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
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101100119095 Enterococcus faecalis (strain ATCC 700802 / V583) ermB gene Proteins 0.000 description 6
108090000790 Enzymes Proteins 0.000 description 6
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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
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125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
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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
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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 (fr)
EP (1)	EP1044207A1 (fr)
JP (1)	JP2002500230A (fr)
KR (1)	KR100352809B1 (fr)
CN (1)	CN1284081A (fr)
AP (1)	AP9801420A0 (fr)
AR (4)	AR014948A1 (fr)
AU (1)	AU756409B2 (fr)
BG (1)	BG104644A (fr)
BR (1)	BR9814601A (fr)
CA (1)	CA2316919C (fr)
CO (1)	CO4970821A1 (fr)
CZ (1)	CZ20002458A3 (fr)
DZ (1)	DZ2698A1 (fr)
EA (1)	EA200000594A1 (fr)
GT (1)	GT199800206A (fr)
HR (1)	HRP20000442A2 (fr)
HU (1)	HUP0100420A3 (fr)
IL (1)	IL137024A0 (fr)
IS (1)	IS5528A (fr)
MA (1)	MA24729A1 (fr)
NO (1)	NO20003347L (fr)
NZ (1)	NZ504986A (fr)
OA (1)	OA11438A (fr)
PA (1)	PA8465301A1 (fr)
PE (1)	PE20000049A1 (fr)
PL (1)	PL341642A1 (fr)
SK (1)	SK9782000A3 (fr)
TN (1)	TNSN98238A1 (fr)
TW (1)	TW520374B (fr)
UY (2)	UY25330A1 (fr)
WO (1)	WO1999035156A1 (fr)
YU (1)	YU41500A (fr)
ZA (1)	ZA9811939B (fr)

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.
US6043227A (en) *	1998-08-19	2000-03-28	Pfizer Inc.	C11 carbamates of macrolide antibacterials
EP1437360A3 (fr) *	1998-08-19	2005-04-06	Pfizer Products Inc.	C11-carbamates des macrolides antibactériens
EP1754700A3 (fr)	1999-01-27	2007-05-09	Kosan Biosciences, Inc.	synthese de polycetides
US6399582B1 (en)	1999-04-16	2002-06-04	Ortho-Mcneil Pharmaceutical, Inc.	Ketolide antibacterials
US6451768B1 (en)	1999-04-16	2002-09-17	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6590083B1 (en)	1999-04-16	2003-07-08	Ortho-Mcneil Pharmaceutical, Inc.	Ketolide antibacterials
EE200100613A (et)	1999-05-24	2003-02-17	Pfizer Products Inc.	13-metüülerütromütsiini derivaadid
WO2003072589A1 (fr) *	2002-02-26	2003-09-04	Meiji Seika Kaisha, Ltd.	Nouveau compose azalide cyclique a 15 chainons, nouveau derive diazalide cyclique a 16 chainons et procede de production de ceux-ci
DE602005009381D1 (de)	2004-09-23	2008-10-09	Schering Plough Ltd	Bekämpfung von parasiten in tieren durch verwendung neuer trifluormethansulfonanilidoximetherderivate
JP4750126B2 (ja) *	2004-11-19	2011-08-17	シェーリング−プラウ・リミテッド	殺寄生虫薬２−フェニル−３−（１ｈ−ピロール−２−イル）アクリロニトリル誘導体の使用による動物における寄生虫の制御
SI1836211T1 (sl)	2004-12-21	2010-04-30	Pfizer Prod Inc	Makrolidi
EP1890547A2 (fr) *	2005-06-09	2008-02-27	Schering-Plough Ltd.	Controle de parasites chez des animaux a l'aide de derives de n-[(phenyloxy)phenyl]-1,1,1-trifluoromethanesulfonamide et de n-[(phenylsulfanyl)phenyl]-1,1,1-trifluoromethanesulfonamide
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
CN101605756A (zh) *	2006-12-13	2009-12-16	先灵-普劳有限公司	氟苯尼考及其类似物的水溶性前药
WO2008076256A1 (fr) *	2006-12-13	2008-06-26	Schering-Plough Ltd.	Promédicaments solubles dans l'eau de chloramphénicol, thiamphénicol et analogues de ceux-ci
TWI430995B (zh)	2007-06-26	2014-03-21	Du Pont	萘異唑啉無脊椎有害動物控制劑
DK2182945T3 (en)	2007-06-27	2015-11-16	Du Pont	PROCEDURE TO COMBAT PESTS WITH ANIMALS
US20090131343A1 (en) *	2007-11-15	2009-05-21	Ly Tam Phan	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
WO2010014566A2 (fr) *	2008-07-30	2010-02-04	Intervet International B.V.	Procédé de préparation de composés aminodiol d'oxazoline protégés utiles comme produits intermédiaires dans la production de florfénicol
AU2010279587A1 (en)	2009-08-05	2012-02-09	E. I. Du Pont De Nemours And Company	Mesoionic pesticides
UA110924C2 (uk)	2009-08-05	2016-03-10	Е. І. Дю Пон Де Немур Енд Компані	Мезоіонні пестициди
UA107804C2 (xx)	2009-08-05	2015-02-25	Du Pont	Суміші мезоіонних пестицидів
EP2461684A2 (fr)	2009-08-05	2012-06-13	E. I. du Pont de Nemours and Company	Pesticides mésoioniques
EP2576523B1 (fr)	2010-05-27	2016-01-13	E. I. du Pont de Nemours and Company	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 (fr)	2010-12-20	2012-06-28	E.I. Du Pont De Nemours And Company	Composés de pyridine et de pyrimidine utilisés pour lutter contre des nuisibles invertébrés
EP2671887A4 (fr) *	2011-01-31	2014-06-25	Meiji Seika Pharma Co Ltd	Nouveau dérivé macrolide
US20140113934A1 (en)	2011-06-20	2014-04-24	E I Du Pont De Nemours And Company	Heterocyclic compounds for treating helminth infections
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
JP2015502936A (ja)	2011-11-28	2015-01-29	イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．ＤｕＰｏｎｔＤｅＮｅｍｏｕｒｓＡｎｄＣｏｍｐａｎｙ	スルホンアミド駆虫薬
WO2013158422A1 (fr)	2012-04-17	2013-10-24	E. I. Du Pont De Nemours And Company	Composés hétérocycliques pour la lutte contre des animaux nuisibles invertébrés
WO2014099837A1 (fr)	2012-12-18	2014-06-26	E. I. Du Pont De Nemours And Company	Sulfonamide anti-helminthique
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
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

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
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
US5824513A (en) *	1991-01-17	1998-10-20	Abbott Laboratories	Recombinant DNA method for producing erythromycin analogs
WO1993013663A1 (fr)	1992-01-17	1993-07-22	Abbott Laboratories	Procede permettant d'effectuer la biosynthese de polycetides specifiques
US5985844A (en) *	1992-03-26	1999-11-16	Merck & Co., Inc.	Homoerythromycin A derivatives modified at the 4"-and 8A-positions
CA2065218A1 (fr)	1991-04-11	1992-10-12	Robert R. Wilkening	Procede d'obtention de 9-desoxo-8a-aza-8a-homoerythromycine a et de ses derives 8a-alkyle
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 (fr) *	1997-05-09	1998-11-19	Pfizer Products Inc.	Derives d'erythromycine
HN1998000086A (es) *	1997-06-11	1999-03-08	Pfizer Prod Inc	Derivados de 9 - desofo - 9 aza - 9a - homoeritromicina a - 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
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
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
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
EE200100245A (et) *	1998-11-03	2002-10-15	Pfizer Products Inc.	Uued makroliidsed antibiootikumid
UA70972C2 (uk) *	1998-11-20	2004-11-15	Пфайзер Продактс Інк.	13-членні азаліди і їх застосування як антибіотиків
EE200100613A (et)	1999-05-24	2003-02-17	Pfizer Products Inc.	13-metüülerütromütsiini derivaadid
EP1101769A3 (fr) *	1999-11-18	2001-10-24	Pfizer Products Inc.	Dérivés de l'érythromycine contenant de l'azote
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 PL PL98341642A patent/PL341642A1/xx unknown
- 1998-12-21 BR BR9814601-7A patent/BR9814601A/pt not_active IP Right Cessation
- 1998-12-21 US US09/554,988 patent/US6472371B1/en not_active Expired - Fee Related
- 1998-12-21 EP EP98958384A patent/EP1044207A1/fr not_active Withdrawn
- 1998-12-21 AU AU14447/99A patent/AU756409B2/en not_active Ceased
- 1998-12-21 KR KR1020007007313A patent/KR100352809B1/ko not_active Expired - Fee Related
- 1998-12-21 CZ CZ20002458A patent/CZ20002458A3/cs unknown
- 1998-12-21 IL IL13702498A patent/IL137024A0/xx unknown
- 1998-12-21 YU YU41500A patent/YU41500A/sh unknown
- 1998-12-21 HU HU0100420A patent/HUP0100420A3/hu unknown
- 1998-12-21 WO PCT/IB1998/002099 patent/WO1999035156A1/fr not_active Ceased
- 1998-12-21 SK SK978-2000A patent/SK9782000A3/sk unknown
- 1998-12-21 CA CA002316919A patent/CA2316919C/fr not_active Expired - Fee Related
- 1998-12-21 NZ NZ504986A patent/NZ504986A/xx unknown
- 1998-12-21 CN CN98813253A patent/CN1284081A/zh active Pending
- 1998-12-21 HR HR20000442A patent/HRP20000442A2/hr not_active Application Discontinuation
- 1998-12-21 JP JP2000527552A patent/JP2002500230A/ja active Pending
- 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 MA MA25407A patent/MA24729A1/fr unknown
- 1998-12-30 TN TNTNSN98238A patent/TNSN98238A1/fr unknown
- 1998-12-30 UY UY25330A patent/UY25330A1/es not_active Application Discontinuation
- 1998-12-30 DZ DZ980308A patent/DZ2698A1/fr active
- 1998-12-30 ZA ZA9811939A patent/ZA9811939B/xx 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 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
AP9801420A0 (en)	1998-12-31
NZ504986A (en)	2003-03-28
CA2316919A1 (fr)	1999-07-15
UY25330A1 (es)	2000-12-29
HRP20000442A2 (en)	2001-04-30
GT199800206A (es)	2000-06-21
US6472371B1 (en)	2002-10-29
ZA9811939B (en)	2000-06-30
PE20000049A1 (es)	2000-02-07
BR9814601A (pt)	2000-10-17
UY25574A1 (es)	1999-09-27
CO4970821A1 (es)	2000-11-07
WO1999035156A1 (fr)	1999-07-15
HUP0100420A2 (hu)	2001-07-30
AR014948A1 (es)	2001-04-11
AR020551A2 (es)	2002-05-15
KR20010024818A (ko)	2001-03-26
KR100352809B1 (ko)	2002-11-01
US20040092459A1 (en)	2004-05-13
NO20003347D0 (no)	2000-06-27
TNSN98238A1 (fr)	2005-03-15
PA8465301A1 (es)	2000-09-29
JP2002500230A (ja)	2002-01-08
BG104644A (en)	2001-01-31
CZ20002458A3 (cs)	2001-10-17
AR020851A2 (es)	2002-05-29
YU41500A (sh)	2003-02-28
TW520374B (en)	2003-02-11
AR019787A2 (es)	2002-03-13
CN1284081A (zh)	2001-02-14
PL341642A1 (en)	2001-04-23
MA24729A1 (fr)	1999-07-01
WO1999035156B1 (fr)	1999-10-21
SK9782000A3 (en)	2001-12-03
NO20003347L (no)	2000-08-28
CA2316919C (fr)	2004-10-26
EA200000594A1 (ru)	2001-04-23
DZ2698A1 (fr)	2003-03-29
IL137024A0 (en)	2001-06-14
AU756409B2 (en)	2003-01-09
AU1444799A (en)	1999-07-26
EP1044207A1 (fr)	2000-10-18
HUP0100420A3 (en)	2003-07-28
IS5528A (is)	2000-06-09
US7015203B2 (en)	2006-03-21

Publication	Publication Date	Title
US7015203B2 (en)	2006-03-21	Macrolides
AU759019B2 (en)	2003-04-03	Novel erythromycin derivatives
US6777543B2 (en)	2004-08-17	13-methyl erythromycin derivatives
CA2351429C (fr)	2005-07-12	Azalides a 13 elements et leur utilisation en tant qu'antibiotiques
EP0988310A1 (fr)	2000-03-29	Derives de homo-erythromycine -9-deoxo-9a-aza-9aa substitution en position 4
CA2293335A1 (fr)	1998-12-17	Derives de 9-oxime erythromycine
AU5995299A (en)	2000-05-22	Novel macrolide antibiotics
EP0992509B1 (fr)	2004-09-22	Nouveaux dérivés macrolides
EP0984019B1 (fr)	2004-06-02	C11-carbamates des macrolides antibactériens
US6162794A (en)	2000-12-19	Erythromycin derivatives
US20020151507A1 (en)	2002-10-17	9-oxime erythromycin derivatives
WO1999062920A1 (fr)	1999-12-09	Derives 3-keto tricycliques de 6-o-methylerythromycine
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