CH514578A - Verfahren zur Herstellung von Glucosiden - Google Patents

Verfahren zur Herstellung von Glucosiden

Info

Publication number: CH514578A
Authority: CH; Switzerland
Prior art keywords: ethylidene; demethyl; epipodophyllotoxin; glucoside; benzyloxycarbonyl
Prior art date: 1968-02-27

Application number

CH284568A

Other languages

German (de)

English (en)

Inventor

Kuhn Max

Camilla Dr Keller-Juslen

Jany Dr Renz

Wartburg Albert Dr 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.)

1968-02-27

Filing date

1968-02-27

Publication date

1971-10-31

1968-02-27 Application filed by Sandoz Ag filed Critical Sandoz Ag

1968-02-27 Priority to CH284568A priority Critical patent/CH514578A/de

1969-01-31 Priority to NL6901619.A priority patent/NL166028C/xx

1969-02-06 Priority to DK64169AA priority patent/DK123715B/da

1969-02-06 Priority to FI690368A priority patent/FI48924C/fi

1969-02-25 Priority to AT188969A priority patent/AT303270B/de

1969-02-25 Priority to CA043,890A priority patent/CA956939A/en

1969-02-25 Priority to SU1832411A priority patent/SU447886A3/ru

1969-02-25 Priority to ES364043A priority patent/ES364043A1/es

1969-02-25 Priority to AT128571A priority patent/AT319971B/de

1969-02-25 Priority to SU1306929A priority patent/SU406346A3/ru

1969-02-25 Priority to CS132569A priority patent/CS153032B2/cs

1969-02-25 Priority to CS526269*A priority patent/CS153033B2/cs

1969-02-26 Priority to BR206655/69A priority patent/BR6906655D0/pt

1970-10-08 Priority to CH1489370A priority patent/CH518927A/de

1970-11-30 Priority to ES386032A priority patent/ES386032A1/es

1971-06-01 Priority to DK266771AA priority patent/DK128563B/da

1971-10-31 Publication of CH514578A publication Critical patent/CH514578A/de

1974-08-13 Priority to FI2397/74A priority patent/FI239774A7/fi

Links

238000000034 method Methods 0.000 title claims description 9
229930182478 glucoside Natural products 0.000 title claims description 6
150000008131 glucosides Chemical class 0.000 title description 3
238000004519 manufacturing process Methods 0.000 title description 2
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 24
150000001875 compounds Chemical class 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 18
239000003054 catalyst Substances 0.000 claims description 10
229910052763 palladium Inorganic materials 0.000 claims description 10
229960002246 beta-d-glucopyranose Drugs 0.000 claims description 8
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 8
238000002360 preparation method Methods 0.000 claims description 7
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 6
238000007327 hydrogenolysis reaction Methods 0.000 claims description 6
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 claims description 4
229910015900 BF3 Inorganic materials 0.000 claims description 4
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 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
XXCLTDOQUREFHZ-UHFFFAOYSA-L C(C)(=O)[O-].[Na+].C(C)(=O)[O-].[Zn+2] Chemical compound C(C)(=O)[O-].[Na+].C(C)(=O)[O-].[Zn+2] XXCLTDOQUREFHZ-UHFFFAOYSA-L 0.000 claims description 2
ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 claims description 2
125000000217 alkyl group Chemical group 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
239000004246 zinc acetate Substances 0.000 claims description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 44
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
238000003756 stirring Methods 0.000 description 8
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000012074 organic phase Substances 0.000 description 6
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
229910052938 sodium sulfate Inorganic materials 0.000 description 6
235000011152 sodium sulphate Nutrition 0.000 description 6
238000001816 cooling Methods 0.000 description 5
238000002425 crystallisation Methods 0.000 description 5
230000008025 crystallization Effects 0.000 description 5
238000001035 drying Methods 0.000 description 5
230000007717 exclusion Effects 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 5
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
239000002904 solvent Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 3
239000013078 crystal Substances 0.000 description 3
239000000155 melt Substances 0.000 description 3
