FI61474C - Foerfarande foer framstaellning av syraadditionssalter av 3,4-diacyloxi-alfa-((metylamino)-metyl)-bensylalkohol - Google Patents
Foerfarande foer framstaellning av syraadditionssalter av 3,4-diacyloxi-alfa-((metylamino)-metyl)-bensylalkohol Download PDFInfo
- Publication number
- FI61474C FI61474C FI810700A FI810700A FI61474C FI 61474 C FI61474 C FI 61474C FI 810700 A FI810700 A FI 810700A FI 810700 A FI810700 A FI 810700A FI 61474 C FI61474 C FI 61474C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- methylamino
- methyl
- acid addition
- addition salt
- Prior art date
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title description 5
- -1 (METHYLAMINO) -METHYL Chemical class 0.000 title description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 19
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229960000583 acetic acid Drugs 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims description 5
- 239000000243 solution Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000002955 isolation Methods 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Substances OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims 2
- 239000003637 basic solution Substances 0.000 claims 1
- 238000000605 extraction Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UCTWMZQNUQWSLP-UHFFFAOYSA-N adrenaline Chemical compound CNCC(O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-UHFFFAOYSA-N 0.000 description 4
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 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 3
- 239000003054 catalyst Substances 0.000 description 3
- 230000001603 reducing effect Effects 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000003943 catecholamines Chemical class 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- 239000011877 solvent mixture 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
- 208000010412 Glaucoma Diseases 0.000 description 1
- CSRRBDMYOUQTCO-UHFFFAOYSA-N [2-(3,4-dihydroxyphenyl)-2-oxoethyl]-methylazanium;chloride Chemical compound Cl.CNCC(=O)C1=CC=C(O)C(O)=C1 CSRRBDMYOUQTCO-UHFFFAOYSA-N 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 150000003855 acyl compounds Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229960002892 adrenalone Drugs 0.000 description 1
- PZMVOUYYNKPMSI-UHFFFAOYSA-N adrenalone Chemical compound CNCC(=O)C1=CC=C(O)C(O)=C1 PZMVOUYYNKPMSI-UHFFFAOYSA-N 0.000 description 1
- 229960005151 adrenalone hydrochloride Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001975 sympathomimetic effect Effects 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI810700A FI61474C (fi) | 1981-03-06 | 1981-03-06 | Foerfarande foer framstaellning av syraadditionssalter av 3,4-diacyloxi-alfa-((metylamino)-metyl)-bensylalkohol |
| AT0009182A AT380684B (de) | 1981-03-06 | 1982-01-13 | Verfahren zum herstellen und isolieren eines saeureadditionssalzes von di-o-acyl-adrenalinen |
| DK24082A DK149121C (da) | 1981-03-06 | 1982-01-20 | Fremgangsmaade til fremstilling af syreadditionssalte af 3,4-diacyloxy-alfa-((methylamino)-methyl)-benzylalkohol |
| ES509170A ES8301891A1 (es) | 1981-03-06 | 1982-01-29 | "metodo para la preparacion y aislamiento de 3,4-diaciloxi-alfa-(metilamino)-metil-bencilalcohol". |
| CA000395336A CA1178605A (en) | 1981-03-06 | 1982-02-01 | PROCESS FOR PREPARING ACID ADDITION SALTS OF 3,4- DIACYLOXY-.alpha.-[(METHYLAMINO)-METHYL]- BENZYLALCOHOL |
| CS127882A CS229927B2 (en) | 1981-03-06 | 1982-02-24 | Production method of 3,4-diacyloxy-alfa ( ( methylamino(-methyl) )benzylalcohol |
| DD23779582A DD202424A5 (de) | 1981-03-06 | 1982-03-01 | Verfahren zur herstellung von saeurezusatzsalzen von 3,4-diazyloxy-gamma-((methylamin)-methyl)-benzylalkohol |
| IT8219944A IT8219944A0 (it) | 1981-03-06 | 1982-03-03 | Procedimento per preparare sali di addizione di acidi di 3,4-diacilossi-alfa-parentesi aperta (metilammino)-metilparentesi quadra chiusa -benzilalcool. |
| RO106810A RO84817B (ro) | 1981-03-06 | 1982-03-04 | Procedeu de preparare a sarurilor acide de aditie ale 3, 4-diaciloximetilamino-metilbenzilalcoolilor |
| PL23531382A PL235313A1 (cs) | 1981-03-06 | 1982-03-04 | |
| NO820691A NO151704C (no) | 1981-03-06 | 1982-03-05 | Fremgangsmaate ved fremstilling av syreaddisjonssalter av 3,4-diacyloxy-alfa-((methylamino)-methyl)-benzylalkohol |
| SU823402587A SU1122219A3 (ru) | 1981-03-06 | 1982-03-05 | Способ получени хлоргидрата 3,4-дипивалоил- @ - @ (метиламино)-метил @ -бензилового спирта |
| PT7454082A PT74540B (en) | 1981-03-06 | 1982-03-05 | Process for preparing acid addition salts of 3,4-diacyloxi-alp ha-<(methylamino)-methyl>-benzylalcohol |
| HU68282A HU186483B (en) | 1981-03-06 | 1982-03-05 | Process for preparing acid addition salts of derivatives of 3,4-di/acyloxy/-alfa-/methylamino-methyl/-benyl-alcohol |
| GR67430A GR76375B (cs) | 1981-03-06 | 1982-09-26 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI810700 | 1981-03-06 | ||
| FI810700A FI61474C (fi) | 1981-03-06 | 1981-03-06 | Foerfarande foer framstaellning av syraadditionssalter av 3,4-diacyloxi-alfa-((metylamino)-metyl)-bensylalkohol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI61474B FI61474B (fi) | 1982-04-30 |
| FI61474C true FI61474C (fi) | 1982-08-10 |
Family
ID=8514202
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI810700A FI61474C (fi) | 1981-03-06 | 1981-03-06 | Foerfarande foer framstaellning av syraadditionssalter av 3,4-diacyloxi-alfa-((metylamino)-metyl)-bensylalkohol |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT380684B (cs) |
| CA (1) | CA1178605A (cs) |
| CS (1) | CS229927B2 (cs) |
| DD (1) | DD202424A5 (cs) |
| DK (1) | DK149121C (cs) |
| ES (1) | ES8301891A1 (cs) |
| FI (1) | FI61474C (cs) |
| GR (1) | GR76375B (cs) |
| HU (1) | HU186483B (cs) |
| IT (1) | IT8219944A0 (cs) |
| NO (1) | NO151704C (cs) |
| PL (1) | PL235313A1 (cs) |
| PT (1) | PT74540B (cs) |
| RO (1) | RO84817B (cs) |
| SU (1) | SU1122219A3 (cs) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1298771A (en) * | 1969-04-01 | 1972-12-06 | Sterling Drug Inc | Carboxylic esters of hydroxyphenylalkanolamines |
| US3809714A (en) * | 1972-08-31 | 1974-05-07 | Interx Research Corp | Novel ester of ((methylamino)methyl) benzyl alcohol |
| DE2341876A1 (de) * | 1973-08-18 | 1975-03-13 | Boehringer Sohn Ingelheim | Neue 1-(m-acyloxyphenyl)-1-hydroxy- 2-n-alkylamino-aethane, deren saeureadditionssalze, diese enthaltende arzneimittel, sowie verfahren zu ihrer herstellung |
| US4035405A (en) * | 1976-07-09 | 1977-07-12 | Interx Research Corporation | Novel synthesis for preparing the hydrochloride salt of selected catecholamine derivatives |
-
1981
- 1981-03-06 FI FI810700A patent/FI61474C/fi not_active IP Right Cessation
-
1982
- 1982-01-13 AT AT0009182A patent/AT380684B/de not_active IP Right Cessation
- 1982-01-20 DK DK24082A patent/DK149121C/da not_active IP Right Cessation
- 1982-01-29 ES ES509170A patent/ES8301891A1/es not_active Expired
- 1982-02-01 CA CA000395336A patent/CA1178605A/en not_active Expired
- 1982-02-24 CS CS127882A patent/CS229927B2/cs unknown
- 1982-03-01 DD DD23779582A patent/DD202424A5/de not_active IP Right Cessation
- 1982-03-03 IT IT8219944A patent/IT8219944A0/it unknown
- 1982-03-04 PL PL23531382A patent/PL235313A1/xx unknown
- 1982-03-04 RO RO106810A patent/RO84817B/ro unknown
- 1982-03-05 NO NO820691A patent/NO151704C/no unknown
- 1982-03-05 HU HU68282A patent/HU186483B/hu not_active IP Right Cessation
- 1982-03-05 SU SU823402587A patent/SU1122219A3/ru active
- 1982-03-05 PT PT7454082A patent/PT74540B/pt unknown
- 1982-09-26 GR GR67430A patent/GR76375B/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CS229927B2 (en) | 1984-07-16 |
| CA1178605A (en) | 1984-11-27 |
| PL235313A1 (cs) | 1982-09-27 |
| ES509170A0 (es) | 1982-12-16 |
| IT8219944A0 (it) | 1982-03-03 |
| SU1122219A3 (ru) | 1984-10-30 |
| DD202424A5 (de) | 1983-09-14 |
| ATA9182A (de) | 1985-11-15 |
| PT74540A (en) | 1982-04-01 |
| DK24082A (da) | 1982-09-07 |
| NO151704C (no) | 1985-05-22 |
| NO151704B (no) | 1985-02-11 |
| RO84817A (ro) | 1984-09-29 |
| DK149121B (da) | 1986-02-03 |
| NO820691L (no) | 1982-09-07 |
| FI61474B (fi) | 1982-04-30 |
| AT380684B (de) | 1986-06-25 |
| PT74540B (en) | 1986-01-27 |
| GR76375B (cs) | 1984-08-06 |
| RO84817B (ro) | 1984-10-30 |
| ES8301891A1 (es) | 1982-12-16 |
| DK149121C (da) | 1986-07-07 |
| HU186483B (en) | 1985-08-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed | ||
| MM | Patent lapsed |
Owner name: OY STAR AB |