CH544752A - Verfahren zur Herstellung neuer Glucoside - Google Patents

Verfahren zur Herstellung neuer Glucoside

Info

Publication number: CH544752A
Authority: CH; Switzerland
Prior art keywords: demethyl; glucoside; epipodophyllotoxin; eipodophyllotoxin; water
Prior art date: 1966-12-13

Application number

CH1445369A

Other languages

German (de)

English (en)

Inventor

Keller-Juslen Camilla

Kuhn Max

Renz Jany

Wartburg Albert Von

Original Assignee

Sandoz Ag

Priority date (The priority date 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 date listed.)

1966-12-13

Filing date

1966-12-13

Publication date

1974-01-15

1966-12-13 Application filed by Sandoz Ag filed Critical Sandoz Ag

1966-12-13 Priority to CH1445369A priority Critical patent/CH544752A/de

1974-01-15 Publication of CH544752A publication Critical patent/CH544752A/de

Links

229930182478 glucoside Natural products 0.000 title claims description 7
241000699670 Mus sp. Species 0.000 title abstract description 3
230000001085 cytostatic effect Effects 0.000 title abstract description 3
239000000824 cytostatic agent Substances 0.000 title abstract 2
208000032839 leukemia Diseases 0.000 title abstract 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 9
230000007717 exclusion Effects 0.000 claims description 5
150000008131 glucosides Chemical class 0.000 claims description 5
238000002360 preparation method Methods 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
FOVRGQUEGRCWPD-BRLGUANISA-N (5s,5ar,8ar,9r)-9-(4-hydroxy-3,5-dimethoxyphenyl)-5-[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 FOVRGQUEGRCWPD-BRLGUANISA-N 0.000 claims description 3
239000012442 inert solvent Substances 0.000 claims description 3
239000011230 binding agent Substances 0.000 claims description 2
150000001768 cations Chemical class 0.000 claims description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
125000000542 sulfonic acid group Chemical group 0.000 claims description 2
150000003460 sulfonic acids Chemical class 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 3
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 8
201000009030 Carcinoma Diseases 0.000 abstract description 2
241000700159 Rattus Species 0.000 abstract description 2
208000001792 Sarcoma 37 Diseases 0.000 abstract description 2
210000002950 fibroblast Anatomy 0.000 abstract description 2
238000000338 in vitro Methods 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 2
125000003342 alkenyl group Chemical group 0.000 abstract 1
125000002947 alkylene group Chemical group 0.000 abstract 1
125000003710 aryl alkyl group Chemical group 0.000 abstract 1
125000003118 aryl group Chemical group 0.000 abstract 1
125000000753 cycloalkyl group Chemical group 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
239000000243 solution Substances 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
238000001035 drying Methods 0.000 description 5
239000012074 organic phase Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
FJJYHTVHBVXEEQ-UHFFFAOYSA-N 2,2-dimethylpropanal Chemical compound CC(C)(C)C=O FJJYHTVHBVXEEQ-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000126 substance Substances 0.000 description 4
FOVRGQUEGRCWPD-UHFFFAOYSA-N (5aR)-9t-beta-D-Glucopyranosyloxy-5t-(4-hydroxy-3,5-dimethoxy-phenyl)-(5ar,8at)-5,8,8a,9-tetrahydro-5aH-furo[3',4';6,7]naphtho[2,3-d][1,3]dioxol-6-on Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(OC3C(C(O)C(O)C(CO)O3)O)C3C2C(OC3)=O)=C1 FOVRGQUEGRCWPD-UHFFFAOYSA-N 0.000 description 3
YVCVYCSAAZQOJI-JHQYFNNDSA-N 4'-demethylepipodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-JHQYFNNDSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
150000001299 aldehydes Chemical class 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
239000003814 drug Substances 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
229910015900 BF3 Inorganic materials 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
229940057499 anhydrous zinc acetate Drugs 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Substances FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
-1 invert sugar Chemical compound 0.000 description 2
BCUMPULZWNQMKD-UHFFFAOYSA-N methanol;propan-2-yl acetate Chemical compound OC.CC(C)OC(C)=O BCUMPULZWNQMKD-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000843 powder Substances 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 2
NCVWKOWDCKUIPP-RKQHYHRCSA-N 1-[(2r,3r,4s,5s,6s)-4,5,6-triacetyl-3,4,5,6-tetrahydroxy-2-(hydroxymethyl)oxan-3-yl]ethanone Chemical compound CC(=O)[C@@]1(O)O[C@H](CO)[C@](O)(C(C)=O)[C@@](O)(C(C)=O)[C@]1(O)C(C)=O NCVWKOWDCKUIPP-RKQHYHRCSA-N 0.000 description 1
YVCVYCSAAZQOJI-BTINSWFASA-N 4'-demethylpodophyllotoxin Chemical compound COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YVCVYCSAAZQOJI-BTINSWFASA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products 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 1
206010028980 Neoplasm Diseases 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
IEOLRPPTIGNUNP-RKQHYHRCSA-N [(2r,3r,4s,5r,6r)-3,4,5-triacetyloxy-6-hydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O IEOLRPPTIGNUNP-RKQHYHRCSA-N 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
238000006136 alcoholysis reaction Methods 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
DNKYMRIVXIQCFO-UHFFFAOYSA-N benzene pentane Chemical compound CCCCC.CCCCC.C1=CC=CC=C1 DNKYMRIVXIQCFO-UHFFFAOYSA-N 0.000 description 1
WIRUZQNBHNAMAB-UHFFFAOYSA-N benzene;cyclohexane Chemical compound C1CCCCC1.C1=CC=CC=C1 WIRUZQNBHNAMAB-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
OAABHEHWRQAHEJ-UHFFFAOYSA-N butan-1-ol;chloroform Chemical compound ClC(Cl)Cl.CCCCO OAABHEHWRQAHEJ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
VZDYWEUILIUIDF-UHFFFAOYSA-J cerium(4+);disulfate Chemical compound [Ce+4].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O VZDYWEUILIUIDF-UHFFFAOYSA-J 0.000 description 1
229910000355 cerium(IV) sulfate Inorganic materials 0.000 description 1
SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000008298 dragée Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 1
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000006260 foam Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
201000006512 mast cell neoplasm Diseases 0.000 description 1
208000006971 mastocytoma Diseases 0.000 description 1
239000000155 melt Substances 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
230000009054 pathological process Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
YVCVYCSAAZQOJI-UHFFFAOYSA-N podophyllotoxin Natural products COC1=C(O)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YVCVYCSAAZQOJI-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000001226 reprecipitation Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
229960004793 sucrose Drugs 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CH1445369A 1966-12-13 1966-12-13 Verfahren zur Herstellung neuer Glucoside CH544752A (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CH1445369A CH544752A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date	Title
CH1445369A CH544752A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775466A CH481913A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775566A CH481095A (de)	1966-12-13	1966-12-13	Vefahren zur Herstellung neuer Glucoside
CH1775366A CH481094A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775966A CH481097A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung eines neuen Glucosids
CH1775666A CH481096A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775266A CH484101A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside

Publications (1)

Publication Number	Publication Date
CH544752A true CH544752A (de)	1974-01-15

Family

ID=27543911

Family Applications (7)

Application Number	Title	Priority Date	Filing Date
CH1445369A CH544752A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775966A CH481097A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung eines neuen Glucosids
CH1775566A CH481095A (de)	1966-12-13	1966-12-13	Vefahren zur Herstellung neuer Glucoside
CH1775266A CH484101A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775666A CH481096A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775366A CH481094A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775466A CH481913A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside

Family Applications After (6)

Application Number	Title	Priority Date	Filing Date
CH1775966A CH481097A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung eines neuen Glucosids
CH1775566A CH481095A (de)	1966-12-13	1966-12-13	Vefahren zur Herstellung neuer Glucoside
CH1775266A CH484101A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775666A CH481096A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775366A CH481094A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside
CH1775466A CH481913A (de)	1966-12-13	1966-12-13	Verfahren zur Herstellung neuer Glucoside

Country Status (12)

Country	Link
AT (1)	AT285062B (cs)
BE (1)	BE707822A (cs)
CA (1)	CA952103A (cs)
CH (7)	CH544752A (cs)
CS (1)	CS152448B2 (cs)
DE (1)	DE1643521C3 (cs)
DK (1)	DK131429B (cs)
FI (1)	FI48585C (cs)
FR (2)	FR1572185A (cs)
GB (2)	GB1205965A (cs)
NL (1)	NL6716635A (cs)
SE (1)	SE348192B (cs)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4713246A (en) *	1984-03-19	1987-12-15	Bristol-Myers Company	Etoposide oral dosage form
US4904768A (en) *	1987-08-04	1990-02-27	Bristol-Myers Company	Epipodophyllotoxin glucoside 4'-phosphate derivatives
US4935504A (en) *	1987-12-18	1990-06-19	Bristol-Myers Company	Epipodophyllotoxin glucoside 4'-acyl derivatives
KR910014122A (ko) *	1990-01-19	1991-08-31	디께다 가즈히꼬	에토포시드-2-디메틸아미노 화합물의 동결건조 제제
US5463040A (en) *	1994-06-28	1995-10-31	Teva Pharmaceutical Industries, Ltd.	Method of preparing etoposide
US6207673B1 (en)	1997-03-12	2001-03-27	The University Of North Carolina At Chapel Hill	Covalent conjugates of topoisomerase I and topoisomerase II inhibitors

1966
- 1966-12-13 CH CH1445369A patent/CH544752A/de not_active IP Right Cessation
- 1966-12-13 CH CH1775966A patent/CH481097A/de not_active IP Right Cessation
- 1966-12-13 CH CH1775566A patent/CH481095A/de not_active IP Right Cessation
- 1966-12-13 CH CH1775266A patent/CH484101A/de not_active IP Right Cessation
- 1966-12-13 CH CH1775666A patent/CH481096A/de not_active IP Right Cessation
- 1966-12-13 CH CH1775366A patent/CH481094A/de not_active IP Right Cessation
- 1966-12-13 CH CH1775466A patent/CH481913A/de not_active IP Right Cessation
1967
- 1967-11-27 GB GB5384467A patent/GB1205965A/en not_active Expired
- 1967-11-27 GB GB1946270A patent/GB1205966A/en not_active Expired
- 1967-12-07 NL NL6716635A patent/NL6716635A/xx unknown
- 1967-12-09 DE DE1967S0113215 patent/DE1643521C3/de not_active Expired
- 1967-12-11 CS CS877367A patent/CS152448B2/cs unknown
- 1967-12-11 FR FR1572185D patent/FR1572185A/fr not_active Expired
- 1967-12-11 CA CA007,216A patent/CA952103A/en not_active Expired
- 1967-12-11 BE BE707822D patent/BE707822A/xx not_active IP Right Cessation
- 1967-12-12 SE SE1706767A patent/SE348192B/xx unknown
- 1967-12-12 DK DK620967A patent/DK131429B/da not_active IP Right Cessation
- 1967-12-12 FI FI331067A patent/FI48585C/fi active
- 1967-12-12 AT AT1119667A patent/AT285062B/de not_active IP Right Cessation
1968
- 1968-03-08 FR FR142954A patent/FR8031M/fr not_active Expired

Also Published As

Publication number	Publication date
CH481094A (de)	1969-11-15
NL6716635A (cs)	1968-06-14
GB1205965A (en)	1970-09-23
CH481095A (de)	1969-11-15
BE707822A (cs)	1968-06-11
CS152448B2 (cs)	1973-12-19
GB1205966A (en)	1970-09-23
AT285062B (de)	1970-10-12
DK131429B (da)	1975-07-14
SE348192B (cs)	1972-08-28
DK131429C (cs)	1975-12-15
FR8031M (cs)	1970-08-03
DE1643521C3 (de)	1978-09-21
CH481097A (de)	1969-11-15
FI48585C (fi)	1974-11-11
CH481913A (de)	1969-11-30
CH481096A (de)	1969-11-15
FI48585B (cs)	1974-07-31
DE1643521A1 (de)	1971-04-08
DE1643521B2 (de)	1978-01-19
CH484101A (de)	1970-01-15
CA952103A (en)	1974-07-30
FR1572185A (cs)	1969-06-27

Legal Events

Date	Code	Title	Description
1981-08-31	PL	Patent ceased

Publication	Publication Date	Title
DE3851941T2 (de)	1995-04-27	Polycyclische aromatische Ester von makroliden Antibiotika und linkosamiden Antibiotika, Verfahren zu ihrer Herstellung und die sie enthaltenden pharmazeutischen und kosmetischen Zusammensetzungen.
DE1543891A1 (de)	1970-02-12	Ein neues Glucosid sowie ein Verfahren zu seiner Herstellung
CH514578A (de)	1971-10-31	Verfahren zur Herstellung von Glucosiden
CH544752A (de)	1974-01-15	Verfahren zur Herstellung neuer Glucoside
DE1276035B (de)	1968-08-29	4'-Monoester des Cymarols und Verfahren zu deren Herstellung
EP0022504B1 (de)	1983-03-16	1-N-Alkylsisomicin-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
DE2733867B2 (de)	1980-10-30	Oleandomycinderivate und diese Verbindungen enthaltende antibakterielle Mittel
DE1793336C3 (de)	1974-10-03	D-Glucofuranoside, Verfahren zu deren Herstellung und diese enthaltende pharmazeutische Präparate
DE3132475C2 (cs)	1991-04-11
DE2404948C2 (de)	1983-04-14	7&alpha;-Acylthio-Steroidspirolactonderivate
DE3247175A1 (de)	1983-07-07	Dihydro- und tetrahydromonacolin l, ihre metallsalze und alkylester sowie verfahren zu ihrer herstellung und sie enthaltende arzneimittel
CH500971A (de)	1970-12-31	Verfahren zur Herstellung neuer Glucoside
DE1543890C3 (de)	1977-07-07	Neue 4'-Dimethyl-epipodophyIlotoxinß-Dglucosidderivate, deren Herstellung und diese enthaltende Heilmittel
DE2917890C2 (cs)	1987-10-29
CH507934A (de)	1971-05-31	Verfahren zur Herstellung eines neuen Glucosids
CH543502A (de)	1973-10-31	Verfahren zur Herstellung neuer Glucoside
EP0324390A2 (de)	1989-07-19	Nigericinderivate, Verfahren zu deren Herstellung, diese enthaltende Mittel und Verwendung derselben sowie die Verwendung von Nigericin als antiviral wirksame Substanz
DE68919057T2 (de)	1995-05-24	Lipophile Ether und/oder Ester von D-Desosamin, Verfahren zur Herstellung davon und ihre Verwendung als Fungizide und Bakterizide.
CH487144A (de)	1970-03-15	Verfahren zur Herstellung eines neuen Glucosides
AT216151B (de)	1961-07-10	Verfahren zur Herstellung von Deserpidinsäureestern
AT216152B (de)	1961-07-10	Verfahren zur Herstellung von Diestern der Deserpidinsäure und deren Salzen
AT253704B (de)	1967-04-25	Verfahren zur Herstellung des neuen 7α-Methyl-16α-hydroxy-östrons und seines 3, 16-Diacetates
DE3688364T2 (de)	1993-11-25	Steroidische Glycolipide als Immunstimulatoren.
AT253705B (de)	1967-04-25	Verfahren zur Herstellung von neuem 17α-Äthoxy-6-chlor-6-dehydro-progesteron
AT217645B (de)	1961-10-10	Verfahren zur Herstellung von neuen Derivaten des Aldosterons