CH641805A5 - Derivatives of 3-thio-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carbo xylic acid, process for their preparation and medicaments containing these compounds - Google Patents
Derivatives of 3-thio-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carbo xylic acid, process for their preparation and medicaments containing these compounds Download PDFInfo
- Publication number
- CH641805A5 CH641805A5 CH233978A CH233978A CH641805A5 CH 641805 A5 CH641805 A5 CH 641805A5 CH 233978 A CH233978 A CH 233978A CH 233978 A CH233978 A CH 233978A CH 641805 A5 CH641805 A5 CH 641805A5
- Authority
- CH
- Switzerland
- Prior art keywords
- compound
- formula
- salt
- salts
- fractions
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 236
- 238000000034 method Methods 0.000 title claims description 60
- 238000002360 preparation method Methods 0.000 title claims description 37
- 239000003814 drug Substances 0.000 title claims description 21
- 150000003839 salts Chemical class 0.000 claims description 114
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 114
- 159000000000 sodium salts Chemical class 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 38
- 229920005989 resin Polymers 0.000 claims description 29
- 239000011347 resin Substances 0.000 claims description 29
- 238000000855 fermentation Methods 0.000 claims description 24
- 230000004151 fermentation Effects 0.000 claims description 24
- -1 alkaline earth metal salts Chemical class 0.000 claims description 23
- 241000218589 Streptomyces olivaceus Species 0.000 claims description 16
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 230000008033 biological extinction Effects 0.000 claims description 14
- 230000007935 neutral effect Effects 0.000 claims description 13
- 239000003242 anti bacterial agent Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 229940088710 antibiotic agent Drugs 0.000 claims description 11
- 239000001963 growth medium Substances 0.000 claims description 10
- 239000004793 Polystyrene Substances 0.000 claims description 9
- 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 claims description 7
- FQQFFZPBGYGDSX-NJFHWYBASA-N epithienamycin E Chemical compound C1C(S\C=C\NC(C)=O)=C(C(O)=O)N2C(=O)[C@@H]([C@@H](OS(O)(=O)=O)C)[C@H]21 FQQFFZPBGYGDSX-NJFHWYBASA-N 0.000 claims description 7
- 238000013375 chromatographic separation Methods 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 229930186147 Cephalosporin Natural products 0.000 claims description 5
- 229930182555 Penicillin Natural products 0.000 claims description 5
- 239000002250 absorbent Substances 0.000 claims description 5
- 230000002745 absorbent Effects 0.000 claims description 5
- 229940124587 cephalosporin Drugs 0.000 claims description 5
- 150000001780 cephalosporins Chemical class 0.000 claims description 5
- 229920002223 polystyrene Polymers 0.000 claims description 5
- 239000000654 additive Substances 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 4
- 159000000001 potassium salts Chemical class 0.000 claims description 4
- 241000971017 Streptomyces gedanensis Species 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229940049954 penicillin Drugs 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims 1
- 230000000996 additive effect Effects 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 94
- 239000000243 solution Substances 0.000 description 60
- 230000002401 inhibitory effect Effects 0.000 description 49
- 239000008367 deionised water Substances 0.000 description 47
- 229910021641 deionized water Inorganic materials 0.000 description 47
- 239000011780 sodium chloride Substances 0.000 description 47
- 239000007787 solid Substances 0.000 description 39
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 38
- 229920001429 chelating resin Polymers 0.000 description 36
- 102000006635 beta-lactamase Human genes 0.000 description 34
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 30
- 239000000126 substance Substances 0.000 description 27
- 108090000204 Dipeptidase 1 Proteins 0.000 description 26
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 26
- 239000002609 medium Substances 0.000 description 23
- 230000002829 reductive effect Effects 0.000 description 23
- 238000004587 chromatography analysis Methods 0.000 description 21
- 238000002211 ultraviolet spectrum Methods 0.000 description 21
- 239000000706 filtrate Substances 0.000 description 18
- 239000007788 liquid Substances 0.000 description 18
- 239000001913 cellulose Substances 0.000 description 16
- 229920002678 cellulose Polymers 0.000 description 16
- 229920005654 Sephadex Polymers 0.000 description 15
- 239000012507 Sephadex™ Substances 0.000 description 15
- 229910001961 silver nitrate Inorganic materials 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical class [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 13
- 238000000746 purification Methods 0.000 description 13
- 241000588724 Escherichia coli Species 0.000 description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000003957 anion exchange resin Substances 0.000 description 12
- 101100313763 Arabidopsis thaliana TIM22-2 gene Proteins 0.000 description 11
- 239000008055 phosphate buffer solution Substances 0.000 description 11
- 229920002307 Dextran Polymers 0.000 description 10
- 238000001704 evaporation Methods 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000009102 absorption Effects 0.000 description 9
- 238000010521 absorption reaction Methods 0.000 description 9
- 230000000844 anti-bacterial effect Effects 0.000 description 9
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 8
- 108020004256 Beta-lactamase Proteins 0.000 description 8
- 241000589517 Pseudomonas aeruginosa Species 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000005342 ion exchange Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 7
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 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 7
- 241000588770 Proteus mirabilis Species 0.000 description 7
- 230000003115 biocidal effect Effects 0.000 description 7
- 235000010633 broth Nutrition 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 238000004108 freeze drying Methods 0.000 description 7
- 239000000499 gel Substances 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 229920002401 polyacrylamide Polymers 0.000 description 7
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 241000588697 Enterobacter cloacae Species 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- 235000019764 Soybean Meal Nutrition 0.000 description 6
- 239000002253 acid Substances 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
- 229940088598 enzyme Drugs 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000004455 soybean meal Substances 0.000 description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- 229960000723 ampicillin Drugs 0.000 description 5
- 239000003456 ion exchange resin Substances 0.000 description 5
- 229920003303 ion-exchange polymer Polymers 0.000 description 5
- 235000015097 nutrients Nutrition 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000011176 pooling Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 4
- 235000014469 Bacillus subtilis Nutrition 0.000 description 4
- 241000588748 Klebsiella Species 0.000 description 4
- 241000588915 Klebsiella aerogenes Species 0.000 description 4
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 4
- 239000002518 antifoaming agent Substances 0.000 description 4
- 239000007853 buffer solution Substances 0.000 description 4
- 229940125890 compound Ia Drugs 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- 244000063299 Bacillus subtilis Species 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000003463 adsorbent Substances 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin 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=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 3
- 238000005349 anion exchange Methods 0.000 description 3
- 238000009395 breeding Methods 0.000 description 3
- 230000001488 breeding effect Effects 0.000 description 3
- 239000012531 culture fluid Substances 0.000 description 3
- 238000011033 desalting Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000011049 filling Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000002054 inoculum Substances 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 239000008057 potassium phosphate buffer Substances 0.000 description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical class N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 101001057156 Homo sapiens Melanoma-associated antigen C2 Proteins 0.000 description 2
- 102100027252 Melanoma-associated antigen C2 Human genes 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- 241000607720 Serratia Species 0.000 description 2
- 241000607715 Serratia marcescens Species 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical class [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000009603 aerobic growth Effects 0.000 description 2
- 229960003022 amoxicillin Drugs 0.000 description 2
- 229960001139 cefazolin Drugs 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000010612 desalination reaction Methods 0.000 description 2
- 239000003792 electrolyte Substances 0.000 description 2
- 238000003306 harvesting Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 2
- 230000036961 partial effect Effects 0.000 description 2
- 235000019371 penicillin G benzathine Nutrition 0.000 description 2
- 229940056360 penicillin g Drugs 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 239000012064 sodium phosphate buffer Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 230000001954 sterilising effect Effects 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 229960005486 vaccine Drugs 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- VUDXUIMGYZQRKK-IONOHQLYSA-N Epithienamycin A Chemical compound C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)[C@@H]([C@@H](O)C)[C@H]21 VUDXUIMGYZQRKK-IONOHQLYSA-N 0.000 description 1
- PRPNUZWHFGSGRV-NJFHWYBASA-N Epithienamycin B Chemical compound C1C(S\C=C\NC(C)=O)=C(C(O)=O)N2C(=O)[C@@H]([C@@H](O)C)[C@H]21 PRPNUZWHFGSGRV-NJFHWYBASA-N 0.000 description 1
- VUDXUIMGYZQRKK-SKWCMTHISA-N Epithienamycin C Chemical compound C1C(SCCNC(C)=O)=C(C(O)=O)N2C(=O)[C@H]([C@@H](O)C)[C@H]21 VUDXUIMGYZQRKK-SKWCMTHISA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000588772 Morganella morganii Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000933812 Streptomyces flaveus Species 0.000 description 1
- 241000509474 Streptomyces flavovirens Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 229960003311 ampicillin trihydrate Drugs 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012062 aqueous buffer Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 125000003460 beta-lactamyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000003842 bromide salts Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000008366 buffered solution Substances 0.000 description 1
- SAQIIXUDKZKSPO-UHFFFAOYSA-N butan-1-ol;pyridine Chemical compound CCCCO.C1=CC=NC=C1 SAQIIXUDKZKSPO-UHFFFAOYSA-N 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 1
- 229960003669 carbenicillin Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000005341 cation exchange Methods 0.000 description 1
- 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 1
- 229960003866 cefaloridine Drugs 0.000 description 1
- 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 1
- FLKYBGKDCCEQQM-WYUVZMMLSA-M cefazolin sodium Chemical compound [Na+].S1C(C)=NN=C1SCC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)CN3N=NN=C3)[C@H]2SC1 FLKYBGKDCCEQQM-WYUVZMMLSA-M 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 229910052500 inorganic mineral Chemical class 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000011707 mineral Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003235 pyrrolidines Chemical class 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000011593 sulfur Chemical class 0.000 description 1
- 229910052717 sulfur Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OHKOGUYZJXTSFX-KZFFXBSXSA-N ticarcillin Chemical compound C=1([C@@H](C(O)=O)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)C=CSC=1 OHKOGUYZJXTSFX-KZFFXBSXSA-N 0.000 description 1
- 229960004659 ticarcillin Drugs 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000015192 vegetable juice Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
- C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
- C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 3
- C07D477/20—Sulfur atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Enzymes And Modification Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9366/77A GB1601688A (en) | 1977-03-05 | 1977-03-05 | 6-(1-hydroxyethyl)-7-oxo 1-aza bicyclo (3,2,0)-hept-2-ene-2-carboxylic acid derivatives and their use in pharmaceutical compositions |
| GB3283677 | 1977-08-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH641805A5 true CH641805A5 (en) | 1984-03-15 |
Family
ID=26242889
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH233978A CH641805A5 (en) | 1977-03-05 | 1978-03-03 | Derivatives of 3-thio-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carbo xylic acid, process for their preparation and medicaments containing these compounds |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS53116396A (da) |
| AU (1) | AU525142B2 (da) |
| CH (1) | CH641805A5 (da) |
| DE (1) | DE2808563A1 (da) |
| DK (1) | DK98478A (da) |
| ES (1) | ES467562A1 (da) |
| FR (1) | FR2401162A1 (da) |
| IE (1) | IE46736B1 (da) |
| IT (1) | IT7848280A0 (da) |
| NL (1) | NL7802356A (da) |
| SE (1) | SE7802462L (da) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4162323A (en) * | 1977-04-18 | 1979-07-24 | Merck & Co., Inc. | Antibiotic N-acetyl-dehydro-thienamycin |
| DE2966446D1 (en) * | 1978-09-09 | 1984-01-05 | Beecham Group Plc | Beta-lactam compounds, their preparation and use |
| DE3164021D1 (en) * | 1980-01-25 | 1984-07-19 | Beecham Group Plc | Beta-lactam containing compounds, their preparation and use |
| IN155384B (da) * | 1980-05-14 | 1985-01-19 | Pfizer | |
| JP4977670B2 (ja) * | 2008-09-11 | 2012-07-18 | 啓司 関口 | 生花整形器 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK143712C (da) * | 1975-11-21 | 1982-03-22 | Merck & Co Inc | Fremgangsmaade til fremstilling af de antibiotiske stoffer 890a1 og 890a3 |
| DK143713C (da) * | 1975-11-21 | 1982-03-08 | Merck & Co Inc | Fremgangsmaade til fremstilling af et antibiotisk stof n-acetyl-thienamycin og salte deraf |
| NL7704040A (nl) * | 1976-04-28 | 1977-11-01 | Merck & Co Inc | Werkwijze voor het bereiden van nieuwe anti- biotica. |
-
1978
- 1978-02-28 DE DE19782808563 patent/DE2808563A1/de not_active Withdrawn
- 1978-03-03 SE SE7802462A patent/SE7802462L/xx unknown
- 1978-03-03 IT IT7848280A patent/IT7848280A0/it unknown
- 1978-03-03 IE IE443/78A patent/IE46736B1/en unknown
- 1978-03-03 NL NL7802356A patent/NL7802356A/xx not_active Application Discontinuation
- 1978-03-03 JP JP2437578A patent/JPS53116396A/ja active Pending
- 1978-03-03 DK DK98478A patent/DK98478A/da unknown
- 1978-03-03 FR FR7806154A patent/FR2401162A1/fr active Granted
- 1978-03-03 CH CH233978A patent/CH641805A5/de not_active IP Right Cessation
- 1978-03-03 ES ES467562A patent/ES467562A1/es not_active Expired
- 1978-03-03 AU AU33841/78A patent/AU525142B2/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| IE46736B1 (en) | 1983-09-07 |
| IE780443L (en) | 1978-09-05 |
| DE2808563A1 (de) | 1978-09-07 |
| IT7848280A0 (it) | 1978-03-03 |
| FR2401162A1 (fr) | 1979-03-23 |
| AU3384178A (en) | 1979-09-06 |
| JPS53116396A (en) | 1978-10-11 |
| FR2401162B1 (da) | 1980-08-29 |
| SE7802462L (sv) | 1978-09-06 |
| AU525142B2 (en) | 1982-10-21 |
| NL7802356A (nl) | 1978-09-07 |
| DK98478A (da) | 1978-09-06 |
| ES467562A1 (es) | 1980-05-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2560074C2 (de) | Verfahren zur Gewinnung von Clavulansäure und deren Salze | |
| DE2552638C3 (de) | Thienamycin, Verfahren zu seiner Herstellung und Thienamycin enthaltende Arzneimittel | |
| CH638194A5 (de) | Esterastin, eine neue physiologisch wirksame substanz und deren herstellung. | |
| DE2718782C2 (da) | ||
| DE19807972A1 (de) | Lipopeptidantibiotika-Calciumsalze, Verfahren zu ihrer Herstellung und Verwendung | |
| US4006060A (en) | Thienamycin production | |
| DE69628002T2 (de) | Herstellung von clavunalat-salzen | |
| CH624956A5 (de) | Verfahren zur entfernung von verunreinigungen aus clavulansaeure. | |
| CH627494A5 (de) | Verfahren zur herstellung eines neuen antibioticums. | |
| DE69633330T2 (de) | Verfahren zur herstellung von pharmazeutisch verträglichen salzen der clavulansäure | |
| CH641805A5 (en) | Derivatives of 3-thio-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carbo xylic acid, process for their preparation and medicaments containing these compounds | |
| SU1039446A3 (ru) | Способ получени антибиотического комплекса | |
| DE2652677C2 (de) | Antibiotica 890A&darr;1&darr; und 890A&darr;3&darr;, Verfahren zu ihrer Herstellung und diese Antibiotika enthaltende antibakterielle Mittel | |
| DE2839668C2 (da) | ||
| DE2513854C2 (de) | Neue Antibiotika, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| DE1952317A1 (de) | 3-Phosphat-Ester von Lincomycin,dessen Analysen und Celestin sowie Verfahren zu deren Herstellung | |
| DE2652681C2 (de) | N-Acetylthienamycin, Verfahren zu seiner Herstellung und diese Verbindung enthaltende Mittel | |
| US4304867A (en) | Culture of Streptomyces cattleya | |
| DE2553927C3 (de) | An der Spermidin-Seitenkette N-terminal substituierte Derivate von Antibioticum BM 123 γ und Verfahren zu deren Herstellung | |
| DE2641908A1 (de) | Antibiotisch wirksame substanzen, mimosamycin und chlorocarcin a, b und c und verfahren zu ihrer herstellung | |
| DE1617899A1 (de) | Lydimycin und Verfahren zu seiner Gewinnung | |
| DE2751260A1 (de) | Antibiotikum 890 a tief 9 | |
| DE2039990C2 (de) | Neue Antibiotika B-5050 A bis F (Maridomycin I bis VI), Verfahren zu ihrer Herstellung und ihre pharmazeutische Zubereitung | |
| DE2944143C2 (de) | Antibiotikum SF-2052, Verfahren zu dessen Herstellung und das Antibiotikum SF-2052 enthaltende antibakterielle Mittel | |
| DE2905066C2 (de) | Antibiotikum SF-2050B, Verfahren zur Herstellung desselben und antibakterielle Mittel, welche dasselbe enthalten |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |