CA1197237A - Daunorubicin and doxorubicin analogues, their preparation and use thereof - Google Patents

Daunorubicin and doxorubicin analogues, their preparation and use thereof

Info

Publication number: CA1197237A
Authority: CA; Canada
Prior art keywords: methyl; demethoxy; daunorubicin; doxorubicin; dimethyl
Prior art date: 1982-01-26
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

CA000419718A

Other languages

English (en)

French (fr)

Inventor

Federico Arcamone

Giuliano Franchi

Sergio Penco

Anna M. Casazza

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

Farmitalia Carlo Erba SRL

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.)

1982-01-26

Filing date

1983-01-18

Publication date

1985-11-26

1983-01-18 Application filed by Farmitalia Carlo Erba SRL filed Critical Farmitalia Carlo Erba SRL

1985-11-26 Application granted granted Critical

1985-11-26 Publication of CA1197237A publication Critical patent/CA1197237A/en

Status Expired legal-status Critical Current

Links

AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin 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(=O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 title claims description 96
229960000975 daunorubicin Drugs 0.000 title claims description 12
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 title claims description 9
STQGQHZAVUOBTE-VGBVRHCVSA-N daunorubicin Chemical compound 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 title claims description 9
150000001875 compounds Chemical class 0.000 claims abstract description 31
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
239000001257 hydrogen Substances 0.000 claims abstract description 11
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
229940045799 anthracyclines and related substance Drugs 0.000 claims abstract description 6
229930182470 glycoside Natural products 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
229960004679 doxorubicin Drugs 0.000 claims description 52
238000000034 method Methods 0.000 claims description 21
230000008569 process Effects 0.000 claims description 19
238000011282 treatment Methods 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
ZUFQFGSMHXKORU-UHFFFAOYSA-N 9-acetyl-6,7,9,11-tetrahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C(=O)C2=C1C(O)=C1C(O)CC(C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-UHFFFAOYSA-N 0.000 claims description 4
CQXYIKPCIOTYHD-UHFFFAOYSA-N 7-(4-amino-5-methoxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O1C(C)C(OC)C(N)CC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(=O)CO)C1 CQXYIKPCIOTYHD-UHFFFAOYSA-N 0.000 claims description 3
239000004280 Sodium formate Substances 0.000 claims description 3
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 3
235000019254 sodium formate Nutrition 0.000 claims description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 2
230000031709 bromination Effects 0.000 claims description 2
238000005893 bromination reaction Methods 0.000 claims description 2
239000000126 substance Substances 0.000 claims 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 2
-1 glycoside com-pounds Chemical class 0.000 claims 2
239000000543 intermediate Substances 0.000 claims 1
239000002808 molecular sieve Substances 0.000 claims 1
QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims 1
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 10
150000002338 glycosides Chemical class 0.000 abstract description 3
241000699670 Mus sp. Species 0.000 description 28
208000032839 leukemia Diseases 0.000 description 21
206010028980 Neoplasm Diseases 0.000 description 19
210000004027 cell Anatomy 0.000 description 17
230000000694 effects Effects 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
210000001072 colon Anatomy 0.000 description 7
231100000331 toxic Toxicity 0.000 description 7
230000002588 toxic effect Effects 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000003389 potentiating effect Effects 0.000 description 6
230000004614 tumor growth Effects 0.000 description 6
201000009030 Carcinoma Diseases 0.000 description 5
230000034994 death Effects 0.000 description 5
231100000517 death Toxicity 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
238000011081 inoculation Methods 0.000 description 5
230000004083 survival effect Effects 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010048610 Cardiotoxicity Diseases 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
231100000259 cardiotoxicity Toxicity 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
238000000338 in vitro Methods 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000003902 lesion Effects 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
230000009885 systemic effect Effects 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
XDXDZDZNSLXDNA-TZNDIEGXSA-N Idarubicin Chemical compound C1[C@H](N)[C@H](O)[C@H](C)O[C@H]1O[C@@H]1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2C[C@@](O)(C(C)=O)C1 XDXDZDZNSLXDNA-TZNDIEGXSA-N 0.000 description 2
XDXDZDZNSLXDNA-UHFFFAOYSA-N Idarubicin Natural products C1C(N)C(O)C(C)OC1OC1C2=C(O)C(C(=O)C3=CC=CC=C3C3=O)=C3C(O)=C2CC(O)(C(C)=O)C1 XDXDZDZNSLXDNA-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
230000007681 cardiovascular toxicity Effects 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
229940125890 compound Ia Drugs 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
231100000433 cytotoxic Toxicity 0.000 description 2
230000001472 cytotoxic effect Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000004907 flux Effects 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229960000908 idarubicin Drugs 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000002054 inoculum Substances 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
239000000203 mixture Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
230000009467 reduction Effects 0.000 description 2
239000000243 solution Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000012360 testing method Methods 0.000 description 2
210000004881 tumor cell Anatomy 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 1
SDWZXVTWORCAMD-MVGXARHUSA-N 2-[[3-hydroxy-2-methyl-6-[[(1s,3s)-3,5,12-trihydroxy-3-(2-hydroxyacetyl)-10-methoxy-6,11-dioxo-2,4-dihydro-1h-tetracen-1-yl]oxy]oxan-4-yl]amino]acetonitrile Chemical compound 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(=O)CO)C1CC(NCC#N)C(O)C(C)O1 SDWZXVTWORCAMD-MVGXARHUSA-N 0.000 description 1
238000011725 BALB/c mouse Methods 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
238000011735 C3H mouse Methods 0.000 description 1
101800000021 N-terminal protease Proteins 0.000 description 1
101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
238000007792 addition Methods 0.000 description 1
208000009956 adenocarcinoma Diseases 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000010171 animal model Methods 0.000 description 1
210000003567 ascitic fluid Anatomy 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
231100001012 cardiac lesion Toxicity 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
208000029742 colonic neoplasm Diseases 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000007774 longterm Effects 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 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
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
QGVNJRROSLYGKF-UHFFFAOYSA-N thiobarbital Chemical compound CCC1(CC)C(=O)NC(=S)NC1=O QGVNJRROSLYGKF-UHFFFAOYSA-N 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000005748 tumor development Effects 0.000 description 1

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
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
- 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)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Genetics & Genomics (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
Oncology (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

CA000419718A 1982-01-26 1983-01-18 Daunorubicin and doxorubicin analogues, their preparation and use thereof Expired CA1197237A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8202080		1982-01-26
GB8202080		1982-01-26

Publications (1)

Publication Number	Publication Date
CA1197237A true CA1197237A (en)	1985-11-26

Family

ID=10527864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000419718A Expired CA1197237A (en)	1982-01-26	1983-01-18	Daunorubicin and doxorubicin analogues, their preparation and use thereof

Country Status (28)

Country	Link
JP (1)	JPS58128396A (ru)
KR (1)	KR900006214B1 (ru)
AT (1)	AT378776B (ru)
AU (1)	AU551700B2 (ru)
BE (1)	BE895687A (ru)
CA (1)	CA1197237A (ru)
CH (1)	CH657622A5 (ru)
CS (1)	CS235979B2 (ru)
DE (1)	DE3301489A1 (ru)
DK (1)	DK157322C (ru)
ES (1)	ES8403140A1 (ru)
FI (1)	FI74977C (ru)
FR (1)	FR2520365B1 (ru)
GB (1)	GB2116169B (ru)
GR (1)	GR77890B (ru)
HU (1)	HU192784B (ru)
IE (1)	IE53750B1 (ru)
IL (1)	IL67709A (ru)
IT (1)	IT1210482B (ru)
NL (1)	NL8300150A (ru)
NO (1)	NO153456C (ru)
NZ (1)	NZ203047A (ru)
PH (1)	PH19130A (ru)
PT (1)	PT76113A (ru)
SE (1)	SE461591B (ru)
SU (1)	SU1187724A3 (ru)
YU (1)	YU43536B (ru)
ZA (1)	ZA83450B (ru)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB2182926B (en) *	1985-11-19	1989-10-04	Erba Farmitalia	Nitro anthracyclines, process for their preparation and use thereof
GB8708927D0 (en) *	1987-04-14	1987-05-20	Erba Farmitalia	Chiral synthesis of anthracyclines

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1509875A (en) *	1976-06-14	1978-05-04	Farmaceutici Italia	Optically active anthracyclinones and anthracycline glycosides
GB1573037A (en) *	1977-05-05	1980-08-13	Farmaceutici Italia	Anthracyclines
ATE4387T1 (de) *	1979-07-04	1983-08-15	Farmitalia Carlo Erba S.P.A.	Anthracyclin-glycoside, verfahren zu ihrer herstellung und sie enthaltende therapeutische zusammensetzung.
DE3100968A1 (de) *	1980-01-16	1982-01-14	Farmitalia Carlo Erba S.p.A., 20159 Milano	Anthracyclinderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel

1983
- 1983-01-14 NL NL8300150A patent/NL8300150A/nl not_active Application Discontinuation
- 1983-01-17 AU AU10525/83A patent/AU551700B2/en not_active Ceased
- 1983-01-17 GB GB08301178A patent/GB2116169B/en not_active Expired
- 1983-01-17 YU YU89/83A patent/YU43536B/xx unknown
- 1983-01-17 FI FI830155A patent/FI74977C/fi not_active IP Right Cessation
- 1983-01-18 CA CA000419718A patent/CA1197237A/en not_active Expired
- 1983-01-18 NZ NZ203047A patent/NZ203047A/en unknown
- 1983-01-18 IT IT8319147A patent/IT1210482B/it active
- 1983-01-18 AT AT0015683A patent/AT378776B/de not_active IP Right Cessation
- 1983-01-18 DE DE19833301489 patent/DE3301489A1/de active Granted
- 1983-01-18 IL IL67709A patent/IL67709A/xx unknown
- 1983-01-19 PT PT76113A patent/PT76113A/pt unknown
- 1983-01-19 PH PH28401A patent/PH19130A/en unknown
- 1983-01-19 CS CS83374A patent/CS235979B2/cs unknown
- 1983-01-19 JP JP58005974A patent/JPS58128396A/ja active Granted
- 1983-01-20 CH CH317/83A patent/CH657622A5/it not_active IP Right Cessation
- 1983-01-21 SE SE8300324A patent/SE461591B/sv not_active IP Right Cessation
- 1983-01-24 GR GR70317A patent/GR77890B/el unknown
- 1983-01-24 BE BE0/209955A patent/BE895687A/fr unknown
- 1983-01-24 SU SU833542550A patent/SU1187724A3/ru active
- 1983-01-24 ZA ZA83450A patent/ZA83450B/xx unknown
- 1983-01-25 ES ES519255A patent/ES8403140A1/es not_active Expired
- 1983-01-25 FR FR8301078A patent/FR2520365B1/fr not_active Expired
- 1983-01-25 DK DK027683A patent/DK157322C/da not_active IP Right Cessation
- 1983-01-25 HU HU83240A patent/HU192784B/hu not_active IP Right Cessation
- 1983-01-25 KR KR1019830000279A patent/KR900006214B1/ko active IP Right Grant
- 1983-01-25 IE IE144/83A patent/IE53750B1/en unknown
- 1983-01-25 NO NO830234A patent/NO153456C/no unknown

