DE1967083C2 - Arzneimittel mit antibiotischer Wirkung auf der Basis einer Kombination aus (-)-α-Amino-p-hydroxybenzylpenicillin und Flucloxacillin - Google Patents
Arzneimittel mit antibiotischer Wirkung auf der Basis einer Kombination aus (-)-α-Amino-p-hydroxybenzylpenicillin und FlucloxacillinInfo
- Publication number
- DE1967083C2 DE1967083C2 DE1967083A DE1967083A DE1967083C2 DE 1967083 C2 DE1967083 C2 DE 1967083C2 DE 1967083 A DE1967083 A DE 1967083A DE 1967083 A DE1967083 A DE 1967083A DE 1967083 C2 DE1967083 C2 DE 1967083C2
- Authority
- DE
- Germany
- Prior art keywords
- penicillin
- penicillins
- acid
- flucloxacillin
- amino
- 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
- 229960004273 floxacillin Drugs 0.000 title claims description 33
- UIOFUWFRIANQPC-JKIFEVAISA-N Floxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(F)C=CC=C1Cl UIOFUWFRIANQPC-JKIFEVAISA-N 0.000 title claims description 31
- 230000003115 biocidal effect Effects 0.000 title claims description 7
- 229940126601 medicinal product Drugs 0.000 title claims 2
- 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 28
- 239000000203 mixture Substances 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 18
- 230000000694 effects Effects 0.000 claims description 18
- 229930182555 Penicillin Natural products 0.000 claims description 17
- 244000052616 bacterial pathogen Species 0.000 claims description 15
- 229960000723 ampicillin Drugs 0.000 claims description 12
- 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 claims description 12
- 229940056360 penicillin g Drugs 0.000 claims description 12
- 150000002960 penicillins Chemical class 0.000 claims description 12
- 241000588769 Proteus <enterobacteria> Species 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims description 9
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims description 9
- JGSARLDLIJGVTE-UHFFFAOYSA-N 3,3-dimethyl-7-oxo-6-[(2-phenylacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-UHFFFAOYSA-N 0.000 claims description 7
- 241000894006 Bacteria Species 0.000 claims description 6
- 108010087702 Penicillinase Proteins 0.000 claims description 6
- 229940049954 penicillin Drugs 0.000 claims description 6
- 229950009506 penicillinase Drugs 0.000 claims description 6
- 238000001228 spectrum Methods 0.000 claims description 6
- 241000295644 Staphylococcaceae Species 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 5
- 241000588914 Enterobacter Species 0.000 claims description 4
- 241000589517 Pseudomonas aeruginosa Species 0.000 claims description 4
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 230000000844 anti-bacterial effect Effects 0.000 claims description 4
- 241000192125 Firmicutes Species 0.000 claims description 3
- 241000607768 Shigella Species 0.000 claims description 3
- 229960003326 cloxacillin Drugs 0.000 claims description 3
- 241000588748 Klebsiella Species 0.000 claims description 2
- LQOLIRLGBULYKD-JKIFEVAISA-N cloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl LQOLIRLGBULYKD-JKIFEVAISA-N 0.000 claims description 2
- 229960001585 dicloxacillin Drugs 0.000 claims description 2
- YFAGHNZHGGCZAX-JKIFEVAISA-N dicloxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=C(Cl)C=CC=C1Cl YFAGHNZHGGCZAX-JKIFEVAISA-N 0.000 claims description 2
- 235000019371 penicillin G benzathine Nutrition 0.000 claims description 2
- 229930195708 Penicillin V Natural products 0.000 claims 5
- 229940056367 penicillin v Drugs 0.000 claims 5
- BPLBGHOLXOTWMN-MBNYWOFBSA-N phenoxymethylpenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)COC1=CC=CC=C1 BPLBGHOLXOTWMN-MBNYWOFBSA-N 0.000 claims 5
- 229960003672 propicillin Drugs 0.000 claims 4
- 229960004894 pheneticillin Drugs 0.000 claims 3
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 claims 2
- 230000010933 acylation Effects 0.000 claims 2
- 238000005917 acylation reaction Methods 0.000 claims 2
- 241000607142 Salmonella Species 0.000 claims 1
- 230000004071 biological effect Effects 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 230000007547 defect Effects 0.000 claims 1
- 230000007812 deficiency Effects 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 229960003085 meticillin Drugs 0.000 claims 1
- 230000002906 microbiologic effect Effects 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- 229960000515 nafcillin Drugs 0.000 claims 1
- GPXLMGHLHQJAGZ-JTDSTZFVSA-N nafcillin Chemical compound C1=CC=CC2=C(C(=O)N[C@@H]3C(N4[C@H](C(C)(C)S[C@@H]43)C(O)=O)=O)C(OCC)=CC=C21 GPXLMGHLHQJAGZ-JTDSTZFVSA-N 0.000 claims 1
- 229940071462 oralone Drugs 0.000 claims 1
- NONJJLVGHLVQQM-JHXYUMNGSA-N phenethicillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C(C)OC1=CC=CC=C1 NONJJLVGHLVQQM-JHXYUMNGSA-N 0.000 claims 1
- 239000002243 precursor Substances 0.000 claims 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims 1
- 229960003022 amoxicillin Drugs 0.000 description 42
- 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 42
- 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 41
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 32
- 239000000243 solution Substances 0.000 description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Natural products C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- -1 isoxazolyl penicillins Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 241000588724 Escherichia coli Species 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 159000000000 sodium salts Chemical class 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 5
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
- KWGRBVOPPLSCSI-WPRPVWTQSA-N (-)-ephedrine Chemical compound CN[C@@H](C)[C@H](O)C1=CC=CC=C1 KWGRBVOPPLSCSI-WPRPVWTQSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000002195 synergetic effect Effects 0.000 description 4
- 241000606125 Bacteroides Species 0.000 description 3
- 235000001258 Cinchona calisaya Nutrition 0.000 description 3
- 241000588915 Klebsiella aerogenes Species 0.000 description 3
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 3
- 241000588772 Morganella morganii Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- 241000293871 Salmonella enterica subsp. enterica serovar Typhi Species 0.000 description 3
- 241000607760 Shigella sonnei Species 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 229940088710 antibiotic agent Drugs 0.000 description 3
- LFYJSSARVMHQJB-QIXNEVBVSA-N bakuchiol Chemical compound CC(C)=CCC[C@@](C)(C=C)\C=C\C1=CC=C(O)C=C1 LFYJSSARVMHQJB-QIXNEVBVSA-N 0.000 description 3
- 229960003669 carbenicillin Drugs 0.000 description 3
- 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 3
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 3
- 230000002349 favourable effect Effects 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229960000948 quinine Drugs 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229940115939 shigella sonnei Drugs 0.000 description 3
- 229960004659 ticarcillin Drugs 0.000 description 3
- 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 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 241000588923 Citrobacter Species 0.000 description 2
- 241000588919 Citrobacter freundii Species 0.000 description 2
- 241000588722 Escherichia 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
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 2
- 241000588770 Proteus mirabilis Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 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
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 150000004684 trihydrates Chemical class 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- WNPVZANXRCPJPW-UHFFFAOYSA-N 5-[isocyano-(4-methylphenyl)sulfonylmethyl]-1,2,3-trimethoxybenzene Chemical compound COC1=C(OC)C(OC)=CC(C([N+]#[C-])S(=O)(=O)C=2C=CC(C)=CC=2)=C1 WNPVZANXRCPJPW-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 241000606124 Bacteroides fragilis Species 0.000 description 1
- 241000588697 Enterobacter cloacae Species 0.000 description 1
- 241000588921 Enterobacteriaceae Species 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000606790 Haemophilus Species 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 206010021703 Indifference Diseases 0.000 description 1
- 241000568687 Isabella mirabilis Species 0.000 description 1
- 241000588747 Klebsiella pneumoniae Species 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000588767 Proteus vulgaris Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 description 1
- 241000607762 Shigella flexneri Species 0.000 description 1
- HEMHJVSKTPXQMS-DYCDLGHISA-M Sodium hydroxide-d Chemical compound [Na+].[2H][O-] HEMHJVSKTPXQMS-DYCDLGHISA-M 0.000 description 1
- 241001221452 Staphylococcus faecalis Species 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 241001467018 Typhis Species 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- BQCLJECBJVWSES-UHFFFAOYSA-N acetyl chloride;hydrochloride Chemical compound Cl.CC(Cl)=O BQCLJECBJVWSES-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- KWGRBVOPPLSCSI-UHFFFAOYSA-N d-ephedrine Natural products CNC(C)C(O)C1=CC=CC=C1 KWGRBVOPPLSCSI-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229960002179 ephedrine Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 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
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
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- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 229940076266 morganella morganii Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 229960001019 oxacillin Drugs 0.000 description 1
- UWYHMGVUTGAWSP-JKIFEVAISA-N oxacillin Chemical compound N([C@@H]1C(N2[C@H](C(C)(C)S[C@@H]21)C(O)=O)=O)C(=O)C1=C(C)ON=C1C1=CC=CC=C1 UWYHMGVUTGAWSP-JKIFEVAISA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- YCOFRPYSZKIPBQ-UHFFFAOYSA-N penicillic acid Natural products COC1=CC(=O)OC1(O)C(C)=C YCOFRPYSZKIPBQ-UHFFFAOYSA-N 0.000 description 1
- VOUGEZYPVGAPBB-UHFFFAOYSA-N penicillin acid Natural products OC(=O)C=C(OC)C(=O)C(C)=C VOUGEZYPVGAPBB-UHFFFAOYSA-N 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/21—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a nitrogen atom directly attached in position 6 and 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
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB40319/68A GB1241844A (en) | 1968-08-23 | 1968-08-23 | Penicillins |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE1967083A1 DE1967083A1 (de) | 1977-03-17 |
| DE1967083C2 true DE1967083C2 (de) | 1986-10-02 |
Family
ID=10414312
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967083A Expired DE1967083C2 (de) | 1968-08-23 | 1969-08-21 | Arzneimittel mit antibiotischer Wirkung auf der Basis einer Kombination aus (-)-α-Amino-p-hydroxybenzylpenicillin und Flucloxacillin |
| DE1967313A Expired DE1967313C2 (de) | 1968-08-23 | 1969-08-21 | Verwendung von (-)-α-Amino-p-hydroxybenzylpenicillin-trihydrat zur Herstellung eines Arzneimittels in oraler Applikationsform zur Bekämpfung bakterieller Infektionen des Menschen |
| DE1942693A Expired DE1942693C2 (de) | 1968-08-23 | 1969-08-21 | Verfahren zur Herstellung von (-)-α-Amino-p-hydroxybenzylpenicillintrihydrat |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1967313A Expired DE1967313C2 (de) | 1968-08-23 | 1969-08-21 | Verwendung von (-)-α-Amino-p-hydroxybenzylpenicillin-trihydrat zur Herstellung eines Arzneimittels in oraler Applikationsform zur Bekämpfung bakterieller Infektionen des Menschen |
| DE1942693A Expired DE1942693C2 (de) | 1968-08-23 | 1969-08-21 | Verfahren zur Herstellung von (-)-α-Amino-p-hydroxybenzylpenicillintrihydrat |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US3674776A (show.php) |
| BE (1) | BE737848A (show.php) |
| BR (1) | BR6911795D0 (show.php) |
| CA (1) | CA1012136B (show.php) |
| CH (1) | CH542878A (show.php) |
| CY (1) | CY1081A (show.php) |
| DE (3) | DE1967083C2 (show.php) |
| DK (1) | DK127000C (show.php) |
| ES (1) | ES370756A1 (show.php) |
| FI (2) | FI50425B (show.php) |
| FR (1) | FR2016283B1 (show.php) |
| GB (1) | GB1241844A (show.php) |
| HK (1) | HK56080A (show.php) |
| IE (1) | IE33574B1 (show.php) |
| IL (1) | IL32844A (show.php) |
| KE (1) | KE3073A (show.php) |
| MY (1) | MY8100196A (show.php) |
| NL (1) | NL6912905A (show.php) |
| OA (1) | OA03164A (show.php) |
| RO (1) | RO56335A (show.php) |
| SE (2) | SE383634B (show.php) |
| YU (1) | YU37168B (show.php) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873521A (en) * | 1970-09-17 | 1975-03-25 | Astra Laekemedel Ab | Esters of {60 -amino penicillins |
| US4203972A (en) * | 1971-11-01 | 1980-05-20 | Astra Pharmaceutical Products, Inc. | Penicillin composition |
| GB1413516A (en) * | 1972-10-06 | 1975-11-12 | Leo Pharm Prod Ltd | Crystalline pivaloyloxymethal d - -alpha- aminobenzylpenicillinate |
| GB1465694A (en) * | 1973-05-15 | 1977-02-23 | Beecham Group Ltd | Preparation of penicillin salts |
| US3932386A (en) * | 1973-06-18 | 1976-01-13 | American Home Products Corporation | Sodium 6-(L-aminocyclohexane carboxamido)penicillanic acid |
| GB1494902A (en) * | 1974-05-09 | 1977-12-14 | Glaxo Lab Ltd | Penicillins |
| US3985747A (en) * | 1974-05-24 | 1976-10-12 | Bristol-Myers Company | Crystalline sesquihydrate of 7-[D-α-amino-α-(p-hydroxyphenyl)acetamido]-3-(1,2,3-triazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid |
| ES436565A1 (es) * | 1974-06-05 | 1977-04-01 | Bristol Myers Co | Un procedimiento para la preparacion de acidos acetamidope- nicilanicos. |
| US3925418A (en) * | 1974-06-19 | 1975-12-09 | Bristol Myers Co | Hemisolvate of D-(-)-2-(p-hydroxyphenyl)glycyl chloride hydrochloride and process |
| US3969524A (en) * | 1974-08-13 | 1976-07-13 | Hoffmann-La Roche Inc. | Stable amoxicillin dosage form |
| AU8364875A (en) * | 1974-08-21 | 1977-02-10 | Hoffmann La Roche | Choline and n-methyl-d-glucamine salts of amoxycillin |
| GB1463563A (en) * | 1974-10-10 | 1977-02-02 | Beecham Group Ltd | Pharmaceutical compositions |
| GB1523278A (en) * | 1974-10-21 | 1978-08-31 | Gist Brocades Nv | Penicillanic acid derivatives |
| JPS5186116A (en) * | 1975-01-20 | 1976-07-28 | Takeda Chemical Industries Ltd | Dd arufua isobuchirusuruhobenjirupenishirinhanyobaiwabutsuketsushono seizoho |
| GB1532993A (en) * | 1975-03-07 | 1978-11-22 | Beecham Group Ltd | Injectable antibiotic compositions |
| GB1578337A (en) * | 1976-05-13 | 1980-11-05 | Beecham Group Ltd | Amoxycillin composition |
| GB1527557A (en) * | 1976-07-07 | 1978-10-04 | Beecham Group Ltd | Process for preparing solid sodium amoxycillin |
| GB1576731A (en) * | 1976-08-10 | 1980-10-15 | Beecham Group Ltd | Process for the preparation of sodium amoxycillin |
| JPS5736298Y2 (show.php) * | 1977-06-27 | 1982-08-11 | ||
| DE2749203C2 (de) | 1977-11-03 | 1981-12-17 | Riedel-De Haen Ag, 3016 Seelze | Verfahren zur Racematspaltung von DL-alpha-Aminocarbonsäuren und diastereomere Salze |
| NZ189945A (en) * | 1978-04-01 | 1981-04-24 | Beecham Group Ltd | Ampicillin phthalidyl ester naphthalene 2-sulphonate also pharmaceutical compositions |
| US4240960A (en) * | 1979-03-19 | 1980-12-23 | Bristol-Myers Company | Trimethylsilyl substituted penicillins |
| US4278600A (en) * | 1979-03-19 | 1981-07-14 | Bristol-Myers Company | Production of penicillins |
| US4310458A (en) * | 1979-03-19 | 1982-01-12 | Bristol-Myers Company | Production of penicillins |
| IT1113934B (it) | 1979-05-03 | 1986-01-27 | Chimica Bulciago Srl | Procedimento perfezionato di clorurazione del gruppo carbossilico di alfa-amminoacidi |
| US4351766A (en) * | 1979-07-12 | 1982-09-28 | Bristol-Myers Company | Production of penicillins |
| IT1193836B (it) | 1979-11-02 | 1988-08-24 | Dobfar Spa | Procedimento per la produzione di acido 6-d-alfa-amino-p-idrossifenilacetamido enicillanico |
| IE51516B1 (en) * | 1980-10-06 | 1987-01-07 | Leo Pharm Prod Ltd | 1,1-dioxapenicillanoyloxymethyl 6-(d-alpha-amino-alpha-phenylacetamido)penicillanate napsylate |
| KR820001564B1 (ko) * | 1981-05-09 | 1982-09-02 | 동신제약 주식회사 | 새로운 실릴화제를 이용한 세팔로스포린 유도체의 제조방법 |
| EP0131147B2 (en) * | 1983-06-10 | 1996-12-04 | Beecham Group p.l.c. | Crystalline amoxycillin salt |
| JPS6248655A (ja) * | 1985-08-27 | 1987-03-03 | Kanegafuchi Chem Ind Co Ltd | Ｎ−〔１（ｓ）−エトキシカルボニル−３−フエニルプロピル〕−ｌ−アラニルクロリド無機酸塩及びその製造法 |
| JPS6379888A (ja) * | 1986-09-24 | 1988-04-09 | Tanabe Seiyaku Co Ltd | ペニシリン誘導体の安定型水和物 |
| GB9408117D0 (en) | 1994-04-23 | 1994-06-15 | Smithkline Beecham Corp | Pharmaceutical formulations |
| AT412213B (de) * | 2000-05-30 | 2004-11-25 | Sandoz Ag | Verfahren zur trocknung von amoxicillin oder amoxicillin-hältigen, oralen, festen pharmazeutischen zusammensetzungen unter verwendung eines gases mit einer definierten gasfeuchte |
| JP5113978B2 (ja) * | 2003-11-21 | 2013-01-09 | 味の素株式会社 | グルタミン酸誘導体の有機アミン塩及びその利用 |
| US7935377B2 (en) * | 2004-06-04 | 2011-05-03 | Ajinomoto Co., Inc. | Crystals of free (2R, 4R)-monatin and use thereof |
| FI20105572A0 (fi) | 2010-05-24 | 2010-05-24 | Prevab R Lcc | Muokattu beeta-laktamaasi ja siihen liittyvät menetelmät ja käytöt |
| US9290754B2 (en) | 2014-04-17 | 2016-03-22 | Synthetic Biologics Inc. | Beta-lactamases with improved properties for therapy |
| CN106574273B (zh) | 2014-08-28 | 2021-07-02 | 合成生物制品有限公司 | β-内酰胺酶的基于大肠杆菌的生产 |
| EP3204495B1 (en) | 2014-10-08 | 2020-04-22 | Synthetic Biologics, Inc. | Beta-lactamase formulations and uses thereof |
| US9744221B2 (en) | 2014-12-23 | 2017-08-29 | Synthetic Biologics, Inc. | Method and compositions for inhibiting or preventing adverse effects of oral antibiotics |
| CN104650119B (zh) * | 2015-02-10 | 2017-04-05 | 中国科学院长春应用化学研究所 | 一种β‑内酰胺化合物的制备方法 |
| CN107530406B (zh) | 2015-02-23 | 2021-10-22 | 合成生物制品有限公司 | 用于保护肠微生物群系的与抗生素一起使用的碳青霉烯酶 |
| US10709773B2 (en) | 2015-03-06 | 2020-07-14 | Synthetic Biologics, Inc. | Safe and effective beta-lactamase dosing for microbiome protection |
| CN116735514B (zh) * | 2023-08-11 | 2023-11-03 | 昆明理工大学 | 纳米酶结合液液微萃取快速检测天麻硫熏标志物的方法 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2985648A (en) * | 1958-10-06 | 1961-05-23 | Doyle Frank Peter | Alpha-aminobenzylpenicillins |
| DE1156078C2 (de) * | 1960-08-25 | 1973-10-25 | Beecham Res Lab | Verfahren zur Herstellung von D(-)-ª‡-Aminobenzylpenicillin und von L(+)-ª‡-Aminobenzylpenicillin |
| FR1332557A (fr) * | 1962-03-15 | 1963-07-19 | Bristol Myers Co | Procédé de fabrication d'alpha-amino-benzylpénicillines |
| BE639104A (show.php) * | 1962-11-02 | |||
| GB991586A (en) * | 1963-02-28 | 1965-05-12 | Beecham Res Lab | Process for the preparation of penicillins |
-
1968
- 1968-08-23 GB GB40319/68A patent/GB1241844A/en not_active Expired
-
1969
- 1969-08-18 US US851062A patent/US3674776A/en not_active Expired - Lifetime
- 1969-08-18 IL IL32844A patent/IL32844A/en unknown
- 1969-08-18 IE IE1172/69A patent/IE33574B1/xx unknown
- 1969-08-18 SE SE6911472A patent/SE383634B/xx unknown
- 1969-08-20 CY CY1081A patent/CY1081A/xx unknown
- 1969-08-21 DE DE1967083A patent/DE1967083C2/de not_active Expired
- 1969-08-21 DK DK449169A patent/DK127000C/da not_active IP Right Cessation
- 1969-08-21 DE DE1967313A patent/DE1967313C2/de not_active Expired
- 1969-08-21 DE DE1942693A patent/DE1942693C2/de not_active Expired
- 1969-08-22 BR BR211795/69A patent/BR6911795D0/pt unknown
- 1969-08-22 CH CH1280969A patent/CH542878A/de not_active IP Right Cessation
- 1969-08-22 FR FR6928824A patent/FR2016283B1/fr not_active Expired
- 1969-08-22 NL NL6912905A patent/NL6912905A/xx unknown
- 1969-08-22 ES ES370756A patent/ES370756A1/es not_active Expired
- 1969-08-22 FI FI2446/69A patent/FI50425B/fi active
- 1969-08-22 RO RO60866A patent/RO56335A/ro unknown
- 1969-08-22 BE BE737848D patent/BE737848A/xx not_active IP Right Cessation
- 1969-11-06 OA OA53775A patent/OA03164A/xx unknown
-
1974
- 1974-04-19 SE SE7405340A patent/SE432525B/xx not_active IP Right Cessation
-
1975
- 1975-12-05 YU YU3087/75A patent/YU37168B/xx unknown
-
1976
- 1976-09-28 CA CA262,207A patent/CA1012136B/xx not_active Expired
-
1979
- 1979-12-14 FI FI793921A patent/FI793921A7/fi not_active Application Discontinuation
-
1980
- 1980-08-15 KE KE3073A patent/KE3073A/xx unknown
- 1980-10-02 HK HK560/80A patent/HK56080A/xx unknown
-
1981
- 1981-12-30 MY MY196/81A patent/MY8100196A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| YU37168B (en) | 1984-08-31 |
| DE1967313C2 (de) | 1986-05-28 |
| FR2016283A1 (show.php) | 1970-05-08 |
| IL32844A (en) | 1973-02-28 |
| CA1012136B (en) | 1977-06-14 |
| YU308775A (en) | 1983-04-27 |
| HK56080A (en) | 1980-10-10 |
| BE737848A (show.php) | 1970-02-25 |
| FI793921A7 (fi) | 1981-01-01 |
| IE33574B1 (en) | 1974-08-21 |
| GB1241844A (en) | 1971-08-04 |
| OA03164A (fr) | 1970-12-15 |
| FR2016283B1 (show.php) | 1974-08-09 |
| IL32844A0 (en) | 1969-11-12 |
| DE1942693A1 (de) | 1970-02-26 |
| BR6911795D0 (pt) | 1973-01-11 |
| NL6912905A (show.php) | 1970-02-25 |
| MY8100196A (show.php) | 1981-12-31 |
| RO56335A (show.php) | 1974-11-11 |
| IE33574L (en) | 1970-02-23 |
| CH542878A (de) | 1973-10-15 |
| SE383634B (sv) | 1976-03-22 |
| DK127000C (da) | 1983-02-28 |
| CY1081A (en) | 1980-12-27 |
| ES370756A1 (es) | 1971-07-01 |
| FI50425B (show.php) | 1975-12-01 |
| DE1942693C2 (de) | 1984-03-08 |
| DE1967083A1 (de) | 1977-03-17 |
| SE432525B (sv) | 1984-04-09 |
| DK127000B (da) | 1973-09-10 |
| KE3073A (en) | 1980-08-29 |
| US3674776A (en) | 1972-07-04 |
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