NO135789B - - Google Patents
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- Publication number
- NO135789B NO135789B NO699/70A NO69970A NO135789B NO 135789 B NO135789 B NO 135789B NO 699/70 A NO699/70 A NO 699/70A NO 69970 A NO69970 A NO 69970A NO 135789 B NO135789 B NO 135789B
- Authority
- NO
- Norway
- Prior art keywords
- proscillaridine
- acetic acid
- ethyl ester
- value
- acid ethyl
- Prior art date
Links
- 239000000203 mixture Substances 0.000 claims description 75
- 238000002425 crystallisation Methods 0.000 claims description 13
- 230000008025 crystallization Effects 0.000 claims description 13
- 239000002689 soil Substances 0.000 claims description 13
- 238000004587 chromatography analysis Methods 0.000 claims description 11
- 235000000346 sugar Nutrition 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000002170 ethers Chemical class 0.000 claims description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 254
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 96
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 42
- 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 41
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 22
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000007858 starting material Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 8
- 229910001863 barium hydroxide Inorganic materials 0.000 description 8
- 238000004440 column chromatography Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- -1 methoxyl group Chemical group 0.000 description 6
- 239000012053 oil suspension Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 229940097217 cardiac glycoside Drugs 0.000 description 5
- 239000002368 cardiac glycoside Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 229930002534 steroid glycoside Natural products 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 238000010626 work up procedure Methods 0.000 description 5
- 241000282326 Felis catus Species 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
- 230000000747 cardiac effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229930182470 glycoside Natural products 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 4
- 230000011987 methylation Effects 0.000 description 4
- 238000007069 methylation reaction Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 4
- 150000008143 steroidal glycosides Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XQCGNURMLWFQJR-ZNDDOCHDSA-N Cymarin Chemical compound O1[C@H](C)[C@@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)CC[C@@H]3[C@@]2(C=O)CC1 XQCGNURMLWFQJR-ZNDDOCHDSA-N 0.000 description 3
- XQCGNURMLWFQJR-UESCRGIISA-N Cymarin Natural products O=C[C@@]12[C@@](O)(C[C@@H](O[C@H]3O[C@@H](C)[C@@H](O)[C@@H](OC)C3)CC1)CC[C@H]1[C@]3(O)[C@@](C)([C@H](C4=CC(=O)OC4)CC3)CC[C@H]21 XQCGNURMLWFQJR-UESCRGIISA-N 0.000 description 3
- HKNQDCBTAOHPIM-UHFFFAOYSA-N Helveticosid Natural products CC1OCC(CC(O)C1O)OC2CCC3(C=O)C4CCC5(C)C(CCC5(O)C4CCC3(O)C2)C6=CC(=O)OC6 HKNQDCBTAOHPIM-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229960003083 cymarin Drugs 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 150000004679 hydroxides Chemical class 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 235000011121 sodium hydroxide Nutrition 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BLXSFCHWMBESKV-UHFFFAOYSA-N 1-iodopentane Chemical compound CCCCCI BLXSFCHWMBESKV-UHFFFAOYSA-N 0.000 description 2
- QWOJMRHUQHTCJG-UHFFFAOYSA-N CC([CH2-])=O Chemical compound CC([CH2-])=O QWOJMRHUQHTCJG-UHFFFAOYSA-N 0.000 description 2
- QBILRDAMJUPXCX-AGAUEGNUSA-N Helveticoside Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)CC[C@@H]3[C@@]2(C=O)CC1 QBILRDAMJUPXCX-AGAUEGNUSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001350 alkyl halides Chemical class 0.000 description 2
- QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- MPQBLCRFUYGBHE-XZBKPIIZSA-N (2r,3s,4r,5r)-2,4,5-trihydroxy-3-methoxyhexanal Chemical compound O=C[C@H](O)[C@@H](OC)[C@H](O)[C@@H](C)O MPQBLCRFUYGBHE-XZBKPIIZSA-N 0.000 description 1
