JPH0477754B2 - - Google Patents

Info

Publication number: JPH0477754B2
Authority: JP; Japan
Prior art keywords: compound; water; salt; culture; reaction
Prior art date: 1984-09-18
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

JP19598584A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6172789A (ja

Inventor

Hideo Ono

Setsuo Harada

Shigetoshi Tsuboya

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.)

1984-09-18

Filing date

1984-09-18

Publication date

1992-12-09

1984-09-18 Application filed by Takeda Chemical Industries Ltd filed Critical Takeda Chemical Industries Ltd

1984-09-18 Priority to JP19598584A priority Critical patent/JPS6172789A/ja

1984-12-11 Priority to DE8484115168T priority patent/DE3481769D1/de

1984-12-11 Priority to EP84115168A priority patent/EP0150378B1/de

1984-12-11 Priority to AT84115168T priority patent/ATE51403T1/de

1984-12-14 Priority to US06/681,784 priority patent/US4723004A/en

1984-12-14 Priority to CA000470115A priority patent/CA1297056C/en

1984-12-15 Priority to KR1019840007985A priority patent/KR930000276B1/ko

1986-04-14 Publication of JPS6172789A publication Critical patent/JPS6172789A/ja

1992-12-09 Publication of JPH0477754B2 publication Critical patent/JPH0477754B2/ja

