JPS6335639B2 - - Google Patents
Info
- Publication number
- JPS6335639B2 JPS6335639B2 JP11468086A JP11468086A JPS6335639B2 JP S6335639 B2 JPS6335639 B2 JP S6335639B2 JP 11468086 A JP11468086 A JP 11468086A JP 11468086 A JP11468086 A JP 11468086A JP S6335639 B2 JPS6335639 B2 JP S6335639B2
- Authority
- JP
- Japan
- Prior art keywords
- alacitidine
- stearyl phosphate
- sodium salt
- water
- stearyl
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 229910019142 PO4 Inorganic materials 0.000 claims description 13
- 239000010452 phosphate Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 6
- 159000000000 sodium salts Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 4
- UHGIMQLJWRAPLT-UHFFFAOYSA-N octadecyl dihydrogen phosphate Chemical compound CCCCCCCCCCCCCCCCCCOP(O)(O)=O UHGIMQLJWRAPLT-UHFFFAOYSA-N 0.000 claims description 3
- QSNURPAXNFOIOV-FKLBCBSKSA-N 4-azanyl-1-[(2r,3s,4s,5r)-5-(hydroxymethyl)-3,4-bis(oxidanyl)oxolan-2-yl]pyrimidin-2-one Chemical compound O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1.O=C1N=C(N)C=CN1[C@H]1[C@@H](O)[C@H](O)[C@@H](CO)O1 QSNURPAXNFOIOV-FKLBCBSKSA-N 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 239000000047 product Substances 0.000 description 11
- 239000000243 solution Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000003125 aqueous solvent Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000004811 liquid chromatography Methods 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 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 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000010979 pH adjustment Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 230000009876 antimalignant effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- -1 concentrated Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- MVFPQYVAVMINHP-UHFFFAOYSA-L disodium;octadecyl phosphate Chemical compound [Na+].[Na+].CCCCCCCCCCCCCCCCCCOP([O-])([O-])=O MVFPQYVAVMINHP-UHFFFAOYSA-L 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61114680A JPS62273993A (ja) | 1986-05-21 | 1986-05-21 | １−β−Ｄ−アラビノフラノシルシトシン−５′−ステアリルりん酸ナトリウム塩の新規製造法 |
| EP87104071A EP0239015B1 (en) | 1986-03-24 | 1987-03-19 | Process for producing 1-beta-d-arabinofuranosylcytosine-5'-stearylphosphate monosodium salt and monohydrate thereof, and pharmaceutical composition containing the latter |
| DE8787104071T DE3773716D1 (de) | 1986-03-24 | 1987-03-19 | Verfahren zur herstellung von monosodiumsalz und dessen monohydrat von 1-beta-d-arabinofuranosylcytosin-5'stearylphosphat und diese enthaltende pharmazeutische zusammensetzung. |
| ES198787104071T ES2031462T3 (es) | 1986-03-24 | 1987-03-19 | Procedimiento para producir 1-b-d-arabinofuranosilcitosina-5'-estearilfosfato monosodico y monohidrato de la misma, y compuesto farmaceutico que contiene esta ultima. |
| CA000532597A CA1270820A (en) | 1986-03-24 | 1987-03-20 | PROCESS FOR PRODUCING 1-.beta.-D- ARABINOFURANOSYLCYTOSINE-5'-STEARYLPHOSPHATE MONOSODIUM SALT AND MONOHYDRATE THEREOF |
| AU70475/87A AU592165B2 (en) | 1986-03-24 | 1987-03-20 | Process for producing 1-beta-D-arabinofuranosylcytosine-5- stearylphosphate monosodium salt and monohydrate thereof |
| HU871247A HU196429B (en) | 1986-03-24 | 1987-03-20 | Process for preparing monosodium salts of 1-beta-d-arabinofuranozylcytozine-5'-stearyl phosphate and the monohydrate of this salt |
| KR1019870002697A KR910008801B1 (ko) | 1986-03-24 | 1987-03-23 | 1-β-D-아라비노푸라노실시토신-5′-스테아릴포스페이트 모노나트륨염 |
| US07/028,951 US4812560A (en) | 1986-03-24 | 1987-03-23 | Process for producing 1-β-D-arabinofuranosylcytosine-5'-stearylphosphate monosodium salt and monohydrate thereof |
| US07/399,303 US5049663A (en) | 1986-03-24 | 1989-08-25 | Process for producing 1-β-D-arabinofuranosylcytosine-5'-stearylphosphate monosodium salt and monohydrate thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61114680A JPS62273993A (ja) | 1986-05-21 | 1986-05-21 | １−β−Ｄ−アラビノフラノシルシトシン−５′−ステアリルりん酸ナトリウム塩の新規製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62273993A JPS62273993A (ja) | 1987-11-28 |
| JPS6335639B2 true JPS6335639B2 (enrdf_load_stackoverflow) | 1988-07-15 |
Family
ID=14643944
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61114680A Granted JPS62273993A (ja) | 1986-03-24 | 1986-05-21 | １−β−Ｄ−アラビノフラノシルシトシン−５′−ステアリルりん酸ナトリウム塩の新規製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62273993A (enrdf_load_stackoverflow) |
-
1986
- 1986-05-21 JP JP61114680A patent/JPS62273993A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS62273993A (ja) | 1987-11-28 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |