CS273198B2 - Method of 4-demethoxydaunomycinone production - Google Patents

Method of 4-demethoxydaunomycinone production Download PDF

Info

Publication number: CS273198B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; resulting; group; process according; demethyl
Prior art date: 1988-02-12

Application number

CS80789A

Other languages

Czech (cs)

English (en)

Other versions

CS80789A2 (en

Inventor

Bernardinis Silvia De

Walter Cabri

Tiziano Martinengo

Franco Francalanci

Original Assignee

Erba Carlo 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.)

1988-02-12

Filing date

1989-02-07

Publication date

1991-03-12

1989-02-07 Application filed by Erba Carlo Spa filed Critical Erba Carlo Spa

1990-06-13 Publication of CS80789A2 publication Critical patent/CS80789A2/cs

1991-03-12 Publication of CS273198B2 publication Critical patent/CS273198B2/cs

Links

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 title claims abstract description 8
238000000034 method Methods 0.000 title claims description 10
238000004519 manufacturing process Methods 0.000 title claims 2
150000001412 amines Chemical class 0.000 claims abstract description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 15
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 6
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
230000003197 catalytic effect Effects 0.000 claims description 3
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
235000010288 sodium nitrite Nutrition 0.000 claims description 3
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 2
FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims 1
239000003638 chemical reducing agent Substances 0.000 claims 1
150000001875 compounds Chemical class 0.000 abstract description 6
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 abstract description 3
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 abstract description 3
229960000908 idarubicin Drugs 0.000 abstract description 3
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 description 2
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 abstract description 2
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 abstract description 2
PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 abstract description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
150000001989 diazonium salts Chemical class 0.000 abstract 1
125000006239 protecting group Chemical group 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000002585 base Substances 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
238000005160 1H NMR spectroscopy Methods 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
238000004128 high performance liquid chromatography Methods 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
239000000047 product Substances 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229910052739 hydrogen Inorganic materials 0.000 description 3
-1 p-methoxybenzyl group Chemical group 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
YOFDHOWPGULAQF-MQJDWESPSA-N (7s,9s)-9-acetyl-6,7,9,11-tetrahydroxy-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione Chemical compound 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 description 2
ZUFQFGSMHXKORU-YUNKPMOVSA-N (7s,9s)-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)=C1[C@@H](O)C[C@@](C(=O)C)(O)CC1=C2O ZUFQFGSMHXKORU-YUNKPMOVSA-N 0.000 description 2
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
230000003115 biocidal effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000012043 crude product Substances 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000012071 phase Substances 0.000 description 2
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
AGUPHKGJZBMPMX-UHFFFAOYSA-N 1-(2-hydroxy-5,8-dimethoxy-5,6,7,8-tetrahydro-1h-naphthalen-2-yl)ethanone Chemical compound C1C(O)(C(C)=O)C=CC2=C1C(OC)CCC2OC AGUPHKGJZBMPMX-UHFFFAOYSA-N 0.000 description 1
IDPURXSQCKYKIJ-UHFFFAOYSA-N 1-(4-methoxyphenyl)methanamine Chemical compound COC1=CC=C(CN)C=C1 IDPURXSQCKYKIJ-UHFFFAOYSA-N 0.000 description 1
XDPFSAXBVHBYLO-UHFFFAOYSA-N 1h-diazonine Chemical class C=1C=CC=NNC=CC=1 XDPFSAXBVHBYLO-UHFFFAOYSA-N 0.000 description 1
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 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229940041181 antineoplastic drug Drugs 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000003431 cross linking reagent Substances 0.000 description 1
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 description 1
229960000975 daunorubicin Drugs 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000008188 pellet Substances 0.000 description 1
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
REFMEZARFCPESH-UHFFFAOYSA-M sodium;heptane-1-sulfonate Chemical compound [Na+].CCCCCCCS([O-])(=O)=O REFMEZARFCPESH-UHFFFAOYSA-M 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000006103 sulfonylation Effects 0.000 description 1
238000005694 sulfonylation reaction Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C50/00—Quinones
- C07C50/38—Quinones containing —CHO or non—quinoid keto groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/40—Ortho- or ortho- and peri-condensed systems containing four condensed rings
- C07C2603/42—Ortho- or ortho- and peri-condensed systems containing four condensed rings containing only six-membered rings
- C07C2603/44—Naphthacenes; Hydrogenated naphthacenes
- C07C2603/46—1,4,4a,5,5a,6,11,12a- Octahydronaphthacenes, e.g. tetracyclines
- 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)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Compounds Of Unknown Constitution (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Cephalosporin Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

