DE2136654A1 - 14,15 beta-epoxycardenolid- und 14,15 beta-epoxybufadienolid-glykoside und verfahren zu ihrer herstellung - Google Patents
14,15 beta-epoxycardenolid- und 14,15 beta-epoxybufadienolid-glykoside und verfahren zu ihrer herstellungInfo
- Publication number
- DE2136654A1 DE2136654A1 DE2136654A DE2136654A DE2136654A1 DE 2136654 A1 DE2136654 A1 DE 2136654A1 DE 2136654 A DE2136654 A DE 2136654A DE 2136654 A DE2136654 A DE 2136654A DE 2136654 A1 DE2136654 A1 DE 2136654A1
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- hydroxy
- mean
- beta
- epoxycardenolide
- 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 5
- 229930182470 glycoside Natural products 0.000 title description 9
- 150000002338 glycosides Chemical class 0.000 title description 9
- 238000004519 manufacturing process Methods 0.000 title 1
- 239000002253 acid Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- SQEBMLCQNJOCBG-HVHJFMEUSA-N (5s)-3-(hydroxymethyl)-5-methoxy-4-methyl-5-[(e)-2-phenylethenyl]furan-2-one Chemical compound C=1C=CC=CC=1/C=C/[C@]1(OC)OC(=O)C(CO)=C1C SQEBMLCQNJOCBG-HVHJFMEUSA-N 0.000 claims description 3
- FBMORZZOJSDNRQ-UHFFFAOYSA-N Demethoxy,B,HCl-Adriamycin Natural products C1C2C(=C)CCCC2(C)CC2(O)C1=C(C)C(=O)O2 FBMORZZOJSDNRQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000003172 aldehyde group Chemical group 0.000 claims description 3
- JUTMAMXOAOYKHT-UHFFFAOYSA-N karrikinolide Natural products C1=COC=C2OC(=O)C(C)=C21 JUTMAMXOAOYKHT-UHFFFAOYSA-N 0.000 claims description 3
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000003944 halohydrins Chemical class 0.000 claims description 2
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical class O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 5
- 239000012043 crude product Substances 0.000 description 5
- LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 5
- 229910001958 silver carbonate Inorganic materials 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
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 description 3
- 150000008463 L-rhamnopyranosides Chemical class 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AZUYLZMQTIKGSC-UHFFFAOYSA-N 1-[6-[4-(5-chloro-6-methyl-1H-indazol-4-yl)-5-methyl-3-(1-methylindazol-5-yl)pyrazol-1-yl]-2-azaspiro[3.3]heptan-2-yl]prop-2-en-1-one Chemical compound ClC=1C(=C2C=NNC2=CC=1C)C=1C(=NN(C=1C)C1CC2(CN(C2)C(C=C)=O)C1)C=1C=C2C=NN(C2=CC=1)C AZUYLZMQTIKGSC-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JTPOKVNLEAJBLN-UHFFFAOYSA-N Diffugenin Natural products CC12CCC(C3(CCC(O)CC3(O)CC3)C=O)C3C1=CCC2C1=CC(=O)OC1 JTPOKVNLEAJBLN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 2
- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 2
- LPARRDGBTTTYTR-UHFFFAOYSA-N 5-(3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,16,17-dodecahydro-1h-cyclopenta[a]phenanthren-17-yl)pyran-2-one Chemical compound CC12CCC(C3(CCC(O)CC3CC3)C)C3C1=CCC2C=1C=CC(=O)OC=1 LPARRDGBTTTYTR-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 206010048610 Cardiotoxicity Diseases 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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 238000006994 Koenigs-Knorr glycosidation reaction Methods 0.000 description 1
- 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 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- -1 aliphatic acyl radical Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 231100000259 cardiotoxicity Toxicity 0.000 description 1
