IL92052A - 4-הידרוקרביל 4-דמתוקסי- דאונומיצינונים ותהליך להכנתם - Google Patents

4-הידרוקרביל 4-דמתוקסי- דאונומיצינונים ותהליך להכנתם

Info

Publication number: IL92052A
Authority: IL; Israel
Prior art keywords: group; formula; daunomycinone; demethoxy; compound
Prior art date: 1988-10-25

Application number

IL9205289A

Other languages

English (en)

Other versions

IL92052A0 (en

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.)

1988-10-25

Filing date

1989-10-19

Publication date

1994-06-24

1989-10-19 Application filed by Erba Carlo Spa filed Critical Erba Carlo Spa

1989-10-19 Priority to IL10497489A priority Critical patent/IL104974A/he

1990-07-12 Publication of IL92052A0 publication Critical patent/IL92052A0/xx

1993-03-08 Priority to IL104974A priority patent/IL104974A0/xx

1994-06-24 Publication of IL92052A publication Critical patent/IL92052A/he

Links

238000004519 manufacturing process Methods 0.000 title description 2
125000000217 alkyl group Chemical group 0.000 claims abstract description 14
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
125000000304 alkynyl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 8
125000003118 aryl group Chemical group 0.000 claims abstract description 7
238000002360 preparation method Methods 0.000 claims abstract description 7
125000004185 ester group Chemical group 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000004665 trialkylsilyl group Chemical group 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 30
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 28
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 claims description 19
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 claims description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 11
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
-1 trimethylsilylethynyl Chemical group 0.000 claims description 10
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 6
239000000741 silica gel Substances 0.000 claims description 6
229910002027 silica gel Inorganic materials 0.000 claims description 6
150000003624 transition metals Chemical group 0.000 claims description 6
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
229920002554 vinyl polymer Polymers 0.000 claims description 6
238000004587 chromatography analysis Methods 0.000 claims description 5
229910052763 palladium Inorganic materials 0.000 claims description 5
238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 4
239000003054 catalyst Substances 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
125000006239 protecting group Chemical group 0.000 claims description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
230000007935 neutral effect Effects 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
150000002902 organometallic compounds Chemical class 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 2
150000001450 anions Chemical class 0.000 claims description 2
229910052793 cadmium Inorganic materials 0.000 claims description 2
BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
230000003197 catalytic effect Effects 0.000 claims description 2
150000004985 diamines Chemical class 0.000 claims description 2
239000003480 eluent Substances 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
229910052749 magnesium Inorganic materials 0.000 claims description 2
239000011777 magnesium Substances 0.000 claims description 2
OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
229910052718 tin Inorganic materials 0.000 claims description 2
229910052725 zinc Inorganic materials 0.000 claims description 2
239000011701 zinc Substances 0.000 claims description 2
239000002253 acid Substances 0.000 claims 1
239000007858 starting material Substances 0.000 claims 1
229940045799 anthracyclines and related substance Drugs 0.000 abstract description 4
239000000543 intermediate Substances 0.000 abstract description 4
229930182470 glycoside Natural products 0.000 abstract description 3
150000002338 glycosides Chemical class 0.000 abstract description 3
230000000259 anti-tumor effect Effects 0.000 abstract description 2
125000003368 amide group Chemical group 0.000 abstract 1
125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
150000003839 salts Chemical class 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000000243 solution Substances 0.000 description 9
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
239000008188 pellet Substances 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 7
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 5
229910000041 hydrogen chloride Inorganic materials 0.000 description 5
125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 5
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
239000011541 reaction mixture Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
238000005160 1H NMR spectroscopy Methods 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
239000012458 free base Substances 0.000 description 3
239000012074 organic phase Substances 0.000 description 3
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
UEXCJVNBTNXOEH-UHFFFAOYSA-N Ethynylbenzene Chemical group C#CC1=CC=CC=C1 UEXCJVNBTNXOEH-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000003446 ligand Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 2
239000012071 phase Substances 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000000047 product Substances 0.000 description 2
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
WEAHRLBPCANXCN-UHFFFAOYSA-N Daunomycin Natural products CCC1(O)CC(OC2CC(N)C(O)C(C)O2)c3cc4C(=O)c5c(OC)cccc5C(=O)c4c(O)c3C1 WEAHRLBPCANXCN-UHFFFAOYSA-N 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
238000007341 Heck reaction Methods 0.000 description 1
101000837626 Homo sapiens Thyroid hormone receptor alpha Proteins 0.000 description 1
UEZVMMHDMIWARA-UHFFFAOYSA-N Metaphosphoric acid Chemical compound OP(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-N 0.000 description 1
BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
239000004280 Sodium formate Substances 0.000 description 1
102100028702 Thyroid hormone receptor alpha Human genes 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000005250 alkyl acrylate group Chemical group 0.000 description 1
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
235000011114 ammonium hydroxide Nutrition 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
238000005899 aromatization reaction Methods 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
238000006254 arylation reaction Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000002738 chelating agent Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
229910021419 crystalline silicon Inorganic materials 0.000 description 1
229960004679 doxorubicin Drugs 0.000 description 1
229960002918 doxorubicin hydrochloride Drugs 0.000 description 1
GCSJLQSCSDMKTP-UHFFFAOYSA-N ethenyl(trimethyl)silane Chemical compound C[Si](C)(C)C=C GCSJLQSCSDMKTP-UHFFFAOYSA-N 0.000 description 1
KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
TYRRWPJYBCYJPG-UHFFFAOYSA-N n,n'-bis(diphenylphosphanyl)-n,n'-bis(1-phenylethyl)ethane-1,2-diamine Chemical compound C=1C=CC=CC=1C(C)N(P(C=1C=CC=CC=1)C=1C=CC=CC=1)CCN(P(C=1C=CC=CC=1)C=1C=CC=CC=1)C(C)C1=CC=CC=C1 TYRRWPJYBCYJPG-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
125000004151 quinonyl group Chemical group 0.000 description 1
102220043690 rs1049562 Human genes 0.000 description 1
229910000077 silane Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HLBBKKJFGFRGMU-UHFFFAOYSA-M sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 description 1
235000019254 sodium formate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 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
125000001424 substituent group Chemical group 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229910052723 transition metal Inorganic materials 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Molecular Biology (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Oncology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Medicinal Chemistry (AREA)
Communicable Diseases (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

