BG61369B2 - Нови оксими производни на еритромицин а, получаването им,приложението им като лекарствени средства и съдържащите ги фармацевтични състави - Google Patents
Нови оксими производни на еритромицин а, получаването им,приложението им като лекарствени средства и съдържащите ги фармацевтични състави Download PDFInfo
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- BG61369B2 BG61369B2 BG098506A BG9850694A BG61369B2 BG 61369 B2 BG61369 B2 BG 61369B2 BG 098506 A BG098506 A BG 098506A BG 9850694 A BG9850694 A BG 9850694A BG 61369 B2 BG61369 B2 BG 61369B2
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- Prior art keywords
- radical
- formula
- product
- products
- erythromycin
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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 217
- 150000002923 oximes Chemical class 0.000 title claims description 87
- 239000003814 drug Substances 0.000 title claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 229940079593 drug Drugs 0.000 title description 7
- -1 vinyloxy Chemical group 0.000 claims abstract description 142
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 28
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 21
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 17
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000005843 halogen group Chemical group 0.000 claims abstract description 15
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 14
- 150000007524 organic acids Chemical class 0.000 claims abstract description 14
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 13
- 239000011707 mineral Substances 0.000 claims abstract description 13
- 235000005985 organic acids Nutrition 0.000 claims abstract description 13
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 10
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 10
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract description 9
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims abstract description 9
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 8
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 8
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 6
- 125000005336 allyloxy group Chemical group 0.000 claims abstract description 5
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 5
- 239000012434 nucleophilic reagent Substances 0.000 claims abstract description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims abstract description 4
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000000177 propargylthio group Chemical group [H]C#CC([H])([H])S* 0.000 claims abstract description 3
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims abstract 2
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical group O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims abstract 2
- 229960003276 erythromycin Drugs 0.000 claims description 106
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 38
- 239000012312 sodium hydride Substances 0.000 claims description 38
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 38
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 37
- 150000003254 radicals Chemical group 0.000 claims description 35
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 23
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 14
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 12
- 230000002378 acidificating effect Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 7
- 125000005109 alkynylthio group Chemical group 0.000 claims description 6
- AYJRCSIUFZENHW-UHFFFAOYSA-L barium carbonate Chemical compound [Ba+2].[O-]C([O-])=O AYJRCSIUFZENHW-UHFFFAOYSA-L 0.000 claims description 6
- 125000004434 sulfur atom Chemical group 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 150000003457 sulfones Chemical class 0.000 claims description 2
- 150000003462 sulfoxides Chemical class 0.000 claims 2
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 1
- 241000405217 Viola <butterfly> Species 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 150000001243 acetic acids Chemical class 0.000 claims 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-O hydron;pyrimidine Chemical compound C1=CN=C[NH+]=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-O 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 4
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 abstract description 3
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 abstract description 2
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 2
- 125000001174 sulfone group Chemical group 0.000 abstract 2
- KKFDJZZADQONDE-UHFFFAOYSA-N (hydridonitrato)hydroxidocarbon(.) Chemical compound O[C]=N KKFDJZZADQONDE-UHFFFAOYSA-N 0.000 abstract 1
- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 abstract 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 abstract 1
- 239000000047 product Substances 0.000 description 178
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 141
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 90
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 78
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 72
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 60
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 56
- 239000000243 solution Substances 0.000 description 54
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 53
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 43
- 239000000377 silicon dioxide Substances 0.000 description 38
- 238000004458 analytical method Methods 0.000 description 36
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 26
- 239000011347 resin Substances 0.000 description 26
- 229920005989 resin Polymers 0.000 description 26
- 239000000706 filtrate Substances 0.000 description 24
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- 239000011780 sodium chloride Substances 0.000 description 22
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 21
- 229920006395 saturated elastomer Polymers 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- MMFVFNVXXDFELX-UHFFFAOYSA-N chloroform;n,n-diethylethanamine Chemical group ClC(Cl)Cl.CCN(CC)CC MMFVFNVXXDFELX-UHFFFAOYSA-N 0.000 description 16
- 239000002244 precipitate Substances 0.000 description 16
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 14
- 239000012043 crude product Substances 0.000 description 14
- 241000194017 Streptococcus Species 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 229940086542 triethylamine Drugs 0.000 description 12
- 239000012300 argon atmosphere Substances 0.000 description 11
- 239000013078 crystal Substances 0.000 description 11
- 239000003208 petroleum Substances 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 235000010755 mineral Nutrition 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 9
- 238000004090 dissolution Methods 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- 239000011734 sodium Substances 0.000 description 9
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229910002092 carbon dioxide Inorganic materials 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- NTEUNCALHORCCY-UHFFFAOYSA-N n,n-diethylethanamine;toluene Chemical compound CCN(CC)CC.CC1=CC=CC=C1 NTEUNCALHORCCY-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- CYLJJGWXJNNBDU-UHFFFAOYSA-N 2-[2,3-bis(2-aminoethyl)phenyl]ethanamine Chemical compound NCCC1=CC=CC(CCN)=C1CCN CYLJJGWXJNNBDU-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
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- 125000006012 2-chloroethoxy group Chemical group 0.000 description 5
- 241000699670 Mus sp. Species 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 238000013375 chromatographic separation Methods 0.000 description 5
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 241000194032 Enterococcus faecalis Species 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- 206010061218 Inflammation Diseases 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Chemical class 0.000 description 4
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- PMPYSSMGWFNAAQ-UHFFFAOYSA-N dichloromethane;n,n-diethylethanamine Chemical compound ClCCl.CCN(CC)CC PMPYSSMGWFNAAQ-UHFFFAOYSA-N 0.000 description 4
- 238000010932 ethanolysis reaction Methods 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- NTHKNMPHBNQTJM-UHFFFAOYSA-N 1-chloro-n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CC(Cl)N(C)C NTHKNMPHBNQTJM-UHFFFAOYSA-N 0.000 description 3
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- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
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- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\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 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 description 2
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
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- LQLJZSJKRYTKTP-UHFFFAOYSA-N 2-dimethylaminoethyl chloride hydrochloride Chemical compound Cl.CN(C)CCCl LQLJZSJKRYTKTP-UHFFFAOYSA-N 0.000 description 2
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- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8000566A FR2473525A1 (fr) | 1980-01-11 | 1980-01-11 | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG61369B2 true BG61369B2 (bg) | 1997-06-30 |
Family
ID=9237443
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG098506A BG61369B2 (bg) | 1980-01-11 | 1994-02-22 | Нови оксими производни на еритромицин а, получаването им,приложението им като лекарствени средства и съдържащите ги фармацевтични състави |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4349545A (es) |
| EP (1) | EP0033255B1 (es) |
| JP (1) | JPS56100799A (es) |
| KR (1) | KR850000964B1 (es) |
| AU (1) | AU537247B2 (es) |
| BG (1) | BG61369B2 (es) |
| CA (1) | CA1162535A (es) |
| CY (1) | CY1319A (es) |
| DE (1) | DE3165720D1 (es) |
| DK (1) | DK157878C (es) |
| ES (1) | ES8200702A1 (es) |
| FI (1) | FI69473C (es) |
| FR (1) | FR2473525A1 (es) |
| GR (1) | GR73103B (es) |
| GT (1) | GT198500080A (es) |
| HK (1) | HK586A (es) |
| HU (1) | HU187760B (es) |
| IE (1) | IE50680B1 (es) |
| IL (1) | IL61808A (es) |
| LU (1) | LU88283I2 (es) |
| MY (1) | MY8500984A (es) |
| NL (1) | NL930097I2 (es) |
| OA (1) | OA06719A (es) |
| PT (1) | PT72331B (es) |
| ZA (1) | ZA808108B (es) |
Families Citing this family (42)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2534588B2 (fr) * | 1982-10-15 | 1985-09-20 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US4526889A (en) * | 1982-11-15 | 1985-07-02 | Pfizer Inc. | Epimeric azahomoerythromycin A derivative, intermediates and method of use |
| DK149776C (da) * | 1984-01-06 | 1987-04-21 | Orion Yhtymae Oy | Antibiotisk virksom erytromycinforbindelse og praeparat indeholdende forbindelsen |
| JPS60214796A (ja) * | 1984-04-06 | 1985-10-28 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシン類の製法 |
| JPS61103890A (ja) * | 1984-10-26 | 1986-05-22 | Taisho Pharmaceut Co Ltd | ６−０−メチルエリスロマイシンａ誘導体 |
| DE3668894D1 (en) | 1985-03-12 | 1990-03-15 | Beecham Group Plc | Erythromycin-derivate. |
| JPS61229895A (ja) * | 1985-04-03 | 1986-10-14 | Nippon Zeon Co Ltd | 保護化デス−ｎ−メチルエリスロマイシン誘導体 |
| US4740502A (en) * | 1986-06-20 | 1988-04-26 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
| EP0260938B1 (en) | 1986-09-18 | 1992-12-09 | Taisho Pharmaceutical Co. Ltd | Erythromycin a derivatives and method for preparing the same |
| JP2751385B2 (ja) * | 1988-05-19 | 1998-05-18 | 大正製薬株式会社 | エリスロマイシンａオキシム及びその塩の製造方法 |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
| US5302705A (en) * | 1989-10-07 | 1994-04-12 | Taisho Pharmaceutical Co., Ltd. | 6-O-methylerythromycin a oxime derivatives |
| CA2062932A1 (en) | 1991-03-15 | 1992-09-16 | Robert R. Wilkening | 9-deoxo-9(z)-hydroxyiminoerythromycin a and o-derivatives thereof |
| US5912331A (en) * | 1991-03-15 | 1999-06-15 | Merck & Co., Inc. | Process for the preparation of 9-deoxo-9(Z)-hydroxyiminoerythromycin A |
| US5985844A (en) * | 1992-03-26 | 1999-11-16 | Merck & Co., Inc. | Homoerythromycin A derivatives modified at the 4"-and 8A-positions |
| US5189159A (en) * | 1992-04-02 | 1993-02-23 | Merck & Co., Inc. | 8a-AZA-8a-homoerythromycin cyclic iminoethers |
| ES2036472B1 (es) * | 1991-10-01 | 1994-03-01 | Prodesfarma Sa | Procedimiento de obtencion de eritromicina 9-(0-((2-metoxietoxi)metil)oxima) (roxitromicina). |
| US5210235A (en) * | 1992-08-26 | 1993-05-11 | Merck & Co., Inc. | Methods of elaborating erythromycin fragments into amine-containing fragments of azalide antibiotics |
| US5332807A (en) * | 1993-04-14 | 1994-07-26 | Merck & Co., Inc. | Process of producing 8A- and 9A-azalide antibiotics |
| US5795871A (en) * | 1994-04-26 | 1998-08-18 | Nobuhiro Narita | Pharmaceutical composition for treatment of non-small cell lung cancer |
| IT1276901B1 (it) * | 1994-12-13 | 1997-11-03 | Zambon Spa | Derivati dell'eritromicina a 9-0-ossina dotati di attivita' antibiotica |
| US5872229A (en) | 1995-11-21 | 1999-02-16 | Abbott Laboratories | Process for 6-O-alkylation of erythromycin derivatives |
| 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 |
| US5929219A (en) | 1997-09-10 | 1999-07-27 | Abbott Laboratories | 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same |
| PT102202B (pt) | 1998-09-10 | 2001-04-30 | Hovione Sociedade Quimica S A | Processo para a purificacao de roxitromicina |
| IN190782B (es) * | 1998-09-30 | 2003-08-23 | Max India Ltd | |
| EP1004591B1 (en) * | 1998-11-24 | 2003-04-09 | Max India Limited | Process for preparing roxithromycin and derivatives thereof |
| IL150227A0 (en) * | 1999-12-16 | 2002-12-01 | Teva Pharma | Processes for preparing clarithromycin polymorphs and novel polymorph iv |
| AU2261901A (en) * | 2000-01-11 | 2001-07-24 | Teva Pharma | Processes for preparing clarithromycin polymorphs |
| EP1313486A1 (en) | 2000-02-29 | 2003-05-28 | Teva Pharmaceutical Industries Ltd. | Processes for preparing clarithromycin and clarithromycin intermediate, essentially oxime-free clarithromycin, and pharmaceutical composition comprising the same |
| HRP20020885B1 (en) | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| HRP20020991A2 (en) | 2002-12-12 | 2005-02-28 | Pliva-Istra�iva�ki institut d.o.o. | N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de |
| AU2003271408B2 (en) * | 2002-12-31 | 2008-07-17 | Alembic Limited | A process for the purification of roxithromycin |
| EP2056844A4 (en) | 2006-08-24 | 2010-11-24 | Wockhardt Research Center | NEW MACROLIDS AND KETOLIDS WITH ANTIMICROBIAL EFFECT |
| US20090005326A1 (en) * | 2007-06-26 | 2009-01-01 | Idexx Laboratories, Inc. | Single dose roxithromycin |
| NZ623574A (en) | 2010-12-09 | 2015-07-31 | Wockhardt Ltd | Ketolide compounds |
| WO2012117357A2 (en) | 2011-03-01 | 2012-09-07 | Wockhardt Limited | Process for preparation of ketolide intermediates |
| US8993739B2 (en) | 2011-03-22 | 2015-03-31 | Wockhardt Ltd. | Process for preparation of ketolide compounds |
| CN102219816A (zh) * | 2011-05-12 | 2011-10-19 | 浙江国邦药业有限公司 | 一种罗红霉素的纯化方法 |
| PL222631B1 (pl) | 2012-11-14 | 2016-08-31 | Gdański Univ Medyczny | Kompozycja farmaceutyczna zawierająca roksytromycynę, sposób jej wytwarzania oraz zastosowanie medyczne tej kompozycji i produkt leczniczy zawierający kompozycję |
| CN104163840A (zh) * | 2013-08-30 | 2014-11-26 | 郑州后羿制药有限公司 | 一种罗红霉素的精制方法 |
| FR3049861A1 (fr) | 2016-04-07 | 2017-10-13 | Univ Claude Bernard Lyon | Nouvelles compositions antivirales pour le traitement de la grippe |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU31319B (en) * | 1967-08-03 | 1973-04-30 | Pliva Pharm & Chem Works | Postupak za dobijanje acil derivata eritromicin oksima |
| US3869444A (en) * | 1972-10-10 | 1975-03-04 | Abbott Lab | Esters of erythromycin oxime |
| ES434842A1 (es) * | 1975-02-19 | 1976-12-01 | Andreu Sa Dr | Procedimiento para la preparacion de esteres de la oxima deeritromicina. |
| DE2515076A1 (de) * | 1975-04-07 | 1976-10-28 | Thomae Gmbh Dr K | Neue erythromycinderivate, deren salze und verfahren zu ihrer herstellung |
| DE2515077A1 (de) * | 1975-04-07 | 1976-10-28 | Thomae Gmbh Dr K | Neue 9-alkylidenamino-erythromycine, ihre salze und verfahren zu ihrer herstellung |
| DK139522C (da) * | 1975-04-07 | 1979-08-20 | Thomae Gmbh Dr K | Analogifremgangsmaade til fremstilling af 9-iminoalkylamino-erythromyciner eller syreadditionssalte deraf |
| DE2750288A1 (de) * | 1977-11-10 | 1979-05-17 | Thomae Gmbh Dr K | Neue 9-(omega-heteroarylamino- alkylamino)-erythromycine, ihre salze, verfahren zu ihrer herstellung und diese enthaltende arzneimittel |
-
1980
- 1980-01-11 FR FR8000566A patent/FR2473525A1/fr active Granted
- 1980-12-26 IL IL61808A patent/IL61808A/xx not_active IP Right Cessation
- 1980-12-30 ZA ZA00808108A patent/ZA808108B/xx unknown
-
1981
- 1981-01-08 US US06/223,368 patent/US4349545A/en not_active Expired - Lifetime
- 1981-01-08 FI FI810042A patent/FI69473C/fi not_active IP Right Cessation
- 1981-01-09 EP EP81400026A patent/EP0033255B1/fr not_active Expired
- 1981-01-09 GR GR63831A patent/GR73103B/el unknown
- 1981-01-09 DE DE8181400026T patent/DE3165720D1/de not_active Expired
- 1981-01-09 AU AU66131/81A patent/AU537247B2/en not_active Expired
- 1981-01-09 JP JP126481A patent/JPS56100799A/ja active Granted
- 1981-01-09 OA OA57295A patent/OA06719A/xx unknown
- 1981-01-09 HU HU8155A patent/HU187760B/hu unknown
- 1981-01-09 ES ES498395A patent/ES8200702A1/es not_active Expired
- 1981-01-09 DK DK007881A patent/DK157878C/da active
- 1981-01-09 IE IE46/81A patent/IE50680B1/en not_active IP Right Cessation
- 1981-01-09 CA CA000368249A patent/CA1162535A/fr not_active Expired
- 1981-01-09 PT PT72331A patent/PT72331B/pt unknown
- 1981-01-09 CY CY1319A patent/CY1319A/xx unknown
- 1981-01-10 KR KR1019810000051A patent/KR850000964B1/ko active
-
1985
- 1985-09-12 GT GT198500080A patent/GT198500080A/es unknown
- 1985-12-30 MY MY984/85A patent/MY8500984A/xx unknown
-
1986
- 1986-01-02 HK HK5/86A patent/HK586A/xx not_active IP Right Cessation
-
1993
- 1993-06-03 LU LU88283C patent/LU88283I2/fr unknown
- 1993-06-25 NL NL930097C patent/NL930097I2/nl unknown
-
1994
- 1994-02-22 BG BG098506A patent/BG61369B2/bg unknown
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