229910052751 metal Inorganic materials 0.000 description 3
239000002184 metal Substances 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000007858 starting material Substances 0.000 description 3
VZPBLPQAMPVTFO-DBVAJOADSA-N (4ar,7r,8r,8as)-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol Chemical compound O1C(O)[C@H](O)[C@@H](O)[C@@H]2OC(C)OC[C@H]21 VZPBLPQAMPVTFO-DBVAJOADSA-N 0.000 description 2
SWWQQSDRUYSMAR-UHFFFAOYSA-N 1-[(4-hydroxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;hydrochloride Chemical group Cl.C1=CC(O)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 SWWQQSDRUYSMAR-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical class COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 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
-1 aliphatic aldehyde Chemical class 0.000 description 2
229940057499 anhydrous zinc acetate Drugs 0.000 description 2
TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
239000003814 drug Substances 0.000 description 2
HWJHWSBFPPPIPD-UHFFFAOYSA-N ethoxyethane;propan-2-one Chemical compound CC(C)=O.CCOCC HWJHWSBFPPPIPD-UHFFFAOYSA-N 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
238000010792 warming 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
YJGVMLPVUAXIQN-LGWHJFRWSA-N (5s,5ar,8ar,9r)-5-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one Chemical compound COC1=C(OC)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3[C@@H](O)[C@@H]3[C@@H]2C(OC3)=O)=C1 YJGVMLPVUAXIQN-LGWHJFRWSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
229910052684 Cerium Inorganic materials 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
208000007093 Leukemia L1210 Diseases 0.000 description 1
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
208000037273 Pathologic Processes Diseases 0.000 description 1
101150003085 Pdcl gene Proteins 0.000 description 1
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
239000008346 aqueous phase Substances 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
201000011510 cancer Diseases 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000004663 cell proliferation Effects 0.000 description 1
GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
WGXZDYPGLJYBJW-UHFFFAOYSA-N chloroform;propan-2-ol Chemical compound CC(C)O.ClC(Cl)Cl WGXZDYPGLJYBJW-UHFFFAOYSA-N 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
230000001085 cytostatic effect Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
YJGVMLPVUAXIQN-UHFFFAOYSA-N epipodophyllotoxin Natural products COC1=C(OC)C(OC)=CC(C2C3=CC=4OCOC=4C=C3C(O)C3C2C(OC3)=O)=C1 YJGVMLPVUAXIQN-UHFFFAOYSA-N 0.000 description 1
PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
NBEMQPLNBYYUAZ-UHFFFAOYSA-N ethyl acetate;propan-2-one Chemical compound CC(C)=O.CCOC(C)=O NBEMQPLNBYYUAZ-UHFFFAOYSA-N 0.000 description 1
210000002950 fibroblast Anatomy 0.000 description 1
238000001914 filtration Methods 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
229960001031 glucose Drugs 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
201000006512 mast cell neoplasm Diseases 0.000 description 1
208000006971 mastocytoma Diseases 0.000 description 1
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
230000009054 pathological process Effects 0.000 description 1
FDJABJJEKWDNQO-UHFFFAOYSA-N pentane;propan-2-one Chemical compound CC(C)=O.CCCCC FDJABJJEKWDNQO-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
230000007017 scission Effects 0.000 description 1
239000013049 sediment Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
238000005406 washing Methods 0.000 description 1
229960000314 zinc acetate Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/54—Preparation of carboxylic acid anhydrides
- C07C51/56—Preparation of carboxylic acid anhydrides from organic acids, their salts, their esters or their halides, e.g. by carboxylation
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/12—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by acids having the group -X-C(=X)-X-, or halides thereof, in which each X means nitrogen, oxygen, sulfur, selenium or tellurium, e.g. carbonic acid, carbamic acid
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Oil, Petroleum & Natural Gas (AREA)
Saccharide Compounds (AREA)

CH284568A 1968-02-27 1968-02-27 Verfahren zur Herstellung von Glucosiden CH514578A (de)

Priority Applications (17)

