CH657622A5 - Composti analoghi della daunorubicina e della doxorubicina, loro preparazione ed uso. - Google Patents

Composti analoghi della daunorubicina e della doxorubicina, loro preparazione ed uso. Download PDF

Info

Publication number: CH657622A5
Authority: CH; Switzerland
Prior art keywords: methyl; demethoxy; daunorubicin; compound according; dimethyl
Prior art date: 1982-01-26

Application number

CH317/83A

Other languages

English (en)

Italian (it)

Inventor

Sergio Penco

Giuliano Franchi

Federico Arcamone

Anna Maria Casazza

Original Assignee

Erba Farmitalia

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

1983-01-20

Publication date

1986-09-15

1983-01-20 Application filed by Erba Farmitalia filed Critical Erba Farmitalia

1986-09-15 Publication of CH657622A5 publication Critical patent/CH657622A5/it

Links

150000001875 compounds Chemical class 0.000 title claims description 35
238000002360 preparation method Methods 0.000 title claims description 5
AOJJSUZBOXZQNB-TZSSRYMLSA-N Doxorubicin 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)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 AOJJSUZBOXZQNB-TZSSRYMLSA-N 0.000 title description 97
229960004679 doxorubicin Drugs 0.000 claims description 48
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 claims description 21
229960000975 daunorubicin Drugs 0.000 claims description 17
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
229930182478 glucoside Natural products 0.000 claims description 9
150000008131 glucosides Chemical class 0.000 claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims description 9
239000001257 hydrogen Substances 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
238000000034 method Methods 0.000 claims description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
239000000243 solution Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
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 claims description 4
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 claims description 4
229960000908 idarubicin Drugs 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
239000004280 Sodium formate Substances 0.000 claims description 3
238000005904 alkaline hydrolysis reaction Methods 0.000 claims description 3
239000007864 aqueous solution Substances 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 claims description 3
239000002808 molecular sieve Substances 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
150000003839 salts Chemical class 0.000 claims description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 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
235000011121 sodium hydroxide Nutrition 0.000 claims description 3
239000002253 acid Substances 0.000 claims description 2
150000007513 acids Chemical class 0.000 claims description 2
230000031709 bromination Effects 0.000 claims description 2
238000005893 bromination reaction Methods 0.000 claims description 2
CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 claims description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
-1 methoxyl group Chemical group 0.000 claims 2
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 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
125000000325 methylidene group Chemical group [H]C([H])=* 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
206010028980 Neoplasm Diseases 0.000 description 32
241000699670 Mus sp. Species 0.000 description 31
210000004027 cell Anatomy 0.000 description 17
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 16
208000032839 leukemia Diseases 0.000 description 16
230000000694 effects Effects 0.000 description 13
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
231100000682 maximum tolerated dose Toxicity 0.000 description 12
238000007912 intraperitoneal administration Methods 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
231100000331 toxic Toxicity 0.000 description 9
230000002588 toxic effect Effects 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
230000004083 survival effect Effects 0.000 description 8
230000004614 tumor growth Effects 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000000259 anti-tumor effect Effects 0.000 description 7
238000011081 inoculation Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
206010006187 Breast cancer Diseases 0.000 description 6
208000026310 Breast neoplasm Diseases 0.000 description 6
210000001072 colon Anatomy 0.000 description 6
238000002474 experimental method Methods 0.000 description 6
206010048610 Cardiotoxicity Diseases 0.000 description 5
231100000259 cardiotoxicity Toxicity 0.000 description 5
230000034994 death Effects 0.000 description 5
231100000517 death Toxicity 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
230000003389 potentiating effect Effects 0.000 description 5
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 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
230000001093 anti-cancer Effects 0.000 description 4
230000007681 cardiovascular toxicity Effects 0.000 description 4
238000000338 in vitro Methods 0.000 description 4
230000001988 toxicity Effects 0.000 description 4
231100000419 toxicity Toxicity 0.000 description 4
238000011735 C3H mouse Methods 0.000 description 3
241000699666 Mus <mouse, genus> Species 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229940045799 anthracyclines and related substance Drugs 0.000 description 3
201000011510 cancer Diseases 0.000 description 3
231100000433 cytotoxic Toxicity 0.000 description 3
230000001472 cytotoxic effect Effects 0.000 description 3
238000001727 in vivo Methods 0.000 description 3
230000003902 lesion Effects 0.000 description 3
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 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
101100005766 Caenorhabditis elegans cdf-1 gene Proteins 0.000 description 2
208000013875 Heart injury Diseases 0.000 description 2
208000008342 Leukemia P388 Diseases 0.000 description 2
238000011888 autopsy Methods 0.000 description 2
230000004071 biological effect Effects 0.000 description 2
201000010897 colon adenocarcinoma Diseases 0.000 description 2
208000029742 colonic neoplasm Diseases 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000000354 decomposition reaction Methods 0.000 description 2
239000003480 eluent Substances 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
210000001035 gastrointestinal tract Anatomy 0.000 description 2
230000012010 growth Effects 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000002401 inhibitory effect Effects 0.000 description 2
230000007774 longterm Effects 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
231100000252 nontoxic Toxicity 0.000 description 2
230000003000 nontoxic effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
239000000725 suspension Substances 0.000 description 2
230000009885 systemic effect Effects 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NHBKXEKEPDILRR-UHFFFAOYSA-N 2,3-bis(butanoylsulfanyl)propyl butanoate Chemical compound CCCC(=O)OCC(SC(=O)CCC)CSC(=O)CCC NHBKXEKEPDILRR-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
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
208000007093 Leukemia L1210 Diseases 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
238000010521 absorption reaction Methods 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
238000003556 assay Methods 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
229940125904 compound 1 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
231100000135 cytotoxicity Toxicity 0.000 description 1
230000003013 cytotoxicity Effects 0.000 description 1
238000002784 cytotoxicity assay Methods 0.000 description 1
231100000263 cytotoxicity test Toxicity 0.000 description 1
230000006378 damage Effects 0.000 description 1
229960003109 daunorubicin hydrochloride Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
239000003814 drug Substances 0.000 description 1
230000008030 elimination Effects 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000434 field desorption mass spectrometry Methods 0.000 description 1
210000002837 heart atrium Anatomy 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000012750 in vivo screening Methods 0.000 description 1
208000014674 injury Diseases 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
239000002904 solvent 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
238000012360 testing method Methods 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000009466 transformation Effects 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
230000005748 tumor development Effects 0.000 description 1
230000003442 weekly effect 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)

CH317/83A 1982-01-26 1983-01-20 Composti analoghi della daunorubicina e della doxorubicina, loro preparazione ed uso. CH657622A5 (it)

Applications Claiming Priority (1)

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

Publications (1)

Publication Number	Publication Date
CH657622A5 true CH657622A5 (it)	1986-09-15

Family

ID=10527864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH317/83A CH657622A5 (it)	1982-01-26	1983-01-20	Composti analoghi della daunorubicina e della doxorubicina, loro preparazione ed uso.

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)	ES519255A0 (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
EP0022515B1 (en) *	1979-07-04	1983-08-03	FARMITALIA CARLO ERBA S.p.A.	Anthracycline glycosides, process for their preparation and therapeutical composition containing them
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 YU YU89/83A patent/YU43536B/xx unknown
- 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 FI FI830155A patent/FI74977C/fi not_active IP Right Cessation
- 1983-01-18 IT IT8319147A patent/IT1210482B/it active
- 1983-01-18 DE DE19833301489 patent/DE3301489A1/de active Granted
- 1983-01-18 IL IL67709A patent/IL67709A/xx unknown
- 1983-01-18 NZ NZ203047A patent/NZ203047A/en unknown
- 1983-01-18 CA CA000419718A patent/CA1197237A/en not_active Expired
- 1983-01-18 AT AT0015683A patent/AT378776B/de not_active IP Right Cessation
- 1983-01-19 PH PH28401A patent/PH19130A/en unknown
- 1983-01-19 JP JP58005974A patent/JPS58128396A/ja active Granted
- 1983-01-19 PT PT76113A patent/PT76113A/pt unknown
- 1983-01-19 CS CS83374A patent/CS235979B2/cs unknown
- 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 SU SU833542550A patent/SU1187724A3/ru active
- 1983-01-24 ZA ZA83450A patent/ZA83450B/xx unknown
- 1983-01-24 BE BE0/209955A patent/BE895687A/fr unknown
- 1983-01-24 GR GR70317A patent/GR77890B/el unknown
- 1983-01-25 IE IE144/83A patent/IE53750B1/en unknown
- 1983-01-25 DK DK027683A patent/DK157322C/da not_active IP Right Cessation
- 1983-01-25 KR KR1019830000279A patent/KR900006214B1/ko active IP Right Grant
- 1983-01-25 FR FR8301078A patent/FR2520365B1/fr not_active Expired
- 1983-01-25 ES ES519255A patent/ES519255A0/es active Granted
- 1983-01-25 HU HU83240A patent/HU192784B/hu not_active IP Right Cessation
- 1983-01-25 NO NO830234A patent/NO153456C/no unknown

Also Published As

Publication number	Publication date
ZA83450B (en)	1983-10-26
GB2116169A (en)	1983-09-21
NO153456C (no)	1986-03-26
BE895687A (fr)	1983-05-16
FR2520365A1 (fr)	1983-07-29
DK27683A (da)	1983-07-27
DK157322B (da)	1989-12-11
IE53750B1 (en)	1989-02-01
CA1197237A (en)	1985-11-26
AU1052583A (en)	1983-08-04
IL67709A (en)	1986-03-31
YU8983A (en)	1986-02-28
FI830155L (fi)	1983-07-27
DK157322C (da)	1990-05-07
GB8301178D0 (en)	1983-02-16
DE3301489C2 (ru)	1988-01-28
PT76113A (en)	1983-02-01
FR2520365B1 (fr)	1985-07-12
ES8403140A1 (es)	1984-03-01
NL8300150A (nl)	1983-08-16
SU1187724A3 (ru)	1985-10-23
FI830155A0 (fi)	1983-01-17
SE461591B (sv)	1990-03-05
DE3301489A1 (de)	1983-08-04
IL67709A0 (en)	1983-05-15
CS235979B2 (en)	1985-05-15
ATA15683A (de)	1985-02-15
SE8300324L (sv)	1983-07-27
AU551700B2 (en)	1986-05-08
NZ203047A (en)	1985-10-11
KR900006214B1 (ko)	1990-08-25
JPS58128396A (ja)	1983-07-30
KR840003262A (ko)	1984-08-20
NO830234L (no)	1983-07-27
ES519255A0 (es)	1984-03-01
JPS6328436B2 (ru)	1988-06-08
GB2116169B (en)	1985-09-04
IT8319147A0 (it)	1983-01-18
NO153456B (no)	1985-12-16
GR77890B (ru)	1984-09-25
IE830144L (en)	1983-07-26
HU192784B (en)	1987-07-28
DK27683D0 (da)	1983-01-25
YU43536B (en)	1989-08-31
IT1210482B (it)	1989-09-14
FI74977B (fi)	1987-12-31
SE8300324D0 (sv)	1983-01-21
FI74977C (fi)	1988-04-11
PH19130A (en)	1986-01-08
AT378776B (de)	1985-09-25

Publication	Publication Date	Title
PT89662B (pt)	1994-02-28	Processo para a preparacao de novos glicosidos antraciclinicos e de composicoes farmaceuticas que os contem
EP0889898B1 (en)	2002-02-20	Morpholinyl anthracycline derivatives
Penco et al.	1983	Synthesis, Antitumor Activity, and Cardiac Toxicity of New 4-Demethoxyanthracyclines¹
PT96226B (pt)	1998-06-30	Processo para a preparacao de derivados morfolinilicos de doxorubicina e de composicoes farmaceuticas que os contem
US5747502A (en)	1998-05-05	Process for preparing benzo c!phenanthridinium derivatives, novel compounds prepared by said process, and antitumor agents
CH657622A5 (it)	1986-09-15	Composti analoghi della daunorubicina e della doxorubicina, loro preparazione ed uso.
US3758455A (en)	1973-09-11	Reof mycophenolic acid glucuronide and the process for the preparation the
FI78109B (fi)	1989-02-28	Foerfarande foer framstaellning av antracyklinglykosider.
US4322412A (en)	1982-03-30	Anthracycline glycosides, their preparation, use and compositions thereof
JPH0660191B2 (ja)	1994-08-10	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
US4254110A (en)	1981-03-03	Pentofuranosyl anthracyclines, intermediates in and method for their preparation and compositions and use thereof
US4325947A (en)	1982-04-20	4-Demethoxy-4'-deoxydoxorubicin
RU2146261C1 (ru)	2000-03-10	8-фторантрациклины, способы их получения и содержащие их фармацевтические композиции
CH676985A5 (ru)	1991-03-28
EP0128670A1 (en)	1984-12-19	4-Demethoxy-3'-deamino-3'(4-morpholinyl) derivatives of anthracycline anticancer antibiotics
US4522815A (en)	1985-06-11	Anthracycline glycosides
US4604381A (en)	1986-08-05	4-demethoxy-13-dihydrodaunorubicin and use thereof
GB2034707A (en)	1980-06-11	Anthracycline glycosides
AU624839B2 (en)	1992-06-25	Morpholino derivatives of rhodomycins, processes for their preparation and their use
KR0177806B1 (ko)	1999-04-01	신규 안트라사이클린 글리코사이드 유도체 및 그 제조방법
JPH0232260B2 (ru)	1990-07-19
SK281797B6 (sk)	2001-08-06	Antracyklínové disacharidy, spôsob ich prípravy a farmaceutické prípravky s ich obsahom
FI70414B (fi)	1986-03-27	Foerfarande foer framstaellning av nya 4'-jododerivater av antracyklinglykosider
JPS6260397B2 (ru)	1987-12-16
MXPA01009025A (es)	2002-10-23	L-arabino-disacaridos de antraciclinas, proceso para su preparacion, y composiciones farmaceuticas que los contienen..

Legal Events

Date	Code	Title	Description
1988-06-15	PFA	Name/firm changed	Owner name: FARMITALIA CARLO ERBA S.R.L.
1991-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased