FI59392C - Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter - Google Patents
Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter Download PDFInfo
- Publication number
- FI59392C FI59392C FI781001A FI781001A FI59392C FI 59392 C FI59392 C FI 59392C FI 781001 A FI781001 A FI 781001A FI 781001 A FI781001 A FI 781001A FI 59392 C FI59392 C FI 59392C
- Authority
- FI
- Finland
- Prior art keywords
- propanol
- phenoxy
- isopropylamino
- acid
- methoxythyl
- Prior art date
Links
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 title description 3
- 101100148710 Clarkia breweri SAMT gene Proteins 0.000 title 1
- 230000004913 activation Effects 0.000 title 1
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 title 1
- 230000001225 therapeutic effect Effects 0.000 title 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 23
- 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 14
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 11
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims description 11
- 229910000033 sodium borohydride Inorganic materials 0.000 claims description 10
- 239000012279 sodium borohydride Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 6
- 239000012442 inert solvent Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 229960002237 metoprolol Drugs 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 6
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- CYGMBGZUOIIVSF-UHFFFAOYSA-N 1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-2-methoxyethanone Chemical compound COCC(=O)C1=CC=C(OCC(O)CNC(C)C)C=C1 CYGMBGZUOIIVSF-UHFFFAOYSA-N 0.000 description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical group CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000008062 acetophenones Chemical class 0.000 description 2
- 239000002876 beta blocker Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000014121 butter Nutrition 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 150000008366 benzophenones Chemical class 0.000 description 1
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 1
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 1
- 229940097320 beta blocking agent Drugs 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000005194 ethylbenzenes Chemical class 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- -1 methylene compound Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical group CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011946 reduction process Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
- C07C49/84—Ketones containing a keto group bound to a six-membered aromatic ring containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI781001A FI59392C (fi) | 1978-04-01 | 1978-04-01 | Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter |
| NO790825A NO145402C (no) | 1978-04-01 | 1979-03-12 | Fremgangsmaate for fremstilling av et terapeutisk aktivt propanolamin, metoprolol |
| AT0196479A AT364349B (de) | 1978-04-01 | 1979-03-15 | Verfahren zur herestellung von 1-isopropylamino-3-(p-(2-methoxyaethyl) phenoxy) -propan-2ol und dessen saeureadditionssalzen |
| NL7902407A NL7902407A (nl) | 1978-04-01 | 1979-03-28 | Werkwijze voor de bereiding van een therapeutisch actief propanolamine; farmaceutisch preparaat dat het aldus bereide propanolamine bevat. |
| SE7902821A SE444677B (sv) | 1978-04-01 | 1979-03-29 | Forfarande for framstellning av 1-isopropylamino-3-/4-(2-metoxietyl)fenoxi/-2-propanol |
| CH301279A CH639065A5 (en) | 1978-04-01 | 1979-03-30 | Process for the preparation of 1-isopropylamino-3-[4-(2-methoxy- ethyl)phenoxy]-2-propanol |
| JP3923679A JPS54145623A (en) | 1978-04-01 | 1979-03-30 | Manufacture of 11isopropylaminoo33*44*22 methoxyethyl*phenoxy**22propanol or its salt |
| DK131079A DK145195C (da) | 1978-04-01 | 1979-03-30 | Fremgangsmaade til fremstilling af 1-isopropylamino-3-(4-(2-metoxyaethyl)-fenoxy)-2-propanol eller syreadditionssalte deraf |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI781001 | 1978-04-01 | ||
| FI781001A FI59392C (fi) | 1978-04-01 | 1978-04-01 | Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI781001A FI781001A (fi) | 1979-10-02 |
| FI59392B FI59392B (fi) | 1981-04-30 |
| FI59392C true FI59392C (fi) | 1982-02-02 |
Family
ID=8511594
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI781001A FI59392C (fi) | 1978-04-01 | 1978-04-01 | Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syraadditionssalter |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS54145623A (pt) |
| AT (1) | AT364349B (pt) |
| CH (1) | CH639065A5 (pt) |
| DK (1) | DK145195C (pt) |
| FI (1) | FI59392C (pt) |
| NL (1) | NL7902407A (pt) |
| NO (1) | NO145402C (pt) |
| SE (1) | SE444677B (pt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI59985C (fi) * | 1980-05-26 | 1982-01-08 | Farmos Oy | Foerfarande foer framstaellning av terapeutiskt aktiv 1-isopropylamino-3-(4-(2-metoxietyl)fenoxi)-2-propanol samt dess syra-additionssalter |
-
1978
- 1978-04-01 FI FI781001A patent/FI59392C/fi not_active IP Right Cessation
-
1979
- 1979-03-12 NO NO790825A patent/NO145402C/no unknown
- 1979-03-15 AT AT0196479A patent/AT364349B/de not_active IP Right Cessation
- 1979-03-28 NL NL7902407A patent/NL7902407A/xx not_active Application Discontinuation
- 1979-03-29 SE SE7902821A patent/SE444677B/sv not_active IP Right Cessation
- 1979-03-30 CH CH301279A patent/CH639065A5/de not_active IP Right Cessation
- 1979-03-30 JP JP3923679A patent/JPS54145623A/ja active Granted
- 1979-03-30 DK DK131079A patent/DK145195C/da not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NO790825L (no) | 1979-10-02 |
| AT364349B (de) | 1981-10-12 |
| CH639065A5 (en) | 1983-10-31 |
| ATA196479A (de) | 1981-03-15 |
| NO145402C (no) | 1982-03-17 |
| NL7902407A (nl) | 1979-10-03 |
| JPS6130653B2 (pt) | 1986-07-15 |
| SE444677B (sv) | 1986-04-28 |
| DK131079A (da) | 1979-10-02 |
| DK145195C (da) | 1983-04-05 |
| JPS54145623A (en) | 1979-11-14 |
| FI781001A (fi) | 1979-10-02 |
| NO145402B (no) | 1981-12-07 |
| DK145195B (da) | 1982-10-04 |
| SE7902821L (sv) | 1979-10-02 |
| FI59392B (fi) | 1981-04-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: FARMOS-YHTYMAE OY |