CH618176A5 - - Google Patents
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- Publication number
- CH618176A5 CH618176A5 CH1383775A CH1383775A CH618176A5 CH 618176 A5 CH618176 A5 CH 618176A5 CH 1383775 A CH1383775 A CH 1383775A CH 1383775 A CH1383775 A CH 1383775A CH 618176 A5 CH618176 A5 CH 618176A5
- Authority
- CH
- Switzerland
- Prior art keywords
- hydroxy
- ureido
- quinolyl
- benzylpenicillin
- oxazolo
- Prior art date
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- 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 129
- 150000002148 esters Chemical class 0.000 claims description 44
- 150000001875 compounds Chemical class 0.000 claims description 36
- 150000003839 salts Chemical class 0.000 claims description 19
- 229930182555 Penicillin Natural products 0.000 claims description 14
- 238000001727 in vivo Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 150000002960 penicillins Chemical class 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000002596 lactones Chemical class 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- DCIHMFKXUPIFLL-UHFFFAOYSA-N 3h-[1,3]oxazolo[4,5-c]pyridin-2-one Chemical compound N1=CC=C2OC(=O)NC2=C1 DCIHMFKXUPIFLL-UHFFFAOYSA-N 0.000 claims description 5
- 229940049954 penicillin Drugs 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 4
- 150000001735 carboxylic acids Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000004112 carboxyamino group Chemical group [H]OC(=O)N([H])[*] 0.000 claims 2
- 150000007514 bases Chemical class 0.000 claims 1
- -1 n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec-butoxy Chemical group 0.000 description 103
- 229940056360 penicillin g Drugs 0.000 description 82
- 235000019371 penicillin G benzathine Nutrition 0.000 description 72
- 101100328518 Caenorhabditis elegans cnt-1 gene Proteins 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 8
- 239000003814 drug Substances 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical class C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- RNHDAKUGFHSZEV-UHFFFAOYSA-N 1,4-dioxane;hydrate Chemical compound O.C1COCCO1 RNHDAKUGFHSZEV-UHFFFAOYSA-N 0.000 description 5
- 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 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 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 5
- 229960000723 ampicillin Drugs 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- RPBAFSBGYDKNRG-NJBDSQKTSA-N epicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CCC=CC1 RPBAFSBGYDKNRG-NJBDSQKTSA-N 0.000 description 5
- 229960002457 epicillin Drugs 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 4
- 229960003022 amoxicillin Drugs 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000012442 inert solvent Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 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 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- WZJYKHNJTSNBHV-UHFFFAOYSA-N benzo[h]quinoline Chemical compound C1=CN=C2C3=CC=CC=C3C=CC2=C1 WZJYKHNJTSNBHV-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 229960003342 pivampicillin Drugs 0.000 description 3
- ZEMIJUDPLILVNQ-ZXFNITATSA-N pivampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC(=O)C(C)(C)C)=CC=CC=C1 ZEMIJUDPLILVNQ-ZXFNITATSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- DQECFVGMGBQCPA-GLCLSGQWSA-N 2,2-dimethylpropanoyloxymethyl (2s,5r,6r)-6-[[(2r)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydron;chloride Chemical compound Cl.C1([C@@H](N)C(=O)N[C@H]2[C@@H]3N(C2=O)[C@H](C(S3)(C)C)C(=O)OCOC(=O)C(C)(C)C)=CC=CC=C1 DQECFVGMGBQCPA-GLCLSGQWSA-N 0.000 description 2
- OIIBRAGQGFLUFI-UHFFFAOYSA-N 3-amino-1h-pyridin-4-one Chemical class NC1=CNC=CC1=O OIIBRAGQGFLUFI-UHFFFAOYSA-N 0.000 description 2
- NIQNIQVCPKCNQS-UHFFFAOYSA-N 3-amino-1h-quinolin-4-one Chemical class C1=CC=C2C(=O)C(N)=CNC2=C1 NIQNIQVCPKCNQS-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 125000002252 acyl group Chemical group 0.000 description 2
- 125000005042 acyloxymethyl group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- HCAUQPZEWLULFJ-UHFFFAOYSA-N benzo[f]quinoline Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=N1 HCAUQPZEWLULFJ-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 150000001715 carbamic acids Chemical class 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid 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
- 238000004519 manufacturing process Methods 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 150000005041 phenanthrolines Chemical class 0.000 description 2
- 229960004632 pivampicillin hydrochloride Drugs 0.000 description 2
- JZKJGYBMTGSLJH-UHFFFAOYSA-N pyrido[2,3-b][1,5]naphthyridine Chemical compound C1=CC=NC2=CC3=CC=CN=C3N=C21 JZKJGYBMTGSLJH-UHFFFAOYSA-N 0.000 description 2
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 230000000699 topical effect Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000005045 1,10-phenanthrolines Chemical class 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 description 1
- AJUQFOWOKIHAPA-UHFFFAOYSA-N 12-oxa-14,17-diazatetracyclo[8.7.0.03,8.011,15]heptadeca-1,3,5,7,9,11(15),16-heptaen-13-one Chemical compound C1=CC=CC2=CC3=C(OC(=O)N4)C4=CN=C3C=C21 AJUQFOWOKIHAPA-UHFFFAOYSA-N 0.000 description 1
- OXQGTIUCKGYOAA-UHFFFAOYSA-N 2-Ethylbutanoic acid Chemical compound CCC(CC)C(O)=O OXQGTIUCKGYOAA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- QEAIRNDCSKPPJA-UHFFFAOYSA-N 3-amino-1h-1,8-naphthyridin-4-one Chemical class C1=CC=C2C(=O)C(N)=CNC2=N1 QEAIRNDCSKPPJA-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- AZUMLDCKNIOCRV-UHFFFAOYSA-N 3h-[1,3]oxazolo[4,5-c][1,6]naphthyridin-2-one Chemical compound C1=CN=CC2=C(OC(=O)N3)C3=CN=C21 AZUMLDCKNIOCRV-UHFFFAOYSA-N 0.000 description 1
- WBLRDORZPJGLNO-UHFFFAOYSA-N 3h-[1,3]oxazolo[4,5-c][1,7]naphthyridin-2-one Chemical compound C1=NC=CC2=C(OC(=O)N3)C3=CN=C21 WBLRDORZPJGLNO-UHFFFAOYSA-N 0.000 description 1
- BKXAZSJMKVWAKT-UHFFFAOYSA-N 3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=CC=CC2=C(OC(=O)N3)C3=CN=C21 BKXAZSJMKVWAKT-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- ILUSXXHYBDBLSU-UHFFFAOYSA-N 6-bromo-3h-[1,3]oxazolo[4,5-c][1,6]naphthyridin-2-one Chemical compound N1=C2C(Br)=CN=CC2=C2OC(=O)NC2=C1 ILUSXXHYBDBLSU-UHFFFAOYSA-N 0.000 description 1
- UPSQQTRFGVJVGB-UHFFFAOYSA-N 6-bromo-3h-[1,3]oxazolo[4,5-c][1,7]naphthyridin-2-one Chemical compound N1=C2C(Br)=NC=CC2=C2OC(=O)NC2=C1 UPSQQTRFGVJVGB-UHFFFAOYSA-N 0.000 description 1
- QCGDVUOBGPJLBW-UHFFFAOYSA-N 6-chloro-3h-[1,3]oxazolo[4,5-c][1,6]naphthyridin-2-one Chemical compound N1=C2C(Cl)=CN=CC2=C2OC(=O)NC2=C1 QCGDVUOBGPJLBW-UHFFFAOYSA-N 0.000 description 1
- QPWZXXOSSLNGEC-UHFFFAOYSA-N 6-chloro-3h-[1,3]oxazolo[4,5-c][1,7]naphthyridin-2-one Chemical compound N1=C2C(Cl)=NC=CC2=C2OC(=O)NC2=C1 QPWZXXOSSLNGEC-UHFFFAOYSA-N 0.000 description 1
- SMJQFMXZJRGQIG-UHFFFAOYSA-N 6-chloro-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound N1=C2C(Cl)=CC=CC2=C2OC(=O)NC2=C1 SMJQFMXZJRGQIG-UHFFFAOYSA-N 0.000 description 1
- JUWYJERUMCSQGD-UHFFFAOYSA-N 6-ethoxy-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound N1=C2C(OCC)=CC=CC2=C2OC(=O)NC2=C1 JUWYJERUMCSQGD-UHFFFAOYSA-N 0.000 description 1
- YUDKBGLWJZHWEA-UHFFFAOYSA-N 6-ethyl-3h-[1,3]oxazolo[4,5-c][1,5]naphthyridin-2-one Chemical compound N1=C2C(CC)=CC=NC2=C2OC(=O)NC2=C1 YUDKBGLWJZHWEA-UHFFFAOYSA-N 0.000 description 1
- ODOYQPRCFHYESL-UHFFFAOYSA-N 6-methoxy-3h-[1,3]oxazolo[4,5-c][1,5]naphthyridin-2-one Chemical compound N1=C2C(OC)=CC=NC2=C2OC(=O)NC2=C1 ODOYQPRCFHYESL-UHFFFAOYSA-N 0.000 description 1
- LSVCAWLZDHDQCK-UHFFFAOYSA-N 6-methoxy-3h-[1,3]oxazolo[4,5-c][1,6]naphthyridin-2-one Chemical compound N1=C2C(OC)=CN=CC2=C2OC(=O)NC2=C1 LSVCAWLZDHDQCK-UHFFFAOYSA-N 0.000 description 1
- VLLVIHVNKZMERU-UHFFFAOYSA-N 6-methoxy-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound N1=C2C(OC)=CC=CC2=C2OC(=O)NC2=C1 VLLVIHVNKZMERU-UHFFFAOYSA-N 0.000 description 1
- XUGOUOQYAKERRD-UHFFFAOYSA-N 6-methyl-3h-[1,3]oxazolo[4,5-c][1,5]naphthyridin-2-one Chemical compound N1=C2C(C)=CC=NC2=C2OC(=O)NC2=C1 XUGOUOQYAKERRD-UHFFFAOYSA-N 0.000 description 1
- ZICAORNRHKSBKR-UHFFFAOYSA-N 6-methyl-3h-[1,3]oxazolo[4,5-c][1,6]naphthyridin-2-one Chemical compound N1=C2C(C)=CN=CC2=C2OC(=O)NC2=C1 ZICAORNRHKSBKR-UHFFFAOYSA-N 0.000 description 1
- SFQIHDQRRHHMFZ-UHFFFAOYSA-N 6-methyl-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound N1=C2C(C)=CC=CC2=C2OC(=O)NC2=C1 SFQIHDQRRHHMFZ-UHFFFAOYSA-N 0.000 description 1
- PDTZJLSTBSROFC-UHFFFAOYSA-N 7-(2-methylpropyl)-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(CC(C)C)=CC=C2C2=C1NC(=O)O2 PDTZJLSTBSROFC-UHFFFAOYSA-N 0.000 description 1
- WVBWVDONAPBJGC-UHFFFAOYSA-N 7-bromo-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(Br)=CC=C2C2=C1NC(=O)O2 WVBWVDONAPBJGC-UHFFFAOYSA-N 0.000 description 1
- NPWKEMPLHRCAKU-UHFFFAOYSA-N 7-chloro-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(Cl)=CC=C2C2=C1NC(=O)O2 NPWKEMPLHRCAKU-UHFFFAOYSA-N 0.000 description 1
- YMDKADOQCWKBNJ-UHFFFAOYSA-N 7-chloro-8-methyl-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound N1=C2C=C(Cl)C(C)=CC2=C2OC(=O)NC2=C1 YMDKADOQCWKBNJ-UHFFFAOYSA-N 0.000 description 1
- XVNNFWSHPORJOG-UHFFFAOYSA-N 7-ethyl-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(CC)=CC=C2C2=C1NC(=O)O2 XVNNFWSHPORJOG-UHFFFAOYSA-N 0.000 description 1
- LVWXRYZERSIRLI-UHFFFAOYSA-N 7-fluoro-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(F)=CC=C2C2=C1NC(=O)O2 LVWXRYZERSIRLI-UHFFFAOYSA-N 0.000 description 1
- LIHIYEJZELEXTN-UHFFFAOYSA-N 7-methoxy-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(OC)=CC=C2C2=C1NC(=O)O2 LIHIYEJZELEXTN-UHFFFAOYSA-N 0.000 description 1
- DWBBNCCCEKQOAU-UHFFFAOYSA-N 7-methyl-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=NC2=CC(C)=CC=C2C2=C1NC(=O)O2 DWBBNCCCEKQOAU-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- FNYDCPDJHJFYOZ-UHFFFAOYSA-N 8-(diethylamino)-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(N(CC)CC)=CC=C2N=CC2=C1OC(=O)N2 FNYDCPDJHJFYOZ-UHFFFAOYSA-N 0.000 description 1
- VKIXDUGBZBFRQO-UHFFFAOYSA-N 8-(dimethylamino)-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(N(C)C)=CC=C2N=CC2=C1OC(=O)N2 VKIXDUGBZBFRQO-UHFFFAOYSA-N 0.000 description 1
- KLEBEGPZVFDTHX-UHFFFAOYSA-N 8-bromo-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(Br)=CC=C2N=CC2=C1OC(=O)N2 KLEBEGPZVFDTHX-UHFFFAOYSA-N 0.000 description 1
- RARIBJFETMYSQL-UHFFFAOYSA-N 8-chloro-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(Cl)=CC=C2N=CC2=C1OC(=O)N2 RARIBJFETMYSQL-UHFFFAOYSA-N 0.000 description 1
- OWQQSCXJBYZIAQ-UHFFFAOYSA-N 8-ethoxy-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(OCC)=CC=C2N=CC2=C1OC(=O)N2 OWQQSCXJBYZIAQ-UHFFFAOYSA-N 0.000 description 1
- QVBMCZZMIUKXID-UHFFFAOYSA-N 8-ethyl-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(CC)=CC=C2N=CC2=C1OC(=O)N2 QVBMCZZMIUKXID-UHFFFAOYSA-N 0.000 description 1
- FWSHKXICIOQWQW-UHFFFAOYSA-N 8-methoxy-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C12=CC(OC)=CC=C2N=CC2=C1OC(=O)N2 FWSHKXICIOQWQW-UHFFFAOYSA-N 0.000 description 1
- NMFZIBMDTPHIQI-UHFFFAOYSA-N 9-bromo-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=C2NC(=O)OC2=C2C(Br)=CC=CC2=N1 NMFZIBMDTPHIQI-UHFFFAOYSA-N 0.000 description 1
- YPLWGPWOKPWSRY-UHFFFAOYSA-N 9-chloro-3h-[1,3]oxazolo[4,5-c]quinolin-2-one Chemical compound C1=C2NC(=O)OC2=C2C(Cl)=CC=CC2=N1 YPLWGPWOKPWSRY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- 241001622982 Bombus soroeensis proteus Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- MNQYCEIBSRBSTE-UHFFFAOYSA-N ClC=1C(=CC=2C3=C(C=NC2C1)NC(O3)=O)Cl.CC=3C(=CC=1C2=C(C=NC1C3)NC(O2)=O)C.BrC2=CC=CC=3C1=C(C=NC23)NC(O1)=O Chemical compound ClC=1C(=CC=2C3=C(C=NC2C1)NC(O3)=O)Cl.CC=3C(=CC=1C2=C(C=NC1C3)NC(O2)=O)C.BrC2=CC=CC=3C1=C(C=NC23)NC(O1)=O MNQYCEIBSRBSTE-UHFFFAOYSA-N 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
- 241000588724 Escherichia coli Species 0.000 description 1
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- CEAZRRDELHUEMR-URQXQFDESA-N Gentamicin Chemical compound O1[C@H](C(C)NC)CC[C@@H](N)[C@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](NC)[C@@](C)(O)CO2)O)[C@H](N)C[C@@H]1N CEAZRRDELHUEMR-URQXQFDESA-N 0.000 description 1
- 229930182566 Gentamicin Natural products 0.000 description 1
- 241000588747 Klebsiella pneumoniae 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
- 241000699670 Mus sp. Species 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- 229930195708 Penicillin V Natural products 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588770 Proteus mirabilis Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
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- 241000700159 Rattus Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical group ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 240000005616 Vigna mungo var. mungo Species 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229960004821 amikacin Drugs 0.000 description 1
- LKCWBDHBTVXHDL-RMDFUYIESA-N amikacin Chemical compound O([C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O1)O)NC(=O)[C@@H](O)CCN)[C@H]1O[C@H](CN)[C@@H](O)[C@H](O)[C@H]1O LKCWBDHBTVXHDL-RMDFUYIESA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
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- 239000000730 antalgic agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
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- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
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- 239000007864 aqueous solution Substances 0.000 description 1