IL9205289A 1988-10-25 1989-10-19 4-הידרוקרביל 4-דמתוקסי- דאונומיצינונים ותהליך להכנתם IL92052A (he)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
IL10497489A IL104974A (he)	1988-10-25	1989-10-19	4–דמתוקסי–4–מותמר–אנתראציקלין גליקוזידים והכנתם
IL104974A IL104974A0 (en)	1988-10-25	1993-03-08	Anthracycline glycosides,their preparation and pharmaceutical compositions containing them

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888824947A GB8824947D0 (en)	1988-10-25	1988-10-25	New 4-substituted anthracyclinones & process for preparing them

Publications (2)

Publication Number	Publication Date
IL92052A0 IL92052A0 (en)	1990-07-12
IL92052A true IL92052A (he)	1994-06-24

Family

ID=10645743

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9205289A IL92052A (he)	1988-10-25	1989-10-19	4-הידרוקרביל 4-דמתוקסי- דאונומיצינונים ותהליך להכנתם

Country Status (18)

Country	Link
US (1)	US5587495A (he)
EP (1)	EP0366973B1 (he)
JP (1)	JPH04501414A (he)
KR (1)	KR900701812A (he)
AT (1)	ATE99318T1 (he)
AU (1)	AU624444B2 (he)
DE (1)	DE68911855T2 (he)
DK (1)	DK168597B1 (he)
ES (1)	ES2061871T3 (he)
FI (1)	FI93364C (he)
GB (1)	GB8824947D0 (he)
HU (1)	HU207733B (he)
IE (1)	IE64161B1 (he)
IL (1)	IL92052A (he)
NZ (1)	NZ231052A (he)
PT (1)	PT92080B (he)
WO (1)	WO1990004601A1 (he)
ZA (1)	ZA898052B (he)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
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
GB8808475D0 (en) *	1988-04-11	1988-05-11	Erba Carlo Spa	Process for preparing 4-demethoxydauno-mycinone
NL9001834A (nl) *	1990-08-16	1992-03-16	Pharmachemie Bv	Nieuwe antracyclineverbindingen met anti-tumorwerkzaamheid, nieuwe tussenverbindingen voor de bereiding van deze antracyclineverbindingen, alsmede preparaten die de aktieve antracyclineverbindingen bevatten.
CN100379749C (zh) *	2003-05-21	2008-04-09	獀洛克斯股份有限公司	4-r-取代的4-去甲氧基柔红霉素的制备方法
US7053191B2 (en)	2003-05-21	2006-05-30	Solux Corporation	Method of preparing 4-R-substituted 4-demethoxydaunorubicin
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 (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1500421A (en) *	1975-01-22	1978-02-08	Farmaceutici Italia	Optically active anthracyclinones
US4116981A (en) *	1977-05-02	1978-09-26	Yuh-Geng Tsay	5,12-epoxy-naphthacene-6,11-dione derivatives
AU567978B2 (en) *	1983-10-19	1987-12-10	Anti-Cancer Council Of Victoria	Carminomycinone precursors and analogues and derivatives thereof.
IT1177014B (it) *	1983-10-19	1987-08-26	Univ Melbourne	Composti organici che comprendono antracicline e antraciclinoni