Status Granted legal-status Critical Current

Links

150000001875 compounds Chemical group 0.000 claims description 92
244000005700 microbiome Species 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 24
238000004519 manufacturing process Methods 0.000 claims description 11
241000589516 Pseudomonas Species 0.000 claims description 7
238000011282 treatment Methods 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
238000006243 chemical reaction Methods 0.000 description 34
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 29
235000002639 sodium chloride Nutrition 0.000 description 25
239000000243 solution Substances 0.000 description 25
239000002609 medium Substances 0.000 description 24
238000000034 method Methods 0.000 description 22
239000000126 substance Substances 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
238000005406 washing Methods 0.000 description 14
241000894006 Bacteria Species 0.000 description 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000007864 aqueous solution Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 12
230000001580 bacterial effect Effects 0.000 description 11
239000000047 product Substances 0.000 description 11
-1 7-formylamino-cephem compound Chemical class 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
238000012258 culturing Methods 0.000 description 10
239000000843 powder Substances 0.000 description 10
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 8
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
230000003115 biocidal effect Effects 0.000 description 8
238000004128 high performance liquid chromatography Methods 0.000 description 8
ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
239000008363 phosphate buffer Substances 0.000 description 8
208000035143 Bacterial infection Diseases 0.000 description 7
238000000862 absorption spectrum Methods 0.000 description 7
208000022362 bacterial infectious disease Diseases 0.000 description 7
239000003814 drug Substances 0.000 description 7
238000001228 spectrum Methods 0.000 description 7
229920001817 Agar Polymers 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 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 6
229920005654 Sephadex Polymers 0.000 description 6
239000012507 Sephadex™ Substances 0.000 description 6
238000005273 aeration Methods 0.000 description 6
239000008272 agar Substances 0.000 description 6
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 6
239000002994 raw material Substances 0.000 description 6
239000011780 sodium chloride Substances 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
229940124597 therapeutic agent Drugs 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
241001552694 Rhizobacter Species 0.000 description 5
230000002378 acidificating effect Effects 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000006228 supernatant Substances 0.000 description 5
QNAYBMKLOCPYGJ-UHFFFAOYSA-N Alanine Chemical compound CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 4
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
239000001888 Peptone Substances 0.000 description 4
108010080698 Peptones Proteins 0.000 description 4
241000589774 Pseudomonas sp. Species 0.000 description 4
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 4
229910052921 ammonium sulfate Inorganic materials 0.000 description 4
235000011130 ammonium sulphate Nutrition 0.000 description 4
230000000844 anti-bacterial effect Effects 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 4
239000012153 distilled water Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
238000000855 fermentation Methods 0.000 description 4
230000004151 fermentation Effects 0.000 description 4
235000013312 flour Nutrition 0.000 description 4
230000012010 growth Effects 0.000 description 4
UYTPUPDQBNUYGX-UHFFFAOYSA-N guanine Chemical compound O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 description 4
239000000543 intermediate Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
235000013372 meat Nutrition 0.000 description 4
235000019319 peptone Nutrition 0.000 description 4
239000011734 sodium Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
102000016938 Catalase Human genes 0.000 description 3
108010053835 Catalase Proteins 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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 3
235000010469 Glycine max Nutrition 0.000 description 3
241000124008 Mammalia Species 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
235000001014 amino acid Nutrition 0.000 description 3
235000011114 ammonium hydroxide Nutrition 0.000 description 3
239000000872 buffer Substances 0.000 description 3
229940041514 candida albicans extract Drugs 0.000 description 3
239000000969 carrier Substances 0.000 description 3
229940124587 cephalosporin Drugs 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000004108 freeze drying Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
238000004811 liquid chromatography Methods 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
239000000049 pigment Substances 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
230000003068 static effect Effects 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
239000012138 yeast extract Substances 0.000 description 3
YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
OYIFNHCXNCRBQI-UHFFFAOYSA-N 2-aminoadipic acid Chemical compound OC(=O)C(N)CCCC(O)=O OYIFNHCXNCRBQI-UHFFFAOYSA-N 0.000 description 2
FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
HOKIDJSKDBPKTQ-GLXFQSAKSA-N Cephalosporin C Natural products S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
102000004316 Oxidoreductases Human genes 0.000 description 2
108090000854 Oxidoreductases Proteins 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
229920002472 Starch Polymers 0.000 description 2
241001480014 Trigonopsis Species 0.000 description 2
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
238000005377 adsorption chromatography Methods 0.000 description 2
238000013019 agitation Methods 0.000 description 2
235000004279 alanine Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
150000003863 ammonium salts Chemical class 0.000 description 2
239000003957 anion exchange resin Substances 0.000 description 2
239000003242 anti bacterial agent Substances 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
HOKIDJSKDBPKTQ-GLXFQSAKSA-M cephalosporin C(1-) Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H]([NH3+])C([O-])=O)[C@@H]12 HOKIDJSKDBPKTQ-GLXFQSAKSA-M 0.000 description 2
150000001793 charged compounds Chemical class 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
238000002983 circular dichroism Methods 0.000 description 2
229940104302 cytosine Drugs 0.000 description 2
238000001514 detection method Methods 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
239000000284 extract Substances 0.000 description 2
238000001914 filtration Methods 0.000 description 2
210000003495 flagella Anatomy 0.000 description 2
235000011389 fruit/vegetable juice Nutrition 0.000 description 2
235000011187 glycerol Nutrition 0.000 description 2
238000004255 ion exchange chromatography Methods 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
229940035429 isobutyl alcohol Drugs 0.000 description 2
231100000053 low toxicity Toxicity 0.000 description 2
230000000813 microbial effect Effects 0.000 description 2
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
239000008057 potassium phosphate buffer Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229940088417 precipitated calcium carbonate Drugs 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
238000004366 reverse phase liquid chromatography Methods 0.000 description 2
239000002689 soil Substances 0.000 description 2
241000894007 species Species 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
239000003643 water by type Substances 0.000 description 2
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
HPJMGUYYTCSKPC-UHFFFAOYSA-N 2-methylpropan-1-ol hydrate Chemical compound O.CC(C)CO HPJMGUYYTCSKPC-UHFFFAOYSA-N 0.000 description 1
WTLKTXIHIHFSGU-UHFFFAOYSA-N 2-nitrosoguanidine Chemical compound NC(N)=NN=O WTLKTXIHIHFSGU-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
241000186361 Actinobacteria <class> Species 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
238000007362 Burton trifluoromethylation reaction Methods 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
229940123748 Catalase inhibitor Drugs 0.000 description 1
229930186147 Cephalosporin Natural products 0.000 description 1
LXWBXEWUSAABOA-UHFFFAOYSA-N Cephamycin-C Natural products S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)C(OC)(NC(=O)CCCC(N)C(O)=O)C21 LXWBXEWUSAABOA-UHFFFAOYSA-N 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
OYIFNHCXNCRBQI-SCSAIBSYSA-N D-2-aminoadipic acid Chemical compound OC(=O)[C@H](N)CCCC(O)=O OYIFNHCXNCRBQI-SCSAIBSYSA-N 0.000 description 1
102000004674 D-amino-acid oxidase Human genes 0.000 description 1
108010003989 D-amino-acid oxidase Proteins 0.000 description 1
RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 description 1
229930182818 D-methionine Natural products 0.000 description 1
239000004470 DL Methionine Substances 0.000 description 1
XWCFYHBHOFBVIV-UHFFFAOYSA-N Deacetylcephalosporin C Natural products S1CC(CO)=C(C(O)=O)N2C(=O)C(NC(=O)CCCC(N)C(O)=O)C21 XWCFYHBHOFBVIV-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
108090000204 Dipeptidase 1 Proteins 0.000 description 1
101000925662 Enterobacteria phage PRD1 Endolysin Proteins 0.000 description 1
241000283086 Equidae Species 0.000 description 1
241000588724 Escherichia coli Species 0.000 description 1
241000233866 Fungi Species 0.000 description 1
241000287828 Gallus gallus Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
108010068370 Glutens Proteins 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
238000003794 Gram staining Methods 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 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
229910019142 PO4 Inorganic materials 0.000 description 1
108010073038 Penicillin Amidase Proteins 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
241001480015 Trigonopsis variabilis Species 0.000 description 1
108010046334 Urease Proteins 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
238000007792 addition Methods 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
235000010323 ascorbic acid Nutrition 0.000 description 1
239000011668 ascorbic acid Substances 0.000 description 1
229960005070 ascorbic acid Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
229960002319 barbital Drugs 0.000 description 1
159000000009 barium salts Chemical class 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
102000006635 beta-lactamase Human genes 0.000 description 1
125000003460 beta-lactamyl group Chemical group 0.000 description 1
GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
230000004071 biological effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229960002685 biotin Drugs 0.000 description 1
235000020958 biotin Nutrition 0.000 description 1
239000011616 biotin Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910021538 borax Inorganic materials 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
235000010216 calcium carbonate Nutrition 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
235000011148 calcium chloride Nutrition 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
235000013877 carbamide Nutrition 0.000 description 1
235000010980 cellulose Nutrition 0.000 description 1
229920002678 cellulose Polymers 0.000 description 1
150000001780 cephalosporins Chemical class 0.000 description 1
LXWBXEWUSAABOA-VXSYNFHWSA-N cephamycin C Chemical compound S1CC(COC(N)=O)=C(C(O)=O)N2C(=O)[C@@](OC)(NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 LXWBXEWUSAABOA-VXSYNFHWSA-N 0.000 description 1
235000013330 chicken meat Nutrition 0.000 description 1
238000001142 circular dichroism spectrum Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000001816 cooling Methods 0.000 description 1
XWCFYHBHOFBVIV-JWKOBGCHSA-N deacetylcephalosporin C Chemical compound S1CC(CO)=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CCC[C@@H](N)C(O)=O)[C@H]21 XWCFYHBHOFBVIV-JWKOBGCHSA-N 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
238000011033 desalting Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
FYGDTMLNYKFZSV-MRCIVHHJSA-N dextrin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)OC1O[C@@H]1[C@@H](CO)OC(O[C@@H]2[C@H](O[C@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-MRCIVHHJSA-N 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
150000005332 diethylamines Chemical class 0.000 description 1
XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
235000011180 diphosphates Nutrition 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
210000005069 ears Anatomy 0.000 description 1
239000012156 elution solvent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000028564 filamentous growth Effects 0.000 description 1
238000007710 freezing Methods 0.000 description 1
230000008014 freezing Effects 0.000 description 1
239000007789 gas Substances 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
239000000174 gluconic acid Substances 0.000 description 1
235000012208 gluconic acid Nutrition 0.000 description 1
235000021312 gluten Nutrition 0.000 description 1
239000010439 graphite Substances 0.000 description 1
229910002804 graphite Inorganic materials 0.000 description 1
229940093915 gynecological organic acid Drugs 0.000 description 1
210000004209 hair Anatomy 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
229910017053 inorganic salt Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940046892 lead acetate Drugs 0.000 description 1
238000009630 liquid culture Methods 0.000 description 1
229910003002 lithium salt Inorganic materials 0.000 description 1
159000000002 lithium salts Chemical class 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
235000012054 meals Nutrition 0.000 description 1
238000005259 measurement Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
FFEARJCKVFRZRR-UHFFFAOYSA-N methionine Chemical compound CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 description 1
229930182817 methionine Natural products 0.000 description 1
235000006109 methionine Nutrition 0.000 description 1
CEQFOVLGLXCDCX-WUKNDPDISA-N methyl red Chemical compound C1=CC(N(C)C)=CC=C1\N=N\C1=CC=CC=C1C(O)=O CEQFOVLGLXCDCX-WUKNDPDISA-N 0.000 description 1
150000003956 methylamines Chemical class 0.000 description 1
239000011785 micronutrient Substances 0.000 description 1
235000013369 micronutrients Nutrition 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
235000019796 monopotassium phosphate Nutrition 0.000 description 1
230000004899 motility Effects 0.000 description 1
238000002703 mutagenesis Methods 0.000 description 1
231100000350 mutagenesis Toxicity 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
150000002830 nitrogen compounds Chemical class 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000006916 nutrient agar Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
235000014593 oils and fats Nutrition 0.000 description 1
239000002674 ointment Substances 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 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
239000008055 phosphate buffer solution Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
230000001766 physiological effect Effects 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
238000005498 polishing Methods 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 1
244000144977 poultry Species 0.000 description 1
235000013594 poultry meat Nutrition 0.000 description 1
229920003124 powdered cellulose Polymers 0.000 description 1
235000019814 powdered cellulose Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
238000011218 seed culture Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
239000004328 sodium tetraborate Substances 0.000 description 1
235000010339 sodium tetraborate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
238000010257 thawing Methods 0.000 description 1
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 1
229960000344 thiamine hydrochloride Drugs 0.000 description 1
235000019190 thiamine hydrochloride Nutrition 0.000 description 1
239000011747 thiamine hydrochloride Substances 0.000 description 1
MPSUGQWRVNRJEE-UHFFFAOYSA-N triazol-1-amine Chemical compound NN1C=CN=N1 MPSUGQWRVNRJEE-UHFFFAOYSA-N 0.000 description 1
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical class CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
238000002525 ultrasonication Methods 0.000 description 1
238000010200 validation analysis Methods 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)
Cephalosporin Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP19598584A 1984-01-13 1984-09-18 ７−ホルミルアミノ−セフエム化合物およびその製造法 Granted JPS6172789A (ja)

Priority Applications (7)

Application Number	Priority Date	Filing Date	Title
JP19598584A JPS6172789A (ja)	1984-09-18	1984-09-18	７−ホルミルアミノ−セフエム化合物およびその製造法
DE8484115168T DE3481769D1 (de)	1984-01-23	1984-12-11	Cephemderivate und ihre herstellung.
EP84115168A EP0150378B1 (de)	1984-01-23	1984-12-11	Cephemderivate und ihre Herstellung
AT84115168T ATE51403T1 (de)	1984-01-23	1984-12-11	Cephemderivate und ihre herstellung.
US06/681,784 US4723004A (en)	1984-01-23	1984-12-14	Cephem compounds
CA000470115A CA1297056C (en)	1984-01-23	1984-12-14	Cephem compounds and their production
KR1019840007985A KR930000276B1 (ko)	1984-01-13	1984-12-15	세펨 화합물의 제조방법

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP19598584A JPS6172789A (ja)	1984-09-18	1984-09-18	７−ホルミルアミノ−セフエム化合物およびその製造法

Publications (2)

Publication Number	Publication Date
JPS6172789A JPS6172789A (ja)	1986-04-14
JPH0477754B2 true JPH0477754B2 (de)	1992-12-09

Family

ID=16350292

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP19598584A Granted JPS6172789A (ja)	1984-01-13	1984-09-18	７−ホルミルアミノ−セフエム化合物およびその製造法

Country Status (1)

Country	Link
JP (1)	JPS6172789A (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP2010285566A (ja) *	2009-06-13	2010-12-24	Ozeki Koichi	石鹸及びその製造方法

1984
- 1984-09-18 JP JP19598584A patent/JPS6172789A/ja active Granted

Also Published As

Publication number	Publication date
JPS6172789A (ja)	1986-04-14

Publication	Publication Date	Title
JPS6320520B2 (de)	1988-04-27
JPH0527395B2 (de)	1993-04-21
JPS6133558B2 (de)	1986-08-02
JPH0477754B2 (de)	1992-12-09
GB2111495A (en)	1983-07-06	Aminoglycoside antibiotics
US4723004A (en)	1988-02-02	Cephem compounds
JPH0147479B2 (de)	1989-10-13
JPH0226957B2 (de)	1990-06-13
US4752469A (en)	1988-06-21	Potentiators of beta-lactam antibiotics
JPH022589B2 (de)	1990-01-18
EP0157544A2 (de)	1985-10-09	Antibiotika, deren Herstellung und Benutzung
JPH0341477B2 (de)	1991-06-24
US4950605A (en)	1990-08-21	FR-900493 substance, a process for its production and a pharmaceutical composition containing the same
US4264734A (en)	1981-04-28	Process for producing antibiotic desacetyl 890A10
JP3530563B2 (ja)	2004-05-24	Ｋｏ−８１１９物質及びその製造法
JPH0430400B2 (de)	1992-05-21
US4201769A (en)	1980-05-06	Antibiotic substances No. 17927A1 and No. 17927A2 and process for producing the same
JPH0429356B2 (de)	1992-05-18
JPH0582398B2 (de)	1993-11-18
JPH0361662B2 (de)	1991-09-20
CA1178548A (en)	1984-11-27	Homocitric acid oligoriboside derivative for prevention of dental caries
JPH0673465B2 (ja)	1994-09-21	ミルディオマイシンの製造法
JPH0439477B2 (de)	1992-06-29
WO1985000607A1 (en)	1985-02-14	Antibiotic tan-542 and process for its preparation
JPH0438399B2 (de)	1992-06-24