SE8100471L - Forfarande for uppdelning av racemiska aglykoner - Google Patents

Forfarande for uppdelning av racemiska aglykoner

Info

Publication number
SE8100471L
SE8100471L SE8100471A SE8100471A SE8100471L SE 8100471 L SE8100471 L SE 8100471L SE 8100471 A SE8100471 A SE 8100471A SE 8100471 A SE8100471 A SE 8100471A SE 8100471 L SE8100471 L SE 8100471L
Authority
SE
Sweden
Prior art keywords
glycosides
general formula
racemic
ivb
division
Prior art date
Application number
SE8100471A
Other languages
English (en)
Other versions
SE447988B (sv
Inventor
F Arcamone
L Bernardi
B Patelli
S Penco
Original Assignee
Farmaceutici Italia
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.)
Filing date
Publication date
Application filed by Farmaceutici Italia filed Critical Farmaceutici Italia
Publication of SE8100471L publication Critical patent/SE8100471L/sv
Publication of SE447988B publication Critical patent/SE447988B/sv

Links

Classifications

    • 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
    • C07H15/252—Naphthacene radicals, e.g. daunomycins, adriamycins

Landscapes

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

Claims (3)

PATENT KRAV FOrfarande for uppdelning av racemlska aglykoner med den allmanna formeln II vent;
1. 113 Kr trate och RI och 113 Er like och Er metyl, metoxl, klor, eller brom;
2. R1 och 03 bade' Er %rate och 03 Er vate, metyl, metoxi, klor, oiler brom;
3. och 03 Kr vate och 03 Or en lagre alkoxigrupp med 1-4 kolatomer, kannetecknat darav, att dot omfatter kondenCation av en racemisk aglykon med strukturen II med 2,3,6-trldeoxl-3-trifluoroacetamidc 1-tr1fluoroac -a-L-lyxo-pyramosylklorid, van i RI, 02 och 03 definieras som tidigare och R4 Er en COCF3-grupp, av vilken blandning, often behandling i varm metanol fOr eliminering av den skyddande 0-trifluoroacetylgruppen i sockerdelen, de respekti, N-trifluoroacetylderivaten med de allmAnna formlerna IVb och Vb: IV)) VI) 011 COC11 "'3 On , \on,' C113/I 011 _ ett aprotiskt losningsmedel och i nArvaro av en katalysator av silvertrifluoro-metansulfonat (AgS03cF3), for framstAllning av en blandning av de skyddade (7S : 93)-a-glykosiderna (IVa) och (7R : 9R)-1-glykosiderna (Va): NI' Lo CI '3 erhilles corn en blandning och separation av denna sista blandning genom kronatografi pi silikakolonn med anvAndning av first kloroform och successivt en blandning av kloroform-aceton 95:5 (v/v) corn eluent fir 3lut114;t erhAllande av (7S : 9S)-a-glykosiderna med den allnInm formeln IVb och sedan, om sS onskas, separat framstAllning av 17R : 9R)-5-glykosiderna med den allmAnna formeln Vb, och direfter individuell behandling acetonlOsning av (7S , 9S)-a-glykosiderna med formal IVb eller (7R : 9R)-0-glykosiderna med formeln Vb med ett .vat syrahydrolyserande medal sisom 0,25 N NC1, fOr klyvning av glykosidbindningen och fOr slutligt erhAllande av de enantiomera (7S 1 9S)- och (7R : 9R)-aglykonerna. IVa
SE8100471A 1976-06-14 1981-01-26 Forfarande for uppdelning av racemiska aglykoner SE447988B (sv)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7617955A FR2355028A1 (fr) 1976-06-14 1976-06-14 Procede pour la preparation de glycosides derives d'anthracyclines optiquement actives

Publications (2)

Publication Number Publication Date
SE8100471L true SE8100471L (sv) 1981-01-26
SE447988B SE447988B (sv) 1987-01-12

Family

ID=9174331

Family Applications (2)

Application Number Title Priority Date Filing Date
SE7606808A SE421318B (sv) 1976-06-14 1976-06-15 Forfarande for framstellning av antracyklinglykosidor
SE8100471A SE447988B (sv) 1976-06-14 1981-01-26 Forfarande for uppdelning av racemiska aglykoner

Family Applications Before (1)

Application Number Title Priority Date Filing Date
SE7606808A SE421318B (sv) 1976-06-14 1976-06-15 Forfarande for framstellning av antracyklinglykosidor

Country Status (11)