- 230000007681 cardiovascular toxicity Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 238000005858 glycosidation reaction Methods 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- FQGYCXFLEQVDJQ-UHFFFAOYSA-N mercury dicyanide Chemical compound N#C[Hg]C#N FQGYCXFLEQVDJQ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000004165 myocardium Anatomy 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000003232 p-nitrobenzoyl group Chemical group [N+](=O)([O-])C1=CC=C(C(=O)*)C=C1 0.000 description 1
- 230000009090 positive inotropic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 229930190098 proscillaridin Natural products 0.000 description 1
- 229960003584 proscillaridin Drugs 0.000 description 1
- 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 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000008265 rhamnosides Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001923 silver oxide Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003431 steroids Chemical class 0.000 description 1
- 231100000397 ulcer Toxicity 0.000 description 1
- 238000010626 work up procedure 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
-
- 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
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/24—Condensed ring systems having three or more rings
- C07H15/256—Polyterpene radicals
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE786645D BE786645A (fr) | 1971-07-22 | Heterosides de 14,15 beta -epoxy-cardenolides et de 14,15 beta -epoxy bufadienolides et medicaments qui en renferment | |
| DE2136654A DE2136654A1 (de) | 1971-07-22 | 1971-07-22 | 14,15 beta-epoxycardenolid- und 14,15 beta-epoxybufadienolid-glykoside und verfahren zu ihrer herstellung |
| CA146,694A CA977334A (en) | 1971-07-22 | 1972-07-10 | 14,15.beta.-EPOXYCARDENOLIDE- AND 14,15.beta.-EPOXYBUFADIENOLIDE-GLYCOSIDES AND PROCESS FOR THEIR PREPARATION |
| ES404915A ES404915A1 (es) | 1971-07-22 | 1972-07-15 | Procedimiento para la preparacion de 3 beta - hidroxi - 14,15 beta - epoxi - 5 beta -cardenolid - o - 5 beta - bufadi- enolid - glicosidos. |
| NL7209860A NL7209860A (enExample) | 1971-07-22 | 1972-07-17 | |
| GB3325672A GB1389033A (en) | 1971-07-22 | 1972-07-17 | Cardenolide- and buadienolide-glycosides and process for their preparation |
| CH1079872A CH574975A5 (enExample) | 1971-07-22 | 1972-07-19 | |
| IL39945A IL39945A0 (en) | 1971-07-22 | 1972-07-19 | 14,15beta-epoxycardenolide-and 14,15beta-epoxybufadienolideglycosides and process for their preparation |
| DD164529A DD97417A5 (enExample) | 1971-07-22 | 1972-07-19 | |
| AR243166A AR194257A1 (es) | 1971-07-22 | 1972-07-20 | Procedimiento para la preparacion de 3beta-hidroxi-14,15beta-epoxi-5-beta-cardenoli-o 5-beta-bufadienolid-glicosidos |
| AU44747/72A AU4474772A (en) | 1971-07-22 | 1972-07-20 | 14, 15b-EPOXYCARBENOLIDE AND 14, 15b-EPOXYBUFADIENOLIDEGLYCOSIDES AND PROCESS FOR THEIR PREPARATION |
| ZA725058A ZA725058B (en) | 1971-07-22 | 1972-07-21 | 14,15beta-epoxycardenolide-and 14,15beta-epoxybufadienolide glycosides and process for their preparation |
| US274106A US3919191A (en) | 1971-07-22 | 1972-07-21 | 14,15{62 -Epoxycardenolide- and 14,15{62 -epoxybufadienolide-glycosides and process for their preparation |
| HUHO1501A HU163556B (enExample) | 1971-07-22 | 1972-07-21 | |
| IE1020/72A IE36579B1 (en) | 1971-07-22 | 1972-07-21 | Cardenolide- and bufadienolide- glycosides and process for their preparation |
| FR7226394A FR2146475B1 (enExample) | 1971-07-22 | 1972-07-21 | |
| AT630472A AT332565B (de) | 1971-07-22 | 1972-07-21 | Verfahren zur herstellung von neuen 14,15beta-epoxycardenolid- und 14,15beta-epoxybufadienolid-glycosiden |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2136654A DE2136654A1 (de) | 1971-07-22 | 1971-07-22 | 14,15 beta-epoxycardenolid- und 14,15 beta-epoxybufadienolid-glykoside und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2136654A1 true DE2136654A1 (de) | 1973-02-01 |
Family
ID=5814458
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2136654A Pending DE2136654A1 (de) | 1971-07-22 | 1971-07-22 | 14,15 beta-epoxycardenolid- und 14,15 beta-epoxybufadienolid-glykoside und verfahren zu ihrer herstellung |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3919191A (enExample) |
| AR (1) | AR194257A1 (enExample) |
| AT (1) | AT332565B (enExample) |
| AU (1) | AU4474772A (enExample) |
| BE (1) | BE786645A (enExample) |
| CA (1) | CA977334A (enExample) |
| CH (1) | CH574975A5 (enExample) |
| DD (1) | DD97417A5 (enExample) |
| DE (1) | DE2136654A1 (enExample) |
| ES (1) | ES404915A1 (enExample) |
| FR (1) | FR2146475B1 (enExample) |
| GB (1) | GB1389033A (enExample) |
| HU (1) | HU163556B (enExample) |
| IE (1) | IE36579B1 (enExample) |
| IL (1) | IL39945A0 (enExample) |
| NL (1) | NL7209860A (enExample) |
| ZA (1) | ZA725058B (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2841074A1 (de) * | 1978-09-21 | 1980-04-03 | Basf Ag | 4,5-methano-bufadienolid-rhamnoside, verfahren zu deren herstellung und diese enthaltende arzneimittel |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH421093A (de) * | 1962-04-11 | 1966-09-30 | Sandoz Ag | Verfahren zur Herstellung von neuen Steroiden |
| US3398138A (en) * | 1966-05-24 | 1968-08-20 | American Home Prod | Novel cardenolides and derivatives |
| DE1812946C3 (de) * | 1968-12-05 | 1978-11-02 | Hoechst Ag, 6000 Frankfurt | Herzwirksame 14beta, lSbeta Oxidobutatrienolide und Verfahren zu ihrer Herstellung |
| US3585186A (en) * | 1969-01-31 | 1971-06-15 | American Cyanamid Co | Preparation of glycopyranosiduronides and glycopyranosides and products resulting therefrom |
-
0
- BE BE786645D patent/BE786645A/xx unknown
-
1971
- 1971-07-22 DE DE2136654A patent/DE2136654A1/de active Pending
-
1972
- 1972-07-10 CA CA146,694A patent/CA977334A/en not_active Expired
- 1972-07-15 ES ES404915A patent/ES404915A1/es not_active Expired
- 1972-07-17 NL NL7209860A patent/NL7209860A/xx unknown
- 1972-07-17 GB GB3325672A patent/GB1389033A/en not_active Expired
- 1972-07-19 DD DD164529A patent/DD97417A5/xx unknown
- 1972-07-19 IL IL39945A patent/IL39945A0/xx unknown
- 1972-07-19 CH CH1079872A patent/CH574975A5/xx not_active IP Right Cessation
- 1972-07-20 AU AU44747/72A patent/AU4474772A/en not_active Expired
- 1972-07-20 AR AR243166A patent/AR194257A1/es active
- 1972-07-21 AT AT630472A patent/AT332565B/de not_active IP Right Cessation
- 1972-07-21 ZA ZA725058A patent/ZA725058B/xx unknown
- 1972-07-21 IE IE1020/72A patent/IE36579B1/xx unknown
- 1972-07-21 FR FR7226394A patent/FR2146475B1/fr not_active Expired
- 1972-07-21 HU HUHO1501A patent/HU163556B/hu unknown
- 1972-07-21 US US274106A patent/US3919191A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| IE36579B1 (en) | 1976-12-08 |
| HU163556B (enExample) | 1973-09-27 |
| IL39945A0 (en) | 1972-09-28 |
| DD97417A5 (enExample) | 1973-05-05 |
| FR2146475A1 (enExample) | 1973-03-02 |
| ES404915A1 (es) | 1975-06-16 |
| US3919191A (en) | 1975-11-11 |
| AU4474772A (en) | 1974-01-24 |
| AT332565B (de) | 1976-10-11 |
| AR194257A1 (es) | 1973-06-29 |
| CA977334A (en) | 1975-11-04 |
| ATA630472A (de) | 1976-01-15 |
| BE786645A (fr) | 1973-01-24 |
| ZA725058B (en) | 1973-04-25 |
| CH574975A5 (enExample) | 1976-04-30 |
| GB1389033A (en) | 1975-04-03 |
| NL7209860A (enExample) | 1973-01-24 |
| FR2146475B1 (enExample) | 1975-06-20 |
| IE36579L (en) | 1973-01-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| OHN | Withdrawal |