YU46455B - Postupak za dobijanje 4-demetoksi-4-amino-antra-ciklinona - Google Patents
Postupak za dobijanje 4-demetoksi-4-amino-antra-ciklinonaInfo
- Publication number
- YU46455B YU46455B YU75988A YU75988A YU46455B YU 46455 B YU46455 B YU 46455B YU 75988 A YU75988 A YU 75988A YU 75988 A YU75988 A YU 75988A YU 46455 B YU46455 B YU 46455B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- daunomycinone
- demethoxy
- deoxy
- hours
- Prior art date
Links
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 5
- 238000006243 chemical reaction Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 abstract 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 2
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 abstract 2
- XYDJGVROLWFENK-YBTHPKLGSA-N (7s,9s)-9-acetyl-4,6,7,9,11-pentahydroxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound O=C1C2=C(O)C=CC=C2C(=O)C2=C1C(O)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O XYDJGVROLWFENK-YBTHPKLGSA-N 0.000 abstract 1
- UIJPWDSKPZLJAN-UHFFFAOYSA-N 2-(1,4-dioxan-2-yl)ethanol Chemical compound OCCC1COCCO1 UIJPWDSKPZLJAN-UHFFFAOYSA-N 0.000 abstract 1
- -1 4-fluorobenzenesulfonyl Chemical group 0.000 abstract 1
- BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 abstract 1
- 239000004280 Sodium formate Substances 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229940045799 anthracyclines and related substance Drugs 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- CZKMPDNXOGQMFW-UHFFFAOYSA-N chloro(triethyl)germane Chemical compound CC[Ge](Cl)(CC)CC CZKMPDNXOGQMFW-UHFFFAOYSA-N 0.000 abstract 1
- 229930182478 glucoside Natural products 0.000 abstract 1
- 150000008131 glucosides Chemical class 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 238000010992 reflux Methods 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 abstract 1
- 235000019254 sodium formate Nutrition 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 abstract 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
POSTUPAK ZA DOBIJANJE 4-DEMETOKSI-4-AMINO-ANTRA-CIKLINONA, ili njihovih farmaceutski prihvatljivih adicionih soli sa kiselinama, naznacen time, sto obuhvata uklanjanje 7-hidroksilne grupe sa karminomicinona formule: rastvorenog u 1:1 smesi dioksan-etanol, hidrogenolizom u prisustvu 5% paladijuma na barijum sulfatu, na sobnoj temperaturi tokom 3 sata; reakciju dobijenog 4-demetil-7-dezoksi- daunomicinona formule: u anhidrovanom metilen hloridu, sa 4-fluorobenzolsulfonil hloridom, u prisustvu N,N-diizopropiletilamina i kataliticke kolicine 4-dimetilamino piridina; reakciju dobijenog 4-demetoksi- 4-(4-fluorobenzolsulfonil)-7-dezoksi-daunomicinona formule: u tetrahidrofuranu, sa benzilaminom na 40° C tokom 36 sati; uklanjanje benzil grupe sa dobijenog 4-demetoksi-4-benzilamino-7-dezoksi-daunomicinona formule: katalitickom hidrogenacijom u prisustvu 5% paladijuma na barijum sulfatu, pri pritisku od 1 bar, na sobnoj temperaturi i u trajanju od 1 sat, pri cemu se kao rastvarac koristi smesa etanola i sircetne kiseline sa katalitickom kolicinom 37% vodenog rastvora hlorovodonicne kiseline; zastitu 4-amino grupe u dobijenom 4-demetoksi-4-amino-7-dezoksi-daunomicinonu formule: reakcijom sa anhidridom trifluorosircetne kiseline, na 0° C, u anhidrovanom metilen dihloridu; ponovno uvodjenje 7-hidroksilne grupe u dobijeno zasticeno jedinjenje formule: tako sto se prvo vrsi zastita 13-keto grupe katalizacijom sa etilen glikolom na temperaturi refluksa, u prisustvu p- toluolsulfonske kiseline, sto dobijeni ketal reaguje na 40° C sa bromom u metilen dihloridu u prisustvu 2,2'-aza-bis- (izobutironitrila) tokom 3 sata, nakon cega se 7-bromovani intermedijer tretira sa vodenim rastvorom trifluorosircetne kiseline na 0° C tokom 1 sat, cime se dobija 4-demetoksi-4-N- trifluoroacetamido-daunomicinon formule: reakciju zasticenog derivata formule (XIII) sa zasticenim halosecerom formule: u kojoj Hal predstavlja atom hlora, u bezvodnom metilen dihloridu na temperaturi od 5° do 10° C i u prisustvu srebro trifluorometansulfonata, da bi se dobio 4-N-3',4'-N,O- antraciklinski trifluoroacetil zasticeni glukozid iz kojeg se, nakon tretmana sa 0.1N vodenim rastvorom natrijum hidroksida, na 0° C tokom 3 sata, dobija glikozidno jedinjenje formule (I) u kojoj R1 predstavlja vodonik, koje se izoluje u obliku hlorhidrata tretiranjem sa metanolskim rastvorom hlorovodonika; i, po potrebi, prevodjenje ovog proizvoda u njegov 14-bromo derivat, tretiranjem sa bromom u hloroformu da bi se, nakon hidrolize sa vodenim rastvorom natrijum formata, dobilo glikozidno jedinjenje formule (I) u kojoj R1 predstavlja hidroksilnu grupu, koje se takodje izoluje u obliku hlorhidrata.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SI8810759A SI8810759A8 (en) | 1987-04-21 | 1988-04-15 | Process for obtaining 4-demetoxy-4-amino-antracyclinones |
| YU94089A YU46489B (sh) | 1987-04-21 | 1989-05-08 | Postupak za dobijanje 4-demetoksi-antraciklinona |
| HR920898A HRP920898B1 (en) | 1987-04-21 | 1992-10-02 | 4-demethoxy-4-amino-anthracyclines and a process for the preparation thereof |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878709353A GB8709353D0 (en) | 1987-04-21 | 1987-04-21 | 4-demethoxy-4-amino-anthracyclines |
| GB888803302A GB8803302D0 (en) | 1988-02-12 | 1988-02-12 | Conversion of 4-demethoxy-4-amino anthracyclinones into 4-demethoxy-anthracyclinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU75988A YU75988A (en) | 1989-10-31 |
| YU46455B true YU46455B (sh) | 1993-10-20 |
Family
ID=26292154
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU75988A YU46455B (sh) | 1987-04-21 | 1988-04-15 | Postupak za dobijanje 4-demetoksi-4-amino-antra-ciklinona |
| YU94089A YU46489B (sh) | 1987-04-21 | 1989-05-08 | Postupak za dobijanje 4-demetoksi-antraciklinona |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU94089A YU46489B (sh) | 1987-04-21 | 1989-05-08 | Postupak za dobijanje 4-demetoksi-antraciklinona |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US4965351A (sh) |
| EP (2) | EP0288268B1 (sh) |
| JP (1) | JP2651414B2 (sh) |
| KR (1) | KR880012627A (sh) |
| CN (2) | CN1022038C (sh) |
| AT (2) | ATE83239T1 (sh) |
| AU (2) | AU600816B2 (sh) |
| CA (2) | CA1315775C (sh) |
| CS (2) | CS270585B2 (sh) |
| DE (2) | DE3876482T2 (sh) |
| DK (2) | DK170405B1 (sh) |
| ES (2) | ES2042737T3 (sh) |
| FI (1) | FI89263C (sh) |
| GR (2) | GR3007163T3 (sh) |
| HR (2) | HRP920898B1 (sh) |
| HU (2) | HU200188B (sh) |
| IE (1) | IE63510B1 (sh) |
| IL (1) | IL86088A (sh) |
| MY (2) | MY103365A (sh) |
| NO (1) | NO168702C (sh) |
| NZ (1) | NZ224252A (sh) |
| PT (2) | PT87270B (sh) |
| SI (1) | SI8810759A8 (sh) |
| SU (2) | SU1614764A3 (sh) |
