HRP20000444A2 - Novel erythromycin derivatives - Google Patents
Novel erythromycin derivatives Download PDFInfo
- Publication number
- HRP20000444A2 HRP20000444A2 HR20000444A HRP20000444A HRP20000444A2 HR P20000444 A2 HRP20000444 A2 HR P20000444A2 HR 20000444 A HR20000444 A HR 20000444A HR P20000444 A HRP20000444 A HR P20000444A HR P20000444 A2 HRP20000444 A2 HR P20000444A2
- Authority
- HR
- Croatia
- Prior art keywords
- alkyl
- propyl
- compound according
- formula
- substituted
- Prior art date
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title description 89
- 150000001875 compounds Chemical class 0.000 claims description 347
- -1 C2-C8 alykynyl Chemical group 0.000 claims description 299
- 125000005843 halogen group Chemical group 0.000 claims description 208
- 125000000217 alkyl group Chemical group 0.000 claims description 166
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 127
- 229910052760 oxygen Inorganic materials 0.000 claims description 127
- 229910052717 sulfur Inorganic materials 0.000 claims description 116
- 125000000623 heterocyclic group Chemical group 0.000 claims description 92
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 91
- 229910052799 carbon Inorganic materials 0.000 claims description 87
- 125000001424 substituent group Chemical group 0.000 claims description 84
- 229920006395 saturated elastomer Polymers 0.000 claims description 65
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 63
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 63
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 63
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 63
- 239000011593 sulfur Substances 0.000 claims description 63
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 62
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 62
- 239000001301 oxygen Substances 0.000 claims description 62
- 150000003839 salts Chemical class 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 61
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims description 60
- 238000000034 method Methods 0.000 claims description 55
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 52
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 49
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 46
- 125000002252 acyl group Chemical group 0.000 claims description 43
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 42
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 42
- 125000003545 alkoxy group Chemical group 0.000 claims description 42
- 125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 42
- 125000000304 alkynyl group Chemical group 0.000 claims description 42
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 40
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 39
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 33
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 33
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 33
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 32
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 32
- 238000011282 treatment Methods 0.000 claims description 27
- 150000007524 organic acids Chemical class 0.000 claims description 25
- 125000004414 alkyl thio group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 23
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 16
- 208000035143 Bacterial infection Diseases 0.000 claims description 15
- 208000010362 Protozoan Infections Diseases 0.000 claims description 15
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 15
- 241000124008 Mammalia Species 0.000 claims description 14
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 241000251468 Actinopterygii Species 0.000 claims description 13
- 238000012545 processing Methods 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 9
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 6
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 claims description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical group [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 claims description 3
- 230000010933 acylation Effects 0.000 claims description 3
- 238000005917 acylation reaction Methods 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 claims description 3
- OXBFBRZWBIXFGO-UHFFFAOYSA-N trichloro(isocyanato)methane Chemical compound ClC(Cl)(Cl)N=C=O OXBFBRZWBIXFGO-UHFFFAOYSA-N 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- OFHCOWSQAMBJIW-AVJTYSNKSA-N alfacalcidol Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)C[C@H](O)C1=C OFHCOWSQAMBJIW-AVJTYSNKSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 43
- 108010030975 Polyketide Synthases Proteins 0.000 description 41
- 238000011068 loading method Methods 0.000 description 38
- 229960003276 erythromycin Drugs 0.000 description 34
- 208000015181 infectious disease Diseases 0.000 description 34
- 108090000623 proteins and genes Proteins 0.000 description 31
- 239000000243 solution Substances 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000002585 base Substances 0.000 description 21
- 238000004519 manufacturing process Methods 0.000 description 21
- 239000011541 reaction mixture Substances 0.000 description 21
- 125000001589 carboacyl group Chemical group 0.000 description 20
- 229930001119 polyketide Natural products 0.000 description 20
- 239000003120 macrolide antibiotic agent Substances 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- 125000000830 polyketide group Chemical group 0.000 description 17
- 239000007787 solid Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 230000015572 biosynthetic process Effects 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- 239000007832 Na2SO4 Substances 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 230000001580 bacterial effect Effects 0.000 description 14
- 239000012267 brine Substances 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 14
- 239000000203 mixture Substances 0.000 description 13
- 238000003786 synthesis reaction Methods 0.000 description 13
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 11
- 210000004027 cell Anatomy 0.000 description 11
- 238000002474 experimental method Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 229960002626 clarithromycin Drugs 0.000 description 10
- 238000000855 fermentation Methods 0.000 description 10
- 230000004151 fermentation Effects 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- 108700016155 Acyl transferases Proteins 0.000 description 9
- 102000057234 Acyl transferases Human genes 0.000 description 9
- 241000283690 Bos taurus Species 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- 241000187559 Saccharopolyspora erythraea Species 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000013612 plasmid Substances 0.000 description 9
- 241000606856 Pasteurella multocida Species 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- 125000004122 cyclic group Chemical group 0.000 description 8
- 239000003999 initiator Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 241000271566 Aves Species 0.000 description 7
- 108020004414 DNA Proteins 0.000 description 7
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 7
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 7
- 229960002930 sirolimus Drugs 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229940088710 antibiotic agent Drugs 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 229940041033 macrolides Drugs 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 230000008569 process Effects 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000005660 Abamectin Substances 0.000 description 5
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 5
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 206010061218 Inflammation Diseases 0.000 description 5
- 241001293418 Mannheimia haemolytica Species 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- RRZXIRBKKLTSOM-XPNPUAGNSA-N avermectin B1a Chemical compound C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 RRZXIRBKKLTSOM-XPNPUAGNSA-N 0.000 description 5
- 230000001851 biosynthetic effect Effects 0.000 description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
- 150000001735 carboxylic acids Chemical class 0.000 description 5
- 235000019439 ethyl acetate Nutrition 0.000 description 5
- 230000004054 inflammatory process Effects 0.000 description 5
- 150000003881 polyketide derivatives Chemical class 0.000 description 5
- 230000007480 spreading Effects 0.000 description 5
- 238000003892 spreading Methods 0.000 description 5
- 101710146995 Acyl carrier protein Proteins 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000027455 binding Effects 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 210000000349 chromosome Anatomy 0.000 description 4
- 239000003085 diluting agent Substances 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- 230000011987 methylation Effects 0.000 description 4
- 238000007069 methylation reaction Methods 0.000 description 4
- 231100000252 nontoxic Toxicity 0.000 description 4
- 230000003000 nontoxic effect Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 238000003752 polymerase chain reaction Methods 0.000 description 4
- 238000012746 preparative thin layer chromatography Methods 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000193403 Clostridium Species 0.000 description 3
- 241000588724 Escherichia coli Species 0.000 description 3
- 108010010803 Gelatin Proteins 0.000 description 3
- 241000606768 Haemophilus influenzae Species 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 241000193996 Streptococcus pyogenes Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 238000013459 approach Methods 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 239000012458 free base Substances 0.000 description 3
- 229920000159 gelatin Polymers 0.000 description 3
- 235000019322 gelatine Nutrition 0.000 description 3
- 235000011852 gelatine desserts Nutrition 0.000 description 3
- 238000006206 glycosylation reaction Methods 0.000 description 3
- 238000005805 hydroxylation reaction Methods 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 125000006239 protecting group Chemical group 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 230000008261 resistance mechanism Effects 0.000 description 3
- 238000013207 serial dilution Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- HQZOLNNEQAKEHT-UHFFFAOYSA-N (3R,4S,5R,6S,7S,9R,11R,12S,13R,14R)-14-ethyl-4,6,12-trihydroxy-3,5,7,9,11,13-hexamethyloxacyclotetradecane-2,10-dione Natural products CCC1OC(=O)C(C)C(O)C(C)C(O)C(C)CC(C)C(=O)C(C)C(O)C1C HQZOLNNEQAKEHT-UHFFFAOYSA-N 0.000 description 2
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- VTIKDEXOEJDMJP-UHFFFAOYSA-N Actinorhodine Natural products CC1OC(CC(=O)O)CC2=C1C(=O)c3c(O)c(cc(O)c3C2=O)c4cc(O)c5C(=O)C6=C(C(C)OC(CC(=O)O)C6)C(=O)c5c4O VTIKDEXOEJDMJP-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 201000001320 Atherosclerosis Diseases 0.000 description 2
- 241001148536 Bacteroides sp. Species 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 2
- 241001647372 Chlamydia pneumoniae Species 0.000 description 2
- 241000606153 Chlamydia trachomatis Species 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- 108010065152 Coagulase Proteins 0.000 description 2
- 108091026890 Coding region Proteins 0.000 description 2
- 241000194033 Enterococcus Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- 241000590002 Helicobacter pylori Species 0.000 description 2
- 241000282412 Homo Species 0.000 description 2
- YKFRUJSEPGHZFJ-UHFFFAOYSA-N N-trimethylsilylimidazole Chemical compound C[Si](C)(C)N1C=CN=C1 YKFRUJSEPGHZFJ-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 108700026244 Open Reading Frames Proteins 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 241000191992 Peptostreptococcus Species 0.000 description 2
- 229920000954 Polyglycolide Polymers 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000193998 Streptococcus pneumoniae Species 0.000 description 2
- 241000187432 Streptomyces coelicolor Species 0.000 description 2
- 101000691656 Streptomyces venezuelae Narbonolide/10-deoxymethynolide synthase PikA1, modules 1 and 2 Proteins 0.000 description 2
- 101000691655 Streptomyces venezuelae Narbonolide/10-deoxymethynolide synthase PikA2, modules 3 and 4 Proteins 0.000 description 2
- 101000691658 Streptomyces venezuelae Narbonolide/10-deoxymethynolide synthase PikA3, module 5 Proteins 0.000 description 2
- 101001125873 Streptomyces venezuelae Narbonolide/10-deoxymethynolide synthase PikA4, module 6 Proteins 0.000 description 2
- 241000282887 Suidae Species 0.000 description 2
- QJJXYPPXXYFBGM-LFZNUXCKSA-N Tacrolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1\C=C(/C)[C@@H]1[C@H](C)[C@@H](O)CC(=O)[C@H](CC=C)/C=C(C)/C[C@H](C)C[C@H](OC)[C@H]([C@H](C[C@H]2C)OC)O[C@@]2(O)C(=O)C(=O)N2CCCC[C@H]2C(=O)O1 QJJXYPPXXYFBGM-LFZNUXCKSA-N 0.000 description 2
- 208000025865 Ulcer Diseases 0.000 description 2
- VTIKDEXOEJDMJP-WYUUTHIRSA-N actinorhodin Chemical compound C([C@@H](CC(O)=O)O[C@@H]1C)C(C(C2=C(O)C=3)=O)=C1C(=O)C2=C(O)C=3C(C(=C1C2=O)O)=CC(O)=C1C(=O)C1=C2[C@@H](C)O[C@H](CC(O)=O)C1 VTIKDEXOEJDMJP-WYUUTHIRSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001413 amino acids Chemical class 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 238000011203 antimicrobial therapy Methods 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000002393 azetidinyl group Chemical group 0.000 description 2
- 229960004099 azithromycin Drugs 0.000 description 2
