BE846094A - Nouvelles penicillines et leurs procedes de preparation - Google Patents

Nouvelles penicillines et leurs procedes de preparation

Info

Publication number: BE846094A
Authority: BE; Belgium
Prior art keywords: emi; compound; group; solvent; acid
Prior art date: 1975-09-12

Application number

BE170545A

Other languages

English (en)

French (fr)

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.)

1975-09-12

Filing date

1976-09-10

Publication date

1977-03-10

1975-09-12 Priority claimed from GB37525/75A external-priority patent/GB1533413A/en

1975-12-27 Priority claimed from JP15787475A external-priority patent/JPS5283393A/ja

1975-12-27 Priority claimed from JP15787375A external-priority patent/JPS5283392A/ja

1975-12-29 Priority claimed from JP15792075A external-priority patent/JPS5283491A/ja

1976-09-10 Application filed filed Critical

1977-03-10 Publication of BE846094A publication Critical patent/BE846094A/fr

Links

229930182555 Penicillin Natural products 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 5
150000002960 penicillins Chemical class 0.000 title description 6
-1 propionamido Chemical group 0.000 claims description 209
239000000203 mixture Substances 0.000 claims description 99
239000002904 solvent Substances 0.000 claims description 96
150000001875 compounds Chemical class 0.000 claims description 88
239000002253 acid Substances 0.000 claims description 85
238000006243 chemical reaction Methods 0.000 claims description 73
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 44
125000006239 protecting group Chemical group 0.000 claims description 35
239000000843 powder Substances 0.000 claims description 30
150000002148 esters Chemical class 0.000 claims description 28
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 26
150000003839 salts Chemical class 0.000 claims description 26
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 21
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
238000000034 method Methods 0.000 claims description 21
MIDXCONKKJTLDX-UHFFFAOYSA-N 3,5-dimethylcyclopentane-1,2-dione Chemical compound CC1CC(C)C(=O)C1=O MIDXCONKKJTLDX-UHFFFAOYSA-N 0.000 claims description 20
235000013736 caramel Nutrition 0.000 claims description 19
125000003282 alkyl amino group Chemical group 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 16
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
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 13
125000003545 alkoxy group Chemical group 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 12
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 12
238000006482 condensation reaction Methods 0.000 claims description 11
239000011541 reaction mixture Substances 0.000 claims description 10
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 10
150000001540 azides Chemical class 0.000 claims description 9
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 9
229910052763 palladium Inorganic materials 0.000 claims description 9
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 9
229910052500 inorganic mineral Inorganic materials 0.000 claims description 8
239000011707 mineral Substances 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
150000001412 amines Chemical class 0.000 claims description 7
230000000845 anti-microbial effect Effects 0.000 claims description 7
AEOCXXJPGCBFJA-UHFFFAOYSA-N ethionamide Chemical compound CCC1=CC(C(N)=S)=CC=N1 AEOCXXJPGCBFJA-UHFFFAOYSA-N 0.000 claims description 7
125000000217 alkyl group Chemical group 0.000 claims description 6
238000009833 condensation Methods 0.000 claims description 6
230000005494 condensation Effects 0.000 claims description 6
229910052698 phosphorus Inorganic materials 0.000 claims description 6
239000011574 phosphorus Substances 0.000 claims description 6
150000003573 thiols Chemical class 0.000 claims description 6
241001465754 Metazoa Species 0.000 claims description 5
150000002463 imidates Chemical class 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims description 5
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
229940049954 penicillin Drugs 0.000 claims description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 3
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 claims description 2
PHSPJQZRQAJPPF-UHFFFAOYSA-N N-alpha-Methylhistamine Chemical compound CNCCC1=CN=CN1 PHSPJQZRQAJPPF-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims 6
239000008194 pharmaceutical composition Substances 0.000 claims 6
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims 6
230000001225 therapeutic effect Effects 0.000 claims 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims 3
HCXJFMDOHDNDCC-UHFFFAOYSA-N 5-$l^{1}-oxidanyl-3,4-dihydropyrrol-2-one Chemical group O=C1CCC(=O)[N]1 HCXJFMDOHDNDCC-UHFFFAOYSA-N 0.000 claims 3
235000019253 formic acid Nutrition 0.000 claims 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
230000008030 elimination Effects 0.000 claims 2
238000003379 elimination reaction Methods 0.000 claims 2
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 2
ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 claims 1
230000002378 acidificating effect Effects 0.000 claims 1
125000006309 butyl amino group Chemical group 0.000 claims 1
239000003610 charcoal Substances 0.000 claims 1
125000004663 dialkyl amino group Chemical group 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
JMQGGPRJQOQKRT-UHFFFAOYSA-N diphenyl hydrogen phosphate;azide Chemical compound [N-]=[N+]=[N-].C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 JMQGGPRJQOQKRT-UHFFFAOYSA-N 0.000 claims 1
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
RNGGTCZLJZVJDO-UHFFFAOYSA-N formic acid;zinc Chemical compound [Zn].OC=O RNGGTCZLJZVJDO-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
125000004888 n-propyl amino group Chemical group [H]N(*)C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 claims 1
239000002023 wood Substances 0.000 claims 1
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 169
239000000243 solution Substances 0.000 description 141
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 99
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 84
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 75
238000000862 absorption spectrum Methods 0.000 description 64
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 42
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
239000000741 silica gel Substances 0.000 description 35
229910002027 silica gel Inorganic materials 0.000 description 35
238000004809 thin layer chromatography Methods 0.000 description 35
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 33
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
239000002244 precipitate Substances 0.000 description 26
QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 25
MHLMRBVCMNDOCW-UHFFFAOYSA-N acetic acid;butan-1-ol;hydrate Chemical compound O.CC(O)=O.CCCCO MHLMRBVCMNDOCW-UHFFFAOYSA-N 0.000 description 24
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 22
238000001914 filtration Methods 0.000 description 22
RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 description 22
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 20
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 19
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
235000002639 sodium chloride Nutrition 0.000 description 18
229910000027 potassium carbonate Inorganic materials 0.000 description 17
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 15
230000002829 reductive effect Effects 0.000 description 15
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 15
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
239000007864 aqueous solution Substances 0.000 description 10
239000013078 crystal Substances 0.000 description 10
239000000284 extract Substances 0.000 description 10
NTNKNFHIAFDCSJ-UHFFFAOYSA-N (2-nitrophenyl) thiohypochlorite Chemical compound [O-][N+](=O)C1=CC=CC=C1SCl NTNKNFHIAFDCSJ-UHFFFAOYSA-N 0.000 description 9
229960002317 succinimide Drugs 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 description 8
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 8
238000003756 stirring Methods 0.000 description 8
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 7
229940056360 penicillin g Drugs 0.000 description 7
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 6
NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000007810 chemical reaction solvent Substances 0.000 description 6
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 6
239000003960 organic solvent Substances 0.000 description 6
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000002198 insoluble material Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
159000000000 sodium salts Chemical class 0.000 description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
241000894006 Bacteria Species 0.000 description 3
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 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
125000003368 amide group Chemical group 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
239000012043 crude product Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
MADOXCFISYCULS-UHFFFAOYSA-N octyl 2-sulfanylacetate Chemical compound CCCCCCCCOC(=O)CS MADOXCFISYCULS-UHFFFAOYSA-N 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000011591 potassium Substances 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
230000003389 potentiating effect Effects 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
SCYCMFQAMTUOEU-ZCFIWIBFSA-N (2r)-4-amino-2-[(2-nitrophenyl)sulfanylazaniumyl]-4-oxobutanoate Chemical compound NC(=O)C[C@H](C(O)=O)NSC1=CC=CC=C1[N+]([O-])=O SCYCMFQAMTUOEU-ZCFIWIBFSA-N 0.000 description 2
OWHSTLLOZWTNTQ-UHFFFAOYSA-N 2-ethylhexyl 2-sulfanylacetate Chemical compound CCCCC(CC)COC(=O)CS OWHSTLLOZWTNTQ-UHFFFAOYSA-N 0.000 description 2
LJCWONGJFPCTTL-SSDOTTSWSA-N D-4-hydroxyphenylglycine Chemical compound [O-]C(=O)[C@H]([NH3+])C1=CC=C(O)C=C1 LJCWONGJFPCTTL-SSDOTTSWSA-N 0.000 description 2
DCXYFEDJOCDNAF-UWTATZPHSA-N D-Asparagine Chemical compound OC(=O)[C@H](N)CC(N)=O DCXYFEDJOCDNAF-UWTATZPHSA-N 0.000 description 2
ZDXPYRJPNDTMRX-UHFFFAOYSA-N Glutamine Chemical compound OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
229930195708 Penicillin V Natural products 0.000 description 2
AZCVBVRUYHKWHU-MBNYWOFBSA-N Penicillin X Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-MBNYWOFBSA-N 0.000 description 2
241000589516 Pseudomonas Species 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
IGOWWWMCTJKWDA-UHFFFAOYSA-N acetic acid ethyl acetate oxolane Chemical compound C(C)(=O)O.C(C)(=O)OCC.O1CCCC1 IGOWWWMCTJKWDA-UHFFFAOYSA-N 0.000 description 2
WWCPCQUOGPJFAK-UHFFFAOYSA-N acetic acid;ethyl acetate;methanol Chemical compound OC.CC(O)=O.CCOC(C)=O WWCPCQUOGPJFAK-UHFFFAOYSA-N 0.000 description 2
NIYUAQURCFYKDP-UHFFFAOYSA-N acetic acid;oxolan-2-ylmethanol Chemical compound CC(O)=O.OCC1CCCO1 NIYUAQURCFYKDP-UHFFFAOYSA-N 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
238000005859 coupling reaction Methods 0.000 description 2
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
150000004820 halides Chemical class 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
244000005700 microbiome Species 0.000 description 2
235000010755 mineral Nutrition 0.000 description 2
235000019371 penicillin G benzathine Nutrition 0.000 description 2
229940056367 penicillin v Drugs 0.000 description 2
239000000825 pharmaceutical preparation Substances 0.000 description 2
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 description 2
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 2
ZUFQCVZBBNZMKD-UHFFFAOYSA-M potassium 2-ethylhexanoate Chemical compound [K+].CCCCC(CC)C([O-])=O ZUFQCVZBBNZMKD-UHFFFAOYSA-M 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
XSMMPWJOJBAIJP-MLGOLLRUSA-N (2R)-2-[[(2R)-4-amino-2-[(2-nitrophenyl)sulfanylamino]-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetic acid Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)SN[C@@H](C(=O)N[C@@H](C(=O)O)C1=CC=C(C=C1)O)CC(N)=O XSMMPWJOJBAIJP-MLGOLLRUSA-N 0.000 description 1
MPMICFFVWWGYJV-RXMQYKEDSA-N (2R)-2-amino-4-oxo-4-(propan-2-ylamino)butanoic acid Chemical compound CC(C)NC(=O)C[C@@H](N)C(O)=O MPMICFFVWWGYJV-RXMQYKEDSA-N 0.000 description 1
HDEOEHGOYQWGLY-SSDOTTSWSA-N (2R)-4-methoxy-2-[(2-nitrophenyl)sulfanylamino]-4-oxobutanoic acid Chemical compound [N+](=O)([O-])C1=C(C=CC=C1)SN[C@@H](C(=O)O)CC(=O)OC HDEOEHGOYQWGLY-SSDOTTSWSA-N 0.000 description 1
JJDXIPKAOYQAER-ZCFIWIBFSA-N (2r)-2-amino-4-(butylamino)-4-oxobutanoic acid Chemical compound CCCCNC(=O)C[C@@H](N)C(O)=O JJDXIPKAOYQAER-ZCFIWIBFSA-N 0.000 description 1
XBNYMUKWDRKOQG-MRVPVSSYSA-N (2r)-2-amino-4-(hexylamino)-4-oxobutanoic acid Chemical compound CCCCCCNC(=O)C[C@@H](N)C(O)=O XBNYMUKWDRKOQG-MRVPVSSYSA-N 0.000 description 1
QRBMPUYOGOCYDJ-AENDTGMFSA-N (2r)-2-amino-4-methoxy-4-oxobutanoic acid;hydrochloride Chemical compound Cl.COC(=O)C[C@@H](N)C(O)=O QRBMPUYOGOCYDJ-AENDTGMFSA-N 0.000 description 1
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
WGBMCNXICCIWCP-YFKPBYRVSA-N (2s)-4-amino-4-oxo-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CC(N)=O WGBMCNXICCIWCP-YFKPBYRVSA-N 0.000 description 1
JETQIUPBHQNHNZ-NJBDSQKTSA-N (2s,5r,6r)-3,3-dimethyl-7-oxo-6-[[(2r)-2-phenyl-2-sulfoacetyl]amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound C1([C@H](C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)S(O)(=O)=O)=CC=CC=C1 JETQIUPBHQNHNZ-NJBDSQKTSA-N 0.000 description 1
ACAZKHULUUVWCY-JFGNBEQYSA-N (2s,5r,6r)-6-(hexanoylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound S1C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](NC(=O)CCCCC)[C@H]21 ACAZKHULUUVWCY-JFGNBEQYSA-N 0.000 description 1
AMZJKFHHVQNUPT-JFGNBEQYSA-N (2s,5r,6r)-6-[(2-butylsulfanylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound S1C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](NC(=O)CSCCCC)[C@H]21 AMZJKFHHVQNUPT-JFGNBEQYSA-N 0.000 description 1
ADIHZDIWDRJIOQ-JFGNBEQYSA-N (2s,5r,6r)-6-[[2-(3-chlorobut-2-enylsulfanyl)acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound S1C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](NC(=O)CSCC=C(Cl)C)[C@H]21 ADIHZDIWDRJIOQ-JFGNBEQYSA-N 0.000 description 1
125000004973 1-butenyl group Chemical group C(=CCC)* 0.000 description 1
125000006017 1-propenyl group Chemical group 0.000 description 1
YBPAYPRLUDCSEY-UHFFFAOYSA-N 2-(4-hydroxyphenyl)acetamide Chemical compound NC(=O)CC1=CC=C(O)C=C1 YBPAYPRLUDCSEY-UHFFFAOYSA-N 0.000 description 1
CFRMVEKWKKDNAH-UHFFFAOYSA-N 2-amino-4-(methylamino)-4-oxobutanoic acid Chemical compound CNC(=O)CC(N)C(O)=O CFRMVEKWKKDNAH-UHFFFAOYSA-N 0.000 description 1
PSTLDOZKUHTZTD-UHFFFAOYSA-N 2-methyl-5h-1,2,4-thiadiazole-5-thiol Chemical compound CN1SC(S)N=C1 PSTLDOZKUHTZTD-UHFFFAOYSA-N 0.000 description 1
WXOMHOCWRMGOEH-OXQOHEQNSA-N 2-methylpropoxycarbonyl (2R)-2-[[(2R)-4-amino-2-[(2-nitrophenyl)sulfanylamino]-4-oxobutanoyl]amino]-2-(4-hydroxyphenyl)acetate Chemical compound C(C(C)C)OC(=O)OC([C@@H](C1=CC=C(C=C1)O)NC([C@@H](CC(N)=O)NSC1=C(C=CC=C1)[N+](=O)[O-])=O)=O WXOMHOCWRMGOEH-OXQOHEQNSA-N 0.000 description 1
QRRZDVHXGMVRIY-UHFFFAOYSA-N 3-amino-4-(ethylamino)-4-oxobutanoic acid Chemical compound CCNC(=O)C(N)CC(O)=O QRRZDVHXGMVRIY-UHFFFAOYSA-N 0.000 description 1
HGCDTPVHBZGXCA-UHFFFAOYSA-N 3-amino-4-oxo-4-(propylamino)butanoic acid Chemical compound CCCNC(=O)C(N)CC(O)=O HGCDTPVHBZGXCA-UHFFFAOYSA-N 0.000 description 1
XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 description 1
HDEOEHGOYQWGLY-UHFFFAOYSA-N 4-methoxy-2-[(2-nitrophenyl)sulfanylamino]-4-oxobutanoic acid Chemical compound COC(=O)CC(C(O)=O)NSC1=CC=CC=C1[N+]([O-])=O HDEOEHGOYQWGLY-UHFFFAOYSA-N 0.000 description 1
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 1
VUKCNAATVIWRTF-UHFFFAOYSA-N 4-oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid Chemical compound C=1C=CC=CC=1COC(=O)NC(C(=O)O)CC(=O)OCC1=CC=CC=C1 VUKCNAATVIWRTF-UHFFFAOYSA-N 0.000 description 1
UYOZWZKJQRBZRH-UHFFFAOYSA-N 4-oxo-4-phenylmethoxy-3-(phenylmethoxycarbonylamino)butanoic acid Chemical compound C=1C=CC=CC=1COC(=O)C(CC(=O)O)NC(=O)OCC1=CC=CC=C1 UYOZWZKJQRBZRH-UHFFFAOYSA-N 0.000 description 1
ACAZKHULUUVWCY-UHFFFAOYSA-N 6beta-hexanoylamino-penicillanic acid Natural products S1C(C)(C)C(C(O)=O)N2C(=O)C(NC(=O)CCCCC)C21 ACAZKHULUUVWCY-UHFFFAOYSA-N 0.000 description 1
229920001817 Agar Polymers 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241000193830 Bacillus <bacterium> Species 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
208000035473 Communicable disease Diseases 0.000 description 1
229930182846 D-asparagine Natural products 0.000 description 1
BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 1
241000588722 Escherichia Species 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
241000588748 Klebsiella Species 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
CFRMVEKWKKDNAH-VKHMYHEASA-N N(4)-methyl-L-asparagine Chemical compound CNC(=O)C[C@H](N)C(O)=O CFRMVEKWKKDNAH-VKHMYHEASA-N 0.000 description 1
QRLCJUNAKLMRGP-UHFFFAOYSA-N Penicillin F Natural products S1C(C)(C)C(C(O)=O)N2C(=O)C(NC(=O)CC=CCC)C21 QRLCJUNAKLMRGP-UHFFFAOYSA-N 0.000 description 1
QRLCJUNAKLMRGP-ZTWGYATJSA-N Penicillin F Chemical compound S1C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](NC(=O)C/C=C/CC)[C@H]21 QRLCJUNAKLMRGP-ZTWGYATJSA-N 0.000 description 1
XVASOOUVMJAZNJ-MBNYWOFBSA-N Penicillin K Chemical compound S1C(C)(C)[C@H](C(O)=O)N2C(=O)[C@@H](NC(=O)CCCCCCC)[C@H]21 XVASOOUVMJAZNJ-MBNYWOFBSA-N 0.000 description 1
241000607142 Salmonella Species 0.000 description 1
241000191940 Staphylococcus Species 0.000 description 1
241000191967 Staphylococcus aureus Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
241000194017 Streptococcus Species 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 description 1
OKMHHBICYZAXBE-UHFFFAOYSA-N acetic acid;ethanol;ethyl acetate Chemical compound CCO.CC(O)=O.CCOC(C)=O OKMHHBICYZAXBE-UHFFFAOYSA-N 0.000 description 1
239000008272 agar Substances 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
229950008560 almecillin Drugs 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000002246 antineoplastic agent Substances 0.000 description 1
229960001230 asparagine Drugs 0.000 description 1
JUHORIMYRDESRB-UHFFFAOYSA-N benzathine Chemical compound C=1C=CC=CC=1CNCCNCC1=CC=CC=C1 JUHORIMYRDESRB-UHFFFAOYSA-N 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229940127089 cytotoxic agent Drugs 0.000 description 1
235000015872 dietary supplement Nutrition 0.000 description 1
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
235000001727 glucose Nutrition 0.000 description 1
125000000262 haloalkenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
238000001802 infusion Methods 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000008176 lyophilized powder Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
QULKGELYPOJSLP-WCABBAIRSA-N penicillin O Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2[C@H](NC(=O)CSCC=C)C(=O)N21 QULKGELYPOJSLP-WCABBAIRSA-N 0.000 description 1
AZCVBVRUYHKWHU-UHFFFAOYSA-N penicillin X Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)CC1=CC=C(O)C=C1 AZCVBVRUYHKWHU-UHFFFAOYSA-N 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
239000006187 pill Substances 0.000 description 1
244000144977 poultry Species 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
239000000047 product Substances 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
229960004932 sulbenicillin Drugs 0.000 description 1
239000003826 tablet Substances 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
YUKQRDCYNOVPGJ-UHFFFAOYSA-N thioacetamide Chemical compound CC(N)=S YUKQRDCYNOVPGJ-UHFFFAOYSA-N 0.000 description 1
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
150000003556 thioamides Chemical class 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- 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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

BE170545A 1975-09-12 1976-09-10 Nouvelles penicillines et leurs procedes de preparation BE846094A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
GB37525/75A GB1533413A (en)	1975-09-12	1975-09-12	Penicillins
JP15787475A JPS5283393A (en)	1975-12-27	1975-12-27	Synthesis of novel penicillin derivatives
JP15787375A JPS5283392A (en)	1975-12-27	1975-12-27	Synthesis of novel penicillin derivatives
JP15792075A JPS5283491A (en)	1975-12-29	1975-12-29	Preparation of novel penicillin derivatives

Publications (1)

Publication Number	Publication Date
BE846094A true BE846094A (fr)	1977-03-10

Family

ID=27448893

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE170545A BE846094A (fr)	1975-09-12	1976-09-10	Nouvelles penicillines et leurs procedes de preparation

Country Status (9)

Country	Link
US (1)	US4053609A (da)
BE (1)	BE846094A (da)
CA (1)	CA1081211A (da)
DE (1)	DE2638067C2 (da)
DK (1)	DK144301C (da)
FI (1)	FI63413C (da)
FR (1)	FR2323384A1 (da)
NL (1)	NL176677C (da)
SE (1)	SE430337B (da)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1577931A (en) *	1977-02-11	1980-10-29	Beecham Group Ltd	6-methoxy -6-(2-carboxy-2-(4-hydroxyphenyl) acetamido penicillins
DE2817228A1 (de) *	1978-04-20	1979-10-31	Bayer Ag	Verfahren zur herstellung halbsynthetischer beta-lactamantibiotika
JPS5640686A (en) *	1979-09-11	1981-04-16	Tanabe Seiyaku Co Ltd	Purification of penicillin derivative
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
JPS63174927A (ja) *	1987-01-14	1988-07-19	Tanabe Seiyaku Co Ltd	抗菌性凍結乾燥製剤
EP0606506A1 (en)	1993-01-12	1994-07-20	Yeong Sul Kim	Beta-lactamase resistant antibacterial composition
IT1264765B1 (it) *	1993-03-10	1996-10-04	Rotta Research Lab	Derivati dell'acido glutammico ed acido aspartico, procedimento per la loro preparazione e loro uso come farmaci potenzianti la
CN101747342B (zh) *	2008-12-08	2013-03-06	南京海纳医药科技有限公司	一种阿扑西林的合成工艺
CN103159783B (zh) *	2013-03-06	2016-04-27	上海龙翔生物医药开发有限公司	一种阿扑西林三水酸的精制方法
CN103992337B (zh) *	2014-04-23	2016-08-17	南京优科生物医药研究有限公司	一种便捷的制备阿扑西林钠的方法

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3340252A (en) *	1964-04-07	1967-09-05	American Home Prod	Amino-acylamino-acylamino-penicillanic acids
GB1080247A (en) *	1965-07-27	1967-08-23	Beecham Group Ltd	Penicillins
JPS5751837B2 (da) *	1973-04-05	1982-11-04
IL44728A (en) *	1973-05-04	1977-08-31	Beecham Group Ltd	Alpha-aminoacyldipeptide penicillins and their preparatio
GB1503918A (en) *	1974-06-18	1978-03-15	Beecham Group Ltd	Penicillins

1976
- 1976-08-05 US US05/711,858 patent/US4053609A/en not_active Expired - Lifetime
- 1976-08-24 DE DE2638067A patent/DE2638067C2/de not_active Expired
- 1976-09-08 FI FI762576A patent/FI63413C/fi not_active IP Right Cessation
- 1976-09-08 SE SE7609909A patent/SE430337B/xx not_active IP Right Cessation
- 1976-09-10 DK DK411076A patent/DK144301C/da not_active IP Right Cessation
- 1976-09-10 CA CA260,920A patent/CA1081211A/en not_active Expired
- 1976-09-10 BE BE170545A patent/BE846094A/fr not_active IP Right Cessation
- 1976-09-10 FR FR7627393A patent/FR2323384A1/fr active Granted
- 1976-09-13 NL NLAANVRAGE7610151,A patent/NL176677C/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
FI762576A7 (da)	1977-03-13
FI63413C (fi)	1983-06-10
US4053609A (en)	1977-10-11
FI63413B (fi)	1983-02-28
NL176677C (nl)	1985-05-17
DE2638067C2 (de)	1982-11-11
FR2323384B1 (da)	1979-10-19
SE7609909L (sv)	1977-03-13
CA1081211A (en)	1980-07-08
DK411076A (da)	1977-03-13
NL176677B (nl)	1984-12-17
DK144301B (da)	1982-02-08
DK144301C (da)	1982-07-05
DE2638067A1 (de)	1977-03-24
NL7610151A (nl)	1977-03-15
AU1769776A (en)	1978-03-23
SE430337B (sv)	1983-11-07
FR2323384A1 (fr)	1977-04-08

Legal Events

Date

Code

Title

Description

1996-01-01

RE20

Patent expired

Owner name: TANABE SEIYAKU CY LTD

Effective date: 19960910

Publication	Publication Date	Title
EP0034536B1 (fr)	1984-12-27	Nouvelles oximes dérivées de l'acide 3-alkyloxy ou 3-alkylthiométhyl 7-amino thiazolylacétamido céphalosporanique, leur préparation, leur application comme médicaments et les compositions les renfermant
CA1334407C (fr)	1995-02-14	Procede de preparation de nouvelles alcoyloximes derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique
CH633292A5 (fr)	1982-11-30	Oximes derivees de l'acide 3-acetoxymethyl 7-amino thiazolyl acetamido cephalosporanique, procede de preparation et compositions pharmaceutiques.
CH622264A5 (en)	1981-03-31	Process for the preparation of new oximes, syn isomers, derived from 7-(aminothiazolylacetamido)cephalosporanic acid
EP1525193B1 (fr)	2007-12-26	Derives d'acylaminothiazole et leur utilisation comme inhibiteurs de beta-amyloide
FR2663332A1 (fr)	1991-12-20	Nouvelles cephalosporines comportant en position 3 un radical propenyle substitue par un ammonium quaternaire, leur procede de preparation, leur application comme medicaments, les compositions les renfermant et les nouveaux intermediaires obtenus.
FR2565587A1 (fr)	1985-12-13	Derive nouveau de diamide d'amino-acide a caractere acide n-acylique, un sel de celui-ci, un procede de production de celui-ci et un agent anti-ulcereux le contenant
BE846094A (fr)	1977-03-10	Nouvelles penicillines et leurs procedes de preparation
CH638221A5 (fr)	1983-09-15	Oximes derivees de l'acide 3-substitue 7-amino thiazolyl acetamido cephalosporanique, leur procede de preparation et les compositions pharmaceutiques les renfermant.
CH629815A5 (en)	1982-05-14	Oximes derived from 7-(aminothiazolylacetamido)cephalosporanic acid, process of preparation and pharmaceutical compositions
CA1094546A (fr)	1981-01-27	Procede de preparation de derives de l'acide 7-amino thiazolyl acetamido cephalosporanique
CH628900A5 (fr)	1982-03-31	Procede de preparation de thio-oximes derivees de cephalosporines et de penicillines.
CA1148937A (fr)	1983-06-28	Procede de preparation de nouvelles aco-yloximes substituees derivees de l'acide 7-(2-amino 4-thiazolyl) acetamido cephalosporanique
CA1132537A (fr)	1982-09-28	Procede de preparation de nouvelles oximes derivees de l'acide 3-thiadiazolyl thiomethyl 7-aminothiazolyl acetamido cephalosporanique
CA1094547A (fr)	1981-01-27	Procede de preparation de derives de l'acide 3- carbamoyloxymethyl 7-(amino thiazolyl acetamido) cephalosporanique
CH639388A5 (fr)	1983-11-15	Cephalosporines derivees de l'acide 7-/2-(2-amino 4-thiazolyl) 2-(carboxymethoxyimino) acetamido/ 3-substitue cephalosporanique, leurs procedes de preparation et medicaments les renfermant.
FR2505840A1 (fr)	1982-11-19	Nouveaux produits derives de l'acide 2-amino thiazolyl 2-oxyimino acetamido bicyclo-octene carboxylique, leur procede de preparation et leur application comme medicaments
CH626088A5 (en)	1981-10-30	Process for the preparation of new oximes derived from 3-carbamoyloxymethyl-7-(aminothiazolylacetamido)cephalosporanic acid
CH640858A5 (fr)	1984-01-31	Oximes derivees de l'acide 3-azidomethyl 7-amino thiazolyl acetamido cephalosporanique, leurs procedes de preparation et les medicaments les renfermant.
LU85780A1 (fr)	1985-12-11	Nouveaux esters enoliques precurseurs de medicaments et composition pharmaceutique les contenant
EP0104671B1 (fr)	1990-05-23	Nouvelles oximes dérivées de l'acide 3-alkyloxy ou 3-alkylthiométhyl-7 amino thiazolylacétamido céphalosporaniques, leur préparation, leur application comme médicaments et les compositions les renfermant
FR2576596A1 (fr)	1986-08-01	Procede de preparation de 4,4-dialkyl-2-azetidinones, et composes nouveaux ainsi prepares
CA1140113A (fr)	1983-01-25	Procede de preparation de nouvelles oximes 0-substituees par un radical comportant un ammonium quatermaire et derivees de l'acide 7-amino thiazolyl acetamido cephalosporanique
EP0280627B1 (fr)	1993-04-21	Nouveaux dérivés N-substitués de l'alpha-mercaptométhyl benzène propanamide, leur procédé de préparation, leur application à titre de médicaments et les compositions les renfermant
BE852213R (fr)	1977-09-08	Nouvelles cephalosporines et leur preparation