IE46122B1 - Antitumour glycosides - Google Patents
Antitumour glycosidesInfo
- Publication number
- IE46122B1 IE46122B1 IE2578/77A IE257877A IE46122B1 IE 46122 B1 IE46122 B1 IE 46122B1 IE 2578/77 A IE2578/77 A IE 2578/77A IE 257877 A IE257877 A IE 257877A IE 46122 B1 IE46122 B1 IE 46122B1
- Authority
- IE
- Ireland
- Prior art keywords
- desacetyl
- daunorubicin
- acyl
- process according
- carried out
- Prior art date
Links
- 230000000259 anti-tumor effect Effects 0.000 title abstract description 4
- 229930182470 glycoside Natural products 0.000 title description 2
- 150000002338 glycosides Chemical class 0.000 title description 2
- 238000000034 method Methods 0.000 claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 229960000975 daunorubicin Drugs 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 claims description 2
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 3
- 238000005917 acylation reaction Methods 0.000 claims 2
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 150000003840 hydrochlorides Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 9
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- 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 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000002904 solvent Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 3
- 206010028980 Neoplasm Diseases 0.000 description 3
- 229960004679 doxorubicin Drugs 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- NKZRZOVSJNSBFR-UHFFFAOYSA-N Doxorubicinol Natural products C1=2C(O)=C3C(=O)C=4C(OC)=CC=CC=4C(=O)C3=C(O)C=2CC(O)(C(O)CO)CC1OC1CC(N)C(O)C(C)O1 NKZRZOVSJNSBFR-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 150000001243 acetic acids Chemical class 0.000 description 2
- 229960004132 diethyl ether Drugs 0.000 description 2
- NKZRZOVSJNSBFR-FEMMEMONSA-N doxorubicinol 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@@H](O)CO)[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1 NKZRZOVSJNSBFR-FEMMEMONSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- LQLMJJJLWJUAMM-UHFFFAOYSA-N 7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-9-(1-hydroxyethyl)-4-methoxy-8,10-dihydro-7h-tetracene-5,12-dione;hydron;chloride Chemical compound Cl.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 LQLMJJJLWJUAMM-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical group CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- MWWSFMDVAYGXBV-RUELKSSGSA-N Doxorubicin hydrochloride Chemical compound Cl.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 MWWSFMDVAYGXBV-RUELKSSGSA-N 0.000 description 1
- 208000008342 Leukemia P388 Diseases 0.000 description 1
- 230000006181 N-acylation Effects 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000002927 anti-mitotic effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 238000005583 trifluoroacetylation reaction Methods 0.000 description 1
- 210000004881 tumor cell Anatomy 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
- 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)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB53455/76A GB1542920A (en) | 1976-12-22 | 1976-12-22 | Antitumour glycosides |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE46122L IE46122L (en) | 1978-06-22 |
| IE46122B1 true IE46122B1 (en) | 1983-02-23 |
Family
ID=10467876
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE2578/77A IE46122B1 (en) | 1976-12-22 | 1977-12-19 | Antitumour glycosides |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4146616A (en:Method) |
| JP (1) | JPS5379852A (en:Method) |
| AT (1) | AT355720B (en:Method) |
| AU (1) | AU518245B2 (en:Method) |
| BE (1) | BE862103A (en:Method) |
| CA (1) | CA1080703A (en:Method) |
| CH (1) | CH640870A5 (en:Method) |
| DE (1) | DE2757057A1 (en:Method) |
| DK (1) | DK564677A (en:Method) |
| FR (1) | FR2375251A1 (en:Method) |
| GB (1) | GB1542920A (en:Method) |
| IE (1) | IE46122B1 (en:Method) |
| NL (1) | NL7713906A (en:Method) |
| NZ (1) | NZ186048A (en:Method) |
| SE (1) | SE7714465L (en:Method) |
| YU (1) | YU301277A (en:Method) |
| ZA (1) | ZA777556B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5543012A (en) * | 1978-09-20 | 1980-03-26 | Sanraku Inc | Novel anthracycline derivatine and its preparation |
| US4254110A (en) * | 1979-02-02 | 1981-03-03 | Farmitalia Carlo Erba S.P.A. | Pentofuranosyl anthracyclines, intermediates in and method for their preparation and compositions and use thereof |
| US4604381A (en) * | 1982-07-16 | 1986-08-05 | Farmitalia Carlo Erba S.P.A. | 4-demethoxy-13-dihydrodaunorubicin and use thereof |
| FR2560876B1 (fr) * | 1984-03-09 | 1987-01-16 | Hoechst Lab | Nouvelles anthracyclinones, leur procede de preparation, nouveaux glycosides (anthracyclines) obtenus a partir de ces anthracyclinones, utilisation de ces glycosides en tant que medicaments |
| FR2584406B1 (fr) * | 1985-07-02 | 1988-09-09 | Hoechst Lab | Nouvelles tetralines, leurs procedes de preparation, leur utilisation pour la preparation des anthracyclinones et nouveaux glycosides (anthracyclines) obtenus a partir de ces anthracyclinones |
| DE3641835A1 (de) * | 1986-12-08 | 1988-06-16 | Behringwerke Ag | Zytostatisch wirksame anthracyclinderivate |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4020270A (en) * | 1974-05-02 | 1977-04-26 | Societa' Farmaceutici Italia S.P.A. | L-lyxohex-1-enopyranose derivative |
-
1976
- 1976-12-22 GB GB53455/76A patent/GB1542920A/en not_active Expired
-
1977
- 1977-12-14 US US05/860,448 patent/US4146616A/en not_active Expired - Lifetime
- 1977-12-15 NL NL7713906A patent/NL7713906A/xx not_active Application Discontinuation
- 1977-12-19 DK DK564677A patent/DK564677A/da not_active Application Discontinuation
- 1977-12-19 IE IE2578/77A patent/IE46122B1/en unknown
- 1977-12-19 YU YU03012/77A patent/YU301277A/xx unknown
- 1977-12-19 AU AU31749/77A patent/AU518245B2/en not_active Expired
- 1977-12-19 SE SE7714465A patent/SE7714465L/xx not_active Application Discontinuation
- 1977-12-19 AT AT907477A patent/AT355720B/de not_active IP Right Cessation
- 1977-12-19 FR FR7738200A patent/FR2375251A1/fr active Granted
- 1977-12-20 ZA ZA00777556A patent/ZA777556B/xx unknown
- 1977-12-20 NZ NZ186048A patent/NZ186048A/xx unknown
- 1977-12-21 JP JP15424777A patent/JPS5379852A/ja active Pending
- 1977-12-21 CA CA293,544A patent/CA1080703A/en not_active Expired
- 1977-12-21 BE BE183665A patent/BE862103A/xx unknown
- 1977-12-21 CH CH692582A patent/CH640870A5/de not_active IP Right Cessation
- 1977-12-21 DE DE19772757057 patent/DE2757057A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| CA1080703A (en) | 1980-07-01 |
| JPS5379852A (en) | 1978-07-14 |
| US4146616A (en) | 1979-03-27 |
| IE46122L (en) | 1978-06-22 |
| NL7713906A (nl) | 1978-06-26 |
| YU301277A (en) | 1982-06-30 |
| FR2375251A1 (fr) | 1978-07-21 |
| AT355720B (de) | 1980-03-25 |
| AU518245B2 (en) | 1981-09-24 |
| DE2757057A1 (de) | 1978-07-06 |
| DK564677A (da) | 1978-06-23 |
| NZ186048A (en) | 1980-05-08 |
| CH640870A5 (de) | 1984-01-31 |
| BE862103A (fr) | 1978-04-14 |
| AU3174977A (en) | 1979-06-28 |
| ATA907477A (de) | 1979-08-15 |
| FR2375251B1 (en:Method) | 1981-11-13 |
| ZA777556B (en) | 1978-09-27 |
| SE7714465L (sv) | 1978-06-23 |
| GB1542920A (en) | 1979-03-28 |
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