JPH0368880B2 - - Google Patents
Info
- Publication number
- JPH0368880B2 JPH0368880B2 JP58071937A JP7193783A JPH0368880B2 JP H0368880 B2 JPH0368880 B2 JP H0368880B2 JP 58071937 A JP58071937 A JP 58071937A JP 7193783 A JP7193783 A JP 7193783A JP H0368880 B2 JPH0368880 B2 JP H0368880B2
- Authority
- JP
- Japan
- Prior art keywords
- pervicoside
- formula
- methanol
- weight
- pyridine
- 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 - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 claims description 13
- 229940121375 antifungal agent Drugs 0.000 claims description 11
- 239000003429 antifungal agent Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 9
- RGMKMMVBOLIWCC-UHFFFAOYSA-M neothyoside a Chemical compound [Na+].OC1C(OC)C(O)C(CO)OC1OC1C(O)C(OC2C(C(O)C(OC3C(OCC(C3O)OS([O-])(=O)=O)OC3C(C4CC=C5C6(C)CCC7C6(C(OC7(CCCC(C)(C)OC(C)=O)C)=O)C(O)CC5C4(C)CC3)(C)C)OC2C)O)OC(CO)C1O RGMKMMVBOLIWCC-UHFFFAOYSA-M 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- DEHSMOLOWCNYJI-CVURUQKOSA-M chembl504650 Chemical compound [Na+].O[C@@H]1[C@@H](OC)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O[C@H]3[C@@H](OC[C@H]([C@@H]3O)OS([O-])(=O)=O)O[C@@H]3C([C@H]4[C@](C=5[C@H]([C@@]6(CC[C@H]7[C@]6(C(O[C@]7(CCCC(C)C)C)=O)[C@@H](O)C=5)C)CC4)(C)CC3)(C)C)O[C@@H]2C)O)O[C@H](CO)[C@H]1O DEHSMOLOWCNYJI-CVURUQKOSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- KQZXVZVRFIRDCU-UHFFFAOYSA-M neothyoside c Chemical compound [Na+].OC1C(OC)C(O)C(CO)OC1OC1C(O)C(OC2C(C(O)C(OC3C(OCC(C3O)OS([O-])(=O)=O)OC3C(C4CC=C5C6(C)CCC7C6(C(OC7(CCC=C(C)C)C)=O)C(O)CC5C4(C)CC3)(C)C)OC2C)O)OC(CO)C1O KQZXVZVRFIRDCU-UHFFFAOYSA-M 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- STQXEEIUKGDBIY-UHFFFAOYSA-N DS-pervicoside C Natural products OC1C(OC)C(O)C(CO)OC1OC1C(O)C(OC2C(C(O)C(OC3C(OCC(O)C3O)OC3C(C4C(C=5C(C6(CCC7C6(C(OC7(CCCC(C)C)C)=O)C(O)C=5)C)CC4)(C)CC3)(C)C)OC2C)O)OC(CO)C1O STQXEEIUKGDBIY-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- LVYLCBNXHHHPSB-UHFFFAOYSA-N 2-hydroxyethyl salicylate Chemical compound OCCOC(=O)C1=CC=CC=C1O LVYLCBNXHHHPSB-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- ALTFPZXSVFRAMT-UHFFFAOYSA-N DS-pervicoside A Natural products OC1C(OC)C(O)C(CO)OC1OC1C(O)C(OC2C(C(O)C(OC3C(OCC(O)C3O)OC3C(C4C(C=5C(C6(CCC7C6(C(OC7(CCCC(C)(C)OC(C)=O)C)=O)C(O)C=5)C)CC4)(C)CC3)(C)C)OC2C)O)OC(CO)C1O ALTFPZXSVFRAMT-UHFFFAOYSA-N 0.000 description 4
- KYXMFHJBYUILDU-UHFFFAOYSA-N DS-pervicoside B Natural products OC1C(OC)C(O)C(CO)OC1OC1C(O)C(OC2C(C(O)C(OC3C(OCC(O)C3O)OC3C(C4C(C=5C(C6(CCC7C6(C(OC7(CCC=C(C)C)C)=O)C(O)C=5)C)CC4)(C)CC3)(C)C)OC2C)O)OC(CO)C1O KYXMFHJBYUILDU-UHFFFAOYSA-N 0.000 description 4
- 241000251511 Holothuroidea Species 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 239000008186 active pharmaceutical agent Substances 0.000 description 4
- 235000012745 brilliant blue FCF Nutrition 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 230000007935 neutral effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- 229930191432 DS-pervicoside Natural products 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 241000451664 Holothuria pervicax Species 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- -1 methanol) Chemical compound 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 230000000843 anti-fungal effect Effects 0.000 description 2
- 238000004040 coloring Methods 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- LBOVMDOAMWYGHK-UHFFFAOYSA-N ethanol;methylsulfinylmethane Chemical compound CCO.CS(C)=O LBOVMDOAMWYGHK-UHFFFAOYSA-N 0.000 description 2