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- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- RFQDDXWZZVRLKO-UHFFFAOYSA-N benzo[g]quinoline Chemical compound N1=CC=CC2=CC3=CC=CC=C3C=C21 RFQDDXWZZVRLKO-UHFFFAOYSA-N 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 150000003938 benzyl alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 1
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 1
- 229960003669 carbenicillin Drugs 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000000973 chemotherapeutic effect Effects 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- GGRHYQCXXYLUTL-UHFFFAOYSA-N chloromethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCCl GGRHYQCXXYLUTL-UHFFFAOYSA-N 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960003326 cloxacillin Drugs 0.000 description 1
- 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 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007943 implant Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229940056367 penicillin v Drugs 0.000 description 1
- 235000019271 petrolatum Nutrition 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 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 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 229940007042 proteus vulgaris Drugs 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 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
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension 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
- 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
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229960000707 tobramycin Drugs 0.000 description 1
- NLVFBUXFDBBNBW-PBSUHMDJSA-N tobramycin Chemical compound N[C@@H]1C[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N NLVFBUXFDBBNBW-PBSUHMDJSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742450668 DE2450668A1 (de) | 1974-10-25 | 1974-10-25 | Ureidobenzylpenicilline und verfahren zu ihrer herstellung |
| DE19752535655 DE2535655A1 (de) | 1975-08-09 | 1975-08-09 | Penicilline und verfahren zu ihrer herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH618176A5 true CH618176A5 (en, 2012) | 1980-07-15 |
Family
ID=25767869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1383775A CH618176A5 (en, 2012) | 1974-10-25 | 1975-10-24 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4031230A (en, 2012) |
| JP (1) | JPS5176287A (en, 2012) |
| AT (1) | AT346483B (en, 2012) |
| CA (1) | CA1064911A (en, 2012) |
| CH (1) | CH618176A5 (en, 2012) |
| CS (1) | CS188973B2 (en, 2012) |
| DD (1) | DD122544A5 (en, 2012) |
| DK (1) | DK479475A (en, 2012) |
| ES (1) | ES442057A1 (en, 2012) |
| FR (1) | FR2288521A1 (en, 2012) |
| GB (1) | GB1501958A (en, 2012) |
| GR (1) | GR58290B (en, 2012) |
| HU (1) | HU170859B (en, 2012) |
| IE (1) | IE42057B1 (en, 2012) |
| IL (1) | IL48320A (en, 2012) |
| LU (1) | LU73640A1 (en, 2012) |
| NL (1) | NL7512496A (en, 2012) |
| SE (1) | SE7511931L (en, 2012) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT67170B (de) * | 1976-11-06 | 1979-03-21 | Merck Patent Gmbh | Lactame verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel |
| GB2060630B (en) * | 1977-08-12 | 1982-09-22 | Taisho Pharmaceutical Co Ltd | Pyrazinoquinoline derivatives |
| ES477520A1 (es) * | 1978-02-25 | 1979-06-01 | Thomae Gmbh Dr K | Procedimiento para la preparacion de nuevas penicilinas. |
| DE2910190A1 (de) * | 1979-03-15 | 1980-10-02 | Thomae Gmbh Dr K | Neue penicilline, ihre salze, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4315014A (en) * | 1980-09-24 | 1982-02-09 | Warner-Lambert Company | Antibacterial amide compounds and pharmaceutical composition containing the same |
| US4315858A (en) * | 1980-09-24 | 1982-02-16 | Warner-Lambert Company | Antibacterial amide compounds |
| US6110929A (en) | 1998-07-28 | 2000-08-29 | 3M Innovative Properties Company | Oxazolo, thiazolo and selenazolo [4,5-c]-quinolin-4-amines and analogs thereof |
| WO2006024741A2 (fr) * | 2004-07-30 | 2006-03-09 | Palumed S.A. | Molecules hybrides qa ou q est une aminoquinoleine et a est un residu antibiotique, leur synthese et leurs utilisations en tant qu'agent antibacterien |
| CN118420620A (zh) | 2018-11-28 | 2024-08-02 | 武田药品工业株式会社 | 杂环化合物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3720664A (en) * | 1969-11-17 | 1973-03-13 | Squibb & Sons Inc | Alpha-ureidocyclohexadienylalkylene-penicillins |
| US3951955A (en) * | 1970-12-29 | 1976-04-20 | Sumitomo Chemical Company, Limited | Penicillins substituted with heterocyclic groups |
| BE794886A (fr) * | 1972-02-22 | 1973-08-02 | Pfizer | Acides 6-(alpha-(omega-guanidinoalcanoylamino)acylamino)-penicillaniques |
| JPS5417754B2 (en, 2012) * | 1972-12-15 | 1979-07-02 | ||
| JPS5751837B2 (en, 2012) * | 1973-04-05 | 1982-11-04 | ||
| US3935189A (en) * | 1973-05-04 | 1976-01-27 | Beecham Group Limited | Penicillins |
| US3939150A (en) * | 1973-10-19 | 1976-02-17 | Yamanouchi Pharmaceutical Co., Ltd. | Penicillin derivatives |
-
1975
- 1975-10-16 FR FR7531677A patent/FR2288521A1/fr active Granted
- 1975-10-20 IL IL48320A patent/IL48320A/xx unknown
- 1975-10-21 CS CS757080A patent/CS188973B2/cs unknown
- 1975-10-22 US US05/624,763 patent/US4031230A/en not_active Expired - Lifetime
- 1975-10-22 GB GB43407/75A patent/GB1501958A/en not_active Expired
- 1975-10-23 DD DD189018A patent/DD122544A5/xx unknown
- 1975-10-23 CA CA238,194A patent/CA1064911A/en not_active Expired
- 1975-10-24 SE SE7511931A patent/SE7511931L/xx unknown
- 1975-10-24 AT AT813475A patent/AT346483B/de active
- 1975-10-24 IE IE2320/75A patent/IE42057B1/en unknown
- 1975-10-24 CH CH1383775A patent/CH618176A5/de not_active IP Right Cessation
- 1975-10-24 NL NL7512496A patent/NL7512496A/xx not_active Application Discontinuation
- 1975-10-24 ES ES442057A patent/ES442057A1/es not_active Expired
- 1975-10-24 LU LU73640A patent/LU73640A1/xx unknown
- 1975-10-24 HU HUME001912 patent/HU170859B/hu unknown
- 1975-10-24 DK DK479475A patent/DK479475A/da unknown
- 1975-10-24 GR GR49201A patent/GR58290B/el unknown
- 1975-10-25 JP JP50128805A patent/JPS5176287A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| LU73640A1 (en, 2012) | 1977-05-31 |
| DK479475A (da) | 1976-04-26 |
| US4031230A (en) | 1977-06-21 |
| SE7511931L (sv) | 1976-04-26 |
| AT346483B (de) | 1978-11-10 |
| ES442057A1 (es) | 1977-07-01 |
| NL7512496A (nl) | 1976-04-27 |
| IL48320A (en) | 1978-09-29 |
| HU170859B (hu) | 1977-09-28 |
| IE42057L (en) | 1976-04-25 |
| IE42057B1 (en) | 1980-05-21 |
| DD122544A5 (en, 2012) | 1976-10-12 |
| AU8590175A (en) | 1977-04-28 |
| FR2288521B1 (en, 2012) | 1980-05-30 |
| GR58290B (en) | 1977-09-20 |
| FR2288521A1 (fr) | 1976-05-21 |
| JPS5176287A (en, 2012) | 1976-07-01 |
| IL48320A0 (en) | 1975-12-31 |
| CA1064911A (en) | 1979-10-23 |
| GB1501958A (en) | 1978-02-22 |
| CS188973B2 (en) | 1979-03-30 |
| ATA813475A (de) | 1978-03-15 |
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