Application Number	Priority Date	Filing Date	Title
CH284568A CH514578A (de)	1968-02-27	1968-02-27	Verfahren zur Herstellung von Glucosiden
NL6901619.A NL166028C (nl)	1968-02-27	1969-01-31	Werkwijze voor het bereiden van een 4'-demethylepipodo- -fyllotoxine-beta-d-glucoside en werkwijze voor het bereiden van een farmaceutisch preparaat ter bestrij- ding van pathologische processen die met celvermeerde- ring gepaard gaan en gevormd preparaat verkregen onder toepassing van laatstgenoemde werkwijze.
DK64169AA DK123715B (da)	1968-02-27	1969-02-06	Fremgangsmåde til fremstilling af 4'-demethylepipodophyllotoxin-β-D-alkylidenglucosider.
FI690368A FI48924C (fi)	1968-02-27	1969-02-06	Menetelmä terapeuttisesti käytettävien 4'-demetyyli-epipodofyllotoksii nin glukosidien valmistamiseksi.
ES364043A ES364043A1 (es)	1968-02-27	1969-02-25	Procedimiento para la obtencion de derivados glucosidos.
CS526269*A CS153033B2 (cs)	1968-02-27	1969-02-25
SU1832411A SU447886A3 (ru)	1968-02-27	1969-02-25	Способ получения защищенной 4,6-0-алкилиден- - -глюкопиранозы
AT188969A AT303270B (de)	1968-02-27	1969-02-25	Verfahren zur Herstellung von neuen Glucosiden
AT128571A AT319971B (de)	1968-02-27	1969-02-25	Verfahren zur Herstellung neuer geschützter 4,6-O-Alkyliden-Β-D-glucopyranosen
SU1306929A SU406346A3 (cs)	1968-02-27	1969-02-25
CS132569A CS153032B2 (cs)	1968-02-27	1969-02-25
CA043,890A CA956939A (en)	1968-02-27	1969-02-25	Epipodophyllotoxin compounds
BR206655/69A BR6906655D0 (pt)	1968-02-27	1969-02-26	Processo de fabricacao de glicosidios
CH1489370A CH518927A (de)	1968-02-27	1970-10-08	Verfahren zur Herstellung von geschützter 4,6-O-Alkyliden-B-D-glucopyranose
ES386032A ES386032A1 (es)	1968-02-27	1970-11-30	Procedimiento para la obtencion de derivados de 4,6-o-al- quilideno-glucopiranosa.
DK266771AA DK128563B (da)	1968-02-27	1971-06-01	4,6-0-Alkyliden-β-D-glucopyranoser til anvendelse som mellemprodukter ved fremstilling af terapeutisk værdifulde 4'-demethylepipodophyllotoxin-β-D-alkylidenglucosider og fremgangsmåde til fremstilling deraf.
FI2397/74A FI239774A7 (cs)	1968-02-27	1974-08-13

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH284568A CH514578A (de)	1968-02-27	1968-02-27	Verfahren zur Herstellung von Glucosiden

Publications (1)

Publication Number	Publication Date
CH514578A true CH514578A (de)	1971-10-31

Family

ID=4242875

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH284568A CH514578A (de)	1968-02-27	1968-02-27	Verfahren zur Herstellung von Glucosiden
CH1489370A CH518927A (de)	1968-02-27	1970-10-08	Verfahren zur Herstellung von geschützter 4,6-O-Alkyliden-B-D-glucopyranose

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1489370A CH518927A (de)	1968-02-27	1970-10-08	Verfahren zur Herstellung von geschützter 4,6-O-Alkyliden-B-D-glucopyranose

Country Status (9)

Country	Link
AT (2)	AT319971B (cs)
BR (1)	BR6906655D0 (cs)
CA (1)	CA956939A (cs)
CH (2)	CH514578A (cs)
CS (2)	CS153033B2 (cs)
DK (2)	DK123715B (cs)
FI (1)	FI48924C (cs)
NL (1)	NL166028C (cs)
SU (2)	SU447886A3 (cs)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0111058A1 (en) *	1982-11-26	1984-06-20	Nippon Kayaku Kabushiki Kaisha	Process for producing 4'-demethyl-epipodophyllotoxin-beta-D-ethylidene-glucoside and acyl-derivative thereof
DE3826562A1 (de) *	1987-08-04	1989-02-16	Bristol Myers Co	Epipodophyllotoxinglucosid-4' -phosphat-derivate
EP0226202A3 (en) *	1985-12-16	1989-04-05	Bar-Ilan University	Synthesis of podophylotoxin type compounds
AU583585B2 (en) *	1985-02-19	1989-05-04	Nippon Kayaku Kabushiki Kaisha	Etoposide preparations
EP0401800A3 (en) *	1989-06-07	1991-04-10	Bristol-Myers Squibb Company	Acylated derivatives of etoposide
WO2017157825A1 (en)	2016-03-15	2017-09-21	F. Hoffmann-La Roche Ag	Combinations of lsd1 inhibitors for use in the treatment of solid tumors

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4935504A (en) *	1987-12-18	1990-06-19	Bristol-Myers Company	Epipodophyllotoxin glucoside 4'-acyl derivatives
US5066645A (en) *	1989-09-01	1991-11-19	Bristol-Myers Company	Epipodophyllotoxin altroside derivatives
US5463040A (en) *	1994-06-28	1995-10-31	Teva Pharmaceutical Industries, Ltd.	Method of preparing etoposide
US8173621B2 (en)	2008-06-11	2012-05-08	Gilead Pharmasset Llc	Nucleoside cyclicphosphates
EP2376515A1 (en)	2008-12-23	2011-10-19	Pharmasset, Inc.	Synthesis of purine nucleosides
CA2748057C (en)	2008-12-23	2018-07-03	Pharmasset, Inc.	Nucleoside phosphoramidates

1968
- 1968-02-27 CH CH284568A patent/CH514578A/de not_active IP Right Cessation
1969
- 1969-01-31 NL NL6901619.A patent/NL166028C/xx not_active IP Right Cessation
- 1969-02-06 DK DK64169AA patent/DK123715B/da not_active IP Right Cessation
- 1969-02-06 FI FI690368A patent/FI48924C/fi active
- 1969-02-25 SU SU1832411A patent/SU447886A3/ru active
- 1969-02-25 CS CS526269*A patent/CS153033B2/cs unknown
- 1969-02-25 CS CS132569A patent/CS153032B2/cs unknown
- 1969-02-25 CA CA043,890A patent/CA956939A/en not_active Expired
- 1969-02-25 AT AT128571A patent/AT319971B/de not_active IP Right Cessation
- 1969-02-25 AT AT188969A patent/AT303270B/de not_active IP Right Cessation
- 1969-02-25 SU SU1306929A patent/SU406346A3/ru active
- 1969-02-26 BR BR206655/69A patent/BR6906655D0/pt unknown
1970
- 1970-10-08 CH CH1489370A patent/CH518927A/de not_active IP Right Cessation
1971
- 1971-06-01 DK DK266771AA patent/DK128563B/da not_active IP Right Cessation

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0111058A1 (en) *	1982-11-26	1984-06-20	Nippon Kayaku Kabushiki Kaisha	Process for producing 4'-demethyl-epipodophyllotoxin-beta-D-ethylidene-glucoside and acyl-derivative thereof
AU583585B2 (en) *	1985-02-19	1989-05-04	Nippon Kayaku Kabushiki Kaisha	Etoposide preparations
EP0226202A3 (en) *	1985-12-16	1989-04-05	Bar-Ilan University	Synthesis of podophylotoxin type compounds
DE3826562A1 (de) *	1987-08-04	1989-02-16	Bristol Myers Co	Epipodophyllotoxinglucosid-4' -phosphat-derivate
USRE35524E (en) *	1987-08-04	1997-06-03	Bristol-Myers Squibb Company	Epipodophyllotoxin glucoside 4'-phosphate derivatives
EP0401800A3 (en) *	1989-06-07	1991-04-10	Bristol-Myers Squibb Company	Acylated derivatives of etoposide
WO2017157825A1 (en)	2016-03-15	2017-09-21	F. Hoffmann-La Roche Ag	Combinations of lsd1 inhibitors for use in the treatment of solid tumors
US10265279B2 (en)	2016-03-15	2019-04-23	Oryzon Genomics, S.A.	Combinations of LSD1 inhibitors for use in the treatment of solid tumors
EP4684836A2 (en)	2016-03-15	2026-01-28	Oryzon Genomics, S.A.	Combinations of lsd1 inhibitors for use in the treatment of neoplastic diseases
US12564559B2 (en)	2016-03-15	2026-03-03	Oryzon Genomics, S.A.	Combinations of LSD1 inhibitors for use in the treatment of solid tumors

Also Published As

Publication number	Publication date
DK128563B (da)	1974-05-27
CS153032B2 (cs)	1974-02-22
NL6901619A (cs)	1969-08-29
BR6906655D0 (pt)	1973-01-09
CS153033B2 (cs)	1974-02-22
AT303270B (de)	1972-11-27
NL166028C (nl)	1981-06-15
CH518927A (de)	1972-02-15
SU447886A3 (ru)	1974-10-25
AT319971B (de)	1975-01-27
SU406346A3 (cs)	1973-11-05
FI48924B (cs)	1974-10-31
DK123715B (da)	1972-07-24
CA956939A (en)	1974-10-29
NL166028B (nl)	1981-01-15
FI48924C (fi)	1975-02-10

