SU511015A3 - Способ получени ацилпроизводных дигоксина - Google Patents
Способ получени ацилпроизводных дигоксинаInfo
- Publication number
- SU511015A3 SU511015A3 SU1737660A SU1737660A SU511015A3 SU 511015 A3 SU511015 A3 SU 511015A3 SU 1737660 A SU1737660 A SU 1737660A SU 1737660 A SU1737660 A SU 1737660A SU 511015 A3 SU511015 A3 SU 511015A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- digoxin
- acid
- ester
- yield
- general formula
- Prior art date
Links
- 229960005156 digoxin Drugs 0.000 title claims 23
- 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 title claims 17
- 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 title claims 17
- 238000000034 method Methods 0.000 title claims 4
- 125000002252 acyl group Chemical group 0.000 title claims 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 claims 15
- 150000002148 esters Chemical class 0.000 claims 11
- -1 cyclic ortho ester Chemical class 0.000 claims 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 230000002378 acidificating effect Effects 0.000 claims 3
- 239000011260 aqueous acid Substances 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 150000002905 orthoesters Chemical class 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 2
- 238000006460 hydrolysis reaction Methods 0.000 claims 2
- 239000012442 inert solvent Substances 0.000 claims 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- KOPMZTKUZCNGFY-UHFFFAOYSA-N 1,1,1-triethoxybutane Chemical compound CCCC(OCC)(OCC)OCC KOPMZTKUZCNGFY-UHFFFAOYSA-N 0.000 claims 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- 239000005639 Lauric acid Substances 0.000 claims 1
- 239000002841 Lewis acid Substances 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- 239000003377 acid catalyst Substances 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229920001429 chelating resin Polymers 0.000 claims 1
- 125000002668 chloroacetyl group Chemical group ClCC(=O)* 0.000 claims 1
- QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 claims 1
- 238000003776 cleavage reaction Methods 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002500 ions Chemical class 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 150000007517 lewis acids Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 125000005489 p-toluenesulfonic acid group Chemical class 0.000 claims 1
- 229960003424 phenylacetic acid Drugs 0.000 claims 1
- 239000003279 phenylacetic acid Substances 0.000 claims 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000007127 saponification reaction Methods 0.000 claims 1
- 230000007017 scission Effects 0.000 claims 1
- 239000010802 sludge Substances 0.000 claims 1
- 229910052938 sodium sulfate Inorganic materials 0.000 claims 1
- 235000011152 sodium sulphate Nutrition 0.000 claims 1
- 239000000243 solution Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 238000005406 washing Methods 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/075—Ethers or acetals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Steroid Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712101595 DE2101595A1 (de) | 1971-01-14 | 1971-01-14 | Neue Acylderivate des Digoxins und Verfahren zu deren Herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU511015A3 true SU511015A3 (ru) | 1976-04-15 |
Family
ID=5795884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1737660A SU511015A3 (ru) | 1971-01-14 | 1972-01-14 | Способ получени ацилпроизводных дигоксина |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3804825A (enExample) |
| AT (1) | AT317444B (enExample) |
| AU (1) | AU465777B2 (enExample) |
| BE (1) | BE778014A (enExample) |
| BG (2) | BG18877A3 (enExample) |
| CA (1) | CA962665A (enExample) |
| CH (2) | CH571025A5 (enExample) |
| CS (1) | CS178403B2 (enExample) |
| DE (1) | DE2101595A1 (enExample) |
| DK (1) | DK126938B (enExample) |
| ES (2) | ES398804A1 (enExample) |
| FI (1) | FI51359C (enExample) |
| FR (1) | FR2121851B1 (enExample) |
| GB (1) | GB1371937A (enExample) |
| HU (1) | HU162743B (enExample) |
| IE (1) | IE36060B1 (enExample) |
| IL (1) | IL38550A (enExample) |
| NL (1) | NL7200446A (enExample) |
| PH (1) | PH10692A (enExample) |
| PL (1) | PL82940B1 (enExample) |
| RO (2) | RO68217A (enExample) |
| SE (1) | SE379048B (enExample) |
| SU (1) | SU511015A3 (enExample) |
| ZA (1) | ZA72241B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987031A (en) * | 1970-12-23 | 1976-10-19 | Boehringer Ingelheim Gmbh | Acyl derivatives of proscillaridin a |
| DE2354119A1 (de) * | 1973-10-29 | 1975-05-15 | Boehringer Sohn Ingelheim | Neue orthoformiatderivate des digitoxins, verfahren zu deren herstellung sowie diese enthaltende arzneimittel |
| US3884905A (en) * | 1974-05-02 | 1975-05-20 | Interx Research Corp | Pro-drug forms of digoxin |
| US4021535A (en) * | 1975-01-14 | 1977-05-03 | Beckman Instruments, Inc. | Reagents used in the radioimmunoassay of digoxin |
| EP1202056A1 (en) * | 2000-10-30 | 2002-05-02 | Vrije Universiteit Amsterdam | Continuous-flow homogeneous bio-chemical assays based on mass spectrometric detection of known ligands |
| CN112552367B (zh) * | 2020-12-11 | 2023-06-06 | 郑州安图生物工程股份有限公司 | 一种地高辛衍生物及其制备方法 |
-
1971
- 1971-01-14 DE DE19712101595 patent/DE2101595A1/de active Pending
-
1972
- 1972-01-03 BG BG022617A patent/BG18877A3/xx unknown
- 1972-01-05 US US00215666A patent/US3804825A/en not_active Expired - Lifetime
- 1972-01-11 BG BG019442A patent/BG18190A3/xx unknown
- 1972-01-12 HU HUBO1345A patent/HU162743B/hu unknown
- 1972-01-12 NL NL7200446A patent/NL7200446A/xx unknown
- 1972-01-12 ES ES398804A patent/ES398804A1/es not_active Expired
- 1972-01-12 SE SE7200327A patent/SE379048B/xx unknown
- 1972-01-12 PH PH13181A patent/PH10692A/en unknown
- 1972-01-13 FI FI720070A patent/FI51359C/fi active
- 1972-01-13 ZA ZA720241A patent/ZA72241B/xx unknown
- 1972-01-13 DK DK16872AA patent/DK126938B/da unknown
- 1972-01-13 CH CH46072A patent/CH571025A5/xx not_active IP Right Cessation
- 1972-01-13 IL IL38550A patent/IL38550A/en unknown
- 1972-01-13 CS CS230A patent/CS178403B2/cs unknown
- 1972-01-13 PL PL1972152879A patent/PL82940B1/pl unknown
- 1972-01-13 CH CH720075A patent/CH575435A5/xx not_active IP Right Cessation
- 1972-01-13 CA CA132,333A patent/CA962665A/en not_active Expired
- 1972-01-13 AU AU37868/72A patent/AU465777B2/en not_active Expired
- 1972-01-13 GB GB172972A patent/GB1371937A/en not_active Expired
- 1972-01-13 BE BE778014A patent/BE778014A/xx unknown
- 1972-01-14 FR FR7201256A patent/FR2121851B1/fr not_active Expired
- 1972-01-14 AT AT32772A patent/AT317444B/de not_active IP Right Cessation
- 1972-01-14 IE IE55/72A patent/IE36060B1/xx unknown
- 1972-01-14 SU SU1737660A patent/SU511015A3/ru active
- 1972-01-14 RO RO7271661A patent/RO68217A/ro unknown
- 1972-01-14 RO RO7200069393A patent/RO62477A/ro unknown
- 1972-04-17 ES ES401836A patent/ES401836A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CS178403B2 (enExample) | 1977-09-15 |
| AU3786872A (en) | 1973-07-19 |
| FI51359B (enExample) | 1976-08-31 |
| ZA72241B (en) | 1973-09-26 |
| CH571025A5 (enExample) | 1975-12-31 |
| FI51359C (fi) | 1976-12-10 |
| PH10692A (en) | 1977-08-10 |
| ES398804A1 (es) | 1974-08-16 |
| BG18190A3 (bg) | 1974-09-02 |
| NL7200446A (enExample) | 1972-07-18 |
| RO68217A (ro) | 1982-02-26 |
| IE36060L (en) | 1972-07-14 |
| HU162743B (enExample) | 1973-04-28 |
| IE36060B1 (en) | 1976-08-04 |
| SE379048B (enExample) | 1975-09-22 |
| IL38550A (en) | 1974-11-29 |
| FR2121851A1 (enExample) | 1972-08-25 |
| GB1371937A (en) | 1974-10-30 |
| PL82940B1 (enExample) | 1975-10-31 |
| IL38550A0 (en) | 1972-03-28 |
| RO62477A (fr) | 1978-03-15 |
| DE2101595A1 (de) | 1972-07-27 |
| CH575435A5 (enExample) | 1976-05-14 |
| DK126938B (da) | 1973-09-03 |
| BG18877A3 (bg) | 1975-03-20 |
| AT317444B (de) | 1974-08-26 |
| BE778014A (fr) | 1972-07-13 |
| US3804825A (en) | 1974-04-16 |
| ES401836A1 (es) | 1975-03-16 |
| AU465777B2 (en) | 1975-10-09 |
| CA962665A (en) | 1975-02-11 |
| FR2121851B1 (enExample) | 1975-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| SU628822A3 (ru) | Способ получени хлоргидрата 4 -эпи-6 оксиадриамицина | |
| SU511015A3 (ru) | Способ получени ацилпроизводных дигоксина | |
| James et al. | 194. The chemistry of gum tragacanth. Part II. Derivatives of d-and l-fucose | |
| US5101023A (en) | Process for synthesising azido-3'-deoxythymidine and analogs | |
| US3539629A (en) | Process for producing tetraacetyl derivatives of diamines | |
| SU508176A3 (ru) | Способ получени аминопроизводных бензофенона | |
| SU505358A3 (ru) | Способ получени производных пиперазина | |
| Wolfrom et al. | Acyclic Acetates of Dialdoses1 | |
| SU607549A3 (ru) | Способ получени производных карбалкокситиоуреидобензола | |
| SU474141A3 (ru) | Способ получени производных 6 ,16 -диметилстероидов | |
| IL36330A (en) | Preparation of acetyl history of steroid glycosides ingested activity on heart | |
| SU396344A1 (ru) | Вп тб | |
| US2687413A (en) | Preparation of alkali metal penicillinates | |
| CN113620832B (zh) | 一种非布司他中间体的制备方法 | |
| JPS589117B2 (ja) | ジギトキシゲニン−α−Ｌ−アラビ／シドの新規誘導体の製法 | |
| SU383373A1 (ru) | Способ получени динатриевой соли дисульфида 3,3-дипропандисульфокислоты | |
| SU915423A1 (ru) | Способ получения 1-аминотетразола1 | |
| US4018792A (en) | 5-Cyano-thiophen-2-aldehyde-isothiosemicarbazones and process for preparing them | |
| JPH021454A (ja) | アシルオキシアルカンスルホン酸の塩を製造する方法 | |
| JPH0348194B2 (enExample) | ||
| SU420173A3 (ru) | Способ получения ацилпроизводнб1х просцилларидина а | |
| US2103558A (en) | Phosphates of amino acid esters and method of producing same | |
| US3042707A (en) | Process for making esters of substituted polyhydronaphthalene acids | |
| SU391137A1 (ru) | Способ получения нитроксильных радикалов | |
| SU423293A3 (ru) | СПОСОБ ПОЛУЧЕНИЯ5а, 21-ДИБРОМ-бр-ФТОРПРОИЗВОДНЫХРЯДА ПРЕГНАНА |