JPS6256491A - 高純度メチルコバラミンの製造法 - Google Patents
高純度メチルコバラミンの製造法Info
- Publication number
- JPS6256491A JPS6256491A JP19602085A JP19602085A JPS6256491A JP S6256491 A JPS6256491 A JP S6256491A JP 19602085 A JP19602085 A JP 19602085A JP 19602085 A JP19602085 A JP 19602085A JP S6256491 A JPS6256491 A JP S6256491A
- Authority
- JP
- Japan
- Prior art keywords
- lower aliphatic
- methylcobalamin
- water
- reaction mixture
- adsorbed substance
- 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.)
- Granted
Links
- JEWJRMKHSMTXPP-BYFNXCQMSA-M methylcobalamin Chemical compound C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O JEWJRMKHSMTXPP-BYFNXCQMSA-M 0.000 title claims abstract description 33
- 235000007672 methylcobalamin Nutrition 0.000 title claims abstract description 33
- 239000011585 methylcobalamin Substances 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 7
- RMRCNWBMXRMIRW-BYFNXCQMSA-M cyanocobalamin Chemical compound N#C[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O RMRCNWBMXRMIRW-BYFNXCQMSA-M 0.000 claims abstract description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 22
- 238000000034 method Methods 0.000 claims abstract description 19
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims abstract description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 15
- 235000000639 cyanocobalamin Nutrition 0.000 claims abstract description 15
- 239000011666 cyanocobalamin Substances 0.000 claims abstract description 15
- 229960002104 cyanocobalamin Drugs 0.000 claims abstract description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000011541 reaction mixture Substances 0.000 claims abstract description 12
- 239000000741 silica gel Substances 0.000 claims abstract description 6
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 6
- 238000007796 conventional method Methods 0.000 claims abstract description 5
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000001179 sorption measurement Methods 0.000 claims description 8
- 239000003463 adsorbent Substances 0.000 claims description 5
- 238000004587 chromatography analysis Methods 0.000 claims description 5
- 229920006026 co-polymeric resin Polymers 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- 239000013078 crystal Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 9
- 238000007069 methylation reaction Methods 0.000 abstract description 3
- 229920001577 copolymer Polymers 0.000 abstract description 2
- 230000001035 methylating effect Effects 0.000 abstract description 2
- 208000033808 peripheral neuropathy Diseases 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 230000011987 methylation Effects 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 235000002639 sodium chloride Nutrition 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 239000013076 target substance Substances 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 239000002156 adsorbate Substances 0.000 description 4
- -1 aliphatic alcohols Chemical class 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- YOZNUFWCRFCGIH-BYFNXCQMSA-L hydroxocobalamin Chemical compound O[Co+]N([C@]1([H])[C@H](CC(N)=O)[C@]\2(CCC(=O)NC[C@H](C)OP(O)(=O)OC3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)C)C/2=C(C)\C([C@H](C/2(C)C)CCC(N)=O)=N\C\2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O YOZNUFWCRFCGIH-BYFNXCQMSA-L 0.000 description 4
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000004867 hydroxocobalamin Nutrition 0.000 description 2
- 239000011704 hydroxocobalamin Substances 0.000 description 2
- 229960001103 hydroxocobalamin Drugs 0.000 description 2
- DQOCFCZRZOAIBN-WZHZPDAFSA-L hydroxycobalamin Chemical compound O.[Co+2].[N-]([C@@H]1[C@H](CC(N)=O)[C@@]2(C)CCC(=O)NC[C@@H](C)OP([O-])(=O)O[C@H]3[C@H]([C@H](O[C@@H]3CO)N3C4=CC(C)=C(C)C=C4N=C3)O)\C2=C(C)/C([C@H](C\2(C)C)CCC(N)=O)=N/C/2=C\C([C@H]([C@@]/2(CC(N)=O)C)CCC(N)=O)=N\C\2=C(C)/C2=N[C@]1(C)[C@@](C)(CC(N)=O)[C@@H]2CCC(N)=O DQOCFCZRZOAIBN-WZHZPDAFSA-L 0.000 description 2
- 230000002452 interceptive effect Effects 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 208000032131 Diabetic Neuropathies Diseases 0.000 description 1
- 206010029240 Neuritis Diseases 0.000 description 1
- 206010036105 Polyneuropathy Diseases 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 108091006629 SLC13A2 Proteins 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000001175 cerebrospinal fluid Anatomy 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000005515 coenzyme Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 208000027232 peripheral nervous system disease Diseases 0.000 description 1
- 208000019629 polyneuritis Diseases 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 230000022558 protein metabolic process Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19602085A JPS6256491A (ja) | 1985-09-06 | 1985-09-06 | 高純度メチルコバラミンの製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP19602085A JPS6256491A (ja) | 1985-09-06 | 1985-09-06 | 高純度メチルコバラミンの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6256491A true JPS6256491A (ja) | 1987-03-12 |
| JPH0572920B2 JPH0572920B2 (enrdf_load_stackoverflow) | 1993-10-13 |
Family
ID=16350883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP19602085A Granted JPS6256491A (ja) | 1985-09-06 | 1985-09-06 | 高純度メチルコバラミンの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6256491A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801647A (zh) * | 2016-04-17 | 2016-07-27 | 张春燕 | 甲钴胺化合物及含其制剂与制备方法 |
-
1985
- 1985-09-06 JP JP19602085A patent/JPS6256491A/ja active Granted
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105801647A (zh) * | 2016-04-17 | 2016-07-27 | 张春燕 | 甲钴胺化合物及含其制剂与制备方法 |
| CN105801647B (zh) * | 2016-04-17 | 2018-08-17 | 张春燕 | 甲钴胺化合物及含其制剂与制备方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0572920B2 (enrdf_load_stackoverflow) | 1993-10-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |