GB1502121A - Anthracyclines - Google Patents
AnthracyclinesInfo
- Publication number
- GB1502121A GB1502121A GB32384/75A GB3238475A GB1502121A GB 1502121 A GB1502121 A GB 1502121A GB 32384/75 A GB32384/75 A GB 32384/75A GB 3238475 A GB3238475 A GB 3238475A GB 1502121 A GB1502121 A GB 1502121A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dideoxy
- resulting
- trifluoroacetamido
- hydroxy
- nitrobenzoyl
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Crystallography & Structural Chemistry (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1502121 Daunomycin and adriamycin derivatives SOC FARMACEUTICI ITALIA SpA 28 July 1976 [2 Aug 1975] 32384/75 Heading C2C Novel 6<SP>1</SP> - hydroxy- and 4 - demethoxy - 6<SP>1</SP>- hydroxy - adriamycin are prepared by conversion of the corresponding daunomycin derivative by the method of Specification 1,217,133. They may be isolated as the hydrochloride salts. Novel 6<SP>1</SP> - hydroxy- and 4 - demethoxy - 6<SP>1</SP>- hydroxy - daunomycin are prepared by subjecting the corresponding 3<SP>1</SP>-N-trifluoroacetyl - 4<SP>1</SP>,6<SP>1</SP>, - di - O - p - nitrobenzoyl derivative to alkaline conditions. They may be isolated as the hydrochloride salts. 3<SP>1</SP> - N - Trifluoroacetyl - 4<SP>1</SP>,6<SP>1</SP> - di - O - p - nitrobenzoyl - 6<SP>1</SP> - hydroxy- and 4 - demethoxy - 6<SP>1</SP>- hydroxy - daunomycin α and # anomers are prepared by condensing daunomycinone or its 4-demethoxy derivative with 2,3-dideoxy-3- trifluoroacetamido - 4,6 - di - O - p - nitrobenzoyl-α-L-lyxohexopyranosyl chloride. 2,3 - Dideoxy - 3 - trifluoroacetamido - 4,6 - di- O - p - nitrobenzoyl α - L - lyxohexopyranosyl chloride is prepared by reacting methyl 3- trifluoroacetamido - 2,3 - dideoxy - α - L- arabinohexopyranoside with trityl chloride, oxidizing the resulting 6-O-trityl derivative with ruthenium tetroxide, reducing the resulting methyl 2,3 - dideoxy - 3 - trifluoroacetamido - 6- O - trityl - α - L - threohexopyranoside - 4 - ulose with lithium tri-sec. butyl borohydride, treating the resulting methyl 2,3-dideoxy-3-trifluoroacetamido - 6 - O - trityl - α - L - lyxohexopyranoside with aqueous acetic acid, reacting the resulting detritylated derivative with HCl, treating the resulting 3 - amino - 2,3 - dideoxy - α - L - lyxohexose with trifluoroacetic anhydride and isopropyl alcohol, reacting the resulting isopropyl 3 - trifluoroacetamido - 2,3 - dideoxy - α - L- lyxohexopyranoside with p-nitrobenzoyl chloride and treating the resulting 4,6-di-O-p-nitrobenzoyl derivative with HCl.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32384/75A GB1502121A (en) | 1975-08-02 | 1975-08-02 | Anthracyclines |
| DE19762633913 DE2633913A1 (en) | 1975-08-02 | 1976-07-28 | 6'-HYDROXYDE DERIVATIVES OF ANTITUMORANTHRACYCLINES |
| FR7623207A FR2320306A1 (en) | 1975-08-02 | 1976-07-29 | 6 '-HYDROXY DERIVATIVES OF ANTITUMORAL ANTHRACYCLINES |
| JP51091192A JPS5219651A (en) | 1975-08-02 | 1976-07-30 | 66hydroxy derivatives of anthracyclinone * preparation thereof and antiitumor pharmaceutical composition containing same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB32384/75A GB1502121A (en) | 1975-08-02 | 1975-08-02 | Anthracyclines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1502121A true GB1502121A (en) | 1978-02-22 |
Family
ID=10337769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB32384/75A Expired GB1502121A (en) | 1975-08-02 | 1975-08-02 | Anthracyclines |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPS5219651A (en) |
| DE (1) | DE2633913A1 (en) |
| FR (1) | FR2320306A1 (en) |
| GB (1) | GB1502121A (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4345068A (en) * | 1979-11-22 | 1982-08-17 | Farmitalia Carlo Erba S.P.A. | Process for the preparation of 4'-epidaunorubicin, 3',4'-diepidaunorubicin, their doxorubicin analogs, and intermediates used in said process |
| JPS58156596U (en) * | 1982-04-13 | 1983-10-19 | 株式会社西原環境衛生研究所 | Sewage treatment equipment |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1470860A (en) * | 1974-10-29 | 1977-04-21 | Farmaceutici Italia | Anthracycline glycosides |
-
1975
- 1975-08-02 GB GB32384/75A patent/GB1502121A/en not_active Expired
-
1976
- 1976-07-28 DE DE19762633913 patent/DE2633913A1/en not_active Withdrawn
- 1976-07-29 FR FR7623207A patent/FR2320306A1/en active Granted
- 1976-07-30 JP JP51091192A patent/JPS5219651A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FR2320306B1 (en) | 1978-05-05 |
| FR2320306A1 (en) | 1977-03-04 |
| JPS5219651A (en) | 1977-02-15 |
| DE2633913A1 (en) | 1977-02-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |