CH651571A5 - Penamcarbonsaeure-derivate, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten. - Google Patents

Penamcarbonsaeure-derivate, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten. Download PDF

Info

Publication number: CH651571A5
Authority: CH; Switzerland
Prior art keywords: acid; compound; ester; formula; pharmaceutically acceptable
Prior art date: 1980-01-21

Application number

CH374/81A

Other languages

German (de)

English (en)

Inventor

William J Gottstein

Original Assignee

Bristol Myers Co

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1980-01-21

Filing date

1981-01-21

Publication date

1985-09-30

1980-12-11 Priority claimed from US06/214,833 external-priority patent/US4340539A/en

1981-01-21 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1985-09-30 Publication of CH651571A5 publication Critical patent/CH651571A5/de

Links

150000001875 compounds Chemical class 0.000 title claims description 82
238000000034 method Methods 0.000 title claims description 17
238000004519 manufacturing process Methods 0.000 title claims description 6
150000004649 carbonic acid derivatives Chemical class 0.000 title 1
239000008177 pharmaceutical agent Substances 0.000 title 1
239000000203 mixture Substances 0.000 claims description 71
239000002253 acid Substances 0.000 claims description 47
-1 acetoxymethyl Chemical group 0.000 claims description 46
150000002148 esters Chemical class 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 34
239000000460 chlorine Substances 0.000 claims description 22
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 18
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 claims description 18
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 18
229960003022 amoxicillin Drugs 0.000 claims description 17
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 claims description 17
239000003782 beta lactam antibiotic agent Substances 0.000 claims description 14
239000002132 β-lactam antibiotic Substances 0.000 claims description 14
229940124586 β-lactam antibiotics Drugs 0.000 claims description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
229910052739 hydrogen Inorganic materials 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 13
102000006635 beta-lactamase Human genes 0.000 claims description 12
108090000204 Dipeptidase 1 Proteins 0.000 claims description 9
229960000583 acetic acid Drugs 0.000 claims description 8
229960000723 ampicillin Drugs 0.000 claims description 8
229910052763 palladium Inorganic materials 0.000 claims description 8
241000894006 Bacteria Species 0.000 claims description 7
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 7
239000003054 catalyst Substances 0.000 claims description 7
239000012362 glacial acetic acid Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
238000005984 hydrogenation reaction Methods 0.000 claims description 6
239000003085 diluting agent Substances 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
230000000844 anti-bacterial effect Effects 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052801 chlorine Chemical group 0.000 claims description 3
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 3
229910052725 zinc Inorganic materials 0.000 claims description 3
XAKBSHICSHRJCL-UHFFFAOYSA-N [CH2]C(=O)C1=CC=CC=C1 Chemical group [CH2]C(=O)C1=CC=CC=C1 XAKBSHICSHRJCL-UHFFFAOYSA-N 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
230000000694 effects Effects 0.000 claims description 2
150000004967 organic peroxy acids Chemical class 0.000 claims description 2
238000007254 oxidation reaction Methods 0.000 claims description 2
230000002401 inhibitory effect Effects 0.000 claims 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 100
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 87
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 76
239000000243 solution Substances 0.000 description 75
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
229910001868 water Inorganic materials 0.000 description 69
GMJQFFRLFJLBSC-XJNRBXITSA-M potassium;(2s,3s,5r)-3-(chloromethyl)-3-methyl-4,4,7-trioxo-4$l^{6}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [K+].O=S1(=O)[C@](C)(CCl)[C@H](C([O-])=O)N2C(=O)C[C@H]21 GMJQFFRLFJLBSC-XJNRBXITSA-M 0.000 description 61
238000001914 filtration Methods 0.000 description 29
238000003756 stirring Methods 0.000 description 27
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 22
239000000706 filtrate Substances 0.000 description 22
150000003462 sulfoxides Chemical class 0.000 description 22
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
238000004458 analytical method Methods 0.000 description 20
239000007787 solid Substances 0.000 description 20
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 18
239000000047 product Substances 0.000 description 18
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
229910052938 sodium sulfate Inorganic materials 0.000 description 17
235000011152 sodium sulphate Nutrition 0.000 description 17
241000588724 Escherichia coli Species 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
229920006395 saturated elastomer Polymers 0.000 description 16
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 14
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 13
239000010410 layer Substances 0.000 description 13
229940125898 compound 5 Drugs 0.000 description 12
239000002002 slurry Substances 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
238000010992 reflux Methods 0.000 description 11
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 10
235000017557 sodium bicarbonate Nutrition 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
239000003781 beta lactamase inhibitor Substances 0.000 description 9
229940126813 beta-lactamase inhibitor Drugs 0.000 description 9
239000013078 crystal Substances 0.000 description 9
229910052700 potassium Inorganic materials 0.000 description 9
239000011591 potassium Substances 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000011734 sodium Substances 0.000 description 9
239000002904 solvent Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 8
230000036765 blood level Effects 0.000 description 8
238000002329 infrared spectrum Methods 0.000 description 8
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
239000008346 aqueous phase Substances 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
239000012074 organic phase Substances 0.000 description 7
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 7
235000011007 phosphoric acid Nutrition 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
241000699670 Mus sp. Species 0.000 description 6
KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
229910000147 aluminium phosphate Inorganic materials 0.000 description 6
150000003863 ammonium salts Chemical class 0.000 description 6
238000001035 drying Methods 0.000 description 6
239000002024 ethyl acetate extract Substances 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000007788 liquid Substances 0.000 description 6
229910052757 nitrogen Inorganic materials 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
238000005406 washing Methods 0.000 description 6
229940126085 β‑Lactamase Inhibitor Drugs 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 5
239000005909 Kieselgur Substances 0.000 description 5
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
125000000217 alkyl group Chemical group 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 5
238000001953 recrystallisation Methods 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000012258 stirred mixture Substances 0.000 description 5
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 4
VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
125000003710 aryl alkyl group Chemical group 0.000 description 4
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
150000002431 hydrogen Chemical group 0.000 description 4
SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000003208 petroleum Substances 0.000 description 4
239000012071 phase Substances 0.000 description 4
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
238000006748 scratching Methods 0.000 description 4
230000002393 scratching effect Effects 0.000 description 4
235000009518 sodium iodide Nutrition 0.000 description 4
150000003457 sulfones Chemical class 0.000 description 4
QFLWZFQWSBQYPS-AWRAUJHKSA-N (3S)-3-[[(2S)-2-[[(2S)-2-[5-[(3aS,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-[1-bis(4-chlorophenoxy)phosphorylbutylamino]-4-oxobutanoic acid Chemical compound CCCC(NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@@H](NC(=O)CCCCC1SC[C@@H]2NC(=O)N[C@H]12)C(C)C)P(=O)(Oc1ccc(Cl)cc1)Oc1ccc(Cl)cc1 QFLWZFQWSBQYPS-AWRAUJHKSA-N 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 3
CLMSHAWYULIVFQ-UHFFFAOYSA-N 3-bromo-3h-2-benzofuran-1-one Chemical compound C1=CC=C2C(Br)OC(=O)C2=C1 CLMSHAWYULIVFQ-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 3
208000035143 Bacterial infection Diseases 0.000 description 3
108020004256 Beta-lactamase Proteins 0.000 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
208000022362 bacterial infectious disease Diseases 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
238000009835 boiling Methods 0.000 description 3
238000001816 cooling Methods 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
239000012065 filter cake Substances 0.000 description 3
239000012442 inert solvent Substances 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000002054 inoculum Substances 0.000 description 3
238000001990 intravenous administration Methods 0.000 description 3
239000002808 molecular sieve Substances 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
150000004965 peroxy acids Chemical class 0.000 description 3
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
QMWWAEFYIXXXQW-UHFFFAOYSA-M potassium;2-[(4-ethoxy-4-oxobut-2-en-2-yl)amino]-2-phenylacetate Chemical compound [K+].CCOC(=O)C=C(C)NC(C([O-])=O)C1=CC=CC=C1 QMWWAEFYIXXXQW-UHFFFAOYSA-M 0.000 description 3
229940002612 prodrug Drugs 0.000 description 3
239000000651 prodrug Substances 0.000 description 3
125000006239 protecting group Chemical group 0.000 description 3
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000003826 tablet Substances 0.000 description 3
230000001225 therapeutic effect Effects 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 2
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
241000606124 Bacteroides fragilis Species 0.000 description 2
241000606123 Bacteroides thetaiotaomicron Species 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
229930186147 Cephalosporin Chemical class 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000588697 Enterobacter cloacae Species 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
229930182555 Penicillin Natural products 0.000 description 2
229920005654 Sephadex Polymers 0.000 description 2
239000012507 Sephadex™ Substances 0.000 description 2
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 2
241000191967 Staphylococcus aureus Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
LFGGBJMSXWHYCN-UHFFFAOYSA-N [K].CCCCC(CC)CC(O)=O Chemical compound [K].CCCCC(CC)CC(O)=O LFGGBJMSXWHYCN-UHFFFAOYSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
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ACBDNFPUXYGKPT-UHFFFAOYSA-N bromomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCBr ACBDNFPUXYGKPT-UHFFFAOYSA-N 0.000 description 2
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125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
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238000000338 in vitro Methods 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
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ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007937 lozenge Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 2
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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230000003000 nontoxic effect Effects 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
150000002960 penicillins Chemical class 0.000 description 2
150000002978 peroxides Chemical class 0.000 description 2
125000005633 phthalidyl group Chemical group 0.000 description 2
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239000012286 potassium permanganate Substances 0.000 description 2
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BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical class OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
241000588772 Morganella morganii Species 0.000 description 1
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HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
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125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 description 1
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239000013543 active substance Substances 0.000 description 1
239000008272 agar Substances 0.000 description 1
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125000003545 alkoxy group Chemical group 0.000 description 1
229940024554 amdinocillin Drugs 0.000 description 1
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230000002945 anti-bacteroids Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
239000006286 aqueous extract Substances 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
125000004104 aryloxy group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
ZYASDBCEYAHPMS-UHFFFAOYSA-N bis(chloromethyl) sulfate Chemical compound ClCOS(=O)(=O)OCCl ZYASDBCEYAHPMS-UHFFFAOYSA-N 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
SLAYUXIURFNXPG-CRAIPNDOSA-N ceforanide Chemical compound NCC1=CC=CC=C1CC(=O)N[C@@H]1C(=O)N2C(C(O)=O)=C(CSC=3N(N=NN=3)CC(O)=O)CS[C@@H]21 SLAYUXIURFNXPG-CRAIPNDOSA-N 0.000 description 1
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239000003610 charcoal Substances 0.000 description 1
BWWVAEOLVKTZFQ-ISVUSNJMSA-N chembl530 Chemical compound N(/[C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)=C\N1CCCCCC1 BWWVAEOLVKTZFQ-ISVUSNJMSA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
PJBIHXWYDMFGCV-UHFFFAOYSA-N chloro(chlorosulfonyloxy)methane Chemical compound ClCOS(Cl)(=O)=O PJBIHXWYDMFGCV-UHFFFAOYSA-N 0.000 description 1
BULLHNJGPPOUOX-UHFFFAOYSA-N chloroacetone Chemical compound CC(=O)CCl BULLHNJGPPOUOX-UHFFFAOYSA-N 0.000 description 1
OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 1
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HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 description 1
229960003324 clavulanic acid Drugs 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
239000012059 conventional drug carrier Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
238000001514 detection method Methods 0.000 description 1
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
238000007865 diluting Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
239000003480 eluent Substances 0.000 description 1
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230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 1
XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
SLFUXNFVAANERW-UHFFFAOYSA-N ethyl hexanoate;potassium Chemical compound [K].CCCCCC(=O)OCC SLFUXNFVAANERW-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
210000001035 gastrointestinal tract Anatomy 0.000 description 1
239000011521 glass Substances 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000013067 intermediate product Substances 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
159000000003 magnesium salts Chemical class 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000004682 monohydrates Chemical class 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
239000008024 pharmaceutical diluent Substances 0.000 description 1
LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
SHUZOJHMOBOZST-UHFFFAOYSA-N phylloquinone Natural products CC(C)CCCCC(C)CCC(C)CCCC(=CCC1=C(C)C(=O)c2ccccc2C1=O)C SHUZOJHMOBOZST-UHFFFAOYSA-N 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
229960004919 procaine Drugs 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
210000002966 serum Anatomy 0.000 description 1
229910001961 silver nitrate Inorganic materials 0.000 description 1
229910001923 silver oxide Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
241000894007 species Species 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
150000003568 thioethers Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
238000001291 vacuum drying Methods 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
235000019168 vitamin K Nutrition 0.000 description 1
239000011712 vitamin K Substances 0.000 description 1
150000003721 vitamin K derivatives Chemical class 0.000 description 1
229940046010 vitamin k Drugs 0.000 description 1
150000003952 β-lactams Chemical class 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Steroid Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Cephalosporin Compounds (AREA)

CH374/81A 1980-01-21 1981-01-21 Penamcarbonsaeure-derivate, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten. CH651571A5 (de)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
US11389480A	1980-01-21	1980-01-21
US21483180A	1980-12-11	1980-12-11
US06/214,833 US4340539A (en)	1980-01-21	1980-12-11	Derivatives of 6-bromo penicillanic acid

Publications (1)

Publication Number	Publication Date
CH651571A5 true CH651571A5 (de)	1985-09-30

Family

ID=27381401

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
CH374/81A CH651571A5 (de)	1980-01-21	1981-01-21	Penamcarbonsaeure-derivate, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten.
CH1284/84A CH649087A5 (de)	1980-01-21	1981-01-21	6-alpha-brompenicillansaeureester, ihre sulfoxide und sulfone.

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
CH1284/84A CH649087A5 (de)	1980-01-21	1981-01-21	6-alpha-brompenicillansaeureester, ihre sulfoxide und sulfone.

Country Status (12)

Country	Link
KR (1)	KR850001066B1 (sv)
CA (1)	CA1175807A (sv)
CH (2)	CH651571A5 (sv)
DE (1)	DE3101527A1 (sv)
DK (3)	DK162717C (sv)
GB (1)	GB2070592B (sv)
HU (2)	HU184380B (sv)
IL (1)	IL61880A (sv)
NL (1)	NL8100209A (sv)
NO (5)	NO160298C (sv)
OA (1)	OA06748A (sv)
SE (5)	SE455702B (sv)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
ZA826687B (en) *	1981-09-14	1983-07-27	Pfizer	Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl 5(r)penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor
ATE27772T1 (de) *	1983-09-15	1987-07-15	Bristol Myers Co	Pharmazeutische zusammensetzungen zur bekaempfung des widerstands von bakterien enthaltenden anaerobien.
GB2157286B (en) *	1984-04-12	1987-12-31	Leo Pharm Prod Ltd	B-lactam antibiotic potentiators

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IN149747B (sv) *	1977-06-07	1982-04-03	Pfizer
DE2912511C2 (de) *	1977-06-07	1982-06-24	Pfizer Inc., 10017 New York, N.Y.	Pharmazeutische Zusammensetzung, enthaltend Penicillansäure
IE49880B1 (en) *	1979-02-13	1986-01-08	Leo Pharm Prod Ltd	Penicillin derivatives
GB2045236A (en) *	1979-03-26	1980-10-29	Hoechst Uk Ltd	Oxapenem derivatives
US4244951A (en) *	1979-05-16	1981-01-13	Pfizer Inc.	Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide

1981
- 1981-01-08 IL IL61880A patent/IL61880A/xx unknown
- 1981-01-15 CA CA000368537A patent/CA1175807A/en not_active Expired
- 1981-01-16 NL NL8100209A patent/NL8100209A/xx not_active Application Discontinuation
- 1981-01-16 GB GB8101365A patent/GB2070592B/en not_active Expired
- 1981-01-19 DE DE19813101527 patent/DE3101527A1/de not_active Withdrawn
- 1981-01-19 DK DK021881A patent/DK162717C/da not_active IP Right Cessation
- 1981-01-20 HU HU81115A patent/HU184380B/hu not_active IP Right Cessation
- 1981-01-20 HU HU833171A patent/HU188606B/hu not_active IP Right Cessation
- 1981-01-20 NO NO810166A patent/NO160298C/no unknown
- 1981-01-21 SE SE8100339A patent/SE455702B/sv not_active IP Right Cessation
- 1981-01-21 CH CH374/81A patent/CH651571A5/de not_active IP Right Cessation
- 1981-01-21 CH CH1284/84A patent/CH649087A5/de not_active IP Right Cessation
- 1981-02-19 OA OA57331A patent/OA06748A/xx unknown
1984
- 1984-07-21 KR KR1019840004326A patent/KR850001066B1/ko not_active IP Right Cessation
1985
- 1985-05-08 SE SE8502285A patent/SE8502285L/sv not_active Application Discontinuation
- 1985-05-08 SE SE8502286A patent/SE466203B/sv not_active IP Right Cessation
- 1985-09-03 NO NO85853450A patent/NO161677C/no unknown
1986
- 1986-05-16 NO NO86861944A patent/NO164298C/no unknown
- 1986-05-16 NO NO86861945A patent/NO164299C/no unknown
- 1986-05-16 NO NO86861946A patent/NO164300C/no unknown
1990
- 1990-01-19 SE SE9000190A patent/SE9000190L/sv not_active Application Discontinuation
- 1990-01-19 SE SE9000189A patent/SE9000189L/sv not_active Application Discontinuation
- 1990-11-30 DK DK285790A patent/DK162769C/da not_active IP Right Cessation
- 1990-11-30 DK DK285890A patent/DK164938C/da not_active IP Right Cessation

Also Published As

Publication number	Publication date
DE3101527A1 (de)	1982-02-18
DK162717C (da)	1992-04-21
SE8502285D0 (sv)	1985-05-08
NO164298B (no)	1990-06-11
HU188606B (en)	1986-04-28
NO853450L (no)	1981-07-22
NO161677C (no)	1989-09-13
OA06748A (fr)	1982-06-30
SE8100339L (sv)	1981-09-01
NO160298C (no)	1989-04-05
CH649087A5 (de)	1985-04-30
DK162717B (da)	1991-12-02
NO861944L (no)	1981-07-22
SE8502286L (sv)	1985-05-08
GB2070592A (en)	1981-09-09
SE9000190L (sv)	1991-07-20
DK21881A (da)	1981-07-22
SE9000189L (sv)	1991-07-20
NO160298B (no)	1988-12-27
KR850001066B1 (ko)	1985-07-25
DK164938B (da)	1992-09-14
SE466203B (sv)	1992-01-13
IL61880A (en)	1984-11-30
SE8502286D0 (sv)	1985-05-08
DK285790A (da)	1990-11-30
NO164299C (no)	1990-09-19
KR850001465A (ko)	1985-03-18
NO861946L (no)	1981-07-22
GB2070592B (en)	1983-05-11
SE9000189D0 (sv)	1990-01-19
NO164300C (no)	1990-09-19
SE455702B (sv)	1988-08-01
DK285890D0 (da)	1990-11-30
SE8502285L (sv)	1985-05-08
DK162769C (da)	1992-04-27
NO861945L (no)	1981-07-22
HU184380B (en)	1984-08-28
NL8100209A (nl)	1981-08-17
NO810166L (no)	1981-07-22
SE9000190D0 (sv)	1990-01-19
DK164938C (da)	1993-02-01
CA1175807A (en)	1984-10-09
DK162769B (da)	1991-12-09
DK285790D0 (da)	1990-11-30
NO164299B (no)	1990-06-11
DK285890A (da)	1990-11-30
NO164298C (no)	1990-09-19
NO161677B (no)	1989-06-05
NO164300B (no)	1990-06-11

Publication	Publication Date	Title
DE3005164C2 (de)	1986-06-26	1,1-Dioxopenicillanoyloxymethyl-6-(D-&alpha;-amino-&alpha;-phenylacetamido)-penicillanat, Verfahren zu seiner Herstellung und es enthaltendes Arzneimittel
DE2824535A1 (de)	1978-12-14	Penicillansaeure-1,1-dioxide, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
CH628901A5 (de)	1982-03-31	Verfahren zur herstellung von cephalosporinantibiotika.
DE2448966A1 (de)	1975-04-30	Penicillinderivate
DE2312042A1 (de)	1974-01-03	Cephalosporine und verfahren zu deren herstellung
DE1670625A1 (de)	1970-08-06	7-alpha-Aminobenzyl-3-methylcephalosporinanaloge und ihre Herstellung
DE2461526C2 (de)	1984-11-22	N-Acylderivate von &alpha;-Aminobenzylpenicillinen
CH628057A5 (de)	1982-02-15	Verfahren zur herstellung eines cephalosporin-derivates.
DE2155081A1 (de)	1972-05-10	Neue heterocyclische Verbindungen
DE1670324B2 (de)	1977-03-10	7-cyanacetylamino-cephalosporansaeurederivate
DE69133273T2 (de)	2004-05-13	Antibakterielle Penem-Ester-Derivate
DE3035259C2 (de)	1986-03-13	Cephalosporinverbindungen, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten
DE2311005A1 (de)	1973-10-31	Beta-lactamderivate, verfahren zu deren herstellung und sie enthaltende pharmazeutische mittel
DE2056983B2 (de)	1979-11-15	S-Heterocyclylthiomethyl-Cephalosporine, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutische Präparate
CH651571A5 (de)	1985-09-30	Penamcarbonsaeure-derivate, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten.
DE3008257A1 (de)	1980-09-11	Verfahren zur herstellung von penicillansaeure-1,1-dioxid und dessen estern sowie zwischenstufen zur durchfuehrung des verfahrens
CH648850A5 (de)	1985-04-15	Penicillansaeure-derivate, verfahren zu ihrer herstellung und solche derivate enthaltende arzneimittel.
DE2055531C3 (de)	1982-02-25	Amidinopenicillansäurederivate, Verfahren zur Herstellung dieser Verbindungen und ihre Verwendung bei der Bekämpfung von Infektionskrankheiten
DE2715038A1 (de)	1977-11-24	Neue antibakterielle verbindungen
CH628055A5 (en)	1982-02-15	Process for the preparation of clavamic acid derivatives
DE2128605A1 (de)	1971-12-23	Neue Cephalosporansäurederivaten und Verfahren zu ihrer Herstellung
CH646176A5 (de)	1984-11-15	Beta-lactam-antibiotika mit beta-lactamase-hemmwirkung.
JPH0368035B2 (sv)	1991-10-25
DD279882A5 (de)	1990-06-20	6-beta-(substituierte)-(s)-hydroxymethyl-penicillan-saeuren und derivate derselben
AT309684B (de)	1973-08-27	Verfahren zur Herstellung von neuen Penicillinen und Cephalosporinen

Legal Events

Date	Code	Title	Description
1994-09-30	PL	Patent ceased
2024-10-31	PL	Patent ceased