Legal Events

Date	Code	Title	Description
1988-04-29	PL	Patent ceased

Publication	Publication Date	Title
DE2642837C3 (de)	1982-08-12	Anthracyclinglycoside und Verfahren zu deren Herstellung
DE2844292A1 (de)	1979-06-28	Pyrrolobenzodiazepine, verfahren zu ihrer herstellung und ihre verwendung zur behandlung von tumorerkrankungen
CH514578A (de)	1971-10-31	Verfahren zur Herstellung von Glucosiden
DE2824905A1 (de)	1979-01-04	Neue 1, 2, 3, 4, 6, 7-hexahydro-11 balphah-benzo(a)chinolizin-derivate und verfahren zur herstellung derselben
DE1795543C3 (de)	1980-06-04	Indolyl-(3)-alkancarbonsaure-niedrig alkylester
CH544752A (de)	1974-01-15	Verfahren zur Herstellung neuer Glucoside
DE1274100B (de)	1968-08-01	Verfahren zur Herstellung von 1, 6-Dibrom-1, 6-didesoxydulcit
DE2952385A1 (de)	1980-07-10	Verfahren zur herstellung von 7-chlor- 2-methyl-3,3a-dihydro-2h,9h-isoxazol (3,2-b) (1,3)-benzoxazin-9-on
DE2217965C3 (de)	1974-07-25	2alpha-Methyl-17 beta-cyclopentyloxy -5 alpha-androstan-3-on, Verfahren zu seiner Herstellung sowie dieses enthaltendes Mittel
DE1695094A1 (de)	1970-12-10	Verfahren zur Herstellung von neuen N-Heterocyclen
AT253705B (de)	1967-04-25	Verfahren zur Herstellung von neuem 17α-Äthoxy-6-chlor-6-dehydro-progesteron
AT238888B (de)	1965-03-10	Verfahren zur Herstellung von neuen, in 16-Stellung durch eine Methylgruppe substituierten 3α-Hydroxy-11,20-dioxo-21-pregnanglyoxylsäuren
DE2256912C2 (de)	1984-04-05	Digoxigenin-3-[2',3'-didesoxy-glykoside], Verfahren zu ihrer Herstellung und deren Verwendung
CH507934A (de)	1971-05-31	Verfahren zur Herstellung eines neuen Glucosids
CH526527A (de)	1972-08-15	Verfahren zur Herstellung eines neuen 6a-Methyl-19-nor-progesterons
DE1620621C3 (de)	1975-05-22	Verfahren zur selektiven Chlorierung und Bromierung von Methyl-6,8-dideoxy-1-thio-D-erythro-(und L-threo)alpha-D-galacto-octopyranosid-Derivaten und deren Homologen zu den entsprechenden 7-Chlor- und -Brom-Derivaten
CH589668A5 (en)	1977-07-15	Cytostatic (4')-demethyl substd. epipodophyllotoxin - prepd. from the corresp. glucopyranoside with (3)-thiophene-carboxaldehyde
CH543502A (de)	1973-10-31	Verfahren zur Herstellung neuer Glucoside
AT253704B (de)	1967-04-25	Verfahren zur Herstellung des neuen 7α-Methyl-16α-hydroxy-östrons und seines 3, 16-Diacetates
CH525880A (de)	1972-07-31	Verfahren zur Herstellung eines neuen Glucosids
AT252241B (de)	1967-02-10	Verfahren zur Herstellung von neuen 4-Aryl-isoflavanoiden
AT263229B (de)	1968-07-10	Verfahren zur Herstellung neuer 3-OR-11-Oxo-16-androstene
AT241707B (de)	1965-08-10	Verfahren zur Herstellung neuer Oestradiolderivate
AT283607B (de)	1970-08-10	Verfahren zur Herstellung von neuen Desoxyribofuranosylderivaten
DE1943901A1 (de)	1971-05-19	Cardenolid-3-[2',3'-didesoxyglykoside] und Verfahren zu ihrer Herstellung