SE442015B - Sett att framstella bufadienolid- och bufatrienolidetrar - Google Patents
Sett att framstella bufadienolid- och bufatrienolidetrarInfo
- Publication number
- SE442015B SE442015B SE7806364A SE7806364A SE442015B SE 442015 B SE442015 B SE 442015B SE 7806364 A SE7806364 A SE 7806364A SE 7806364 A SE7806364 A SE 7806364A SE 442015 B SE442015 B SE 442015B
- Authority
- SE
- Sweden
- Prior art keywords
- solution
- mmol
- titanium tetrachloride
- carbon atoms
- dioxane
- Prior art date
Links
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 43
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 claims description 33
- 239000003054 catalyst Substances 0.000 claims description 18
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 15
- -1 alkyl radical Chemical class 0.000 claims description 14
- 239000004327 boric acid Substances 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 9
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- 239000010936 titanium Substances 0.000 claims description 5
- JMXKSZRRTHPKDL-UHFFFAOYSA-N titanium ethoxide Chemical compound [Ti+4].CC[O-].CC[O-].CC[O-].CC[O-] JMXKSZRRTHPKDL-UHFFFAOYSA-N 0.000 claims description 5
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- YBPMPRDOWHIVNA-XTBIJCDISA-N bufadienolide Chemical compound C=1([C@H]2CC[C@@H]3[C@H]4[C@@H]([C@]5(CCCCC5CC4)C)CC[C@@]32C)C=CC(=O)OC=1 YBPMPRDOWHIVNA-XTBIJCDISA-N 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
- HAJGVUYNXHQLER-UHFFFAOYSA-N Bufadienolide Natural products O1C(=O)C=CC(C2C3C(C4C(C5CCCCC5CC4)CC3)CC2)=C1 HAJGVUYNXHQLER-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000853 cresyl group Chemical group C1(=CC=C(C=C1)C)* 0.000 claims description 2
- 239000012442 inert solvent Substances 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 claims 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 150000002170 ethers Chemical class 0.000 claims 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N ethyl methyl diketone Natural products CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 claims 1
- 229930182470 glycoside Natural products 0.000 claims 1
- 150000002338 glycosides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 238000001953 recrystallisation Methods 0.000 description 10
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 5
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- RYSXWUYLAWPLES-MTOQALJVSA-N (Z)-4-hydroxypent-3-en-2-one titanium Chemical compound [Ti].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RYSXWUYLAWPLES-MTOQALJVSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
- 238000005804 alkylation reaction Methods 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Chemical group C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- HJTAZXHBEBIQQX-UHFFFAOYSA-N 1,5-bis(chloromethyl)naphthalene Chemical compound C1=CC=C2C(CCl)=CC=CC2=C1CCl HJTAZXHBEBIQQX-UHFFFAOYSA-N 0.000 description 1
- BCEBOAVUYVQOIR-UHFFFAOYSA-N 1-chloro-2-diazoethane Chemical compound ClCC=[N+]=[N-] BCEBOAVUYVQOIR-UHFFFAOYSA-N 0.000 description 1
- XAROELXRWZQTTG-UHFFFAOYSA-N 1-diazo-2-methoxyethane Chemical compound COCC=[N+]=[N-] XAROELXRWZQTTG-UHFFFAOYSA-N 0.000 description 1
- ZSKNZBAJUNEUJA-UHFFFAOYSA-N 1-diazo-3-methoxypropane Chemical compound COCCC=[N+]=[N-] ZSKNZBAJUNEUJA-UHFFFAOYSA-N 0.000 description 1
- BZWJDKJBAVXCMH-UHFFFAOYSA-N 1-diazopropane Chemical compound CCC=[N+]=[N-] BZWJDKJBAVXCMH-UHFFFAOYSA-N 0.000 description 1
- IUWXVUQWEZTBCT-UHFFFAOYSA-N 3-[(z)-diazomethyl]heptane Chemical compound CCCCC(CC)C=[N+]=[N-] IUWXVUQWEZTBCT-UHFFFAOYSA-N 0.000 description 1
- NWWZHYJYBALBGJ-UHFFFAOYSA-N 3-diazo-N,N-dimethylpropan-1-amine Chemical compound CN(C)CCC=[N+]=[N-] NWWZHYJYBALBGJ-UHFFFAOYSA-N 0.000 description 1
- CTZFBSDRSZNOBE-UHFFFAOYSA-N 3-diazoprop-1-yne Chemical compound [N-]=[N+]=CC#C CTZFBSDRSZNOBE-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 description 1
- PZIQGAZNKPSARD-UHFFFAOYSA-N [(2z)-2-diazoethyl]benzene Chemical compound [N-]=[N+]=CCC1=CC=CC=C1 PZIQGAZNKPSARD-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- SMZOGRDCAXLAAR-UHFFFAOYSA-N aluminium isopropoxide Chemical compound [Al+3].CC(C)[O-].CC(C)[O-].CC(C)[O-] SMZOGRDCAXLAAR-UHFFFAOYSA-N 0.000 description 1
- GOLCXWYRSKYTSP-UHFFFAOYSA-N arsenic trioxide Inorganic materials O1[As]2O[As]1O2 GOLCXWYRSKYTSP-UHFFFAOYSA-N 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000005997 bromomethyl group Chemical group 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- 125000006203 morpholinoethyl group Chemical group [H]C([H])(*)C([H])([H])N1C([H])([H])C([H])([H])OC([H])([H])C1([H])[H] 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
- C07J71/0005—Oxygen-containing hetero ring
- C07J71/001—Oxiranes
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Hospice & Palliative Care (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
- Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT0405677A AT368523B (de) | 1977-06-08 | 1977-06-08 | Verfahren zur herstellung von bufadienolid- und bufatrienolidaethern |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7806364L SE7806364L (sv) | 1978-12-09 |
| SE442015B true SE442015B (sv) | 1985-11-25 |
Family
ID=3559053
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7806364A SE442015B (sv) | 1977-06-08 | 1978-05-31 | Sett att framstella bufadienolid- och bufatrienolidetrar |
Country Status (17)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2325467B (en) * | 1997-05-21 | 2000-11-01 | Dainippon Ink & Chemicals | Process for producing material with hydrophilic surface |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1905725A1 (de) * | 1969-02-06 | 1970-08-20 | Boehringer Mannheim Gmbh | Acovenosid-A-Derivate und Verfahren zur Herstellung derselben |
| DE1910207C3 (de) * | 1969-02-28 | 1978-04-13 | Knoll Ag, 6700 Ludwigshafen | Verfahren zu deren Herstellung |
| DE2404268C2 (de) * | 1974-01-30 | 1982-09-16 | Knoll Ag, 6700 Ludwigshafen | Proscillaridinäther und Verfahren zu ihrer Herstellung |
| AT349159B (de) * | 1974-07-09 | 1979-03-26 | Laevosan Gmbh & Co Kg | Verfahren zur herstellung neuer bufadienolid- und bufatrienolidaether |
-
1977
- 1977-06-08 AT AT0405677A patent/AT368523B/de not_active IP Right Cessation
-
1978
- 1978-05-23 CH CH557778A patent/CH637145A5/de not_active IP Right Cessation
- 1978-05-26 GB GB22676/78A patent/GB1601539A/en not_active Expired
- 1978-05-29 NL NL7805797A patent/NL7805797A/xx not_active Application Discontinuation
- 1978-05-29 YU YU1279/78A patent/YU40194B/xx unknown
- 1978-05-31 IT IT24056/78A patent/IT1109164B/it active
- 1978-05-31 SE SE7806364A patent/SE442015B/sv not_active IP Right Cessation
- 1978-06-02 IL IL7854850A patent/IL54850A0/xx unknown
- 1978-06-02 DE DE19782824318 patent/DE2824318A1/de active Granted
- 1978-06-06 FR FR787816874A patent/FR2393813A2/fr active Granted
- 1978-06-06 JP JP6733378A patent/JPS5416463A/ja active Granted
- 1978-06-07 ES ES470578A patent/ES470578A2/es not_active Expired
- 1978-06-07 CA CA304,930A patent/CA1107720A/en not_active Expired
- 1978-06-07 FI FI781823A patent/FI62844C/fi not_active IP Right Cessation
- 1978-06-07 EG EG365/78A patent/EG13431A/xx active
- 1978-06-08 LU LU79783A patent/LU79783A1/xx unknown
- 1978-06-08 BE BE188429A patent/BE867944A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ATA405677A (de) | 1982-02-15 |
| LU79783A1 (fr) | 1978-11-28 |
| CH637145A5 (en) | 1983-07-15 |
| YU40194B (en) | 1985-08-31 |
| FI62844B (fi) | 1982-11-30 |
| DE2824318A1 (de) | 1978-12-21 |
| FI62844C (fi) | 1983-03-10 |
| YU127978A (en) | 1982-10-31 |
| DE2824318C2 (enrdf_load_stackoverflow) | 1987-10-01 |
| BE867944A (fr) | 1978-10-02 |
| IT7824056A0 (it) | 1978-05-31 |
| FR2393813A2 (fr) | 1979-01-05 |
| SE7806364L (sv) | 1978-12-09 |
| FI781823A7 (fi) | 1978-12-09 |
| GB1601539A (en) | 1981-10-28 |
| AT368523B (de) | 1982-10-25 |
| JPS6213359B2 (enrdf_load_stackoverflow) | 1987-03-25 |
| FR2393813B2 (enrdf_load_stackoverflow) | 1982-08-27 |
| IT1109164B (it) | 1985-12-16 |
| IL54850A0 (en) | 1978-08-31 |
| JPS5416463A (en) | 1979-02-07 |
| EG13431A (en) | 1982-06-30 |
| CA1107720A (en) | 1981-08-25 |
| NL7805797A (nl) | 1978-12-12 |
| ES470578A2 (es) | 1979-04-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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