CN101020707A - Process of refining calcium dibutyryl adenosine cyclophosphate - Google Patents
Process of refining calcium dibutyryl adenosine cyclophosphate Download PDFInfo
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- CN101020707A CN101020707A CN 200610155045 CN200610155045A CN101020707A CN 101020707 A CN101020707 A CN 101020707A CN 200610155045 CN200610155045 CN 200610155045 CN 200610155045 A CN200610155045 A CN 200610155045A CN 101020707 A CN101020707 A CN 101020707A
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- CN
- China
- Prior art keywords
- ate
- calcium
- dibutyryladenosine cyclophosph
- calcium dibutyryladenosine
- acetone
- Prior art date
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- RCFZVVHQICKFQW-NGVPHMJWSA-L calcium;[(4ar,6r,7r,7ar)-6-[6-(butanoylamino)purin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate Chemical compound [Ca+2].C([C@H]1O2)OP([O-])(=O)O[C@H]1[C@@H](OC(=O)CCC)[C@@H]2N1C(N=CN=C2NC(=O)CCC)=C2N=C1.C([C@H]1O2)OP([O-])(=O)O[C@H]1[C@@H](OC(=O)CCC)[C@@H]2N1C(N=CN=C2NC(=O)CCC)=C2N=C1 RCFZVVHQICKFQW-NGVPHMJWSA-L 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims abstract description 13
- 238000007670 refining Methods 0.000 title abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 42
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000843 powder Substances 0.000 claims abstract description 5
- 239000007788 liquid Substances 0.000 claims abstract description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 24
- 239000012043 crude product Substances 0.000 claims description 14
- 238000000746 purification Methods 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 2
- 239000000047 product Substances 0.000 abstract description 5
- 238000003756 stirring Methods 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- YBPWNFMPWVRSOD-QDEZUTFSSA-N 5-[(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]-5-hydroxynonane-4,6-dione Chemical compound C(CCC)(=O)C([C@@H]1[C@H]([C@H]([C@@H](O1)N1C=NC=2C(N)=NC=NC1=2)O)O)(O)C(CCC)=O YBPWNFMPWVRSOD-QDEZUTFSSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- CJGYSWNGNKCJSB-YVLZZHOMSA-M [(4ar,6r,7r,7ar)-6-[6-(butanoylamino)purin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4h-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate Chemical compound C([C@H]1O2)OP([O-])(=O)O[C@H]1[C@@H](OC(=O)CCC)[C@@H]2N1C(N=CN=C2NC(=O)CCC)=C2N=C1 CJGYSWNGNKCJSB-YVLZZHOMSA-M 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001412 amines Chemical group 0.000 description 1
- YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
The present invention relates to process of refining calcium dibutyryl adenosine cyclophosphate, and aims at obtaining calcium dibutyryl adenosine cyclophosphate product with high content. The process of refining calcium dibutyryl adenosine cyclophosphate features that methanol and acetone are added into coarse calcium dibutyryl adenosine cyclophosphate product through full stirring, the liquid part is separated out and calcium dibutyryl adenosine cyclophosphate powder with calcium dibutyryl adenosine cyclophosphate content over 98 % is obtained. Where, the volume ratio of coarse calcium dibutyryl adenosine cyclophosphate product, methanol and acetone is 1 to 0.1-8 to 0.5-12.
Description
Technical field
The present invention relates to a kind of pharmaceutical product, specifically is a kind of process for purification of Calcium Dibutyryladenosine Cyclophosph-ate.
Background technology
A kind of preparation method of Calcium Dibutyryladenosine Cyclophosph-ate is disclosed among the Chinese patent literature CN1554358A " Calcium Dibutyryladenosine Cyclophosph-ate preparation and preparation method ".
(1) preparation quaternary amine: cAMP adds triethylamine makes it dissolving, add then anhydrous pyridine again 30～70 ℃ of decompressions take out pyridine, dry cAMP triethylamine salt;
(2) acidylate-hydrolysis: get the cAMP triethylamine salt, add anhydrous pyridine and butanoic anhydride, lucifuge reaction 4～10 days, treat complete acylation reaction after, take out reaction solution, add distilled water, hydrolysis 2～3 hours, concentrating under reduced pressure then, dibutyryl adenosine cyclophosphate;
(3) become calcium salt: after adding Calcium Chloride Powder Anhydrous and the abundant mixing of Calcium Dibutyryladenosine Cyclophosph-ate, be concentrated into driedly, with the anhydrous diethyl ether washing, drying must Calcium Dibutyryladenosine Cyclophosph-ate.
" up-to-date biochemical drug technology of preparing " (Chinese Medicine science and technology press first version in March calendar year 2001) 246-248 page or leaf discloses a kind of to be the chemical synthesis of the preparation calcium dibutyryl cyclic AMP of raw material with cAMP, to disclose whole technological process especially in detail.