Country Link
US (1) US4107423A (sv)
JP (1) JPS532463A (sv)
AT (2) AT345461B (sv)
BE (1) BE842930A (sv)
CA (1) CA1046510A (sv)
CH (1) CH622529A5 (sv)
DE (1) DE2626783C2 (sv)
FR (1) FR2355028A1 (sv)
GB (1) GB1509875A (sv)
NL (2) NL175300C (sv)
SE (2) SE421318B (sv)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1567456A (en) * 1976-11-16 1980-05-14 Farmaceutici Italia Daunomycin derivatives
IL55431A (en) * 1978-08-24 1982-07-30 Yeda Res & Dev Anthracycline type antibiotics,their preparation and pharmaceutical compositions comprising them
NL8001417A (nl) * 1979-03-17 1980-09-19 Erba Farmitalia Antitumorglycosiden.
GB2056443B (en) * 1979-08-20 1984-01-18 Hoffmann La Roche Cyclic compounds
JPS56135021A (en) * 1980-03-25 1981-10-22 Nippon Kokan Kk <Nkk> Lining for internal surface of welded part of steel pipe
CA1174669A (en) * 1980-07-18 1984-09-18 Michael J. Broadhurst Anthracycline glycosides
GB8317037D0 (en) * 1983-06-23 1983-07-27 Erba Farmitalia 6-deoxyanthracyclines
US4540695A (en) * 1981-08-12 1985-09-10 Sumitomo Chemical Co., Ltd. Aminonaphthacene derivatives and their use
NL8300150A (nl) * 1982-01-26 1983-08-16 Erba Farmitalia Daunorubicine en doxorubicine-analoga, hun bereiding en toepassing.
FI75834C (sv) * 1982-05-24 1988-08-08 Erba Farmitalia Förfarande för framställning av antracyklinglykosidföreningar
JPS59212499A (ja) * 1983-05-13 1984-12-01 アドリヤ・ラボラトリ−ズ・インコ−ポレ−テツド 抗腫瘍性抗生物質アントラサイクリンの４−デメトキシ−３′−デアミノ−３′（４−モリホリニル）誘導体
US4831019A (en) * 1983-10-31 1989-05-16 Adria Laboratories, Inc. Pharmaceutical preparations of 4-demethoxy-n-trifluoroacetyl anthracyclines
US4496485A (en) * 1983-11-25 1985-01-29 G. D. Searle & Co. Asymmetric 7-O-(substituted acetyl)-4-demethoxydaunomycinones
NZ224252A (en) * 1987-04-21 1991-09-25 Erba Carlo Spa An anthracycline glycoside and its preparation
GB8803301D0 (en) * 1988-02-12 1988-03-09 Erba Carlo Spa Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin
GB9418260D0 (en) * 1994-09-09 1994-10-26 Erba Carlo Spa Anthracycline derivatives
DE10155016A1 (de) * 2001-11-07 2003-05-15 Knoell Hans Forschung Ev Neue Chinon-Verbindung, Verfahren zur Herstellung und deren Verwendung
US8173621B2 (en) 2008-06-11 2012-05-08 Gilead Pharmasset Llc Nucleoside cyclicphosphates
CL2009002206A1 (es) 2008-12-23 2011-08-26 Gilead Pharmasset Llc Compuestos derivados de pirrolo -(2-3-d]-pirimidin-7(6h)-tetrahidrofuran-2-il fosfonamidato, composicion farmaceutica; y su uso en el tratamiento de enfermedades virales.
TW201026715A (en) * 2008-12-23 2010-07-16 Pharmasset Inc Nucleoside phosphoramidates
JP6104504B2 (ja) * 2008-12-23 2017-03-29 ギリアド ファーマセット エルエルシー ヌクレオシド類似体
CL2011000716A1 (es) 2010-03-31 2012-04-20 Gilead Pharmasset Llc Formas cristalinas 1 6 de (s)-isopropil-2-(((s)-(((2r.3r.4r.5r)-5-(2,4-dioxo-3,4-dihidropirimidin-1(2h)-il)-4-fluoro-3-hidroxi-4-metil tetrahidrofuran-2-il)metoxi)(fenoxi)fosforil)amino)propanoato; composicion y combinacion farmaceutica; y su uso para tratar una infeccion por el virus de la hepatitis c.
US8846882B2 (en) * 2011-04-29 2014-09-30 Synbias Pharma Ag Method of producing 4-demethoxydaunorubicin
CN104151376B (zh) * 2014-06-23 2017-02-08 天津药物研究院新药评价有限公司 一种抗肿瘤药物及其合成方法和用途

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3427300A (en) * 1965-11-12 1969-02-11 Merck & Co Inc Anti-inflammatory steroid 2'-acetamido-2'-deoxy-glucoside compounds
YU33730B (en) * 1967-04-18 1978-02-28 Farmaceutici Italia Process for preparing a novel antibiotic substance and salts thereof
US3803124A (en) * 1968-04-12 1974-04-09 Farmaceutici It Soc Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives
US3629231A (en) * 1968-05-23 1971-12-21 Biorex Laboratories Ltd Derivatives of glycyrrhetinic acid
FI51808C (sv) * 1968-07-15 1977-04-12 Rhone Poulenc Sa Förfarande för framställning av nya antitumorala naftacenderivat.
GB1467383A (en) * 1974-06-12 1977-03-16 Farmaceutici Italia Daunomycin analogues
US4039663A (en) * 1975-03-19 1977-08-02 Societa' Farmaceutici Italia S.P.A. Daunomycins, process for their uses and intermediates

Also Published As

Publication number Publication date
AT345461B (de) 1978-09-25
GB1509875A (en) 1978-05-04
SE7606808L (sv) 1977-12-16
FR2355028A1 (fr) 1978-01-13
ATA636377A (de) 1978-01-15
SE447988B (sv) 1987-01-12
CH622529A5 (en) 1981-04-15
NL7606897A (nl) 1977-12-28
CA1046510A (en) 1979-01-16
NL930090I2 (nl) 1994-03-16
US4107423A (en) 1978-08-15
NL930090I1 (nl) 1993-10-01
ATA450676A (de) 1977-12-15
FR2355028B3 (sv) 1979-03-02
DE2626783C2 (de) 1985-08-14
DE2626783A1 (de) 1977-12-29
JPS532463A (en) 1978-01-11
NL175300B (nl) 1984-05-16
BE842930A (fr) 1976-10-01
SE421318B (sv) 1981-12-14
NL175300C (nl) 1984-10-16
JPS6123200B2 (sv) 1986-06-04
AT344899B (de) 1978-08-10

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