AP888A - Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials. - Google Patents
Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials. Download PDFInfo
- Publication number
- AP888A AP888A APAP/P/1998/001216A AP9801216A AP888A AP 888 A AP888 A AP 888A AP 9801216 A AP9801216 A AP 9801216A AP 888 A AP888 A AP 888A
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- Prior art keywords
- formula
- compound
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- subjected
- compounds
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 9
- 239000011149 active material Substances 0.000 title 1
- 229930193775 erythronolide Natural products 0.000 title 1
- ZFBRGCCVTUPRFQ-UHFFFAOYSA-N erythronolide-B Natural products CCC1OC(=O)C(C)C(O)C(C)C(O)C(C)(O)CC(C)C(=O)C(C)C(O)C1C ZFBRGCCVTUPRFQ-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 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
- 230000003213 activating effect Effects 0.000 claims description 3
- 239000003638 chemical reducing agent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 229910017852 NH2NH2 Inorganic materials 0.000 claims description 2
- 125000000524 functional group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000007800 oxidant agent Substances 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000003115 biocidal effect Effects 0.000 abstract description 3
- 150000001732 carboxylic acid derivatives Chemical group 0.000 abstract description 3
- 239000000047 product Substances 0.000 description 37
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 238000013019 agitation Methods 0.000 description 15
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 9
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- -1 isobutyryl Chemical group 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- MWBJRTBANFUBOX-SQYJNGITSA-N (3r,4s,5s,6r,7r,9r,10e,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-12,13-dihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-7-methoxy-3,5,7,9,11,13-hexamethyl-oxacyclot 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 MWBJRTBANFUBOX-SQYJNGITSA-N 0.000 description 4
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 229960003276 erythromycin Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 238000003776 cleavage reaction Methods 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000005638 hydrazono group Chemical group 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 230000007017 scission Effects 0.000 description 2
- 239000012279 sodium borohydride Substances 0.000 description 2
- 229910000033 sodium borohydride Inorganic materials 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical compound CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-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
- SGUVLZREKBPKCE-UHFFFAOYSA-N 1,5-diazabicyclo[4.3.0]-non-5-ene Chemical compound C1CCN=C2CCCN21 SGUVLZREKBPKCE-UHFFFAOYSA-N 0.000 description 1
- XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 1
- OKJFQNPFBIKFPM-UHFFFAOYSA-N 2-quinolin-4-ylpropanal Chemical compound C1=CC=C2C(C(C=O)C)=CC=NC2=C1 OKJFQNPFBIKFPM-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005708 carbonyloxy group Chemical group [*:2]OC([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 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
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 235000015424 sodium Nutrition 0.000 description 1
- 235000019980 sodium acid phosphate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 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
-
- 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)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR9511861A FR2739620B1 (fr) | 1995-10-09 | 1995-10-09 | Nouveaux derives de la 5-0-desosaminyl 6-o-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs |
Publications (1)
Publication Number | Publication Date |
---|---|
AP888A true AP888A (en) | 2000-11-10 |
Family
ID=9483377
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
APAP/P/1998/001216A AP888A (en) | 1995-10-09 | 1996-10-08 | Novel 5-0-deosaminyl 6-0-methyl erythronolide derivatives, preparation method therefor and use thereof for preparing biologically active materials. |
Country Status (33)
Country | Link |
---|---|
US (1) | US6011142A (no) |
EP (1) | EP0854879B1 (no) |
JP (1) | JP4327248B2 (no) |
KR (1) | KR100451063B1 (no) |
CN (1) | CN1067401C (no) |
AP (1) | AP888A (no) |
AR (1) | AR004688A1 (no) |
AT (1) | ATE212034T1 (no) |
AU (1) | AU708351B2 (no) |
BG (1) | BG63752B1 (no) |
BR (1) | BR9610959A (no) |
CA (1) | CA2231562C (no) |
CZ (1) | CZ293430B6 (no) |
DE (1) | DE69618607T2 (no) |
DK (1) | DK0854879T3 (no) |
EA (1) | EA000765B1 (no) |
EE (1) | EE03878B1 (no) |
ES (1) | ES2171722T3 (no) |
FR (1) | FR2739620B1 (no) |
GE (1) | GEP20032899B (no) |
HU (1) | HUP9900136A3 (no) |
IL (1) | IL123613A0 (no) |
MX (1) | MX9802655A (no) |
NO (1) | NO312592B1 (no) |
PL (1) | PL183645B1 (no) |
PT (1) | PT854879E (no) |
RO (1) | RO118874B1 (no) |
SI (1) | SI0854879T1 (no) |
SK (1) | SK283619B6 (no) |
TR (1) | TR199800624T1 (no) |
UA (1) | UA52621C2 (no) |
WO (1) | WO1997013774A2 (no) |
ZA (1) | ZA966666B (no) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US6590083B1 (en) | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
KR20020007374A (ko) * | 1999-04-16 | 2002-01-26 | 추후제출 | 매크롤라이드 항감염제 |
WO2000062783A2 (en) | 1999-04-16 | 2000-10-26 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
GB0031312D0 (en) * | 2000-12-21 | 2001-02-07 | Glaxo Group Ltd | Macrolides |
EP2664331B1 (en) | 2003-03-10 | 2015-09-16 | Merck Sharp & Dohme Corp. | Novel Antibacterial Agents |
EP2214484A4 (en) * | 2007-10-25 | 2013-01-02 | Cempra Pharmaceuticals Inc | PROCESS FOR PREPARING ANTIBACTERIAL MAKROLIDE AGENTS |
JP5602748B2 (ja) * | 2008-10-24 | 2014-10-08 | センプラ ファーマシューティカルズ,インコーポレイテッド | トリアゾール含有マクロライドを用いた生体防御 |
US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
AU2010292010B2 (en) | 2009-09-10 | 2016-01-07 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and MAC diseases |
BR112012023950A2 (pt) | 2010-03-22 | 2016-07-05 | Cempra Pharmaceuticals Inc | formas cristalinas de um macrolídeo, e usos dos mesmos |
WO2011146829A1 (en) | 2010-05-20 | 2011-11-24 | Cempra Pharmaceuticals, Inc. | Processes for preparing macrolides and ketolides and intermediates therefor |
KR20130120458A (ko) | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
KR20140139083A (ko) | 2012-03-27 | 2014-12-04 | 셈프라 파마슈티컬스, 인크. | 마크롤라이드계 항생제를 투여하기 위한 비경구 제제 |
JP6426696B2 (ja) | 2013-03-14 | 2018-11-21 | センプラ ファーマシューティカルズ,インコーポレイテッド | 呼吸器疾患の治療のための方法および製剤 |
RU2015138797A (ru) | 2013-03-15 | 2017-04-24 | Семпра Фармасьютикалс, Инк. | Конвергентные способы получения макролидных антибактериальных агентов |
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FR2692579A1 (fr) * | 1992-06-19 | 1993-12-24 | Roussel Uclaf | Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments. |
EP0619320A1 (en) * | 1991-12-27 | 1994-10-12 | Taisho Pharmaceutical Co. Ltd | 5-o-desosaminylerythronolide derivative |
EP0638585A1 (en) * | 1992-04-22 | 1995-02-15 | Taisho Pharmaceutical Co. Ltd | 5-o-desosaminylerythronolide a derivative |
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US4742049A (en) * | 1986-06-04 | 1988-05-03 | Abbott Laboratories | Semisynthetic erythromycin antibiotics |
PT86800B (pt) * | 1987-02-24 | 1992-05-29 | Beecham Group Plc | Processo para a preparacao de derivados de eritromicina |
CA2154550A1 (en) * | 1993-01-26 | 1994-08-04 | Yoko Misawa | 5-o-desosaminylerythronolide derivatives |
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1995
- 1995-10-09 FR FR9511861A patent/FR2739620B1/fr not_active Expired - Fee Related
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1996
- 1996-08-06 ZA ZA9606666A patent/ZA966666B/xx unknown
- 1996-08-10 UA UA98041836A patent/UA52621C2/uk unknown
- 1996-10-07 AR ARP960104634A patent/AR004688A1/es not_active Application Discontinuation
- 1996-10-08 ES ES96933501T patent/ES2171722T3/es not_active Expired - Lifetime
- 1996-10-08 DE DE69618607T patent/DE69618607T2/de not_active Expired - Lifetime
- 1996-10-08 AP APAP/P/1998/001216A patent/AP888A/en active
- 1996-10-08 SK SK431-98A patent/SK283619B6/sk unknown
- 1996-10-08 DK DK96933501T patent/DK0854879T3/da active
- 1996-10-08 US US09/051,378 patent/US6011142A/en not_active Ceased
- 1996-10-08 AU AU72208/96A patent/AU708351B2/en not_active Expired
- 1996-10-08 KR KR10-1998-0702581A patent/KR100451063B1/ko not_active IP Right Cessation
- 1996-10-08 BR BR9610959A patent/BR9610959A/pt not_active Application Discontinuation
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- 1996-10-08 IL IL12361396A patent/IL123613A0/xx not_active IP Right Cessation
- 1996-10-08 CA CA002231562A patent/CA2231562C/fr not_active Expired - Lifetime
- 1996-10-08 EA EA199800280A patent/EA000765B1/ru not_active IP Right Cessation
- 1996-10-08 GE GEAP19964227A patent/GEP20032899B/en unknown
- 1996-10-08 WO PCT/FR1996/001567 patent/WO1997013774A2/fr not_active Application Discontinuation
- 1996-10-08 JP JP51476697A patent/JP4327248B2/ja not_active Expired - Lifetime
- 1996-10-08 EP EP96933501A patent/EP0854879B1/fr not_active Expired - Lifetime
- 1996-10-08 RO RO98-00826A patent/RO118874B1/ro unknown
- 1996-10-08 TR TR1998/00624T patent/TR199800624T1/xx unknown
- 1996-10-08 PL PL96326001A patent/PL183645B1/pl not_active IP Right Cessation
- 1996-10-08 AT AT96933501T patent/ATE212034T1/de active
- 1996-10-08 CZ CZ19981055A patent/CZ293430B6/cs not_active IP Right Cessation
- 1996-10-08 HU HU9900136A patent/HUP9900136A3/hu unknown
- 1996-10-08 CN CN96197514A patent/CN1067401C/zh not_active Expired - Lifetime
- 1996-10-08 PT PT96933501T patent/PT854879E/pt unknown
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1998
- 1998-03-25 BG BG102350A patent/BG63752B1/bg unknown
- 1998-04-03 MX MX9802655A patent/MX9802655A/es unknown
- 1998-04-08 NO NO19981630A patent/NO312592B1/no not_active IP Right Cessation
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EP0619320A1 (en) * | 1991-12-27 | 1994-10-12 | Taisho Pharmaceutical Co. Ltd | 5-o-desosaminylerythronolide derivative |
EP0638585A1 (en) * | 1992-04-22 | 1995-02-15 | Taisho Pharmaceutical Co. Ltd | 5-o-desosaminylerythronolide a derivative |
FR2692579A1 (fr) * | 1992-06-19 | 1993-12-24 | Roussel Uclaf | Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments. |
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