DE2410012A1 - 12-dehydrodigoxin-4'''- und 3'''-alkylaether und verfahren zu ihrer herstellung - Google Patents
12-dehydrodigoxin-4'''- und 3'''-alkylaether und verfahren zu ihrer herstellungInfo
- Publication number
- DE2410012A1 DE2410012A1 DE2410012A DE2410012A DE2410012A1 DE 2410012 A1 DE2410012 A1 DE 2410012A1 DE 2410012 A DE2410012 A DE 2410012A DE 2410012 A DE2410012 A DE 2410012A DE 2410012 A1 DE2410012 A1 DE 2410012A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- atoms
- dehydrodigoxin
- compound
- mono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 22
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 150000005215 alkyl ethers Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 230000010355 oscillation Effects 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 229960000583 acetic acid Drugs 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 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 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 229960005156 digoxin Drugs 0.000 description 5
- 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 5
- 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 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 4
- 229910001863 barium hydroxide Inorganic materials 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 229960003746 metildigoxin Drugs 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 150000008050 dialkyl sulfates Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 238000010626 work up procedure Methods 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940117975 chromium trioxide Drugs 0.000 description 2
- WGLPBDUCMAPZCE-UHFFFAOYSA-N chromium trioxide Inorganic materials O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 description 2
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- IYJMSDVSVHDVGT-PEQKVOOWSA-N metildigoxin Chemical compound O1[C@H](C)[C@@H](OC)[C@@H](O)C[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 IYJMSDVSVHDVGT-PEQKVOOWSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 preferably Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- FDWRIIDFYSUTDP-KVTDHHQDSA-N (2r,4r,5s,6r)-6-methyloxane-2,4,5-triol Chemical group C[C@H]1O[C@@H](O)C[C@@H](O)[C@@H]1O FDWRIIDFYSUTDP-KVTDHHQDSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FDWRIIDFYSUTDP-UHFFFAOYSA-N 102850-49-7 Natural products CC1OC(O)CC(O)C1O FDWRIIDFYSUTDP-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- JWFRNGYBHLBCMB-UHFFFAOYSA-N D-Canaytose Natural products CC(O)C(O)C(O)CC=O JWFRNGYBHLBCMB-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960003304 acetyldigoxin Drugs 0.000 description 1
- 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 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 206010003119 arrhythmia Diseases 0.000 description 1
- NREAGDHHMSOWKZ-UHFFFAOYSA-N beta-Acetyldigoxin Natural products CC1OC(OC2CC3C(C4C(C5(CCC(C5(C)C(O)C4)C=4COC(=O)C=4)O)CC3)(C)CC2)CC(O)C1OC(OC1C)CC(O)C1OC1CC(O)C(OC(C)=O)C(C)O1 NREAGDHHMSOWKZ-UHFFFAOYSA-N 0.000 description 1
- 230000003177 cardiotonic effect Effects 0.000 description 1
- 231100000457 cardiotoxic Toxicity 0.000 description 1
- 230000001451 cardiotoxic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C07J19/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410012A DE2410012A1 (de) | 1974-03-02 | 1974-03-02 | 12-dehydrodigoxin-4'''- und 3'''-alkylaether und verfahren zu ihrer herstellung |
| NL7502286A NL7502286A (nl) | 1974-03-02 | 1975-02-26 | 12-dehydrodigoxine-4"'- en 3'"-alkylethers, alsmede hun bereiding. |
| SE7502213A SE7502213L (enExample) | 1974-03-02 | 1975-02-27 | |
| GB8562/75A GB1499908A (en) | 1974-03-02 | 1975-02-28 | 12-dehydrodigoxin-(4'''and 3''')-monoalkyl ethers |
| AT155875A AT346498B (de) | 1974-03-02 | 1975-02-28 | Verfahren zur herstellung von neuen 12- dehydrodigoxinmono-4'' '-und-3'' '-alkylaethern |
| LU71940A LU71940A1 (enExample) | 1974-03-02 | 1975-02-28 | |
| DK81075*#A DK81075A (enExample) | 1974-03-02 | 1975-02-28 | |
| IE429/75A IE40701B1 (en) | 1974-03-02 | 1975-02-28 | 12-dehydro-digoxin-(4''' and 3''')-mono-alkyl ethers |
| US05/554,182 US3937697A (en) | 1974-03-02 | 1975-02-28 | 12-Dehydro digoxin-4'"-and 3'"-alkyl ethers |
| JP50024519A JPS50123660A (enExample) | 1974-03-02 | 1975-03-01 | |
| BE153942A BE826221A (fr) | 1974-03-02 | 1975-03-03 | Ethers alkyliques en 4''' et 3''' de la 12-dehydrodigoxine, leur procede de preparation et leurs applications |
| FR7506551A FR2262530A1 (enExample) | 1974-03-02 | 1975-03-03 | |
| AT97478A AT354660B (de) | 1974-03-02 | 1978-02-10 | Verfahren zur herstellung von neuen 12- dehydrodigoxinmono-4''-oder -3''-alkylaethern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2410012A DE2410012A1 (de) | 1974-03-02 | 1974-03-02 | 12-dehydrodigoxin-4'''- und 3'''-alkylaether und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2410012A1 true DE2410012A1 (de) | 1975-09-18 |
Family
ID=5908888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2410012A Withdrawn DE2410012A1 (de) | 1974-03-02 | 1974-03-02 | 12-dehydrodigoxin-4'''- und 3'''-alkylaether und verfahren zu ihrer herstellung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3937697A (enExample) |
| JP (1) | JPS50123660A (enExample) |
| AT (1) | AT346498B (enExample) |
| BE (1) | BE826221A (enExample) |
| DE (1) | DE2410012A1 (enExample) |
| DK (1) | DK81075A (enExample) |
| FR (1) | FR2262530A1 (enExample) |
| GB (1) | GB1499908A (enExample) |
| IE (1) | IE40701B1 (enExample) |
| LU (1) | LU71940A1 (enExample) |
| NL (1) | NL7502286A (enExample) |
| SE (1) | SE7502213L (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2550354A1 (de) * | 1975-11-10 | 1977-05-12 | Boehringer Mannheim Gmbh | Neue digoxin-derivate und verfahren zu ihrer herstellung |
| DE2926026A1 (de) * | 1979-06-28 | 1981-01-08 | Boehringer Mannheim Gmbh | Neue digoxin-derivate und verfahren zu ihrer herstellung |
-
1974
- 1974-03-02 DE DE2410012A patent/DE2410012A1/de not_active Withdrawn
-
1975
- 1975-02-26 NL NL7502286A patent/NL7502286A/xx not_active Application Discontinuation
- 1975-02-27 SE SE7502213A patent/SE7502213L/xx unknown
- 1975-02-28 IE IE429/75A patent/IE40701B1/xx unknown
- 1975-02-28 GB GB8562/75A patent/GB1499908A/en not_active Expired
- 1975-02-28 DK DK81075*#A patent/DK81075A/da unknown
- 1975-02-28 LU LU71940A patent/LU71940A1/xx unknown
- 1975-02-28 US US05/554,182 patent/US3937697A/en not_active Expired - Lifetime
- 1975-02-28 AT AT155875A patent/AT346498B/de not_active IP Right Cessation
- 1975-03-01 JP JP50024519A patent/JPS50123660A/ja active Pending
- 1975-03-03 FR FR7506551A patent/FR2262530A1/fr not_active Withdrawn
- 1975-03-03 BE BE153942A patent/BE826221A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK81075A (enExample) | 1975-11-03 |
| JPS50123660A (enExample) | 1975-09-29 |
| SE7502213L (enExample) | 1975-09-03 |
| BE826221A (fr) | 1975-09-03 |
| LU71940A1 (enExample) | 1977-01-06 |
| NL7502286A (nl) | 1975-09-04 |
| IE40701L (en) | 1975-09-02 |
| ATA155875A (de) | 1978-03-15 |
| IE40701B1 (en) | 1979-08-01 |
| US3937697A (en) | 1976-02-10 |
| GB1499908A (en) | 1978-02-01 |
| AT346498B (de) | 1978-11-10 |
| FR2262530A1 (enExample) | 1975-09-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee | ||
| 8141 | Disposal/no request for examination |