| YU (2) | YU46455B (sh) |
| ZA (1) | ZA882732B (sh) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8803301D0 (en) * | 1988-02-12 | 1988-03-09 | Erba Carlo Spa | Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin |
| GB8818167D0 (en) * | 1988-07-29 | 1988-09-01 | Erba Carlo Spa | Novel 4-substituted anthracyclinones & process for their preparation |
| US5412081A (en) * | 1989-02-07 | 1995-05-02 | Farmitalia Carlo Erba S.R.L. | New 4'-epi-4'-amino anthracyclines |
| GB8904794D0 (en) * | 1989-03-02 | 1989-04-12 | Erba Carlo Spa | Process for preparing anthracyclinones |
| GB8905668D0 (en) * | 1989-03-13 | 1989-04-26 | Erba Carlo Spa | New 3'-(4-morpholinyl)-and 3'-(2-methoxy-4-morpholinyl)-anthracycline derivatives |
| GB9019934D0 (en) * | 1990-09-12 | 1990-10-24 | Erba Carlo Spa | 2-hydroxy-and 2-acyloxy-4-morpholinyl anthracyclines |
| GB9216962D0 (en) * | 1992-08-11 | 1992-09-23 | Erba Carlo Spa | Therapeutically active naphthalenesulfonic-pyrrolecarboxamido derivatives |
| GB9416007D0 (en) * | 1994-08-08 | 1994-09-28 | Erba Carlo Spa | Anthracyclinone derivatives |
| US5840737A (en) | 1996-01-04 | 1998-11-24 | The Curators Of The University Of Missouri | Omeprazole solution and method for using same |
| US6699885B2 (en) * | 1996-01-04 | 2004-03-02 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and methods of using same |
| US6645988B2 (en) | 1996-01-04 | 2003-11-11 | Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US6489346B1 (en) | 1996-01-04 | 2002-12-03 | The Curators Of The University Of Missouri | Substituted benzimidazole dosage forms and method of using same |
| US5948896A (en) * | 1997-08-13 | 1999-09-07 | Gem Pharmaceuticals | Processes for preparing 13-deoxy anthracycline derivatives |
| US5942605A (en) * | 1998-03-03 | 1999-08-24 | Gem Pharmaceuticals, Inc. | 5-imino-13-deoxy anthracycline derivatives, their uses, and processes for preparing them |
| KR20020008297A (ko) * | 2000-07-21 | 2002-01-30 | 채문식 | 안스라사이클린계 항생물질 도노마이신을 이용한식물병방제용 살균제 |
| WO2003063840A2 (en) * | 2002-01-25 | 2003-08-07 | Santarus, Inc. | Transmucosal delivery of proton pump inhibitors |
| EP1603537A4 (en) * | 2003-02-20 | 2009-11-04 | Santarus Inc | NOVEL FORMULATION, ANTICIPATED COMPLEX IMMEDIATE RELEASE FOR A FAST AND CONTINUOUS SUPPRESSION OF MAGIC ACID |
| US7053191B2 (en) * | 2003-05-21 | 2006-05-30 | Solux Corporation | Method of preparing 4-R-substituted 4-demethoxydaunorubicin |
| AR045062A1 (es) * | 2003-07-18 | 2005-10-12 | Santarus Inc | Formulaciones farmaceuticas para inhibir la secrecion de acido y metodos para preparar y utilizarlas |
| TWI337877B (en) * | 2003-07-18 | 2011-03-01 | Santarus Inc | Pharmaceutical formulation and method for treating acid-caused gastrointestinal disorders |
| US8993599B2 (en) | 2003-07-18 | 2015-03-31 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US20070292498A1 (en) * | 2003-11-05 | 2007-12-20 | Warren Hall | Combinations of proton pump inhibitors, sleep aids, buffers and pain relievers |
| US8815916B2 (en) | 2004-05-25 | 2014-08-26 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US8906940B2 (en) | 2004-05-25 | 2014-12-09 | Santarus, Inc. | Pharmaceutical formulations useful for inhibiting acid secretion and methods for making and using them |
| US7353034B2 (en) | 2005-04-04 | 2008-04-01 | X One, Inc. | Location sharing and tracking using mobile phones or other wireless devices |
