JPS59196900A - 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 - Google Patents

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

Info

Publication number: JPS59196900A
Authority: JP; Japan
Prior art keywords: formula; group; pervicoside; antifungal agent; perpicoside
Prior art date: 1983-04-22
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

Application number

JP58071937A

Other languages

English (en)

Japanese (ja)

Other versions

JPH0368880B2 (cs

Inventor

Isao Kitagawa

北川　勲

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.)

Takeda Pharmaceutical Co Ltd

Original Assignee

Takeda Chemical Industries Ltd

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.)

1983-04-22

Filing date

1983-04-22

Publication date

1984-11-08

1983-04-22 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1983-04-22 Priority to JP58071937A priority Critical patent/JPS59196900A/ja

1984-11-08 Publication of JPS59196900A publication Critical patent/JPS59196900A/ja

1991-10-30 Publication of JPH0368880B2 publication Critical patent/JPH0368880B2/ja

Status Granted legal-status Critical Current

Links

229940121375 antifungal agent Drugs 0.000 title claims abstract description 14
239000003429 antifungal agent Substances 0.000 title claims abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 42
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 26
239000003795 chemical substances by application Substances 0.000 abstract description 6
-1 methanol Chemical compound 0.000 abstract description 4
238000002360 preparation method Methods 0.000 abstract description 3
241000451664 Holothuria pervicax Species 0.000 abstract description 2
238000010438 heat treatment Methods 0.000 abstract description 2
238000010898 silica gel chromatography Methods 0.000 abstract description 2
241000222120 Candida <Saccharomycetales> Species 0.000 abstract 1
241000233866 Fungi Species 0.000 abstract 1
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 abstract 1
239000000463 material Substances 0.000 abstract 1
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 abstract 1
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 abstract 1
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 14
TVZRAEYQIKYCPH-UHFFFAOYSA-N 3-(trimethylsilyl)propane-1-sulfonic acid Chemical compound C[Si](C)(C)CCCS(O)(=O)=O TVZRAEYQIKYCPH-UHFFFAOYSA-N 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
235000019441 ethanol Nutrition 0.000 description 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
238000006243 chemical reaction Methods 0.000 description 8
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 7
239000002904 solvent Substances 0.000 description 7
LVYLCBNXHHHPSB-UHFFFAOYSA-N 2-hydroxyethyl salicylate Chemical compound OCCOC(=O)C1=CC=CC=C1O LVYLCBNXHHHPSB-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
239000013078 crystal Substances 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
238000000034 method Methods 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
241000251511 Holothuroidea Species 0.000 description 3
230000000843 anti-fungal effect Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000002609 medium Substances 0.000 description 3
102220043690 rs1049562 Human genes 0.000 description 3
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 3
201000004647 tinea pedis Diseases 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
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
241000282376 Panthera tigris Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000008186 active pharmaceutical agent Substances 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
235000012745 brilliant blue FCF Nutrition 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
238000004040 coloring Methods 0.000 description 2
229960002389 glycol salicylate Drugs 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
239000004615 ingredient Substances 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
239000000843 powder Substances 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
238000000926 separation method 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
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
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 1
241000251468 Actinopterygii Species 0.000 description 1
241000894006 Bacteria Species 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
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
229920000715 Mucilage Polymers 0.000 description 1
229930182555 Penicillin Natural products 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
239000004098 Tetracycline Substances 0.000 description 1
241000736772 Uria 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
230000001032 anti-candidal effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
229940124587 cephalosporin Drugs 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
239000012141 concentrate Substances 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
230000002538 fungal effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 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
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
150000002960 penicillins Chemical class 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229940057838 polyethylene glycol 4000 Drugs 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
102220223891 rs370721650 Human genes 0.000 description 1
229960004889 salicylic acid Drugs 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
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000007449 t5 medium Substances 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
229940098465 tincture Drugs 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Steroid Compounds (AREA)

JP58071937A 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 Granted JPS59196900A (ja)

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 true JPS59196900A (ja)	1984-11-08
JPH0368880B2 JPH0368880B2 (cs)	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 (cs)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104991028A (zh) *	2015-07-31	2015-10-21	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

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN104991028A (zh) *	2015-07-31	2015-10-21	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

Also Published As

Publication number	Publication date
JPH0368880B2 (cs)	1991-10-30

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Takeda et al.	1977	Metallo-anthocyanins. I Reconstruction of commelinin from its components, awobanin, flavocommelin and magnesium
DE1935967C3 (de)	1980-09-25	Naphthacenderivate, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE3044740A1 (de)	1981-09-24	Nucleosidderivate, ihre herstellung und pharmazeutische mittel
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CH640870A5 (de)	1984-01-31	Verfahren zur herstellung von 9-desacetyl-9-formyl-n-trifluoracetyldaunorubicin.
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DE1807585C3 (de)	1974-11-07	14,15beta-Epoxycardenolide, Verfahren zu deren Herstellung und diese enthaltende Mittel
SCHRECKER et al.	1956	Components of Podophyllin. XIX. 2 Isomorphism in the Podophyllotoxin Series
DE2403429A1 (de)	1974-07-25	Insektizide
DE1593964C3 (de)	1974-03-21	Triacetyl-Spiramycin I und Verfahren zu seiner Herstellung
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EP0054514A1 (de)	1982-06-23	Neue antibiotisch wirksame Aminopapulacandin-Derivate

JPS59196900A - 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 - Google Patents

Info

Links

Landscapes

Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=13474917

Family Applications (1)

Country Status (1)

Cited By (1)

Cited By (1)

Also Published As

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