GB2288174A - Erythromycin derivatives, processes for preparing them, pharmaceutical compositions containing them, and their use as medicaments - Google Patents
Erythromycin derivatives, processes for preparing them, pharmaceutical compositions containing them, and their use as medicaments Download PDFInfo
- Publication number
- GB2288174A GB2288174A GB9506856A GB9506856A GB2288174A GB 2288174 A GB2288174 A GB 2288174A GB 9506856 A GB9506856 A GB 9506856A GB 9506856 A GB9506856 A GB 9506856A GB 2288174 A GB2288174 A GB 2288174A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- processes
- addition salts
- radical
- hydrogen atom
- 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.)
- Withdrawn
Links
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title claims description 80
- 238000000034 method Methods 0.000 title claims description 32
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 13
- 239000003814 drug Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 54
- -1 oxycarbonyl (2-(3-(4quinolinyl) 2-propyl) hydrazono) Chemical class 0.000 claims description 41
- 239000002253 acid Substances 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 33
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 31
- 229960003276 erythromycin Drugs 0.000 claims description 31
- 238000002360 preparation method Methods 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 231100000252 nontoxic Toxicity 0.000 claims description 8
- 230000003000 nontoxic effect Effects 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 150000007513 acids Chemical class 0.000 claims description 7
- 239000003638 chemical reducing agent Substances 0.000 claims description 6
- 125000000524 functional group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 229960001760 dimethyl sulfoxide Drugs 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 208000015181 infectious disease Diseases 0.000 claims description 5
- 244000005700 microbiome Species 0.000 claims description 5
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 5
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 230000003115 biocidal effect Effects 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052763 palladium Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 3
- 229910017852 NH2NH2 Inorganic materials 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000012374 esterification agent Substances 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000000047 product Substances 0.000 description 120
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- 239000000377 silicon dioxide Substances 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 238000013019 agitation Methods 0.000 description 23
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 17
- 238000000605 extraction Methods 0.000 description 16
- 238000001704 evaporation Methods 0.000 description 14
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 14
- 238000001914 filtration Methods 0.000 description 13
- 238000005406 washing Methods 0.000 description 13
- 101150041968 CDC13 gene Proteins 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 12
- 238000001035 drying Methods 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 239000012429 reaction media Substances 0.000 description 8
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
- 125000005638 hydrazono group Chemical group 0.000 description 7
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 150000001299 aldehydes Chemical class 0.000 description 6
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
- 239000002674 ointment Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
- MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 4
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- JJMTYUUFWCZEAA-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)propanal Chemical compound O=CCCC1=NC=CN1 JJMTYUUFWCZEAA-UHFFFAOYSA-N 0.000 description 3
- KECFNYKLSNPOOB-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanal Chemical compound O1C(CCC=O)=NC(C=2C=CC=CC=2)=N1 KECFNYKLSNPOOB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 241000191967 Staphylococcus aureus Species 0.000 description 3
- 241000194017 Streptococcus Species 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 150000005840 aryl radicals Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 230000001419 dependent effect Effects 0.000 description 3
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 3
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 3
- CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 3
- GTJNQHWEJNBLLS-UHFFFAOYSA-N n,n-diethylethanamine;methanol;2-propan-2-yloxypropane Chemical compound OC.CCN(CC)CC.CC(C)OC(C)C GTJNQHWEJNBLLS-UHFFFAOYSA-N 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 3
- ALQUTEKNDPODSS-UHFFFAOYSA-N quinoline-4-carbaldehyde-oxime Natural products C1=CC=C2C(C=NO)=CC=NC2=C1 ALQUTEKNDPODSS-UHFFFAOYSA-N 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- GGZQLTVZPOGLCC-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dioxolane Chemical compound BrCCC1OCCO1 GGZQLTVZPOGLCC-UHFFFAOYSA-N 0.000 description 2
- CGQLWWXAVSIXPY-UHFFFAOYSA-N 3-(1,3-thiazol-4-yl)propanal Chemical compound O=CCCC1=CSC=N1 CGQLWWXAVSIXPY-UHFFFAOYSA-N 0.000 description 2
- GCADRZXDZQALMW-UHFFFAOYSA-N 3-(2-chlorophenyl)propanal Chemical compound ClC1=CC=CC=C1CCC=O GCADRZXDZQALMW-UHFFFAOYSA-N 0.000 description 2
- FYUUJKZXEUGJFF-UHFFFAOYSA-N 3-(2-phenyl-1,3-thiazol-5-yl)propanal Chemical compound S1C(CCC=O)=CN=C1C1=CC=CC=C1 FYUUJKZXEUGJFF-UHFFFAOYSA-N 0.000 description 2
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000193985 Streptococcus agalactiae Species 0.000 description 2
- 241000193998 Streptococcus pneumoniae Species 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- PKSROMPNLONTJT-UHFFFAOYSA-N azanium;chloroform;methanol;hydroxide Chemical compound N.O.OC.ClC(Cl)Cl PKSROMPNLONTJT-UHFFFAOYSA-N 0.000 description 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
- 229940047650 haemophilus influenzae Drugs 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 239000007943 implant Substances 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000010561 standard procedure Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical class CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 description 1
- ULZXQMNYOKEVHM-UHFFFAOYSA-N 1-quinolin-4-ylprop-1-en-1-ol Chemical compound N1=CC=C(C2=CC=CC=C12)C(=CC)O ULZXQMNYOKEVHM-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VROMJSDIQMATBP-UHFFFAOYSA-N 2-(2-chlorophenyl)propanal Chemical compound O=CC(C)C1=CC=CC=C1Cl VROMJSDIQMATBP-UHFFFAOYSA-N 0.000 description 1
- AEJOSDWQCPXZCC-UHFFFAOYSA-N 2-(2-pyridin-3-yl-1,3-thiazol-4-yl)propanal Chemical compound O=CC(C)C1=CSC(C=2C=NC=CC=2)=N1 AEJOSDWQCPXZCC-UHFFFAOYSA-N 0.000 description 1
- CQCAYWAIRTVXIY-UHFFFAOYSA-N 2-(triphenyl-$l^{5}-phosphanylidene)acetaldehyde Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC=O)C1=CC=CC=C1 CQCAYWAIRTVXIY-UHFFFAOYSA-N 0.000 description 1
- WEBRDDDJKLAXTO-UHFFFAOYSA-N 2-ethyl-1,3-dioxolane Chemical compound CCC1OCCO1 WEBRDDDJKLAXTO-UHFFFAOYSA-N 0.000 description 1
- KKALNCQCDXQTCG-UHFFFAOYSA-N 2-phenyl-1,3-thiazole-5-carbaldehyde Chemical compound S1C(C=O)=CN=C1C1=CC=CC=C1 KKALNCQCDXQTCG-UHFFFAOYSA-N 0.000 description 1
- LCALUFNLWHYTKX-UHFFFAOYSA-N 2-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1C1=CC=CC=C1 LCALUFNLWHYTKX-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- ACVSHQGHCWUJFU-UHFFFAOYSA-N 2h-imidazole Chemical compound C1N=CC=N1 ACVSHQGHCWUJFU-UHFFFAOYSA-N 0.000 description 1
- RROVHEOLZYPASG-UHFFFAOYSA-N 3-(2-chlorophenyl)propan-1-ol Chemical compound OCCCC1=CC=CC=C1Cl RROVHEOLZYPASG-UHFFFAOYSA-N 0.000 description 1
- XPEPGYKUHRYQCN-UHFFFAOYSA-N 3-(2-phenyl-1,3-thiazol-5-yl)prop-1-en-1-ol Chemical compound S1C(CC=CO)=CN=C1C1=CC=CC=C1 XPEPGYKUHRYQCN-UHFFFAOYSA-N 0.000 description 1
- ZEOGQSZSRIWDGS-UHFFFAOYSA-N 3-(2-phenyl-1,3-thiazol-5-yl)prop-2-enal Chemical compound S1C(C=CC=O)=CN=C1C1=CC=CC=C1 ZEOGQSZSRIWDGS-UHFFFAOYSA-N 0.000 description 1
- PLWFIWIDCXDJQK-UHFFFAOYSA-N 3-(2-phenyl-1,3-thiazol-5-yl)propan-1-ol Chemical compound S1C(CCCO)=CN=C1C1=CC=CC=C1 PLWFIWIDCXDJQK-UHFFFAOYSA-N 0.000 description 1
- CIXUYXVINYQKCI-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propan-1-ol Chemical compound O1C(CCCO)=NC(C=2C=CC=CC=2)=N1 CIXUYXVINYQKCI-UHFFFAOYSA-N 0.000 description 1
- UBSBRLFVQKHLPG-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanoic acid Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=N1 UBSBRLFVQKHLPG-UHFFFAOYSA-N 0.000 description 1
- OFHHZDFJRSDUKD-UHFFFAOYSA-N 4-[2-(1,3-dioxolan-2-yl)ethenyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound O1CCOC1C=CC1=CSC(C=2C=NC=CC=2)=N1 OFHHZDFJRSDUKD-UHFFFAOYSA-N 0.000 description 1
- WOOCEWIQJOOXIU-UHFFFAOYSA-N 4-[2-(1,3-dioxolan-2-yl)ethenyl]-7-methoxyquinoline Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1C=CC1OCCO1 WOOCEWIQJOOXIU-UHFFFAOYSA-N 0.000 description 1
- BOFDARFQPKOZFZ-UHFFFAOYSA-N 4-[2-(1,3-dioxolan-2-yl)ethenyl]quinoline Chemical compound O1CCOC1C=CC1=CC=NC2=CC=CC=C12 BOFDARFQPKOZFZ-UHFFFAOYSA-N 0.000 description 1
- YZAWVTDWFMSRCI-UHFFFAOYSA-N 4-[2-(1,3-dioxolan-2-yl)ethyl]-2-pyridin-3-yl-1,3-thiazole Chemical compound O1CCOC1CCC(N=1)=CSC=1C1=CC=CN=C1 YZAWVTDWFMSRCI-UHFFFAOYSA-N 0.000 description 1
- ZYXNAQRXUFIBIF-UHFFFAOYSA-N 4-[2-(1,3-dioxolan-2-yl)ethyl]quinoline Chemical compound C=1C=NC2=CC=CC=C2C=1CCC1OCCO1 ZYXNAQRXUFIBIF-UHFFFAOYSA-N 0.000 description 1
- VSTRESXSGAUGKC-UHFFFAOYSA-N 4H-benzimidazole Chemical compound C1C=CC=C2N=CN=C12 VSTRESXSGAUGKC-UHFFFAOYSA-N 0.000 description 1
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 1
- WFQQOWDFMDPMQL-UHFFFAOYSA-N 5h-benzimidazole Chemical compound C1C=CC2=NC=NC2=C1 WFQQOWDFMDPMQL-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 101100495912 Arabidopsis thaliana CHR12 gene Proteins 0.000 description 1
- 241000193738 Bacillus anthracis Species 0.000 description 1
- 206010006500 Brucellosis Diseases 0.000 description 1
- HZKWFGNZINUNOQ-UHFFFAOYSA-N C(C=C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 Chemical compound C(C=C)=O.C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1 HZKWFGNZINUNOQ-UHFFFAOYSA-N 0.000 description 1
- 101100087530 Caenorhabditis elegans rom-1 gene Proteins 0.000 description 1
- 206010007882 Cellulitis Diseases 0.000 description 1
- 241000606161 Chlamydia Species 0.000 description 1
- FVIGODVHAVLZOO-UHFFFAOYSA-N Dixanthogen Chemical compound CCOC(=S)SSC(=S)OCC FVIGODVHAVLZOO-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000194032 Enterococcus faecalis Species 0.000 description 1
- 241000194031 Enterococcus faecium Species 0.000 description 1
- 201000000297 Erysipelas Diseases 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 101001035601 Homo sapiens Huntingtin-associated protein 1 Proteins 0.000 description 1
- 102100039384 Huntingtin-associated protein 1 Human genes 0.000 description 1
- 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 1
- 241000589248 Legionella Species 0.000 description 1
- 208000007764 Legionnaires' Disease Diseases 0.000 description 1
- 208000032376 Lung infection Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 101100305983 Mus musculus Rom1 gene Proteins 0.000 description 1
- 241000186359 Mycobacterium Species 0.000 description 1
- 241000202934 Mycoplasma pneumoniae Species 0.000 description 1
- 208000005141 Otitis Diseases 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- 208000035109 Pneumococcal Infections Diseases 0.000 description 1
- 206010035664 Pneumonia Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
- 241000606701 Rickettsia Species 0.000 description 1
- 206010039587 Scarlet Fever Diseases 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 206010056430 Staphylococcal sepsis Diseases 0.000 description 1
- 241000191963 Staphylococcus epidermidis Species 0.000 description 1
- 206010061372 Streptococcal infection Diseases 0.000 description 1
- 241001134658 Streptococcus mitis Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- QIOZLISABUUKJY-UHFFFAOYSA-N Thiobenzamide Chemical compound NC(=S)C1=CC=CC=C1 QIOZLISABUUKJY-UHFFFAOYSA-N 0.000 description 1
- 241000223996 Toxoplasma Species 0.000 description 1
- 241000202898 Ureaplasma Species 0.000 description 1
- 241000588902 Zymomonas mobilis Species 0.000 description 1
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000008135 aqueous vehicle Substances 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- AZWXAPCAJCYGIA-UHFFFAOYSA-N bis(2-methylpropyl)alumane Chemical compound CC(C)C[AlH]CC(C)C AZWXAPCAJCYGIA-UHFFFAOYSA-N 0.000 description 1
- 210000001124 body fluid Anatomy 0.000 description 1
- 239000010839 body fluid Substances 0.000 description 1
- MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 229910000024 caesium carbonate Inorganic materials 0.000 description 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical compound [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 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 description 1
- SIPUZPBQZHNSDW-UHFFFAOYSA-N diisobutylaluminium hydride Substances CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 206010013023 diphtheria Diseases 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 208000019258 ear infection Diseases 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- ROKNTXACUCMRQU-UHFFFAOYSA-N ethyl 2-phenyl-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OCC)=CN=C1C1=CC=CC=C1 ROKNTXACUCMRQU-UHFFFAOYSA-N 0.000 description 1
- MHYCRLGKOZWVEF-UHFFFAOYSA-N ethyl acetate;hydrate Chemical compound O.CCOC(C)=O MHYCRLGKOZWVEF-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000004005 formimidoyl group Chemical group [H]\N=C(/[H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000006194 liquid suspension Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- IZDROVVXIHRYMH-UHFFFAOYSA-N methanesulfonic anhydride Chemical compound CS(=O)(=O)OS(C)(=O)=O IZDROVVXIHRYMH-UHFFFAOYSA-N 0.000 description 1
- RHMQNXNXUZLEIY-UHFFFAOYSA-N methanol;2-propan-2-yloxypropane Chemical compound OC.CC(C)OC(C)C RHMQNXNXUZLEIY-UHFFFAOYSA-N 0.000 description 1
- RRDBEPHWFIYCQH-UHFFFAOYSA-N methyl 2-phenyl-1,3-thiazole-5-carboxylate Chemical compound S1C(C(=O)OC)=CN=C1C1=CC=CC=C1 RRDBEPHWFIYCQH-UHFFFAOYSA-N 0.000 description 1
- SKAIVXBBFBJQOL-UHFFFAOYSA-N methyl 3-(2-chlorophenyl)propanoate Chemical compound COC(=O)CCC1=CC=CC=C1Cl SKAIVXBBFBJQOL-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- FKSLYSSVKFYJKE-UHFFFAOYSA-N n,n-diethylethanamine;methanol Chemical compound OC.CCN(CC)CC FKSLYSSVKFYJKE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 230000000050 nutritive effect Effects 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940023488 pill Drugs 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
- 239000001472 potassium tartrate Substances 0.000 description 1
- 229940111695 potassium tartrate Drugs 0.000 description 1
- 235000011005 potassium tartrates Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000004621 quinuclidinyl group Chemical group N12C(CC(CC1)CC2)* 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- HELHAJAZNSDZJO-OLXYHTOASA-L sodium L-tartrate Chemical compound [Na+].[Na+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O HELHAJAZNSDZJO-OLXYHTOASA-L 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001476 sodium potassium tartrate Substances 0.000 description 1
- 235000011006 sodium potassium tartrate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000001433 sodium tartrate Substances 0.000 description 1
- 229960002167 sodium tartrate Drugs 0.000 description 1
- 235000011004 sodium tartrates Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 229940098466 sublingual tablet Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000007940 sugar coated tablet Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- CMSYDJVRTHCWFP-UHFFFAOYSA-N triphenylphosphane;hydrobromide Chemical compound Br.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 CMSYDJVRTHCWFP-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- 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
-
- 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)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9404154A FR2718450B1 (fr) | 1994-04-08 | 1994-04-08 | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB9506856D0 GB9506856D0 (en) | 1995-05-24 |
| GB2288174A true GB2288174A (en) | 1995-10-11 |
Family
ID=9461886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9506856A Withdrawn GB2288174A (en) | 1994-04-08 | 1995-04-03 | Erythromycin derivatives, processes for preparing them, pharmaceutical compositions containing them, and their use as medicaments |
Country Status (49)
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5747467A (en) * | 1995-12-22 | 1998-05-05 | Roussel Uclaf | Erythromycins |
| WO1998056800A1 (en) * | 1997-06-11 | 1998-12-17 | Pfizer Products Inc. | 9-oxime erythromycin derivatives |
| WO2000017218A1 (en) * | 1998-09-22 | 2000-03-30 | Pfizer Products Inc. | Carbamate and carbazate ketolide antibiotics |
| FR2786188A1 (fr) * | 1998-11-24 | 2000-05-26 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
Families Citing this family (46)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2732023B1 (fr) * | 1995-03-22 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2745289B1 (fr) * | 1996-02-28 | 1998-05-29 | Roussel Uclaf | Nouveaux derives de l'acide 1(2h) quinoleine carboxylique, leur procede de preparation et leur application a la synthese de produits doues de proprietes antibiotiques |
| US5750510A (en) * | 1997-04-04 | 1998-05-12 | Abbott Laboratories | 3-descladinose-2,3-anhydroerythromycin derivatives |
| DE69723848T2 (de) * | 1996-05-07 | 2004-07-01 | Abbott Laboratories, Abbott Park | 3-descladinose-2,3-anhydroerythromycin-derivate |
| FR2748746B1 (fr) * | 1996-05-14 | 1998-08-14 | Hoechst Marion Roussel Inc | Nouveau procede d'isomerisation du radical methyle en 10 de derives de l'erythromycine |
| FR2751656B1 (fr) * | 1996-07-24 | 1998-10-16 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| UA51730C2 (uk) * | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| DE69733439T2 (de) * | 1996-09-04 | 2006-05-04 | Abbott Laboratories, Abbott Park | 6-o-Substituierte Ketoliden mit antibakteriellen Wirkung |
| FR2757168B1 (fr) * | 1996-12-12 | 1999-06-11 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2760017B1 (fr) * | 1997-02-27 | 1999-04-30 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erytromycine, leur procede de preparation et leur application comme medicaments |
| AU4472897A (en) * | 1997-03-10 | 1998-09-29 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| AU6421398A (en) * | 1997-03-24 | 1998-10-20 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| WO1998051696A1 (en) * | 1997-05-09 | 1998-11-19 | Pfizer Products Inc. | Erythromycin derivatives |
| US5922683A (en) * | 1997-05-29 | 1999-07-13 | Abbott Laboratories | Multicyclic erythromycin derivatives |
| FR2771008B1 (fr) * | 1997-11-17 | 2000-04-28 | Hoechst Marion Roussel Inc | Utilisation des ketolides pour la preparation de compositions pharmaceutiques destinees a prevenir les complications thrombotiques arterielles liees a l'atherosclerose |
| AP1060A (en) * | 1998-01-02 | 2002-04-23 | Pfizer Prod Inc | Novel erythromycin derivatives. |
| HRP980189B1 (en) * | 1998-04-06 | 2004-04-30 | Pliva Pharm & Chem Works | Novel 15-membered lactams ketolides |
| EP1298138B1 (en) * | 1998-12-10 | 2006-11-02 | Pfizer Products Inc. | Carbamate and Carbazate Ketolide Antibiotics |
| EP1749832A3 (en) * | 1998-12-10 | 2008-03-26 | Pfizer Products Incorporated | Carbamate and carbazate ketolide antibiotics |
| ATE344269T1 (de) | 1998-12-10 | 2006-11-15 | Pfizer Prod Inc | Carbamat und carbazat ketolid antibiotika |
| FR2789392B1 (fr) * | 1999-02-04 | 2001-10-05 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| US6399582B1 (en) | 1999-04-16 | 2002-06-04 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| US6590083B1 (en) | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| AU775637B2 (en) * | 1999-04-16 | 2004-08-12 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| EE200100613A (et) * | 1999-05-24 | 2003-02-17 | Pfizer Products Inc. | 13-metüülerütromütsiini derivaadid |
| WO2003004509A2 (en) * | 2001-07-03 | 2003-01-16 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
| US7332304B2 (en) | 2002-07-01 | 2008-02-19 | Arkion Life Sciences Llc | Process and materials for production of glucosamine and N-acetylglucosamine |
| US7601695B2 (en) * | 2003-03-10 | 2009-10-13 | Optimer Pharmaceuticals, Inc. | Antibacterial agents |
| EP1618120A2 (en) * | 2003-04-25 | 2006-01-25 | Chiron Corporation | Novel ketolide derivatives |
| US7332476B2 (en) * | 2003-04-25 | 2008-02-19 | Novartis Ag | Pyridyl substituted ketolide antibiotics |
| AU2008316830B2 (en) | 2007-10-25 | 2016-03-17 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| CN107854477A (zh) | 2008-10-24 | 2018-03-30 | 森普拉制药公司 | 使用含三唑的大环内酯治疗抗性疾病的方法 |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| US9480679B2 (en) | 2009-09-10 | 2016-11-01 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and MAC diseases |
| HRP20160168T1 (hr) | 2010-03-22 | 2016-03-25 | Cempra Pharmaceuticals Inc | Kristalne forme makrolida i njihova uporaba |
| BR112012029586A2 (pt) | 2010-05-20 | 2016-08-02 | Cempra Pharmaceuticals Inc | processos para preparar macrolídeos e cetolídeos e intermediários dos mesmos |
| KR20130120458A (ko) | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| WO2013148891A1 (en) | 2012-03-27 | 2013-10-03 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| WO2014152326A1 (en) | 2013-03-14 | 2014-09-25 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| AU2014233240B2 (en) | 2013-03-15 | 2018-08-09 | Cempra Pharmaceuticals, Inc. | Convergent processes for preparing macrolide antibacterial agents |
| EP4095146A1 (en) | 2013-04-04 | 2022-11-30 | President And Fellows Of Harvard College | Macrolides and methods of their preparation and use |
| JP2017531663A (ja) | 2014-10-08 | 2017-10-26 | プレジデント アンド フェローズ オブ ハーバード カレッジ | １４員ケトライドならびにそれらの調製および使用の方法 |
| WO2016154591A1 (en) | 2015-03-25 | 2016-09-29 | President And Fellows Of Harvard College | Macrolides with modified desosamine sugars and uses thereof |
| MD1222Z (ro) * | 2017-05-31 | 2018-08-31 | ИНСТИТУТ ЭЛЕКТРОННОЙ ИНЖЕНЕРИИ И НАНОТЕХНОЛОГИЙ "D. Ghitu" АНМ | Procedeu de tratare a materialului săditor al florilor înainte de plantare |
| JP7199722B2 (ja) | 2019-12-25 | 2023-01-06 | 旭精工株式会社 | 硬貨搬送振分機構及びそれを備えた硬貨識別搬送装置 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3868414A (en) * | 1973-01-22 | 1975-02-25 | Merck & Co Inc | Tetrahydrofluorene carboxylic acids and related compounds |
| AT342770B (de) * | 1975-04-07 | 1978-04-25 | Thomae Gmbh Dr K | Verfahren zur herstellung neuer erythromycinderivate |
| DE2842759A1 (de) * | 1978-09-30 | 1980-04-10 | Merck Patent Gmbh | Basische aether, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| IL99995A (en) * | 1990-11-21 | 1997-11-20 | Roussel Uclaf | Erythromycin derivatives, their preparation and pharmaceutical compositions containing them |
| FR2692579B1 (fr) * | 1992-06-19 | 1995-06-02 | Roussel Uclaf | Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2697524B1 (fr) * | 1992-11-05 | 1994-12-23 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| HRP930014A2 (en) * | 1993-01-08 | 1994-08-31 | Pliva Pharm & Chem Works | 9-deoxo-9a-aza-11-deoxy-9a-homoeritromycin a 9a, 11-cyclic carbamates |
| FR2702480B1 (fr) * | 1993-03-09 | 1995-04-28 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
-
1994
- 1994-04-08 FR FR9404154A patent/FR2718450B1/fr not_active Expired - Fee Related
-
1995
- 1995-01-05 LV LVP-95-363A patent/LV11182B/lv unknown
- 1995-03-10 IL IL11295495A patent/IL112954A/xx not_active IP Right Cessation
- 1995-03-13 ZA ZA952059A patent/ZA952059B/xx unknown
- 1995-03-17 AP APAP/P/1995/000743A patent/AP587A/en active
- 1995-03-19 JO JO19951850A patent/JO1850B1/en active
- 1995-03-31 US US08/414,503 patent/US5656607A/en not_active Expired - Lifetime
- 1995-04-02 DZ DZ950037A patent/DZ1869A1/fr active
- 1995-04-03 GB GB9506856A patent/GB2288174A/en not_active Withdrawn
- 1995-04-03 PE PE1995265509A patent/PE2896A1/es not_active IP Right Cessation
- 1995-04-05 YU YU21695A patent/YU49221B/sh unknown
- 1995-04-05 JP JP7103170A patent/JP3000023B2/ja not_active Expired - Lifetime
- 1995-04-05 CO CO95013829A patent/CO4370097A1/es unknown
- 1995-04-05 MA MA23828A patent/MA23501A1/fr unknown
- 1995-04-06 NZ NZ284498A patent/NZ284498A/en not_active IP Right Cessation
- 1995-04-06 UA UA95125173A patent/UA44705C2/uk unknown
- 1995-04-06 WO PCT/FR1995/000441 patent/WO1995027720A1/fr not_active Ceased
- 1995-04-06 EE EE9500080A patent/EE04498B1/xx unknown
- 1995-04-06 SK SK1546-95A patent/SK284079B6/sk not_active IP Right Cessation
- 1995-04-06 MD MD95-0431A patent/MD663G2/ro not_active IP Right Cessation
- 1995-04-06 KR KR1019950705537A patent/KR100317148B1/ko not_active Expired - Lifetime
- 1995-04-06 HU HU9503505A patent/HU215396B/hu unknown
- 1995-04-06 RO RO95-02126A patent/RO115634B1/ro unknown
- 1995-04-06 AU AU23107/95A patent/AU684939B2/en not_active Expired
- 1995-04-06 RU RU96101139A patent/RU2141965C1/ru active
- 1995-04-06 CA CA002164638A patent/CA2164638C/fr not_active Expired - Lifetime
- 1995-04-06 ES ES95400763T patent/ES2189820T3/es not_active Expired - Lifetime
- 1995-04-06 SI SI9530633T patent/SI0676409T1/xx unknown
- 1995-04-06 AT AT95400763T patent/ATE234853T1/de active
- 1995-04-06 EP EP95400763A patent/EP0676409B1/fr not_active Expired - Lifetime
- 1995-04-06 BR BR9506147A patent/BR9506147A/pt not_active IP Right Cessation
- 1995-04-06 PL PL95311871A patent/PL180837B1/pl unknown
- 1995-04-06 DE DE69529934T patent/DE69529934T2/de not_active Expired - Lifetime
- 1995-04-06 DK DK95400763T patent/DK0676409T3/da active
- 1995-04-06 CN CN95190283A patent/CN1059445C/zh not_active Expired - Lifetime
- 1995-04-06 PT PT95400763T patent/PT676409E/pt unknown
- 1995-04-06 TN TNTNSN95026A patent/TNSN95026A1/fr unknown
- 1995-04-06 CZ CZ19953223A patent/CZ296005B6/cs not_active IP Right Cessation
- 1995-04-07 HR HR950217A patent/HRP950217B1/xx not_active IP Right Cessation
- 1995-04-07 MY MYPI95000907A patent/MY114672A/en unknown
- 1995-04-07 SV SV1995000018A patent/SV1995000018A/es not_active Application Discontinuation
- 1995-04-08 GE GEAP19952968A patent/GEP19991836B/en unknown
- 1995-06-05 TW TW084105604A patent/TW316908B/zh not_active IP Right Cessation
- 1995-11-17 IS IS4309A patent/IS1865B/is unknown
- 1995-11-20 BG BG100150A patent/BG61916B1/bg unknown
- 1995-12-06 NO NO954942A patent/NO308361B1/no not_active IP Right Cessation
- 1995-12-08 FI FI955913A patent/FI111264B/fi not_active IP Right Cessation
- 1995-12-08 OA OA60752A patent/OA10200A/fr unknown
-
1997
- 1997-02-25 US US08/805,439 patent/US5760233A/en not_active Expired - Lifetime
- 1997-03-29 SA SA97170757A patent/SA97170757A/ar unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5747467A (en) * | 1995-12-22 | 1998-05-05 | Roussel Uclaf | Erythromycins |
| WO1998056800A1 (en) * | 1997-06-11 | 1998-12-17 | Pfizer Products Inc. | 9-oxime erythromycin derivatives |
| WO2000017218A1 (en) * | 1998-09-22 | 2000-03-30 | Pfizer Products Inc. | Carbamate and carbazate ketolide antibiotics |
| US6420343B1 (en) | 1998-09-22 | 2002-07-16 | Pfizer Inc | Carbamate and carbazate ketolide antibiotics |
| FR2786188A1 (fr) * | 1998-11-24 | 2000-05-26 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
| EP1004592A1 (fr) * | 1998-11-24 | 2000-05-31 | Hoechst Marion Roussel | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments |
| RU2237672C2 (ru) * | 1998-11-24 | 2004-10-10 | Хехст Марион Руссель | Новые производные эритромицина, способ их получения и применение в качестве медикаментов |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AP587A (en) | New erythromycin derivatives, their preparation process and their use as medicaments. | |
| US6147197A (en) | 6-O-substituted erythromycin ketolides having antibacterial activity | |
| US5635485A (en) | Erythromycin compounds | |
| US6096714A (en) | Erythromycin derivatives, method for preparing same, and use thereof as drugs | |
| US5866549A (en) | 6-O-substituted ketolides having antibacterial activity | |
| US5786339A (en) | Erythromycins | |
| AU766138B2 (en) | Novel erythromycin derivatives, preparation method and use as medicines | |
| US6313101B1 (en) | Derivatives of erythromycin, their preparation process and their use as medicaments | |
| US5750510A (en) | 3-descladinose-2,3-anhydroerythromycin derivatives | |
| AU5952299A (en) | New derivatives of erythromycin, their preparation process and their use as medicaments | |
| US6433151B1 (en) | Erythromycin derivatives, a process for their preparation and their use as medicaments | |
| FR2732023A1 (fr) | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments | |
| AP1078A (en) | Novel erythromycin derivatives, method for preparing same and use thereof as drugs. | |
| AU721732B2 (en) | New derivatives of erythromycin, their preparation process and their use as medicaments | |
| IL108622A (en) | 9-(1-substituted piperdine-3-yloxime) derivatives of 3-De(2,6-dideoxy-3-C-methyl-3-O-methyl-alpha-L-ribohexopyranosyl)oxy-6-O-methyl-3-oxo erythromycin their preparation process and their use as medicaments | |
| US5780604A (en) | 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides | |
| KR20000062286A (ko) | 신규한 에리트로마이신 유도체, 제조 방법 및 의약품으로서 용도 | |
| AU761551B2 (en) | Novel 6-deoxy erythromycin derivatives, method for preparing same and use as medicines | |
| USRE38520E1 (en) | Erythromycin derivatives, method for preparing same, and use thereof as drugs | |
| MXPA00002977A (en) | Cyclic phosphites and phosphates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| WAP | Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1) |