JPS58159449A - アセブトロ−ルの製造法 - Google Patents
アセブトロ−ルの製造法Info
- Publication number
- JPS58159449A JPS58159449A JP57221058A JP22105882A JPS58159449A JP S58159449 A JPS58159449 A JP S58159449A JP 57221058 A JP57221058 A JP 57221058A JP 22105882 A JP22105882 A JP 22105882A JP S58159449 A JPS58159449 A JP S58159449A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- butyramidophenoxy
- dioxalanyl
- isopropylamino
- formula
- 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.)
- Pending
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 claims description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 2
- 238000010306 acid treatment Methods 0.000 claims 1
- 239000012458 free base Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 10
- 229960002122 acebutolol Drugs 0.000 description 7
- GOEMGAFJFRBGGG-UHFFFAOYSA-N acebutolol Chemical compound CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 GOEMGAFJFRBGGG-UHFFFAOYSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RKJXMIZQSQZBKO-UHFFFAOYSA-N 2-oxidodioxathiolan-2-ium Chemical compound [O-][O+]1OCCS1 RKJXMIZQSQZBKO-UHFFFAOYSA-N 0.000 description 1
- CFPKVTKDDGALCR-UHFFFAOYSA-N 4-(phenoxymethyl)-1,3,2-dioxathiolane 2-oxide Chemical class O1S(=O)OCC1COC1=CC=CC=C1 CFPKVTKDDGALCR-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- GOXBZODPPBKULK-UHFFFAOYSA-N C(C)(=O)C1=C(OCC2OS(OC2)=O)C=CC(=C1)NC(CCC)=O Chemical compound C(C)(=O)C1=C(OCC2OS(OC2)=O)C=CC(=C1)NC(CCC)=O GOXBZODPPBKULK-UHFFFAOYSA-N 0.000 description 1
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229960003830 acebutolol hydrochloride Drugs 0.000 description 1
- KTUFKADDDORSSI-UHFFFAOYSA-N acebutolol hydrochloride Chemical compound Cl.CCCC(=O)NC1=CC=C(OCC(O)CNC(C)C)C(C(C)=O)=C1 KTUFKADDDORSSI-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CMHWPQYLNODERU-UHFFFAOYSA-N butanamide phenol Chemical compound C1(=CC=CC=C1)O.C(CCC)(=O)N CMHWPQYLNODERU-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FGWZEOPEZISTTR-UHFFFAOYSA-N n-(3-acetyl-4-hydroxyphenyl)butanamide Chemical group CCCC(=O)NC1=CC=C(O)C(C(C)=O)=C1 FGWZEOPEZISTTR-UHFFFAOYSA-N 0.000 description 1
- MFGKLROXINRXIU-UHFFFAOYSA-N n-[3-acetyl-4-(oxiran-2-ylmethoxy)phenyl]butanamide Chemical compound CC(=O)C1=CC(NC(=O)CCC)=CC=C1OCC1OC1 MFGKLROXINRXIU-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C07C213/06—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton from hydroxy amines by reactions involving the etherification or esterification of hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
- C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C217/28—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines
- C07C217/30—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having one amino group and at least two singly-bound oxygen atoms, with at least one being part of an etherified hydroxy group, bound to the carbon skeleton, e.g. ethers of polyhydroxy amines having the oxygen atom of at least one of the etherified hydroxy groups further bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/30—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms
- C07C233/33—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by doubly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Saccharide Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI814053 | 1981-12-17 | ||
| FI814053 | 1981-12-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS58159449A true JPS58159449A (ja) | 1983-09-21 |
Family
ID=8514961
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57221057A Pending JPS58159446A (ja) | 1981-12-17 | 1982-12-16 | メトプロロ−ルの製造法 |
| JP57221058A Pending JPS58159449A (ja) | 1981-12-17 | 1982-12-16 | アセブトロ−ルの製造法 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57221057A Pending JPS58159446A (ja) | 1981-12-17 | 1982-12-16 | メトプロロ−ルの製造法 |
Country Status (9)
| Country | Link |
|---|---|
| JP (2) | JPS58159446A (da) |
| KR (1) | KR840002768A (da) |
| CA (1) | CA1198125A (da) |
| DK (2) | DK541982A (da) |
| HU (1) | HU186649B (da) |
| NO (2) | NO824232L (da) |
| SE (2) | SE452612B (da) |
| SU (1) | SU1170968A3 (da) |
| YU (2) | YU275982A (da) |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56152461A (en) * | 1980-04-30 | 1981-11-26 | Ota Seiyaku Kk | Preparation of indole derivative |
-
1982
- 1982-12-06 KR KR1019820005450A patent/KR840002768A/ko unknown
- 1982-12-07 DK DK541982A patent/DK541982A/da not_active Application Discontinuation
- 1982-12-07 DK DK542082A patent/DK156567C/da not_active IP Right Cessation
- 1982-12-14 YU YU02759/82A patent/YU275982A/xx unknown
- 1982-12-14 YU YU02758/82A patent/YU275882A/xx unknown
- 1982-12-15 SU SU823523098A patent/SU1170968A3/ru active
- 1982-12-16 JP JP57221057A patent/JPS58159446A/ja active Pending
- 1982-12-16 SE SE8207199A patent/SE452612B/sv not_active IP Right Cessation
- 1982-12-16 HU HU824069A patent/HU186649B/hu not_active IP Right Cessation
- 1982-12-16 CA CA000417934A patent/CA1198125A/en not_active Expired
- 1982-12-16 JP JP57221058A patent/JPS58159449A/ja active Pending
- 1982-12-16 SE SE8207198A patent/SE8207198L/xx not_active Application Discontinuation
- 1982-12-16 NO NO824232A patent/NO824232L/no unknown
- 1982-12-16 NO NO824233A patent/NO155619C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SU1170968A3 (ru) | 1985-07-30 |
| HU186649B (en) | 1985-08-28 |
| YU275982A (en) | 1985-03-20 |
| NO824232L (no) | 1983-06-20 |
| DK156567C (da) | 1990-03-05 |
| NO155619B (no) | 1987-01-19 |
| YU275882A (en) | 1985-03-20 |
| CA1198125A (en) | 1985-12-17 |
| NO824233L (no) | 1983-06-20 |
| SE8207199D0 (sv) | 1982-12-16 |
| DK541982A (da) | 1983-06-18 |
| SE8207198L (sv) | 1983-06-18 |
| DK156567B (da) | 1989-09-11 |
| DK542082A (da) | 1983-06-18 |
| NO155619C (no) | 1987-04-29 |
| SE452612B (sv) | 1987-12-07 |
| SE8207199L (sv) | 1983-06-18 |
| JPS58159446A (ja) | 1983-09-21 |
| SE8207198D0 (sv) | 1982-12-16 |
| KR840002768A (ko) | 1984-07-16 |
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