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229940038705 chlamydia trachomatis Drugs 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 235000019867 fractionated palm kernal oil Nutrition 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 238000010353 genetic engineering Methods 0.000 description 2
- 230000012010 growth Effects 0.000 description 2
- 229940047650 haemophilus influenzae Drugs 0.000 description 2
- 229940037467 helicobacter pylori Drugs 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002458 infectious effect Effects 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 208000028774 intestinal disease Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 238000012544 monitoring process Methods 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 0.000 description 2
- 239000002674 ointment Substances 0.000 description 2
- 230000008520 organization Effects 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 230000037361 pathway Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229920000747 poly(lactic acid) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 2
- 230000002829 reductive effect Effects 0.000 description 2
- 208000023504 respiratory system disease Diseases 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000002356 single layer Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004354 sulfur functional group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- QJJXYPPXXYFBGM-SHYZHZOCSA-N tacrolimus Natural products CO[C@H]1C[C@H](CC[C@@H]1O)C=C(C)[C@H]2OC(=O)[C@H]3CCCCN3C(=O)C(=O)[C@@]4(O)O[C@@H]([C@H](C[C@H]4C)OC)[C@@H](C[C@H](C)CC(=C[C@@H](CC=C)C(=O)C[C@H](O)[C@H]2C)C)OC QJJXYPPXXYFBGM-SHYZHZOCSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000335 thiazolyl group Chemical group 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
- 238000013518 transcription Methods 0.000 description 2
- 230000035897 transcription Effects 0.000 description 2
- 231100000397 ulcer Toxicity 0.000 description 2
- 208000019206 urinary tract infection Diseases 0.000 description 2
- 239000013598 vector Substances 0.000 description 2
- XZJAKURZQBNKKX-QFQDJZPHSA-N (3e)-3-[(2s)-1-hydroxy-2-[(1s,2s,6r)-2-[(e)-3-hydroxy-2-[(2r,3r,6s)-6-[(e,3s)-3-[(2r,3s,5r)-5-[(1s)-1-methoxyethyl]-3-methyloxolan-2-yl]but-1-enyl]-3-methyloxan-2-yl]prop-1-enyl]-6-methylcyclohexyl]propylidene]oxolane-2,4-dione Chemical compound O1[C@@H]([C@H](C)OC)C[C@H](C)[C@@H]1[C@@H](C)\C=C\[C@H]1O[C@@H](C(\CO)=C\[C@@H]2[C@H]([C@H](C)CCC2)[C@H](C)C(\O)=C\2C(OCC/2=O)=O)[C@H](C)CC1 XZJAKURZQBNKKX-QFQDJZPHSA-N 0.000 description 1
- ZUGIGWIPEYNYJV-FZWPAWTOSA-N (3r,4s,5r,6s,7s,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradecane-2,10-dione Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ZUGIGWIPEYNYJV-FZWPAWTOSA-N 0.000 description 1
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 description 1
- IGERFAHWSHDDHX-UHFFFAOYSA-N 1,3-dioxanyl Chemical group [CH]1OCCCO1 IGERFAHWSHDDHX-UHFFFAOYSA-N 0.000 description 1
- GRNOZCCBOFGDCL-UHFFFAOYSA-N 2,2,2-trichloroacetyl isocyanate Chemical compound ClC(Cl)(Cl)C(=O)N=C=O GRNOZCCBOFGDCL-UHFFFAOYSA-N 0.000 description 1
- WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical compound OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
- WLAMNBDJUVNPJU-UHFFFAOYSA-M 2-methylbutyrate Chemical compound CCC(C)C([O-])=O WLAMNBDJUVNPJU-UHFFFAOYSA-M 0.000 description 1
- 125000001698 2H-pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-M 3-carboxy-2,3-dihydroxypropanoate Chemical compound OC(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-M 0.000 description 1
- 125000004364 3-pyrrolinyl group Chemical group [H]C1=C([H])C([H])([H])N(*)C1([H])[H] 0.000 description 1
- SAHOBIBQRTZUGB-UHFFFAOYSA-N 3-quinolin-4-ylpropanal Chemical compound C1=CC=C2C(CCC=O)=CC=NC2=C1 SAHOBIBQRTZUGB-UHFFFAOYSA-N 0.000 description 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 description 1
- PZFFSGZBQUSNGT-UHFFFAOYSA-N 4-(4-pyridin-3-ylimidazol-1-yl)butan-1-amine Chemical compound NCCCCN1C=NC(C=2C=NC=CC=2)=C1 PZFFSGZBQUSNGT-UHFFFAOYSA-N 0.000 description 1
- 125000001826 4H-pyranyl group Chemical group O1C(=CCC=C1)* 0.000 description 1
- AKHSBAVQPIRVAG-UHFFFAOYSA-N 4h-isochromene-1,3-dione Chemical compound C1=CC=C2C(=O)OC(=O)CC2=C1 AKHSBAVQPIRVAG-UHFFFAOYSA-N 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- HQZOLNNEQAKEHT-IBBGRPSASA-N 6-deoxyerythronolide B Chemical compound CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@@H](C)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C HQZOLNNEQAKEHT-IBBGRPSASA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 241000606750 Actinobacillus Species 0.000 description 1
- 241000186361 Actinobacteria <class> Species 0.000 description 1
- 108700037654 Acyl carrier protein (ACP) Proteins 0.000 description 1
- 102000048456 Acyl carrier protein (ACP) Human genes 0.000 description 1
- 241000588986 Alcaligenes Species 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 229930183010 Amphotericin Natural products 0.000 description 1
- QGGFZZLFKABGNL-UHFFFAOYSA-N Amphotericin A Natural products OC1C(N)C(O)C(C)OC1OC1C=CC=CC=CC=CCCC=CC=CC(C)C(O)C(C)C(C)OC(=O)CC(O)CC(O)CCC(O)C(O)CC(O)CC(O)(CC(O)C2C(O)=O)OC2C1 QGGFZZLFKABGNL-UHFFFAOYSA-N 0.000 description 1
- 241000606660 Bartonella Species 0.000 description 1
- 241000588807 Bordetella Species 0.000 description 1
- 241000588832 Bordetella pertussis Species 0.000 description 1
- 241001148534 Brachyspira Species 0.000 description 1
- 101100129922 Caenorhabditis elegans pig-1 gene Proteins 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000193468 Clostridium perfringens Species 0.000 description 1
- 241000224483 Coccidia Species 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- 241000186216 Corynebacterium Species 0.000 description 1
- 206010011224 Cough Diseases 0.000 description 1
- 241000223935 Cryptosporidium Species 0.000 description 1
- VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
- NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 description 1
- DSLZVSRJTYRBFB-LLEIAEIESA-N D-glucaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O DSLZVSRJTYRBFB-LLEIAEIESA-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
- 102000052510 DNA-Binding Proteins Human genes 0.000 description 1
- 108700020911 DNA-Binding Proteins Proteins 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 241000605721 Dichelobacter nodosus Species 0.000 description 1
- 101100520057 Drosophila melanogaster Pig1 gene Proteins 0.000 description 1
- 241000588914 Enterobacter Species 0.000 description 1
- 229930006677 Erythromycin A Natural products 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 241000186394 Eubacterium Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 206010016952 Food poisoning Diseases 0.000 description 1
- 208000019331 Foodborne disease Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 1
- 241000605909 Fusobacterium Species 0.000 description 1
- 241000605952 Fusobacterium necrophorum Species 0.000 description 1
- 230000005526 G1 to G0 transition Effects 0.000 description 1
- 201000000628 Gas Gangrene Diseases 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- 229910004373 HOAc Inorganic materials 0.000 description 1
- 239000004705 High-molecular-weight polyethylene Substances 0.000 description 1
- 101000833492 Homo sapiens Jouberin Proteins 0.000 description 1
- 101000651236 Homo sapiens NCK-interacting protein with SH3 domain Proteins 0.000 description 1
- 101000601394 Homo sapiens Neuroendocrine convertase 2 Proteins 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 102100024407 Jouberin Human genes 0.000 description 1
- 101150076577 KPS gene Proteins 0.000 description 1
- 241000588748 Klebsiella Species 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
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 241001148567 Lawsonia intracellularis Species 0.000 description 1
- 241000589242 Legionella pneumophila Species 0.000 description 1
- 101001110310 Lentilactobacillus kefiri NADP-dependent (R)-specific alcohol dehydrogenase Proteins 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 241000186781 Listeria Species 0.000 description 1
- 208000016604 Lyme disease Diseases 0.000 description 1
- 101150052154 MSRA1 gene Proteins 0.000 description 1
- 240000003183 Manihot esculenta Species 0.000 description 1
- 235000016735 Manihot esculenta subsp esculenta Nutrition 0.000 description 1
- 208000010315 Mastoiditis Diseases 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 229920000168 Microcrystalline cellulose Polymers 0.000 description 1
- 241000187723 Micromonospora sp. Species 0.000 description 1
- 101001014220 Monascus pilosus Dehydrogenase mokE Proteins 0.000 description 1
- 229930191564 Monensin Natural products 0.000 description 1
- GAOZTHIDHYLHMS-UHFFFAOYSA-N Monensin A Natural products O1C(CC)(C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CCC1C(O1)(C)CCC21CC(O)C(C)C(C(C)C(OC)C(C)C(O)=O)O2 GAOZTHIDHYLHMS-UHFFFAOYSA-N 0.000 description 1
- 241000588621 Moraxella Species 0.000 description 1
- 241000588622 Moraxella bovis Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000186364 Mycobacterium intracellulare Species 0.000 description 1
- 241000204031 Mycoplasma Species 0.000 description 1
- 241001138504 Mycoplasma bovis Species 0.000 description 1
- 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
- 229910017852 NH2NH2 Inorganic materials 0.000 description 1
- 229910017912 NH2OH Inorganic materials 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- 241000588653 Neisseria Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 102100037732 Neuroendocrine convertase 2 Human genes 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 241000187681 Nocardia sp. Species 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 1
- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 description 1
- 239000004104 Oleandomycin Substances 0.000 description 1
- 206010048685 Oral infection Diseases 0.000 description 1
- 206010068319 Oropharyngeal pain Diseases 0.000 description 1
- 206010031149 Osteitis Diseases 0.000 description 1
- 206010033078 Otitis media Diseases 0.000 description 1
- 241000606860 Pasteurella Species 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 101000573542 Penicillium citrinum Compactin nonaketide synthase, enoyl reductase component Proteins 0.000 description 1
- 201000007100 Pharyngitis Diseases 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- 208000005374 Poisoning Diseases 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920001710 Polyorthoester Polymers 0.000 description 1
- 241000605894 Porphyromonas Species 0.000 description 1
- 241000605861 Prevotella Species 0.000 description 1
- 102000055027 Protein Methyltransferases Human genes 0.000 description 1
- 108700040121 Protein Methyltransferases Proteins 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- 206010057190 Respiratory tract infections Diseases 0.000 description 1
- 229930189077 Rifamycin Natural products 0.000 description 1
- 241000187560 Saccharopolyspora Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- 238000012300 Sequence Analysis Methods 0.000 description 1
- 208000019802 Sexually transmitted disease Diseases 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 206010062255 Soft tissue infection Diseases 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 241000194017 Streptococcus Species 0.000 description 1
- 241000193985 Streptococcus agalactiae Species 0.000 description 1
- 241001312524 Streptococcus viridans Species 0.000 description 1
- 108010015795 Streptogramin B Proteins 0.000 description 1
- 108010034396 Streptogramins Proteins 0.000 description 1
- 241000187747 Streptomyces Species 0.000 description 1
- 241000186988 Streptomyces antibioticus Species 0.000 description 1
- 241001468227 Streptomyces avermitilis Species 0.000 description 1
- 241000936710 Streptomyces griseoplanus Species 0.000 description 1
- 241000187391 Streptomyces hygroscopicus Species 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
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 239000004098 Tetracycline Substances 0.000 description 1
- 206010044248 Toxic shock syndrome Diseases 0.000 description 1
- 231100000650 Toxic shock syndrome Toxicity 0.000 description 1
- 241000589884 Treponema pallidum Species 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 241000202921 Ureaplasma urealyticum Species 0.000 description 1
- 208000018079 Uterine Cervical disease Diseases 0.000 description 1
- 241000606834 [Haemophilus] ducreyi Species 0.000 description 1
- 206010000210 abortion Diseases 0.000 description 1
- 231100000176 abortion Toxicity 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 229940009444 amphotericin Drugs 0.000 description 1
- APKFDSVGJQXUKY-INPOYWNPSA-N amphotericin B Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 APKFDSVGJQXUKY-INPOYWNPSA-N 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 229940124339 anthelmintic agent Drugs 0.000 description 1
- 239000000921 anthelmintic agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940121375 antifungal agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000003904 antiprotozoal agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- ZDQSOHOQTUFQEM-PKUCKEGBSA-N ascomycin Chemical compound C/C([C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@]2(O)O[C@@H]([C@H](C[C@H]2C)OC)[C@@H](OC)C[C@@H](C)C\C(C)=C/[C@H](C(C[C@H](O)[C@H]1C)=O)CC)=C\[C@@H]1CC[C@@H](O)[C@H](OC)C1 ZDQSOHOQTUFQEM-PKUCKEGBSA-N 0.000 description 1
- ZDQSOHOQTUFQEM-XCXYXIJFSA-N ascomycin Natural products CC[C@H]1C=C(C)C[C@@H](C)C[C@@H](OC)[C@H]2O[C@@](O)([C@@H](C)C[C@H]2OC)C(=O)C(=O)N3CCCC[C@@H]3C(=O)O[C@H]([C@H](C)[C@@H](O)CC1=O)C(=C[C@@H]4CC[C@@H](O)[C@H](C4)OC)C ZDQSOHOQTUFQEM-XCXYXIJFSA-N 0.000 description 1
- 229940072107 ascorbate Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 229940090047 auto-injector Drugs 0.000 description 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229940077388 benzenesulfonate Drugs 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004601 benzofurazanyl group Chemical group N1=C2C(=NO1)C(=CC=C2)* 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 230000002457 bidirectional effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229920002988 biodegradable polymer Polymers 0.000 description 1
- 239000004621 biodegradable polymer Substances 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229960003563 calcium carbonate Drugs 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000007942 carboxylates Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 210000003679 cervix uteri Anatomy 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 208000013116 chronic cough Diseases 0.000 description 1
- 229940001468 citrate Drugs 0.000 description 1
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical group O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000013267 controlled drug release Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 210000004087 cornea Anatomy 0.000 description 1
- 201000010251 cutis laxa Diseases 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 1
- FNFJZXAWCAEGNI-UHFFFAOYSA-N cycloheptene-1-carboxylic acid Chemical compound OC(=O)C1=CCCCCC1 FNFJZXAWCAEGNI-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- JBDSSBMEKXHSJF-UHFFFAOYSA-N cyclopentanecarboxylic acid Chemical compound OC(=O)C1CCCC1 JBDSSBMEKXHSJF-UHFFFAOYSA-N 0.000 description 1
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 238000003386 deoximation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 229940039227 diagnostic agent Drugs 0.000 description 1
- 239000000032 diagnostic agent Substances 0.000 description 1
- 125000002576 diazepinyl group Chemical group N1N=C(C=CC=C1)* 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 125000004852 dihydrofuranyl group Chemical group O1C(CC=C1)* 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 125000005057 dihydrothienyl group Chemical group S1C(CC=C1)* 0.000 description 1
- 125000000532 dioxanyl group Chemical group 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 125000005883 dithianyl group Chemical group 0.000 description 1
- 125000005411 dithiolanyl group Chemical group S1SC(CC1)* 0.000 description 1
- QZUNHWGQSGFRAR-UHFFFAOYSA-N dodecyl octadecanoate;sodium Chemical compound [Na].CCCCCCCCCCCCCCCCCC(=O)OCCCCCCCCCCCC QZUNHWGQSGFRAR-UHFFFAOYSA-N 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 230000002357 endometrial effect Effects 0.000 description 1
- 238000006735 epoxidation reaction Methods 0.000 description 1
- 101150106583 ermBC gene Proteins 0.000 description 1
- 101150016744 ermC gene Proteins 0.000 description 1
- ZFBRGCCVTUPRFQ-HWRKYNCUSA-N erythronolide B Chemical class CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@H]1C ZFBRGCCVTUPRFQ-HWRKYNCUSA-N 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 125000003838 furazanyl group Chemical group 0.000 description 1
- 125000004612 furopyridinyl group Chemical group O1C(=CC2=C1C=CC=N2)* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000030135 gastric motility Effects 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 108091008053 gene clusters Proteins 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 229940050410 gluconate Drugs 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229960002449 glycine Drugs 0.000 description 1
- 230000013595 glycosylation Effects 0.000 description 1
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical class OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000006801 homologous recombination Effects 0.000 description 1
- 238000002744 homologous recombination Methods 0.000 description 1
- 210000000003 hoof Anatomy 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 239000000017 hydrogel Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 230000033444 hydroxylation Effects 0.000 description 1
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002632 imidazolidinyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 230000001506 immunosuppresive effect Effects 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 239000003018 immunosuppressive agent Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 description 1
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 description 1
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000010354 integration Effects 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000002555 ionophore Substances 0.000 description 1
- 230000000236 ionophoric effect Effects 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 206010023332 keratitis Diseases 0.000 description 1
- 239000003835 ketolide antibiotic agent Substances 0.000 description 1
- 208000017169 kidney disease Diseases 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 229940115932 legionella pneumophila Drugs 0.000 description 1
- 229940041028 lincosamides Drugs 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 229930013918 macrolide polyketide Natural products 0.000 description 1
- 125000000585 macrolide polyketide group Chemical group 0.000 description 1
- 235000019359 magnesium stearate Nutrition 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
- 208000004396 mastitis Diseases 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 101150111763 mefA gene Proteins 0.000 description 1
- 230000004060 metabolic process Effects 0.000 description 1
- 150000003956 methylamines Chemical class 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000003032 molecular docking Methods 0.000 description 1
- 229960005358 monensin Drugs 0.000 description 1
- GAOZTHIDHYLHMS-KEOBGNEYSA-N monensin A Chemical compound C([C@@](O1)(C)[C@H]2CC[C@@](O2)(CC)[C@H]2[C@H](C[C@@H](O2)[C@@H]2[C@H](C[C@@H](C)[C@](O)(CO)O2)C)C)C[C@@]21C[C@H](O)[C@@H](C)[C@@H]([C@@H](C)[C@@H](OC)[C@H](C)C(O)=O)O2 GAOZTHIDHYLHMS-KEOBGNEYSA-N 0.000 description 1
- 101150021123 msrA gene Proteins 0.000 description 1
- 101150114366 msrA2 gene Proteins 0.000 description 1
- 101150006794 msrAB gene Proteins 0.000 description 1
- 101150109310 msrAB1 gene Proteins 0.000 description 1
- 101150052209 msrAB2 gene Proteins 0.000 description 1
- 229940013390 mycoplasma pneumoniae Drugs 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 229960002351 oleandomycin Drugs 0.000 description 1
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 description 1
- 235000019367 oleandomycin Nutrition 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000008203 oral pharmaceutical composition Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000003551 oxepanyl group Chemical group 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 238000006146 oximation reaction Methods 0.000 description 1
- 125000004043 oxo group Chemical group O=* 0.000 description 1
- 125000001312 palmitoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940014662 pantothenate Drugs 0.000 description 1
- 235000019161 pantothenic acid Nutrition 0.000 description 1
- 239000011713 pantothenic acid Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000010603 pastilles Nutrition 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000026731 phosphorylation Effects 0.000 description 1
- 238000006366 phosphorylation reaction Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 239000013600 plasmid vector Substances 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001610 polycaprolactone Polymers 0.000 description 1
- 229920002721 polycyanoacrylate Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004633 polyglycolic acid Substances 0.000 description 1
- 239000004626 polylactic acid Substances 0.000 description 1
- 229920000656 polylysine Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- YGXCETJZBDTKRY-DZCVGBHJSA-N pristinamycin IA Chemical compound N([C@@H]1C(=O)N[C@@H](C(N2CCC[C@H]2C(=O)N(C)[C@@H](CC=2C=CC(=CC=2)N(C)C)C(=O)N2CCC(=O)C[C@H]2C(=O)N[C@H](C(=O)O[C@@H]1C)C=1C=CC=CC=1)=O)CC)C(=O)C1=NC=CC=C1O YGXCETJZBDTKRY-DZCVGBHJSA-N 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 208000028172 protozoa infectious disease Diseases 0.000 description 1
- 244000079416 protozoan pathogen Species 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000009790 rate-determining step (RDS) Methods 0.000 description 1
- 238000005932 reductive alkylation reaction Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 208000007865 relapsing fever Diseases 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 208000020029 respiratory tract infectious disease Diseases 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 201000003068 rheumatic fever Diseases 0.000 description 1
- 229960003292 rifamycin Drugs 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000012163 sequencing technique Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 206010040872 skin infection Diseases 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 229960001790 sodium citrate Drugs 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical class [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- YVOFSHPIJOYKSH-NLYBMVFSSA-M sodium rifomycin sv Chemical compound [Na+].OC1=C(C(O)=C2C)C3=C([O-])C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O YVOFSHPIJOYKSH-NLYBMVFSSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000006467 substitution reaction Methods 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
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 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
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 229950002881 tetronasin Drugs 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000005308 thiazepinyl group Chemical group S1N=C(C=CC=C1)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001583 thiepanyl group Chemical group 0.000 description 1
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 206010044008 tonsillitis Diseases 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 108091005703 transmembrane proteins Proteins 0.000 description 1
- 102000035160 transmembrane proteins Human genes 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 241001446247 uncultured actinomycete Species 0.000 description 1
- 210000001635 urinary tract Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- 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
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Veterinary Medicine (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US7035898P | 1998-01-02 | 1998-01-02 | |
| PCT/IB1998/002100 WO1999035157A1 (en) | 1998-01-02 | 1998-12-21 | Novel erythromycin derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20000444A2 true HRP20000444A2 (en) | 2001-04-30 |
Family
ID=22094819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20000444A HRP20000444A2 (en) | 1998-01-02 | 2000-06-30 | Novel erythromycin derivatives |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US6825171B2 (sk) |
| EP (2) | EP1044208A1 (sk) |
| JP (1) | JP2002500231A (sk) |
| KR (1) | KR20010033822A (sk) |
| CN (1) | CN1285841A (sk) |
| AP (1) | AP1060A (sk) |
| AR (5) | AR012764A1 (sk) |
| AT (1) | ATE377018T1 (sk) |
| AU (1) | AU759019B2 (sk) |
| BG (1) | BG104640A (sk) |
| BR (1) | BR9812992A (sk) |
| CA (1) | CA2317131C (sk) |
| CO (1) | CO4970773A1 (sk) |
| CZ (1) | CZ20002456A3 (sk) |
| DE (1) | DE69838651T9 (sk) |
| DZ (1) | DZ2699A1 (sk) |
| EA (1) | EA200000600A1 (sk) |
| ES (1) | ES2294641T3 (sk) |
| GT (1) | GT199800207A (sk) |
| HR (1) | HRP20000444A2 (sk) |
| HU (1) | HUP0100566A3 (sk) |
| IL (1) | IL136721A0 (sk) |
| IS (1) | IS5527A (sk) |
| MA (1) | MA26588A1 (sk) |
| NO (1) | NO20003346L (sk) |
| NZ (1) | NZ504987A (sk) |
| OA (1) | OA11440A (sk) |
| PA (1) | PA8465901A1 (sk) |
| PE (1) | PE20000119A1 (sk) |
| PL (1) | PL341647A1 (sk) |
| SK (1) | SK9772000A3 (sk) |
| TN (1) | TNSN98236A1 (sk) |
| UY (2) | UY25331A1 (sk) |
| WO (1) | WO1999035157A1 (sk) |
| YU (1) | YU40900A (sk) |
| ZA (1) | ZA9811940B (sk) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AP9801420A0 (en) | 1998-01-02 | 1998-12-31 | Pfizer Prod Inc | Novel macrolides. |
| AP1060A (en) | 1998-01-02 | 2002-04-23 | Pfizer Prod Inc | Novel erythromycin derivatives. |
| GB9814006D0 (en) * | 1998-06-29 | 1998-08-26 | Biotica Tech Ltd | Polyketides and their synthesis |
| EP1749832A3 (en) * | 1998-12-10 | 2008-03-26 | Pfizer Products Incorporated | Carbamate and carbazate ketolide antibiotics |
| EP1298138B1 (en) * | 1998-12-10 | 2006-11-02 | Pfizer Products Inc. | Carbamate and Carbazate Ketolide Antibiotics |
| EP1137654A1 (en) | 1998-12-10 | 2001-10-04 | Pfizer Products Inc. | Carbamate and carbazate ketolide antibiotics |
| OA11753A (en) | 1999-01-27 | 2005-07-19 | Pfizer Prod Inc | Ketolide antibiotics. |
| EP1754700A3 (en) | 1999-01-27 | 2007-05-09 | Kosan Biosciences, Inc. | Synthesis of oligoketides |
| US6451768B1 (en) | 1999-04-16 | 2002-09-17 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| DE60030847T2 (de) * | 1999-04-16 | 2007-04-19 | Kosan Biosciences, Inc., Hayward | Antiinfektiöse makrolidderivate |
| JP2002542197A (ja) | 1999-04-16 | 2002-12-10 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | ケトライド抗菌剤 |
| US6514944B2 (en) | 1999-04-16 | 2003-02-04 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| US6590083B1 (en) * | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| US6939861B2 (en) | 1999-04-16 | 2005-09-06 | Kosan Biosciences, Inc. | Amido macrolides |
| AP2001002302A0 (en) * | 1999-05-24 | 2001-10-25 | Pfizer Prod Inc | 13-Methyl erythromycin derivatives. |
| ID27331A (id) * | 1999-09-29 | 2001-03-29 | Pfizer Prod Inc | Pembuatan antibiotik-antibiotik ketolida karbamat |
| EP1114826A3 (en) * | 1999-12-29 | 2001-10-31 | Pfizer Products Inc. | Novel antibacterial and prokinetic macrolides |
| WO2001060833A2 (en) | 2000-02-18 | 2001-08-23 | Kosan Biosciences, Inc. | Motilide compounds |
| US20020115621A1 (en) | 2000-08-07 | 2002-08-22 | Wei-Gu Su | Macrolide antibiotics |
| US6472372B1 (en) | 2000-12-06 | 2002-10-29 | Ortho-Mcneil Pharmaceuticals, Inc. | 6-O-Carbamoyl ketolide antibacterials |
| AU2002316550A1 (en) | 2001-07-03 | 2003-01-21 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
| CA2460947A1 (en) | 2001-09-17 | 2003-03-27 | Ortho-Mcneil Pharmaceutical, Inc. | 6-o-carbamate-11,12-lacto-ketolide antimicrobials |
| WO2003050132A1 (en) | 2001-12-05 | 2003-06-19 | Ortho-Mcneil Pharmaceutical, Inc. | 6-o-acyl ketolide derivatives of erythromycine useful as antibacterials |
| WO2003102010A1 (en) | 2002-05-31 | 2003-12-11 | Janssen Pharmaceutica N.V. | 3-descladinosyl-6-o-carbamoyl and 6-o-carbonoyl macrolide antibacterial agents |
| WO2004096823A2 (en) | 2003-04-25 | 2004-11-11 | Chiron Corporation | Novel ketolide derivatives |
| UA85937C2 (uk) | 2004-12-21 | 2009-03-10 | Пфайзер Продактс Інк. | Макроліди |
| JP2009539970A (ja) | 2006-06-12 | 2009-11-19 | ラモット アット テル−アビブ ユニバーシティー リミテッド | 癌の治療方法 |
| US10987370B2 (en) | 2012-12-24 | 2021-04-27 | Ramot At Tel-Aviv University Ltd. | Methods of inducing read-through of a nonsense mutation associated with ataxia telangiectasia, Rett syndrome or spinal muscular atrophy by erythromycin or azithromycin |
Family Cites Families (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US61857A (en) * | 1867-02-05 | Improvement in top-drivers or spinners | ||
| US77302A (en) * | 1868-04-28 | mat son | ||
| US61856A (en) * | 1867-02-05 | Enos s | ||
| US100518A (en) * | 1870-03-08 | Roland s | ||
| US156027A (en) * | 1874-10-20 | Improvement in loom-shuttles | ||
| US4331803A (en) * | 1980-06-04 | 1982-05-25 | Taisho Pharmaceutical Co., Ltd. | Novel erythromycin compounds |
| SI8110592A8 (en) | 1981-03-06 | 1996-06-30 | Pliva Pharm & Chem Works | Process for preparing of n-methyl-11-aza-10-deoxo-10-dihydroerythromycine a and derivatives thereof |
| AU1142383A (en) | 1982-04-26 | 1983-11-03 | Shakas, P.V. | Infant transitional sensory system |
| US4474768A (en) | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| US4998097A (en) | 1983-07-11 | 1991-03-05 | Square D Company | Mechanically operated pressure switch having solid state components |
| JPS61103890A (ja) * | 1984-10-26 | 1986-05-22 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシンａ誘導体 |
| US4585759A (en) * | 1985-01-22 | 1986-04-29 | Pfizer Inc. | Antibacterial derivatives of a neutral macrolide |
| JPS61229895A (ja) * | 1985-04-03 | 1986-10-14 | Nippon Zeon Co Ltd | 保護化デス−ｎ−メチルエリスロマイシン誘導体 |
| ES8800986A1 (es) | 1985-07-27 | 1987-12-01 | Pfizer | Un procedimiento para la produccion de un nuevo derivado de avermectina |
| US4672056A (en) * | 1985-11-12 | 1987-06-09 | Abbott Laboratories | Erythromycin A derivatives and method of use |
| JPH0633312B2 (ja) | 1986-05-02 | 1994-05-02 | 大正製薬株式会社 | １４−ハイドロキシエリスロマイシン誘導体およびその製造方法 |
| DE3860503D1 (de) * | 1987-09-03 | 1990-10-04 | Pliva Pharm & Chem Works | 10-dihydro-10-deoxo-11-azaerythronolid-a-verbindungen,verfahren und zwischenprodukte zu ihrer herstellung und ihre verwendung in arzneimitteln und in deren herstellung. |
| GB8726730D0 (en) | 1987-11-14 | 1987-12-16 | Pfizer Ltd | Antiparasitic agents |
| GB8815967D0 (en) | 1988-07-05 | 1988-08-10 | Pfizer Ltd | Antiparasitic agents |
| US4934897A (en) | 1989-02-23 | 1990-06-19 | J. I. Case Company | Pipe-moving apparatus |
| US5141926A (en) | 1990-04-18 | 1992-08-25 | Abbott Laboratories | Erythromycin derivatives |
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
| WO1993013663A1 (en) | 1992-01-17 | 1993-07-22 | Abbott Laboratories | Method of directing biosynthesis of specific polyketides |
| US5824513A (en) * | 1991-01-17 | 1998-10-20 | Abbott Laboratories | Recombinant DNA method for producing erythromycin analogs |
| US6060234A (en) * | 1991-01-17 | 2000-05-09 | Abbott Laboratories | Polyketide derivatives and recombinant methods for making same |
| JP3286941B2 (ja) * | 1991-07-09 | 2002-05-27 | 株式会社日立製作所 | ダイヤモンド研削砥石のツルーイング法 |
| US5523399A (en) * | 1991-12-27 | 1996-06-04 | Taisho Pharmaceutical Co., Ltd. | 5-O-desosaminylerythronolide derivatives |
| FR2691464B1 (fr) | 1992-05-21 | 1995-06-02 | Roussel Uclaf | Nouveaux dérivés de la 1-oxa 6-azacyclopentadécane 13,15-dione, leur procédé de préparation et leur application comme médicaments. |
| FR2692579B1 (fr) * | 1992-06-19 | 1995-06-02 | Roussel Uclaf | Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments. |
| US5332807A (en) * | 1993-04-14 | 1994-07-26 | Merck & Co., Inc. | Process of producing 8A- and 9A-azalide antibiotics |
| US6066721A (en) * | 1995-07-06 | 2000-05-23 | Stanford University | Method to produce novel polyketides |
| US5441939A (en) * | 1994-03-04 | 1995-08-15 | Pfizer Inc. | 3"-desmethoxy derivatives of erythromycin and azithromycin |
| FR2718450B1 (fr) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5486697A (en) | 1994-11-14 | 1996-01-23 | California Institute Of Technology | Array of micro-machined mass energy micro-filters for charged particles |
| FR2732023B1 (fr) * | 1995-03-22 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2732684B1 (fr) * | 1995-04-06 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US5801032A (en) | 1995-08-03 | 1998-09-01 | Abbott Laboratories | Vectors and process for producing high purity 6,12-dideoxyerythromycin A by fermentation |
| WO1997008266A1 (en) | 1995-08-22 | 1997-03-06 | Mobil Oil Corporation | Visbreaking process using plastics as co-feed |
| IL123551A0 (en) | 1995-11-08 | 1998-10-30 | Abbott Lab | Tricyclic erythromycin derivatives |
| US6077943A (en) * | 1996-03-01 | 2000-06-20 | Takeda Chemical Industries, Ltd. | Method of producing erythromycin derivative |
| US5719272A (en) * | 1996-04-02 | 1998-02-17 | Abbott Laboratories | 2'-protected 3'-dimethylamine, 9-etheroxime erythromycin A derivatives |
| US5750510A (en) * | 1997-04-04 | 1998-05-12 | Abbott Laboratories | 3-descladinose-2,3-anhydroerythromycin derivatives |
| US6271255B1 (en) * | 1996-07-05 | 2001-08-07 | Biotica Technology Limited | Erythromycins and process for their preparation |
| WO1998001546A2 (en) | 1996-07-05 | 1998-01-15 | Biotica Technology Limited | Polyketides and their synthesis |
| PL188173B1 (pl) * | 1996-09-04 | 2004-12-31 | Abbott Lab | Pochodne erytromycyny, sposób wytwarzania pochodnych erytromycyny i środek o działaniu przeciwbakteryjnym |
| FR2754821B1 (fr) | 1996-10-23 | 2003-04-04 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| NL1006540C2 (nl) | 1997-07-10 | 1999-01-15 | Skf Ind Trading & Dev | Elektrische actuator met regelsensor, alsmede schijfrem omvattende een dergelijke actuator. |
| EP0899677B1 (en) | 1997-08-28 | 2006-03-15 | Supersensor (Proprietary) Limited | Reader arrangement for an electronic identification system |
| US6034069A (en) * | 1997-09-30 | 2000-03-07 | Abbott Laboratories | 3-'N-modified 6-O-substituted erythromycin ketolide derivatives having antibacterial activity |
| AP1060A (en) | 1998-01-02 | 2002-04-23 | Pfizer Prod Inc | Novel erythromycin derivatives. |
| AP9801420A0 (en) | 1998-01-02 | 1998-12-31 | Pfizer Prod Inc | Novel macrolides. |
| DK0941998T3 (da) * | 1998-03-03 | 2004-09-20 | Pfizer Prod Inc | 3,6-ketalmakrolidantibiotika |
| US5975370A (en) * | 1998-03-16 | 1999-11-02 | Owens-Illinois Closure Inc. | Tamper-evident plunger-hold-down attachment for pump dispenser |
| US6043227A (en) * | 1998-08-19 | 2000-03-28 | Pfizer Inc. | C11 carbamates of macrolide antibacterials |
| US6100240A (en) * | 1998-10-09 | 2000-08-08 | Pfizer Inc | Macrolide derivatives |
| US6262030B1 (en) * | 1998-11-03 | 2001-07-17 | Pfizer Inc. | Erythromycin derivatives |
| OA11753A (en) | 1999-01-27 | 2005-07-19 | Pfizer Prod Inc | Ketolide antibiotics. |
| EP1147224A1 (en) | 1999-02-05 | 2001-10-24 | WRAIR (Walter Reed Army Institute of Research) | Method of diagnosing of exposure to toxic agents by measuring distinct pattern in the levels of expression of specific genes |
| JP2002542197A (ja) * | 1999-04-16 | 2002-12-10 | オーソ−マクニール・フアーマシユーチカル・インコーポレーテツド | ケトライド抗菌剤 |
| DE60030847T2 (de) * | 1999-04-16 | 2007-04-19 | Kosan Biosciences, Inc., Hayward | Antiinfektiöse makrolidderivate |
| US20020061857A1 (en) | 1999-04-23 | 2002-05-23 | Yong-Jin Wu | 9-amino-3-oxo erythromycin derivatives |
| US20020077302A1 (en) | 1999-04-23 | 2002-06-20 | Yong-Jin Wu | Tricyclic erythromycin derivatives |
| AP2001002302A0 (en) | 1999-05-24 | 2001-10-25 | Pfizer Prod Inc | 13-Methyl erythromycin derivatives. |
| EP1101769A3 (en) * | 1999-11-18 | 2001-10-24 | Pfizer Products Inc. | Nitrogen containing erythromycin derivatives |
| US20020061856A1 (en) | 2000-04-24 | 2002-05-23 | Yong-Jin Wu | Novel tricyclic erythromycin derivatives |
| JP2005050903A (ja) | 2003-07-30 | 2005-02-24 | Toshiba Corp | 半導体装置およびその製造方法 |
-
1998
- 1998-12-17 AP APAP/P/1998/001421A patent/AP1060A/en active
- 1998-12-21 CZ CZ20002456A patent/CZ20002456A3/cs unknown
- 1998-12-21 KR KR1020007007378A patent/KR20010033822A/ko not_active Application Discontinuation
- 1998-12-21 EP EP98959099A patent/EP1044208A1/en not_active Withdrawn
- 1998-12-21 NZ NZ504987A patent/NZ504987A/xx unknown
- 1998-12-21 BR BR9812992-9A patent/BR9812992A/pt not_active Application Discontinuation
- 1998-12-21 CN CN98812832A patent/CN1285841A/zh active Pending
- 1998-12-21 WO PCT/IB1998/002100 patent/WO1999035157A1/en not_active Application Discontinuation
- 1998-12-21 HU HU0100566A patent/HUP0100566A3/hu unknown
- 1998-12-21 AT AT05106836T patent/ATE377018T1/de not_active IP Right Cessation
- 1998-12-21 DE DE69838651T patent/DE69838651T9/de not_active Expired - Fee Related
- 1998-12-21 IL IL13672198A patent/IL136721A0/xx unknown
- 1998-12-21 EA EA200000600A patent/EA200000600A1/ru unknown
- 1998-12-21 PL PL98341647A patent/PL341647A1/xx unknown
- 1998-12-21 EP EP05106836A patent/EP1642901B1/en not_active Expired - Lifetime
- 1998-12-21 ES ES05106836T patent/ES2294641T3/es not_active Expired - Lifetime
- 1998-12-21 YU YU40900A patent/YU40900A/sh unknown
- 1998-12-21 SK SK977-2000A patent/SK9772000A3/sk unknown
- 1998-12-21 AU AU15015/99A patent/AU759019B2/en not_active Ceased
- 1998-12-21 JP JP2000527553A patent/JP2002500231A/ja active Pending
- 1998-12-21 CA CA002317131A patent/CA2317131C/en not_active Expired - Fee Related
- 1998-12-28 PE PE1998001285A patent/PE20000119A1/es not_active Application Discontinuation
- 1998-12-29 AR ARP980106716A patent/AR012764A1/es not_active Application Discontinuation
- 1998-12-30 CO CO98077582A patent/CO4970773A1/es unknown
- 1998-12-30 DZ DZ980309A patent/DZ2699A1/xx active
- 1998-12-30 ZA ZA9811940A patent/ZA9811940B/xx unknown
- 1998-12-30 MA MA25408A patent/MA26588A1/fr unknown
- 1998-12-30 PA PA19988465901A patent/PA8465901A1/es unknown
- 1998-12-30 TN TNTNSN98236A patent/TNSN98236A1/fr unknown
- 1998-12-30 UY UY25331A patent/UY25331A1/es not_active Application Discontinuation
- 1998-12-30 GT GT199800207A patent/GT199800207A/es unknown
-
1999
- 1999-06-25 UY UY25587A patent/UY25587A1/es not_active Application Discontinuation
- 1999-11-30 AR ARP990106085A patent/AR020016A2/es not_active Application Discontinuation
- 1999-11-30 AR ARP990106083A patent/AR019789A2/es not_active Application Discontinuation
- 1999-11-30 AR ARP990106082A patent/AR019788A2/es not_active Application Discontinuation
- 1999-11-30 AR ARP990106084A patent/AR019790A2/es not_active Application Discontinuation
-
2000
- 2000-06-09 IS IS5527A patent/IS5527A/is unknown
- 2000-06-27 NO NO20003346A patent/NO20003346L/no unknown
- 2000-06-30 HR HR20000444A patent/HRP20000444A2/hr not_active Application Discontinuation
- 2000-06-30 OA OA1200000194A patent/OA11440A/en unknown
- 2000-07-27 BG BG104640A patent/BG104640A/xx unknown
-
2003
- 2003-04-08 US US10/409,016 patent/US6825171B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6825171B2 (en) | Erythromycin derivatives | |
| KR100352809B1 (ko) | 신규 매크롤라이드 | |
| US6777543B2 (en) | 13-methyl erythromycin derivatives | |
| CA2293335A1 (en) | 9-oxime erythromycin derivatives | |
| NO330249B1 (no) | Azalider samt anvendelser og fremstilling derav, og farmasøytiske sammensetninger | |
| EP0992509B1 (en) | Novel macrolide derivatives | |
| US6262030B1 (en) | Erythromycin derivatives | |
| HRP980248A2 (en) | Erythromycin derivatives | |
| MXPA00006602A (en) | Novel erythromycin derivatives | |
| MXPA00006604A (en) | Novel macrolides | |
| MXPA01010817A (en) | 13-methyl-erythromycin derivatives | |
| MXPA01002355A (en) | Ketolide antibiotics |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
| ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20021221 Year of fee payment: 5 |
|
| OBST | Application withdrawn |