JPS6228777B2 - - Google Patents
Info
- Publication number
- JPS6228777B2 JPS6228777B2 JP12630179A JP12630179A JPS6228777B2 JP S6228777 B2 JPS6228777 B2 JP S6228777B2 JP 12630179 A JP12630179 A JP 12630179A JP 12630179 A JP12630179 A JP 12630179A JP S6228777 B2 JPS6228777 B2 JP S6228777B2
- Authority
- JP
- Japan
- Prior art keywords
- acid
- sodium borohydride
- methoxyethyl
- phenoxy
- propanol
- 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
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 14
- 239000012279 sodium borohydride Substances 0.000 claims description 14
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 12
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- OFRYBPCSEMMZHR-UHFFFAOYSA-N alpha-Hydroxymetoprolol Chemical compound COCC(O)C1=CC=C(OCC(O)CNC(C)C)C=C1 OFRYBPCSEMMZHR-UHFFFAOYSA-N 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- 229960002237 metoprolol Drugs 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- -1 keto compound Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 125000003158 alcohol group Chemical group 0.000 description 2
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 2
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 229940030611 beta-adrenergic blocking agent Drugs 0.000 description 2
- 230000000903 blocking effect Effects 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UJUKHOATWVVDER-UHFFFAOYSA-N 1-amino-1-phenoxypropan-1-ol Chemical compound CCC(N)(O)OC1=CC=CC=C1 UJUKHOATWVVDER-UHFFFAOYSA-N 0.000 description 1
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- HYMIUVGTKKAYNU-UHFFFAOYSA-N 2-methoxy-1-[4-(oxiran-2-ylmethoxy)phenyl]ethanol Chemical compound C1=CC(C(O)COC)=CC=C1OCC1OC1 HYMIUVGTKKAYNU-UHFFFAOYSA-N 0.000 description 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical compound COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- XPNGNIFUDRPBFJ-UHFFFAOYSA-N alpha-methylbenzylalcohol Natural products CC1=CC=CC=C1CO XPNGNIFUDRPBFJ-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QILSFLSDHQAZET-UHFFFAOYSA-N diphenylmethanol Chemical class C=1C=CC=CC=1C(O)C1=CC=CC=C1 QILSFLSDHQAZET-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12630179A JPS5651438A (en) | 1979-09-29 | 1979-09-29 | Manufacture of 11isopropylaminoo33*44*22 methoxyethyl*phenoxy**22propanol or its salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12630179A JPS5651438A (en) | 1979-09-29 | 1979-09-29 | Manufacture of 11isopropylaminoo33*44*22 methoxyethyl*phenoxy**22propanol or its salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5651438A JPS5651438A (en) | 1981-05-09 |
| JPS6228777B2 true JPS6228777B2 (ko) | 1987-06-23 |
Family
ID=14931807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12630179A Granted JPS5651438A (en) | 1979-09-29 | 1979-09-29 | Manufacture of 11isopropylaminoo33*44*22 methoxyethyl*phenoxy**22propanol or its salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5651438A (ko) |
-
1979
- 1979-09-29 JP JP12630179A patent/JPS5651438A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5651438A (en) | 1981-05-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0004920B1 (de) | Carbazolyl-(4)-oxy-propanolamin-Derivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| US5110987A (en) | Method of preparing sphingosine derivatives | |
| EP0004532B1 (de) | 1-Aryloxy-3-nitratoalkylamino-2-propanole, Verfahren zu ihrer Herstellung und ihre pharmazeutischen Zubereitungen | |
| LU86435A1 (fr) | Nouveaux derives du morphinane et de la morphine,leur preparation,leur application comme medicaments et les compositions pharmaceutiques les contenant | |
| US4067904A (en) | Alkylsulfonylphenoxypropanolamine derivatives | |
| US4308399A (en) | O-(3-Amino-2-hydroxy-propyl)-amidoxime derivatives, process for the preparation thereof and pharmaceutical compositions containing same | |
| JPH062737B2 (ja) | フェノール誘導体及びその製造方法 | |
| EP1214313B1 (fr) | Heteroaryloxypropanolamines comme agonistes du recepteur beta3-adrenergique | |
| EP0348257A2 (fr) | Nouveaux dérivés d'(hétéro)aryl diazole, leur procédé de préparation et leur application en thérapeutique | |
| JPS6228777B2 (ko) | ||
| JPS6214538B2 (ko) | ||
| FR2467203A1 (fr) | Derives de 1,2,4-oxadiazolin-5-one, procede pour leur preparation et compositions pharmaceutiques les contenant | |
| CA2247675C (en) | Antifungal agents | |
| DD157796A5 (de) | Verfahren zur herstellung neuer derivate des 2-amino-aethanols | |
| JPH0353314B2 (ko) | ||
| JPS6320434B2 (ko) | ||
| CA2244662C (en) | Antifungal agents | |
| CA2264372C (fr) | Nouveaux composes du benzocyclobutane, leur procede de preparation et les compositions pharmaceutiques qui les contiennent | |
| JPS60146852A (ja) | プロパノ−ルアミン誘導体 | |
| EP1242381A2 (fr) | Derives de 2-phenyl-quinoleine et leur utilisation en tant qu'agent contractant des muscles lisses | |
| US4119729A (en) | Alkylsulfonylphenoxypropanolamine therapeutic process | |
| DK145079B (da) | Fremgangsmaade til fremstilling af 1-isopropylamino-3-(4-(2-methoxyethyl)-phenoxy)-2-propanol eller syreadditionssalte deraf | |
| WO1998003485A1 (fr) | PHENOXYPROPANOLAMINES A ACTION ANTAGONISTE β3-ADRENERGIQUE | |
| JP3225108B2 (ja) | 光学活性３−クロロ−２−プロパノール誘導体およびその製造法 | |
| KR820001447B1 (ko) | 3-인돌릴-3급 부틸아미노프로판올의 제조방법 |