FI56964C - 2-hydroxi-3-(4-(2-metoxietyl)fenoxi)-propylestrar som aer mellanprodukter vid framstaellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol - Google Patents
2-hydroxi-3-(4-(2-metoxietyl)fenoxi)-propylestrar som aer mellanprodukter vid framstaellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol Download PDFInfo
- Publication number
- FI56964C FI56964C FI761404A FI761404A FI56964C FI 56964 C FI56964 C FI 56964C FI 761404 A FI761404 A FI 761404A FI 761404 A FI761404 A FI 761404A FI 56964 C FI56964 C FI 56964C
- Authority
- FI
- Finland
- Prior art keywords
- methoxyethyl
- phenoxy
- hydroxy
- propanol
- amino
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title claims description 9
- -1 4- (2-METHOXYETHYL) PHENOXY Chemical class 0.000 title claims description 8
- 229960004592 isopropanol Drugs 0.000 title 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 5
- MELFVOGWPJFQBB-UHFFFAOYSA-N 3-[4-(2-methoxyethyl)phenoxy]propane-1,2-diol Chemical compound COCCC1=CC=C(OCC(O)CO)C=C1 MELFVOGWPJFQBB-UHFFFAOYSA-N 0.000 claims description 4
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000012043 crude product Substances 0.000 claims description 4
- 239000000284 extract Substances 0.000 claims description 4
- 239000000543 intermediate Substances 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 4
- 235000011152 sodium sulphate Nutrition 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- QNXIYXGRPXRGOB-UHFFFAOYSA-N oxolane;propan-2-one Chemical compound CC(C)=O.C1CCOC1 QNXIYXGRPXRGOB-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 235000002906 tartaric acid Nutrition 0.000 claims description 2
- 239000011975 tartaric acid Substances 0.000 claims description 2
- 229940095064 tartrate Drugs 0.000 claims description 2
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims 1
- 101150065749 Churc1 gene Proteins 0.000 claims 1
- 102100038239 Protein Churchill Human genes 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000002894 organic compounds Chemical class 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- XADVLVSLKPEHAS-UHFFFAOYSA-N 1-[1-(2-methoxyethyl)cyclohexa-2,4-dien-1-yl]oxy-3-(propan-2-ylamino)propan-2-ol Chemical compound COCCC1(OCC(CNC(C)C)O)CC=CC=C1 XADVLVSLKPEHAS-UHFFFAOYSA-N 0.000 description 1
- FAYGEALAEQKPDI-UHFFFAOYSA-N 4-(2-methoxyethyl)phenol Chemical compound COCCC1=CC=C(O)C=C1 FAYGEALAEQKPDI-UHFFFAOYSA-N 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000002876 beta blocker Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical group CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003513 tertiary aromatic amines Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/63—Esters of sulfonic acids
- C07C309/72—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/73—Esters of sulfonic acids having sulfur atoms of esterified sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
-
- 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
- C07C217/32—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 the six-membered aromatic ring or condensed ring system containing that ring being further substituted
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI761404A FI56964C (fi) | 1976-05-19 | 1976-05-19 | 2-hydroxi-3-(4-(2-metoxietyl)fenoxi)-propylestrar som aer mellanprodukter vid framstaellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol |
| PL1977195814A PL109679B1 (en) | 1976-05-19 | 1977-02-04 | Method of producing new 2-hydroxy-3-/4-/2-methoxyethylo/phenoxy/propyl esters |
| SE7705119A SE432927B (sv) | 1976-05-19 | 1977-05-03 | 2-hydroxy-3-/4-(2-metoxyetyl)-fenoxy/propylester som er mellanprodukt vid framstellning av 1-/4-(2-metoxyetyl)fenoxy/-3-/c1-metyletyl)-amino/-2-propanol |
| JP5856977A JPS52142033A (en) | 1976-05-19 | 1977-05-19 | Substituted phenoxy propanol derivatives and process for preparing same |
| SE8307159A SE8307159L (sv) | 1976-05-19 | 1983-12-23 | Forfarande for framstellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol |
| JP61031744A JPS6229424B1 (US06265458-20010724-C00056.png) | 1976-05-19 | 1986-02-14 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI761404A FI56964C (fi) | 1976-05-19 | 1976-05-19 | 2-hydroxi-3-(4-(2-metoxietyl)fenoxi)-propylestrar som aer mellanprodukter vid framstaellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol |
| FI761404 | 1976-05-19 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI761404A FI761404A (US06265458-20010724-C00056.png) | 1977-11-20 |
| FI56964B FI56964B (fi) | 1980-01-31 |
| FI56964C true FI56964C (fi) | 1980-05-12 |
Family
ID=8510004
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI761404A FI56964C (fi) | 1976-05-19 | 1976-05-19 | 2-hydroxi-3-(4-(2-metoxietyl)fenoxi)-propylestrar som aer mellanprodukter vid framstaellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol |
Country Status (4)
| Country | Link |
|---|---|
| JP (2) | JPS52142033A (US06265458-20010724-C00056.png) |
| FI (1) | FI56964C (US06265458-20010724-C00056.png) |
| PL (1) | PL109679B1 (US06265458-20010724-C00056.png) |
| SE (2) | SE432927B (US06265458-20010724-C00056.png) |
-
1976
- 1976-05-19 FI FI761404A patent/FI56964C/fi not_active IP Right Cessation
-
1977
- 1977-02-04 PL PL1977195814A patent/PL109679B1/pl unknown
- 1977-05-03 SE SE7705119A patent/SE432927B/xx not_active IP Right Cessation
- 1977-05-19 JP JP5856977A patent/JPS52142033A/ja active Granted
-
1983
- 1983-12-23 SE SE8307159A patent/SE8307159L/sv not_active Application Discontinuation
-
1986
- 1986-02-14 JP JP61031744A patent/JPS6229424B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6218547B2 (US06265458-20010724-C00056.png) | 1987-04-23 |
| SE8307159D0 (sv) | 1983-12-23 |
| SE432927B (sv) | 1984-04-30 |
| FI761404A (US06265458-20010724-C00056.png) | 1977-11-20 |
| JPS6229424B1 (US06265458-20010724-C00056.png) | 1987-06-25 |
| FI56964B (fi) | 1980-01-31 |
| JPS52142033A (en) | 1977-11-26 |
| SE8307159L (sv) | 1983-12-23 |
| PL109679B1 (en) | 1980-06-30 |
| PL195814A1 (pl) | 1978-02-13 |
| SE7705119L (sv) | 1977-11-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3928412A (en) | 1-Aryloxy-3-ureidoalkylamino-2-propanols | |
| FI103041B (fi) | Menetelmä lääkeaineina käyttökelpoisten N-alkyleenipiperidinoyhdisteid en ja niiden enantiomeerien valmistamiseksi | |
| NO151743B (no) | Analogifremgangsmaate til fremstilling av terapeutisk virksomme derivater av 3-amino-1,2-propandiol | |
| EP0373998B1 (fr) | Ethers d'oxime de propénone, procédé pour leur préparation et compositions pharmaceutiques les contenant | |
| US3974156A (en) | 2-(Substituted anilino) methylmorpholine compounds | |
| US4059622A (en) | Alkanolamine derivatives | |
| NO128653B (US06265458-20010724-C00056.png) | ||
| US4083992A (en) | Alkanolamine derivatives | |
| JPS6330894B2 (US06265458-20010724-C00056.png) | ||
| FI65987C (fi) | Foerfarande foer framstaellning av nya terapeutiskt anvaendbara alkanolaminderivat | |
| US4041075A (en) | Phenoxy-alkanolamine derivatives | |
| NO171784B (no) | Analogifremgangsmaate for fremstilling av nye antiarytmiske midler samt nye forbindelser for bruk ved fremstillingen | |
| JPH08268983A (ja) | 中間体として有用なアニリン誘導体 | |
| US2774770A (en) | Sulfur-containing amines | |
| FI56964C (fi) | 2-hydroxi-3-(4-(2-metoxietyl)fenoxi)-propylestrar som aer mellanprodukter vid framstaellning av 1-(4-(2-metoxietyl)-fenoxi)-3-((1-metyletyl)amino)-2-propanol | |
| US3574749A (en) | 1-(4-amidophenoxy)-3-amino-2-propanol derivatives | |
| JPS6326099B2 (US06265458-20010724-C00056.png) | ||
| SU598557A3 (ru) | Способ получени производных 1-фенокси-3-аминопропан-2-ола или их солей | |
| FI62060B (fi) | Foerfarande foer framstaellning av beta-blockerande substituerad 2-hydroxi-3-(2-acyl-4-ureido-fenoxi)-propylaminderivat | |
| EP0122827A1 (fr) | (Carbéthoxy-2 benzalkylamido-4 phénoxy)-1 amino-3 propanols-2, leurs préparations et leurs utilisations en thérapeutique | |
| US5047425A (en) | Amine derivatives having cardiovascular activity | |
| CA1146575A (en) | Process for the manufacture of novel derivatives of 2- aminoethanol | |
| FI66856B (fi) | Foerfarande foer framstaellning av nya hjaertstimulerande alkanolaminderivat | |
| PL82037B1 (US06265458-20010724-C00056.png) | ||
| US3959486A (en) | Method for producing β-adrenergic blockage with alkanolamine derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: HUHTAMAEKI OY |