DE1957246A1 - Verfahren zur Herstellung von 3beta-Hydroxy-5beta-cardenoliden - Google Patents
Verfahren zur Herstellung von 3beta-Hydroxy-5beta-cardenolidenInfo
- Publication number
- DE1957246A1 DE1957246A1 DE19691957246 DE1957246A DE1957246A1 DE 1957246 A1 DE1957246 A1 DE 1957246A1 DE 19691957246 DE19691957246 DE 19691957246 DE 1957246 A DE1957246 A DE 1957246A DE 1957246 A1 DE1957246 A1 DE 1957246A1
- Authority
- DE
- Germany
- Prior art keywords
- hydroxy
- cardenolides
- preparation
- iridium
- 5beta
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 3
- SNNJOYYRZHOKFM-QBFOWDOUSA-N 3-[(3s,5r,8r,9s,10s,13s,14r,17s)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2h-furan-5-one Chemical class C1([C@H]2CC[C@@H]3[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 SNNJOYYRZHOKFM-QBFOWDOUSA-N 0.000 title 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001298 alcohols Chemical class 0.000 claims description 4
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001447 alkali salts Chemical class 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 claims description 2
- MOHYGSBMXIJZBJ-UHFFFAOYSA-N [Ir+4] Chemical compound [Ir+4] MOHYGSBMXIJZBJ-UHFFFAOYSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- FFQCZYROKVPTGV-UHFFFAOYSA-N Cl.[Ir+4] Chemical compound Cl.[Ir+4] FFQCZYROKVPTGV-UHFFFAOYSA-N 0.000 description 4
- XZTUSOXSLKTKJQ-UHFFFAOYSA-N Uzarigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C1=CC(=O)OC1 XZTUSOXSLKTKJQ-UHFFFAOYSA-N 0.000 description 4
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- XZTUSOXSLKTKJQ-CESUGQOBSA-N digitoxigenin Chemical compound C1([C@H]2CC[C@]3(O)[C@H]4[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC4)C)CC[C@@]32C)=CC(=O)OC1 XZTUSOXSLKTKJQ-CESUGQOBSA-N 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229910052741 iridium Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- -1 saturated keto steroids Chemical class 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-N 0.000 description 2
- HXXNSZGESRDYFE-JIUSCHCVSA-N 1-[(8r,9s,10s,13s,14s,17s)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]-2-hydroxyethanone Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)C(=O)CO)[C@@H]4[C@@H]3CCC21 HXXNSZGESRDYFE-JIUSCHCVSA-N 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- JIUWTCXNUNHEGP-FEPOTVBBSA-N 3-[(5S,8R,9S,10S,13S,14R,17S)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one Chemical compound C[C@]12CC[C@H]3[C@@H](CC[C@@H]4CCCC[C@]34C)[C@H]1CC[C@@H]2C=1COC(=O)C=1 JIUWTCXNUNHEGP-FEPOTVBBSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 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
- QAQPABLODWMGOS-JVWMIROESA-N O=C1C[C@H]2CC[C@@H]3[C@H](CC[C@@]4(C)[C@@H]3CC[C@@H]4C=3COC(=O)C=3)[C@]2(CC1)C Chemical class O=C1C[C@H]2CC[C@@H]3[C@H](CC[C@@]4(C)[C@@H]3CC[C@@H]4C=3COC(=O)C=3)[C@]2(CC1)C QAQPABLODWMGOS-JVWMIROESA-N 0.000 description 1
- 241000282376 Panthera tigris Species 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- JIUWTCXNUNHEGP-GJHPUSIBSA-N cardenolide Chemical compound C1([C@H]2CC[C@@H]3[C@H]4[C@@H]([C@]5(CCCCC5CC4)C)CC[C@@]32C)=CC(=O)OC1 JIUWTCXNUNHEGP-GJHPUSIBSA-N 0.000 description 1
- 150000001738 cardenolides Chemical class 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006345 epimerization reaction Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002596 lactones Chemical group 0.000 description 1
- 229910052987 metal hydride Inorganic materials 0.000 description 1
- 150000004681 metal hydrides Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 230000010181 polygamy Effects 0.000 description 1
- WFIZEGIEIOHZCP-UHFFFAOYSA-M potassium formate Chemical compound [K+].[O-]C=O WFIZEGIEIOHZCP-UHFFFAOYSA-M 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000005406 washing Methods 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE758859D BE758859A (fr) | 1969-11-14 | Procede de preparation de cardenolides | |
| DE19691957246 DE1957246A1 (de) | 1969-11-14 | 1969-11-14 | Verfahren zur Herstellung von 3beta-Hydroxy-5beta-cardenoliden |
| BR215367/69A BR6915367D0 (pt) | 1969-11-14 | 1969-12-19 | Processo para a preparacao de 3 beta-hidroxi-5 beta-cardenolideos |
| NL7016368A NL7016368A (pt) | 1969-11-14 | 1970-11-09 | |
| CH1668070A CH529122A (de) | 1969-11-14 | 1970-11-11 | Verfahren zur Herstellung von 3B-Hydroxy-5B-cardenoliden |
| DK575770AA DK128351B (da) | 1969-11-14 | 1970-11-12 | Fremgangsmåde til fremstilling af 3β-hydroxy-5β-cardenolider fra 14-dehydro- eller 14β-hydroxyrækken. |
| FR7040701A FR2069360A5 (pt) | 1969-11-14 | 1970-11-13 | |
| GB5426170A GB1327438A (en) | 1969-11-14 | 1970-11-13 | Process for the manufacture of 3beta-hydroxy-5beta-card- 20-22- enolides |
| JP45100104A JPS5023027B1 (pt) | 1969-11-14 | 1970-11-13 | |
| CA098045A CA922692A (en) | 1969-11-14 | 1970-11-13 | PROCESS FOR THE MANUFACTURE OF 3 .beta.-HYDROXY-5 .beta.-CARDENOLIDES |
| AT1025570A AT306935B (de) | 1969-11-14 | 1970-11-13 | Verfahren zur Herstellung von 3β-Hydroxy-14-dehydro (bzw. 14β-hydroxy)-5β-cardenoliden |
| SE7015337A SE376619B (pt) | 1969-11-14 | 1970-11-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691957246 DE1957246A1 (de) | 1969-11-14 | 1969-11-14 | Verfahren zur Herstellung von 3beta-Hydroxy-5beta-cardenoliden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1957246A1 true DE1957246A1 (de) | 1971-05-19 |
Family
ID=5751058
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691957246 Pending DE1957246A1 (de) | 1969-11-14 | 1969-11-14 | Verfahren zur Herstellung von 3beta-Hydroxy-5beta-cardenoliden |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS5023027B1 (pt) |
| AT (1) | AT306935B (pt) |
| BE (1) | BE758859A (pt) |
| BR (1) | BR6915367D0 (pt) |
| CA (1) | CA922692A (pt) |
| CH (1) | CH529122A (pt) |
| DE (1) | DE1957246A1 (pt) |
| DK (1) | DK128351B (pt) |
| FR (1) | FR2069360A5 (pt) |
| GB (1) | GB1327438A (pt) |
| NL (1) | NL7016368A (pt) |
| SE (1) | SE376619B (pt) |
-
0
- BE BE758859D patent/BE758859A/xx unknown
-
1969
- 1969-11-14 DE DE19691957246 patent/DE1957246A1/de active Pending
- 1969-12-19 BR BR215367/69A patent/BR6915367D0/pt unknown
-
1970
- 1970-11-09 NL NL7016368A patent/NL7016368A/xx unknown
- 1970-11-11 CH CH1668070A patent/CH529122A/de not_active IP Right Cessation
- 1970-11-12 DK DK575770AA patent/DK128351B/da unknown
- 1970-11-13 GB GB5426170A patent/GB1327438A/en not_active Expired
- 1970-11-13 AT AT1025570A patent/AT306935B/de not_active IP Right Cessation
- 1970-11-13 SE SE7015337A patent/SE376619B/xx unknown
- 1970-11-13 JP JP45100104A patent/JPS5023027B1/ja active Pending
- 1970-11-13 CA CA098045A patent/CA922692A/en not_active Expired
- 1970-11-13 FR FR7040701A patent/FR2069360A5/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2069360A5 (pt) | 1971-09-03 |
| NL7016368A (pt) | 1971-05-18 |
| CA922692A (en) | 1973-03-13 |
| JPS5023027B1 (pt) | 1975-08-05 |
| AT306935B (de) | 1973-04-25 |
| DK128351B (da) | 1974-04-16 |
| BE758859A (fr) | 1971-05-12 |
| CH529122A (de) | 1972-10-15 |
| SE376619B (pt) | 1975-06-02 |
| BR6915367D0 (pt) | 1973-01-16 |
| GB1327438A (en) | 1973-08-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHN | Withdrawal |