BG64099B1 - 3'-n-оксидни, 3'-n-диметиламинови, 9-оксимни производни на еритромицин а - Google Patents

3'-n-оксидни, 3'-n-диметиламинови, 9-оксимни производни на еритромицин а Download PDF

Info

Publication number: BG64099B1
Authority: BG; Bulgaria
Prior art keywords: group; compound; lower alkyl; oxime; oxide
Prior art date: 1997-02-13

Application number

BG103673A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103673A (en

Inventor

Yi-Yin Ku

David Riley

Original Assignee

Abbott Laboratories

Priority date (The priority date 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 date listed.)

1997-02-13

Filing date

1999-08-20

Publication date

2003-12-31

1999-08-20 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2000-02-29 Publication of BG103673A publication Critical patent/BG103673A/xx

2003-12-31 Publication of BG64099B1 publication Critical patent/BG64099B1/bg

Links

238000000034 method Methods 0.000 claims abstract description 26
238000002360 preparation method Methods 0.000 claims abstract description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 18
238000006243 chemical reaction Methods 0.000 claims abstract description 17
125000000217 alkyl group Chemical group 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 30
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 claims description 21
150000002923 oximes Chemical class 0.000 claims description 21
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 18
229960003276 erythromycin Drugs 0.000 claims description 18
125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
229930006677 Erythromycin A Natural products 0.000 claims description 16
125000004429 atom Chemical group 0.000 claims description 12
125000003118 aryl group Chemical group 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
239000002585 base Substances 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000004430 oxygen atom Chemical group O* 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
125000002877 alkyl aryl group Chemical group 0.000 claims description 7
230000029936 alkylation Effects 0.000 claims description 7
238000005804 alkylation reaction Methods 0.000 claims description 7
150000001340 alkali metals Chemical class 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
239000002168 alkylating agent Substances 0.000 claims description 5
229940100198 alkylating agent Drugs 0.000 claims description 5
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
239000007800 oxidant agent Substances 0.000 claims description 4
239000003880 polar aprotic solvent Substances 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
238000007254 oxidation reaction Methods 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
238000010992 reflux Methods 0.000 claims description 3
125000004849 alkoxymethyl group Chemical group 0.000 claims description 2
KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 2
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 description 2
230000003647 oxidation Effects 0.000 claims 2
GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 claims 1
229940125758 compound 15 Drugs 0.000 claims 1
230000000694 effects Effects 0.000 claims 1
230000008030 elimination Effects 0.000 abstract 1
238000003379 elimination reaction Methods 0.000 abstract 1
AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([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 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 23
229960002626 clarithromycin Drugs 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
238000001819 mass spectrum Methods 0.000 description 18
239000000243 solution Substances 0.000 description 17
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 15
-1 diphenylbenzyl Chemical group 0.000 description 14
239000007787 solid Substances 0.000 description 14
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
239000000203 mixture Substances 0.000 description 9
125000004432 carbon atom Chemical group C* 0.000 description 8
238000007069 methylation reaction Methods 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
239000003054 catalyst Substances 0.000 description 7
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
239000000047 product Substances 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
125000003545 alkoxy group Chemical group 0.000 description 5
230000011987 methylation Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
239000012043 crude product Substances 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
238000004128 high performance liquid chromatography Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
150000003839 salts Chemical group 0.000 description 3
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 2
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 2
PLUBXMRUUVWRLT-UHFFFAOYSA-N Ethyl methanesulfonate Chemical compound CCOS(C)(=O)=O PLUBXMRUUVWRLT-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
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 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
239000007868 Raney catalyst Substances 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
239000002253 acid Substances 0.000 description 2
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000004440 column chromatography Methods 0.000 description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
229940008406 diethyl sulfate Drugs 0.000 description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 2
HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 2
238000004811 liquid chromatography Methods 0.000 description 2
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
HSZCZNFXUDYRKD-UHFFFAOYSA-M lithium iodide Chemical compound [Li+].[I-] HSZCZNFXUDYRKD-UHFFFAOYSA-M 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
229940102396 methyl bromide Drugs 0.000 description 2
IHYNKGRWCDKNEG-UHFFFAOYSA-N n-(4-bromophenyl)-2,6-dihydroxybenzamide Chemical compound OC1=CC=CC(O)=C1C(=O)NC1=CC=C(Br)C=C1 IHYNKGRWCDKNEG-UHFFFAOYSA-N 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical compound CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 2
229910000105 potassium hydride Inorganic materials 0.000 description 2
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000746 purification Methods 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-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
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 1
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 1
KYTWXIARANQMCA-RWJQBGPGSA-N (3r,4s,5s,6r,7r,9r,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-oxacyclotetradecan-2 Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=NO)[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-RWJQBGPGSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
VLXSIHLNPYRFFN-UHFFFAOYSA-N 1,4-dioxane;methanol Chemical compound OC.C1COCCO1 VLXSIHLNPYRFFN-UHFFFAOYSA-N 0.000 description 1
BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
125000006420 1-fluorocyclopropyl group Chemical group [H]C1([H])C([H])([H])C1(F)* 0.000 description 1
125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
125000006040 2-hexenyl group Chemical group 0.000 description 1
125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
125000006041 3-hexenyl group Chemical group 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
125000006042 4-hexenyl group Chemical group 0.000 description 1
125000006043 5-hexenyl group Chemical group 0.000 description 1
206010067484 Adverse reaction Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
125000000815 N-oxide group Chemical group 0.000 description 1
229910000990 Ni alloy Inorganic materials 0.000 description 1
CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
ORWKVZNEPHTCQE-UHFFFAOYSA-N acetic formic anhydride Chemical compound CC(=O)OC=O ORWKVZNEPHTCQE-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
230000006838 adverse reaction Effects 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
125000002029 aromatic hydrocarbon group Chemical group 0.000 description 1
125000005228 aryl sulfonate group Chemical group 0.000 description 1
HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000010520 demethylation reaction Methods 0.000 description 1
238000003386 deoximation reaction Methods 0.000 description 1
150000008050 dialkyl sulfates Chemical class 0.000 description 1
JYCKNDWZDXGNBW-UHFFFAOYSA-N dipropyl sulfate Chemical compound CCCOS(=O)(=O)OCCC JYCKNDWZDXGNBW-UHFFFAOYSA-N 0.000 description 1
WHQLQYRFIHPMNA-UHFFFAOYSA-N ethyl acetate;oxolane Chemical compound C1CCOC1.CCOC(C)=O WHQLQYRFIHPMNA-UHFFFAOYSA-N 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
125000001475 halogen functional group Chemical group 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
FPBMTPLRBAEUMV-UHFFFAOYSA-N nickel sodium Chemical compound [Na][Ni] FPBMTPLRBAEUMV-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
125000003884 phenylalkyl group Chemical group 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
YAGXZDADEJXXMM-UHFFFAOYSA-M potassium chloride hydrate Chemical compound [OH-].Cl.[K+] YAGXZDADEJXXMM-UHFFFAOYSA-M 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
DKORSYDQYFVQNS-UHFFFAOYSA-N propyl methanesulfonate Chemical compound CCCOS(C)(=O)=O DKORSYDQYFVQNS-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
ZDYVRSLAEXCVBX-UHFFFAOYSA-N pyridinium p-toluenesulfonate Chemical compound C1=CC=[NH+]C=C1.CC1=CC=C(S([O-])(=O)=O)C=C1 ZDYVRSLAEXCVBX-UHFFFAOYSA-N 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000000547 substituted alkyl group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
229910052720 vanadium Inorganic materials 0.000 description 1
LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

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)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BG103673A 1997-02-13 1999-08-20 3'-n-оксидни, 3'-n-диметиламинови, 9-оксимни производни на еритромицин а BG64099B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US08/800,009 US5864023A (en)	1997-02-13	1997-02-13	3'-N'oxide, 3'-n-dimethylamine, 9-oxime erythromycin a derivatives
PCT/US1998/001929 WO1998035976A1 (en)	1997-02-13	1998-02-03	3'-n-oxide, 3'-n-dimethylamine, 9-oxime erythromycin a derivatives

Publications (2)

Publication Number	Publication Date
BG103673A BG103673A (en)	2000-02-29
BG64099B1 true BG64099B1 (bg)	2003-12-31

Family

ID=25177295

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103673A BG64099B1 (bg)	1997-02-13	1999-08-20	3'-n-оксидни, 3'-n-диметиламинови, 9-оксимни производни на еритромицин а

Country Status (25)

Country	Link
US (1)	US5864023A (de)
EP (1)	EP0966477B1 (de)
JP (1)	JP2001512456A (de)
KR (1)	KR100561326B1 (de)
CN (1)	CN1326865C (de)
AR (1)	AR012032A1 (de)
AT (1)	ATE252108T1 (de)
AU (1)	AU725274B2 (de)
BG (1)	BG64099B1 (de)
BR (1)	BR9807349A (de)
CA (1)	CA2279932C (de)
CZ (1)	CZ294481B6 (de)
DE (1)	DE69818977T2 (de)
DK (1)	DK0966477T3 (de)
ES (1)	ES2212266T3 (de)
HU (1)	HUP0001330A3 (de)
IL (1)	IL130697A0 (de)
NO (1)	NO993876L (de)
NZ (1)	NZ336482A (de)
PL (1)	PL187357B1 (de)
PT (1)	PT966477E (de)
SK (1)	SK284157B6 (de)
TR (1)	TR199901874T2 (de)
WO (1)	WO1998035976A1 (de)
ZA (1)	ZA98986B (de)

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KR100317907B1 (ko) *	1998-11-24	2001-12-24	김 완 주	신규한 중간체, 이를 이용한 마크로라이드계 항생제의제조방법
US6437106B1 (en)	1999-06-24	2002-08-20	Abbott Laboratories	Process for preparing 6-o-substituted erythromycin derivatives
KR20010008496A (ko) *	1999-07-01	2001-02-05	유충식	6-오-메틸 에리트로마이신의 제조방법
KR100336447B1 (ko) *	1999-11-24	2002-05-15	민경윤	클라리스로마이신의 개선된 제조방법
PT1254146E (pt) *	1999-12-16	2005-10-31	Teva Pharma	Processos de preparacao de polimeros de claritromicina e novo polimorfo iv
PL356645A1 (en) *	2000-01-11	2004-06-28	Teva Pharmaceutical Industries Ltd.	Processes for preparing clarithromycin polymorphs
US6565882B2 (en) *	2000-02-24	2003-05-20	Advancis Pharmaceutical Corp	Antibiotic composition with inhibitor
US6544555B2 (en)	2000-02-24	2003-04-08	Advancis Pharmaceutical Corp.	Antibiotic product, use and formulation thereof
AU2578701A (en)	2000-02-29	2001-09-12	Teva Pharma	Processes for preparing clarithromycin and clarithromycin intermediate, essentially oxime-free clarithromycin, and pharmaceutical composition comprising the same
CN1193036C (zh) *	2000-03-15	2005-03-16	韩美药品工业株式会社	制备甲红霉素－克拉霉素ⅱ型晶体的方法
KR20000037126A (ko) *	2000-04-08	2000-07-05	김용규	6-메틸 에리스로마이신 ａ의 제조방법
US20020068078A1 (en) *	2000-10-13	2002-06-06	Rudnic Edward M.	Antifungal product, use and formulation thereof
US6541014B2 (en) *	2000-10-13	2003-04-01	Advancis Pharmaceutical Corp.	Antiviral product, use and formulation thereof
US20020197314A1 (en) *	2001-02-23	2002-12-26	Rudnic Edward M.	Anti-fungal composition
EP1648418A4 (de) *	2003-07-21	2011-11-16	Middlebrook Pharmaceuticals Inc	Antibiotisches produkt, seine verwendung und formulierung
EP1648415A4 (de) *	2003-07-21	2011-11-16	Middlebrook Pharmaceuticals Inc	Antibiotisches produkt, seine verwendung und formulierung
CA2533292C (en) *	2003-07-21	2013-12-31	Advancis Pharmaceutical Corporation	Antibiotic product, use and formulation thereof
WO2005016311A1 (en) *	2003-08-11	2005-02-24	Advancis Pharmaceutical Corporation	Robust pellet
CA2535398C (en) *	2003-08-12	2013-11-12	Advancis Pharmaceuticals Corporation	Antibiotic product, use and formulation thereof
EP1658034A4 (de) *	2003-08-29	2011-06-22	Middlebrook Pharmaceuticals Inc	Antibiotisches produkt, seine verwendung und formulierung
WO2005027877A1 (en) *	2003-09-15	2005-03-31	Advancis Pharmaceutical Corporation	Antibiotic product, use and formulation thereof
AU2004308419B2 (en) *	2003-12-24	2011-06-02	Victory Pharma, Inc.	Enhanced absorption of modified release dosage forms
US8715727B2 (en) *	2004-07-02	2014-05-06	Shionogi Inc.	Tablet for pulsed delivery
US7694523B2 (en) *	2004-07-19	2010-04-13	Earthrenew, Inc.	Control system for gas turbine in material treatment unit
US8778924B2 (en) *	2006-12-04	2014-07-15	Shionogi Inc.	Modified release amoxicillin products
US8357394B2 (en)	2005-12-08	2013-01-22	Shionogi Inc.	Compositions and methods for improved efficacy of penicillin-type antibiotics
US8299052B2 (en)	2006-05-05	2012-10-30	Shionogi Inc.	Pharmaceutical compositions and methods for improved bacterial eradication
US20090054634A1 (en) *	2007-08-09	2009-02-26	Vinod Kumar Kansal	Process for the preparation of clarithromycin

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US4331803A (en) *	1980-06-04	1982-05-25	Taisho Pharmaceutical Co., Ltd.	Novel erythromycin compounds
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
US4670549A (en) *	1985-03-18	1987-06-02	Taisho Pharmaceutical Co., Ltd.	Method for selective methylation of erythromycin a derivatives
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
EP0254534A3 (de) *	1986-07-24	1991-04-17	William S. Robinson	Erythromycin-Derivate und Zusammensetzungen und ihre Verwendung, um Virusreplikation und Krankheiten zu Inhibieren
DE3782994T2 (de) *	1986-09-18	1993-04-08	Taisho Pharma Co Ltd	Erythromycin-a-derivate und verfahren zu ihrer herstellung.
KR960000434B1 (ko) *	1986-12-17	1996-01-06	다이쇼 세이야꾸 가부시끼가이샤	에리스로마이신 a유도체 및 그의 제조 방법
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

1997
- 1997-02-13 US US08/800,009 patent/US5864023A/en not_active Expired - Lifetime
1998
- 1998-02-03 IL IL13069798A patent/IL130697A0/xx unknown
- 1998-02-03 CN CNB988023784A patent/CN1326865C/zh not_active Expired - Fee Related
- 1998-02-03 AT AT98904822T patent/ATE252108T1/de not_active IP Right Cessation
- 1998-02-03 KR KR1019997007251A patent/KR100561326B1/ko not_active Expired - Fee Related
- 1998-02-03 CA CA002279932A patent/CA2279932C/en not_active Expired - Fee Related
- 1998-02-03 ES ES98904822T patent/ES2212266T3/es not_active Expired - Lifetime
- 1998-02-03 JP JP53578098A patent/JP2001512456A/ja not_active Ceased
- 1998-02-03 NZ NZ336482A patent/NZ336482A/en unknown
- 1998-02-03 SK SK974-99A patent/SK284157B6/sk not_active IP Right Cessation
- 1998-02-03 HU HU0001330A patent/HUP0001330A3/hu unknown
- 1998-02-03 WO PCT/US1998/001929 patent/WO1998035976A1/en not_active Ceased
- 1998-02-03 BR BR9807349-4A patent/BR9807349A/pt not_active Application Discontinuation
- 1998-02-03 PT PT98904822T patent/PT966477E/pt unknown
- 1998-02-03 CZ CZ19992704A patent/CZ294481B6/cs not_active IP Right Cessation
- 1998-02-03 DE DE69818977T patent/DE69818977T2/de not_active Expired - Fee Related
- 1998-02-03 PL PL98335301A patent/PL187357B1/pl not_active IP Right Cessation
- 1998-02-03 EP EP98904822A patent/EP0966477B1/de not_active Expired - Lifetime
- 1998-02-03 AU AU62608/98A patent/AU725274B2/en not_active Ceased
- 1998-02-03 DK DK98904822T patent/DK0966477T3/da active
- 1998-02-03 TR TR1999/01874T patent/TR199901874T2/xx unknown
- 1998-02-06 ZA ZA98986A patent/ZA98986B/xx unknown
- 1998-02-10 AR ARP980100584A patent/AR012032A1/es active IP Right Grant
1999
- 1999-08-11 NO NO993876A patent/NO993876L/no not_active Application Discontinuation
- 1999-08-20 BG BG103673A patent/BG64099B1/bg unknown

Also Published As

Publication number	Publication date
DE69818977T2 (de)	2004-08-12
EP0966477B1 (de)	2003-10-15
PT966477E (pt)	2004-03-31
AU725274B2 (en)	2000-10-12
BG103673A (en)	2000-02-29
CN1246864A (zh)	2000-03-08
HUP0001330A3 (en)	2000-09-28
CA2279932C (en)	2008-04-22
NZ336482A (en)	2001-02-23
AR012032A1 (es)	2000-09-27
SK284157B6 (sk)	2004-10-05
EP0966477A1 (de)	1999-12-29
HUP0001330A2 (hu)	2000-08-28
KR100561326B1 (ko)	2006-03-16
CZ294481B6 (cs)	2005-01-12
NO993876D0 (no)	1999-08-11
ZA98986B (en)	1998-08-05
WO1998035976A1 (en)	1998-08-20
SK97499A3 (en)	2000-01-18
BR9807349A (pt)	2000-04-25
PL187357B1 (pl)	2004-06-30
US5864023A (en)	1999-01-26
DK0966477T3 (da)	2004-02-23
PL335301A1 (en)	2000-04-10
JP2001512456A (ja)	2001-08-21
ES2212266T3 (es)	2004-07-16
ATE252108T1 (de)	2003-11-15
IL130697A0 (en)	2000-06-01
TR199901874T2 (xx)	2000-04-21
KR20000070985A (ko)	2000-11-25
DE69818977D1 (en)	2003-11-20
NO993876L (no)	1999-08-11
CA2279932A1 (en)	1998-08-20
CN1326865C (zh)	2007-07-18
CZ270499A3 (cs)	1999-11-17
AU6260898A (en)	1998-09-08

Publication	Publication Date	Title
US5864023A (en)	1999-01-26	3'-N'oxide, 3'-n-dimethylamine, 9-oxime erythromycin a derivatives
USRE39383E1 (en)	2006-11-07	Process for 6-O-alkylation of erythromycin derivatives
EP0891370B1 (de)	2002-12-04	2'-geschützter 3'-dimethylamin, 9-etheroxim erythromycin a derivate
EP1040107B1 (de)	2003-01-29	6-o-alkyl erythronolid-b derivate
EP0158467B1 (de)	1989-07-05	Methode zur selektiven Methylierung von Erythromycin A-Derivaten
KR100336447B1 (ko)	2002-05-15	클라리스로마이신의 개선된 제조방법
MXPA99007519A (en)	2000-04-24	3'-n-oxide, 3'-n-dimethylamine, 9-oxime erythromycin a derivatives
KR100330973B1 (ko)	2002-04-01	클라리스로마이신의 제조방법 및 이에 사용되는 중간체
KR20010032613A (ko)	2001-04-25	6-ｏ-알킬 에리트로마이신 ｃ의 화학적 합성 방법
CA2250736C (en)	2006-03-28	2'-protected 3'-dimethylamine, 9-etheroxime erythromycin a derivatives
WO2005021567A1 (en)	2005-03-10	O-alkyl macrolide and azalide derivatives and regioselective process for their preparation
MXPA00005402A (en)	2001-07-03	6-o-alkyl derivatives of erythronolide b
MXPA00005404A (en)	2001-07-03	Chemical synthesis of 6-o-alkyl erythromycin c