CS80789A 1988-02-12 1989-02-07 Method of 4-demethoxydaunomycinone production CS273198B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888803301A GB8803301D0 (en)	1988-02-12	1988-02-12	Process for preparation of 4-demethoxy-daunomycinone aglycone of 4-demethoxy-daunorubicin

Publications (2)

Publication Number	Publication Date
CS80789A2 CS80789A2 (en)	1990-06-13
CS273198B2 true CS273198B2 (en)	1991-03-12

Family

ID=10631620

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS80789A CS273198B2 (en)	1988-02-12	1989-02-07	Method of 4-demethoxydaunomycinone production

Country Status (26)

Country	Link
US (1)	US5015745A (ru)
EP (1)	EP0328399B1 (ru)
JP (1)	JP2784202B2 (ru)
KR (1)	KR970000484B1 (ru)
CN (1)	CN1020592C (ru)
AT (1)	ATE92457T1 (ru)
AU (1)	AU605960B2 (ru)
CA (1)	CA1339634C (ru)
CS (1)	CS273198B2 (ru)
DE (1)	DE68907934T2 (ru)
DK (1)	DK170248B1 (ru)
ES (1)	ES2059718T3 (ru)
FI (1)	FI92186C (ru)
GB (1)	GB8803301D0 (ru)
HU (1)	HU200979B (ru)
IE (1)	IE62954B1 (ru)
IL (1)	IL89198A (ru)
MY (1)	MY104941A (ru)
NO (1)	NO169483C (ru)
NZ (1)	NZ227873A (ru)
PH (1)	PH27328A (ru)
PT (1)	PT89663B (ru)
RU (1)	RU1819256C (ru)
UA (1)	UA19151A (ru)
YU (1)	YU47206B (ru)
ZA (1)	ZA891018B (ru)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NZ224252A (en) *	1987-04-21	1991-09-25	Erba Carlo Spa	An anthracycline glycoside and its preparation
GB8808475D0 (en) *	1988-04-11	1988-05-11	Erba Carlo Spa	Process for preparing 4-demethoxydauno-mycinone
IT1275953B1 (it) *	1995-03-22	1997-10-24	Sicor Spa	Procedimento per la preparazione di antibiotici della classe delle antracicline
AUPQ319799A0 (en) *	1999-10-01	1999-10-28	Institute Of Drug Technology Australia Limited	Chemical methods
US7053191B2 (en)	2003-05-21	2006-05-30	Solux Corporation	Method of preparing 4-R-substituted 4-demethoxydaunorubicin
TW200621698A (en) *	2004-08-23	2006-07-01	Sicor Inc	Synthesis of idarubicin aglycone
DE06848583T1 (de)	2005-12-13	2011-03-17	Solux Corporation, San Diego	Verfahren zur herstellung von 4-demethyldaunorubicin
US8802830B2 (en)	2005-12-20	2014-08-12	Solux Corporation	Synthesis of epirubicin from 13-dihydrodaunorubicine
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

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3862225A (en) *	1961-08-18	1975-01-21	Pfizer	D-ring substituted tetracyclines
US4020270A (en) *	1974-05-02	1977-04-26	Societa' Farmaceutici Italia S.P.A.	L-lyxohex-1-enopyranose derivative
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
GB1509875A (en) *	1976-06-14	1978-05-04	Farmaceutici Italia	Optically active anthracyclinones and anthracycline glycosides
GB1527050A (en) *	1976-06-19	1978-10-04	Farmaceutici Italia	Optically active anthracyclinones
GB8317037D0 (en) *	1983-06-23	1983-07-27	Erba Farmitalia	6-deoxyanthracyclines
US4495103A (en) *	1982-07-30	1985-01-22	Sumitomo Chemical Company, Ltd.	Preparation of optically active 4-demethoxydaunomycinone
EP0159357B1 (en) *	1983-10-19	1992-09-09	The University Of Melbourne	Carminomycinone precursors and analogues and derivatives thereof
NZ224252A (en) *	1987-04-21	1991-09-25	Erba Carlo Spa	An anthracycline glycoside and its preparation
GB8808475D0 (en) *	1988-04-11	1988-05-11	Erba Carlo Spa	Process for preparing 4-demethoxydauno-mycinone
GB8824947D0 (en) *	1988-10-25	1988-11-30	Erba Carlo Spa	New 4-substituted anthracyclinones & process for preparing them

1988
- 1988-02-12 GB GB888803301A patent/GB8803301D0/en active Pending
1989
- 1989-02-06 US US07/306,559 patent/US5015745A/en not_active Expired - Lifetime
- 1989-02-06 PH PH38165A patent/PH27328A/en unknown
- 1989-02-07 IL IL8919889A patent/IL89198A/en not_active IP Right Cessation
- 1989-02-07 CS CS80789A patent/CS273198B2/cs unknown
- 1989-02-07 IE IE38389A patent/IE62954B1/en not_active IP Right Cessation
- 1989-02-07 NZ NZ227873A patent/NZ227873A/xx unknown
- 1989-02-08 KR KR1019890001402A patent/KR970000484B1/ko not_active Expired - Fee Related
- 1989-02-08 AU AU29745/89A patent/AU605960B2/en not_active Ceased
- 1989-02-08 YU YU31089A patent/YU47206B/sh unknown
- 1989-02-09 ZA ZA891018A patent/ZA891018B/xx unknown
- 1989-02-09 NO NO890566A patent/NO169483C/no unknown
- 1989-02-09 PT PT89663A patent/PT89663B/pt not_active IP Right Cessation
- 1989-02-09 JP JP1030929A patent/JP2784202B2/ja not_active Expired - Fee Related
- 1989-02-09 UA UA4613419A patent/UA19151A/ru unknown
- 1989-02-09 FI FI890612A patent/FI92186C/fi active IP Right Grant
- 1989-02-09 RU SU894613419A patent/RU1819256C/ru not_active IP Right Cessation
- 1989-02-10 AT AT89301282T patent/ATE92457T1/de not_active IP Right Cessation
- 1989-02-10 ES ES89301282T patent/ES2059718T3/es not_active Expired - Lifetime
- 1989-02-10 MY MYPI89000165A patent/MY104941A/en unknown
- 1989-02-10 HU HU89630A patent/HU200979B/hu unknown
- 1989-02-10 CN CN89100740A patent/CN1020592C/zh not_active Expired - Fee Related
- 1989-02-10 EP EP89301282A patent/EP0328399B1/en not_active Expired - Lifetime
- 1989-02-10 DK DK063889A patent/DK170248B1/da not_active IP Right Cessation
- 1989-02-10 DE DE89301282T patent/DE68907934T2/de not_active Expired - Fee Related
- 1989-02-10 CA CA000590705A patent/CA1339634C/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
RU1819256C (en)	1993-05-30
KR890012931A (ko)	1989-09-20
DK63889D0 (da)	1989-02-10
UA19151A (ru)	1997-12-25
FI92186C (fi)	1994-10-10
ZA891018B (en)	1989-10-25
HU200979B (en)	1990-09-28
NO169483C (no)	1992-07-01
EP0328399A2 (en)	1989-08-16
FI890612A0 (fi)	1989-02-09
US5015745A (en)	1991-05-14
IE62954B1 (en)	1995-02-20
EP0328399B1 (en)	1993-08-04
CS80789A2 (en)	1990-06-13
NO890566D0 (no)	1989-02-09
KR970000484B1 (ko)	1997-01-13
ES2059718T3 (es)	1994-11-16
JP2784202B2 (ja)	1998-08-06
YU31089A (en)	1990-08-31
FI92186B (fi)	1994-06-30
IE890383L (en)	1989-08-12
AU605960B2 (en)	1991-01-24
NZ227873A (en)	1990-09-26
HUT49319A (en)	1989-09-28
DE68907934D1 (de)	1993-09-09
NO890566L (no)	1989-08-11
GB8803301D0 (en)	1988-03-09
DK63889A (da)	1989-08-13
EP0328399A3 (en)	1990-03-07
IL89198A (en)	1994-10-07
PT89663A (pt)	1989-10-04
DK170248B1 (da)	1995-07-17
ATE92457T1 (de)	1993-08-15
IL89198A0 (en)	1989-09-10
CN1037152A (zh)	1989-11-15
JPH021423A (ja)	1990-01-05
CA1339634C (en)	1998-01-20
NO169483B (no)	1992-03-23
MY104941A (en)	1994-07-30
DE68907934T2 (de)	1994-04-28
PH27328A (en)	1993-06-08
PT89663B (pt)	1994-02-28
FI890612L (fi)	1989-08-13
CN1020592C (zh)	1993-05-12
AU2974589A (en)	1989-08-17
YU47206B (sh)	1995-01-31

Legal Events

Date	Code	Title	Description
2000-06-30	IF00	In force as of 2000-06-30 in czech republic

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