CA1054593A - Bufatrienolide rhamnoside ethers and a process for their preparation - Google Patents
Bufatrienolide rhamnoside ethers and a process for their preparationInfo
- Publication number
- CA1054593A CA1054593A CA000228894A CA228894A CA1054593A CA 1054593 A CA1054593 A CA 1054593A CA 000228894 A CA000228894 A CA 000228894A CA 228894 A CA228894 A CA 228894A CA 1054593 A CA1054593 A CA 1054593A
- Authority
- CA
- Canada
- Prior art keywords
- proscillaridin
- process according
- methylether
- prepared
- formula
- 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
- 238000000034 method Methods 0.000 title claims description 30
- -1 rhamnoside ethers Chemical class 0.000 title description 5
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 title description 3
- MYEJFUXQJGHEQK-ALRJYLEOSA-N Proscillaridin Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 MYEJFUXQJGHEQK-ALRJYLEOSA-N 0.000 claims abstract description 34
- 229930190098 proscillaridin Natural products 0.000 claims abstract description 34
- 229960003584 proscillaridin Drugs 0.000 claims abstract description 34
- MYEJFUXQJGHEQK-UHFFFAOYSA-N proscillaridin A Natural products OC1C(O)C(O)C(C)OC1OC1C=C2CCC3C4(O)CCC(C5=COC(=O)C=C5)C4(C)CCC3C2(C)CC1 MYEJFUXQJGHEQK-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical group COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 claims description 11
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 230000001035 methylating effect Effects 0.000 claims description 6
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 4
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 150000007522 mineralic acids Chemical class 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical group C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 claims description 2
- 229910001863 barium hydroxide Inorganic materials 0.000 claims description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- CWLNAJYDRSIKJS-UHFFFAOYSA-N triethoxymethoxyethane Chemical compound CCOC(OCC)(OCC)OCC CWLNAJYDRSIKJS-UHFFFAOYSA-N 0.000 claims description 2
- 230000011987 methylation Effects 0.000 claims 5
- 238000007069 methylation reaction Methods 0.000 claims 5
- 239000000126 substance Substances 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- AHJWSRRHTXRLAQ-UHFFFAOYSA-N tetramethoxymethane Chemical compound COC(OC)(OC)OC AHJWSRRHTXRLAQ-UHFFFAOYSA-N 0.000 claims 2
- 230000003197 catalytic effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 206010019280 Heart failures Diseases 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- RLAHWVDQYNDAGG-UHFFFAOYSA-N Methanetriol Chemical compound OC(O)O RLAHWVDQYNDAGG-UHFFFAOYSA-N 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- RKWPZPDLTYBKCL-RVZGXXANSA-N meproscillarin Chemical compound O[C@@H]1[C@H](O)[C@@H](OC)[C@H](C)O[C@H]1O[C@@H]1C=C2CC[C@H]3[C@@]4(O)CC[C@H](C5=COC(=O)C=C5)[C@@]4(C)CC[C@@H]3[C@@]2(C)CC1 RKWPZPDLTYBKCL-RVZGXXANSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- RXCVUXLCNLVYIA-UHFFFAOYSA-N orthocarbonic acid Chemical compound OC(O)(O)O RXCVUXLCNLVYIA-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000004809 thin layer chromatography 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2427976A DE2427976C2 (de) | 1974-06-10 | 1974-06-10 | Proscillaridinäther, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054593A true CA1054593A (en) | 1979-05-15 |
