DE3902079A1 - I.m. injektionsformen von gyrase-inhibitoren - Google Patents
I.m. injektionsformen von gyrase-inhibitorenInfo
- Publication number
- DE3902079A1 DE3902079A1 DE3902079A DE3902079A DE3902079A1 DE 3902079 A1 DE3902079 A1 DE 3902079A1 DE 3902079 A DE3902079 A DE 3902079A DE 3902079 A DE3902079 A DE 3902079A DE 3902079 A1 DE3902079 A1 DE 3902079A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- methyl
- hydrogen
- forms according
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 239000002271 gyrase inhibitor Substances 0.000 title claims description 15
- 238000002347 injection Methods 0.000 title claims description 12
- 239000007924 injection Substances 0.000 title claims description 12
- 239000000725 suspension Substances 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- 239000002253 acid Substances 0.000 claims description 21
- 238000010255 intramuscular injection Methods 0.000 claims description 21
- 238000009472 formulation Methods 0.000 claims description 19
- -1 methoxy, amino, methylamino, dimethylamino, ethylamino, phenyl Chemical group 0.000 claims description 18
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000007927 intramuscular injection Substances 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 12
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 11
- 239000000787 lecithin Substances 0.000 claims description 11
- 235000010445 lecithin Nutrition 0.000 claims description 11
- 229940067606 lecithin Drugs 0.000 claims description 11
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 239000013543 active substance Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000000460 chlorine Chemical group 0.000 claims description 6
- 229910052801 chlorine Chemical group 0.000 claims description 6
- 238000000265 homogenisation Methods 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 230000002490 cerebral effect Effects 0.000 claims description 5
- 239000004310 lactic acid Substances 0.000 claims description 5
- 235000014655 lactic acid Nutrition 0.000 claims description 5
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 4
- 240000002791 Brassica napus Species 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 244000068988 Glycine max Species 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 claims description 3
- 239000003963 antioxidant agent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000651 prodrug Substances 0.000 claims description 3
- 229940002612 prodrug Drugs 0.000 claims description 3
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- YCWRFIYBUQBHJI-UHFFFAOYSA-N 2-(4-aminophenyl)acetonitrile Chemical group NC1=CC=C(CC#N)C=C1 YCWRFIYBUQBHJI-UHFFFAOYSA-N 0.000 claims description 2
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 claims description 2
- 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
- 125000001539 acetonyl group Chemical group [H]C([H])([H])C(=O)C([H])([H])* 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 239000008365 aqueous carrier Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000006534 ethyl amino methyl group Chemical group [H]N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 229950002475 mesilate Drugs 0.000 claims description 2
- 125000006533 methyl amino methyl group Chemical group [H]N(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 230000001225 therapeutic effect Effects 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical class CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 238000011282 treatment Methods 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 238000005273 aeration Methods 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 description 57
- 239000000243 solution Substances 0.000 description 32
- 229960003405 ciprofloxacin Drugs 0.000 description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 235000002639 sodium chloride Nutrition 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000007900 aqueous suspension Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 8
- 244000052769 pathogen Species 0.000 description 8
- 238000001556 precipitation Methods 0.000 description 7
- 230000001954 sterilising effect Effects 0.000 description 7
- 238000004659 sterilization and disinfection Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000008215 water for injection Substances 0.000 description 7
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 6
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical group C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 4
- 206010039438 Salmonella Infections Diseases 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 229960000448 lactic acid Drugs 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000000902 placebo Substances 0.000 description 4
- 229940068196 placebo Drugs 0.000 description 4
- 206010039447 salmonellosis Diseases 0.000 description 4
- 230000009885 systemic effect Effects 0.000 description 4
- 201000004813 Bronchopneumonia Diseases 0.000 description 3
- 206010012735 Diarrhoea Diseases 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000012670 alkaline solution Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 235000010323 ascorbic acid Nutrition 0.000 description 3
- 239000011668 ascorbic acid Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 208000004396 mastitis Diseases 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 206010034674 peritonitis Diseases 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
- PWKSKIMOESPYIA-UHFFFAOYSA-N 2-acetamido-3-sulfanylpropanoic acid Chemical compound CC(=O)NC(CS)C(O)=O PWKSKIMOESPYIA-UHFFFAOYSA-N 0.000 description 2
- ODJQKYXPKWQWNK-UHFFFAOYSA-N 3,3'-Thiobispropanoic acid Chemical compound OC(=O)CCSCCC(O)=O ODJQKYXPKWQWNK-UHFFFAOYSA-N 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 241000588921 Enterobacteriaceae Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- IAJILQKETJEXLJ-UHFFFAOYSA-N Galacturonsaeure Natural products O=CC(O)C(O)C(O)C(O)C(O)=O IAJILQKETJEXLJ-UHFFFAOYSA-N 0.000 description 2
- 206010048461 Genital infection Diseases 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- 208000005141 Otitis Diseases 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 206010034107 Pasteurella infections Diseases 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 108091000080 Phosphotransferase Proteins 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 206010040047 Sepsis Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000003490 Thiodipropionic acid Substances 0.000 description 2
- 241000607734 Yersinia <bacteria> Species 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 235000006708 antioxidants Nutrition 0.000 description 2
- 229960005070 ascorbic acid Drugs 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 235000019445 benzyl alcohol Nutrition 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229940109239 creatinine Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 208000001848 dysentery Diseases 0.000 description 2
- 208000019258 ear infection Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 238000004388 gamma ray sterilization Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 230000007794 irritation Effects 0.000 description 2
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
- 229940001447 lactate Drugs 0.000 description 2
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 2
- 201000005115 pasteurellosis Diseases 0.000 description 2
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 102000020233 phosphotransferase Human genes 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000000473 propyl gallate Substances 0.000 description 2
- 235000010388 propyl gallate Nutrition 0.000 description 2
- 229940075579 propyl gallate Drugs 0.000 description 2
- 201000007094 prostatitis Diseases 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
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- 235000019303 thiodipropionic acid Nutrition 0.000 description 2
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JURKHZKZOIJIOV-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-2-(3-methyl-4-propylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)N(CCC)CCN1C1=C(C(O)=O)C(=O)C2=CC(F)=CC(F)=C2N1C1CC1 JURKHZKZOIJIOV-UHFFFAOYSA-N 0.000 description 1
- AKBYOTPRLLAOEW-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-(3,4,5-trimethylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C1C(C)N(C)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F AKBYOTPRLLAOEW-UHFFFAOYSA-N 0.000 description 1
- VWGHZCWJQFMMCB-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-(3-propan-2-ylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C1CNC(C(C)C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F VWGHZCWJQFMMCB-UHFFFAOYSA-N 0.000 description 1
- HRGVXCUTKCOZDN-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-(3-propylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C1CNC(CCC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F HRGVXCUTKCOZDN-UHFFFAOYSA-N 0.000 description 1
- CZXWNPNFWRABAP-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 CZXWNPNFWRABAP-UHFFFAOYSA-N 0.000 description 1
- ZHKOPMSOBOQYRH-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-(3-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F ZHKOPMSOBOQYRH-UHFFFAOYSA-N 0.000 description 1
- DKTASLMCKRHWAK-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F DKTASLMCKRHWAK-UHFFFAOYSA-N 0.000 description 1
- LGRLQVSGTHDGKG-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[3-(2-methylpropyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(CC(C)C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F LGRLQVSGTHDGKG-UHFFFAOYSA-N 0.000 description 1
- RSMONWZDFDOLIZ-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-[4-(2-hydroxyethyl)-3-methylpiperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CCO)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F RSMONWZDFDOLIZ-UHFFFAOYSA-N 0.000 description 1
- FHJKCFNPRSJSNU-UHFFFAOYSA-N 1-cyclopropyl-6,8-difluoro-7-morpholin-4-yl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCOCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 FHJKCFNPRSJSNU-UHFFFAOYSA-N 0.000 description 1
- YYDIPIBZANVEEQ-UHFFFAOYSA-N 1-cyclopropyl-7-(3,4-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F YYDIPIBZANVEEQ-UHFFFAOYSA-N 0.000 description 1
- CMGSYIRPKZAEFD-UHFFFAOYSA-N 1-cyclopropyl-7-(3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)NC(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F CMGSYIRPKZAEFD-UHFFFAOYSA-N 0.000 description 1
- RJORMICSPQRMQV-UHFFFAOYSA-N 1-cyclopropyl-7-(3-ethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CNC(CC)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F RJORMICSPQRMQV-UHFFFAOYSA-N 0.000 description 1
- POFVVCVFKIINMO-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethyl-3,5-dimethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)N(CC)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F POFVVCVFKIINMO-UHFFFAOYSA-N 0.000 description 1
- NIPGQMJIUPNCIW-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethyl-3-methylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)N(CC)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F NIPGQMJIUPNCIW-UHFFFAOYSA-N 0.000 description 1
- YAHXZADEQGUPRE-UHFFFAOYSA-N 1-cyclopropyl-7-(4-ethylpiperazin-1-yl)-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(CC)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F YAHXZADEQGUPRE-UHFFFAOYSA-N 0.000 description 1
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 description 1
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 description 1
- ZFRUGZMCGCYBRC-UHFFFAOYSA-N 1h-1,8-naphthyridin-2-one Chemical compound C1=CC=NC2=NC(O)=CC=C21 ZFRUGZMCGCYBRC-UHFFFAOYSA-N 0.000 description 1
- UOQHWNPVNXSDDO-UHFFFAOYSA-N 3-bromoimidazo[1,2-a]pyridine-6-carbonitrile Chemical compound C1=CC(C#N)=CN2C(Br)=CN=C21 UOQHWNPVNXSDDO-UHFFFAOYSA-N 0.000 description 1
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- YDCABRFIMRVMGF-UHFFFAOYSA-N 6,8-dichloro-1-cyclopropyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CCNCC3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 YDCABRFIMRVMGF-UHFFFAOYSA-N 0.000 description 1
- RQBLLVJGAAWYEN-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-4-oxo-7-(4-propan-2-ylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C1CN(C(C)C)CCN1C1=C(Cl)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F RQBLLVJGAAWYEN-UHFFFAOYSA-N 0.000 description 1
- APKYXKSCYWUIOU-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-4-oxo-7-[3-(4-phenylphenyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(NCC3)C=3C=CC(=CC=3)C=3C=CC=CC=3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 APKYXKSCYWUIOU-UHFFFAOYSA-N 0.000 description 1
- IKPAREALPRBJDX-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-4-oxo-7-thiomorpholin-4-ylquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCSCC3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 IKPAREALPRBJDX-UHFFFAOYSA-N 0.000 description 1
- YUDODYWDUONFAV-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-7-[3-(4-fluorophenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(NCC3)C=3C=CC(F)=CC=3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 YUDODYWDUONFAV-UHFFFAOYSA-N 0.000 description 1
- URLFJCGEAZUVFK-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-7-[3-(4-methoxyphenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1NCCN(C=2C(=C3C(C(C(C(O)=O)=CN3C3CC3)=O)=CC=2Cl)F)C1 URLFJCGEAZUVFK-UHFFFAOYSA-N 0.000 description 1
- QPINHVFSIVYZQT-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-7-[3-(4-methylphenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1NCCN(C=2C(=C3C(C(C(C(O)=O)=CN3C3CC3)=O)=CC=2Cl)F)C1 QPINHVFSIVYZQT-UHFFFAOYSA-N 0.000 description 1
- PIGBECGNFNOJAK-UHFFFAOYSA-N 6-chloro-1-cyclopropyl-8-fluoro-7-morpholin-4-yl-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CCOCC3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 PIGBECGNFNOJAK-UHFFFAOYSA-N 0.000 description 1
- RLYNUEUBYAUDQN-UHFFFAOYSA-N 6-chloro-7-[3-(4-chlorophenyl)piperazin-1-yl]-1-cyclopropyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(NCC3)C=3C=CC(Cl)=CC=3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 RLYNUEUBYAUDQN-UHFFFAOYSA-N 0.000 description 1
- UHBXZNXCIZHGFF-UHFFFAOYSA-N 7-(3-aminopyrrolidin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F UHBXZNXCIZHGFF-UHFFFAOYSA-N 0.000 description 1
- JHDNUMKGLSVIEQ-UHFFFAOYSA-N 7-(4-acetylpiperazin-1-yl)-6,8-dichloro-1-cyclopropyl-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1C1=C(Cl)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1Cl JHDNUMKGLSVIEQ-UHFFFAOYSA-N 0.000 description 1
- MHRZNSDGITWYDT-UHFFFAOYSA-N 7-(4-acetylpiperazin-1-yl)-6-chloro-1-cyclopropyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1CN(C(=O)C)CCN1C1=C(Cl)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F MHRZNSDGITWYDT-UHFFFAOYSA-N 0.000 description 1
- VGNRZYRLKPOENR-UHFFFAOYSA-N 7-(4-butyl-3-methylpiperazin-1-yl)-1-cyclopropyl-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(C)N(CCCC)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F VGNRZYRLKPOENR-UHFFFAOYSA-N 0.000 description 1
- OBLARDPCWHWGBV-UHFFFAOYSA-N 7-[3-(4-bromophenyl)piperazin-1-yl]-6-chloro-1-cyclopropyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(F)C(N3CC(NCC3)C=3C=CC(Br)=CC=3)=C(Cl)C=C2C(=O)C(C(=O)O)=CN1C1CC1 OBLARDPCWHWGBV-UHFFFAOYSA-N 0.000 description 1
- SUVHVMBUDRXNKI-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-(3-phenylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CC(NCC3)C=3C=CC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 SUVHVMBUDRXNKI-UHFFFAOYSA-N 0.000 description 1
- XITVYBAKLJHNIS-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-(3-thiophen-2-ylpiperazin-1-yl)quinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CC(NCC3)C=3SC=CC=3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 XITVYBAKLJHNIS-UHFFFAOYSA-N 0.000 description 1
- CGVRTUIRWXLSRZ-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-[3-(3,4,5-trimethoxyphenyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(C2NCCN(C2)C=2C(=C3C(C(C(C(O)=O)=CN3C3CC3)=O)=CC=2F)Cl)=C1 CGVRTUIRWXLSRZ-UHFFFAOYSA-N 0.000 description 1
- VVBQZKOGRSGVPT-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-[3-(4-piperidin-1-ylphenyl)piperazin-1-yl]quinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CC(NCC3)C=3C=CC(=CC=3)N3CCCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 VVBQZKOGRSGVPT-UHFFFAOYSA-N 0.000 description 1
- MVXLDPRRAAVKTB-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-4-oxo-7-piperidin-1-ylquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3CCCCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MVXLDPRRAAVKTB-UHFFFAOYSA-N 0.000 description 1
- CGOQDZKBNDSFNO-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-6-fluoro-7-[2-(4-nitrophenyl)piperazin-1-yl]-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(Cl)C(N3C(CNCC3)C=3C=CC(=CC=3)[N+]([O-])=O)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 CGOQDZKBNDSFNO-UHFFFAOYSA-N 0.000 description 1
- FZMLPRJNWFWIIK-UHFFFAOYSA-N 8-chloro-1-cyclopropyl-7-(4-ethyl-3-oxopiperazin-1-yl)-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1C(=O)N(CC)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1Cl FZMLPRJNWFWIIK-UHFFFAOYSA-N 0.000 description 1
- GSDSWSVVBLHKDQ-UHFFFAOYSA-N 9-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid Chemical compound FC1=CC(C(C(C(O)=O)=C2)=O)=C3N2C(C)COC3=C1N1CCN(C)CC1 GSDSWSVVBLHKDQ-UHFFFAOYSA-N 0.000 description 1
- 206010060921 Abdominal abscess Diseases 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000589291 Acinetobacter Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 235000019489 Almond oil Nutrition 0.000 description 1
- RUXPNBWPIRDVTH-UHFFFAOYSA-N Amifloxacin Chemical compound C1=C2N(NC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 RUXPNBWPIRDVTH-UHFFFAOYSA-N 0.000 description 1
- 206010003011 Appendicitis Diseases 0.000 description 1
- 235000003911 Arachis Nutrition 0.000 description 1
- 244000105624 Arachis hypogaea Species 0.000 description 1
- 206010053555 Arthritis bacterial Diseases 0.000 description 1
- 239000004261 Ascorbyl stearate Substances 0.000 description 1
- LITUBCVUXPBCGA-WMZHIEFXSA-N Ascorbyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O LITUBCVUXPBCGA-WMZHIEFXSA-N 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- SPFYMRJSYKOXGV-UHFFFAOYSA-N Baytril Chemical compound C1CN(CC)CCN1C(C(=C1)F)=CC2=C1C(=O)C(C(O)=O)=CN2C1CC1 SPFYMRJSYKOXGV-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- 206010005940 Bone and joint infections Diseases 0.000 description 1
- 241000589968 Borrelia Species 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 235000014698 Brassica juncea var multisecta Nutrition 0.000 description 1
- 235000006008 Brassica napus var napus Nutrition 0.000 description 1
- 235000006618 Brassica rapa subsp oleifera Nutrition 0.000 description 1
- 244000188595 Brassica sinapistrum Species 0.000 description 1
- 241001261624 Brevundimonas bacteroides Species 0.000 description 1
- 241000589562 Brucella Species 0.000 description 1
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
- CWWJZKBUTYZCAE-UHFFFAOYSA-N C1C(C)N(CC)CC(C)N1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F Chemical compound C1C(C)N(CC)CC(C)N1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F CWWJZKBUTYZCAE-UHFFFAOYSA-N 0.000 description 1
- IFICZQMDFQGXRR-UHFFFAOYSA-N C1CN(CCCO)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F Chemical compound C1CN(CCCO)C(C)CN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1F IFICZQMDFQGXRR-UHFFFAOYSA-N 0.000 description 1
- 241000589876 Campylobacter Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 206010007882 Cellulitis Diseases 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- GHXZTYHSJHQHIJ-UHFFFAOYSA-N Chlorhexidine Chemical class C=1C=C(Cl)C=CC=1NC(N)=NC(N)=NCCCCCCN=C(N)N=C(N)NC1=CC=C(Cl)C=C1 GHXZTYHSJHQHIJ-UHFFFAOYSA-N 0.000 description 1
- 208000014085 Chronic respiratory disease Diseases 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 241000588923 Citrobacter Species 0.000 description 1
- 241000193403 Clostridium Species 0.000 description 1
- 208000003322 Coinfection Diseases 0.000 description 1
- 241000272201 Columbiformes Species 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- CKLJMWTZIZZHCS-UHFFFAOYSA-N D-OH-Asp Natural products OC(=O)C(N)CC(O)=O CKLJMWTZIZZHCS-UHFFFAOYSA-N 0.000 description 1
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 235000019227 E-number Nutrition 0.000 description 1
- 239000004243 E-number Substances 0.000 description 1
- 206010014561 Emphysema Diseases 0.000 description 1
- 208000004145 Endometritis Diseases 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000186811 Erysipelothrix Species 0.000 description 1
- 208000001860 Eye Infections Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 206010017964 Gastrointestinal infection Diseases 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
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 241000588731 Hafnia Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- 208000004575 Infectious Arthritis Diseases 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- CKLJMWTZIZZHCS-UWTATZPHSA-N L-Aspartic acid Natural products OC(=O)[C@H](N)CC(O)=O CKLJMWTZIZZHCS-UWTATZPHSA-N 0.000 description 1
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- 229930064664 L-arginine Natural products 0.000 description 1
- 235000014852 L-arginine Nutrition 0.000 description 1
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 1
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 239000004395 L-leucine Substances 0.000 description 1
- 235000019454 L-leucine Nutrition 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 206010024652 Liver abscess Diseases 0.000 description 1
- 208000016604 Lyme disease Diseases 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 208000010315 Mastoiditis Diseases 0.000 description 1
- 201000009906 Meningitis Diseases 0.000 description 1
- 241000219470 Mirabilis Species 0.000 description 1
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241000204048 Mycoplasma hominis Species 0.000 description 1
- 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- 241000588652 Neisseria gonorrhoeae Species 0.000 description 1
- 206010021888 Nervous system infections Diseases 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000187654 Nocardia Species 0.000 description 1
- 206010031252 Osteomyelitis Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229930182555 Penicillin Natural products 0.000 description 1
- 241000206591 Peptococcus Species 0.000 description 1
- 241000191992 Peptostreptococcus Species 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 229920002685 Polyoxyl 35CastorOil Polymers 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 241000588768 Providencia Species 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 206010037151 Psittacosis Diseases 0.000 description 1
- 206010037596 Pyelonephritis Diseases 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 208000007893 Salpingitis Diseases 0.000 description 1
- 241000607720 Serratia Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 208000031650 Surgical Wound Infection Diseases 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 241000589886 Treponema Species 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- 206010046793 Uterine inflammation Diseases 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 206010000269 abscess Diseases 0.000 description 1
- 229940022663 acetate Drugs 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 229960000250 adipic acid Drugs 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 230000037006 agalactosis Effects 0.000 description 1
- IAJILQKETJEXLJ-RSJOWCBRSA-N aldehydo-D-galacturonic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-RSJOWCBRSA-N 0.000 description 1
- IAJILQKETJEXLJ-QTBDOELSSA-N aldehydo-D-glucuronic acid Chemical compound O=C[C@H](O)[C@@H](O)[C@H](O)[C@H](O)C(O)=O IAJILQKETJEXLJ-QTBDOELSSA-N 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- 239000008168 almond oil Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- CEGOLXSVJUTHNZ-UHFFFAOYSA-K aluminium tristearate Chemical compound [Al+3].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CEGOLXSVJUTHNZ-UHFFFAOYSA-K 0.000 description 1
- 229940063655 aluminum stearate Drugs 0.000 description 1
- 230000001668 ameliorated effect Effects 0.000 description 1
- 229950009484 amifloxacin Drugs 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940126575 aminoglycoside Drugs 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 229940027987 antiseptic and disinfectant phenol and derivative Drugs 0.000 description 1
- 239000013011 aqueous formulation Substances 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 235000019276 ascorbyl stearate Nutrition 0.000 description 1
- 229960005261 aspartic acid Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 229960000686 benzalkonium chloride Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-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
- 229960003237 betaine Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000037058 blood plasma level Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- CZBZUDVBLSSABA-UHFFFAOYSA-N butylated hydroxyanisole Chemical compound COC1=CC=C(O)C(C(C)(C)C)=C1.COC1=CC=C(O)C=C1C(C)(C)C CZBZUDVBLSSABA-UHFFFAOYSA-N 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229960004926 chlorobutanol Drugs 0.000 description 1
- 208000003167 cholangitis Diseases 0.000 description 1
- 201000001352 cholecystitis Diseases 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- QGPKADBNRMWEQR-UHFFFAOYSA-N clinafloxacin Chemical compound C1C(N)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(C3CC3)C2=C1Cl QGPKADBNRMWEQR-UHFFFAOYSA-N 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000012611 container material Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- 201000003146 cystitis Diseases 0.000 description 1
- 235000010389 delta-tocopherol Nutrition 0.000 description 1
- 206010062952 diffuse panbronchiolitis Diseases 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000008344 egg yolk phospholipid Substances 0.000 description 1
- 206010014665 endocarditis Diseases 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 229960002549 enoxacin Drugs 0.000 description 1
- IDYZIJYBMGIQMJ-UHFFFAOYSA-N enoxacin Chemical compound N1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 IDYZIJYBMGIQMJ-UHFFFAOYSA-N 0.000 description 1
- 229960000740 enrofloxacin Drugs 0.000 description 1
- 208000029182 enterotoxemia Diseases 0.000 description 1
- 201000010063 epididymitis Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 1
- 208000011323 eye infectious disease Diseases 0.000 description 1
- 229960003306 fleroxacin Drugs 0.000 description 1
- XBJBPGROQZJDOJ-UHFFFAOYSA-N fleroxacin Chemical compound C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN(CCF)C2=C1F XBJBPGROQZJDOJ-UHFFFAOYSA-N 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229940097043 glucuronic acid Drugs 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 229960002743 glutamine Drugs 0.000 description 1
- RZRNAYUHWVFMIP-HXUWFJFHSA-N glycerol monolinoleate Natural products CCCCCCCCC=CCCCCCCCC(=O)OC[C@H](O)CO RZRNAYUHWVFMIP-HXUWFJFHSA-N 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 229960004275 glycolic acid Drugs 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- CJNBYAVZURUTKZ-UHFFFAOYSA-N hafnium(IV) oxide Inorganic materials O=[Hf]=O CJNBYAVZURUTKZ-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 239000003978 infusion fluid Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 229940045996 isethionic acid Drugs 0.000 description 1
- 229940074928 isopropyl myristate Drugs 0.000 description 1
- XUGNVMKQXJXZCD-UHFFFAOYSA-N isopropyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC(C)C XUGNVMKQXJXZCD-UHFFFAOYSA-N 0.000 description 1
- 229940075495 isopropyl palmitate Drugs 0.000 description 1
- 150000003893 lactate salts Chemical class 0.000 description 1
- 229940099563 lactobionic acid Drugs 0.000 description 1
- 229960003136 leucine Drugs 0.000 description 1
- YECIFGHRMFEPJK-UHFFFAOYSA-N lidocaine hydrochloride monohydrate Chemical compound O.[Cl-].CC[NH+](CC)CC(=O)NC1=C(C)C=CC=C1C YECIFGHRMFEPJK-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 229960005015 local anesthetics Drugs 0.000 description 1
- 229960002422 lomefloxacin Drugs 0.000 description 1
- ZEKZLJVOYLTDKK-UHFFFAOYSA-N lomefloxacin Chemical compound FC1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNC(C)C1 ZEKZLJVOYLTDKK-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 229940099690 malic acid Drugs 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 229940057917 medium chain triglycerides Drugs 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229940074096 monoolein Drugs 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002823 nitrates Chemical class 0.000 description 1
- 229940074355 nitric acid Drugs 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 229960001180 norfloxacin Drugs 0.000 description 1
- OGJPXUAPXNRGGI-UHFFFAOYSA-N norfloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCNCC1 OGJPXUAPXNRGGI-UHFFFAOYSA-N 0.000 description 1
- 229960001699 ofloxacin Drugs 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- BARWIPMJPCRCTP-UHFFFAOYSA-N oleic acid oleyl ester Natural products CCCCCCCCC=CCCCCCCCCOC(=O)CCCCCCCC=CCCCCCCCC BARWIPMJPCRCTP-UHFFFAOYSA-N 0.000 description 1
- BARWIPMJPCRCTP-CLFAGFIQSA-N oleyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCCOC(=O)CCCCCCC\C=C/CCCCCCCC BARWIPMJPCRCTP-CLFAGFIQSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 201000000901 ornithosis Diseases 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 229940116315 oxalic acid Drugs 0.000 description 1
- QUANRIQJNFHVEU-UHFFFAOYSA-N oxirane;propane-1,2,3-triol Chemical compound C1CO1.OCC(O)CO QUANRIQJNFHVEU-UHFFFAOYSA-N 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229960004236 pefloxacin Drugs 0.000 description 1
- FHFYDNQZQSQIAI-UHFFFAOYSA-N pefloxacin Chemical compound C1=C2N(CC)C=C(C(O)=O)C(=O)C2=CC(F)=C1N1CCN(C)CC1 FHFYDNQZQSQIAI-UHFFFAOYSA-N 0.000 description 1
- 150000002960 penicillins Chemical class 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229960004838 phosphoric acid Drugs 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 239000008389 polyethoxylated castor oil Substances 0.000 description 1
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000010491 poppyseed oil Substances 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 229960004919 procaine Drugs 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
- 238000011321 prophylaxis Methods 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000000384 rearing effect Effects 0.000 description 1
- 201000001223 septic arthritis Diseases 0.000 description 1
- 229960001153 serine Drugs 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 229940083466 soybean lecithin Drugs 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000011146 sterile filtration Methods 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 230000000475 sunscreen effect Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 241001148471 unidentified anaerobic bacterium Species 0.000 description 1
- 208000011479 upper respiratory tract disease Diseases 0.000 description 1
- 208000000143 urethritis Diseases 0.000 description 1
- 208000019206 urinary tract infection Diseases 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000002446 δ-tocopherol Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/445—Non condensed piperidines, e.g. piperocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Dermatology (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3902079A DE3902079A1 (de) | 1988-04-15 | 1989-01-25 | I.m. injektionsformen von gyrase-inhibitoren |
| ES89105795T ES2038359T3 (es) | 1988-04-15 | 1989-04-03 | Procedimiento para la obtencion de formulaciones inyectables intramusculares de inhibidores de girasa. |
| AT89105795T ATE77235T1 (de) | 1988-04-15 | 1989-04-03 | I.m. injektionsformen von gyrase-inhibitoren. |
| DE8989105795T DE58901663D1 (de) | 1988-04-15 | 1989-04-03 | I.m. injektionsformen von gyrase-inhibitoren. |
| EP89105795A EP0337231B1 (de) | 1988-04-15 | 1989-04-03 | i.m. Injektionsformen von Gyrase-Inhibitoren |
| IL89928A IL89928A (en) | 1988-04-15 | 1989-04-12 | Intramuscular injection formulations of gyrase inhibitors |
| JP1090887A JPH01316321A (ja) | 1988-04-15 | 1989-04-12 | ギラーゼ抑制因子の筋肉注射剤 |
| AU32753/89A AU610380B2 (en) | 1988-04-15 | 1989-04-12 | Novel compounds |
| NZ228708A NZ228708A (en) | 1988-04-15 | 1989-04-12 | Quinoline carboxylic acid pharmaceutical formulations for injection |
| CA000596557A CA1336822C (en) | 1988-04-15 | 1989-04-13 | Intramuscular injection forms of gyrase inhibitors |
| DK181389A DK169772B1 (da) | 1988-04-15 | 1989-04-14 | Intramuskulære injektionsformuleringer af gyraseinhibitorer og deres fremstilling |
| HU891867A HUT54048A (en) | 1988-04-15 | 1989-04-14 | Process for producing intramuscular giraze-inhibiting pharmaceutical compositions |
| IE120189A IE60407B1 (en) | 1988-04-15 | 1989-04-14 | Intramuscular injection forms of gyrase inhibitors |
| KR1019890004958A KR900015736A (ko) | 1988-04-15 | 1989-04-14 | 기라제 억제제의 근육내 주사 제형 |
| CN89102284A CN1037272A (zh) | 1988-04-15 | 1989-04-15 | 促旋酶抑制剂的肌内注射剂 |
| US07/549,664 US5023257A (en) | 1988-04-15 | 1990-07-06 | Intramuscular injection forms of gyrase inhibitors |
| GR920401742T GR3005415T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1988-04-15 | 1992-08-11 |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3812508 | 1988-04-15 | ||
| DE3902079A DE3902079A1 (de) | 1988-04-15 | 1989-01-25 | I.m. injektionsformen von gyrase-inhibitoren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3902079A1 true DE3902079A1 (de) | 1989-10-26 |
Family
ID=25866993
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3902079A Withdrawn DE3902079A1 (de) | 1988-04-15 | 1989-01-25 | I.m. injektionsformen von gyrase-inhibitoren |
| DE8989105795T Expired - Lifetime DE58901663D1 (de) | 1988-04-15 | 1989-04-03 | I.m. injektionsformen von gyrase-inhibitoren. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE8989105795T Expired - Lifetime DE58901663D1 (de) | 1988-04-15 | 1989-04-03 | I.m. injektionsformen von gyrase-inhibitoren. |
Country Status (15)
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2655545B1 (fr) * | 1989-12-11 | 1994-06-10 | Rhone Poulenc Sante | Nouvelle application therapeutique des derives des fluoroquinolones. |
| FR2665635A1 (fr) * | 1990-08-10 | 1992-02-14 | Merck Sharp & Dohme | Composition pharmaceutique fluide a base d'un complexe metallique et son procede de preparation. |
| US5420124A (en) * | 1994-01-12 | 1995-05-30 | Kim; Young S. | Stable, painless piroxicam potassium injectable composition |
| US5843930A (en) * | 1995-06-06 | 1998-12-01 | Bayer Corporation | Method of treating otitis with ciprofloxacin-hydrocortisone suspension |
| ATE214931T1 (de) * | 1995-06-06 | 2002-04-15 | Bayer Ag | Antibakterielle präparate für die ohren ohne irritierende, sensibilisierende und ototoxische wirkungen |
| UA56151C2 (uk) * | 1995-12-21 | 2003-05-15 | Пфайзер, Інк. | Водний ін'єкційний розчин данофлоксацину (варіанти) та спосіб лікування бактеріальних інфекцій |
| IN186245B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1997-09-19 | 2001-07-14 | Ranbaxy Lab Ltd | |
| ID21415A (id) | 1997-12-05 | 1999-06-10 | Upjohn Co | Senyawa-senyawa antibiotik magnesium quinolon |
| WO2001052846A1 (en) * | 2000-01-18 | 2001-07-26 | Vertex Pharmaceuticals Incorporated | Gyrase inhibitors and uses thereof |
| US20030170858A1 (en) * | 2001-01-16 | 2003-09-11 | Paul Charifson | Gyrase inhibitors and uses thereof |
| WO2003077842A2 (en) * | 2002-03-12 | 2003-09-25 | Bristol-Myers Squibb Company | Palatable oral suspension and method |
| ES2424676T3 (es) | 2003-09-10 | 2013-10-07 | Kyorin Pharmaceutical Co., Ltd. | Derivado de ácido 7-(3-ciclopropilaminometil-1-pirrolidinil 4-sustituido)quinoloncarboxílico |
| US20070196398A1 (en) * | 2006-02-17 | 2007-08-23 | Murthy Yerramilli V S | Fluoroquinolone fatty acid salt compositions |
| EP2149571A4 (en) | 2007-05-24 | 2010-09-01 | Kyorin Seiyaku Kk | MUTILINE DERIVATIVE WITH A RINGED, HETEROCYCLIC AND AROMATIC CARBOXYLIC ACID STRUCTURE IN A SUBSTITUTE AT POSITION 14 |
| CN102716072B (zh) * | 2012-06-13 | 2014-06-18 | 广州南新制药有限公司 | 一种乳酸环丙沙星氯化钠注射液的制备方法 |
| BR112015021902B1 (pt) * | 2013-03-15 | 2021-06-15 | Iris International, Inc | Líquido para alinhamento de partícula e organela intracelular |
| CN105074422B (zh) | 2013-03-15 | 2019-07-09 | 艾瑞思国际股份有限公司 | 用于染色和样品处理的方法和组合物 |
| US9393243B1 (en) | 2015-07-14 | 2016-07-19 | Nilesh Parikh | Topical Ciprofloxacin compositions |
| ITUB20155193A1 (it) * | 2015-11-03 | 2017-05-03 | Italfarmaco Spa | Sospensioni orali di Givinostat fisicamente e chimicamente stabili |
Family Cites Families (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE564864A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| US4181721A (en) * | 1975-10-27 | 1980-01-01 | Schering Aktiengesellschaft | Depot preparations in an oily, unsaturated solution for intramuscular injection |
| US4620007A (en) * | 1980-09-03 | 1986-10-28 | Bayer Aktiengesellschaft | 6-fluoro-7-chloro-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid |
| US4670444B1 (en) * | 1980-09-03 | 1999-02-09 | Bayer Ag | and-naphthyridine-3-carboxylic acids and antibacte7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-quinoline-rial agents containing these compounds |
| DE3033157A1 (de) * | 1980-09-03 | 1982-04-01 | Bayer Ag, 5090 Leverkusen | 7-amino-1-cyclopropyl-4-oxo-1,4-dihydro-naphthyridin-3-carbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306772A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinolonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3306771A1 (de) * | 1983-02-25 | 1984-08-30 | Bayer Ag, 5090 Leverkusen | Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel |
| DE3324192A1 (de) * | 1983-07-05 | 1985-01-17 | Troponwerke Gmbh & Co Kg | Depot-antiphlogistika |
| DE3333719A1 (de) * | 1983-09-17 | 1985-04-04 | Bayer Ag | Loesungen milchsaurer salze von piperazinylchinolon- und piperazinyl-azachinoloncarbonsaeuren |
| DE3517709A1 (de) * | 1985-01-05 | 1986-07-10 | Bayer Ag | Basische zubereitungen von chinoloncarbonsaeuren |
| DE3522406A1 (de) * | 1985-06-22 | 1987-01-02 | Bayer Ag | Verfahren zur herstellung von 1,8-verbrueckten 4-chinolon-3-carbonsaeuren |
| DE3608745A1 (de) * | 1985-07-24 | 1987-01-29 | Bayer Ag | Bakterizide zubereitungen zur anwendung auf dem gebiet der veterinaermedizin |
| US4816247A (en) * | 1985-09-11 | 1989-03-28 | American Cyanamid Company | Emulsion compositions for administration of sparingly water soluble ionizable hydrophobic drugs |
| IN166416B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1985-09-18 | 1990-05-05 | Pfizer | |
| DE3537761A1 (de) * | 1985-10-24 | 1987-04-30 | Bayer Ag | Infusionsloesungen der 1-cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7- (1-piperazinyl)-chinolin-3-carbonsaeure |
| DE3542972A1 (de) * | 1985-12-05 | 1987-06-11 | Merck Patent Gmbh | Pharmakadepot |
| DE3705621C2 (de) * | 1986-02-25 | 1997-01-09 | Otsuka Pharma Co Ltd | Heterocyclisch substituierte Chinoloncarbonsäurederivate |
| DE3623757A1 (de) * | 1986-07-15 | 1988-01-21 | Bayer Ag | Neue 1,8-verbrueckte 4-chinoloncarbonsaeuren und diese enthaltende arzneimittel |
| IL80459A (en) * | 1986-10-30 | 1991-04-15 | Abic Ltd | Water-soluble adduct of norfloxacin and nicotinic acid |
| DE3713672A1 (de) * | 1987-04-24 | 1988-11-17 | Bayer Ag | Verfahren zur herstellung von parenteral verabreichbaren chinoloncarbonsaeuren |
| US4933335A (en) * | 1987-08-07 | 1990-06-12 | Warner-Lambert Company | Quinolones as antibacterial agents |
| US4803205A (en) * | 1987-08-07 | 1989-02-07 | Warner-Lambert Company | Quinolones as antibacterial agents |
| US4780468A (en) * | 1987-08-07 | 1988-10-25 | Warner-Lambert Company | 8-trifluoromethyl quinolones as antibacterial agents |
| US4839355A (en) * | 1987-09-09 | 1989-06-13 | Sterling Drug Inc. | Tricyclic-pyridinylquinoline compounds, their preparation and use |
-
1989
- 1989-01-25 DE DE3902079A patent/DE3902079A1/de not_active Withdrawn
- 1989-04-03 EP EP89105795A patent/EP0337231B1/de not_active Expired - Lifetime
- 1989-04-03 ES ES89105795T patent/ES2038359T3/es not_active Expired - Lifetime
- 1989-04-03 DE DE8989105795T patent/DE58901663D1/de not_active Expired - Lifetime
- 1989-04-12 JP JP1090887A patent/JPH01316321A/ja active Pending
- 1989-04-12 IL IL89928A patent/IL89928A/xx not_active IP Right Cessation
- 1989-04-12 AU AU32753/89A patent/AU610380B2/en not_active Ceased
- 1989-04-12 NZ NZ228708A patent/NZ228708A/en unknown
- 1989-04-13 CA CA000596557A patent/CA1336822C/en not_active Expired - Fee Related
- 1989-04-14 DK DK181389A patent/DK169772B1/da not_active IP Right Cessation
- 1989-04-14 KR KR1019890004958A patent/KR900015736A/ko not_active Ceased
- 1989-04-14 HU HU891867A patent/HUT54048A/hu unknown
- 1989-04-14 IE IE120189A patent/IE60407B1/en not_active IP Right Cessation
- 1989-04-15 CN CN89102284A patent/CN1037272A/zh active Pending
-
1990
- 1990-07-06 US US07/549,664 patent/US5023257A/en not_active Expired - Fee Related
-
1992
- 1992-08-11 GR GR920401742T patent/GR3005415T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1336822C (en) | 1995-08-29 |
| DK181389A (da) | 1989-10-31 |
| EP0337231B1 (de) | 1992-06-17 |
| HUT54048A (en) | 1991-01-28 |
| AU610380B2 (en) | 1991-05-16 |
| US5023257A (en) | 1991-06-11 |
| IE60407B1 (en) | 1994-07-13 |
| IE891201L (en) | 1989-10-15 |
| JPH01316321A (ja) | 1989-12-21 |
| EP0337231A2 (de) | 1989-10-18 |
| AU3275389A (en) | 1989-10-19 |
| DK181389D0 (da) | 1989-04-14 |
| EP0337231A3 (en) | 1990-01-17 |
| ES2038359T3 (es) | 1995-04-01 |
| IL89928A0 (en) | 1989-12-15 |
| DE58901663D1 (de) | 1992-07-23 |
| CN1037272A (zh) | 1989-11-22 |
| GR3005415T3 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1993-05-24 |
| IL89928A (en) | 1993-05-13 |
| DK169772B1 (da) | 1995-02-27 |
| NZ228708A (en) | 1992-06-25 |
| KR900015736A (ko) | 1990-11-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE3902079A1 (de) | I.m. injektionsformen von gyrase-inhibitoren | |
| EP0219784B1 (de) | Infusionslösungen der 1-Cyclopropyl-6-fluor-1,4-dihydro-4-oxo-7-(1-piperazinyl)-chinolon-3-carbonsäure | |
| EP1778238B1 (de) | Lagerstabile infusionslösung von dihydropteridinonen | |
| CN102341125B (zh) | 包含头孢噻呋和酮洛芬或头孢噻呋和苯甲醇的配制剂 | |
| DE69728783T2 (de) | Verbesserte arzneimittel | |
| DE3702393A1 (de) | 8-cyano-1-cyclopropyl-1,4-dihydro-4-oxo- 3-chinolincarbonsaeuren, verfahren zu ihrer herstellung und diese enthaltende antibakterielle mittel | |
| DE3037102A1 (de) | Verbesserungen bei cephalosporinantibiotika | |
| CA1273578A (en) | Basic formulations of quinolonecarboxylic acids | |
| EP2340809A2 (de) | Arzneimittel enthaltend Fluorchinolone | |
| DE3910663A1 (de) | 5-alkylchinoloncarbonsaeuren | |
| CN110279698A (zh) | 头孢特咯瓒抗生素组合物 | |
| EP0210513A1 (de) | Zubereitungen zur Behandlung von Mycoplasmosen und bakteriellen Erkrankungen bei Geflügel | |
| DE602004013035T2 (de) | Suspension von loteprednol-etabonat und tobramycin für die topische ophthalmische anwendung | |
| US4772460A (en) | Method of reducing the swelling or pain associated with antibiotics compositions | |
| DE69832115T2 (de) | Verfahren zum Stabilisieren von Arylcarbonsäuren, dafür verwendbarer Stabilisator und eine stabilisierte Carbonsäure enthaltende wässrige Lösung | |
| EP1656143B1 (de) | Chinolon-antibiotika zur behandlung von periodontaler infektionen | |
| JP2001278788A (ja) | アラントインを配合した安定な液剤 | |
| DE60113807T2 (de) | Stabilisierte pharmazeutische zusammensetzungen und verfahren zu ihrer herstellung, mit einem antibiotikum und einem expektorans | |
| DE202005022066U1 (de) | Behandlung von Mastitis | |
| CN107375211B (zh) | 一种甲苯磺酸妥舒沙星小儿用舌下喷雾剂及其制备方法 | |
| KR101776274B1 (ko) | 동물용 복합 항생제 조성물 및 이의 제조방법 | |
| KR101352867B1 (ko) | 동물용 복합항생제 조성물 | |
| EP2529728A1 (en) | Pharmaceutical compositions for the treatment of bacterial infections | |
| RU2531937C2 (ru) | Состав и способ получения глазной мази | |
| DE69231423T2 (de) | Verfahren und Zusammensetzung zur Behandlung von Infektionen unter Verwendung von optisch reinem (R) - Lomefloxacin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8130 | Withdrawal |