OA11438A - Novel macrolides. - Google Patents

Novel macrolides. Download PDF

Info

Publication number: OA11438A
Authority: OA; OAPI
Prior art keywords: alkyl; groups; optionally; substituted; halo
Prior art date: 1998-01-02

Application number

OA1200000192A

Other languages

English (en)

Inventor

John Philip Dirlam

Hamish Alastair Irvin Mcarthur

Original Assignee

Pfizer Prod Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1998-01-02

Filing date

2000-06-30

Publication date

2004-04-30

2000-06-30 Application filed by Pfizer Prod Inc filed Critical Pfizer Prod Inc

2004-04-30 Publication of OA11438A publication Critical patent/OA11438A/en

Links

239000003120 macrolide antibiotic agent Substances 0.000 title description 27
229940041033 macrolides Drugs 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 134
208000015181 infectious disease Diseases 0.000 claims abstract description 54
238000000034 method Methods 0.000 claims abstract description 38
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims description 141
125000005843 halogen group Chemical group 0.000 claims description 98
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 75
229910052799 carbon Inorganic materials 0.000 claims description 62
125000003545 alkoxy group Chemical group 0.000 claims description 55
229920006395 saturated elastomer Polymers 0.000 claims description 53
125000000304 alkynyl group Chemical group 0.000 claims description 45
125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 44
229910052760 oxygen Inorganic materials 0.000 claims description 43
-1 oryl Chemical group 0.000 claims description 40
125000001424 substituent group Chemical group 0.000 claims description 38
125000003118 aryl group Chemical group 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 35
125000001072 heteroaryl group Chemical group 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 31
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 29
239000005864 Sulphur Substances 0.000 claims description 29
125000004093 cyano group Chemical group *C#N 0.000 claims description 29
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
239000001301 oxygen Substances 0.000 claims description 23
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
229910052717 sulfur Inorganic materials 0.000 claims description 20
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 19
238000004519 manufacturing process Methods 0.000 claims description 18
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
125000000623 heterocyclic group Chemical group 0.000 claims description 16
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 15
125000004372 methylthioethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])* 0.000 claims description 15
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 14
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 14
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 14
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims description 14
229910003446 platinum oxide Inorganic materials 0.000 claims description 14
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 13
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 12
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
125000004432 carbon atom Chemical group C* 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 10
SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims description 10
125000000392 cycloalkenyl group Chemical group 0.000 claims description 10
125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 9
241000251468 Actinopterygii Species 0.000 claims description 9
208000035143 Bacterial infection Diseases 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 9
208000022362 bacterial infectious disease Diseases 0.000 claims description 9
239000003638 chemical reducing agent Substances 0.000 claims description 9
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 8
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 8
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 8
125000004429 atom Chemical group 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
239000012022 methylating agents‎ Substances 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
239000003795 chemical substances by application Substances 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
239000012279 sodium borohydride Substances 0.000 claims description 7
229910000033 sodium borohydride Inorganic materials 0.000 claims description 7
125000004414 alkyl thio group Chemical group 0.000 claims description 6
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 6
239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
125000002971 oxazolyl group Chemical group 0.000 claims description 5
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 3
125000002950 monocyclic group Chemical group 0.000 claims description 3
125000003367 polycyclic group Chemical group 0.000 claims description 3
229910014585 C2-Ce Inorganic materials 0.000 claims description 2
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 3
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
125000006313 (C5-C8) alkyl group Chemical group 0.000 claims 1
125000002704 decyl group Chemical group [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])* 0.000 claims 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
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 abstract description 75
150000003839 salts Chemical class 0.000 abstract description 26
230000001580 bacterial effect Effects 0.000 abstract description 6
239000003242 anti bacterial agent Substances 0.000 abstract description 5
239000000543 intermediate Substances 0.000 abstract description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 132
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 60
239000000203 mixture Substances 0.000 description 55
229940073584 methylene chloride Drugs 0.000 description 44
239000000047 product Substances 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
238000006243 chemical reaction Methods 0.000 description 36
108090000623 proteins and genes Proteins 0.000 description 34
238000011068 loading method Methods 0.000 description 33
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
229960003276 erythromycin Drugs 0.000 description 30
239000000243 solution Substances 0.000 description 30
238000001914 filtration Methods 0.000 description 23
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 22
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
238000000746 purification Methods 0.000 description 20
239000012265 solid product Substances 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 19
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
239000002253 acid Substances 0.000 description 18
239000000706 filtrate Substances 0.000 description 18
150000002923 oximes Chemical class 0.000 description 18
239000002904 solvent Substances 0.000 description 18
229930001119 polyketide Natural products 0.000 description 17
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 16
239000007864 aqueous solution Substances 0.000 description 16
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 16
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 15
239000002585 base Substances 0.000 description 15
125000000830 polyketide group Chemical group 0.000 description 13
239000007858 starting material Substances 0.000 description 13
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
239000001257 hydrogen Substances 0.000 description 12
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 11
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 11
239000007832 Na2SO4 Substances 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
229910052938 sodium sulfate Inorganic materials 0.000 description 11
235000011152 sodium sulphate Nutrition 0.000 description 11
238000012360 testing method Methods 0.000 description 11
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000003556 assay Methods 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
241000193996 Streptococcus pyogenes Species 0.000 description 9
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
239000011734 sodium Substances 0.000 description 9
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 8
238000000855 fermentation Methods 0.000 description 8
230000004151 fermentation Effects 0.000 description 8
229940013688 formic acid Drugs 0.000 description 8
235000019253 formic acid Nutrition 0.000 description 8
239000013612 plasmid Substances 0.000 description 8
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 7
241000191967 Staphylococcus aureus Species 0.000 description 7
230000000694 effects Effects 0.000 description 7
CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 description 7
238000004128 high performance liquid chromatography Methods 0.000 description 7
239000003586 protic polar solvent Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
239000005660 Abamectin Substances 0.000 description 6
101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
102000004190 Enzymes Human genes 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
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 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
241000187559 Saccharopolyspora erythraea Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000012190 activator Substances 0.000 description 6
230000004075 alteration Effects 0.000 description 6
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 6
235000010633 broth Nutrition 0.000 description 6
210000004027 cell Anatomy 0.000 description 6
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
238000012545 processing Methods 0.000 description 6
229910052708 sodium Inorganic materials 0.000 description 6
239000000758 substrate Substances 0.000 description 6
241000606856 Pasteurella multocida Species 0.000 description 5
241000193998 Streptococcus pneumoniae Species 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000011575 calcium Substances 0.000 description 5
150000001768 cations Chemical class 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
125000002541 furyl group Chemical group 0.000 description 5
238000002955 isolation Methods 0.000 description 5
239000010410 layer Substances 0.000 description 5
238000004949 mass spectrometry Methods 0.000 description 5
230000007246 mechanism Effects 0.000 description 5
150000003881 polyketide derivatives Chemical class 0.000 description 5
230000002829 reductive effect Effects 0.000 description 5
229940031000 streptococcus pneumoniae Drugs 0.000 description 5
241000271566 Aves Species 0.000 description 4
241000193403 Clostridium Species 0.000 description 4
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
229930006677 Erythromycin A Natural products 0.000 description 4
241000588724 Escherichia coli Species 0.000 description 4
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
239000005977 Ethylene Substances 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241001293418 Mannheimia haemolytica Species 0.000 description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
230000001851 biosynthetic effect Effects 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
210000000349 chromosome Anatomy 0.000 description 4
125000004122 cyclic group Chemical group 0.000 description 4
239000012362 glacial acetic acid Substances 0.000 description 4
230000004048 modification Effects 0.000 description 4
238000012986 modification Methods 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
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 4
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 4
229960002930 sirolimus Drugs 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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 3
102000057234 Acyl transferases Human genes 0.000 description 3
108700016155 Acyl transferases Proteins 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
241000282326 Felis catus Species 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
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
101150052154 MSRA1 gene Proteins 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
241000193985 Streptococcus agalactiae Species 0.000 description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
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 3
150000001408 amides Chemical class 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
229940088710 antibiotic agent Drugs 0.000 description 3
238000013459 approach Methods 0.000 description 3
AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
229910052796 boron Inorganic materials 0.000 description 3
229910052791 calcium Inorganic materials 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
150000001735 carboxylic acids Chemical class 0.000 description 3
239000000969 carrier Substances 0.000 description 3
230000003197 catalytic effect Effects 0.000 description 3
201000010099 disease Diseases 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
150000002118 epoxides Chemical class 0.000 description 3
108091008053 gene clusters Proteins 0.000 description 3
238000006206 glycosylation reaction Methods 0.000 description 3
238000005805 hydroxylation reaction Methods 0.000 description 3
150000002576 ketones Chemical class 0.000 description 3
101150021123 msrA gene Proteins 0.000 description 3
101150114366 msrA2 gene Proteins 0.000 description 3
101150006794 msrAB gene Proteins 0.000 description 3
101150109310 msrAB1 gene Proteins 0.000 description 3
101150052209 msrAB2 gene Proteins 0.000 description 3
ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 3
231100000252 nontoxic Toxicity 0.000 description 3
230000003000 nontoxic effect Effects 0.000 description 3
239000002674 ointment Substances 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
229920000642 polymer Polymers 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
238000013207 serial dilution Methods 0.000 description 3
239000012312 sodium hydride Substances 0.000 description 3
229910000104 sodium hydride Inorganic materials 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
150000003512 tertiary amines Chemical class 0.000 description 3
KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 2
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 2
101710146995 Acyl carrier protein Proteins 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
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
108090000371 Esterases Proteins 0.000 description 2
241000605909 Fusobacterium 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
241000606790 Haemophilus Species 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
AXFZADXWLMXITO-UHFFFAOYSA-N N-acetylcysteamine Chemical compound CC(=O)NCCS AXFZADXWLMXITO-UHFFFAOYSA-N 0.000 description 2
229910002651 NO3 Inorganic materials 0.000 description 2
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
229910019142 PO4 Inorganic materials 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
241000187560 Saccharopolyspora Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
206010062255 Soft tissue infection Diseases 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000187747 Streptomyces Species 0.000 description 2
241000187432 Streptomyces coelicolor Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
241000282898 Sus scrofa Species 0.000 description 2
LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 2
FHKPLLOSJHHKNU-INIZCTEOSA-N [(3S)-3-[8-(1-ethyl-5-methylpyrazol-4-yl)-9-methylpurin-6-yl]oxypyrrolidin-1-yl]-(oxan-4-yl)methanone Chemical compound C(C)N1N=CC(=C1C)C=1N(C2=NC=NC(=C2N=1)O[C@@H]1CN(CC1)C(=O)C1CCOCC1)C FHKPLLOSJHHKNU-INIZCTEOSA-N 0.000 description 2
239000008272 agar Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
238000000429 assembly Methods 0.000 description 2
230000000712 assembly Effects 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
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 2
125000001246 bromo group Chemical group Br* 0.000 description 2
150000007942 carboxylates Chemical group 0.000 description 2
150000001732 carboxylic acid derivatives Chemical group 0.000 description 2
238000007385 chemical modification Methods 0.000 description 2
229940038705 chlamydia trachomatis Drugs 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000010276 construction Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
239000006071 cream Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
238000005516 engineering process Methods 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000001747 exhibiting effect Effects 0.000 description 2
239000000945 filler Substances 0.000 description 2
239000012467 final product Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
238000010353 genetic engineering Methods 0.000 description 2
229940047650 haemophilus influenzae Drugs 0.000 description 2
150000002431 hydrogen Chemical class 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
208000028774 intestinal disease Diseases 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
150000003951 lactams Chemical class 0.000 description 2
125000005647 linker group Chemical group 0.000 description 2
239000002502 liposome Substances 0.000 description 2
239000002609 medium Substances 0.000 description 2
101150111763 mefA gene Proteins 0.000 description 2
125000000896 monocarboxylic acid group Chemical group 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
230000001590 oxidative effect 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
229910052700 potassium Inorganic materials 0.000 description 2
239000011591 potassium Substances 0.000 description 2
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 2
RPDAUEIUDPHABB-UHFFFAOYSA-N potassium ethoxide Chemical compound [K+].CC[O-] RPDAUEIUDPHABB-UHFFFAOYSA-N 0.000 description 2
159000000001 potassium salts Chemical class 0.000 description 2
239000002243 precursor Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
230000008707 rearrangement Effects 0.000 description 2
206010040872 skin infection Diseases 0.000 description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 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
238000007920 subcutaneous administration Methods 0.000 description 2
239000000725 suspension Substances 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
239000002691 unilamellar liposome Substances 0.000 description 2
208000019206 urinary tract infection Diseases 0.000 description 2
239000013598 vector Substances 0.000 description 2
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 1
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
OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
HMUNWXXNJPVALC-UHFFFAOYSA-N 1-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)C(CN1CC2=C(CC1)NN=N2)=O HMUNWXXNJPVALC-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
VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 1
LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-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
101150055869 25 gene Proteins 0.000 description 1
YLZOPXRUQYQQID-UHFFFAOYSA-N 3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]propan-1-one Chemical compound N1N=NC=2CN(CCC=21)CCC(=O)N1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F YLZOPXRUQYQQID-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
125000006163 5-membered heteroaryl group Chemical group 0.000 description 1
DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 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
201000001320 Atherosclerosis Diseases 0.000 description 1
241001518086 Bartonella henselae Species 0.000 description 1
102000011802 Beta-ketoacyl synthases Human genes 0.000 description 1
108050002233 Beta-ketoacyl synthases Proteins 0.000 description 1
241000588807 Bordetella Species 0.000 description 1
241000180135 Borrelia recurrentis Species 0.000 description 1
241000589969 Borreliella burgdorferi Species 0.000 description 1
241001148534 Brachyspira Species 0.000 description 1
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
101710134389 Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 2 Proteins 0.000 description 1
102000014914 Carrier Proteins Human genes 0.000 description 1
108010078791 Carrier Proteins Proteins 0.000 description 1
241001409887 Chamaea fasciata Species 0.000 description 1
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
108010065152 Coagulase Proteins 0.000 description 1
241000224483 Coccidia Species 0.000 description 1
206010010741 Conjunctivitis Diseases 0.000 description 1
208000031973 Conjunctivitis infective Diseases 0.000 description 1
241001518260 Corynebacterium minutissimum Species 0.000 description 1
206010011224 Cough Diseases 0.000 description 1
208000008953 Cryptosporidiosis Diseases 0.000 description 1
VZFUCHSFHOYXIS-UHFFFAOYSA-N Cycloheptanecarboxylic acid Chemical compound OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-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
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000605721 Dichelobacter nodosus Species 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
241000588914 Enterobacter Species 0.000 description 1
241000194033 Enterococcus Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 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
230000005526 G1 to G0 transition Effects 0.000 description 1
208000005577 Gastroenteritis Diseases 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
239000004471 Glycine Substances 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
102100024407 Jouberin Human genes 0.000 description 1
101150111320 KS gene Proteins 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
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
208000016604 Lyme disease Diseases 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
241001465754 Metazoa Species 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
241000588655 Moraxella catarrhalis Species 0.000 description 1
241000699666 Mus <mouse, genus> Species 0.000 description 1
101100240347 Mus musculus Nectin2 gene Proteins 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000186367 Mycobacterium avium Species 0.000 description 1
241000513886 Mycobacterium avium complex (MAC) 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
MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
241000588652 Neisseria gonorrhoeae Species 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
108700026244 Open Reading Frames Proteins 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
241000191992 Peptostreptococcus Species 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
229920000954 Polyglycolide Polymers 0.000 description 1
108010030975 Polyketide Synthases Proteins 0.000 description 1
229920001710 Polyorthoester Polymers 0.000 description 1
239000004721 Polyphenylene oxide Substances 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
241000607142 Salmonella Species 0.000 description 1
206010040070 Septic Shock Diseases 0.000 description 1
244000000231 Sesamum indicum Species 0.000 description 1
208000019802 Sexually transmitted disease Diseases 0.000 description 1
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
244000061456 Solanum tuberosum Species 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
241000191963 Staphylococcus epidermidis Species 0.000 description 1
241000191984 Staphylococcus haemolyticus Species 0.000 description 1
241001147691 Staphylococcus saprophyticus Species 0.000 description 1
101000870438 Streptococcus gordonii UDP-N-acetylglucosamine-peptide N-acetylglucosaminyltransferase stabilizing protein GtfB Proteins 0.000 description 1
241001312524 Streptococcus viridans Species 0.000 description 1
108010015795 Streptogramin B Proteins 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
102100036236 Synaptonemal complex protein 2 Human genes 0.000 description 1
206010044248 Toxic shock syndrome Diseases 0.000 description 1
231100000650 Toxic shock syndrome Toxicity 0.000 description 1
102000004357 Transferases Human genes 0.000 description 1
108090000992 Transferases Proteins 0.000 description 1
241000589884 Treponema pallidum Species 0.000 description 1
208000025865 Ulcer Diseases 0.000 description 1
241000202921 Ureaplasma urealyticum Species 0.000 description 1
208000006374 Uterine Cervicitis Diseases 0.000 description 1
101000645119 Vibrio campbellii (strain ATCC BAA-1116 / BB120) Nucleotide-binding protein VIBHAR_03667 Proteins 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 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
206010000269 abscess Diseases 0.000 description 1
238000010306 acid treatment Methods 0.000 description 1
230000004913 activation Effects 0.000 description 1
108091006088 activator proteins Proteins 0.000 description 1
201000001028 acute contagious conjunctivitis Diseases 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
101150057036 acyI gene Proteins 0.000 description 1
238000002814 agar dilution Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
150000001413 amino acids Chemical class 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
230000000507 anthelmentic effect Effects 0.000 description 1
230000001093 anti-cancer Effects 0.000 description 1
230000000843 anti-fungal effect Effects 0.000 description 1
230000000845 anti-microbial effect Effects 0.000 description 1
238000011482 antibacterial activity assay Methods 0.000 description 1
229940121375 antifungal agent Drugs 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
238000011203 antimicrobial therapy Methods 0.000 description 1
239000003904 antiprotozoal agent Substances 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 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
101150036080 at gene Proteins 0.000 description 1
229940092524 bartonella henselae Drugs 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical compound COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 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
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
OPBURCVWOKTFHZ-UHFFFAOYSA-N benzyl 1-hydroxy-2,5-dioxopyrrolidine-3-carboxylate Chemical compound O=C1N(O)C(=O)CC1C(=O)OCC1=CC=CC=C1 OPBURCVWOKTFHZ-UHFFFAOYSA-N 0.000 description 1
PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 description 1
230000002457 bidirectional effect Effects 0.000 description 1
230000027455 binding Effects 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
230000037396 body weight Effects 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000012267 brine Substances 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
239000002775 capsule Substances 0.000 description 1
150000001733 carboxylic acid esters Chemical class 0.000 description 1
150000001734 carboxylic acid salts Chemical class 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
206010008323 cervicitis Diseases 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000004040 coloring Methods 0.000 description 1
235000009508 confectionery Nutrition 0.000 description 1
238000013270 controlled release Methods 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
238000012258 culturing Methods 0.000 description 1
238000005520 cutting process Methods 0.000 description 1
235000013365 dairy product Nutrition 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
238000003113 dilution method Methods 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
229940079593 drug Drugs 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
238000006735 epoxidation reaction Methods 0.000 description 1
101150016744 ermC gene Proteins 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 description 1
238000002474 experimental method Methods 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
230000002349 favourable effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
208000010801 foot rot Diseases 0.000 description 1
239000007789 gas Substances 0.000 description 1
230000030135 gastric motility Effects 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 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
229940093915 gynecological organic acid Drugs 0.000 description 1
150000003278 haem Chemical class 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
239000000017 hydrogel Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
230000033444 hydroxylation Effects 0.000 description 1
150000002466 imines Chemical class 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
230000000415 inactivating effect Effects 0.000 description 1
230000002779 inactivation Effects 0.000 description 1
238000011534 incubation Methods 0.000 description 1
238000001802 infusion Methods 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
238000003780 insertion Methods 0.000 description 1
230000037431 insertion Effects 0.000 description 1
230000000968 intestinal effect Effects 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
238000010253 intravenous injection Methods 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
TWBYWOBDOCUKOW-UHFFFAOYSA-M isonicotinate Chemical compound [O-]C(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-M 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
206010023332 keratitis Diseases 0.000 description 1
239000008101 lactose Substances 0.000 description 1
229940041028 lincosamides Drugs 0.000 description 1
239000007788 liquid Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
229940040692 lithium hydroxide monohydrate Drugs 0.000 description 1
GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 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
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
208000004396 mastitis Diseases 0.000 description 1
239000000463 material Substances 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
239000003863 metallic catalyst Substances 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing 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
238000012544 monitoring process Methods 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
KPADFPAILITQBG-UHFFFAOYSA-N non-4-ene Chemical compound CCCCC=CCCC KPADFPAILITQBG-UHFFFAOYSA-N 0.000 description 1
150000007523 nucleic acids Chemical class 0.000 description 1
102000039446 nucleic acids Human genes 0.000 description 1
108020004707 nucleic acids Proteins 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
229960002351 oleandomycin Drugs 0.000 description 1
235000019367 oleandomycin Nutrition 0.000 description 1
239000008203 oral pharmaceutical composition Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 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
239000006072 paste Substances 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
230000000144 pharmacologic effect Effects 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
150000008105 phosphatidylcholines Chemical class 0.000 description 1
230000026731 phosphorylation Effects 0.000 description 1
238000006366 phosphorylation reaction Methods 0.000 description 1
239000000049 pigment Substances 0.000 description 1
239000013600 plasmid vector Substances 0.000 description 1
229920000747 poly(lactic acid) Polymers 0.000 description 1
229920002721 polycyanoacrylate Polymers 0.000 description 1
229920000570 polyether 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
238000003752 polymerase chain reaction Methods 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
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000843 powder Substances 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
230000001681 protective effect Effects 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000005215 recombination Methods 0.000 description 1
230000006798 recombination Effects 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
208000023504 respiratory system disease Diseases 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
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
230000007017 scission Effects 0.000 description 1
238000012216 screening Methods 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
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 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
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
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-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
239000000126 substance 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
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000001502 supplementing effect Effects 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000375 suspending 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
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
MFPWEWYKQYMWRO-UHFFFAOYSA-N tert-butyl carboxy carbonate Chemical compound CC(C)(C)OC(=O)OC(O)=O MFPWEWYKQYMWRO-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000005207 tetraalkylammonium group Chemical group 0.000 description 1
229950002881 tetronasin Drugs 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
150000007970 thio esters Chemical class 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000003053 toxin Substances 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
238000013518 transcription Methods 0.000 description 1
230000035897 transcription Effects 0.000 description 1
230000009466 transformation Effects 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
231100000397 ulcer Toxicity 0.000 description 1
208000000143 urethritis Diseases 0.000 description 1
GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 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
- 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
- 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

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)
Engineering & Computer Science (AREA)
Genetics & Genomics (AREA)
Biochemistry (AREA)
Veterinary Medicine (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)
Communicable Diseases (AREA)
Oncology (AREA)
Tropical Medicine & Parasitology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

OA1200000192A 1998-01-02 2000-06-30 Novel macrolides. OA11438A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US7034398P	1998-01-02	1998-01-02

Publications (1)

Publication Number	Publication Date
OA11438A true OA11438A (en)	2004-04-30

Family

ID=22094723

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200000192A OA11438A (en)	1998-01-02	2000-06-30	Novel macrolides.

Country Status (34)

Country	Link
US (2)	US6472371B1 (is)
EP (1)	EP1044207A1 (is)
JP (1)	JP2002500230A (is)
KR (1)	KR100352809B1 (is)
CN (1)	CN1284081A (is)
AP (1)	AP9801420A0 (is)
AR (4)	AR014948A1 (is)
AU (1)	AU756409B2 (is)
BG (1)	BG104644A (is)
BR (1)	BR9814601A (is)
CA (1)	CA2316919C (is)
CO (1)	CO4970821A1 (is)
CZ (1)	CZ20002458A3 (is)
DZ (1)	DZ2698A1 (is)
EA (1)	EA200000594A1 (is)
GT (1)	GT199800206A (is)
HR (1)	HRP20000442A2 (is)
HU (1)	HUP0100420A3 (is)
IL (1)	IL137024A0 (is)
IS (1)	IS5528A (is)
MA (1)	MA24729A1 (is)
NO (1)	NO20003347L (is)
NZ (1)	NZ504986A (is)
OA (1)	OA11438A (is)
PA (1)	PA8465301A1 (is)
PE (1)	PE20000049A1 (is)
PL (1)	PL341642A1 (is)
SK (1)	SK9782000A3 (is)
TN (1)	TNSN98238A1 (is)
TW (1)	TW520374B (is)
UY (2)	UY25330A1 (is)
WO (1)	WO1999035156A1 (is)
YU (1)	YU41500A (is)
ZA (1)	ZA9811939B (is)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
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.
EP1437360A3 (en) *	1998-08-19	2005-04-06	Pfizer Products Inc.	C11 Carbamates of macrolide antibacterials
US6043227A (en) *	1998-08-19	2000-03-28	Pfizer Inc.	C11 carbamates of macrolide antibacterials
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
IL145976A0 (en)	1999-04-16	2002-07-25	Ortho Mcneil Pharm Inc	Ketolide antibacterials
US6590083B1 (en)	1999-04-16	2003-07-08	Ortho-Mcneil Pharmaceutical, Inc.	Ketolide antibacterials
EA200100983A1 (ru)	1999-05-24	2002-10-31	Пфайзер Продактс Инк.	Производные 13-метилэритромицина
JPWO2003072589A1 (ja) *	2002-02-26	2005-06-16	明治製菓株式会社	新規１５員環アザライド及び新規１６員環ジアザライド誘導体とその製造法
BRPI0515917A (pt)	2004-09-23	2008-08-12	Schering Plough Ltd	controle de parasitas em animais pelo uso de novos derivados de éter de oxima de trifluorometanossulfonanilida
EP1811841B1 (en) *	2004-11-19	2009-10-28	Schering-Plough Ltd.	Control of parasites in animals by the use of parasiticidal 2-phenyl-3-(1h-pyrrol-2-yl) acrylonitrile derivatives
UA85937C2 (uk)	2004-12-21	2009-03-10	Пфайзер Продактс Інк.	Макроліди
WO2006135648A2 (en) *	2005-06-09	2006-12-21	Schering-Plough Ltd.	Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives
US8119667B2 (en) *	2005-12-29	2012-02-21	Schering-Plough Animal Health Corporation	Carbonates of fenicol antibiotics
US20070238700A1 (en) *	2006-04-10	2007-10-11	Winzenberg Kevin N	N-phenyl-1,1,1-trifluoromethanesulfonamide hydrazone derivative compounds and their usage in controlling parasites
WO2008076259A1 (en) *	2006-12-13	2008-06-26	Schering-Plough Ltd.	Water-soluble prodrugs of florfenicol and its analogs
CA2672795A1 (en) *	2006-12-13	2008-06-26	Schering-Plough Ltd.	Water-soluble prodrugs of chloramphenicol, thiamphenicol, and analogs thereof
TWI430995B (zh)	2007-06-26	2014-03-21	Du Pont	萘異唑啉無脊椎有害動物控制劑
KR101769728B1 (ko)	2007-06-27	2017-08-18	이 아이 듀폰 디 네모아 앤드 캄파니	동물 해충 방제 방법
WO2009064953A1 (en) *	2007-11-15	2009-05-22	Enanta Pharmaceuticals, Inc.	Use of bridged macrolides or tylosin derivatives in treating inflammatory bowel diseases
TWI468407B (zh)	2008-02-06	2015-01-11	Du Pont	中離子農藥
WO2010014566A2 (en) *	2008-07-30	2010-02-04	Intervet International B.V.	Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol
UA110924C2 (uk)	2009-08-05	2016-03-10	Е. І. Дю Пон Де Немур Енд Компані	Мезоіонні пестициди
KR20120050467A (ko)	2009-08-05	2012-05-18	이 아이 듀폰 디 네모아 앤드 캄파니	메소이온성 살충제
US20120122680A1 (en)	2009-08-05	2012-05-17	E.I. Du Pont De Nemours And Company	Mesoionic pesticides
UA107804C2 (xx)	2009-08-05	2015-02-25	Du Pont	Суміші мезоіонних пестицидів
UA108881C2 (xx)	2010-05-27	2015-06-25		Кристалічна форма 4-$5-$3-хлор-5-(трифторметил)феніл]-4,5-дигідро-5-(трифторметил)-3-ізоксазоліл]-n-$2-оксо-2-$(2,2,2-трифторетил)аміно]етил]-1-нафталінкарбоксаміду
WO2012087630A1 (en)	2010-12-20	2012-06-28	E.I. Du Pont De Nemours And Company	Pyridine and pyrimidine compounds for controlling invertebrate
KR20140004187A (ko) *	2011-01-31	2014-01-10	메이지 세이카 파루마 가부시키가이샤	신규 마크로라이드 유도체
JP2014520151A (ja)	2011-06-20	2014-08-21	イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー	蠕虫感染を処置するためのヘテロ環式化合物
CN102260306B (zh) *	2011-07-22	2012-07-18	山东鲁抗舍里乐药业有限公司	一种制备泰拉霉素的方法
TW201326128A (zh)	2011-11-28	2013-07-01	Du Pont	磺醯胺驅蟲劑
WO2013158422A1 (en)	2012-04-17	2013-10-24	E. I. Du Pont De Nemours And Company	Heterocyclic compounds for controlling invertebrate pests
WO2014099837A1 (en)	2012-12-18	2014-06-26	E. I. Du Pont De Nemours And Company	Sulfonamide anthelmintics
CN105669798B (zh) *	2013-08-23	2019-07-26	普莱柯生物工程股份有限公司	一种大环内酯类化合物
CN103965273B (zh) *	2013-08-23	2016-05-25	普莱柯生物工程股份有限公司	一种大环内酯类化合物

Family Cites Families (36)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3652537A (en)	1969-11-21	1972-03-28	Lilly Co Eli	Epierythromycylamine and epierythromycyl b amine
US3923784A (en)	1973-09-10	1975-12-02	Hoffmann La Roche	Erythromycin a derivatives
SI7910768A8 (en)	1979-04-02	1996-06-30	Pliva Pharm & Chem Works	Process for pripering 11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl- 7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl- oxacyclopentadecane-2-one and their derivatives
US4474768A (en)	1982-07-19	1984-10-02	Pfizer Inc.	N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor
US4585759A (en)	1985-01-22	1986-04-29	Pfizer Inc.	Antibacterial derivatives of a neutral macrolide
EP0283055B1 (en) *	1987-09-03	1990-08-29	SOUR PLIVA farmaceutska, Kemijska prehrambena i kozmeticka industrija, n.sol.o.	10-dihydro-10-deoxo-11-azaerythronolide-a-compounds, methods and intermediates for the manufacture thereof and their use in pharmaceuticals and in the manufacture thereof
US5141926A (en)	1990-04-18	1992-08-25	Abbott Laboratories	Erythromycin derivatives
US5824513A (en)	1991-01-17	1998-10-20	Abbott Laboratories	Recombinant DNA method for producing erythromycin analogs
WO1993013663A1 (en)	1992-01-17	1993-07-22	Abbott Laboratories	Method of directing biosynthesis of specific polyketides
US5985844A (en)	1992-03-26	1999-11-16	Merck & Co., Inc.	Homoerythromycin A derivatives modified at the 4"-and 8A-positions
CA2065218A1 (en)	1991-04-11	1992-10-12	Robert R. Wilkening	Process for the preparation of 9-deoxo-8a-aza-8a-homoerythromycin a and its 8a-alkyl derivatives
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.
US5332807A (en) *	1993-04-14	1994-07-26	Merck & Co., Inc.	Process of producing 8A- and 9A-azalide antibiotics
US5441939A (en) *	1994-03-04	1995-08-15	Pfizer Inc.	3"-desmethoxy derivatives of erythromycin and azithromycin
US6271255B1 (en)	1996-07-05	2001-08-07	Biotica Technology Limited	Erythromycins and process for their preparation
WO1998051696A1 (en)	1997-05-09	1998-11-19	Pfizer Products Inc.	Erythromycin derivatives
HN1998000086A (es)	1997-06-11	1999-03-08	Pfizer Prod Inc	Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - c - 4 sustituidos.
HN1998000074A (es) *	1997-06-11	1999-01-08	Pfizer Prod Inc	Derivados de macrolidos c-4 sustituidos
US6407074B1 (en)	1997-06-11	2002-06-18	Pfizer Inc	C-4″-substituted macrolide derivatives
US20020025937A1 (en)	2000-03-20	2002-02-28	Yong-Jin Wu	9-oxime erythromycin derivatives
WO1999000124A1 (en)	1997-06-26	1999-01-07	Merck & Co., Inc.	9a-azalides, compositions containing such compounds and methods of treatment
US6339063B1 (en)	1997-09-10	2002-01-15	Merck & Co., Inc.	9a-azalides as veterinary antimicrobial agents
PA8461401A1 (es)	1997-10-29	2000-05-24	Pfizer Prod Inc	Derivados de eritromicina triciclicos
HN1998000159A (es)	1997-10-29	1999-02-09	Monsanto Co	Derivados de 9- amino - 3 ceto eritromicina
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.
PT941998E (pt)	1998-03-03	2004-12-31	Pfizer Prod Inc	Antibioticos macrolidos do tipo 3,6-cetal
AU3439899A (en)	1998-06-03	1999-12-20	Pfizer Products Inc.	Tricyclic 3-keto derivatives of 6-o-methylerythromycin
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
KR20010083944A (ko)	1998-11-03	2001-09-03	실버스타인 아써 에이.	신규 마크롤라이드 항생물질
UA70972C2 (uk)	1998-11-20	2004-11-15	Пфайзер Продактс Інк.	13-членні азаліди і їх застосування як антибіотиків
EA200100983A1 (ru)	1999-05-24	2002-10-31	Пфайзер Продактс Инк.	Производные 13-метилэритромицина
EP1101769A3 (en)	1999-11-18	2001-10-24	Pfizer Products Inc.	Nitrogen containing erythromycin derivatives
JP4311203B2 (ja)	2001-08-08	2009-08-12	大正製薬株式会社	１１ａ−アザライド化合物及びその製造方法

1998
- 1998-12-17 AP APAP/P/1998/001420A patent/AP9801420A0/en unknown
- 1998-12-21 IL IL13702498A patent/IL137024A0/xx unknown
- 1998-12-21 SK SK978-2000A patent/SK9782000A3/sk unknown
- 1998-12-21 CA CA002316919A patent/CA2316919C/en not_active Expired - Fee Related
- 1998-12-21 EP EP98958384A patent/EP1044207A1/en not_active Withdrawn
- 1998-12-21 YU YU41500A patent/YU41500A/sh unknown
- 1998-12-21 AU AU14447/99A patent/AU756409B2/en not_active Ceased
- 1998-12-21 CN CN98813253A patent/CN1284081A/zh active Pending
- 1998-12-21 NZ NZ504986A patent/NZ504986A/xx unknown
- 1998-12-21 HU HU0100420A patent/HUP0100420A3/hu unknown
- 1998-12-21 JP JP2000527552A patent/JP2002500230A/ja active Pending
- 1998-12-21 PL PL98341642A patent/PL341642A1/xx unknown
- 1998-12-21 CZ CZ20002458A patent/CZ20002458A3/cs unknown
- 1998-12-21 KR KR1020007007313A patent/KR100352809B1/ko not_active Expired - Fee Related
- 1998-12-21 WO PCT/IB1998/002099 patent/WO1999035156A1/en not_active Ceased
- 1998-12-21 BR BR9814601-7A patent/BR9814601A/pt not_active IP Right Cessation
- 1998-12-21 HR HR20000442A patent/HRP20000442A2/hr not_active Application Discontinuation
- 1998-12-21 US US09/554,988 patent/US6472371B1/en not_active Expired - Fee Related
- 1998-12-22 EA EA200000594A patent/EA200000594A1/ru unknown
- 1998-12-23 PA PA19988465301A patent/PA8465301A1/es unknown
- 1998-12-23 TW TW087121542A patent/TW520374B/zh not_active IP Right Cessation
- 1998-12-28 PE PE1998001287A patent/PE20000049A1/es not_active Application Discontinuation
- 1998-12-29 AR ARP980106717A patent/AR014948A1/es not_active Application Discontinuation
- 1998-12-29 GT GT199800206A patent/GT199800206A/es unknown
- 1998-12-30 UY UY25330A patent/UY25330A1/es not_active Application Discontinuation
- 1998-12-30 CO CO98077585A patent/CO4970821A1/es unknown
- 1998-12-30 DZ DZ980308A patent/DZ2698A1/xx active
- 1998-12-30 TN TNTNSN98238A patent/TNSN98238A1/fr unknown
- 1998-12-30 MA MA25407A patent/MA24729A1/fr unknown
- 1998-12-30 ZA ZA9811939A patent/ZA9811939B/xx unknown
1999
- 1999-06-18 UY UY25574A patent/UY25574A1/es not_active Application Discontinuation
- 1999-11-29 AR ARP990106063A patent/AR020851A2/es not_active Application Discontinuation
- 1999-11-29 AR ARP990106062A patent/AR019787A2/es not_active Application Discontinuation
- 1999-11-29 AR ARP990106064A patent/AR020551A2/es not_active Application Discontinuation
2000
- 2000-06-09 IS IS5528A patent/IS5528A/is unknown
- 2000-06-27 NO NO20003347A patent/NO20003347L/no unknown
- 2000-06-30 OA OA1200000192A patent/OA11438A/en unknown
- 2000-07-28 BG BG104644A patent/BG104644A/xx unknown
2002
- 2002-07-30 US US10/209,682 patent/US7015203B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
HUP0100420A3 (en)	2003-07-28
DZ2698A1 (fr)	2003-03-29
PE20000049A1 (es)	2000-02-07
IL137024A0 (en)	2001-06-14
BG104644A (en)	2001-01-31
WO1999035156A1 (en)	1999-07-15
US20040092459A1 (en)	2004-05-13
SK9782000A3 (en)	2001-12-03
HRP20000442A2 (en)	2001-04-30
CN1284081A (zh)	2001-02-14
GT199800206A (es)	2000-06-21
HUP0100420A2 (hu)	2001-07-30
KR100352809B1 (ko)	2002-11-01
PL341642A1 (en)	2001-04-23
AU756409B2 (en)	2003-01-09
YU41500A (sh)	2003-02-28
AP9801420A0 (en)	1998-12-31
AR020851A2 (es)	2002-05-29
AR020551A2 (es)	2002-05-15
CO4970821A1 (es)	2000-11-07
CA2316919C (en)	2004-10-26
MA24729A1 (fr)	1999-07-01
IS5528A (is)	2000-06-09
NZ504986A (en)	2003-03-28
KR20010024818A (ko)	2001-03-26
NO20003347L (no)	2000-08-28
TNSN98238A1 (fr)	2005-03-15
TW520374B (en)	2003-02-11
US7015203B2 (en)	2006-03-21
NO20003347D0 (no)	2000-06-27
CZ20002458A3 (cs)	2001-10-17
AU1444799A (en)	1999-07-26
UY25330A1 (es)	2000-12-29
PA8465301A1 (es)	2000-09-29
ZA9811939B (en)	2000-06-30
US6472371B1 (en)	2002-10-29
CA2316919A1 (en)	1999-07-15
AR019787A2 (es)	2002-03-13
UY25574A1 (es)	1999-09-27
EA200000594A1 (ru)	2001-04-23
EP1044207A1 (en)	2000-10-18
WO1999035156B1 (en)	1999-10-21
AR014948A1 (es)	2001-04-11
BR9814601A (pt)	2000-10-17
JP2002500230A (ja)	2002-01-08

Publication	Publication Date	Title
OA11438A (en)	2004-04-30	Novel macrolides.
AU759019B2 (en)	2003-04-03	Novel erythromycin derivatives
US6777543B2 (en)	2004-08-17	13-methyl erythromycin derivatives
EP0988310A1 (en)	2000-03-29	4"-substituted-9-deoxo-9a-aza-9a-homoerythromycin a derivatives
CA2293335A1 (en)	1998-12-17	9-oxime erythromycin derivatives
CA2351429C (en)	2005-07-12	13-membered azalides and their use as antibiotic agents
AU5995299A (en)	2000-05-22	Novel macrolide antibiotics
EP0992509B1 (en)	2004-09-22	Novel macrolide derivatives
EP0984019B1 (en)	2004-06-02	C11 carbamates of macrolide antibacterials
US6162794A (en)	2000-12-19	Erythromycin derivatives
US20020151507A1 (en)	2002-10-17	9-oxime erythromycin derivatives
WO1999062920A1 (en)	1999-12-09	Tricyclic 3-keto derivatives of 6-o-methylerythromycin
MXPA00006604A (en)	2001-06-26	Novel macrolides
MXPA00006602A (en)	2001-06-26	Novel erythromycin derivatives