TWI262181B - Florfenicol prodrug having improved water solubility - Google Patents
Florfenicol prodrug having improved water solubility Download PDFInfo
- Publication number
- TWI262181B TWI262181B TW093139689A TW93139689A TWI262181B TW I262181 B TWI262181 B TW I262181B TW 093139689 A TW093139689 A TW 093139689A TW 93139689 A TW93139689 A TW 93139689A TW I262181 B TWI262181 B TW I262181B
- Authority
- TW
- Taiwan
- Prior art keywords
- alkyl
- group
- phosphate
- chloramphenicol
- acid
- Prior art date
Links
- 239000000651 prodrug Substances 0.000 title claims abstract description 47
- 229940002612 prodrug Drugs 0.000 title claims abstract description 47
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract description 20
- AYIRNRDRBQJXIF-NXEZZACHSA-N (-)-Florfenicol Chemical compound CS(=O)(=O)C1=CC=C([C@@H](O)[C@@H](CF)NC(=O)C(Cl)Cl)C=C1 AYIRNRDRBQJXIF-NXEZZACHSA-N 0.000 title abstract description 6
- 229960003760 florfenicol Drugs 0.000 title abstract 3
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 claims description 68
- 229960005091 chloramphenicol Drugs 0.000 claims description 68
- 125000000217 alkyl group Chemical group 0.000 claims description 52
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 claims description 52
- 229910019142 PO4 Inorganic materials 0.000 claims description 50
- 235000021317 phosphate Nutrition 0.000 claims description 50
- 239000010452 phosphate Substances 0.000 claims description 48
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 44
- -1 fluoromethanesulfonyl Chemical group 0.000 claims description 34
- 239000002253 acid Substances 0.000 claims description 32
- 150000003839 salts Chemical class 0.000 claims description 31
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 28
- 150000001768 cations Chemical class 0.000 claims description 23
- 239000007864 aqueous solution Substances 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 15
- 150000001412 amines Chemical class 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 13
- 229910052799 carbon Inorganic materials 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 241000238366 Cephalopoda Species 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- XHKUTQNVGAHLPK-UHFFFAOYSA-N 2-fluorocyclohexa-2,5-diene-1,4-dione Chemical compound FC1=CC(=O)C=CC1=O XHKUTQNVGAHLPK-UHFFFAOYSA-N 0.000 claims description 9
- 239000007789 gas Substances 0.000 claims description 9
- BLFLLBZGZJTVJG-UHFFFAOYSA-N benzocaine Chemical compound CCOC(=O)C1=CC=C(N)C=C1 BLFLLBZGZJTVJG-UHFFFAOYSA-N 0.000 claims description 8
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
- 239000010436 fluorite Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 7
- UQSQSQZYBQSBJZ-UHFFFAOYSA-M fluorosulfonate Chemical compound [O-]S(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-M 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910021653 sulphate ion Inorganic materials 0.000 claims description 7
- 208000035143 Bacterial infection Diseases 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 150000001413 amino acids Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229930188189 sulfomycin Natural products 0.000 claims description 5
- 108010051634 sulfomycin Proteins 0.000 claims description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
- 229960005274 benzocaine Drugs 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 241000894007 species Species 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000004985 diamines Chemical class 0.000 claims description 3
- HGFAGBHAGYXJKZ-UHFFFAOYSA-N fluoromethanesulfonamide Chemical compound NS(=O)(=O)CF HGFAGBHAGYXJKZ-UHFFFAOYSA-N 0.000 claims description 3
- BTZNPZMHENLISZ-UHFFFAOYSA-M fluoromethanesulfonate Chemical compound [O-]S(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-M 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 3
- 229960004919 procaine Drugs 0.000 claims description 3
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 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 claims description 2
- 241000283973 Oryctolagus cuniculus Species 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229920002674 hyaluronan Polymers 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 229960003194 meglumine Drugs 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 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
- 238000000926 separation method Methods 0.000 claims description 2
- 239000004575 stone Substances 0.000 claims description 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- KIUKXJAPPMFGSW-DNGZLQJQSA-N (2S,3S,4S,5R,6R)-6-[(2S,3R,4R,5S,6R)-3-Acetamido-2-[(2S,3S,4R,5R,6R)-6-[(2R,3R,4R,5S,6R)-3-acetamido-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-2-carboxy-4,5-dihydroxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-DNGZLQJQSA-N 0.000 claims 1
- 239000005944 Chlorpyrifos Substances 0.000 claims 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims 1
- 241000555745 Sciuridae Species 0.000 claims 1
- XOCUXOWLYLLJLV-UHFFFAOYSA-N [O].[S] Chemical compound [O].[S] XOCUXOWLYLLJLV-UHFFFAOYSA-N 0.000 claims 1
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 claims 1
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims 1
- 210000004709 eyebrow Anatomy 0.000 claims 1
- UQSQSQZYBQSBJZ-UHFFFAOYSA-N fluorosulfonic acid Chemical compound OS(F)(=O)=O UQSQSQZYBQSBJZ-UHFFFAOYSA-N 0.000 claims 1
- 229960003160 hyaluronic acid Drugs 0.000 claims 1
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 claims 1
- 229940127557 pharmaceutical product Drugs 0.000 claims 1
- 229910052707 ruthenium Inorganic materials 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- USPTVMVRNZEXCP-UHFFFAOYSA-N sulfamoyl fluoride Chemical compound NS(F)(=O)=O USPTVMVRNZEXCP-UHFFFAOYSA-N 0.000 claims 1
- 125000004149 thio group Chemical group *S* 0.000 claims 1
- 125000003396 thiol group Chemical group [H]S* 0.000 claims 1
- 241001465754 Metazoa Species 0.000 abstract description 16
- 238000001727 in vivo Methods 0.000 abstract description 3
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 24
- 241000269817 Centrarchidae Species 0.000 description 12
- 150000002500 ions Chemical class 0.000 description 12
- 239000000052 vinegar Substances 0.000 description 9
- 235000021419 vinegar Nutrition 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000019688 fish Nutrition 0.000 description 8
- 241000282472 Canis lupus familiaris Species 0.000 description 7
- 206010036790 Productive cough Diseases 0.000 description 7
- 241000282887 Suidae Species 0.000 description 7
- 244000309466 calf Species 0.000 description 7
- 210000003802 sputum Anatomy 0.000 description 7
- 208000024794 sputum Diseases 0.000 description 7
- 241000283690 Bos taurus Species 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 241000251468 Actinopterygii Species 0.000 description 5
- 241000972773 Aulopiformes Species 0.000 description 5
- 241000700159 Rattus Species 0.000 description 5
- 241000239226 Scorpiones Species 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 235000019515 salmon Nutrition 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 229930002875 chlorophyll Natural products 0.000 description 4
- 235000019804 chlorophyll Nutrition 0.000 description 4
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000012091 fetal bovine serum Substances 0.000 description 4
- 241000272517 Anseriformes Species 0.000 description 3
- 241000271566 Aves Species 0.000 description 3
- 241000276616 Cichlidae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000283073 Equus caballus Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000408747 Lepomis gibbosus Species 0.000 description 3
- XNOPRXBHLZRZKH-UHFFFAOYSA-N Oxytocin Natural products N1C(=O)C(N)CSSCC(C(=O)N2C(CCC2)C(=O)NC(CC(C)C)C(=O)NCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(CCC(N)=O)NC(=O)C(C(C)CC)NC(=O)C1CC1=CC=C(O)C=C1 XNOPRXBHLZRZKH-UHFFFAOYSA-N 0.000 description 3
- 101800000989 Oxytocin Proteins 0.000 description 3
- 102100031951 Oxytocin-neurophysin 1 Human genes 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- BTZNPZMHENLISZ-UHFFFAOYSA-N fluoromethanesulfonic acid Chemical compound OS(=O)(=O)CF BTZNPZMHENLISZ-UHFFFAOYSA-N 0.000 description 3
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 238000001990 intravenous administration Methods 0.000 description 3
- 239000008267 milk Substances 0.000 description 3
- 210000004080 milk Anatomy 0.000 description 3
- 235000013336 milk Nutrition 0.000 description 3
- 229960001723 oxytocin Drugs 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- ROWKJAVDOGWPAT-UHFFFAOYSA-N Acetoin Chemical compound CC(O)C(C)=O ROWKJAVDOGWPAT-UHFFFAOYSA-N 0.000 description 2