1988
- 1988-10-25 GB GB888824947A patent/GB8824947D0/en active Pending
1989
- 1989-10-06 ES ES89118648T patent/ES2061871T3/es not_active Expired - Lifetime
- 1989-10-06 DE DE89118648T patent/DE68911855T2/de not_active Expired - Fee Related
- 1989-10-06 EP EP89118648A patent/EP0366973B1/en not_active Expired - Lifetime
- 1989-10-06 AT AT89118648T patent/ATE99318T1/de not_active IP Right Cessation
- 1989-10-18 NZ NZ231052A patent/NZ231052A/xx unknown
- 1989-10-19 IL IL9205289A patent/IL92052A/he not_active IP Right Cessation
- 1989-10-23 IE IE340789A patent/IE64161B1/en not_active IP Right Cessation
- 1989-10-23 PT PT92080A patent/PT92080B/pt not_active IP Right Cessation
- 1989-10-24 WO PCT/EP1989/001266 patent/WO1990004601A1/en not_active Ceased
- 1989-10-24 JP JP1511359A patent/JPH04501414A/ja active Pending
- 1989-10-24 HU HU896397A patent/HU207733B/hu not_active IP Right Cessation
- 1989-10-24 US US07/678,352 patent/US5587495A/en not_active Expired - Fee Related
- 1989-10-24 AU AU44962/89A patent/AU624444B2/en not_active Ceased
- 1989-10-24 KR KR1019900701338A patent/KR900701812A/ko not_active Abandoned
- 1989-10-24 ZA ZA898052A patent/ZA898052B/xx unknown
1991
- 1991-04-22 FI FI911952A patent/FI93364C/fi not_active IP Right Cessation
- 1991-04-24 DK DK075291A patent/DK168597B1/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI93364C (fi)	1995-03-27
PT92080A (pt)	1990-04-30
EP0366973B1 (en)	1993-12-29
DK75291A (da)	1991-06-20
DK168597B1 (da)	1994-05-02
AU4496289A (en)	1990-05-14
PT92080B (pt)	1995-06-30
GB8824947D0 (en)	1988-11-30
US5587495A (en)	1996-12-24
IE64161B1 (en)	1995-07-12
HUT57228A (en)	1991-11-28
AU624444B2 (en)	1992-06-11
HU896397D0 (en)	1991-07-29
HU207733B (en)	1993-05-28
ATE99318T1 (de)	1994-01-15
JPH04501414A (ja)	1992-03-12
WO1990004601A1 (en)	1990-05-03
ZA898052B (en)	1990-08-29
NZ231052A (en)	1991-04-26
ES2061871T3 (es)	1994-12-16
IL92052A0 (en)	1990-07-12
EP0366973A1 (en)	1990-05-09
DE68911855D1 (de)	1994-02-10
FI911952A0 (fi)	1991-04-22
KR900701812A (ko)	1990-12-04
DE68911855T2 (de)	1994-04-21
FI93364B (fi)	1994-12-15
DK75291D0 (da)	1991-04-24
IE893407L (en)	1990-04-25

Legal Events

Date	Code	Title	Description
2000-12-06	RH	Patent void

Publication	Publication Date	Title
EP2176216B1 (en)	2012-04-25	Methods for synthesizing 9-substituted minocycline
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JP3554560B2 (ja)	2004-08-18	相間移動触媒を用いたインドロカルバゾールのグリコシド化
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IL92052A (he)	1994-06-24	4-הידרוקרביל 4-דמתוקסי- דאונומיצינונים ותהליך להכנתם
IE46165B1 (en)	1983-03-09	Daunomycinone derivatives
DK170157B1 (da)	1995-06-06	Fremgangsmåde til fremstilling af 4-demethoxydaunomycinon
EP0354995B1 (en)	1992-01-02	4-substituted anthracyclinones and anthracycline glycosides and their preparation
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JP2717023B2 (ja)	1998-02-18	アントラサイクリノンの製造方法
HU196821B (en)	1989-01-30	Process for producing 6-deoxy-antracyclin-glycoside derivatives
IL104974A (he)	1994-10-21	4–דמתוקסי–4–מותמר–אנתראציקלין גליקוזידים והכנתם
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Sanyal et al.	1984	Alkylphosphonium salts as a new class of antitumor agents
IL104975A (he)	1994-06-24	חומצות 4-דמתוקסידוקסורוביצין- ודאונומיצין -4-קרבוקסילית אסטרים שלהם, הכנתם ותכשירי רוקחות המכילים אותם
HU209598B (en)	1994-08-29	Process for producing 4-substituted anthracyclinones
JPH02164840A (ja)	1990-06-25	４‐ｏ‐アルキルロドマイシンの製造方法
HK1139386B (en)	2012-10-05	Methods for synthesizing 9-substituted minocycline