CA1077421A - Antibiotique sf-1540 produit par un streptomyces - Google Patents

Antibiotique sf-1540 produit par un streptomyces

Info

Publication number: CA1077421A
Authority: CA; Canada
Prior art keywords: substance; derivative; methanol; antibiotic substance; antibiotic
Prior art date: 1975-12-29
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

CA268,234A

Other languages

English (en)

Inventor

Yasumitsu Kondo

Hiroshi Watanabe

Takashi Shomura

Taro Niida

Shigeharu Inouye

Tetsuro Watanabe

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.)

Meiji Seika Kaisha Ltd

Original Assignee

Meiji Seika Kaisha 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.)

1975-12-29

Filing date

1976-12-20

Publication date

1980-05-13

1975-12-29 Priority claimed from JP50157469A external-priority patent/JPS5824118B2/ja

1976-04-19 Priority claimed from JP51043659A external-priority patent/JPS5929080B2/ja

1976-12-20 Application filed by Meiji Seika Kaisha Ltd filed Critical Meiji Seika Kaisha Ltd

1980-05-13 Application granted granted Critical

1980-05-13 Publication of CA1077421A publication Critical patent/CA1077421A/fr

Status Expired legal-status Critical Current

Links

230000003115 biocidal effect Effects 0.000 title claims abstract description 20
241000187747 Streptomyces Species 0.000 title claims abstract description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 75
239000000126 substance Substances 0.000 claims abstract description 69
241000187391 Streptomyces hygroscopicus Species 0.000 claims abstract description 7
244000005700 microbiome Species 0.000 claims abstract description 7
238000012258 culturing Methods 0.000 claims abstract 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 17
238000000034 method Methods 0.000 claims description 14
238000000862 absorption spectrum Methods 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
238000004519 manufacturing process Methods 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 5
238000000655 nuclear magnetic resonance spectrum Methods 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
230000003287 optical effect Effects 0.000 claims description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
238000004458 analytical method Methods 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000012286 potassium permanganate Substances 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 abstract description 2
230000003389 potentiating effect Effects 0.000 abstract description 2
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
229920001817 Agar Polymers 0.000 description 14
239000008272 agar Substances 0.000 description 14
239000002609 medium Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
239000000843 powder Substances 0.000 description 12
150000001875 compounds Chemical class 0.000 description 8
229920002472 Starch Polymers 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000008107 starch Substances 0.000 description 6
235000019698 starch Nutrition 0.000 description 6
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
TXHIDIHEXDFONW-UHFFFAOYSA-N benzene;propan-2-one Chemical compound CC(C)=O.C1=CC=CC=C1 TXHIDIHEXDFONW-UHFFFAOYSA-N 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
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 4
SHZGCJCMOBCMKK-JFNONXLTSA-N L-rhamnopyranose Chemical compound C[C@@H]1OC(O)[C@H](O)[C@H](O)[C@H]1O SHZGCJCMOBCMKK-JFNONXLTSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
239000008103 glucose Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000010521 absorption reaction Methods 0.000 description 3
239000013543 active substance Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000000203 mixture Substances 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 3
239000007858 starting material Substances 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
BBBFYZOJHSYQMW-LGDQNDJISA-N (2s)-2,4-diamino-4-oxobutanoic acid;(2r,3s,4r,5r)-2,3,4,5,6-pentahydroxyhexanal Chemical compound OC(=O)[C@@H](N)CC(N)=O.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O BBBFYZOJHSYQMW-LGDQNDJISA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
240000004808 Saccharomyces cerevisiae Species 0.000 description 2
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
235000019764 Soybean Meal Nutrition 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
241000209140 Triticum Species 0.000 description 2
235000021307 Triticum Nutrition 0.000 description 2
239000002253 acid Substances 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
229950005499 carbon tetrachloride Drugs 0.000 description 2
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
229960005150 glycerol Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
210000001161 mammalian embryo Anatomy 0.000 description 2
239000000463 material Substances 0.000 description 2
XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000000049 pigment Substances 0.000 description 2
238000011218 seed culture Methods 0.000 description 2
235000020183 skimmed milk Nutrition 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000004455 soybean meal Substances 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
YBSYYLRYPMFRNL-UHFFFAOYSA-N 2,2-bis(methylsulfonyl)propane Chemical compound CS(=O)(=O)C(C)(C)S(C)(=O)=O YBSYYLRYPMFRNL-UHFFFAOYSA-N 0.000 description 1
241000352690 Alternaria kikuchiana Species 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
241001465180 Botrytis Species 0.000 description 1
241000222122 Candida albicans Species 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
241000222235 Colletotrichum orbiculare Species 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
RFSUNEUAIZKAJO-VRPWFDPXSA-N D-Fructose Natural products OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
SHZGCJCMOBCMKK-UHFFFAOYSA-N D-mannomethylose Natural products CC1OC(O)C(O)C(O)C1O SHZGCJCMOBCMKK-UHFFFAOYSA-N 0.000 description 1
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
108010082495 Dietary Plant Proteins Proteins 0.000 description 1
101100130497 Drosophila melanogaster Mical gene Proteins 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
241000223221 Fusarium oxysporum Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
SRBFZHDQGSBBOR-HWQSCIPKSA-N L-arabinopyranose Chemical compound O[C@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-HWQSCIPKSA-N 0.000 description 1
PNNNRSAQSRJVSB-UHFFFAOYSA-N L-rhamnose Natural products CC(O)C(O)C(O)C(O)C=O PNNNRSAQSRJVSB-UHFFFAOYSA-N 0.000 description 1
241000158723 Melia Species 0.000 description 1
101100345589 Mus musculus Mical1 gene Proteins 0.000 description 1
241000187480 Mycobacterium smegmatis Species 0.000 description 1
229910019142 PO4 Inorganic materials 0.000 description 1
MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
241000235070 Saccharomyces Species 0.000 description 1
241000877399 Saccharomyces chevalieri Species 0.000 description 1
241000576755 Sclerotia Species 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241001617088 Thanatephorus sasakii Species 0.000 description 1
241000223238 Trichophyton Species 0.000 description 1
MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
238000013019 agitation Methods 0.000 description 1
239000003513 alkali Substances 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229940095731 candida albicans Drugs 0.000 description 1
230000015271 coagulation Effects 0.000 description 1
238000005345 coagulation Methods 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
239000013058 crude material Substances 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000005194 fractionation Methods 0.000 description 1
239000000499 gel Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
239000001963 growth medium Substances 0.000 description 1
JYVHOGDBFNJNMR-UHFFFAOYSA-N hexane;hydrate Chemical compound O.CCCCCC JYVHOGDBFNJNMR-UHFFFAOYSA-N 0.000 description 1
231100000086 high toxicity Toxicity 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
229910010272 inorganic material Inorganic materials 0.000 description 1
239000011147 inorganic material Substances 0.000 description 1
CDAISMWEOUEBRE-GPIVLXJGSA-N inositol Chemical compound O[C@H]1[C@H](O)[C@@H](O)[C@H](O)[C@H](O)[C@@H]1O CDAISMWEOUEBRE-GPIVLXJGSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
238000002955 isolation Methods 0.000 description 1
238000009630 liquid culture Methods 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
230000004048 modification Effects 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
230000000877 morphologic effect Effects 0.000 description 1
229930014626 natural product Natural products 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
239000006877 oatmeal agar Substances 0.000 description 1
239000011368 organic material Substances 0.000 description 1
HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
229960001841 potassium permanganate Drugs 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000010344 sodium nitrate Nutrition 0.000 description 1
239000004317 sodium nitrate Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
230000028070 sporulation Effects 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K35/00—Medicinal preparations containing materials or reaction products thereof with undetermined constitution
- A61K35/66—Microorganisms or materials therefrom
- A61K35/74—Bacteria

