OA11438A - Novel macrolides. - Google Patents
Novel macrolides. Download PDFInfo
- Publication number
- OA11438A OA11438A OA1200000192A OA1200000192A OA11438A OA 11438 A OA11438 A OA 11438A OA 1200000192 A OA1200000192 A OA 1200000192A OA 1200000192 A OA1200000192 A OA 1200000192A OA 11438 A OA11438 A OA 11438A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- groups
- optionally
- substituted
- halo
- Prior art date
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- 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
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- 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
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- 229910052708 sodium Inorganic materials 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
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- 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
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- 238000004949 mass spectrometry Methods 0.000 description 5
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- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
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- 150000001408 amides Chemical class 0.000 description 3
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- AYJRCSIUFZENHW-DEQYMQKBSA-L barium(2+);oxomethanediolate Chemical compound [Ba+2].[O-][14C]([O-])=O AYJRCSIUFZENHW-DEQYMQKBSA-L 0.000 description 3
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- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
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- 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
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- 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
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- 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)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
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 (es) |
| EP (1) | EP1044207A1 (es) |
| JP (1) | JP2002500230A (es) |
| KR (1) | KR100352809B1 (es) |
| CN (1) | CN1284081A (es) |
| AP (1) | AP9801420A0 (es) |
| AR (4) | AR014948A1 (es) |
| AU (1) | AU756409B2 (es) |
| BG (1) | BG104644A (es) |
| BR (1) | BR9814601A (es) |
| CA (1) | CA2316919C (es) |
| CO (1) | CO4970821A1 (es) |
| CZ (1) | CZ20002458A3 (es) |
| DZ (1) | DZ2698A1 (es) |
| EA (1) | EA200000594A1 (es) |
| GT (1) | GT199800206A (es) |
| HR (1) | HRP20000442A2 (es) |
| HU (1) | HUP0100420A3 (es) |
| IL (1) | IL137024A0 (es) |
| IS (1) | IS5528A (es) |
| MA (1) | MA24729A1 (es) |
| NO (1) | NO20003347L (es) |
| NZ (1) | NZ504986A (es) |
| OA (1) | OA11438A (es) |
| PA (1) | PA8465301A1 (es) |
| PE (1) | PE20000049A1 (es) |
| PL (1) | PL341642A1 (es) |
| SK (1) | SK9782000A3 (es) |
| TN (1) | TNSN98238A1 (es) |
| TW (1) | TW520374B (es) |
| UY (2) | UY25330A1 (es) |
| WO (1) | WO1999035156A1 (es) |
| YU (1) | YU41500A (es) |
| ZA (1) | ZA9811939B (es) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
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| 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. |
| US6043227A (en) * | 1998-08-19 | 2000-03-28 | Pfizer Inc. | C11 carbamates of macrolide antibacterials |
| EP1437360A3 (en) * | 1998-08-19 | 2005-04-06 | Pfizer Products Inc. | C11 Carbamates of macrolide antibacterials |
| EP1754700A3 (en) | 1999-01-27 | 2007-05-09 | Kosan Biosciences, Inc. | Synthesis of oligoketides |
| CA2370743A1 (en) | 1999-04-16 | 2000-10-26 | Dennis Hlasta | Ketolide antibacterials |
| US6590083B1 (en) | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| US6451768B1 (en) | 1999-04-16 | 2002-09-17 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| BR0010938A (pt) | 1999-05-24 | 2002-03-19 | Pfizer Prod Inc | Derivados da 13-metil eritromicina |