| US20090092658A1 (en) * | 2007-10-05 | 2009-04-09 | Santarus, Inc. | Novel formulations of proton pump inhibitors and methods of using these formulations |
| US8357785B2 (en) * | 2008-01-08 | 2013-01-22 | Solux Corporation | Method of aralkylation of 4′-hydroxyl group of anthracylins |
| US8846882B2 (en) | 2011-04-29 | 2014-09-30 | Synbias Pharma Ag | Method of producing 4-demethoxydaunorubicin |
| US9828405B2 (en) | 2013-04-29 | 2017-11-28 | Nerviano Medical Sciences S.R.L. | Morpholinyl anthracycline derivatives |
| US20170312290A1 (en) | 2014-11-05 | 2017-11-02 | Nerviano Medical Sciences S.R.L. | Functionalized morpholinyl anthracycline derivatives |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE905014C (de) * | 1944-09-23 | 1954-02-25 | Cassella Farbwerke Mainkur Ag | Verfahren zum Ersatz der Diazogruppe durch Wasserstoff |
| US3803124A (en) | 1968-04-12 | 1974-04-09 | Farmaceutici It Soc | Process for the preparation of adriamycin and adriamycinone and adriamycin derivatives |
| GB1467383A (en) * | 1974-06-12 | 1977-03-16 | Farmaceutici Italia | Daunomycin analogues |
| GB1500421A (en) * | 1975-01-22 | 1978-02-08 | Farmaceutici Italia | Optically active anthracyclinones |
| GB1511559A (en) | 1975-09-26 | 1978-05-24 | Farmaceutici Italia | Anthracycline glycosides |
| US4021457A (en) * | 1975-11-18 | 1977-05-03 | Research Corporation | Intermediates for polycyclic quinonoid antibiotics |
| US4012448A (en) * | 1976-01-15 | 1977-03-15 | Stanford Research Institute | Synthesis of adriamycin and 7,9-epiadriamycin |
| GB1509875A (en) * | 1976-06-14 | 1978-05-04 | Farmaceutici Italia | Optically active anthracyclinones and anthracycline glycosides |
| GB1567456A (en) * | 1976-11-16 | 1980-05-14 | Farmaceutici Italia | Daunomycin derivatives |
| US4109076A (en) * | 1977-09-08 | 1978-08-22 | Sri International | 5-iminodaunomycin |
| US4348388A (en) * | 1980-04-02 | 1982-09-07 | G.D. Searle & Co. | 11-Amino-11-deoxydaunorubicin and analogs |
| ATE8401T1 (de) * | 1980-11-01 | 1984-07-15 | Farmitalia Carlo Erba S.P.A. | Anthracyclin-glycoside, verfahren zu ihrer herstellung, zwischenprodukte und ihre herstellung und arzneimittel. |
| US4413120A (en) * | 1981-04-06 | 1983-11-01 | Purdue Research Foundation | Process for producing acosamine, daunosamine, 1-thioacosamine and related compounds |
| IT1168014B (it) * | 1981-08-05 | 1987-05-20 | Erba Farmitalia | Forme farmaceutiche a cessione protratta |
| US4563444A (en) * | 1982-05-26 | 1986-01-07 | Farmitalia Carlo Erba S.P.A. | Anthracycline glycosides, use and compositions containing same |
| US4448724A (en) * | 1982-12-20 | 1984-05-15 | The Trustees Of The University Of Pennsylvania | Synthesis of 4-demethoxydaunomycinone |
| WO1985001726A1 (en) * | 1983-10-19 | 1985-04-25 | The University Of Melbourne | Carminomycinone precursors and analogues and derivatives thereof |
| US4564674A (en) * | 1983-10-31 | 1986-01-14 | Sagami Chemical Research Center | Process for an anthracycline derivative, and an anthracyclinone derivative useful for the process |
| US4591637A (en) * | 1985-01-17 | 1986-05-27 | Sri International | Open chain-morpholino adriamycins |
| GB8617742D0 (en) * | 1986-07-21 | 1986-08-28 | Erba Farmitalia | 6-amino anthracyclines |
| GB8803301D0 (en) * | 1988-02-12 | 1988-03-09 | Erba Carlo Spa | Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin |
-
1988
- 1988-04-14 NZ NZ224252A patent/NZ224252A/xx unknown
- 1988-04-15 AU AU14695/88A patent/AU600816B2/en not_active Ceased
- 1988-04-15 SI SI8810759A patent/SI8810759A8/sl not_active IP Right Cessation
- 1988-04-15 YU YU75988A patent/YU46455B/sh unknown
- 1988-04-15 IL IL86088A patent/IL86088A/xx not_active IP Right Cessation
- 1988-04-18 HU HU881983A patent/HU200188B/hu not_active IP Right Cessation
- 1988-04-18 FI FI881792A patent/FI89263C/fi active IP Right Grant
- 1988-04-18 HU HU881983A patent/HU202810B/hu not_active IP Right Cessation
- 1988-04-18 DK DK210688A patent/DK170405B1/da not_active IP Right Cessation
- 1988-04-19 KR KR1019880004424A patent/KR880012627A/ko not_active Ceased
- 1988-04-19 IE IE117188A patent/IE63510B1/en not_active IP Right Cessation
- 1988-04-19 CS CS882658A patent/CS270585B2/cs not_active IP Right Cessation
- 1988-04-19 PT PT87270A patent/PT87270B/pt not_active IP Right Cessation
- 1988-04-19 ZA ZA882732A patent/ZA882732B/xx unknown
- 1988-04-20 EP EP88303561A patent/EP0288268B1/en not_active Expired - Lifetime
- 1988-04-20 AT AT88303561T patent/ATE83239T1/de not_active IP Right Cessation
- 1988-04-20 CA CA000564613A patent/CA1315775C/en not_active Expired - Fee Related
- 1988-04-20 MY MYPI88000396A patent/MY103365A/en unknown
- 1988-04-20 ES ES88303561T patent/ES2042737T3/es not_active Expired - Lifetime
- 1988-04-20 AT AT91100002T patent/ATE141251T1/de not_active IP Right Cessation
- 1988-04-20 EP EP91100002A patent/EP0426653B1/en not_active Expired - Lifetime
- 1988-04-20 JP JP63098032A patent/JP2651414B2/ja not_active Expired - Fee Related
- 1988-04-20 DE DE8888303561T patent/DE3876482T2/de not_active Expired - Fee Related
- 1988-04-20 DE DE3855480T patent/DE3855480T2/de not_active Expired - Fee Related
- 1988-04-20 NO NO881710A patent/NO168702C/no not_active IP Right Cessation
- 1988-04-20 ES ES91100002T patent/ES2093034T3/es not_active Expired - Lifetime
- 1988-04-20 SU SU884355593A patent/SU1614764A3/ru active
- 1988-04-20 CN CN88102182A patent/CN1022038C/zh not_active Expired - Fee Related
- 1988-10-27 CS CS887117A patent/CS270596B2/cs not_active IP Right Cessation
- 1988-11-04 SU SU884356729A patent/SU1729294A3/ru active
-
1989
- 1989-05-08 YU YU94089A patent/YU46489B/sh unknown
- 1989-11-01 US US07/430,149 patent/US4965351A/en not_active Expired - Lifetime
-
1990
- 1990-01-09 US US07/462,549 patent/US4985548A/en not_active Expired - Lifetime
- 1990-05-25 AU AU55916/90A patent/AU621222B2/en not_active Ceased
-
1991
- 1991-11-05 CA CA000616216A patent/CA1318665C/en not_active Expired - Fee Related
-
1992
- 1992-09-12 CN CN92110559A patent/CN1024545C/zh not_active Expired - Fee Related
- 1992-09-18 MY MYPI92001675A patent/MY104645A/en unknown
- 1992-10-02 HR HR920898A patent/HRP920898B1/xx not_active IP Right Cessation
- 1992-10-02 HR HRP-940/89A patent/HRP920920B1/xx not_active IP Right Cessation
-
1993
- 1993-02-08 PT PT101194A patent/PT101194B/pt not_active IP Right Cessation
- 1993-02-25 GR GR930400400T patent/GR3007163T3/el unknown
-
1994
- 1994-09-12 DK DK199401046A patent/DK174561B1/da not_active IP Right Cessation
-
1996
- 1996-09-12 GR GR960402354T patent/GR3021004T3/el unknown
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