CH495973A - Verfahren zur Gewinnung von reinem Acetyldigoxin in der a-Form - Google Patents
Verfahren zur Gewinnung von reinem Acetyldigoxin in der a-FormInfo
- Publication number
- CH495973A CH495973A CH122968A CH122968A CH495973A CH 495973 A CH495973 A CH 495973A CH 122968 A CH122968 A CH 122968A CH 122968 A CH122968 A CH 122968A CH 495973 A CH495973 A CH 495973A
- Authority
- CH
- Switzerland
- Prior art keywords
- acetyldigoxin
- mixture
- acetyldigitoxin
- acetylgitoxin
- separation
- Prior art date
Links
- HWKJSYYYURVNQU-DXJNJSHLSA-N acetyldigoxin Chemical compound C1[C@H](OC(C)=O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O HWKJSYYYURVNQU-DXJNJSHLSA-N 0.000 title claims abstract description 16
- MGVYFNHJWXJYBE-UHFFFAOYSA-N alpha-Acetyl-digoxin Natural products CC1OC(CC(O)C1O)OC2C(O)CC(OC3C(C)OC(CC3OC(=O)C)OC4CCC5(C)C(CCC6C5CCC7(C)C(C(O)CC67O)C8=CC(=O)OC8)C4)OC2C MGVYFNHJWXJYBE-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 239000000203 mixture Substances 0.000 title claims description 14
- 238000000926 separation method Methods 0.000 title description 3
- HPMZBILYSWLILX-UMDUKNJSSA-N 3'''-O-acetyldigitoxin Chemical compound C1[C@H](OC(C)=O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O HPMZBILYSWLILX-UMDUKNJSSA-N 0.000 claims abstract description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 11
- HPMZBILYSWLILX-UHFFFAOYSA-N Acetyl-digitoxine Natural products C1C(OC(C)=O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O HPMZBILYSWLILX-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960003635 acetyldigitoxin Drugs 0.000 claims abstract description 9
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 claims abstract description 4
- 229960003304 acetyldigoxin Drugs 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 240000001879 Digitalis lutea Species 0.000 claims description 5
- 229930182470 glycoside Natural products 0.000 claims description 4
- 150000002338 glycosides Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 230000015556 catabolic process Effects 0.000 claims description 2
- 238000006731 degradation reaction Methods 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract description 10
- 230000003177 cardiotonic effect Effects 0.000 abstract 1
- 239000012044 organic layer Substances 0.000 abstract 1
- 238000000638 solvent extraction Methods 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000012071 phase Substances 0.000 description 4
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin Natural products O([C@H]1[C@H](C)O[C@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@](C)([C@H](O)C4)[C@H](C4=CC(=O)OC4)CC5)CC3)CC2)C[C@@H]1O)[C@H]1O[C@H](C)[C@@H](O[C@H]2O[C@@H](C)[C@H](O)[C@@H](O)C2)[C@@H](O)C1 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000006196 deacetylation Effects 0.000 description 2
- 238000003381 deacetylation reaction Methods 0.000 description 2
- 229960005156 digoxin Drugs 0.000 description 2
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 2
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 2
- 229930182478 glucoside Natural products 0.000 description 2
- 150000008131 glucosides Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- 229930188389 Lanatoside Natural products 0.000 description 1
- OJYGBLRPYBAHRT-UHFFFAOYSA-N alphachloralose Chemical compound O1C(C(Cl)(Cl)Cl)OC2C(O)C(C(O)CO)OC21 OJYGBLRPYBAHRT-UHFFFAOYSA-N 0.000 description 1
- 239000006286 aqueous extract Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 238000003403 chloroformylation reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT117567A AT267763B (de) | 1967-02-07 | 1967-02-07 | Verfahren zur Gewinnung von reinem Acetyldigoxin in der α-Form |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH495973A true CH495973A (de) | 1970-09-15 |
Family
ID=3508228
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH122968A CH495973A (de) | 1967-02-07 | 1968-01-26 | Verfahren zur Gewinnung von reinem Acetyldigoxin in der a-Form |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT267763B (cs) |
| CH (1) | CH495973A (cs) |
| CS (1) | CS165972B2 (cs) |
| DE (1) | DE1668239C3 (cs) |
| ES (1) | ES349660A1 (cs) |
| FR (1) | FR1568075A (cs) |
| GB (1) | GB1162614A (cs) |
| HU (1) | HU167287B (cs) |
| YU (2) | YU24368A (cs) |
-
1967
- 1967-02-07 AT AT117567A patent/AT267763B/de active
-
1968
- 1968-01-23 ES ES349660A patent/ES349660A1/es not_active Expired
- 1968-01-25 FR FR1568075D patent/FR1568075A/fr not_active Expired
- 1968-01-26 CH CH122968A patent/CH495973A/de not_active IP Right Cessation
- 1968-01-30 DE DE19681668239 patent/DE1668239C3/de not_active Expired
- 1968-02-01 GB GB529068A patent/GB1162614A/en not_active Expired
- 1968-02-02 YU YU24368A patent/YU24368A/xx unknown
- 1968-02-02 YU YU24568A patent/YU32287B/xx unknown
- 1968-02-06 CS CS91368A patent/CS165972B2/cs unknown
- 1968-02-06 HU HUHE000518 patent/HU167287B/hu unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU32287B (en) | 1974-08-31 |
| AT267763B (de) | 1969-01-10 |
| ES349660A1 (es) | 1969-04-01 |
| CS165972B2 (cs) | 1975-12-22 |
| HU167287B (cs) | 1975-09-27 |
| DE1668239A1 (de) | 1972-04-20 |
| YU24368A (en) | 1974-02-28 |
| DE1668239B2 (de) | 1973-05-30 |
| GB1162614A (en) | 1969-08-27 |
| DE1668239C3 (de) | 1974-01-17 |
| FR1568075A (cs) | 1969-05-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |