DE2234881A1 - Verfahren zur vorbereitung von 1-beta-d-arabinofuranosylzytosin - Google Patents
Verfahren zur vorbereitung von 1-beta-d-arabinofuranosylzytosinInfo
- Publication number
- DE2234881A1 DE2234881A1 DE19722234881 DE2234881A DE2234881A1 DE 2234881 A1 DE2234881 A1 DE 2234881A1 DE 19722234881 DE19722234881 DE 19722234881 DE 2234881 A DE2234881 A DE 2234881A DE 2234881 A1 DE2234881 A1 DE 2234881A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction
- preparation
- arabinofuranosylcytosine
- procedure
- cytidine
- 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
- 238000000034 method Methods 0.000 title claims description 13
- UHDGCWIWMRVCDJ-UHFFFAOYSA-N 1-beta-D-Xylofuranosyl-NH-Cytosine Natural products O=C1N=C(N)C=CN1C1C(O)C(O)C(CO)O1 UHDGCWIWMRVCDJ-UHFFFAOYSA-N 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 6
- UHDGCWIWMRVCDJ-CCXZUQQUSA-N Cytarabine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 UHDGCWIWMRVCDJ-CCXZUQQUSA-N 0.000 title description 11
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- UHDGCWIWMRVCDJ-PSQAKQOGSA-N Cytidine Natural products O=C1N=C(N)C=CN1[C@@H]1[C@@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-PSQAKQOGSA-N 0.000 claims description 6
- UHDGCWIWMRVCDJ-ZAKLUEHWSA-N cytidine Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O1 UHDGCWIWMRVCDJ-ZAKLUEHWSA-N 0.000 claims description 6
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 6
- 159000000011 group IA salts Chemical class 0.000 claims description 5
- 238000002425 crystallisation Methods 0.000 claims description 4
- 230000008025 crystallization Effects 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- 239000012736 aqueous medium Substances 0.000 claims description 2
- 239000002609 medium Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 150000005676 cyclic carbonates Chemical class 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000013074 reference sample Substances 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- RKSLVDIXBGWPIS-MNCSTQPFSA-N 1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-iodopyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 RKSLVDIXBGWPIS-MNCSTQPFSA-N 0.000 description 1
- STRZQWQNZQMHQR-MNCSTQPFSA-N 4-amino-1-[(2r,3s,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoropyrimidin-2-one Chemical compound C1=C(F)C(N)=NC(=O)N1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 STRZQWQNZQMHQR-MNCSTQPFSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
- 230000002155 anti-virotic effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000003327 cancerostatic effect Effects 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960004413 flucytosine Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- HQRPHMAXFVUBJX-UHFFFAOYSA-M lithium;hydrogen carbonate Chemical compound [Li+].OC([O-])=O HQRPHMAXFVUBJX-UHFFFAOYSA-M 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- 125000003835 nucleoside group Chemical class 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent 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
- C07H19/06—Pyrimidine 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)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS708471A CS164401B1 (en) | 1971-10-07 | 1971-10-07 | Method of 1-beta-d-arabinofuranosylcytosine's preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2234881A1 true DE2234881A1 (de) | 1973-04-12 |
Family
ID=5419302
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19722234881 Pending DE2234881A1 (de) | 1971-10-07 | 1972-07-15 | Verfahren zur vorbereitung von 1-beta-d-arabinofuranosylzytosin |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS4844271A (enrdf_load_stackoverflow) |
| AU (1) | AU458692B2 (enrdf_load_stackoverflow) |
| CA (1) | CA952901A (enrdf_load_stackoverflow) |
| CS (1) | CS164401B1 (enrdf_load_stackoverflow) |
| DE (1) | DE2234881A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1378408A (enrdf_load_stackoverflow) |
| HU (1) | HU165019B (enrdf_load_stackoverflow) |
| SU (1) | SU456808A1 (enrdf_load_stackoverflow) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4924676A (enrdf_load_stackoverflow) * | 1972-06-30 | 1974-03-05 | ||
| JPS55165627A (en) * | 1979-06-09 | 1980-12-24 | Pioneer Electronic Corp | Method for diffusing impurity into semiconductor |
| SE8802687D0 (sv) * | 1988-07-20 | 1988-07-20 | Astra Ab | Nucleoside derivatives |
| US5559101A (en) * | 1994-10-24 | 1996-09-24 | Genencor International, Inc. | L-ribofuranosyl nucleosides |
| EP0788507B1 (en) * | 1994-10-24 | 2004-12-15 | Genencor International, Inc. | L-pyranosyl nucleosides |
-
1971
- 1971-10-07 CS CS708471A patent/CS164401B1/cs unknown
-
1972
- 1972-07-05 AU AU44242/72A patent/AU458692B2/en not_active Expired
- 1972-07-15 DE DE19722234881 patent/DE2234881A1/de active Pending
- 1972-07-19 GB GB3373072A patent/GB1378408A/en not_active Expired
- 1972-08-04 CA CA148,838A patent/CA952901A/en not_active Expired
- 1972-10-05 HU HUCE000899 patent/HU165019B/hu unknown
- 1972-10-06 SU SU1840153A patent/SU456808A1/ru active
- 1972-10-07 JP JP10033372A patent/JPS4844271A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| GB1378408A (en) | 1974-12-27 |
| SU456808A1 (ru) | 1975-01-15 |
| AU4424272A (en) | 1974-01-10 |
| CA952901A (en) | 1974-08-13 |
| CS164401B1 (en) | 1975-11-07 |
| JPS4844271A (enrdf_load_stackoverflow) | 1973-06-26 |
| AU458692B2 (en) | 1975-03-06 |
| HU165019B (enrdf_load_stackoverflow) | 1974-06-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |