JPS6215556B2 - - Google Patents
Info
- Publication number
- JPS6215556B2 JPS6215556B2 JP52094651A JP9465177A JPS6215556B2 JP S6215556 B2 JPS6215556 B2 JP S6215556B2 JP 52094651 A JP52094651 A JP 52094651A JP 9465177 A JP9465177 A JP 9465177A JP S6215556 B2 JPS6215556 B2 JP S6215556B2
- Authority
- JP
- Japan
- Prior art keywords
- antibiotic
- solution
- bacteria
- culture
- manufactured
- 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
Links
- 150000003839 salts Chemical class 0.000 claims description 16
- MHSNTZYKSLYGOM-RKDXNWHRSA-N PS-5 Chemical compound C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)[C@H](CC)[C@H]21 MHSNTZYKSLYGOM-RKDXNWHRSA-N 0.000 description 127
- -1 trityl ester Chemical class 0.000 description 77
- 241000894006 Bacteria Species 0.000 description 73
- 239000000243 solution Substances 0.000 description 73
- 239000002609 medium Substances 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 56
- 230000000844 anti-bacterial effect Effects 0.000 description 54
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 48
- 238000006243 chemical reaction Methods 0.000 description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 42
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 40
- 102000006635 beta-lactamase Human genes 0.000 description 40
- 108090000204 Dipeptidase 1 Proteins 0.000 description 36
- 238000000034 method Methods 0.000 description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 32
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 32
- 239000003242 anti bacterial agent Substances 0.000 description 31
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
- 239000000843 powder Substances 0.000 description 27
- 229960003866 cefaloridine Drugs 0.000 description 26
- 230000002401 inhibitory effect Effects 0.000 description 26
- 235000002639 sodium chloride Nutrition 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- 229940088710 antibiotic agent Drugs 0.000 description 25
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 230000000694 effects Effects 0.000 description 24
- 238000012360 testing method Methods 0.000 description 24
- 229920001817 Agar Polymers 0.000 description 23
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 23
- 239000008272 agar Substances 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 20
- 239000002904 solvent Substances 0.000 description 20
- 239000000126 substance Substances 0.000 description 20
- 238000004809 thin layer chromatography Methods 0.000 description 20
- 238000003556 assay Methods 0.000 description 19
- 230000003115 biocidal effect Effects 0.000 description 19
- 239000007788 liquid Substances 0.000 description 18
- 229940056360 penicillin g Drugs 0.000 description 18
- 150000002148 esters Chemical group 0.000 description 17
- 230000005764 inhibitory process Effects 0.000 description 17
- 235000015097 nutrients Nutrition 0.000 description 17
- 238000000862 absorption spectrum Methods 0.000 description 16
- 159000000000 sodium salts Chemical class 0.000 description 16
- 239000007864 aqueous solution Substances 0.000 description 15
- 210000004556 brain Anatomy 0.000 description 15
- 239000000758 substrate Substances 0.000 description 15
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 238000002835 absorbance Methods 0.000 description 14
- 241000589519 Comamonas Species 0.000 description 13
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 13
- 238000010790 dilution Methods 0.000 description 13
- 239000012895 dilution Substances 0.000 description 13
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 12
- 241000588767 Proteus vulgaris Species 0.000 description 12
- 238000010521 absorption reaction Methods 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 235000008504 concentrate Nutrition 0.000 description 12
- 239000012141 concentrate Substances 0.000 description 12
- 235000019441 ethanol Nutrition 0.000 description 12
- 238000001802 infusion Methods 0.000 description 12
- 230000001954 sterilising effect Effects 0.000 description 12
- 238000004659 sterilization and disinfection Methods 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 230000001580 bacterial effect Effects 0.000 description 11
- 238000004166 bioassay Methods 0.000 description 11
- 238000010828 elution Methods 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000008363 phosphate buffer Substances 0.000 description 11
- 229940007042 proteus vulgaris Drugs 0.000 description 11
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 11
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 10
- 230000009102 absorption Effects 0.000 description 10
- 239000004480 active ingredient Substances 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 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 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 241000699670 Mus sp. Species 0.000 description 9
- 241000187180 Streptomyces sp. Species 0.000 description 9
- 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 9
- 239000000872 buffer Substances 0.000 description 9
- 239000003153 chemical reaction reagent Substances 0.000 description 9
- 238000012258 culturing Methods 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002156 mixing Methods 0.000 description 9
- 230000007935 neutral effect Effects 0.000 description 9
- 230000002829 reductive effect Effects 0.000 description 9
- 239000011780 sodium chloride Substances 0.000 description 9
- 241001453268 Comamonas terrigena Species 0.000 description 8
- 239000007983 Tris buffer Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000003782 beta lactam antibiotic agent Substances 0.000 description 8
- 238000001962 electrophoresis Methods 0.000 description 8
- 239000008103 glucose Substances 0.000 description 8
- 238000004816 paper chromatography Methods 0.000 description 8
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 8
- 241000894007 species Species 0.000 description 8
- 239000002132 β-lactam antibiotic Substances 0.000 description 8
- 229940124586 β-lactam antibiotics Drugs 0.000 description 8
- 150000003952 β-lactams Chemical class 0.000 description 8
- 229920002472 Starch Polymers 0.000 description 7
- 238000012474 bioautography Methods 0.000 description 7
- 230000004071 biological effect Effects 0.000 description 7
- 229910000019 calcium carbonate Inorganic materials 0.000 description 7
- 235000010216 calcium carbonate Nutrition 0.000 description 7
- 239000012153 distilled water Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 235000013312 flour Nutrition 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 230000012010 growth Effects 0.000 description 7
- 238000001727 in vivo Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000005259 measurement Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- 235000019698 starch Nutrition 0.000 description 7
- 241000186361 Actinobacteria <class> Species 0.000 description 6
- 235000010469 Glycine max Nutrition 0.000 description 6
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 229930182555 Penicillin Natural products 0.000 description 6
- 241000187747 Streptomyces Species 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000005273 aeration Methods 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 6
- 229960000723 ampicillin Drugs 0.000 description 6
- 238000005119 centrifugation Methods 0.000 description 6
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 description 6
- 238000000605 extraction Methods 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 238000001179 sorption measurement Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000006228 supernatant Substances 0.000 description 6
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 6
- FTOAOBMCPZCFFF-UHFFFAOYSA-N 5,5-diethylbarbituric acid Chemical compound CCC1(CC)C(=O)NC(=O)NC1=O FTOAOBMCPZCFFF-UHFFFAOYSA-N 0.000 description 5
- 241000186046 Actinomyces Species 0.000 description 5
- 241000588986 Alcaligenes Species 0.000 description 5
- 229930186147 Cephalosporin Natural products 0.000 description 5
- 241000588923 Citrobacter Species 0.000 description 5
- 241000192125 Firmicutes Species 0.000 description 5
- 239000001888 Peptone Substances 0.000 description 5
- 108010080698 Peptones Proteins 0.000 description 5
- 241000588769 Proteus <enterobacteria> Species 0.000 description 5
- 229920005654 Sephadex Polymers 0.000 description 5
- 239000012507 Sephadex™ Substances 0.000 description 5
- 241000936753 Streptomyces cremeus Species 0.000 description 5
- 241000958209 Streptomyces flavidovirens Species 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 239000001913 cellulose Substances 0.000 description 5
- 229920002678 cellulose Polymers 0.000 description 5
- 229940124587 cephalosporin Drugs 0.000 description 5
- 150000001780 cephalosporins Chemical class 0.000 description 5
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 5
- 235000019797 dipotassium phosphate Nutrition 0.000 description 5
- 229910000396 dipotassium phosphate Inorganic materials 0.000 description 5
- 239000002552 dosage form Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 239000006916 nutrient agar Substances 0.000 description 5
- 235000019319 peptone Nutrition 0.000 description 5
- LWIHDJKSTIGBAC-UHFFFAOYSA-K potassium phosphate Substances [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 5
- 238000011218 seed culture Methods 0.000 description 5
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000193755 Bacillus cereus Species 0.000 description 4
- 241000194108 Bacillus licheniformis Species 0.000 description 4
- 108020004256 Beta-lactamase Proteins 0.000 description 4
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
- 108010010803 Gelatin Proteins 0.000 description 4
- 244000068988 Glycine max Species 0.000 description 4
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 4
- 108010087702 Penicillinase Proteins 0.000 description 4
- 241000191940 Staphylococcus Species 0.000 description 4
- WKDDRNSBRWANNC-ATRFCDNQSA-N Thienamycin Chemical compound C1C(SCCN)=C(C(O)=O)N2C(=O)[C@H]([C@H](O)C)[C@H]21 WKDDRNSBRWANNC-ATRFCDNQSA-N 0.000 description 4
- 230000007059 acute toxicity Effects 0.000 description 4
- 231100000403 acute toxicity Toxicity 0.000 description 4
- 239000012736 aqueous medium Substances 0.000 description 4
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 4
- 125000003460 beta-lactamyl group Chemical group 0.000 description 4
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000007423 decrease Effects 0.000 description 4
- SHFGJEQAOUMGJM-UHFFFAOYSA-N dialuminum dipotassium disodium dioxosilane iron(3+) oxocalcium oxomagnesium oxygen(2-) Chemical compound [O--].[O--].[O--].[O--].[O--].[O--].[O--].[O--].[Na+].[Na+].[Al+3].[Al+3].[K+].[K+].[Fe+3].[Fe+3].O=[Mg].O=[Ca].O=[Si]=O SHFGJEQAOUMGJM-UHFFFAOYSA-N 0.000 description 4
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- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
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- WKDDRNSBRWANNC-UHFFFAOYSA-N Thienamycin Natural products C1C(SCCN)=C(C(O)=O)N2C(=O)C(C(O)C)C21 WKDDRNSBRWANNC-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 230000002378 acidificating effect Effects 0.000 description 3
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- MLYYVTUWGNIJIB-BXKDBHETSA-N cefazolin Chemical compound S1C(C)=NN=C1SCC1=C(C(O)=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 MLYYVTUWGNIJIB-BXKDBHETSA-N 0.000 description 3
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- 229960004592 isopropanol Drugs 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
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- 244000005700 microbiome Species 0.000 description 3
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- 239000003208 petroleum Substances 0.000 description 3
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- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229920001592 potato starch Polymers 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000600 sorbitol Substances 0.000 description 3
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- PKDBCJSWQUOKDO-UHFFFAOYSA-M 2,3,5-triphenyltetrazolium chloride Chemical compound [Cl-].C1=CC=CC=C1C(N=[N+]1C=2C=CC=CC=2)=NN1C1=CC=CC=C1 PKDBCJSWQUOKDO-UHFFFAOYSA-M 0.000 description 2
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (24)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9465177A JPS5430195A (en) | 1977-08-09 | 1977-08-09 | Antibiotic substance ps-5 having beta-lactamase inhibiting activity, its derivative and their preparation |
| GR55463A GR62185B (en) | 1977-03-31 | 1978-02-15 | Preparation process of an antibiotic ps-5 and its derivatives with inhibitory activity of b-lactamase |
| IL54118A IL54118A (en) | 1977-03-31 | 1978-02-23 | Antibiotic ps-5 and derivatives having -lactamase inhibitory activity,production tehreof and antibiotic compositions containing them |
| FI780671A FI59813C (fi) | 1977-03-31 | 1978-02-28 | Foerfarande foer framstaellning av antibiotikumet ps-5 och salter daerav med en beta-laktamas inhiberande aktivitet |
| US05/882,730 US4318916A (en) | 1977-03-31 | 1978-03-02 | Antibiotic PS-5 and derivatives having β-lactamase inhibitory activity and production thereof |
| GB9338/78A GB1598062A (en) | 1977-03-31 | 1978-03-09 | Antibiotic and its antibacterial derivatives |
| NL7802976A NL7802976A (nl) | 1977-03-31 | 1978-03-20 | Antibioticum ps-5 en derivaten daarvan met (beta)-lactamase-remwerking en werkwijze ter be- reiding daarvan. |
| NO781076A NO781076L (no) | 1977-03-31 | 1978-03-29 | Antibiotikum ps-5 og derivater av dette med beta-laktamasehemmende aktivitet samt fremgangsmaate for dets fremstilling |
| AR271592A AR219738A1 (es) | 1977-03-31 | 1978-03-29 | Procedimiento para la obtencion de acido 3-(2-acetilamino etiltio)-6-etil-7-oxo-1-azabiciclo (3. 2. 0.) hept-2- en-2-carboxilico y derivados que tienen actividad antibiotica e inhibitoria de beta-lactamasa |
| AU34592/78A AU518781B2 (en) | 1977-03-31 | 1978-03-30 | 7-OXO-l-AZABICYCLO 3. 2. 0 HEPT-2-ENE-2-CARBOXYLIC ACID DERIVATIVES |
| CA300,097A CA1123767A (en) | 1977-03-31 | 1978-03-30 | Antibiotic ps-5 and derivatives having beta-lactamase inhibitory activity and production thereof |
| IT21748/78A IT1113066B (it) | 1977-03-31 | 1978-03-30 | Antibiotico ps-5 e suoi derivati aventi attivita' inibitoria della beta-lattamasi e loro produzione |
| SE7803623A SE7803623L (sv) | 1977-03-31 | 1978-03-30 | Antibiotikum ps-5 och derivat derav samt forfarande for framstellning derav |
| NZ186830A NZ186830A (en) | 1977-03-31 | 1978-03-30 | Antibiotic ps-5 and derivatives(2-carboxy-6-ethyl-3-substituted-1-azabicyclo (3,2,0) hept-2-en-7-ones) and pharmaceutical compostions |
| CH340678A CH643262A5 (de) | 1977-03-31 | 1978-03-30 | Antibioticum mit betalactamasehemmender wirksamkeit sowie verfahren zu ihrer herstellung. |
| AT224578A AT362059B (de) | 1977-03-31 | 1978-03-30 | Verfahren zur herstellung eines neuen antibiotikums und seiner derivate |
| IE638/78A IE46369B1 (en) | 1977-03-31 | 1978-03-30 | Novel antiobitoic and its antibacterial derivatives |
| PT67848A PT67848B (en) | 1977-03-31 | 1978-03-30 | Process for preparing a novel antibiotic and its derivatives having beta-lactamase inihbitory activity |
| LU79351A LU79351A1 (fr) | 1977-03-31 | 1978-03-31 | Procede de preparation d'un nouvel antibiotique et de ses derives |
| DE19782813922 DE2813922A1 (de) | 1977-03-31 | 1978-03-31 | Antibiotikum ps-5-verbindungen, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von bakteriellen infektionen |
| DK143678A DK144098C (da) | 1977-03-31 | 1978-03-31 | Fremgangsmaade til fremstilling af antibiotikum ps-5 eller salte eller estere deraf |
| FR7809644A FR2408608B1 (fr) | 1977-03-31 | 1978-03-31 | Nouvel antibiotique denomme ps-5 et ses derives doues d'activite inhibitrice de la b-lactamase et leur procede de preparation |
| AT18980A AT362506B (de) | 1977-03-31 | 1980-01-15 | Verfahren zur herstellung von neuen ester- derivaten eines antibiotikums |
| FI801352A FI801352A (fi) | 1977-03-31 | 1980-04-28 | Foerfarande foer framstaellning av estrar av antibioten ps-5 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP9465177A JPS5430195A (en) | 1977-08-09 | 1977-08-09 | Antibiotic substance ps-5 having beta-lactamase inhibiting activity, its derivative and their preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5430195A JPS5430195A (en) | 1979-03-06 |
| JPS6215556B2 true JPS6215556B2 (de) | 1987-04-08 |
Family
ID=14116150
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP9465177A Granted JPS5430195A (en) | 1977-03-31 | 1977-08-09 | Antibiotic substance ps-5 having beta-lactamase inhibiting activity, its derivative and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5430195A (de) |
-
1977
- 1977-08-09 JP JP9465177A patent/JPS5430195A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5430195A (en) | 1979-03-06 |
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