- CTNPHHZPAJYPFO-PDXBGNJTSA-N (3s,5s,8r,9s,10s,13r,14s,17r)-3-[(2r,4s,5r,6r)-5-[(2r,3s,4s,5r,6s)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-methoxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-13-methyl-17-(5-oxo-2h-furan Chemical compound C1([C@@H]2[C@@]3(C)CC[C@@H]4[C@@]5(C=O)CC[C@@H](C[C@@]5(O)CC[C@H]4[C@@]3(O)CC2)O[C@H]2C[C@@H]([C@@H]([C@@H](C)O2)O[C@@H]2[C@H]([C@H](O)[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@H](CO)O2)O)OC)=CC(=O)OC1 CTNPHHZPAJYPFO-PDXBGNJTSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- VPUNMTHWNSJUOG-ZGEFSCNOSA-N 17beta-Neriifolin Natural products O(C)[C@@H]1[C@@H](O)[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)O[C@@H](C)[C@@H]1O VPUNMTHWNSJUOG-ZGEFSCNOSA-N 0.000 description 1
- GSOBLLOKFLTRQA-UHFFFAOYSA-N 2,4-dihydroxyphenyl-(6'-O-benzoyl)-O-beta-D-allopyranoside Natural products O1C(OC=2C(=CC(O)=CC=2)O)C(O)C(O)C(O)C1COC(=O)C1=CC=CC=C1 GSOBLLOKFLTRQA-UHFFFAOYSA-N 0.000 description 1
- GZVMBXDQUQRICT-TZNWHQCUSA-N 3-[(3s,5r,8r,9s,10s,13r,14s)-14-hydroxy-3-[(2s,3r,4r,5r,6s)-3-hydroxy-4-methoxy-6-methyl-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-10,13-dimethyl-1,2,3,4,5,6, Chemical compound C1([C@@]2(C)CC[C@H]3[C@H]([C@]2(CC1)O)CC[C@H]1[C@]3(C)CC[C@@H](C1)O[C@@H]1[C@H](O)[C@H]([C@@H]([C@H](C)O1)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)O1)O)OC)C1=CC(=O)OC1 GZVMBXDQUQRICT-TZNWHQCUSA-N 0.000 description 1
- OWAPJGMMSJMEHY-RPANTMAYSA-N 3-[(8S,9S,10R,13S,14R,17S)-10-(hydroxymethyl)-13-methyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one Chemical class OC[C@@]12CCCCC2CC[C@@H]2[C@@H]1CC[C@@]1(C)[C@@H]2CC[C@@H]1C=1COC(=O)C=1 OWAPJGMMSJMEHY-RPANTMAYSA-N 0.000 description 1
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- SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
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- 101100520260 Dictyostelium discoideum prosc gene Proteins 0.000 description 1
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- 125000001033 ether group Chemical group 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 125000003563 glycoside group Chemical group 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
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- 150000004694 iodide salts Chemical class 0.000 description 1
- VPUNMTHWNSJUOG-BAOINKAISA-N neriifolin Chemical compound O[C@H]1[C@H](OC)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@H](CC[C@H]2[C@]3(CC[C@@H]([C@@]3(C)CC[C@H]32)C=2COC(=O)C=2)O)[C@]3(C)CC1 VPUNMTHWNSJUOG-BAOINKAISA-N 0.000 description 1
- JLPDBLFIVFSOCC-XYXFTTADSA-N oleandrin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C[C@@H](CC[C@H]2[C@]3(C[C@@H]([C@@H]([C@@]3(C)CC[C@H]32)C=2COC(=O)C=2)OC(C)=O)O)[C@]3(C)CC1 JLPDBLFIVFSOCC-XYXFTTADSA-N 0.000 description 1
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- GOYBREOSJSERKM-ACZMJKKPSA-N oleandrose Chemical compound O=CC[C@H](OC)[C@@H](O)[C@H](C)O GOYBREOSJSERKM-ACZMJKKPSA-N 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- PMTSPAGBAFCORP-HBUONDEYSA-N peruvoside Chemical compound O[C@H]1[C@H](OC)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@H](CC[C@H]2[C@]3(CC[C@@H]([C@@]3(C)CC[C@H]32)C=2COC(=O)C=2)O)[C@]3(C=O)CC1 PMTSPAGBAFCORP-HBUONDEYSA-N 0.000 description 1
- 229960004180 peruvoside Drugs 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000012746 preparative thin layer chromatography Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 238000000870 ultraviolet spectroscopy 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1910207A DE1910207C3 (de) | 1969-02-28 | 1969-02-28 | Verfahren zu deren Herstellung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135789B true NO135789B (de) | 1977-02-21 |
| NO135789C NO135789C (de) | 1977-06-08 |
Family
ID=5726675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO699/70A NO135789C (de) | 1969-02-28 | 1970-02-27 |
Country Status (20)
| Country | Link |
|---|---|
| US (1) | US3726857A (de) |
| JP (1) | JPS512471B1 (de) |
| AT (1) | AT299456B (de) |
| BE (1) | BE746576A (de) |
| BG (1) | BG17560A3 (de) |
| BR (1) | BR7017112D0 (de) |
| CH (1) | CH532566A (de) |
| CS (1) | CS168524B2 (de) |
| DE (1) | DE1910207C3 (de) |
| DK (1) | DK128418B (de) |
| ES (1) | ES377027A1 (de) |
| FI (1) | FI47184C (de) |
| FR (1) | FR2034576B1 (de) |
| GB (1) | GB1266251A (de) |
| IE (1) | IE34036B1 (de) |
| IL (1) | IL33952A (de) |
| NL (1) | NL164287C (de) |
| NO (1) | NO135789C (de) |
| SE (1) | SE374915B (de) |
| YU (1) | YU33976B (de) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| NL7307741A (de) * | 1972-06-05 | 1973-12-07 | ||
| DE2341023A1 (de) * | 1973-08-14 | 1975-03-06 | Hoechst Ag | Neue herzglykoside und verfahren zu ihrer herstellung |
| DE2404268C2 (de) * | 1974-01-30 | 1982-09-16 | Knoll Ag, 6700 Ludwigshafen | Proscillaridinäther und Verfahren zu ihrer Herstellung |
| DE2427976C2 (de) * | 1974-06-10 | 1985-12-12 | Knoll Ag, 6700 Ludwigshafen | Proscillaridinäther, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel |
| AT349159B (de) * | 1974-07-09 | 1979-03-26 | Laevosan Gmbh & Co Kg | Verfahren zur herstellung neuer bufadienolid- und bufatrienolidaether |
| AT368523B (de) * | 1977-06-08 | 1982-10-25 | Laevosan Gmbh & Co Kg | Verfahren zur herstellung von bufadienolid- und bufatrienolidaethern |
| DE2841074A1 (de) * | 1978-09-21 | 1980-04-03 | Basf Ag | 4,5-methano-bufadienolid-rhamnoside, verfahren zu deren herstellung und diese enthaltende arzneimittel |
| JPS60147030A (ja) * | 1984-01-09 | 1985-08-02 | Matsushita Electric Ind Co Ltd | 高電圧発生装置 |
| CA2819635A1 (en) | 2010-12-01 | 2012-06-07 | Spinal Modulation, Inc. | Directed delivery of agents to neural anatomy |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6717599A (de) * | 1966-12-30 | 1968-07-01 | ||
| LU55588A1 (de) * | 1967-03-18 | 1968-05-06 |
-
1969
- 1969-02-28 DE DE1910207A patent/DE1910207C3/de not_active Expired
-
1970
- 1970-02-18 CH CH233570A patent/CH532566A/de not_active IP Right Cessation
- 1970-02-24 IL IL33952A patent/IL33952A/xx unknown
- 1970-02-24 BG BG014042A patent/BG17560A3/xx unknown
- 1970-02-25 GB GB1266251D patent/GB1266251A/en not_active Expired
- 1970-02-25 US US00014218A patent/US3726857A/en not_active Expired - Lifetime
- 1970-02-25 NL NL7002669.A patent/NL164287C/xx not_active IP Right Cessation
- 1970-02-26 YU YU479/70A patent/YU33976B/xx unknown
- 1970-02-26 IE IE251/70A patent/IE34036B1/xx unknown
- 1970-02-26 BE BE746576D patent/BE746576A/xx not_active IP Right Cessation
- 1970-02-26 AT AT180070A patent/AT299456B/de not_active IP Right Cessation
- 1970-02-26 CS CS1329A patent/CS168524B2/cs unknown
- 1970-02-27 BR BR217112/70A patent/BR7017112D0/pt unknown
- 1970-02-27 NO NO699/70A patent/NO135789C/no unknown
- 1970-02-27 FI FI700538A patent/FI47184C/fi active
- 1970-02-27 FR FR7007228A patent/FR2034576B1/fr not_active Expired
- 1970-02-27 JP JP45016945A patent/JPS512471B1/ja active Pending
- 1970-02-27 SE SE7002608A patent/SE374915B/xx unknown
- 1970-02-27 DK DK98170AA patent/DK128418B/da not_active IP Right Cessation
- 1970-02-28 ES ES377027A patent/ES377027A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE34036L (en) | 1970-08-28 |
| US3726857A (en) | 1973-04-10 |
| SE374915B (de) | 1975-03-24 |
| NO135789C (de) | 1977-06-08 |
| NL7002669A (de) | 1970-09-01 |
| FI47184B (de) | 1973-07-02 |
| IL33952A0 (en) | 1970-04-20 |
| FR2034576B1 (de) | 1974-05-24 |
| ES377027A1 (es) | 1972-05-16 |
| JPS512471B1 (de) | 1976-01-26 |
| NL164287B (nl) | 1980-07-15 |
| FR2034576A1 (de) | 1970-12-11 |
| BG17560A3 (bg) | 1973-11-10 |
| IE34036B1 (en) | 1975-01-08 |
| DE1910207C3 (de) | 1978-04-13 |
| BE746576A (fr) | 1970-08-26 |
| DK128418B (da) | 1974-04-29 |
| AT299456B (de) | 1972-06-26 |
| FI47184C (fi) | 1973-10-10 |
| CS168524B2 (de) | 1976-06-29 |
| GB1266251A (de) | 1972-03-08 |
| YU47970A (en) | 1978-02-28 |
| DE1910207B2 (de) | 1977-08-04 |
| CH532566A (de) | 1973-01-15 |
| DE1910207A1 (de) | 1970-09-17 |
| IL33952A (en) | 1974-03-14 |
| YU33976B (en) | 1978-09-08 |
| NL164287C (nl) | 1980-12-15 |
| BR7017112D0 (pt) | 1973-05-17 |
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