CA1099706A - Derives aglycones de la daunomycinone - Google Patents

Derives aglycones de la daunomycinone

Info

Publication number: CA1099706A
Authority: CA; Canada
Prior art keywords: compound; formula; demethoxy; hydroxy; deoxy
Prior art date: 1977-05-05
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.): Expired

Application number

CA344,549A

Other languages

English (en)

Inventor

Paolo Masi

Luigi Bernardi

Antonino Suarato

Federico Arcamone

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Pfizer Italia SRL

Original Assignee

Farmaceutici Italia SpA

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.)

1977-05-05

Filing date

1980-01-28

Publication date

1981-04-21

1977-05-05 Priority claimed from GB18777/77A external-priority patent/GB1573037A/en

1980-01-28 Application filed by Farmaceutici Italia SpA filed Critical Farmaceutici Italia SpA

1980-01-28 Priority to CA344,549A priority Critical patent/CA1099706A/fr

1981-04-21 Application granted granted Critical

1981-04-21 Publication of CA1099706A publication Critical patent/CA1099706A/fr

Status Expired legal-status Critical Current

Links

YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical class C1[C@@](O)(C(C)=O)C[C@H](O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-MQJDWESPSA-N 0.000 title abstract description 5
TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 title description 3
PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 title description 3
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 42
238000000034 method Methods 0.000 claims abstract description 18
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 33
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 24
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 claims description 12
239000003960 organic solvent Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 8
239000011347 resin Substances 0.000 claims description 6
229920005989 resin Polymers 0.000 claims description 6
229910001923 silver oxide Inorganic materials 0.000 claims description 6
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 5
238000006243 chemical reaction Methods 0.000 claims description 5
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
-1 benzyl halide Chemical class 0.000 claims description 4
238000009835 boiling Methods 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910000027 potassium carbonate Inorganic materials 0.000 claims description 4
239000012736 aqueous medium Substances 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000000460 chlorine Substances 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
150000004820 halides Chemical class 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
230000003301 hydrolyzing effect Effects 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 3
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
239000000126 substance Substances 0.000 claims 4
230000036647 reaction Effects 0.000 claims 1
YOFDHOWPGULAQF-UHFFFAOYSA-N Daunomycin-Aglycone Natural products C1C(O)(C(C)=O)CC(O)C2=C1C(O)=C1C(=O)C(C=CC=C3OC)=C3C(=O)C1=C2O YOFDHOWPGULAQF-UHFFFAOYSA-N 0.000 abstract description 5
206010028980 Neoplasm Diseases 0.000 abstract description 3
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical class O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(O)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 STQGQHZAVUOBTE-VGBVRHCVSA-N 0.000 abstract description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 11
101150041968 CDC13 gene Proteins 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
125000003118 aryl group Chemical group 0.000 description 7
239000000243 solution Substances 0.000 description 7
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
229930182470 glycoside Natural products 0.000 description 5
150000002338 glycosides Chemical class 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
OAIVIYSBZFEOIU-UHFFFAOYSA-N chloroform;propan-2-one Chemical compound CC(C)=O.ClC(Cl)Cl OAIVIYSBZFEOIU-UHFFFAOYSA-N 0.000 description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
238000003756 stirring Methods 0.000 description 4
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
STQGQHZAVUOBTE-UHFFFAOYSA-N 7-Cyan-hept-2t-en-4,6-diinsaeure Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(C)=O)CC1OC1CC(N)C(O)C(C)O1 STQGQHZAVUOBTE-UHFFFAOYSA-N 0.000 description 2
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
FIWILGQIZHDAQG-UHFFFAOYSA-N NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F Chemical compound NC1=C(C(=O)NCC2=CC=C(C=C2)OCC(F)(F)F)C=C(C(=N1)N)N1N=C(N=C1)C1(CC1)C(F)(F)F FIWILGQIZHDAQG-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000002253 acid Substances 0.000 description 2
238000007792 addition Methods 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
239000012044 organic layer Substances 0.000 description 2
235000006408 oxalic acid Nutrition 0.000 description 2
UJDQUHYZDKYAAP-RWNSZTQCSA-N (7s,9s)-9-acetyl-7-[(2r,4s,5s,6s)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-9,11-dihydroxy-4,6-dimethoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O([C@H]1C[C@@](O)(CC=2C(O)=C3C(=O)C=4C=CC=C(C=4C(=O)C3=C(OC)C=21)OC)C(C)=O)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 UJDQUHYZDKYAAP-RWNSZTQCSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
RMZNXRYIFGTWPF-UHFFFAOYSA-N 2-nitrosoacetic acid Chemical compound OC(=O)CN=O RMZNXRYIFGTWPF-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 1
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
241000283986 Lepus Species 0.000 description 1
208000028018 Lymphocytic leukaemia Diseases 0.000 description 1
101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
235000018259 Solanum vestissimum Nutrition 0.000 description 1
240000002825 Solanum vestissimum Species 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
229940045799 anthracyclines and related substance Drugs 0.000 description 1
230000002927 anti-mitotic effect Effects 0.000 description 1
230000000259 anti-tumor effect Effects 0.000 description 1
FXCLIEYDXXVEAI-UHFFFAOYSA-N benzene;dichloromethane Chemical compound ClCCl.C1=CC=CC=C1 FXCLIEYDXXVEAI-UHFFFAOYSA-N 0.000 description 1
RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
125000001743 benzylic group Chemical group 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000005587 carbonate group Chemical group 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
WPJRFCZKZXBUNI-HCWXCVPCSA-N daunosamine Chemical class C[C@H](O)[C@@H](O)[C@@H](N)CC=O WPJRFCZKZXBUNI-HCWXCVPCSA-N 0.000 description 1
239000003814 drug Substances 0.000 description 1
238000011067 equilibration Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001914 filtration Methods 0.000 description 1
BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
208000003747 lymphoid leukemia Diseases 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000007017 scission Effects 0.000 description 1
229910052709 silver Inorganic materials 0.000 description 1
239000004332 silver Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
238000002054 transplantation Methods 0.000 description 1
125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
238000005406 washing Methods 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA344,549A 1977-05-05 1980-01-28 Derives aglycones de la daunomycinone Expired CA1099706A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA344,549A CA1099706A (fr)	1977-05-05	1980-01-28	Derives aglycones de la daunomycinone

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB18777/77		1977-05-05
GB18777/77A GB1573037A (en)	1977-05-05	1977-05-05	Anthracyclines
CA302,421A CA1099705A (fr)	1977-05-05	1978-05-02	Procede de preparation de nouveaux derives de la daunomycine et de leurs aglycones
CA344,549A CA1099706A (fr)	1977-05-05	1980-01-28	Derives aglycones de la daunomycinone

Publications (1)

Publication Number	Publication Date
CA1099706A true CA1099706A (fr)	1981-04-21

Family

ID=27165638

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA344,549A Expired CA1099706A (fr)	1977-05-05	1980-01-28	Derives aglycones de la daunomycinone

Country Status (1)

Country	Link
CA (1)	CA1099706A (fr)

1980
- 1980-01-28 CA CA344,549A patent/CA1099706A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1998-04-21	MKEX	Expiry

Publication	Publication Date	Title
CA1099705A (fr)	1981-04-21	Procede de preparation de nouveaux derives de la daunomycine et de leurs aglycones
CA1061335A (fr)	1979-08-28	Procede de preparation de glycosides oncolytiques
US4987126A (en)	1991-01-22	3'-deamino-4'-deoxy-4'-amino anthracyclines
CA1090787A (fr)	1980-12-02	Procede de preparation de derives de l'anthracycline
CA1046509A (fr)	1979-01-16	Mode de preparation des glycosides pour le traitement des tumeurs
EP0051280B1 (fr)	1984-07-11	Dérivés glycosidiques d'anthracyclines, méthode pour leur préparation, dérivés intermédiaires et leur préparation et compositions pharmaceutiques
CA1102792A (fr)	1981-06-09	Traduction non-disponible
GB2100257A (en)	1982-12-22	Anthracyclines
Brimble et al.	2001	C-Glycosylation of tri-O-benzyl-2-deoxy-D-glucose: synthesis of naphthyl-substituted 3, 6-dioxabicyclo [3.2. 2] nonanes
CA1090788A (fr)	1980-12-02	Procede de preparation de glycosides antitumeurs
CA1099706A (fr)	1981-04-21	Derives aglycones de la daunomycinone
SU1017173A3 (ru)	1983-05-07	Способ получени антрациклингликозидов
US4133877A (en)	1979-01-09	Anthracycline ethers and use therefor
CA1128503A (fr)	1982-07-27	Procede de preparation d'anthracyclines substituees antitumorales
JPS61227589A (ja)	1986-10-09	新規アントラサイクリングリコシド類，それらの製造方法及びそれらを含む抗腫瘍剤
CA1080703A (fr)	1980-07-01	Procede de preparation de nouveaux composes oncolytiques
US5719130A (en)	1998-02-17	Anthracycline derivative having a trifluoromethylated sugar
EP0014425B1 (fr)	1982-06-02	Anthracycline glycosides, méthodes pour leur préparation et compositions thérapeutiques les contenant
US4749693A (en)	1988-06-07	Nitro anthracyclines, process for their preparation and use thereof
CA1237714A (fr)	1988-06-07	Glycosides d'anthracycline
BE883759A (fr)	1980-10-01	Glycosides d'anthracycline
CA1091657A (fr)	1980-12-16	Nouvel agent anti-tumeur, hydrochlorure de 9- desacetyl-9 ethylene oxyde daunorubicine
US4134903A (en)	1979-01-16	Anthracycline ethers and their preparation
CA1046508A (fr)	1979-01-16	Synthese de la daunomycine et derives
DE3905431A1 (de)	1989-09-07	Neue 4-demethyl-4-0-(p-fluorobenzolsulfonyl)anthracyclinglycoside