| 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 |
| NZ553777A (en) | 2004-09-23 | 2010-11-26 | Schering Plough Ltd | Control of parasites in animals by the use of novel trifluoromethanesulfonanilide oxime ether derivatives |
| MX2007006072A (es) * | 2004-11-19 | 2007-07-11 | Schering Plough Ltd | Control de parasitos en animales mediante el uso de derivados del parasiticida 2-fenil-3-(1h-pirrol-2-il)acrilonitrilo. |
| PL1836211T3 (pl) | 2004-12-21 | 2010-07-30 | Pfizer Prod Inc | Makrolidy |
| EP1890547A2 (en) * | 2005-06-09 | 2008-02-27 | Schering-Plough Ltd. | Control of parasites in animals by n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide and n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide derivatives |
| US8119667B2 (en) * | 2005-12-29 | 2012-02-21 | Schering-Plough Animal Health Corporation | Carbonates of fenicol antibiotics |
| 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 |
| EP2091909A1 (en) * | 2006-12-13 | 2009-08-26 | Schering-Plough Ltd. | Water-soluble prodrugs of florfenicol and its analogs |
| MX2009006467A (es) * | 2006-12-13 | 2009-08-21 | Schering Plough Ltd | Profarmacos solubles en agua de cloranfenicol, tiamfenicol y analogos de los mismos. |
| TWI430995B (zh) | 2007-06-26 | 2014-03-21 | Du Pont | 萘異唑啉無脊椎有害動物控制劑 |
| MX368680B (es) | 2007-06-27 | 2019-10-11 | Du Pont | Administración subcutánea de un derivado de isoxazol-benzamida para usarse en un método para proteger un mamífero de una pulga. |
| WO2009064953A1 (en) * | 2007-11-15 | 2009-05-22 | Enanta Pharmaceuticals, Inc. | Use of bridged macrolides or tylosin derivatives in treating inflammatory bowel diseases |
| TWI401023B (zh) | 2008-02-06 | 2013-07-11 | Du Pont | 中離子農藥 |
| CA2732017A1 (en) * | 2008-07-30 | 2010-02-04 | Intervet International B.V. | Process for preparing oxazoline-protected aminodiol compounds useful as intermediates to florfenicol |
| BR112012002524A2 (pt) | 2009-08-05 | 2019-09-24 | Du Pont | "composto de fórmula, composição, composição para proteger um animal de uma praga parasítica de invertebrados, métodos para controlar uma praga invertebrada e semente tratada" |
| UA107804C2 (en) | 2009-08-05 | 2015-02-25 | Du Pont | Mixtures of pesticides mezoionnyh |
| EP2461684A2 (en) | 2009-08-05 | 2012-06-13 | E. I. du Pont de Nemours and Company | Mesoionic pesticides |
| UA110924C2 (uk) | 2009-08-05 | 2016-03-10 | Е. І. Дю Пон Де Немур Енд Компані | Мезоіонні пестициди |
| MA34247B1 (fr) | 2010-05-27 | 2013-05-02 | Du Pont | Forme cristalline du 4-[5-[3-chloro-5-(trifluorométhyl) phényl] -4,5-dihydro-5-(trifluorométhyl)-3-isoxazolyl]-n-[2-oxo-2-[(2, 2,2-trifluoroéthyl) amino] éthyl]-1-naphtalènecarboxamide |
| WO2012087630A1 (en) | 2010-12-20 | 2012-06-28 | E.I. Du Pont De Nemours And Company | Pyridine and pyrimidine compounds for controlling invertebrate |
| BR112013019283A2 (pt) * | 2011-01-31 | 2016-09-13 | Meiji Seika Pharma Co Ltd | composto, fármaco, composição farmacêutica e uso |
| 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 |
| RU2014126367A (ru) | 2011-11-28 | 2016-01-27 | Е.И.Дюпон Де Немур Энд Компани | Производные n-(4-хинолинметил)сульфонамидов и их применение в качестве антигельминтных средств |
| 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 |
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| 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 |
| YU43116B (en) | 1979-04-02 | 1989-04-30 | Pliva Pharm & Chem Works | Process for preparing 11-aza-4-o-cladinosyl-6-o-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one(11-aza-10-deox |
| 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 |
| HU198913B (en) * | 1987-09-03 | 1989-12-28 | Pliva Pharm & Chem Works | Process for producing 10-dihydro-10-deoxo-11-aza-erythronolide a-derivatives and pharmaceutical compositions containing them as active components |
| US5141926A (en) | 1990-04-18 | 1992-08-25 | Abbott Laboratories | Erythromycin derivatives |
| 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 |
| 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 |
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| US6407074B1 (en) | 1997-06-11 | 2002-06-18 | Pfizer Inc | C-4″-substituted macrolide derivatives |
| HN1998000086A (es) | 1997-06-11 | 1999-03-08 | Pfizer Prod Inc | Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - c - 4 sustituidos. |
| US20020025937A1 (en) | 2000-03-20 | 2002-02-28 | Yong-Jin Wu | 9-oxime erythromycin derivatives |
| HN1998000074A (es) * | 1997-06-11 | 1999-01-08 | Pfizer Prod Inc | Derivados de macrolidos c-4 sustituidos |
| AU7961498A (en) | 1997-06-26 | 1999-01-19 | 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 |
| HN1998000159A (es) | 1997-10-29 | 1999-02-09 | Monsanto Co | Derivados de 9- amino - 3 ceto eritromicina |
| PA8461401A1 (es) | 1997-10-29 | 2000-05-24 | Pfizer Prod Inc | Derivados de eritromicina triciclicos |
| 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. |
| DE69919769T2 (de) | 1998-03-03 | 2005-01-27 | Pfizer Products Inc., Groton | 3,6-Ketal-Makrolidantibiotika |
| US6248719B1 (en) | 1998-06-03 | 2001-06-19 | Pfizer Inc | Tricyclic 3-keto derivatives of 6-O-methylerthromycin |
| 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 |
| ID28286A (id) | 1998-11-03 | 2001-05-10 | Pfizer Prod Inc | Antibiotik-antibiotik makrolida baru |
| UA70972C2 (uk) | 1998-11-20 | 2004-11-15 | Пфайзер Продактс Інк. | 13-членні азаліди і їх застосування як антибіотиків |
| BR0010938A (pt) | 1999-05-24 | 2002-03-19 | Pfizer Prod Inc | Derivados da 13-metil eritromicina |
| 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 BR BR9814601-7A patent/BR9814601A/pt not_active IP Right Cessation
- 1998-12-21 HU HU0100420A patent/HUP0100420A3/hu unknown
- 1998-12-21 PL PL98341642A patent/PL341642A1/xx unknown
- 1998-12-21 IL IL13702498A patent/IL137024A0/xx unknown
- 1998-12-21 SK SK978-2000A patent/SK9782000A3/sk unknown
- 1998-12-21 CN CN98813253A patent/CN1284081A/zh active Pending
- 1998-12-21 YU YU41500A patent/YU41500A/sh unknown
- 1998-12-21 CZ CZ20002458A patent/CZ20002458A3/cs unknown
- 1998-12-21 NZ NZ504986A patent/NZ504986A/xx unknown
- 1998-12-21 KR KR1020007007313A patent/KR100352809B1/ko not_active Expired - Fee Related
- 1998-12-21 EP EP98958384A patent/EP1044207A1/en not_active Withdrawn
- 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
- 1998-12-21 JP JP2000527552A patent/JP2002500230A/ja active Pending
- 1998-12-21 CA CA002316919A patent/CA2316919C/en not_active Expired - Fee Related
- 1998-12-21 AU AU14447/99A patent/AU756409B2/en not_active Ceased
- 1998-12-21 WO PCT/IB1998/002099 patent/WO1999035156A1/en not_active Ceased
- 1998-12-22 EA EA200000594A patent/EA200000594A1/ru unknown
- 1998-12-23 TW TW087121542A patent/TW520374B/zh not_active IP Right Cessation
- 1998-12-23 PA PA19988465301A patent/PA8465301A1/es unknown
- 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 ZA ZA9811939A patent/ZA9811939B/xx unknown
- 1998-12-30 UY UY25330A patent/UY25330A1/es not_active Application Discontinuation
- 1998-12-30 TN TNTNSN98238A patent/TNSN98238A1/fr unknown
- 1998-12-30 DZ DZ980308A patent/DZ2698A1/xx active
- 1998-12-30 MA MA25407A patent/MA24729A1/fr unknown
- 1998-12-30 CO CO98077585A patent/CO4970821A1/es unknown
-
1999
- 1999-06-18 UY UY25574A patent/UY25574A1/es not_active Application Discontinuation
- 1999-11-29 AR ARP990106064A patent/AR020551A2/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
-
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
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2002
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