JP2006528668A - 新規１４−及び１５−員環マクロライド - Google Patents
新規１４−及び１５−員環マクロライド Download PDFInfo
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- JP2006528668A JP2006528668A JP2006529797A JP2006529797A JP2006528668A JP 2006528668 A JP2006528668 A JP 2006528668A JP 2006529797 A JP2006529797 A JP 2006529797A JP 2006529797 A JP2006529797 A JP 2006529797A JP 2006528668 A JP2006528668 A JP 2006528668A
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- Prior art keywords
- alkyl
- hydrogen
- optionally substituted
- compound
- formula
- Prior art date
- Legal status (The legal status 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 status listed.)
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- 239000003120 macrolide antibiotic agent Substances 0.000 title abstract description 9
- 229940041033 macrolides Drugs 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 31
- 208000015181 infectious disease Diseases 0.000 claims abstract description 7
- 230000000813 microbial effect Effects 0.000 claims abstract description 7
- 230000002265 prevention Effects 0.000 claims abstract description 7
- 241001465754 Metazoa Species 0.000 claims abstract description 6
- 238000002560 therapeutic procedure Methods 0.000 claims abstract description 6
- 230000009885 systemic effect Effects 0.000 claims abstract description 5
- 230000008569 process Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 155
- 125000000217 alkyl group Chemical group 0.000 claims description 80
- 239000001257 hydrogen Substances 0.000 claims description 68
- 229910052739 hydrogen Inorganic materials 0.000 claims description 68
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 54
- -1 cyano, phenyl Chemical group 0.000 claims description 52
- 239000003814 drug Substances 0.000 claims description 33
- 125000000623 heterocyclic group Chemical group 0.000 claims description 32
- 125000003545 alkoxy group Chemical group 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 20
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 14
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 13
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- 239000003085 diluting agent Substances 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 125000004429 atom Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 9
- 229910052770 Uranium Inorganic materials 0.000 claims description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Chemical group 0.000 claims description 5
- 239000011593 sulfur Chemical group 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000004001 thioalkyl group Chemical group 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 2
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 4
- 239000000543 intermediate Substances 0.000 description 60
- 239000000203 mixture Substances 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 43
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 38
- 239000000243 solution Substances 0.000 description 35
- 150000003839 salts Chemical class 0.000 description 27
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000011541 reaction mixture Substances 0.000 description 21
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- 239000012043 crude product Substances 0.000 description 13
- 230000002829 reductive effect Effects 0.000 description 13
- 238000009472 formulation Methods 0.000 description 12
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 229940079593 drug Drugs 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- 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 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- 238000005160 1H NMR spectroscopy Methods 0.000 description 8
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin 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@@](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 description 8
- 150000002148 esters Chemical class 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 229960004099 azithromycin Drugs 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000002585 base Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 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 5
- 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 5
- 229920002472 Starch Polymers 0.000 description 5
- 241000193996 Streptococcus pyogenes Species 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 238000002347 injection Methods 0.000 description 5
- 239000007924 injection Substances 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 4
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 239000003086 colorant Substances 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- 239000003937 drug carrier Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229960003276 erythromycin Drugs 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 238000001727 in vivo Methods 0.000 description 4
- 238000007918 intramuscular administration Methods 0.000 description 4
- 238000007913 intrathecal administration Methods 0.000 description 4
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007922 nasal spray Substances 0.000 description 4
- 239000002674 ointment Substances 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 238000007920 subcutaneous administration Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000000375 suspending agent Substances 0.000 description 4
- 229940124597 therapeutic agent Drugs 0.000 description 4
- 238000011200 topical administration Methods 0.000 description 4
- ODOFTUIHVVTJRI-UHFFFAOYSA-N 7-(2-aminoethylamino)-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C(O)=O)C(=O)C=2C=C(F)C(NCCN)=CC=2N1C1CC1 ODOFTUIHVVTJRI-UHFFFAOYSA-N 0.000 description 3
- ISPVACVJFUIDPD-UHFFFAOYSA-N 7-chloro-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 ISPVACVJFUIDPD-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 0 CN=CC=NCCC(N1C=CCIC)=C(*)C=C(*=C)C1=O Chemical compound CN=CC=NCCC(N1C=CCIC)=C(*)C=C(*=C)C1=O 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000606768 Haemophilus influenzae Species 0.000 description 3
- 241000588655 Moraxella catarrhalis Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
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- 239000000010 aprotic solvent Substances 0.000 description 3
- CELPHAGZKFMOMR-UHFFFAOYSA-N azanium;dichloromethane;methanol;hydroxide Chemical compound [NH4+].[OH-].OC.ClCCl CELPHAGZKFMOMR-UHFFFAOYSA-N 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- 229940097362 cyclodextrins Drugs 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- 244000000010 microbial pathogen Species 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 150000007530 organic bases Chemical class 0.000 description 3
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 3
- 238000007911 parenteral administration Methods 0.000 description 3
- 229910003446 platinum oxide Inorganic materials 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 125000003396 thiol group Chemical group [H]S* 0.000 description 3
- 230000000699 topical effect Effects 0.000 description 3
- 125000004605 1,2,3,4-tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 2
- RIAJQFIZKHZWMP-UHFFFAOYSA-N 2-(furan-2-yl)pyridine Chemical compound C1=COC(C=2N=CC=CC=2)=C1 RIAJQFIZKHZWMP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
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- 241000943303 Enterococcus faecalis ATCC 29212 Species 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 2
- 108010010803 Gelatin Proteins 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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 241000193998 Streptococcus pneumoniae Species 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 2
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 238000006114 decarboxylation reaction Methods 0.000 description 2
- 239000007933 dermal patch Substances 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000037406 food intake Effects 0.000 description 2
- 238000001640 fractional crystallisation Methods 0.000 description 2
- 125000002541 furyl group Chemical group 0.000 description 2
- 239000000499 gel Substances 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 2
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 2
- 239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
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Classifications
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- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0310992.3A GB0310992D0 (en) | 2003-05-13 | 2003-05-13 | Novel compounds |
| PCT/EP2004/005086 WO2004101590A1 (en) | 2003-05-13 | 2004-05-11 | Novel 14 and 15 membered-ring compounds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006528668A true JP2006528668A (ja) | 2006-12-21 |
| JP2006528668A5 JP2006528668A5 (https=) | 2007-07-12 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2006529797A Pending JP2006528668A (ja) | 2003-05-13 | 2004-05-11 | 新規１４−及び１５−員環マクロライド |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20080221158A1 (https=) |
| EP (1) | EP1633765B1 (https=) |
| JP (1) | JP2006528668A (https=) |
| CN (1) | CN1820016A (https=) |
| AR (1) | AR044310A1 (https=) |
| AT (1) | ATE378347T1 (https=) |
| CA (1) | CA2525459A1 (https=) |
| CL (1) | CL2004001005A1 (https=) |
| DE (1) | DE602004010110T2 (https=) |
| ES (1) | ES2295865T3 (https=) |
| GB (1) | GB0310992D0 (https=) |
| WO (1) | WO2004101590A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2008540504A (ja) * | 2005-05-10 | 2008-11-20 | グラクソスミスクライン・イストラジヴァッキ・センタル・ザグレブ・ドルズバ・ゼー・オメイェノ・オドゴヴォルノスティオ | 細菌感染症の処置に有用な４’’アミノ結合マクロライド |
| GB201706299D0 (en) * | 2017-04-20 | 2017-06-07 | Novintum Biotechnology Gmbh | Compounds |
| WO2018193126A1 (en) * | 2017-04-20 | 2018-10-25 | Novintum Biotechnology Gmbh | Azithromycin derivatives containing a phosphonium ion as antibacterial agents |
| WO2021195126A1 (en) | 2020-03-24 | 2021-09-30 | Burnet Michael W | Anti-infective and anti-viral compounds and compositions |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5495585A (en) * | 1978-01-03 | 1979-07-28 | Pfizer | Oleandomycin*erythromycin and 4***deoxyy4*** alkyl amide derivative of erythromycin carbonate |
| JPS60231691A (ja) * | 1984-04-13 | 1985-11-18 | フアイザー・インコーポレーテツド | ９ａ‐アザ‐９ａ‐ホモエリスロマイシン誘導体 |
| WO1996034007A1 (es) * | 1995-04-27 | 1996-10-31 | Laboratorios Aranda, S.A. De C.V. | Derivados de quinolonilcarboxieritromicina y composiciones farmaceuticas que los contienen |
| JP2002502366A (ja) * | 1996-05-07 | 2002-01-22 | アボット・ラボラトリーズ | ３―デスクラジノース―２，３―無水エリスロマイシン誘導体 |
| JP2004511566A (ja) * | 2000-10-19 | 2004-04-15 | グラクソ グループ リミテッド | マイクロライド |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4518590A (en) * | 1984-04-13 | 1985-05-21 | Pfizer Inc. | 9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method |
-
2003
- 2003-05-13 GB GBGB0310992.3A patent/GB0310992D0/en not_active Ceased
-
2004
- 2004-05-11 AR ARP040101615A patent/AR044310A1/es not_active Application Discontinuation
- 2004-05-11 US US10/556,709 patent/US20080221158A1/en not_active Abandoned
- 2004-05-11 CL CL200401005A patent/CL2004001005A1/es unknown
- 2004-05-11 ES ES04732099T patent/ES2295865T3/es not_active Expired - Lifetime
- 2004-05-11 DE DE602004010110T patent/DE602004010110T2/de not_active Expired - Fee Related
- 2004-05-11 EP EP04732099A patent/EP1633765B1/en not_active Expired - Lifetime
- 2004-05-11 JP JP2006529797A patent/JP2006528668A/ja active Pending
- 2004-05-11 CA CA002525459A patent/CA2525459A1/en not_active Abandoned
- 2004-05-11 AT AT04732099T patent/ATE378347T1/de not_active IP Right Cessation
- 2004-05-11 CN CNA200480019644XA patent/CN1820016A/zh active Pending
- 2004-05-11 WO PCT/EP2004/005086 patent/WO2004101590A1/en not_active Ceased
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5495585A (en) * | 1978-01-03 | 1979-07-28 | Pfizer | Oleandomycin*erythromycin and 4***deoxyy4*** alkyl amide derivative of erythromycin carbonate |
| JPS60231691A (ja) * | 1984-04-13 | 1985-11-18 | フアイザー・インコーポレーテツド | ９ａ‐アザ‐９ａ‐ホモエリスロマイシン誘導体 |
| WO1996034007A1 (es) * | 1995-04-27 | 1996-10-31 | Laboratorios Aranda, S.A. De C.V. | Derivados de quinolonilcarboxieritromicina y composiciones farmaceuticas que los contienen |
| JP2002502366A (ja) * | 1996-05-07 | 2002-01-22 | アボット・ラボラトリーズ | ３―デスクラジノース―２，３―無水エリスロマイシン誘導体 |
| JP2004511566A (ja) * | 2000-10-19 | 2004-04-15 | グラクソ グループ リミテッド | マイクロライド |
Non-Patent Citations (1)
| Title |
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| JPN6010009167, Ｏｒｇ． Ｌｅｔｔ．， ２０００， ２ （１９）， ｐｐ ２９５１−２９５４ * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004010110T2 (de) | 2008-09-11 |
| EP1633765B1 (en) | 2007-11-14 |
| ES2295865T3 (es) | 2008-04-16 |
| ATE378347T1 (de) | 2007-11-15 |
| CA2525459A1 (en) | 2004-11-25 |
| US20080221158A1 (en) | 2008-09-11 |
| DE602004010110D1 (de) | 2007-12-27 |
| EP1633765A1 (en) | 2006-03-15 |
| AR044310A1 (es) | 2005-09-07 |
| CL2004001005A1 (es) | 2005-03-18 |
| CN1820016A (zh) | 2006-08-16 |
| GB0310992D0 (en) | 2003-06-18 |
| WO2004101590A1 (en) | 2004-11-25 |
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