- 241001559555 Ambloplites rupestris Species 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241001085763 Centropristis striata Species 0.000 description 2
- 229940126062 Compound A Drugs 0.000 description 2
- 241000611752 Coregonus clupeaformis Species 0.000 description 2
- 241001155417 Enneacanthus gloriosus Species 0.000 description 2
- 241001656472 Epinephelus morio Species 0.000 description 2
- 241000283086 Equidae Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 241000947653 Fontinalis Species 0.000 description 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 2
- 241000442132 Lactarius lactarius Species 0.000 description 2
- 241000489982 Lagodon rhomboides Species 0.000 description 2
- 241001155442 Lepomis cyanellus Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 241000277326 Oncorhynchus gorbuscha Species 0.000 description 2
- 241000277275 Oncorhynchus mykiss Species 0.000 description 2
- 241000277277 Oncorhynchus nerka Species 0.000 description 2
- 241001494479 Pecora Species 0.000 description 2
- 241000277288 Salmo trutta Species 0.000 description 2
- 241000277297 Salvelinus leucomaenis Species 0.000 description 2
- 241000207929 Scutellaria Species 0.000 description 2
- 241001417495 Serranidae Species 0.000 description 2
- 241000675916 Serranus phoebe Species 0.000 description 2
- 241000276707 Tilapia Species 0.000 description 2
- 229940088710 antibiotic agent Drugs 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000001647 drug administration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 description 2
- 229960002464 fluoxetine Drugs 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 2
- 244000144972 livestock Species 0.000 description 2
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 230000036470 plasma concentration Effects 0.000 description 2
- 244000144977 poultry Species 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 239000000932 sedative agent Substances 0.000 description 2
- 230000001624 sedative effect Effects 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 229940124530 sulfonamide Drugs 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- YWILDZMVBIMXID-KGHBUBBXSA-N (4s,4as,5as,6s,12ar)-n-[[4-[n-(diaminomethylidene)carbamimidoyl]piperazin-1-yl]methyl]-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;dihydrochloride Chemical class Cl.Cl.OC([C@@]1(O)C(=O)C=2[C@@H]([C@](C3=CC=CC(O)=C3C=2O)(C)O)C[C@H]1[C@@H](C1=O)N(C)C)=C1C(=O)NCN1CCN(C(=N)N=C(N)N)CC1 YWILDZMVBIMXID-KGHBUBBXSA-N 0.000 description 1
- 150000004345 1,2-dihydroxyanthraquinones Chemical class 0.000 description 1
- VIESAWGOYVNHLV-UHFFFAOYSA-N 1,3-dihydropyrrol-2-one Chemical compound O=C1CC=CN1 VIESAWGOYVNHLV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-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
- FTMJFHVKAXPFIY-RKDXNWHRSA-N 2,2-dichloro-n-[(1r,2r)-1,3-dihydroxy-1-(3-nitrophenyl)propan-2-yl]acetamide Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=CC([N+]([O-])=O)=C1 FTMJFHVKAXPFIY-RKDXNWHRSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- 241001519451 Abramis brama Species 0.000 description 1
- 241001609368 Acamptopappus Species 0.000 description 1
- OYMZTORLGBISLR-UHFFFAOYSA-N Acetomycin Natural products CC1C(OC(C)=O)OC(=O)C1(C)C(C)=O OYMZTORLGBISLR-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 241000606748 Actinobacillus pleuropneumoniae Species 0.000 description 1
- 241000607525 Aeromonas salmonicida Species 0.000 description 1
- 241001580935 Aglossa pinguinalis Species 0.000 description 1
- 241000219498 Alnus glutinosa Species 0.000 description 1
- 241000705529 Andinoacara pulcher Species 0.000 description 1
- 241000264349 Archosargus probatocephalus Species 0.000 description 1
- 241000473391 Archosargus rhomboidalis Species 0.000 description 1
- 240000005528 Arctium lappa Species 0.000 description 1
- 235000003130 Arctium lappa Nutrition 0.000 description 1
- 235000008078 Arctium minus Nutrition 0.000 description 1
- 235000000832 Ayote Nutrition 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 241000167854 Bourreria succulenta Species 0.000 description 1
- 241000889236 Calamus penna Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 241000700198 Cavia Species 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- 241001155433 Centrarchus macropterus Species 0.000 description 1
- 241000758604 Centropristis ocyurus Species 0.000 description 1
- 241000758603 Centropristis philadelphica Species 0.000 description 1
- 241000282693 Cercopithecidae Species 0.000 description 1
- 241001155440 Chaenobryttus gulosus Species 0.000 description 1
- 241000272470 Circus Species 0.000 description 1
- 235000009917 Crataegus X brevipes Nutrition 0.000 description 1
- 235000013204 Crataegus X haemacarpa Nutrition 0.000 description 1
- 235000009685 Crataegus X maligna Nutrition 0.000 description 1
- 235000009444 Crataegus X rubrocarnea Nutrition 0.000 description 1
- 235000009486 Crataegus bullatus Nutrition 0.000 description 1
- 235000017181 Crataegus chrysocarpa Nutrition 0.000 description 1
- 235000009682 Crataegus limnophila Nutrition 0.000 description 1
- 235000004423 Crataegus monogyna Nutrition 0.000 description 1
- 240000000171 Crataegus monogyna Species 0.000 description 1
- 235000002313 Crataegus paludosa Nutrition 0.000 description 1
- 235000009840 Crataegus x incaedua Nutrition 0.000 description 1
- 241000320737 Crenicichla lacustris Species 0.000 description 1
- 241000938605 Crocodylia Species 0.000 description 1
- 240000004244 Cucurbita moschata Species 0.000 description 1
- 235000009854 Cucurbita moschata Nutrition 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 241001020588 Diplectrum bivittatum Species 0.000 description 1
- 241000275449 Diplectrum formosum Species 0.000 description 1
- 241000949274 Edwardsiella ictaluri Species 0.000 description 1
- 241001236173 Elassoma okefenokee Species 0.000 description 1
- 241001236171 Elassoma zonatum Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241001236158 Enneacanthus Species 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 241000194033 Enterococcus Species 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 206010016761 Flat chest Diseases 0.000 description 1
- 241000605952 Fusobacterium necrophorum Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000545744 Hirudinea Species 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000321408 Hyporthodus flavolimbatus Species 0.000 description 1
- 241000588748 Klebsiella Species 0.000 description 1
- FBOZXECLQNJBKD-ZDUSSCGKSA-N L-methotrexate Chemical compound C=1N=C2N=C(N)N=C(N)C2=NC=1CN(C)C1=CC=C(C(=O)N[C@@H](CCC(O)=O)C(O)=O)C=C1 FBOZXECLQNJBKD-ZDUSSCGKSA-N 0.000 description 1
- 241000721656 Lepomis Species 0.000 description 1
- 241001155465 Lepomis auritus Species 0.000 description 1
- 241000721654 Lepomis macrochirus Species 0.000 description 1
- 241000408783 Lepomis megalotis Species 0.000 description 1
- 241000772413 Lutrogale perspicillata Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 241000290125 Micropterus coosae Species 0.000 description 1
- 241001328758 Micropterus dolomieu Species 0.000 description 1
- 241000290127 Micropterus punctulatus Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241001417899 Oncorhynchus clarkii Species 0.000 description 1
- 241000277329 Oncorhynchus keta Species 0.000 description 1
- 241000277338 Oncorhynchus kisutch Species 0.000 description 1
- 241000277269 Oncorhynchus masou Species 0.000 description 1
- 241001280377 Oncorhynchus tshawytscha Species 0.000 description 1
- 241000276719 Oreochromis Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000170916 Paeonia officinalis Species 0.000 description 1
- 235000006484 Paeonia officinalis Nutrition 0.000 description 1
- 241001282110 Pagrus major Species 0.000 description 1
- 241001396961 Parapristipoma trilineatum Species 0.000 description 1
- 241000606856 Pasteurella multocida Species 0.000 description 1
- 241001247287 Pentalinon luteum Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- 235000008331 Pinus X rigitaeda Nutrition 0.000 description 1
- 241000018646 Pinus brutia Species 0.000 description 1
- 235000011613 Pinus brutia Nutrition 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 241001155420 Pomoxis annularis Species 0.000 description 1
- 241000269816 Pomoxis nigromaculatus Species 0.000 description 1
- 241001135223 Prevotella melaninogenica Species 0.000 description 1
- 241000288906 Primates Species 0.000 description 1
- 241000767458 Prosopium cylindraceum Species 0.000 description 1
- 241000588769 Proteus <enterobacteria> Species 0.000 description 1
- 240000004350 Prunus spinosa Species 0.000 description 1
