NO130398B - - Google Patents
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- Publication number
- NO130398B NO130398B NO01384/69A NO138469A NO130398B NO 130398 B NO130398 B NO 130398B NO 01384/69 A NO01384/69 A NO 01384/69A NO 138469 A NO138469 A NO 138469A NO 130398 B NO130398 B NO 130398B
- Authority
- NO
- Norway
- Prior art keywords
- digitoxigenin
- water
- anhydro
- deoxy
- reaction
- Prior art date
Links
- 229930182470 glycoside Natural products 0.000 claims description 5
- 150000002338 glycosides Chemical class 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- XZTUSOXSLKTKJQ-UHFFFAOYSA-N Uzarigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C1=CC(=O)OC1 XZTUSOXSLKTKJQ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 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 claims description 4
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 235000015497 potassium bicarbonate Nutrition 0.000 description 2
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 2
- 239000011736 potassium bicarbonate Substances 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- -1 steroid alcohols Chemical class 0.000 description 2
- 238000002211 ultraviolet spectrum Methods 0.000 description 2
- OPHAQGBSVLXVOL-GGZOMVNGSA-N 1-[(2r,3r,4r)-4,6-diacetyl-3,4-dihydroxy-2-(hydroxymethyl)-2,3-dihydropyran-5-yl]ethanone Chemical compound CC(=O)C1=C(C(C)=O)[C@](O)(C(C)=O)[C@H](O)[C@@H](CO)O1 OPHAQGBSVLXVOL-GGZOMVNGSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- YBGJZYCWGNYUMA-UHFFFAOYSA-M [Cl-].[P+]=O Chemical compound [Cl-].[P+]=O YBGJZYCWGNYUMA-UHFFFAOYSA-M 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000001142 anti-diarrhea Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000297 inotrophic effect Effects 0.000 description 1
- 208000028774 intestinal disease Diseases 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19681768165 DE1768165C3 (de) | 1968-04-06 | Verfahren zur Herstellung von Digitoxigenin-Glykosiden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO130398B true NO130398B (cs) | 1974-08-26 |
Family
ID=5699623
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01384/69A NO130398B (cs) | 1968-04-06 | 1969-04-01 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3642770A (cs) |
| JP (1) | JPS5034024B1 (cs) |
| AT (1) | AT292928B (cs) |
| BE (1) | BE731175A (cs) |
| CH (1) | CH550158A (cs) |
| DK (1) | DK119765B (cs) |
| FI (1) | FI46067C (cs) |
| FR (1) | FR2007410A1 (cs) |
| GB (1) | GB1268230A (cs) |
| NL (1) | NL6904759A (cs) |
| NO (1) | NO130398B (cs) |
| SE (1) | SE343853B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3859272A (en) * | 1968-07-23 | 1975-01-07 | Hoechst Ag | 19-alkylene-14- ' -hydroxy-cardenolide derivatives and process for preparing them |
| BE755538A (fr) * | 1969-08-29 | 1971-03-01 | Hoechst Ag | Heterosides steroidiques et medicaments qui en contiennent |
| DE2237377A1 (de) * | 1972-07-29 | 1974-02-14 | Hoechst Ag | Verfahren zur herstellung von cardenolid-3-eckige klammer auf 2'-desoxyglykosiden eckige klammer zu |
| DE2256912C2 (de) * | 1972-11-20 | 1984-04-05 | Hoechst Ag, 6230 Frankfurt | Digoxigenin-3-[2',3'-didesoxy-glykoside], Verfahren zu ihrer Herstellung und deren Verwendung |
| US5496806A (en) * | 1990-01-23 | 1996-03-05 | R. Erich Klemke | Glycoside compounds and production and use thereof |
| DE4001895A1 (de) * | 1990-01-23 | 1991-07-25 | Harrier Gmbh | Herstellung von insbesondere steroidglykosiden |
| IL102566A0 (en) * | 1991-07-22 | 1993-01-14 | Harrier Inc | Glycoside compounds and production and use thereof |
| US5693769A (en) * | 1991-12-13 | 1997-12-02 | Transcell Technologies, Inc. | Glycosylated steroid derivatives for transport across biological membranes and process for making and using same |
| US5338837A (en) * | 1991-12-13 | 1994-08-16 | The Trustees Of Princeton University | Glycosylated steroid derivatives for transport across biological membranes and process for making same |
| US5795870A (en) * | 1991-12-13 | 1998-08-18 | Trustees Of Princeton University | Compositions and methods for cell transformation |
| CA2156717C (en) * | 1993-02-23 | 2001-05-29 | Daniel E. Kahne | Solution and solid-phase formation of glycosidic linkages |
| US5639866A (en) * | 1993-02-23 | 1997-06-17 | Princeton University | Single-step formation of multiple glycosidic linkages |
| CA2819635A1 (en) | 2010-12-01 | 2012-06-07 | Spinal Modulation, Inc. | Directed delivery of agents to neural anatomy |
-
1969
- 1969-03-24 FI FI690860A patent/FI46067C/fi active
- 1969-03-25 US US810358A patent/US3642770A/en not_active Expired - Lifetime
- 1969-03-27 NL NL6904759A patent/NL6904759A/xx not_active Application Discontinuation
- 1969-04-01 NO NO01384/69A patent/NO130398B/no unknown
- 1969-04-01 GB GB06961/69A patent/GB1268230A/en not_active Expired
- 1969-04-02 DK DK189469AA patent/DK119765B/da unknown
- 1969-04-03 CH CH519769A patent/CH550158A/xx not_active IP Right Cessation
- 1969-04-03 SE SE4827/69A patent/SE343853B/xx unknown
- 1969-04-04 AT AT336469A patent/AT292928B/de not_active IP Right Cessation
- 1969-04-07 JP JP44026559A patent/JPS5034024B1/ja active Pending
- 1969-04-08 BE BE731175D patent/BE731175A/xx unknown
- 1969-04-08 FR FR6910636A patent/FR2007410A1/fr not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| SE343853B (cs) | 1972-03-20 |
| DE1768165A1 (de) | 1971-10-14 |
| NL6904759A (cs) | 1969-10-08 |
| JPS5034024B1 (cs) | 1975-11-05 |
| CH550158A (de) | 1974-06-14 |
| GB1268230A (en) | 1972-03-22 |
| FI46067C (fi) | 1972-12-11 |
| FR2007410A1 (cs) | 1970-01-09 |
| FI46067B (cs) | 1972-08-31 |
| DE1768165B2 (de) | 1975-08-14 |
| AT292928B (de) | 1971-09-10 |
| US3642770A (en) | 1972-02-15 |
| DK119765B (da) | 1971-02-22 |
| BE731175A (cs) | 1969-10-08 |
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