Landscapes

Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Microbiology (AREA)
Mycology (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CA268,234A 1975-12-29 1976-12-20 Antibiotique sf-1540 produit par un streptomyces Expired CA1077421A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP50157469A JPS5824118B2 (ja)	1975-12-29	1975-12-29	シンコウセイブツシツｓｆ −１５４０ブツシツノセイゾウホウ
JP51043659A JPS5929080B2 (ja)	1976-04-19	1976-04-19	抗生物質ｓｆ−１５４０物質の新規誘導体及びその製法

Publications (1)

Publication Number	Publication Date
CA1077421A true CA1077421A (fr)	1980-05-13

Family

ID=26383460

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA268,234A Expired CA1077421A (fr)	1975-12-29	1976-12-20	Antibiotique sf-1540 produit par un streptomyces

Country Status (4)

Country	Link
CA (1)	CA1077421A (fr)
DE (1)	DE2659180C2 (fr)
FR (1)	FR2336940A1 (fr)
GB (1)	GB1517629A (fr)

1976
- 1976-12-20 GB GB5304776A patent/GB1517629A/en not_active Expired
- 1976-12-20 CA CA268,234A patent/CA1077421A/fr not_active Expired
- 1976-12-28 DE DE19762659180 patent/DE2659180C2/de not_active Expired
- 1976-12-29 FR FR7639488A patent/FR2336940A1/fr active Granted

Also Published As

Publication number	Publication date
DE2659180A1 (de)	1977-07-07
FR2336940A1 (fr)	1977-07-29
GB1517629A (en)	1978-07-12
DE2659180C2 (de)	1984-02-02
FR2336940B1 (fr)	1981-06-26

Legal Events

Date	Code	Title	Description
1997-05-13	MKEX	Expiry

Publication	Publication Date	Title
EP0376300B1 (fr)	1993-07-28	Substance DC 113 et procédé pour sa production
US4923990A (en)	1990-05-08	Pyrindamycins A and B and duocarmycin A antibiotics derived from certain streptomyces culture
US4107297A (en)	1978-08-15	Antibiotic compound
EP0298640B1 (fr)	1992-08-19	Agents antimicrobien, FR 109 615, et sa production
US4181715A (en)	1980-01-01	Novel antibiotic substance SF-1540 and its derivative, and process for the production thereof
HU184256B (en)	1984-07-30	Process for producing citostatic antibiotic complexes
EP0318056A2 (fr)	1989-05-31	Antibiotiques et procédé pour leur production
EP0326173B1 (fr)	1994-01-19	Substance antibiotique antitumorale et méthode pour sa production
KR920001448B1 (ko)	1992-02-14	Bbm-2478 항생제 착화합물
US4248863A (en)	1981-02-03	Antibiotics saframycins A, B, C, D and E and process for producing the same
US4550159A (en)	1985-10-29	Anthracycline compounds
EP0491956B1 (fr)	1995-11-02	Reveromycine a, sa production, ainsi que medicament antitumoral et fongicide
US4372947A (en)	1983-02-08	Antibiotic saframycin S and process for producing the same
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