JPH036153B2 - - Google Patents

Info

Publication number: JPH036153B2
Authority: JP; Japan
Prior art keywords: cobaltichlorophyllin; thiamine; methanol; complex compound; solution
Prior art date: 1988-03-11
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

Application number

JP5624188A

Other languages

English (en)

Japanese (ja)

Other versions

JPS63264483A (ja

Inventor

Taro Takemi

Michiharu Ikoshi

Kazuko Kondo

Toshimitsu Kamei

Toshimitsu Morisue

Tsunekazu Fukushima

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Nisshin Seifun Group Inc

Original Assignee

Nisshin Seifun Group Inc

Priority date (The priority date 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 date listed.)

1988-03-11

Filing date

1988-03-11

Publication date

1991-01-29

1988-03-11 Application filed by Nisshin Seifun Group Inc filed Critical Nisshin Seifun Group Inc

1988-03-11 Priority to JP5624188A priority Critical patent/JPS63264483A/ja

1988-11-01 Publication of JPS63264483A publication Critical patent/JPS63264483A/ja

1991-01-29 Publication of JPH036153B2 publication Critical patent/JPH036153B2/ja

Status Granted legal-status Critical Current

Links

JZRWCGZRTZMZEH-UHFFFAOYSA-N Thiamine Natural products CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N JZRWCGZRTZMZEH-UHFFFAOYSA-N 0.000 claims description 121
235000019157 thiamine Nutrition 0.000 claims description 63
239000011721 thiamine Substances 0.000 claims description 63
229960003495 thiamine Drugs 0.000 claims description 59
150000001875 compounds Chemical class 0.000 claims description 47
229940099898 chlorophyllin Drugs 0.000 claims description 23
235000019805 chlorophyllin Nutrition 0.000 claims description 23
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 14
229920000642 polymer Polymers 0.000 claims description 14
SURLGNKAQXKNSP-DBLYXWCISA-N chlorin Chemical compound C\1=C/2\N/C(=C\C3=N/C(=C\C=4NC(/C=C\5/C=CC/1=N/5)=CC=4)/C=C3)/CC\2 SURLGNKAQXKNSP-DBLYXWCISA-N 0.000 claims description 12
230000002209 hydrophobic effect Effects 0.000 claims description 9
239000002904 solvent Substances 0.000 claims description 9
150000001868 cobalt Chemical class 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
238000004587 chromatography analysis Methods 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
239000011541 reaction mixture Substances 0.000 claims description 3
WXASNDZTGYYQHX-UHFFFAOYSA-L 18-(2-carboxylatoethyl)-20-(carboxylatomethyl)-12-ethenyl-7-ethyl-3,8,13,17-tetramethyl-17,18-dihydroporphyrin-21,23-diide-2-carboxylate;cobalt(2+);hydron Chemical compound [H+].[H+].[H+].[Co+2].C1=C([N-]2)C(CC)=C(C)C2=CC(C(=C2C)C=C)=NC2=CC(C(C2CCC([O-])=O)C)=NC2=C(CC([O-])=O)C2=NC1=C(C)C2=C([O-])[O-] WXASNDZTGYYQHX-UHFFFAOYSA-L 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
KYMBYSLLVAOCFI-UHFFFAOYSA-N thiamine Chemical compound CC1=C(CCO)SCN1CC1=CN=C(C)N=C1N KYMBYSLLVAOCFI-UHFFFAOYSA-N 0.000 claims 3
238000002523 gelfiltration Methods 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 186
239000000243 solution Substances 0.000 description 23
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
238000010521 absorption reaction Methods 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 15
238000000862 absorption spectrum Methods 0.000 description 14
238000000034 method Methods 0.000 description 14
239000000843 powder Substances 0.000 description 9
239000000047 product Substances 0.000 description 8
239000002994 raw material Substances 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 7
239000000126 substance Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 6
239000007788 liquid Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
239000012488 sample solution Substances 0.000 description 6
235000011121 sodium hydroxide Nutrition 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
239000007795 chemical reaction product Substances 0.000 description 5
229910017052 cobalt Inorganic materials 0.000 description 5
239000010941 cobalt Substances 0.000 description 5
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
208000025865 Ulcer Diseases 0.000 description 4
150000003544 thiamines Chemical class 0.000 description 4
231100000397 ulcer Toxicity 0.000 description 4
FUFLCEKSBBHCMO-UHFFFAOYSA-N 11-dehydrocorticosterone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)C(=O)CO)C4C3CCC2=C1 FUFLCEKSBBHCMO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
MFYSYFVPBJMHGN-ZPOLXVRWSA-N Cortisone Chemical compound O=C1CC[C@]2(C)[C@H]3C(=O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 MFYSYFVPBJMHGN-ZPOLXVRWSA-N 0.000 description 3
MFYSYFVPBJMHGN-UHFFFAOYSA-N Cortisone Natural products O=C1CCC2(C)C3C(=O)CC(C)(C(CC4)(O)C(=O)CO)C4C3CCC2=C1 MFYSYFVPBJMHGN-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
241000196324 Embryophyta Species 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
229940011182 cobalt acetate Drugs 0.000 description 3
ZBYYWKJVSFHYJL-UHFFFAOYSA-L cobalt(2+);diacetate;tetrahydrate Chemical compound O.O.O.O.[Co+2].CC([O-])=O.CC([O-])=O ZBYYWKJVSFHYJL-UHFFFAOYSA-L 0.000 description 3
QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 3
229960004544 cortisone Drugs 0.000 description 3
229910003460 diamond Inorganic materials 0.000 description 3
239000010432 diamond Substances 0.000 description 3
239000003814 drug Substances 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
239000012362 glacial acetic acid Substances 0.000 description 3
150000002500 ions Chemical class 0.000 description 3
239000012046 mixed solvent Substances 0.000 description 3
DPJRMOMPQZCRJU-UHFFFAOYSA-M thiamine hydrochloride Chemical compound Cl.[Cl-].CC1=C(CCO)SC=[N+]1CC1=CN=C(C)N=C1N DPJRMOMPQZCRJU-UHFFFAOYSA-M 0.000 description 3
229960000344 thiamine hydrochloride Drugs 0.000 description 3
235000019190 thiamine hydrochloride Nutrition 0.000 description 3
239000011747 thiamine hydrochloride Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000037396 body weight Effects 0.000 description 2
210000003763 chloroplast Anatomy 0.000 description 2
238000010668 complexation reaction Methods 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000005194 fractionation Methods 0.000 description 2
238000005227 gel permeation chromatography Methods 0.000 description 2
239000011521 glass Substances 0.000 description 2
238000005259 measurement Methods 0.000 description 2
239000002184 metal Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
125000004433 nitrogen atom Chemical group N* 0.000 description 2
239000002504 physiological saline solution Substances 0.000 description 2
239000011148 porous material Substances 0.000 description 2
BBNQQADTFFCFGB-UHFFFAOYSA-N purpurin Chemical compound C1=CC=C2C(=O)C3=C(O)C(O)=CC(O)=C3C(=O)C2=C1 BBNQQADTFFCFGB-UHFFFAOYSA-N 0.000 description 2
150000003233 pyrroles Chemical class 0.000 description 2
150000003573 thiols Chemical group 0.000 description 2
241000255789 Bombyx mori Species 0.000 description 1
241000195649 Chlorella <Chlorellales> Species 0.000 description 1
241000195493 Cryptophyta Species 0.000 description 1
206010061459 Gastrointestinal ulcer Diseases 0.000 description 1
240000000249 Morus alba Species 0.000 description 1
235000008708 Morus alba Nutrition 0.000 description 1
229910002651 NO3 Inorganic materials 0.000 description 1
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
241000746983 Phleum pratense Species 0.000 description 1
241000700157 Rattus norvegicus Species 0.000 description 1
241000195663 Scenedesmus Species 0.000 description 1
239000012507 Sephadex™ Substances 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical group [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
208000007107 Stomach Ulcer Diseases 0.000 description 1
238000011481 absorbance measurement Methods 0.000 description 1
238000004847 absorption spectroscopy Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
238000007664 blowing Methods 0.000 description 1
244000309464 bull Species 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
230000001684 chronic effect Effects 0.000 description 1
GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 1
229940044175 cobalt sulfate Drugs 0.000 description 1
229910000361 cobalt sulfate Inorganic materials 0.000 description 1
KTVIXTQDYHMGHF-UHFFFAOYSA-L cobalt(2+) sulfate Chemical compound [Co+2].[O-]S([O-])(=O)=O KTVIXTQDYHMGHF-UHFFFAOYSA-L 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000012790 confirmation Methods 0.000 description 1
229920001577 copolymer Polymers 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001914 filtration Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000003349 gelling agent Substances 0.000 description 1
238000012812 general test Methods 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
239000003446 ligand Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
230000007721 medicinal effect Effects 0.000 description 1
229940087646 methanolamine Drugs 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1

Landscapes

Nitrogen Condensed Heterocyclic Rings (AREA)

JP5624188A 1988-03-11 1988-03-11 新規なチアミンコバルチクロロフイリン錯化合物の製法 Granted JPS63264483A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP5624188A JPS63264483A (ja)	1988-03-11	1988-03-11	新規なチアミンコバルチクロロフイリン錯化合物の製法

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP5624188A JPS63264483A (ja)	1988-03-11	1988-03-11	新規なチアミンコバルチクロロフイリン錯化合物の製法

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5227382A Division JPS5841885A (ja)	1982-04-01	1982-04-01	新規なチアミンコバルチクロロフイリン錯化合物

Publications (2)

Publication Number	Publication Date
JPS63264483A JPS63264483A (ja)	1988-11-01
JPH036153B2 true JPH036153B2 (fr)	1991-01-29

Family

ID=13021598

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP5624188A Granted JPS63264483A (ja)	1988-03-11	1988-03-11	新規なチアミンコバルチクロロフイリン錯化合物の製法

Country Status (1)

Country	Link
JP (1)	JPS63264483A (fr)

1988
- 1988-03-11 JP JP5624188A patent/JPS63264483A/ja active Granted

Also Published As

Publication number	Publication date
JPS63264483A (ja)	1988-11-01

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