But the product Calcium Dibutyryladenosine Cyclophosph-ate content of above-mentioned technology generally is no more than 95%, is still waiting to improve.
Summary of the invention
The technical problem that the present invention solves is to obtain the higher product of Calcium Dibutyryladenosine Cyclophosph-ate content.
The process for purification of Calcium Dibutyryladenosine Cyclophosph-ate of the present invention is characterized in that in the Calcium Dibutyryladenosine Cyclophosph-ate crude product, adds methyl alcohol and acetone and fully mixes thoroughly, and the separating liquid part obtains the dry powder of Calcium Dibutyryladenosine Cyclophosph-ate content 〉=98%; Calcium Dibutyryladenosine Cyclophosph-ate crude product weight wherein: methyl alcohol volume: the feed ratio of acetone volume=1: 0.1～8: 0.5～12.Described Calcium Dibutyryladenosine Cyclophosph-ate crude product is a Calcium Dibutyryladenosine Cyclophosph-ate alleged in the background technology.Described separation, conventional process such as comprise precipitation, extract, drain.
Above-mentioned weightmeasurement ratio, promptly Calcium Dibutyryladenosine Cyclophosph-ate crude product weight unit is kg (or g), then the volume unit of liquid such as methyl alcohol, acetone, ether should be L (or ml) mutually, in full together.
As preferably, add methyl alcohol and acetone after, add ether again and fully mix thoroughly; Calcium Dibutyryladenosine Cyclophosph-ate crude product weight wherein: the feed ratio of ether volume=1: 2～30, its better effects if.This is because the solubleness of Calcium Dibutyryladenosine Cyclophosph-ate in ether is littler, makes the yield of elaboration higher.
The most preferred, Calcium Dibutyryladenosine Cyclophosph-ate crude product weight: methyl alcohol volume: acetone volume: the feed ratio of ether volume=1: 1.5: 2: 5.
If it is the Calcium Dibutyryladenosine Cyclophosph-ate crude product is crushed to 20～80 orders in advance, then can effect better.
Studies have shown that, use methyl alcohol or acetone separately, the effect that improves Calcium Dibutyryladenosine Cyclophosph-ate content is also arranged.
The present invention has characteristics simple for process, and Calcium Dibutyryladenosine Cyclophosph-ate content can reach more than 98%.
Embodiment
Below by embodiment, technical scheme of the present invention is described in further detail.
Embodiment 1.Claim the Calcium Dibutyryladenosine Cyclophosph-ate crude product of 1000g, and be milled to about 40 orders, add in the mixed solution of 333ml methyl alcohol and 3700ml acetone, stirred 0.5 hour that drain, the 1000ml that adds diethyl ether again drains, repeat above operation, till obtaining qualified dry powder.
Embodiment 2-5.
| Calcium Dibutyryladenosine Cyclophosph-ate crude product (g) | Methyl alcohol (ml) | Acetone (ml) | Ether (ml) | Calcium Dibutyryladenosine Cyclophosph-ate content % | |
| Embodiment 2 | 100 | 50 | 50 | 200 | 98.0 |
| Embodiment 3 | 100 | 800 | 200 | 3000 | 98.1 |
| Embodiment 4 | 100 | 150 | 200 | 500 | 98.3 |
| Embodiment 5 | 100 | 100 | 1200 | 1000 | 98.1 |
| Embodiment 6 | 100 | 33.3 | 370 | Do not add | 98.0 |
| Embodiment 7 | 100 | 10 | 120 | Do not add | 98.0 |
Claims (4)
1, a kind of process for purification of Calcium Dibutyryladenosine Cyclophosph-ate is characterized in that in the Calcium Dibutyryladenosine Cyclophosph-ate crude product, adds methyl alcohol and acetone and fully mixes thoroughly, and the separating liquid part obtains the dry powder of Calcium Dibutyryladenosine Cyclophosph-ate content 〉=98%; Calcium Dibutyryladenosine Cyclophosph-ate crude product weight wherein: methyl alcohol volume: the feed ratio of acetone volume=1: 0.1～8: 0.5～12.
2, the process for purification of Calcium Dibutyryladenosine Cyclophosph-ate according to claim 1, its feature add ether again and fully mix thoroughly after adding methyl alcohol and acetone; Calcium Dibutyryladenosine Cyclophosph-ate crude product weight wherein: the feed ratio of ether volume=1: 2～30.
3, the process for purification of Calcium Dibutyryladenosine Cyclophosph-ate according to claim 2 is characterized in that Calcium Dibutyryladenosine Cyclophosph-ate crude product weight: the methyl alcohol volume: the acetone volume: the feed ratio of ether volume=1: 1.5: 2: 5.
4,, it is characterized in that described Calcium Dibutyryladenosine Cyclophosph-ate crude product is crushed to 20～80 orders earlier according to the process for purification of claim 1 or 2 or 3 described Calcium Dibutyryladenosine Cyclophosph-ate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101550451A CN100457770C (en) | 2006-12-06 | 2006-12-06 | Process of refining calcium dibutyryl adenosine cyclophosphate |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB2006101550451A CN100457770C (en) | 2006-12-06 | 2006-12-06 | Process of refining calcium dibutyryl adenosine cyclophosphate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101020707A true CN101020707A (en) | 2007-08-22 |
| CN100457770C CN100457770C (en) | 2009-02-04 |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242403A (en) * | 2012-06-21 | 2013-08-14 | 辽宁亿灵科创生物医药科技有限公司 | High-purity dibutyryladenosine cyclophosphate calcium and preparation method thereof |
| CN104262436A (en) * | 2014-09-19 | 2015-01-07 | 北京赛盟医药科技发展有限公司 | Amorphous calcium bucladesine sterile powder |
| CN104478979A (en) * | 2014-12-24 | 2015-04-01 | 上海第一生化药业有限公司 | Crystal water-free calcium dibutyryladenosine cyclophosphate crystal form, as well as preparation method and application thereof |
| CN104490798A (en) * | 2014-12-24 | 2015-04-08 | 上海第一生化药业有限公司 | Crystal water-free calcium dibutyryladenosine cyclophosphate crystal form freeze-dried powder injection and preparation method thereof |
| CN105566423A (en) * | 2014-10-17 | 2016-05-11 | 上海紫源制药有限公司 | Method for purifying calcium dibutyryladenosine cyclophosphate |
| CN108997430A (en) * | 2018-07-16 | 2018-12-14 | 南京工业大学 | A kind of crystal of Calcium Dibutyryladenosine Cyclophosph-ate salt |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5152079Y2 (en) * | 1971-05-31 | 1976-12-13 | ||
| JPS6035354B2 (en) * | 1975-02-14 | 1985-08-14 | 第一製薬株式会社 | Method for obtaining nucleotide derivatives |
| JPS6024118B2 (en) * | 1975-03-31 | 1985-06-11 | 第一製薬株式会社 | Process for producing adenosine phosphate derivatives |
| JPS58194895A (en) * | 1982-05-10 | 1983-11-12 | Dai Ichi Seiyaku Co Ltd | Improved method for preparing na salt of dbc-amp (n6,2'-o-dibutyryladenosine-3,5'-cyclic phosphate) |
| CN1554358A (en) * | 2003-12-23 | 2004-12-15 | 上海第一生化药业有限公司 | Dibutyryl cyclic adenosine monophosphate preparation and preparing method |
-
2006
- 2006-12-06 CN CNB2006101550451A patent/CN100457770C/en active Active
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103242403A (en) * | 2012-06-21 | 2013-08-14 | 辽宁亿灵科创生物医药科技有限公司 | High-purity dibutyryladenosine cyclophosphate calcium and preparation method thereof |
| CN103242403B (en) * | 2012-06-21 | 2016-01-20 | 北京赛盟医药科技发展有限公司 | High-purity dibutyryladenosine cyclophosphate calcium and preparation method thereof |
| CN104262436A (en) * | 2014-09-19 | 2015-01-07 | 北京赛盟医药科技发展有限公司 | Amorphous calcium bucladesine sterile powder |
| CN105566423A (en) * | 2014-10-17 | 2016-05-11 | 上海紫源制药有限公司 | Method for purifying calcium dibutyryladenosine cyclophosphate |
| CN104478979A (en) * | 2014-12-24 | 2015-04-01 | 上海第一生化药业有限公司 | Crystal water-free calcium dibutyryladenosine cyclophosphate crystal form, as well as preparation method and application thereof |
| CN104490798A (en) * | 2014-12-24 | 2015-04-08 | 上海第一生化药业有限公司 | Crystal water-free calcium dibutyryladenosine cyclophosphate crystal form freeze-dried powder injection and preparation method thereof |
| CN104490798B (en) * | 2014-12-24 | 2018-05-11 | 上海第一生化药业有限公司 | Nodeless mesh water Calcium Dibutyryladenosine Cyclophosph-ate crystal form freeze-dried powder and preparation method thereof |
| US10420787B2 (en) | 2014-12-24 | 2019-09-24 | Sph No.1 Biochemical & Pharmaceutical Co., Ltd. | Crystal-water-free calcium dibutyryladenosine cyclophosphate crystal form and preparation method and application thereof |
| CN108997430A (en) * | 2018-07-16 | 2018-12-14 | 南京工业大学 | A kind of crystal of Calcium Dibutyryladenosine Cyclophosph-ate salt |
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| CN100457770C (en) | 2009-02-04 |
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