ATE733T1 - 2'-DEOXY-5-FLUOROURIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND ANTITUMORS COMPOSITIONS CONTAINING THEM. - Google Patents
2'-DEOXY-5-FLUOROURIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND ANTITUMORS COMPOSITIONS CONTAINING THEM.Info
- Publication number
- ATE733T1 ATE733T1 AT79301782T AT79301782T ATE733T1 AT E733 T1 ATE733 T1 AT E733T1 AT 79301782 T AT79301782 T AT 79301782T AT 79301782 T AT79301782 T AT 79301782T AT E733 T1 ATE733 T1 AT E733T1
- Authority
- AT
- Austria
- Prior art keywords
- deoxy
- fluorouridine
- antitumors
- preparation
- compositions containing
- Prior art date
Links
- ODKNJVUHOIMIIZ-RRKCRQDMSA-N floxuridine Chemical class C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(F)=C1 ODKNJVUHOIMIIZ-RRKCRQDMSA-N 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000000259 anti-tumor effect Effects 0.000 abstract 1
- 239000002246 antineoplastic agent Substances 0.000 abstract 1
- -1 benzoyl halide Chemical class 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 231100000053 low toxicity Toxicity 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/06—Pyrimidine radicals
-
- 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)
Abstract
Novel 2 min -deoxy-5- fluorouridine derivatives represented by the formula;
<CHEM>
wherein R represents a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an acetyloxy group or a halogen atom, and n is an a integer in the range of 1 to 3 are provided. These have good antitumor activities and low toxicities and are suitable for use as antitumor agents. The new compounds may be prepared by reacting 2 min -deoxy-3 min ,5 min -di-0-acetyl-5- fluorouridine with a benzoyl halide of the formula;
<CHEM>
where hal is a halogen atom and R and n are as before, preferably in the presence of an organic base, particularly triethylamine and a solvent, particularly dioxane.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10895578A JPS5535057A (en) | 1978-09-05 | 1978-09-05 | 2'-deoxy-5-fluorouridine derivative, its preparation, and antitumor agent comprising it |
| EP79301782A EP0009882B1 (en) | 1978-09-05 | 1979-08-31 | 2'-deoxy-5-fluorouridine derivatives, a process for producing the same and antitumor agents comprising the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ATE733T1 true ATE733T1 (en) | 1982-03-15 |
Family
ID=14497883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AT79301782T ATE733T1 (en) | 1978-09-05 | 1979-08-31 | 2'-DEOXY-5-FLUOROURIDINE DERIVATIVES, A PROCESS FOR THEIR PREPARATION AND ANTITUMORS COMPOSITIONS CONTAINING THEM. |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US4599404A (en) |
| EP (1) | EP0009882B1 (en) |
| JP (1) | JPS5535057A (en) |
| AT (1) | ATE733T1 (en) |
| CA (1) | CA1121811A (en) |
| DE (1) | DE2962235D1 (en) |
| ES (1) | ES483854A1 (en) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5924999B2 (en) * | 1978-06-10 | 1984-06-13 | 富山化学工業株式会社 | Method for producing a novel 5-fluoro-2'-deoxy-β-uridine derivative |
| GB2072164B (en) * | 1980-02-15 | 1983-12-21 | Funai Pharmaceutical Ind Ltd | 2'-deoxy-3',5'-di-o-alkylcarbonyl-5-fluorouridine derivatives a process for the preparation of the derivatives and antitumor agents containing the derivatives |
| EP0082668A1 (en) * | 1981-12-18 | 1983-06-29 | Beecham Group Plc | 5-(2-Halogenovinyl)-2'-deoxyuridine derivatives, processes for their preparation, pharmaceutical compositions containing them and their use in treating viral infections |
| JPS6041924A (en) * | 1984-07-17 | 1985-03-05 | 松下電器産業株式会社 | beverage making machine |
| JPS6041922A (en) * | 1984-07-17 | 1985-03-05 | 松下電器産業株式会社 | Beverage maker |
| EP0436902B1 (en) * | 1984-10-30 | 1995-06-28 | Otsuka Pharmaceutical Co., Ltd. | 5-Fluorouracil derivatives |
| US4864021A (en) * | 1984-10-30 | 1989-09-05 | Otsuka Pharmaceutical Co., Ltd. | 5-fluorouracil derivatives |
| JPH0678478B2 (en) * | 1986-03-19 | 1994-10-05 | ユニチカ株式会社 | Thermoplastic resin composition |
| DE3786834T2 (en) * | 1986-04-30 | 1994-03-03 | Otsuka Pharma Co Ltd | 5-fluoro-uracil derivatives. |
| AU610913B2 (en) * | 1987-07-31 | 1991-05-30 | Taiho Pharmaceutical Co., Ltd. | 2'-deoxy-5-fluorouridine derivatives |
| US4992534A (en) * | 1987-08-12 | 1991-02-12 | Otsuka Pharmaceutical Co., Ltd. | 3'-O-,5'-O-derivatives of 2'-deoxy-5-fluorouridine |
| US4981908A (en) * | 1988-02-02 | 1991-01-01 | E. I. Du Pont De Nemours And Company | Thermoplastic elastomer blends |
| AU610344B2 (en) * | 1988-02-29 | 1991-05-16 | Taiho Pharmaceutical Co., Ltd. | 2'-deoxy-5-fluorouridine derivatives |
| US7160537B2 (en) * | 2003-12-15 | 2007-01-09 | Siemens Medical Solutions Usa, Inc. | Method for preparing radiolabeled thymidine having low chromophoric byproducts |
| US20050131224A1 (en) * | 2003-12-15 | 2005-06-16 | Cti Pet Systems, Inc. | Method for preparing radiolabeled thymidine |
| CN113234064B (en) * | 2021-05-27 | 2022-03-29 | 西南医科大学附属中医医院 | Tegafur derivative and preparation method and application thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3168513A (en) * | 1962-03-02 | 1965-02-02 | Hoffmann La Roche | Derivative of 2'-deoxy-5-fluorouridine |
| US3309359A (en) * | 1965-10-22 | 1967-03-14 | Hoffmann La Roche | N-mono-acyl-5-fluorocytosine derivatives and process |
| US3975367A (en) * | 1971-06-08 | 1976-08-17 | The Upjohn Company | Arabinofuranosyl N4 -aminoacyl cytosine containing compounds |
| FR2306701A1 (en) * | 1975-04-08 | 1976-11-05 | Asahi Chemical Ind | DERIVATIVES OF NUCLEOTIDES |
| DE2658672A1 (en) * | 1976-12-23 | 1978-06-29 | Robugen Gmbh | Virustatic deoxy-uridine ether(s) - effective against RNA viruses, esp. 5-O-trityl-5-ethyl-2-deoxy-uridine |
-
1978
- 1978-09-05 JP JP10895578A patent/JPS5535057A/en active Granted
-
1979
- 1979-08-21 US US06/068,340 patent/US4599404A/en not_active Expired - Lifetime
- 1979-08-31 AT AT79301782T patent/ATE733T1/en not_active IP Right Cessation
- 1979-08-31 DE DE7979301782T patent/DE2962235D1/en not_active Expired
- 1979-08-31 EP EP79301782A patent/EP0009882B1/en not_active Expired
- 1979-09-03 ES ES483854A patent/ES483854A1/en not_active Expired
- 1979-09-04 CA CA000334975A patent/CA1121811A/en not_active Expired
-
1982
- 1982-09-16 US US06/419,014 patent/US4490366A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US4490366A (en) | 1984-12-25 |
| EP0009882B1 (en) | 1982-03-03 |
| DE2962235D1 (en) | 1982-04-01 |
| US4599404A (en) | 1986-07-08 |
| JPS5535057A (en) | 1980-03-11 |
| CA1121811A (en) | 1982-04-13 |
| JPS5611718B2 (en) | 1981-03-16 |
| ES483854A1 (en) | 1980-09-01 |
| EP0009882A1 (en) | 1980-04-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| UEP | Publication of translation of european patent specification | ||
| REN | Ceased due to non-payment of the annual fee |