- 235000010829 Prunus spinosa Nutrition 0.000 description 1
- 241001260334 Pterophyllum scalare Species 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 240000005578 Rivina humilis Species 0.000 description 1
- 241000283984 Rodentia Species 0.000 description 1
- 241000277263 Salmo Species 0.000 description 1
- 241000277289 Salmo salar Species 0.000 description 1
- 241001138501 Salmonella enterica Species 0.000 description 1
- 241000277331 Salmonidae Species 0.000 description 1
- 241000276677 Sarotherodon Species 0.000 description 1
- 241001417494 Sciaenidae Species 0.000 description 1
- 241001290266 Sciaenops ocellatus Species 0.000 description 1
- 241001282153 Scopelogadus mizolepis Species 0.000 description 1
- 241001521797 Scorpaena notata Species 0.000 description 1
- 206010040047 Sepsis Diseases 0.000 description 1
- 241000287219 Serinus canaria Species 0.000 description 1
- 241000347374 Serranus Species 0.000 description 1
- 241000675264 Serranus tortugarum Species 0.000 description 1
- 241000607768 Shigella Species 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-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
- 241000269788 Sparidae Species 0.000 description 1
- 241000269808 Sparus Species 0.000 description 1
- 241000063156 Squatina squatina Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241001494108 Stenotomus Species 0.000 description 1
- 241001494106 Stenotomus chrysops Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000271567 Struthioniformes Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 241000270666 Testudines Species 0.000 description 1
- 208000037386 Typhoid Diseases 0.000 description 1
- HRVQDBZKORPEPG-UHFFFAOYSA-N [F].COS(O)(=O)=O Chemical compound [F].COS(O)(=O)=O HRVQDBZKORPEPG-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- OYMZTORLGBISLR-RHFNHBFPSA-N acetomycin Chemical compound C[C@@H]1[C@H](OC(C)=O)OC(=O)[C@]1(C)C(C)=O OYMZTORLGBISLR-RHFNHBFPSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CJFCGSLFEZPBNJ-UHFFFAOYSA-N carbamimidoylazanium;phosphate Chemical compound NC([NH3+])=N.NC([NH3+])=N.NC([NH3+])=N.[O-]P([O-])([O-])=O CJFCGSLFEZPBNJ-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 230000000739 chaotic effect Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000019693 cherries Nutrition 0.000 description 1
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 description 1
- 229910001919 chlorite Inorganic materials 0.000 description 1
- 229910052619 chlorite group Inorganic materials 0.000 description 1
- HCXRJZPKQRLSCW-UHFFFAOYSA-N chloroform;sulfuric acid Chemical compound ClC(Cl)Cl.OS(O)(=O)=O HCXRJZPKQRLSCW-UHFFFAOYSA-N 0.000 description 1
- QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910000397 disodium phosphate Inorganic materials 0.000 description 1
- 235000019800 disodium phosphate Nutrition 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 208000028104 epidemic louse-borne typhus Diseases 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 1
- 210000003746 feather Anatomy 0.000 description 1
- 230000001605 fetal effect Effects 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- NBVXSUQYWXRMNV-OUBTZVSYSA-N fluoromethane Chemical class F[13CH3] NBVXSUQYWXRMNV-OUBTZVSYSA-N 0.000 description 1
- VSAVIUSEFTYPSF-UHFFFAOYSA-N fluoromethanesulfinic acid Chemical compound OS(=O)CF VSAVIUSEFTYPSF-UHFFFAOYSA-N 0.000 description 1
- NNINWAWDVUHMGM-UHFFFAOYSA-N fluoromethanesulfonyl chloride Chemical compound FCS(Cl)(=O)=O NNINWAWDVUHMGM-UHFFFAOYSA-N 0.000 description 1
- AIUYAMGZOLZABQ-PMYHJQRFSA-N fluoromycin Chemical compound O([C@H]1[C@@H]([C@H](O)[C@H](N)[C@H](C)O1)O)C(C(O)C=1SC=C(N=1)C=1SC(=CN=1)C(=O)NCCCCNC(=S)NC=1C=C2C(C3(C4=CC=C(O)C=C4OC4=CC(O)=CC=C43)OC2=O)=CC=1)NC(=O)C(C(O)C)NC(=O)CC(O)C(C)NC(=O)C(C(O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)NC(=O)C1=NC(C(CC(N)=O)NCC(N)C(N)=O)=NC(N)=C1C AIUYAMGZOLZABQ-PMYHJQRFSA-N 0.000 description 1
- 108700007815 fluoromycin Proteins 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- KIUKXJAPPMFGSW-MNSSHETKSA-N hyaluronan Chemical compound CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)C1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H](C(O[C@H]3[C@@H]([C@@H](O)[C@H](O)[C@H](O3)C(O)=O)O)[C@H](O)[C@@H](CO)O2)NC(C)=O)[C@@H](C(O)=O)O1 KIUKXJAPPMFGSW-MNSSHETKSA-N 0.000 description 1
- 229940099552 hyaluronan Drugs 0.000 description 1
- GFAZHVHNLUBROE-UHFFFAOYSA-N hydroxymethyl propionaldehyde Natural products CCC(=O)CO GFAZHVHNLUBROE-UHFFFAOYSA-N 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- 229960001252 methamphetamine Drugs 0.000 description 1
- 229960000485 methotrexate Drugs 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- TTWJBBZEZQICBI-UHFFFAOYSA-N metoclopramide Chemical class CCN(CC)CCNC(=O)C1=CC(Cl)=C(N)C=C1OC TTWJBBZEZQICBI-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- XONPDZSGENTBNJ-UHFFFAOYSA-N molecular hydrogen;sodium Chemical compound [Na].[H][H] XONPDZSGENTBNJ-UHFFFAOYSA-N 0.000 description 1
- 229930003658 monoterpene Natural products 0.000 description 1
- 150000002773 monoterpene derivatives Chemical class 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 229940060568 nuflor Drugs 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 238000006213 oxygenation reaction Methods 0.000 description 1
- XNOPRXBHLZRZKH-DSZYJQQASA-N oxytocin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CSSC[C@H](N)C(=O)N1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)=O)[C@@H](C)CC)C1=CC=C(O)C=C1 XNOPRXBHLZRZKH-DSZYJQQASA-N 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229940051027 pasteurella multocida Drugs 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 125000001095 phosphatidyl group Chemical group 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000015136 pumpkin Nutrition 0.000 description 1
- 235000020236 pumpkin seed Nutrition 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000001117 sulphuric acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003535 tetraterpenes Chemical class 0.000 description 1
- 235000009657 tetraterpenes Nutrition 0.000 description 1
- JOPDZQBPOWAEHC-UHFFFAOYSA-H tristrontium;diphosphate Chemical compound [Sr+2].[Sr+2].[Sr+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JOPDZQBPOWAEHC-UHFFFAOYSA-H 0.000 description 1
- 201000008297 typhoid fever Diseases 0.000 description 1
- 206010061393 typhus Diseases 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
-
- 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
- A61K31/66—Phosphorus compounds
- A61K31/661—Phosphorus acids or esters thereof not having P—C bonds, e.g. fosfosal, dichlorvos, malathion or mevinphos
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/094—Esters of phosphoric acids with arylalkanols
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53222703P | 2003-12-23 | 2003-12-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW200533640A TW200533640A (en) | 2005-10-16 |
| TWI262181B true TWI262181B (en) | 2006-09-21 |
Family
ID=34738768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW093139689A TWI262181B (en) | 2003-12-23 | 2004-12-20 | Florfenicol prodrug having improved water solubility |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US7153842B2 (enExample) |
| EP (1) | EP1696934B1 (enExample) |
| JP (2) | JP4719160B2 (enExample) |
| KR (1) | KR20060111605A (enExample) |
| CN (1) | CN100579532C (enExample) |
| AR (1) | AR046970A1 (enExample) |
| BR (1) | BRPI0418133A2 (enExample) |
| CA (1) | CA2550660C (enExample) |
| EC (1) | ECSP066670A (enExample) |
| IL (2) | IL176342A (enExample) |
| MX (1) | MXPA06007215A (enExample) |
| NO (1) | NO20063244L (enExample) |
| NZ (1) | NZ547592A (enExample) |
| PE (1) | PE20050822A1 (enExample) |
| RU (1) | RU2006126519A (enExample) |
| TW (1) | TWI262181B (enExample) |
| WO (1) | WO2005063257A1 (enExample) |
| ZA (1) | ZA200605165B (enExample) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PE20050386A1 (es) | 2003-05-29 | 2005-06-23 | Schering Plough Ltd | Composiciones farmaceuticas de florfenicol |
| US7439268B2 (en) | 2003-07-18 | 2008-10-21 | Idexx Laboratories | Compositions containing prodrugs of florfenicol and methods of use |
| EP1696934B1 (en) * | 2003-12-23 | 2013-05-29 | Schering-Plough Ltd. | Florfenicol prodrug having improved water solubility |
| WO2005066119A2 (en) * | 2003-12-31 | 2005-07-21 | Schering-Plough Ltd. | Antibacterial 1-(4-mono-and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanols and preparation thereof |
| DE602005009381D1 (de) | 2004-09-23 | 2008-10-09 | Schering Plough Ltd | Bekämpfung von parasiten in tieren durch verwendung neuer trifluormethansulfonanilidoximetherderivate |
| JP4750126B2 (ja) | 2004-11-19 | 2011-08-17 | シェーリング−プラウ・リミテッド | 殺寄生虫薬２−フェニル−３−（１ｈ−ピロール−２−イル）アクリロニトリル誘導体の使用による動物における寄生虫の制御 |
| EP1890547A2 (en) * | 2005-06-09 | 2008-02-27 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| WO2008076256A1 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof |
| WO2008076261A2 (en) * | 2006-12-13 | 2008-06-26 | Schering-Plough Ltd. | Water-soluble phenicol prodrugs in a lipophilic vehicle system |
| CN101605756A (zh) * | 2006-12-13 | 2009-12-16 | 先灵-普劳有限公司 | 氟苯尼考及其类似物的水溶性前药 |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| DK2182945T3 (en) | 2007-06-27 | 2015-11-16 | Du Pont | PROCEDURE TO COMBAT PESTS WITH ANIMALS |
| PE20091171A1 (es) * | 2007-12-14 | 2009-08-03 | Schering Plough Ltd | Proceso para recuperar florfenicol y analogos de florfenicol |
| WO2010014566A2 (en) * | 2008-07-30 | 2010-02-04 | Intervet International B.V. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
| AU2010279587A1 (en) | 2009-08-05 | 2012-02-09 | E. I. Du Pont De Nemours And Company | Mesoionic pesticides |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| EP2461684A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| MX2013012820A (es) | 2011-05-02 | 2014-02-10 | Zoetis Llc | Cefalosporinas novedosas utiles como agentes antibacteriales. |
| US20140113934A1 (en) | 2011-06-20 | 2014-04-24 | E I Du Pont De Nemours And Company | Heterocyclic compounds for treating helminth infections |
| JP2015502936A (ja) | 2011-11-28 | 2015-01-29 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | スルホンアミド駆虫薬 |
| WO2013158422A1 (en) | 2012-04-17 | 2013-10-24 | E. I. Du Pont De Nemours And Company | Heterocyclic compounds for controlling invertebrate pests |
| WO2014099837A1 (en) | 2012-12-18 | 2014-06-26 | E. I. Du Pont De Nemours And Company | Sulfonamide anthelmintics |
| CN103242363B (zh) * | 2013-04-18 | 2015-10-28 | 湖北龙翔药业有限公司 | 氟苯尼考磷酸二酯及盐及其制备方法 |
| CN103923118A (zh) * | 2014-04-08 | 2014-07-16 | 张家港威胜生物医药有限公司 | 一种水溶性氟苯尼考衍生物的合成方法 |
| CN105111234B (zh) * | 2015-09-23 | 2017-05-17 | 河北远征禾木药业有限公司 | 一种氟苯尼考磷酸酯的合成方法 |
| CN110078729A (zh) * | 2019-06-11 | 2019-08-02 | 石家庄学院 | 一种水溶性氟苯尼考前药及其制备方法 |
| CN115286544A (zh) * | 2022-10-08 | 2022-11-04 | 世华合创生物技术开发(山东)有限公司 | 一种氟苯尼考衍生物、制备方法及其在抗细菌感染的应用 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2776992A (en) | 1956-03-14 | 1957-01-08 | Du Pont | Trifluoromethylsulfonylphenyldichloracetamidopropandiol |
| US4235892A (en) | 1979-02-05 | 1980-11-25 | Schering Corporation, Patent Dept. | 1-Aryl-2-acylamido-3-fluoro-1-propanols, methods for their use as antibacterial agents and compositions useful therefor |
| FR2562543B1 (fr) * | 1984-04-10 | 1987-09-25 | Elf Aquitaine | Nouveaux phosphonites cycliques, leur preparation et applications |
| US5352832A (en) | 1992-12-18 | 1994-10-04 | Schering Corporation | Asymmetric process for preparing florfenicol, thiamphenicol chloramphenicol and oxazoline intermediates |
| US6864240B1 (en) | 1999-06-15 | 2005-03-08 | Elan Pharmaceuticals, Inc. | Dipeptide inhibitors of β-secretase |
| US6670344B2 (en) | 2000-09-14 | 2003-12-30 | Bristol-Myers Squibb Company | Combretastatin A-4 phosphate prodrug mono- and di-organic amine salts, mono- and di- amino acid salts, and mono- and di-amino acid ester salts |
| US7547686B2 (en) | 2001-06-15 | 2009-06-16 | Arizona Board of Regents, a body corporate of the State of Arizona, Acting for and on Behalf of the Arizona State University | Combretastatin A-3 prodrug |
| AU2003249503A1 (en) * | 2002-03-08 | 2003-09-29 | Schering-Plough, Ltd. | Novel florfenicol-type antibiotics |
| US7439268B2 (en) | 2003-07-18 | 2008-10-21 | Idexx Laboratories | Compositions containing prodrugs of florfenicol and methods of use |
| EP1696934B1 (en) * | 2003-12-23 | 2013-05-29 | Schering-Plough Ltd. | Florfenicol prodrug having improved water solubility |
| WO2005066119A2 (en) | 2003-12-31 | 2005-07-21 | Schering-Plough Ltd. | Antibacterial 1-(4-mono-and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoropropanols and preparation thereof |
-
2004
- 2004-12-20 EP EP04814736.7A patent/EP1696934B1/en not_active Expired - Lifetime
- 2004-12-20 US US11/016,794 patent/US7153842B2/en not_active Expired - Lifetime
- 2004-12-20 CN CN200480038867A patent/CN100579532C/zh not_active Expired - Lifetime
- 2004-12-20 CA CA2550660A patent/CA2550660C/en not_active Expired - Fee Related
- 2004-12-20 AR ARP040104805A patent/AR046970A1/es not_active Application Discontinuation
- 2004-12-20 RU RU2006126519/04A patent/RU2006126519A/ru not_active Application Discontinuation
- 2004-12-20 MX MXPA06007215A patent/MXPA06007215A/es active IP Right Grant
- 2004-12-20 NZ NZ547592A patent/NZ547592A/xx not_active IP Right Cessation
- 2004-12-20 TW TW093139689A patent/TWI262181B/zh not_active IP Right Cessation
- 2004-12-20 BR BRPI0418133-6A patent/BRPI0418133A2/pt not_active IP Right Cessation
- 2004-12-20 JP JP2006547183A patent/JP4719160B2/ja not_active Expired - Fee Related
- 2004-12-20 KR KR1020067012460A patent/KR20060111605A/ko not_active Withdrawn
- 2004-12-20 WO PCT/US2004/042591 patent/WO2005063257A1/en not_active Ceased
-
2005
- 2005-01-03 PE PE2005000020A patent/PE20050822A1/es not_active Application Discontinuation
-
2006
- 2006-06-15 IL IL176342A patent/IL176342A/en not_active IP Right Cessation
- 2006-06-22 ZA ZA200605165A patent/ZA200605165B/xx unknown
- 2006-06-22 EC EC2006006670A patent/ECSP066670A/es unknown
- 2006-07-12 NO NO20063244A patent/NO20063244L/no not_active Application Discontinuation
- 2006-08-29 US US11/511,810 patent/US7572777B2/en not_active Expired - Lifetime
-
2009
- 2009-07-23 IL IL200041A patent/IL200041A0/en unknown
-
2011
- 2011-02-23 JP JP2011037689A patent/JP2011148804A/ja not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| EP1696934B1 (en) | 2013-05-29 |
| US7153842B2 (en) | 2006-12-26 |
| JP2011148804A (ja) | 2011-08-04 |
| NO20063244L (no) | 2006-09-20 |
| US20070021387A1 (en) | 2007-01-25 |
| BRPI0418133A2 (pt) | 2009-03-24 |
| MXPA06007215A (es) | 2006-08-18 |
| US20050182031A1 (en) | 2005-08-18 |
| AR046970A1 (es) | 2006-01-04 |
| IL200041A0 (en) | 2010-04-15 |
| EP1696934A1 (en) | 2006-09-06 |
| AU2004308913A1 (en) | 2005-07-14 |
| ECSP066670A (es) | 2006-10-25 |
| WO2005063257A1 (en) | 2005-07-14 |
| CN100579532C (zh) | 2010-01-13 |
| TW200533640A (en) | 2005-10-16 |
| US7572777B2 (en) | 2009-08-11 |
| PE20050822A1 (es) | 2005-10-01 |
| JP2007516286A (ja) | 2007-06-21 |
| CN1897954A (zh) | 2007-01-17 |
| KR20060111605A (ko) | 2006-10-27 |
| RU2006126519A (ru) | 2008-01-27 |
| IL176342A (en) | 2011-08-31 |
| NZ547592A (en) | 2009-07-31 |
| CA2550660A1 (en) | 2005-07-14 |
| CA2550660C (en) | 2011-03-15 |
| IL176342A0 (en) | 2006-10-05 |
| ZA200605165B (en) | 2007-12-27 |
| JP4719160B2 (ja) | 2011-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA2550660C (en) | Florfenicol prodrug having improved water solubility | |
| US7713950B2 (en) | Antibacterial 1-(4-mono-and di-halomethylsulphonylphenyl)-2-acylamino-3-fluoroproponals and preparation thereof | |
| SU1505442A3 (ru) | Способ получени производных оксазолидинона в виде @ -изомеров или смеси @ - и @ -изомеров, или их аддитивных солей с кислотами | |
| CN104470893A (zh) | 氟化2-氨基-4-(苄基氨基)苯基氨基甲酸酯衍生物 | |
| IE60992B1 (en) | Beta-aminoethyl-substituted phenyl compounds, and anti-inflammatory or analgesic compositions containing them | |
| JPH08208662A (ja) | 新規な結晶性セフェム酸付加塩およびその調製方法 | |
| JPS6248678B2 (enExample) | ||
| CS212259B2 (cs) | Způsob výroby cefalosporinů | |
| US20140187527A1 (en) | Macrocyclic Compounds And Metal Complexes For Bioimaging And Biomedical Applications | |
| WO2019245590A1 (en) | Chemical compounds | |
| AU2004308913B2 (en) | Florfenicol prodrug having improved water solubility | |
| JP4249928B2 (ja) | 抗腫瘍剤としてのビス−（ｎ，ｎ’−ビス−（２−ハロエチル）アミノ）ホスホルアミデート | |
| WO2019232662A1 (zh) | 一类具有抗癌活性的吲嗪类化合物及其衍生物 | |
| EP0209000B1 (de) | Embonate von Chinoloncarbonsäuren und ihren Derivaten | |
| JPH09505813A (ja) | ビフェニル沃素化誘導体及びその診断用途 | |
| JPS59193822A (ja) | 腎炎治療剤 | |
| JP2007502259A5 (enExample) | ||
| US4443457A (en) | Aminocrot onylpyridine N-oxides useful as adjuncts to radiation therapy | |
| JPS58154589A (ja) | セフアロスポリン誘導体 | |
| JPH0150235B2 (enExample) | ||
| DE2533930A1 (de) | Transaminomethylcyclohexancarbonsaeurederivate, verfahren zu ihrer herstellung und sie enthaltende arzneimittel | |
| JPS61183292A (ja) | 新規化合物、その製法及びそれを含む製薬組成物 | |
| JPS61205263A (ja) | 豚赤痢の治療および予防のためそして動物発育促進剤として有用なキノキサリン誘導体 | |
| JPH05271065A (ja) | 抗内毒素作用を有する医薬品組成物 | |
| MXPA97007256A (en) | An injectable antiparasitary composition and preparation procedure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |