JPS5851960B2 - ジゴキシンノ ｃ２２−アルキル−ユウドウタイノセイホウ - Google Patents
ジゴキシンノ ｃ２２−アルキル−ユウドウタイノセイホウInfo
- Publication number
- JPS5851960B2 JPS5851960B2 JP50045117A JP4511775A JPS5851960B2 JP S5851960 B2 JPS5851960 B2 JP S5851960B2 JP 50045117 A JP50045117 A JP 50045117A JP 4511775 A JP4511775 A JP 4511775A JP S5851960 B2 JPS5851960 B2 JP S5851960B2
- Authority
- JP
- Japan
- Prior art keywords
- group
- alkyl
- chloroform
- digoxin
- conventional manner
- 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.)
- Expired
Links
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 10
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin Chemical class 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 description 5
- 239000012312 sodium hydride Substances 0.000 claims description 5
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 3
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 3
- 150000001351 alkyl iodides Chemical class 0.000 claims description 2
- 125000001118 alkylidene group Chemical group 0.000 claims description 2
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 229960005156 digoxin Drugs 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-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
- 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
- 229960003746 metildigoxin Drugs 0.000 description 5
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- -1 cardenolide glycoside Chemical class 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000006239 protecting group Chemical group 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GBBZLMLLFVFKJM-UHFFFAOYSA-N 1,2-diiodoethane Chemical compound ICCI GBBZLMLLFVFKJM-UHFFFAOYSA-N 0.000 description 1
- TYYDXNISHGVDGA-UHFFFAOYSA-N Corotoxigenin Natural products CC12CCC3C(CCC4CC(O)CCC34C=O)C1CCC2C5=CC(=O)OC5 TYYDXNISHGVDGA-UHFFFAOYSA-N 0.000 description 1
- BJNXJPYKYOKYOR-UHFFFAOYSA-N [C].ClC(Cl)Cl Chemical compound [C].ClC(Cl)Cl BJNXJPYKYOKYOR-UHFFFAOYSA-N 0.000 description 1
- 238000006359 acetalization reaction Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2418127A DE2418127A1 (de) | 1974-04-13 | 1974-04-13 | C22-alkyl-derivate des alpha- und beta-methyldigoxins und verfahren zur herstellung derselben |
| DE19742433563 DE2433563C2 (de) | 1974-07-12 | 1974-07-12 | Verfahren zur Herstellung von C22- Alkyl-Derivaten des Digoxins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS50137970A JPS50137970A (enrdf_load_stackoverflow) | 1975-11-01 |
| JPS5851960B2 true JPS5851960B2 (ja) | 1983-11-19 |
Family
ID=25766973
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP50045117A Expired JPS5851960B2 (ja) | 1974-04-13 | 1975-04-14 | ジゴキシンノ ｃ２２−アルキル−ユウドウタイノセイホウ |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS5851960B2 (enrdf_load_stackoverflow) |
| AR (1) | AR202973A1 (enrdf_load_stackoverflow) |
| CA (1) | CA1033714A (enrdf_load_stackoverflow) |
| ES (1) | ES436458A1 (enrdf_load_stackoverflow) |
| FI (1) | FI54317C (enrdf_load_stackoverflow) |
| FR (1) | FR2267328B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1449804A (enrdf_load_stackoverflow) |
| NL (1) | NL7504091A (enrdf_load_stackoverflow) |
| SE (1) | SE396392B (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61171714U (enrdf_load_stackoverflow) * | 1985-04-12 | 1986-10-24 |
-
1975
- 1975-01-01 AR AR20297375D patent/AR202973A1/es active
- 1975-04-02 CA CA223,698A patent/CA1033714A/en not_active Expired
- 1975-04-07 NL NL7504091A patent/NL7504091A/xx not_active Application Discontinuation
- 1975-04-08 FI FI751053A patent/FI54317C/fi not_active IP Right Cessation
- 1975-04-08 SE SE7504005A patent/SE396392B/xx unknown
- 1975-04-09 GB GB1459675A patent/GB1449804A/en not_active Expired
- 1975-04-09 ES ES436458A patent/ES436458A1/es not_active Expired
- 1975-04-11 FR FR7511370A patent/FR2267328B1/fr not_active Expired
- 1975-04-14 JP JP50045117A patent/JPS5851960B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS61171714U (enrdf_load_stackoverflow) * | 1985-04-12 | 1986-10-24 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2267328A1 (enrdf_load_stackoverflow) | 1975-11-07 |
| JPS50137970A (enrdf_load_stackoverflow) | 1975-11-01 |
| CA1033714A (en) | 1978-06-27 |
| GB1449804A (en) | 1976-09-15 |
| FI54317C (fi) | 1978-11-10 |
| SE7504005L (sv) | 1975-10-14 |
| SE396392B (sv) | 1977-09-19 |
| FI751053A7 (enrdf_load_stackoverflow) | 1975-10-14 |
| AR202973A1 (es) | 1975-07-31 |
| AU8004375A (en) | 1976-10-14 |
| ES436458A1 (es) | 1977-01-01 |
| FR2267328B1 (enrdf_load_stackoverflow) | 1978-06-30 |
| NL7504091A (nl) | 1975-10-15 |
| FI54317B (fi) | 1978-07-31 |
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