JPH0556340B2 - - Google Patents
Info
- Publication number
- JPH0556340B2 JPH0556340B2 JP59113258A JP11325884A JPH0556340B2 JP H0556340 B2 JPH0556340 B2 JP H0556340B2 JP 59113258 A JP59113258 A JP 59113258A JP 11325884 A JP11325884 A JP 11325884A JP H0556340 B2 JPH0556340 B2 JP H0556340B2
- Authority
- JP
- Japan
- Prior art keywords
- producing
- trisulfide
- methyl
- ethyl
- group
- 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 - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 claims description 78
- -1 etc. Chemical group 0.000 claims description 56
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 125000004185 ester group Chemical group 0.000 claims description 4
- 125000001033 ether group Chemical group 0.000 claims description 4
- 125000002425 furfuryl group Chemical group C(C1=CC=CO1)* 0.000 claims description 4
- 125000000468 ketone group Chemical group 0.000 claims description 4
- 125000000686 lactone group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical class SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 3
- FPAQRJJEHUMCNA-UHFFFAOYSA-N 1-methoxy-2-(2-methoxyethyltrisulfanyl)ethane Chemical compound COCCSSSCCOC FPAQRJJEHUMCNA-UHFFFAOYSA-N 0.000 claims 2
- PMGSPGRHLCPBHN-UHFFFAOYSA-N methyl 3-[(3-methoxy-3-oxopropyl)trisulfanyl]propanoate Chemical compound COC(=O)CCSSSCCC(=O)OC PMGSPGRHLCPBHN-UHFFFAOYSA-N 0.000 claims 2
- VMQIOYPXZIDNIY-UHFFFAOYSA-N (methyltrisulfanyl)methylbenzene Chemical compound CSSSCC1=CC=CC=C1 VMQIOYPXZIDNIY-UHFFFAOYSA-N 0.000 claims 1
- ORKOECRFEGYATC-UHFFFAOYSA-N 2-[(methyltrisulfanyl)methyl]furan Chemical compound CSSSCC1=CC=CO1 ORKOECRFEGYATC-UHFFFAOYSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000000034 method Methods 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 9
- 238000007796 conventional method Methods 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 210000004623 platelet-rich plasma Anatomy 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 4
- 230000002776 aggregation Effects 0.000 description 4
- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- YENZEWKLSIXGBO-UHFFFAOYSA-N disulfanylethane Chemical compound CCSS YENZEWKLSIXGBO-UHFFFAOYSA-N 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000000341 volatile oil Substances 0.000 description 3
- 240000002234 Allium sativum Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000004611 garlic Nutrition 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- SSCFPXRLONNQFA-UHFFFAOYSA-N methanol;hydrate;hydrochloride Chemical compound O.Cl.OC SSCFPXRLONNQFA-UHFFFAOYSA-N 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 231100000216 vascular lesion Toxicity 0.000 description 2
- 210000003462 vein Anatomy 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 101710186708 Agglutinin Proteins 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 206010008132 Cerebral thrombosis Diseases 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 244000205754 Colocasia esculenta Species 0.000 description 1
- 235000006481 Colocasia esculenta Nutrition 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 101710146024 Horcolin Proteins 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 201000001429 Intracranial Thrombosis Diseases 0.000 description 1
- 101710189395 Lectin Proteins 0.000 description 1
- 238000005684 Liebig rearrangement reaction Methods 0.000 description 1
- 101710179758 Mannose-specific lectin Proteins 0.000 description 1
- 101710150763 Mannose-specific lectin 1 Proteins 0.000 description 1
- 101710150745 Mannose-specific lectin 2 Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000007711 Peperomia pellucida Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000910 agglutinin Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- DOUHZFSGSXMPIE-UHFFFAOYSA-N hydroxidooxidosulfur(.) Chemical compound [O]SO DOUHZFSGSXMPIE-UHFFFAOYSA-N 0.000 description 1
- 230000002766 immunoenhancing effect Effects 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 235000021110 pickles Nutrition 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 229940043274 prophylactic drug Drugs 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59113258A JPS60258157A (ja) | 1984-06-02 | 1984-06-02 | トリサルファイド化合物の製造法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59113258A JPS60258157A (ja) | 1984-06-02 | 1984-06-02 | トリサルファイド化合物の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60258157A JPS60258157A (ja) | 1985-12-20 |
| JPH0556340B2 true JPH0556340B2 (fr) | 1993-08-19 |
Family
ID=14607589
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59113258A Granted JPS60258157A (ja) | 1984-06-02 | 1984-06-02 | トリサルファイド化合物の製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60258157A (fr) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5231114A (en) * | 1990-06-22 | 1993-07-27 | Wakunaga Seiyaku Kabushiki Kaisha | Polysulfides compounds and lipid peroxidation inhibitor containing the polysulfide compounds as active ingredient |
| JP2963730B2 (ja) * | 1990-06-22 | 1999-10-18 | 湧永製薬株式会社 | ポリスルフィド化合物及びこれを有効成分とする脂質過酸化抑制剤 |
| ES2402375T3 (es) * | 2006-11-11 | 2013-05-03 | Ecospray Limited | Procesamiento del ajo |
| JP6851762B2 (ja) * | 2016-09-30 | 2021-03-31 | ホヤ レンズ タイランド リミテッドＨＯＹＡ Ｌｅｎｓ Ｔｈａｉｌａｎｄ Ｌｔｄ | 光学材料用ポリチオール化合物の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5547649A (en) * | 1978-09-30 | 1980-04-04 | Wako Pure Chem Ind Ltd | Production polysulfide |
-
1984
- 1984-06-02 JP JP59113258A patent/JPS60258157A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5547649A (en) * | 1978-09-30 | 1980-04-04 | Wako Pure Chem Ind Ltd | Production polysulfide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60258157A (ja) | 1985-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |