RU2126416C1 - Производные эритромицина, фармацевтическая композиция на их основе, способ их получения и промежуточные соединения - Google Patents
Производные эритромицина, фармацевтическая композиция на их основе, способ их получения и промежуточные соединения Download PDFInfo
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- RU2126416C1 RU2126416C1 RU93050129A RU93050129A RU2126416C1 RU 2126416 C1 RU2126416 C1 RU 2126416C1 RU 93050129 A RU93050129 A RU 93050129A RU 93050129 A RU93050129 A RU 93050129A RU 2126416 C1 RU2126416 C1 RU 2126416C1
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- methyl
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- dideoxy
- compounds
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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 abstract description 111
- 238000000034 method Methods 0.000 title claims description 10
- 239000000543 intermediate Substances 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 26
- 150000001875 compounds Chemical class 0.000 claims abstract description 79
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 239000002253 acid Substances 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 7
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 7
- 150000002148 esters Chemical class 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 150000001408 amides Chemical class 0.000 claims abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 2
- -1 5-membered heterocyclic aryl radical Chemical class 0.000 claims description 97
- 229960003276 erythromycin Drugs 0.000 claims description 58
- 150000003254 radicals Chemical class 0.000 claims description 19
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- XSAIZKZMMQOHRS-UHFFFAOYSA-N 4-thiophen-2-ylbutan-1-amine Chemical compound NCCCCC1=CC=CS1 XSAIZKZMMQOHRS-UHFFFAOYSA-N 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 4
- UOESEGCPAGEDML-UHFFFAOYSA-N 4-(2,4-dimethylphenyl)butan-1-amine Chemical compound CC1=CC=C(CCCCN)C(C)=C1 UOESEGCPAGEDML-UHFFFAOYSA-N 0.000 claims description 3
- MACWKONDJFBMEY-UHFFFAOYSA-N 4-(2-methoxyphenyl)butan-1-amine Chemical compound COC1=CC=CC=C1CCCCN MACWKONDJFBMEY-UHFFFAOYSA-N 0.000 claims description 3
- QFTRAKDGILOCCY-UHFFFAOYSA-N 4-(4-methylphenyl)butan-1-amine Chemical compound CC1=CC=C(CCCCN)C=C1 QFTRAKDGILOCCY-UHFFFAOYSA-N 0.000 claims description 3
- 230000003213 activating effect Effects 0.000 claims description 3
- PDVFSPNIEOYOQL-UHFFFAOYSA-N (4-methylphenyl)sulfonyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OS(=O)(=O)C1=CC=C(C)C=C1 PDVFSPNIEOYOQL-UHFFFAOYSA-N 0.000 claims description 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 2
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 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 claims description 2
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-Me3C6H3 Natural products CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 150000007513 acids Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 229910052717 sulfur Inorganic materials 0.000 abstract description 3
- 241000295644 Staphylococcaceae Species 0.000 abstract description 2
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 abstract 1
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 abstract 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 230000000845 anti-microbial effect Effects 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000000047 product Substances 0.000 description 77
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 52
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000377 silicon dioxide Substances 0.000 description 10
- 239000002585 base Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 239000013543 active substance Substances 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 5
- 239000002244 precipitate Substances 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910021529 ammonia Inorganic materials 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 239000007903 gelatin capsule Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 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 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229920000881 Modified starch Polymers 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-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
- 238000013019 agitation Methods 0.000 description 3
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- 238000005119 centrifugation Methods 0.000 description 3
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- 229940079593 drug Drugs 0.000 description 3
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- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 229960001375 lactose Drugs 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 3
- 235000019799 monosodium phosphate Nutrition 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- CBHCOZDTWGFWOY-UHFFFAOYSA-N 1-(4-phenylphenyl)butan-2-amine Chemical compound C1=CC(CC(N)CC)=CC=C1C1=CC=CC=C1 CBHCOZDTWGFWOY-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
- ISDBWOPVZKNQDW-UHFFFAOYSA-N 4-phenylbenzaldehyde Chemical compound C1=CC(C=O)=CC=C1C1=CC=CC=C1 ISDBWOPVZKNQDW-UHFFFAOYSA-N 0.000 description 2
- 229930024421 Adenine Natural products 0.000 description 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 description 2
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- 206010041925 Staphylococcal infections Diseases 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
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- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
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- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
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- 125000001841 imino group Chemical group [H]N=* 0.000 description 2
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
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- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- BKORROKTUCTEOK-UHFFFAOYSA-N 2-(3-bromopropyl)isoindole-1,3-dione;triphenylphosphanium;bromide Chemical compound [Br-].C1=CC=C2C(=O)N(CCCBr)C(=O)C2=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 BKORROKTUCTEOK-UHFFFAOYSA-N 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
- NFNBPCGRNXYGDI-UHFFFAOYSA-N 2-[4-(6-aminopurin-9-yl)but-3-enyl]isoindole-1,3-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1CCC=CN1C(N=CN=C2N)=C2N=C1 NFNBPCGRNXYGDI-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000004975 3-butenyl group Chemical group C(CC=C)* 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
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Images
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
- 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)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (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 |
|---|---|
| RU93050129A RU93050129A (ru) | 1996-12-27 |
| RU2126416C1 true RU2126416C1 (ru) | 1999-02-20 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU93050129A RU2126416C1 (ru) | 1992-11-05 | 1993-11-04 | Производные эритромицина, фармацевтическая композиция на их основе, способ их получения и промежуточные соединения |
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 |
| 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 |
| TR199901127T2 (xx) * | 1996-09-04 | 1999-07-21 | Abbott Laboratories | Antibakteriyel etkili 6-O-ikameli ketolitler. |
| 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 |
| EA199901016A1 (ru) * | 1997-06-11 | 2000-06-26 | Пфайзер Продактс Инк. | 9-оксим-производные эритромицина |
| 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 |
| WO1999021870A1 (en) * | 1997-10-29 | 1999-05-06 | 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 |
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| 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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- 1993-11-02 MA MA23324A patent/MA23018A1/fr unknown
- 1993-11-04 DE DE69301897T patent/DE69301897T2/de not_active Expired - Lifetime
- 1993-11-04 RU RU93050129A patent/RU2126416C1/ru active
- 1993-11-04 JP JP5297603A patent/JP3000022B2/ja not_active Expired - Lifetime
- 1993-11-04 EP EP93402704A patent/EP0596802B1/fr not_active Expired - Lifetime
- 1993-11-04 AT AT93402704T patent/ATE135706T1/de active
- 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 DK DK93402704.6T patent/DK0596802T3/da active
- 1993-11-05 AU AU50477/93A patent/AU670329B2/en not_active Expired
- 1993-11-05 KR KR1019930023371A patent/KR100317149B1/ko not_active Expired - Lifetime
- 1993-11-05 HU HU0200629D patent/HU222113B1/hu active IP Right Grant
- 1993-11-05 HU HU0003975A patent/HU221978B1/hu active IP Right Grant
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Also Published As
| Publication number | Publication date |
|---|---|
| CN1040876C (zh) | 1998-11-25 |
| DE69301897D1 (de) | 1996-04-25 |
| ATE135706T1 (de) | 1996-04-15 |
| HU222113B1 (hu) | 2003-04-28 |
| KR940011474A (ko) | 1994-06-21 |
| BR9304481A (pt) | 1994-06-21 |
| US5614614A (en) | 1997-03-25 |
| CA2102457C (fr) | 2002-01-22 |
| DE69301897T2 (de) | 1996-11-07 |
| GR3019385T3 (en) | 1996-06-30 |
| JPH06220082A (ja) | 1994-08-09 |
| MA23018A1 (fr) | 1994-07-01 |
| HUT66446A (en) | 1994-11-28 |
| JPH11180994A (ja) | 1999-07-06 |
| HU220048B (hu) | 2001-10-28 |
| CA2102457A1 (fr) | 1994-05-06 |
| ES2085130T3 (es) | 1996-05-16 |
| HU0003975D0 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2000-12-28 |
| AU5047793A (en) | 1994-05-19 |
| CN1090581A (zh) | 1994-08-10 |
| JP3000022B2 (ja) | 2000-01-17 |
| EP0596802A1 (fr) | 1994-05-11 |
| KR100317149B1 (ko) | 2002-06-20 |
| EP0596802B1 (fr) | 1996-03-20 |
| HU221978B1 (hu) | 2003-03-28 |
| AU670329B2 (en) | 1996-07-11 |
| DK0596802T3 (da) | 1996-06-03 |
| US5527780A (en) | 1996-06-18 |
| JP3151188B2 (ja) | 2001-04-03 |
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