Family
ID=5917784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000228894A Expired CA1054593A (en) | 1974-06-10 | 1975-06-09 | Bufatrienolide rhamnoside ethers and a process for their preparation |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS518274A (xx) |
| AT (1) | AT349160B (xx) |
| BE (1) | BE829998A (xx) |
| CA (1) | CA1054593A (xx) |
| CH (1) | CH594701A5 (xx) |
| DD (1) | DD120018A5 (xx) |
| DE (1) | DE2427976C2 (xx) |
| FI (1) | FI751725A (xx) |
| FR (1) | FR2273549A1 (xx) |
| GB (1) | GB1461051A (xx) |
| NL (1) | NL7506825A (xx) |
| SE (1) | SE7506571L (xx) |
| ZA (1) | ZA753082B (xx) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5348332A (en) * | 1976-10-15 | 1978-05-01 | Hitachi Ltd | Remote supervisory control system for dam gate |
| JPS58142654U (ja) * | 1982-03-23 | 1983-09-26 | 光武 量 | 風力・水力利用の磁力温水装置 |
| JPS58149719U (ja) * | 1982-03-31 | 1983-10-07 | 日本ハ−ゼン株式会社 | 医療用立体観察装置 |
| JPS60168434A (ja) * | 1984-02-13 | 1985-08-31 | 佐藤 富男 | 心胸郭比の測定装置 |
| JPH067708U (ja) * | 1992-06-30 | 1994-02-01 | トノクラ医科工業株式会社 | 心・胸郭比測定装置 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1910207C3 (de) * | 1969-02-28 | 1978-04-13 | Knoll Ag, 6700 Ludwigshafen | Verfahren zu deren Herstellung |
| BE759830A (fr) * | 1969-12-06 | 1971-06-03 | Hoechst Ag | Di-alkyl-orthocarbonates d'heterosides en 3 de cardenolides et de bufadienolides |
| DE2063406C3 (de) * | 1970-12-23 | 1978-05-03 | C.H. Boehringer Sohn, 6507 Ingelheim | Acylderivate des Proscillaridin A, Verfahren zu deren Herstellung und diese enthaltende Präparate |
| DE2217404C3 (de) * | 1972-04-11 | 1982-02-11 | Gödecke AG, 1000 Berlin | Neue herzwirksame Cardenolid-Rhamnoside |
-
1974
- 1974-06-10 DE DE2427976A patent/DE2427976C2/de not_active Expired
-
1975
- 1975-04-24 GB GB1695275A patent/GB1461051A/en not_active Expired
- 1975-05-13 ZA ZA00753082A patent/ZA753082B/xx unknown
- 1975-05-15 FR FR7515222A patent/FR2273549A1/fr active Granted
- 1975-06-06 DD DD186504A patent/DD120018A5/xx unknown
- 1975-06-06 CH CH728275A patent/CH594701A5/xx not_active IP Right Cessation
- 1975-06-09 SE SE7506571A patent/SE7506571L/xx unknown
- 1975-06-09 CA CA000228894A patent/CA1054593A/en not_active Expired
- 1975-06-09 AT AT436475A patent/AT349160B/de not_active IP Right Cessation
- 1975-06-09 BE BE157130A patent/BE829998A/xx not_active IP Right Cessation
- 1975-06-09 NL NL7506825A patent/NL7506825A/xx not_active Application Discontinuation
- 1975-06-10 JP JP50070096A patent/JPS518274A/ja active Granted
- 1975-06-10 FI FI751725A patent/FI751725A/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AT349160B (de) | 1979-03-26 |
| CH594701A5 (xx) | 1978-01-31 |
| BE829998A (fr) | 1975-12-09 |
| SE7506571L (sv) | 1975-12-11 |
| JPS518274A (en) | 1976-01-23 |
| JPS61357B2 (xx) | 1986-01-08 |
| GB1461051A (en) | 1977-01-13 |
| FI751725A (xx) | 1975-12-11 |
| NL7506825A (nl) | 1975-12-12 |
| DE2427976A1 (de) | 1976-01-02 |
| DD120018A5 (xx) | 1976-05-20 |
| FR2273549B1 (xx) | 1979-07-06 |
| FR2273549A1 (fr) | 1976-01-02 |
| DE2427976C2 (de) | 1985-12-12 |
| ZA753082B (en) | 1976-04-28 |
| ATA436475A (de) | 1978-08-15 |
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