Also Published As

Publication number	Publication date
IE53750B1 (en)	1989-02-01
ES519255A0 (es)	1984-03-01
AT378776B (de)	1985-09-25
NZ203047A (en)	1985-10-11
KR900006214B1 (ko)	1990-08-25
KR840003262A (ko)	1984-08-20
SE8300324D0 (sv)	1983-01-21
GB8301178D0 (en)	1983-02-16
NO153456B (no)	1985-12-16
DK27683A (da)	1983-07-27
FI74977B (fi)	1987-12-31
FR2520365B1 (fr)	1985-07-12
AU551700B2 (en)	1986-05-08
CH657622A5 (it)	1986-09-15
FI830155A0 (fi)	1983-01-17
GB2116169A (en)	1983-09-21
IL67709A0 (en)	1983-05-15
JPS58128396A (ja)	1983-07-30
SU1187724A3 (ru)	1985-10-23
IT8319147A0 (it)	1983-01-18
DK157322C (da)	1990-05-07
FR2520365A1 (fr)	1983-07-29
FI74977C (fi)	1988-04-11
IE830144L (en)	1983-07-26
IL67709A (en)	1986-03-31
ES8403140A1 (es)	1984-03-01
PH19130A (en)	1986-01-08
ZA83450B (en)	1983-10-26
SE461591B (sv)	1990-03-05
PT76113A (en)	1983-02-01
YU8983A (en)	1986-02-28
FI830155L (fi)	1983-07-27
ATA15683A (de)	1985-02-15
NO153456C (no)	1986-03-26
YU43536B (en)	1989-08-31
CS235979B2 (en)	1985-05-15
GR77890B (ru)	1984-09-25
BE895687A (fr)	1983-05-16
NL8300150A (nl)	1983-08-16
SE8300324L (sv)	1983-07-27
NO830234L (no)	1983-07-27
DE3301489A1 (de)	1983-08-04
HU192784B (en)	1987-07-28
DK27683D0 (da)	1983-01-25
AU1052583A (en)	1983-08-04
DE3301489C2 (ru)	1988-01-28
GB2116169B (en)	1985-09-04
JPS6328436B2 (ru)	1988-06-08
DK157322B (da)	1989-12-11
IT1210482B (it)	1989-09-14

Publication	Publication Date	Title
CA1099705A (en)	1981-04-21	Process for the preparation of new daunomycin derivatives and their aglycones
KR870000656B1 (ko)	1987-04-04	N-[4-(3-아미노프로필)-아미노부틸]-2-(ω-구아니디노-지방산-아미도)-2-치환된-에탄아미드 및 이들 염의 제조방법
US4987126A (en)	1991-01-22	3'-deamino-4'-deoxy-4'-amino anthracyclines
EP0051280B1 (en)	1984-07-11	Anthracycline glycosides, process for the preparation thereof, intermediate compounds and their preparation and pharmaceutical compositions
AU610665B2 (en)	1991-05-23	New 2-(piperazinyl)-2-substituted flavonoid derivatives, processes for preparing them and pharmaceutical compositions containing them
CA1197237A (en)	1985-11-26	Daunorubicin and doxorubicin analogues, their preparation and use thereof
US4430346A (en)	1984-02-07	Novel carcinostatic substance and process for synthesis thereof
EP0199920A1 (en)	1986-11-05	New antitumor anthracyclines
EP0022515B1 (en)	1983-08-03	Anthracycline glycosides, process for their preparation and therapeutical composition containing them
FI78109B (fi)	1989-02-28	Foerfarande foer framstaellning av antracyklinglykosider.
US4131649A (en)	1978-12-26	Daunorubicin derivatives, their preparation and their use
RU2073681C1 (ru)	1997-02-20	Антрациклиновый гликозид и способы его получения
AU658728B2 (en)	1995-04-27	N-methyldeacetylcolchiceinamide derivatives
GB1561507A (en)	1980-02-20	Snthracycline disaccharides
RU2065863C1 (ru)	1996-08-27	Производные дезацетилколхицина, способ их получения и противоопухолевая композиция
BE883759A (fr)	1980-10-01	Glycosides d'anthracycline
CA1237714A (en)	1988-06-07	Anthracycline glycosides
US5753695A (en)	1998-05-19	Flavilium compounds and method of using
GB2034707A (en)	1980-06-11	Anthracycline glycosides
IT9022047A1 (it)	1992-05-14	13-desosso-4'-desossi-4'-iodoantracicline
GB2247885A (en)	1992-03-18	13-dihydro-3'-(2-alkoxy-4-morpholinyl)anthracyclines
GB2047242A (en)	1980-11-26	3'4'-diepi-4'-o-methyl derivatives of daunorubicin and doxorubicin
CA1095028A (en)	1981-02-03	Anthracyclines
Artico et al.	1968	Aryl-2-halogenoalkylamines—XXII. Derivatives of phenoxyacetic acid: Synthesis and antineoplastic activities
WO1990007519A1 (en)	1990-07-12	3'-deamino analogs of esorubicin and methods for their use

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