FI63016C - Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin - Google Patents
Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin Download PDFInfo
- Publication number
- FI63016C FI63016C FI803119A FI803119A FI63016C FI 63016 C FI63016 C FI 63016C FI 803119 A FI803119 A FI 803119A FI 803119 A FI803119 A FI 803119A FI 63016 C FI63016 C FI 63016C
- Authority
- FI
- Finland
- Prior art keywords
- phenoxy
- methoxyethyl
- isopropylamino
- propanol
- acetoxy
- Prior art date
Links
- 230000001225 therapeutic effect Effects 0.000 title claims 2
- IUBSYMUCCVWXPE-UHFFFAOYSA-N metoprolol Chemical compound COCCC1=CC=C(OCC(O)CNC(C)C)C=C1 IUBSYMUCCVWXPE-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims abstract description 10
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims abstract description 7
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims abstract description 7
- CTZFISYPUSQFRR-UHFFFAOYSA-N [1-[4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl]-2-methoxyethyl] acetate Chemical compound COCC(OC(C)=O)C1=CC=C(OCC(O)CNC(C)C)C=C1 CTZFISYPUSQFRR-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- TXXKLRMEPRZIPQ-UHFFFAOYSA-N [2-methoxy-1-[4-(oxiran-2-ylmethoxy)phenyl]ethyl] acetate Chemical compound C1=CC(C(OC(C)=O)COC)=CC=C1OCC1OC1 TXXKLRMEPRZIPQ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000033 sodium borohydride Inorganic materials 0.000 claims abstract description 5
- 239000012279 sodium borohydride Substances 0.000 claims abstract description 5
- 229940098779 methanesulfonic acid Drugs 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 238000007796 conventional method Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 10
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 239000012442 inert solvent Substances 0.000 abstract description 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000000047 product Substances 0.000 description 12
- 229960002237 metoprolol Drugs 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 5
- -1 isopropylamino side chain Chemical group 0.000 description 5
- 238000006722 reduction reaction Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 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 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 102000012740 beta Adrenergic Receptors Human genes 0.000 description 3
- 108010079452 beta Adrenergic Receptors Proteins 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229940095064 tartrate Drugs 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 229960001300 metoprolol tartrate Drugs 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 150000003892 tartrate salts Chemical class 0.000 description 2
- WUBVEMGCQRSBBT-UHFFFAOYSA-N tert-butyl 4-(trifluoromethylsulfonyloxy)-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(=O)(=O)C(F)(F)F)=CC1 WUBVEMGCQRSBBT-UHFFFAOYSA-N 0.000 description 2
- QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 1
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 1
- ILSYTMBVJDPAKS-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;propan-2-one Chemical compound CC(C)=O.OC(=O)C(O)C(O)C(O)=O ILSYTMBVJDPAKS-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- AGKWDBAZOVFZCO-UHFFFAOYSA-N [1-(4-hydroxyphenyl)-2-methoxyethyl] acetate Chemical compound COCC(OC(C)=O)C1=CC=C(O)C=C1 AGKWDBAZOVFZCO-UHFFFAOYSA-N 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000007860 aryl ester derivatives Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012230 colorless oil Substances 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
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 238000006053 organic reaction Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000003087 receptor blocking agent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000002792 vascular Effects 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
- 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
- C07C213/08—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 not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI803119A FI63016C (fi) | 1980-06-04 | 1980-10-01 | Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin |
| EP81200616A EP0041760B1 (en) | 1980-06-04 | 1981-06-03 | Process for the preparation of 1-isopropylamino-3-(4-(2-methoxy-ethyl)-phenoxy)-2-propanol |
| AT81200616T ATE6501T1 (de) | 1980-06-04 | 1981-06-03 | Verfahren zur herstellung von 1-isopropylamino-3(4-(2-methoxy[thyl)-phenoxy)-2-propanol. |
| DK243481A DK153144C (da) | 1980-06-04 | 1981-06-03 | Fremgangsmaade til fremstilling af 1-isopropylamino-3-(4-(2-methoxyethyl)-phenoxy)-2-propanol eller syreadditionssalte deraf |
| JP2136936A JPH0314547A (ja) | 1980-06-04 | 1990-05-25 | １―イソプロピルアミノ―３―［４―（１―アセトキシ―２―メトキシエチル）―フエノキシ〕―２―プロパノールおよびその製造法 |
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI801792 | 1980-06-04 | ||
| FI801792A FI801792A7 (fi) | 1980-06-04 | 1980-06-04 | Menetelmä terapeuttisesti aktiivisen propanoliamiinin valmistamiseksi. |
| FI803119A FI63016C (fi) | 1980-06-04 | 1980-10-01 | Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin |
| FI803119 | 1980-10-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI803119L FI803119L (fi) | 1981-12-05 |
| FI63016B FI63016B (fi) | 1982-12-31 |
| FI63016C true FI63016C (fi) | 1983-04-11 |
Family
ID=26157125
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI803119A FI63016C (fi) | 1980-06-04 | 1980-10-01 | Foerfarande foer framstaellning av en terapeutiskt aktiv propanolamin |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP0041760B1 (en, 2012) |
| JP (1) | JPH0314547A (en, 2012) |
| AT (1) | ATE6501T1 (en, 2012) |
| DK (1) | DK153144C (en, 2012) |
| FI (1) | FI63016C (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0095827B1 (en) * | 1982-04-08 | 1985-07-24 | Beecham Group Plc | N-substituted derivatives of ethanol amine |
| US11957663B1 (en) | 2023-10-31 | 2024-04-16 | King Faisal University | 3-(2,4,5-tris(4-chlorophenyl)-1H-imidazol-1-yl) propanoic acid as an antimicrobial compound |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE354851B (en, 2012) * | 1970-02-18 | 1973-03-26 | Haessle Ab |
-
1980
- 1980-10-01 FI FI803119A patent/FI63016C/fi not_active IP Right Cessation
-
1981
- 1981-06-03 AT AT81200616T patent/ATE6501T1/de not_active IP Right Cessation
- 1981-06-03 DK DK243481A patent/DK153144C/da not_active IP Right Cessation
- 1981-06-03 EP EP81200616A patent/EP0041760B1/en not_active Expired
-
1990
- 1990-05-25 JP JP2136936A patent/JPH0314547A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0333699B2 (en, 2012) | 1991-05-20 |
| EP0041760B1 (en) | 1984-03-07 |
| FI803119L (fi) | 1981-12-05 |
| JPH0314547A (ja) | 1991-01-23 |
| DK153144C (da) | 1988-10-31 |
| FI63016B (fi) | 1982-12-31 |
| ATE6501T1 (de) | 1984-03-15 |
| DK243481A (da) | 1981-12-05 |
| EP0041760A1 (en) | 1981-12-16 |
| DK153144B (da) | 1988-06-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: AB HAESSLE |