DE2016704C3 - Ein neues, herzwirksames 14,15 ß -Oxidobufadienolid-LRhamnosid und Verfahren zu seiner Herstellung - Google Patents
Ein neues, herzwirksames 14,15 ß -Oxidobufadienolid-LRhamnosid und Verfahren zu seiner HerstellungInfo
- Publication number
- DE2016704C3 DE2016704C3 DE2016704A DE2016704A DE2016704C3 DE 2016704 C3 DE2016704 C3 DE 2016704C3 DE 2016704 A DE2016704 A DE 2016704A DE 2016704 A DE2016704 A DE 2016704A DE 2016704 C3 DE2016704 C3 DE 2016704C3
- Authority
- DE
- Germany
- Prior art keywords
- ecm
- heart
- preparation
- oxidobufadienolide
- lrhamnoside
- 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 6
- HRAYYNRXNPLKFE-UHFFFAOYSA-N L-rhamnopyranoside Natural products OC1C(O)C(O)C(C)OC1OC1C(O)C(OC2C(C(C)OC(OC=3C=C4C(C(C(OC5C(C(OC6C(C(O)C(O)C(C)O6)O)C(O)C(COC6C(C(O)C(O)C(CO)O6)O)O5)OC(=O)C=CC=5C=CC(O)=CC=5)=C(C=5C=CC(O)=CC=5)O4)=O)=C(O)C=3)C2O)OC(=O)C=CC=2C=CC(O)=CC=2)OC(C)C1O HRAYYNRXNPLKFE-UHFFFAOYSA-N 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 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 description 5
- 230000008018 melting Effects 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 229930190098 proscillaridin Natural products 0.000 description 5
- 229960003584 proscillaridin Drugs 0.000 description 5
- 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 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000002924 oxiranes Chemical class 0.000 description 4
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 4
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 150000003944 halohydrins Chemical class 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- -1 acyl radicals Chemical class 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930182470 glycoside Natural products 0.000 description 2
- 150000002338 glycosides Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- PTEWBCBLYXHSHI-UHFFFAOYSA-N BrNS(=O)=O Chemical class BrNS(=O)=O PTEWBCBLYXHSHI-UHFFFAOYSA-N 0.000 description 1
- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
- QEEBRPGZBVVINN-UHFFFAOYSA-N Desacetyl-bufotalin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C1(O)CCC2C=1C=CC(=O)OC=1 QEEBRPGZBVVINN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 150000008451 L-rhamnosides Chemical class 0.000 description 1
- JMNQTHQLNRILMH-UHFFFAOYSA-N Marinobufagin Natural products CC12CCC(C3(CCC(O)CC3(O)CC3)C)C3C11OC1CC2C=1C=CC(=O)OC=1 JMNQTHQLNRILMH-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- WPUJEWVVTKLMQI-UHFFFAOYSA-N benzene;ethoxyethane Chemical compound CCOCC.C1=CC=CC=C1 WPUJEWVVTKLMQI-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- ATLJNLYIJOCWJE-CWMZOUAVSA-N bufogenin Chemical compound C=1([C@H]2C[C@H]3O[C@@]43[C@H]3[C@@H]([C@]5(CC[C@H](O)C[C@H]5CC3)C)CC[C@@]42C)C=CC(=O)OC=1 ATLJNLYIJOCWJE-CWMZOUAVSA-N 0.000 description 1
- 229950006858 bufogenin Drugs 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003683 cardiac damage Effects 0.000 description 1
- 229940030602 cardiac therapy drug Drugs 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
- LHRSMZZXPVKEKR-UHFFFAOYSA-N chloromethane;ethyl acetate Chemical compound ClC.CCOC(C)=O LHRSMZZXPVKEKR-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- 239000012021 ethylating agents Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- JMNQTHQLNRILMH-OBBGIPBRSA-N marinobufagenin Chemical compound C=1([C@H]2C[C@H]3O[C@@]43[C@H]3[C@@H]([C@]5(CC[C@H](O)C[C@@]5(O)CC3)C)CC[C@@]42C)C=CC(=O)OC=1 JMNQTHQLNRILMH-OBBGIPBRSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- ATLJNLYIJOCWJE-UHFFFAOYSA-N resibufogenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C=1C=CC(=O)OC=1 ATLJNLYIJOCWJE-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J71/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Steroid Compounds (AREA)
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2016704A DE2016704C3 (de) | 1970-04-08 | 1970-04-08 | Ein neues, herzwirksames 14,15 ß -Oxidobufadienolid-LRhamnosid und Verfahren zu seiner Herstellung |
| ES389818A ES389818A1 (es) | 1970-04-08 | 1971-04-02 | Procedimiento para la preparacion de 3 beta - hidroxi-15,15beta-oxido-14 betabufa - 4,20,22 - trienolid, 3 beta - (alfa-l-ramnopiranosido). |
| NL7104435A NL7104435A (OSRAM) | 1970-04-08 | 1971-04-02 | |
| CA109542A CA929157A (en) | 1970-04-08 | 1971-04-05 | Cardioactive oxydo-bufadienolide and process for preparing it |
| AT293471A AT311562B (de) | 1970-04-08 | 1971-04-06 | Verfahren zur Herstellung des neuen 3β-Hydroxy-14,15β-oxydo-14β-bufa-4,20,22-trienolid, 3β-(α-L-Rhamnopyranosids) |
| FI710968A FI48075C (fi) | 1970-04-08 | 1971-04-06 | Menetelmä sydämen toimintaan vaikuttavan 3beta-hydroksi-14,15beta-oksi do-14beta-bufa-4,20,22-trienolidi, 3beta-(alfa-L-ramnopyranosidi):n va lmistamiseksi |
| US00131808A US3741955A (en) | 1970-04-08 | 1971-04-06 | 3beta-hydroxy - 14,15beta-oxido - 14beta-bufa-4,20,22-trienalide-3beta-(alpha-l-rhamnopyranoside) |
| BE765430A BE765430A (fr) | 1970-04-08 | 1971-04-07 | Nouvel epoxy-bufadienolide a activite cardiotrope et sa preparation |
| ZA712205A ZA712205B (en) | 1970-04-08 | 1971-04-07 | A new cardioactive oxydo-bufadienolide and process for preparing it |
| DK172371AA DK128112B (da) | 1970-04-08 | 1971-04-07 | Fremgangsmåde til fremstilling af 3β-hydroxy-14,15β-oxido-14β-bufa-4,20,22-trienolid,3β-(α-L-rhamnopyranosid). |
| FR7112466A FR2092021B1 (OSRAM) | 1970-04-08 | 1971-04-08 | |
| JP2205171A JPS5437139B1 (OSRAM) | 1970-04-08 | 1971-04-08 | |
| SE04644/71A SE366037B (OSRAM) | 1970-04-08 | 1971-04-08 | |
| CH517571A CH551963A (de) | 1970-04-08 | 1971-04-08 | Verfahren zur herstellung eines neuen herzwirksamen oxidobufadienolids. |
| GB2635971*A GB1315235A (en) | 1970-04-08 | 1971-04-19 | Cardioactive oxido-bufatrienolide and a process for its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2016704A DE2016704C3 (de) | 1970-04-08 | 1970-04-08 | Ein neues, herzwirksames 14,15 ß -Oxidobufadienolid-LRhamnosid und Verfahren zu seiner Herstellung |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2016704A1 DE2016704A1 (de) | 1971-10-21 |
| DE2016704B2 DE2016704B2 (de) | 1979-01-11 |
| DE2016704C3 true DE2016704C3 (de) | 1979-09-06 |
Family
ID=5767430
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2016704A Expired DE2016704C3 (de) | 1970-04-08 | 1970-04-08 | Ein neues, herzwirksames 14,15 ß -Oxidobufadienolid-LRhamnosid und Verfahren zu seiner Herstellung |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US3741955A (OSRAM) |
| JP (1) | JPS5437139B1 (OSRAM) |
| AT (1) | AT311562B (OSRAM) |
| BE (1) | BE765430A (OSRAM) |
| CA (1) | CA929157A (OSRAM) |
| CH (1) | CH551963A (OSRAM) |
| DE (1) | DE2016704C3 (OSRAM) |
| DK (1) | DK128112B (OSRAM) |
| ES (1) | ES389818A1 (OSRAM) |
| FI (1) | FI48075C (OSRAM) |
| FR (1) | FR2092021B1 (OSRAM) |
| GB (1) | GB1315235A (OSRAM) |
| NL (1) | NL7104435A (OSRAM) |
| SE (1) | SE366037B (OSRAM) |
| ZA (1) | ZA712205B (OSRAM) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2341023A1 (de) * | 1973-08-14 | 1975-03-06 | Hoechst Ag | Neue herzglykoside und verfahren zu ihrer herstellung |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1812946C3 (de) * | 1968-12-05 | 1978-11-02 | Hoechst Ag, 6000 Frankfurt | Herzwirksame 14beta, lSbeta Oxidobutatrienolide und Verfahren zu ihrer Herstellung |
-
1970
- 1970-04-08 DE DE2016704A patent/DE2016704C3/de not_active Expired
-
1971
- 1971-04-02 ES ES389818A patent/ES389818A1/es not_active Expired
- 1971-04-02 NL NL7104435A patent/NL7104435A/xx unknown
- 1971-04-05 CA CA109542A patent/CA929157A/en not_active Expired
- 1971-04-06 FI FI710968A patent/FI48075C/fi active
- 1971-04-06 US US00131808A patent/US3741955A/en not_active Expired - Lifetime
- 1971-04-06 AT AT293471A patent/AT311562B/de not_active IP Right Cessation
- 1971-04-07 DK DK172371AA patent/DK128112B/da unknown
- 1971-04-07 ZA ZA712205A patent/ZA712205B/xx unknown
- 1971-04-07 BE BE765430A patent/BE765430A/xx unknown
- 1971-04-08 FR FR7112466A patent/FR2092021B1/fr not_active Expired
- 1971-04-08 CH CH517571A patent/CH551963A/xx not_active IP Right Cessation
- 1971-04-08 SE SE04644/71A patent/SE366037B/xx unknown
- 1971-04-08 JP JP2205171A patent/JPS5437139B1/ja active Pending
- 1971-04-19 GB GB2635971*A patent/GB1315235A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT311562B (de) | 1973-11-26 |
| ZA712205B (en) | 1971-12-29 |
| FR2092021B1 (OSRAM) | 1974-05-24 |
| JPS5437139B1 (OSRAM) | 1979-11-13 |
| DE2016704B2 (de) | 1979-01-11 |
| NL7104435A (OSRAM) | 1971-10-12 |
| CH551963A (de) | 1974-07-31 |
| DK128112B (da) | 1974-03-04 |
| SE366037B (OSRAM) | 1974-04-08 |
| CA929157A (en) | 1973-06-26 |
| US3741955A (en) | 1973-06-26 |
| FI48075C (fi) | 1974-06-10 |
| BE765430A (fr) | 1971-10-07 |
| GB1315235A (en) | 1973-05-02 |
| FI48075B (OSRAM) | 1974-02-28 |
| FR2092021A1 (OSRAM) | 1972-01-21 |
| DE2016704A1 (de) | 1971-10-21 |
| ES389818A1 (es) | 1973-06-01 |
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