DE2152486A1 - Verfahren zur Herstellung von 5'-Desoxy-5'-fluor-6-methyl-mercaptopurinribosid - Google Patents
Verfahren zur Herstellung von 5'-Desoxy-5'-fluor-6-methyl-mercaptopurinribosidInfo
- Publication number
- DE2152486A1 DE2152486A1 DE19712152486 DE2152486A DE2152486A1 DE 2152486 A1 DE2152486 A1 DE 2152486A1 DE 19712152486 DE19712152486 DE 19712152486 DE 2152486 A DE2152486 A DE 2152486A DE 2152486 A1 DE2152486 A1 DE 2152486A1
- Authority
- DE
- Germany
- Prior art keywords
- fluoro
- riboside
- desoxy
- activity
- purine
- 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.)
- Pending
Links
- 230000000694 effects Effects 0.000 title description 3
- UIJIQXGRFSPYQW-UHFFFAOYSA-N 6-methylthiopurine Chemical compound CSC1=NC=NC2=C1N=CN2 UIJIQXGRFSPYQW-UHFFFAOYSA-N 0.000 title description 2
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 4
- 239000012670 alkaline solution Substances 0.000 claims description 2
- 210000004027 cell Anatomy 0.000 abstract description 4
- 210000004881 tumor cell Anatomy 0.000 abstract description 4
- 230000001085 cytostatic effect Effects 0.000 abstract description 3
- 230000006196 deacetylation Effects 0.000 abstract 1
- 238000003381 deacetylation reaction Methods 0.000 abstract 1
- 238000007069 methylation reaction Methods 0.000 abstract 1
- 230000000865 phosphorylative effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZDRFDHHANOYUTE-IOSLPCCCSA-N 6-methylthioinosine Chemical compound C1=NC=2C(SC)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O ZDRFDHHANOYUTE-IOSLPCCCSA-N 0.000 description 8
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 230000006820 DNA synthesis Effects 0.000 description 3
- 230000006819 RNA synthesis Effects 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 230000026731 phosphorylation Effects 0.000 description 3
- 238000006366 phosphorylation reaction Methods 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 208000003468 Ehrlich Tumor Carcinoma Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 230000003327 cancerostatic effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000824 cytostatic agent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 229960001428 mercaptopurine Drugs 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000035755 proliferation Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000008223 ribosides Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 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
- C07H19/16—Purine radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD15141270 | 1970-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2152486A1 true DE2152486A1 (de) | 1972-06-29 |
Family
ID=5483172
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712152486 Pending DE2152486A1 (de) | 1970-11-20 | 1971-10-21 | Verfahren zur Herstellung von 5'-Desoxy-5'-fluor-6-methyl-mercaptopurinribosid |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH557821A (enExample) |
| CS (1) | CS156525B2 (enExample) |
| DE (1) | DE2152486A1 (enExample) |
| HU (1) | HU163519B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992001456A1 (en) * | 1990-07-19 | 1992-02-06 | The Wellcome Foundation Limited | Heterocyclic compounds |
-
1971
- 1971-10-21 DE DE19712152486 patent/DE2152486A1/de active Pending
- 1971-11-03 CS CS772371A patent/CS156525B2/cs unknown
- 1971-11-18 CH CH1683171A patent/CH557821A/xx not_active IP Right Cessation
- 1971-11-19 HU HUDE000768 patent/HU163519B/hu unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1992001456A1 (en) * | 1990-07-19 | 1992-02-06 | The Wellcome Foundation Limited | Heterocyclic compounds |
| US5492897A (en) * | 1990-07-19 | 1996-02-20 | Burroughs Wellcome Co. (141) | Method for treating T-cell lymphoblastic leukemia with ara-G nucleoside derivatives |
| JP2873086B2 (ja) | 1990-07-19 | 1999-03-24 | ザ ウエルカム ファウンデーション リミテッド | 複素環化合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| HU163519B (enExample) | 1973-09-27 |
| CS156525B2 (enExample) | 1974-07-24 |
| CH557821A (de) | 1975-01-15 |
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