CA2102457C - Derives de l'erythromycine, leur procede de preparation, leur application comme medicaments - Google Patents
Derives de l'erythromycine, leur procede de preparation, leur application comme medicaments Download PDFInfo
- Publication number
- CA2102457C CA2102457C CA002102457A CA2102457A CA2102457C CA 2102457 C CA2102457 C CA 2102457C CA 002102457 A CA002102457 A CA 002102457A CA 2102457 A CA2102457 A CA 2102457A CA 2102457 C CA2102457 C CA 2102457C
- Authority
- CA
- Canada
- Prior art keywords
- aryl
- radical
- alkyl
- substituted
- radicals
- 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.)
- Expired - Lifetime
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- 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 62
- 238000002360 preparation method Methods 0.000 title claims description 28
- 239000003814 drug Substances 0.000 title claims description 14
- 238000000034 method Methods 0.000 title claims description 8
- -1 carbocyclic aryl radical Chemical class 0.000 claims abstract description 137
- 150000001875 compounds Chemical class 0.000 claims abstract description 94
- 150000003254 radicals Chemical group 0.000 claims abstract description 79
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 239000002253 acid Substances 0.000 claims abstract description 17
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 47
- 229960003276 erythromycin Drugs 0.000 claims description 32
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000000623 heterocyclic group Chemical group 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 14
- 125000004122 cyclic group Chemical group 0.000 claims description 13
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 10
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 150000007513 acids Chemical class 0.000 claims description 8
- 229940079593 drug Drugs 0.000 claims description 8
- 238000007363 ring formation reaction Methods 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 claims description 4
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 230000003213 activating effect Effects 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 235000010290 biphenyl Nutrition 0.000 claims description 3
- 239000004305 biphenyl Substances 0.000 claims description 3
- 210000000988 bone and bone Anatomy 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims 17
- 150000005840 aryl radicals Chemical class 0.000 claims 12
- 125000004429 atom Chemical group 0.000 claims 10
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 101100293593 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nar-1 gene Proteins 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000000047 product Substances 0.000 description 83
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 34
- DZCOSWPAQGXWKC-TZIZHKBZSA-N (3r,4s,5s,6r,7r,9r,11r,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3-(hydroxymethyl)-5,7,9,11,13-pentamethyl-oxacyclotetradecane Chemical compound O([C@@H]1[C@@H](CO)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 DZCOSWPAQGXWKC-TZIZHKBZSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 15
- 239000012141 concentrate Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 241000194017 Streptococcus Species 0.000 description 12
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- 235000019359 magnesium stearate Nutrition 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- 239000000454 talc Substances 0.000 description 6
- 229910052623 talc Inorganic materials 0.000 description 6
- XSAIZKZMMQOHRS-UHFFFAOYSA-N 4-thiophen-2-ylbutan-1-amine Chemical compound NCCCCC1=CC=CS1 XSAIZKZMMQOHRS-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 235000012222 talc Nutrition 0.000 description 5
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000191940 Staphylococcus Species 0.000 description 4
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VJMAITQRABEEKP-UHFFFAOYSA-N [6-(phenylmethoxymethyl)-1,4-dioxan-2-yl]methyl acetate Chemical compound O1C(COC(=O)C)COCC1COCC1=CC=CC=C1 VJMAITQRABEEKP-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 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
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 2
- UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 2
- VUGWBHVXXNGKGR-UHFFFAOYSA-N 4-(2-phenylimidazol-1-yl)butan-1-amine Chemical compound NCCCCN1C=CN=C1C1=CC=CC=C1 VUGWBHVXXNGKGR-UHFFFAOYSA-N 0.000 description 2
- DEFPUGDPVDPBIJ-UHFFFAOYSA-N 4-(4-phenylphenyl)butan-1-amine Chemical compound C1=CC(CCCCN)=CC=C1C1=CC=CC=C1 DEFPUGDPVDPBIJ-UHFFFAOYSA-N 0.000 description 2
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- 206010002383 Angina Pectoris Diseases 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 125000000848 adenin-9-yl group Chemical group [H]N([H])C1=C2N=C([H])N(*)C2=NC([H])=N1 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 244000052616 bacterial pathogen Species 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229940047650 haemophilus influenzae Drugs 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
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- 239000007788 liquid Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000004452 microanalysis Methods 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- PPKPKFIWDXDAGC-IHWYPQMZSA-N (z)-1,2-dichloroprop-1-ene Chemical compound C\C(Cl)=C\Cl PPKPKFIWDXDAGC-IHWYPQMZSA-N 0.000 description 1
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-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
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 1
- VDJDPVZOKKZAAH-UHFFFAOYSA-N 2-[4-(2-phenylimidazol-1-yl)butyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCCCN1C=CN=C1C1=CC=CC=C1 VDJDPVZOKKZAAH-UHFFFAOYSA-N 0.000 description 1
- OLHHSTALORFUQH-UHFFFAOYSA-N 2-[4-(4-phenylphenyl)but-3-enyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC=CC(C=C1)=CC=C1C1=CC=CC=C1 OLHHSTALORFUQH-UHFFFAOYSA-N 0.000 description 1
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- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-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
- QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 1
- WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 1
- OJFHQGJQVODWBX-UHFFFAOYSA-N 4-(2,4,6-trimethylphenyl)butan-1-amine Chemical compound CC1=CC(C)=C(CCCCN)C(C)=C1 OJFHQGJQVODWBX-UHFFFAOYSA-N 0.000 description 1
- UOESEGCPAGEDML-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)butan-1-amine Chemical compound CC1=CC=C(CCCCN)C(C)=C1 UOESEGCPAGEDML-UHFFFAOYSA-N 0.000 description 1
- MACWKONDJFBMEY-UHFFFAOYSA-N 4-(2-methoxyphenyl)butan-1-amine Chemical compound COC1=CC=CC=C1CCCCN MACWKONDJFBMEY-UHFFFAOYSA-N 0.000 description 1
- NBEFNEOOMNRCEP-UHFFFAOYSA-N 4-(2-phenyl-1,3-thiazol-5-yl)butan-1-amine Chemical compound S1C(CCCCN)=CN=C1C1=CC=CC=C1 NBEFNEOOMNRCEP-UHFFFAOYSA-N 0.000 description 1
- RPPYVBBEEXAIPM-UHFFFAOYSA-N 4-(2-phenylphenyl)butan-1-amine Chemical compound NCCCCC1=CC=CC=C1C1=CC=CC=C1 RPPYVBBEEXAIPM-UHFFFAOYSA-N 0.000 description 1
- VYTXLSQVYGNWLV-UHFFFAOYSA-N 4-(2-thienyl)butyric acid Chemical compound OC(=O)CCCC1=CC=CS1 VYTXLSQVYGNWLV-UHFFFAOYSA-N 0.000 description 1
- DBRKOJIBBAJAII-UHFFFAOYSA-N 4-(4-chlorophenyl)butan-1-amine Chemical compound NCCCCC1=CC=C(Cl)C=C1 DBRKOJIBBAJAII-UHFFFAOYSA-N 0.000 description 1
- USDPTYHOEKPQAN-UHFFFAOYSA-N 4-(4-methoxyphenyl)butan-1-amine Chemical compound COC1=CC=C(CCCCN)C=C1 USDPTYHOEKPQAN-UHFFFAOYSA-N 0.000 description 1
- QFTRAKDGILOCCY-UHFFFAOYSA-N 4-(4-methylphenyl)butan-1-amine Chemical compound CC1=CC=C(CCCCN)C=C1 QFTRAKDGILOCCY-UHFFFAOYSA-N 0.000 description 1
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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
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9213320A FR2697523B1 (fr) | 1992-11-05 | 1992-11-05 | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR9213320 | 1992-11-05 | ||
| FR9308109 | 1993-07-02 | ||
| FR9308109A FR2707088B1 (fr) | 1993-07-02 | 1993-07-02 | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2102457A1 CA2102457A1 (fr) | 1994-05-06 |
| CA2102457C true CA2102457C (fr) | 2002-01-22 |
Family
ID=26229842
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002102457A Expired - Lifetime CA2102457C (fr) | 1992-11-05 | 1993-11-04 | Derives de l'erythromycine, leur procede de preparation, leur application comme medicaments |
Country Status (16)
Families Citing this family (86)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2718450B1 (fr) * | 1994-04-08 | 1997-01-10 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2719587B1 (fr) * | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2727969B1 (fr) * | 1994-12-09 | 1997-01-17 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2732023B1 (fr) * | 1995-03-22 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2732684B1 (fr) * | 1995-04-06 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US5747466A (en) * | 1995-11-08 | 1998-05-05 | Abbott Laboratories | 3-deoxy-3-descladinose derivatives of erythromycins A and B |
| FR2742757B1 (fr) | 1995-12-22 | 1998-01-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| 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 |
| SK285536B6 (sk) * | 1996-09-04 | 2007-03-01 | Abbott Laboratories | 6-O-substituované ketolidy s antibakteriálnou aktivitou, farmaceutická kompozícia s ich obsahom, ich použitie a spôsob ich prípravy |
| 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 |
| 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 |
| US5922683A (en) * | 1997-05-29 | 1999-07-13 | Abbott Laboratories | Multicyclic erythromycin derivatives |
| WO1998056800A1 (en) * | 1997-06-11 | 1998-12-17 | Pfizer Products Inc. | 9-oxime erythromycin derivatives |
| US5780604A (en) * | 1997-09-26 | 1998-07-14 | Abbott Laboratories | 11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides |
| US6034069A (en) * | 1997-09-30 | 2000-03-07 | Abbott Laboratories | 3-'N-modified 6-O-substituted erythromycin ketolide derivatives having antibacterial activity |
| US6124269A (en) * | 1997-10-29 | 2000-09-26 | Abbott Laboratories | 2-Halo-6-O-substituted ketolide derivatives |
| AU9649698A (en) * | 1997-10-29 | 1999-05-17 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a 11, 12-carbamate derivatives |
| US6046171A (en) * | 1997-10-29 | 2000-04-04 | Abbott Laboratories | 6,11-bridged erythromycin derivatives |
| JP2003527301A (ja) * | 1997-10-29 | 2003-09-16 | 大正製薬株式会社 | エリスロマイシンａ誘導体 |
| HRP980189B1 (en) * | 1998-04-06 | 2004-04-30 | Pliva Pharm & Chem Works | Novel 15-membered lactams ketolides |
| FR2777282B1 (fr) * | 1998-04-08 | 2001-04-20 | Hoechst Marion Roussel Inc | Nouveaux derives de la 2-fluoro 3-de((2,6-dideoxy 3-c-methyl 3-0-methyl-alpha-l-ribohexopyranosyl) oxyl) 6-o-methyl 3-oxo erythromycine, leur procede de preparation et leur application a la synthese de principes actifs de medicaments |
| JP4573925B2 (ja) * | 1998-07-09 | 2010-11-04 | アベンティス・ファーマ・ソシエテ・アノニム | 新規のエリスロマイシン誘導体、その製造方法及びその薬剤としての使用 |
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| AT342770B (de) * | 1975-04-07 | 1978-04-25 | Thomae Gmbh Dr K | Verfahren zur herstellung neuer erythromycinderivate |
| DE2936865A1 (de) * | 1979-09-12 | 1981-04-02 | Bayer Ag, 5090 Leverkusen | Verwendung von pikromycin-derivaten als nutritiva |
| GR77556B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1982-11-15 | 1984-09-24 | Pfizer | |
| JPS6229595A (ja) * | 1985-07-31 | 1987-02-07 | Toyo Jozo Co Ltd | ５−ｏ−マイカミノシル−ナルボノライド誘導体およびその製法 |
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| CA2096969C (en) * | 1990-11-28 | 2000-11-21 | Masato Kashimura | 6-0-methylerythromycin a derivatives |
| FR2692579B1 (fr) * | 1992-06-19 | 1995-06-02 | Roussel Uclaf | Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments. |
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| FR2702480B1 (fr) * | 1993-03-09 | 1995-04-28 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
-
1993
- 1993-11-01 US US08/146,697 patent/US5527780A/en not_active Expired - Lifetime
- 1993-11-02 MA MA23324A patent/MA23018A1/fr unknown
- 1993-11-04 BR BR9304481A patent/BR9304481A/pt not_active Application Discontinuation
- 1993-11-04 ES ES93402704T patent/ES2085130T3/es not_active Expired - Lifetime
- 1993-11-04 CA CA002102457A patent/CA2102457C/fr not_active Expired - Lifetime
- 1993-11-04 DE DE69301897T patent/DE69301897T2/de not_active Expired - Lifetime
- 1993-11-04 DK DK93402704.6T patent/DK0596802T3/da active
- 1993-11-04 AT AT93402704T patent/ATE135706T1/de active
- 1993-11-04 RU RU93050129A patent/RU2126416C1/ru active
- 1993-11-04 EP EP93402704A patent/EP0596802B1/fr not_active Expired - Lifetime
- 1993-11-04 JP JP5297603A patent/JP3000022B2/ja not_active Expired - Lifetime
- 1993-11-05 CN CN93114229A patent/CN1040876C/zh not_active Expired - Lifetime
- 1993-11-05 AU AU50477/93A patent/AU670329B2/en not_active Expired
- 1993-11-05 HU HU0200629D patent/HU222113B1/hu active IP Right Grant
- 1993-11-05 HU HU9303148A patent/HU220048B/hu unknown
- 1993-11-05 HU HU0003975A patent/HU221978B1/hu active IP Right Grant
- 1993-11-05 KR KR1019930023371A patent/KR100317149B1/ko not_active Expired - Lifetime
-
1995
- 1995-02-21 US US08/391,959 patent/US5614614A/en not_active Expired - Lifetime
-
1996
- 1996-03-21 GR GR950403179T patent/GR3019385T3/el unknown
-
1998
- 1998-09-03 JP JP26389698A patent/JP3151188B2/ja not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11180994A (ja) | 1999-07-06 |
| US5527780A (en) | 1996-06-18 |
| GR3019385T3 (en) | 1996-06-30 |
| JP3000022B2 (ja) | 2000-01-17 |
| EP0596802B1 (fr) | 1996-03-20 |
| RU2126416C1 (ru) | 1999-02-20 |
| CN1040876C (zh) | 1998-11-25 |
| HU220048B (hu) | 2001-10-28 |
| DK0596802T3 (da) | 1996-06-03 |
| KR100317149B1 (ko) | 2002-06-20 |
| KR940011474A (ko) | 1994-06-21 |
| JP3151188B2 (ja) | 2001-04-03 |
| HU222113B1 (hu) | 2003-04-28 |
| BR9304481A (pt) | 1994-06-21 |
| US5614614A (en) | 1997-03-25 |
| MA23018A1 (fr) | 1994-07-01 |
| DE69301897D1 (de) | 1996-04-25 |
| HU221978B1 (hu) | 2003-03-28 |
| DE69301897T2 (de) | 1996-11-07 |
| CN1090581A (zh) | 1994-08-10 |
| ATE135706T1 (de) | 1996-04-15 |
| EP0596802A1 (fr) | 1994-05-11 |
| AU5047793A (en) | 1994-05-19 |
| AU670329B2 (en) | 1996-07-11 |
| ES2085130T3 (es) | 1996-05-16 |
| HU0003975D0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2000-12-28 |
| CA2102457A1 (fr) | 1994-05-06 |
| JPH06220082A (ja) | 1994-08-09 |
| HUT66446A (en) | 1994-11-28 |
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