBNTCD-KBPBESRZSA-N dibenzoyl (2s,3s)-2,3-dihydroxybutanedioate Chemical compound O=C([C@@H](O)[C@H](O)C(=O)OC(=O)C=1C=CC=CC=1)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-KBPBESRZSA-N 0.000 description 1
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- JSJCTEKTBOKRST-UHFFFAOYSA-N mabuterol Chemical compound CC(C)(C)NCC(O)C1=CC(Cl)=C(N)C(C(F)(F)F)=C1 JSJCTEKTBOKRST-UHFFFAOYSA-N 0.000 description 1
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- MZENLOOAOURJEP-UHFFFAOYSA-N n-[2-fluoro-4-[1-hydroxy-2-(2-methylbutan-2-ylamino)ethyl]phenyl]acetamide Chemical compound CCC(C)(C)NCC(O)C1=CC=C(NC(C)=O)C(F)=C1 MZENLOOAOURJEP-UHFFFAOYSA-N 0.000 description 1
- MMALRVZZHYVGBL-UHFFFAOYSA-N n-[2-fluoro-4-[1-hydroxy-2-(propan-2-ylamino)ethyl]phenyl]acetamide Chemical compound CC(C)NCC(O)C1=CC=C(NC(C)=O)C(F)=C1 MMALRVZZHYVGBL-UHFFFAOYSA-N 0.000 description 1
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- RZEWIKVAGDKVHB-UHFFFAOYSA-N n-[4-[2-(tert-butylamino)-1-hydroxyethyl]-2-(trifluoromethyl)phenyl]acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=CC=C(C(O)CNC(C)(C)C)C=C1C(F)(F)F RZEWIKVAGDKVHB-UHFFFAOYSA-N 0.000 description 1
- KQYOITMXYOUDQD-UHFFFAOYSA-N n-[4-[2-(tert-butylamino)-1-hydroxyethyl]-2-chloro-6-nitrophenyl]acetamide;hydrochloride Chemical compound Cl.CC(=O)NC1=C(Cl)C=C(C(O)CNC(C)(C)C)C=C1[N+]([O-])=O KQYOITMXYOUDQD-UHFFFAOYSA-N 0.000 description 1
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- 229910052759 nickel Inorganic materials 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
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- OVYTZAASVAZITK-UHFFFAOYSA-M sodium;ethanol;hydroxide Chemical compound [OH-].[Na+].CCO OVYTZAASVAZITK-UHFFFAOYSA-M 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/02—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C215/22—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated
- C07C215/28—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings
- C07C215/30—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being unsaturated and containing six-membered aromatic rings containing hydroxy groups and carbon atoms of six-membered aromatic rings bound to the same carbon atom of the carbon skeleton
-
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pain & Pain Management (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 Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (13)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US2261914.3 | 1972-12-08 | ||
DE2261914.3 | 1972-12-18 | ||
DE2261914A DE2261914C3 (de) | 1972-12-18 | 1972-12-18 | Amino-phenyl-äthanolamine und deren Säureadditionssalze, Verfahren zu deren Herstellung und Arzneimittel |
DE2345442.4 | 1973-09-08 | ||
US2345442.4 | 1973-09-08 | ||
DE19732345442 DE2345442C2 (de) | 1973-09-08 | 1973-09-08 | d- und l-Phenyläthanolamine und deren Salze, Herstellungsverfahren und Arzneimittel auf deren Basis |
US2351281.4 | 1973-10-12 | ||
DE2351281.4 | 1973-10-12 | ||
DE19732351281 DE2351281C3 (de) | 1973-10-12 | 1973-10-12 | Aminophenyl-äthanolamin-Derivate, deren Herstellung und Verwendung |
DE2354961A DE2354961C2 (de) | 1973-11-02 | 1973-11-02 | Verfahren zur Herstellung von Aminophenyl-äthanolaminen |
US2354961.3 | 1973-11-02 | ||
DE2354961.3 | 1973-11-02 | ||
KR7302145A KR790000255B1 (en) | 1973-11-02 | 1973-12-14 | Process of manufacturing amino-penyl-ethanolamines |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR7302145A Division KR790000255B1 (en) | 1972-12-08 | 1973-12-14 | Process of manufacturing amino-penyl-ethanolamines |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830000207A KR830000207A (ko) | 1983-03-30 |
KR850001916B1 true KR850001916B1 (ko) | 1985-12-31 |
Family
ID=27431596
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR7501095A Expired KR850001916B1 (ko) | 1972-12-08 | 1975-05-19 | 아미노-페닐-에탄올 아민의 제조방법 |
Country Status (20)
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2430486A1 (fr) * | 1978-07-07 | 1980-02-01 | Oreal | Conditionnement d'un produit desinfectant et desodorisant pour cuvette de toilettes |
NL8105170A (nl) * | 1980-12-10 | 1982-07-01 | Thomae Gmbh Dr K | Nieuwe fenylalkylaminen, werkwijze ter bereiding daarvan en de toepassing daarvan als geneesmiddelen. |
FR2515177A1 (fr) * | 1981-10-28 | 1983-04-29 | Lafon Labor | Nouveaux derives de 1-(aminophenyl)-2-amino-1-ethanol, leur procede de preparation et leur utilisation en therapeutique |
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 |
EP0224001B1 (en) * | 1985-10-17 | 1991-03-20 | American Cyanamid Company | Anthranilonitrile derivatives and related compounds as useful agents for promoting growth, improving feed efficiency, and for increasing the lean meat to fat ratio of warm-blooded animals |
US4863959A (en) * | 1985-10-17 | 1989-09-05 | American Cyanamid Company | Anthranilonitrile derivatives as useful agents for promoting growth, improving feed efficiency, and for increasing the lean meat to fat ratio of warm-blooded animals |
GB8603475D0 (en) * | 1986-02-12 | 1986-03-19 | Glaxo Group Ltd | Chemical compounds |
GB8703007D0 (en) * | 1987-02-10 | 1987-03-18 | Glaxo Group Ltd | Chemical compounds |
EP0278727A3 (en) * | 1987-02-10 | 1990-03-14 | Glaxo Group Limited | 1-(4-amino-3-chloro-5-trifluoromethylphenyl)-2-(substituted amino)ethanol derivatives and their use in the treatment of respiratory disease |
SG119954A1 (en) * | 2003-08-29 | 2006-03-28 | Mitsui Chemicals Inc | Insecticide for agricultural or horticultural use and method of use thereof |
GB0604822D0 (en) * | 2006-03-09 | 2006-04-19 | Arakis Ltd | The treatment of inflammatory disorders and pain |
CN100497296C (zh) * | 2006-07-07 | 2009-06-10 | 沈阳药科大学 | 旋光活性的苯乙醇胺类化合物及其制法 |
GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
GB201903832D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
-
1973
- 1973-11-26 NL NLAANVRAGE7316139,A patent/NL176168C/xx not_active IP Right Cessation
- 1973-12-04 BG BG026781A patent/BG21209A3/xx unknown
- 1973-12-10 FI FI3770/73A patent/FI62052C/fi active
- 1973-12-14 DD DD175409A patent/DD111574A5/xx unknown
- 1973-12-14 RO RO7300077002A patent/RO63025A/ro unknown
- 1973-12-14 CH CH1755873A patent/CH605622A5/xx not_active IP Right Cessation
- 1973-12-14 CH CH1178977A patent/CH614188A5/xx not_active IP Right Cessation
- 1973-12-17 NO NO4814/73A patent/NO137782C/no unknown
- 1973-12-17 CA CA188,272A patent/CA1027955A/en not_active Expired
- 1973-12-17 IL IL43837A patent/IL43837A/en unknown
- 1973-12-17 SE SE7317035A patent/SE409700B/sv unknown
- 1973-12-17 PL PL73182408A patent/PL97194B1/pl unknown
- 1973-12-17 HU HUTO949A patent/HU168701B/hu unknown
- 1973-12-17 JP JP48141734A patent/JPS5811852B2/ja not_active Expired
- 1973-12-17 GB GB5834473A patent/GB1445740A/en not_active Expired
- 1973-12-17 DK DK684873A patent/DK150502C/da not_active IP Right Cessation
- 1973-12-18 FR FR7345290A patent/FR2210414B1/fr not_active Expired
- 1973-12-18 IE IE2292/73A patent/IE39065B1/xx unknown
-
1975
- 1975-05-19 KR KR7501095A patent/KR850001916B1/ko not_active Expired
-
1980
- 1980-02-28 HK HK66/80A patent/HK6680A/xx unknown
-
1988
- 1988-12-30 MY MY58344/73A patent/MY8800145A/xx unknown
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PA0107 | Divisional application |
Comment text: Divisional Application of Patent Patent event date: 19750519 Patent event code: PA01071R01D Filing date: 19731214 Application number text: 1019730002145 |
|
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19791204 Patent event code: PE09021S01D |
|
PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19800619 Patent event code: PE09021S01D |
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PE0601 | Decision on rejection of patent |
Patent event date: 19810328 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19800619 Comment text: Notification of reason for refusal Patent event code: PE06011S01I Patent event date: 19791204 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
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PE0902 | Notice of grounds for rejection |
Comment text: Notification of reason for refusal Patent event date: 19830110 Patent event code: PE09021S01D |
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PG1501 | Laying open of application | ||
PE0601 | Decision on rejection of patent |
Patent event date: 19830908 Comment text: Decision to Refuse Application Patent event code: PE06012S01D Patent event date: 19830110 Comment text: Notification of reason for refusal Patent event code: PE06011S01I Patent event date: 19800619 Comment text: Notification of reason for refusal Patent event code: PE06011S01I Patent event date: 19791204 Comment text: Notification of reason for refusal Patent event code: PE06011S01I |
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PG1605 | Publication of application before grant of patent |
Comment text: Decision on Publication of Application Patent event code: PG16051S01I Patent event date: 19851210 |
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E701 | Decision to grant or registration of patent right | ||
PE0701 | Decision of registration |
Patent event code: PE07011S01D Comment text: Decision to Grant Registration Patent event date: 19860314 |