- XTLNYNMNUCLWEZ-UHFFFAOYSA-N ethanol;propan-2-one Chemical compound CCO.CC(C)=O XTLNYNMNUCLWEZ-UHFFFAOYSA-N 0.000 description 2
- 229960002389 glycol salicylate Drugs 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 2
- KSCKTBJJRVPGKM-UHFFFAOYSA-N octan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-].CCCCCCCC[O-] KSCKTBJJRVPGKM-UHFFFAOYSA-N 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- 229940057838 polyethylene glycol 4000 Drugs 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 2
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 2
- 201000004647 tinea pedis Diseases 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- 241000222122 Candida albicans Species 0.000 description 1
- 206010007134 Candida infections Diseases 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- IIUZTXTZRGLYTI-UHFFFAOYSA-N Dihydrogriseofulvin Natural products COC1CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 IIUZTXTZRGLYTI-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UXWOXTQWVMFRSE-UHFFFAOYSA-N Griseoviridin Natural products O=C1OC(C)CC=C(C(NCC=CC=CC(O)CC(O)C2)=O)SCC1NC(=O)C1=COC2=N1 UXWOXTQWVMFRSE-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229920000715 Mucilage Polymers 0.000 description 1
- DDUHZTYCFQRHIY-UHFFFAOYSA-N Negwer: 6874 Natural products COC1=CC(=O)CC(C)C11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-UHFFFAOYSA-N 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 241000130764 Tinea Species 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001032 anti-candidal effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 201000003984 candidiasis Diseases 0.000 description 1
- KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- DDUHZTYCFQRHIY-RBHXEPJQSA-N griseofulvin Chemical compound COC1=CC(=O)C[C@@H](C)[C@@]11C(=O)C(C(OC)=CC(OC)=C2Cl)=C2O1 DDUHZTYCFQRHIY-RBHXEPJQSA-N 0.000 description 1
- 229960002867 griseofulvin Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000003410 keratolytic agent Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 229940068918 polyethylene glycol 400 Drugs 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 229940084106 spermaceti Drugs 0.000 description 1
- 239000012177 spermaceti Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960002180 tetracycline Drugs 0.000 description 1
- 229930101283 tetracycline Natural products 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940098465 tincture Drugs 0.000 description 1
- 210000005239 tubule Anatomy 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Landscapes
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58071937A JPS59196900A (ja) | 1983-04-22 | 1983-04-22 | 新規オリゴ配糖体パ−ビコサイド類およびそれを含有してなる抗真菌剤 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58071937A JPS59196900A (ja) | 1983-04-22 | 1983-04-22 | 新規オリゴ配糖体パ−ビコサイド類およびそれを含有してなる抗真菌剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59196900A JPS59196900A (ja) | 1984-11-08 |
| JPH0368880B2 true JPH0368880B2 (enrdf_load_stackoverflow) | 1991-10-30 |
Family
ID=13474917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58071937A Granted JPS59196900A (ja) | 1983-04-22 | 1983-04-22 | 新規オリゴ配糖体パ−ビコサイド類およびそれを含有してなる抗真菌剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59196900A (enrdf_load_stackoverflow) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104991028B (zh) * | 2015-07-31 | 2017-10-31 | 北京市药品检验所 | Lc‑ms测试物中不挥发性缓冲盐含量的降低方法 |
-
1983
- 1983-04-22 JP JP58071937A patent/JPS59196900A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS59196900A (ja) | 1984-11-08 |
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