DD216017A5 - Verfahren zur herstellung von 4"-epi-9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a - Google Patents
Verfahren zur herstellung von 4"-epi-9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a Download PDFInfo
- Publication number
- DD216017A5 DD216017A5 DD83256672A DD25667283A DD216017A5 DD 216017 A5 DD216017 A5 DD 216017A5 DD 83256672 A DD83256672 A DD 83256672A DD 25667283 A DD25667283 A DD 25667283A DD 216017 A5 DD216017 A5 DD 216017A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- aza
- epi
- deoxo
- desoxo
- homoerythromycin
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 8
- 238000000034 method Methods 0.000 claims abstract description 34
- 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 abstract description 21
- 229960003276 erythromycin Drugs 0.000 claims abstract description 19
- 229930006677 Erythromycin A Natural products 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- 239000012442 inert solvent Substances 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 13
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 229910000564 Raney nickel Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 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 claims description 6
- 229910000510 noble metal Inorganic materials 0.000 claims description 6
- 230000009467 reduction Effects 0.000 claims description 6
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 claims description 6
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- 230000001590 oxidative effect Effects 0.000 claims description 4
- 230000008569 process Effects 0.000 claims description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
- 238000003797 solvolysis reaction Methods 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000003586 protic polar solvent Substances 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 150000002576 ketones Chemical class 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 claims description 2
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims 1
- CCAFPWNGIUBUSD-UHFFFAOYSA-N diethyl sulfoxide Chemical compound CCS(=O)CC CCAFPWNGIUBUSD-UHFFFAOYSA-N 0.000 claims 1
- 230000001035 methylating effect Effects 0.000 claims 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 208000035143 Bacterial infection Diseases 0.000 abstract 1
- 208000022362 bacterial infectious disease Diseases 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000047 product Substances 0.000 description 58
- 150000001875 compounds Chemical class 0.000 description 35
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000006260 foam Substances 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 16
- 239000000203 mixture Substances 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000010410 layer Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 239000012044 organic layer Substances 0.000 description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- -1 e.g. Substances 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 244000005700 microbiome Species 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 239000002552 dosage form Substances 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 230000011987 methylation Effects 0.000 description 4
- 238000007069 methylation reaction Methods 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 150000002923 oximes Chemical class 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 235000000346 sugar Nutrition 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- YHVUVJYEERGYNU-UHFFFAOYSA-N 4',8-Di-Me ether-5,7,8-Trihydroxy-3-(4-hydroxybenzyl)-4-chromanone Natural products COC1(C)CC(O)OC(C)C1O YHVUVJYEERGYNU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-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
- 101001081176 Homo sapiens Hyaluronan mediated motility receptor Proteins 0.000 description 3
- 102100027735 Hyaluronan mediated motility receptor Human genes 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
- 125000001589 carboacyl group Chemical group 0.000 description 3
- AJSDVNKVGFVAQU-BIIVOSGPSA-N cladinose Chemical compound O=CC[C@@](C)(OC)[C@@H](O)[C@H](C)O AJSDVNKVGFVAQU-BIIVOSGPSA-N 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 239000012634 fragment Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 150000008163 sugars Chemical class 0.000 description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-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
- 241001465754 Metazoa Species 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000003937 drug carrier Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052763 palladium 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
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UXDNUPFGRUGPKK-XBWOTNPQSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecane-7,15-d Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC(=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 UXDNUPFGRUGPKK-XBWOTNPQSA-N 0.000 description 1
- SIQMKRANFZMVQT-UHFFFAOYSA-N 2-ethyl-1-oxa-6-azacyclopentadecan-15-one Chemical class CCC1CCCNCCCCCCCCC(=O)O1 SIQMKRANFZMVQT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000606768 Haemophilus influenzae Species 0.000 description 1
- 229910052689 Holmium Inorganic materials 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 238000003436 Schotten-Baumann reaction Methods 0.000 description 1
- 241000270295 Serpentes Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 235000019445 benzyl alcohol Nutrition 0.000 description 1
- 238000004166 bioassay Methods 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000006392 deoxygenation reaction Methods 0.000 description 1
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical compound C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 150000002148 esters Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940047650 haemophilus influenzae Drugs 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000012022 methylating agents Substances 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 101150032584 oxy-4 gene Proteins 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000006201 parenteral dosage form Substances 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000006485 reductive methylation reaction Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
-
- 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
-
- 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)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Veterinary Medicine (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Cosmetics (AREA)
- Developing Agents For Electrophotography (AREA)
- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44197982A | 1982-11-15 | 1982-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD216017A5 true DD216017A5 (de) | 1984-11-28 |
Family
ID=23755068
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD83256672A DD216017A5 (de) | 1982-11-15 | 1983-11-14 | Verfahren zur herstellung von 4"-epi-9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a |
Country Status (26)
| Country | Link |
|---|---|
| EP (1) | EP0109253B1 (en, 2012) |
| JP (1) | JPS59104398A (en, 2012) |
| KR (1) | KR850000968B1 (en, 2012) |
| AT (1) | ATE30237T1 (en, 2012) |
| AU (1) | AU544790B2 (en, 2012) |
| CA (1) | CA1239639A (en, 2012) |
| CS (1) | CS241069B2 (en, 2012) |
| DD (1) | DD216017A5 (en, 2012) |
| DE (1) | DE3374065D1 (en, 2012) |
| DK (1) | DK159322C (en, 2012) |
| EG (1) | EG16641A (en, 2012) |
| ES (2) | ES527249A0 (en, 2012) |
| FI (1) | FI72980C (en, 2012) |
| GR (1) | GR79425B (en, 2012) |
| GT (1) | GT198304062A (en, 2012) |
| HU (1) | HU193886B (en, 2012) |
| IE (1) | IE56234B1 (en, 2012) |
| IL (1) | IL70228A (en, 2012) |
| NO (1) | NO160262C (en, 2012) |
| NZ (1) | NZ206259A (en, 2012) |
| PH (2) | PH19293A (en, 2012) |
| PL (2) | PL143281B1 (en, 2012) |
| PT (1) | PT77645B (en, 2012) |
| SU (1) | SU1272996A3 (en, 2012) |
| YU (2) | YU43198B (en, 2012) |
| ZA (1) | ZA838460B (en, 2012) |
Families Citing this family (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0136831B1 (en) * | 1983-09-06 | 1988-11-09 | Pfizer Inc. | Azahomoerythromycin b derivatives and intermediates thereof |
| US4465674A (en) * | 1983-09-06 | 1984-08-14 | Pfizer Inc. | Azahomoerythromycin D derivative and intermediates therefor |
| RO107257B1 (ro) * | 1987-07-09 | 1993-10-30 | Pfizer | Procedeu de obtinere a unui dihidrat de azitromicina, cristalin |
| WO1989002271A1 (en) * | 1987-09-10 | 1989-03-23 | Pfizer | Azithromycin and derivatives as antiprotozoal agents |
| 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 |
| SI8911498B (sl) * | 1989-07-26 | 1998-10-31 | Pliva | Postopek za pripravo derivatov tilozina |
| 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 |
| CA2064634C (en) * | 1991-04-04 | 1998-08-04 | James V. Heck | 9-deoxo-8a-aza-8a-homoerythromycin a derivatives modified at the 4"- and8a-positions |
| CA2064985A1 (en) * | 1991-04-05 | 1992-10-06 | Robert R. Wilkening | 8a-aza-8a-homoertyhromycin cyclic lactams |
| CA2065222A1 (en) * | 1991-04-09 | 1992-10-10 | Robert R. Wilkening | Process for the preparation of 8a-aza-8a-homoerythromycin cyclic iminoethers |
| US5189159A (en) * | 1992-04-02 | 1993-02-23 | Merck & Co., Inc. | 8a-AZA-8a-homoerythromycin cyclic iminoethers |
| CA2065674A1 (en) * | 1991-04-10 | 1992-10-11 | Robert R. Wilkening | 8a-aza-8a-homoerythromycin cyclic iminoethers |
| CA2065218A1 (en) * | 1991-04-11 | 1992-10-12 | Robert R. Wilkening | Process for the preparation of 9-deoxo-8a-aza-8a-homoerythromycin a and its 8a-alkyl derivatives |
| EP0515141A1 (en) * | 1991-05-20 | 1992-11-25 | Merck & Co. Inc. | Novel process for the preparation of 8A-aza-8A-homoerythromycin cyclic lactams |
| EP0549040A1 (en) * | 1991-12-20 | 1993-06-30 | Merck & Co. Inc. | Methods of making 4" derivatives of 9-deoxo-8a-aza-8a-alkyl-8a-homoerythromycin A |
| US5215980A (en) * | 1992-01-17 | 1993-06-01 | Merck & Co., Inc. | 10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof |
| US5210235A (en) * | 1992-08-26 | 1993-05-11 | Merck & Co., Inc. | Methods of elaborating erythromycin fragments into amine-containing fragments of azalide antibiotics |
| HRP930014A2 (en) * | 1993-01-08 | 1994-08-31 | Pliva Pharm & Chem Works | 9-deoxo-9a-aza-11-deoxy-9a-homoeritromycin a 9a, 11-cyclic carbamates |
| US5332807A (en) * | 1993-04-14 | 1994-07-26 | Merck & Co., Inc. | Process of producing 8A- and 9A-azalide antibiotics |
| WO1995030422A1 (en) * | 1994-05-06 | 1995-11-16 | Pfizer Inc. | Controlled-release dosage forms of azithromycin |
| PT840606E (pt) * | 1995-06-29 | 2000-11-30 | Texas Biotechnology Corp | Moleculas pequenas di-e trivalentes inibidoras de selectina |
| HRP960497B1 (en) * | 1996-10-28 | 2003-08-31 | Pliva Pharm & Chem Works | 9-n-ethenyl derivatives of 9(s)-erythromycylamine |
| PT102006B (pt) * | 1997-05-19 | 2000-06-30 | Hovione Sociedade Quimica S A | Novo processo de preparacao de azitromicina |
| TW546302B (en) * | 1998-05-08 | 2003-08-11 | Biochemie Sa | Improvements in macrolide production |
| US6043227A (en) * | 1998-08-19 | 2000-03-28 | Pfizer Inc. | C11 carbamates of macrolide antibacterials |
| EP1437360A3 (en) * | 1998-08-19 | 2005-04-06 | Pfizer Products Inc. | C11 Carbamates of macrolide antibacterials |
| US6764996B1 (en) | 1999-08-24 | 2004-07-20 | Abbott Laboratories | 9a-azalides with antibacterial activity |
| AU6748500A (en) * | 1999-08-24 | 2001-03-19 | Abbott Laboratories | 9a-azalides with antibacterial activity |
| WO2001049697A1 (en) * | 2000-01-04 | 2001-07-12 | Teva Pharmaceutical Industries Ltd. | Preparation method of azithromycin dihydrate |
| JP2004506664A (ja) | 2000-08-23 | 2004-03-04 | ウォックハート・リミテッド | 無水アジトロマイシンの製造法 |
| US6852262B2 (en) | 2002-05-09 | 2005-02-08 | The Gillette Company | Insert molding razor cartridges |
| 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 |
| CN1889932A (zh) | 2003-12-04 | 2007-01-03 | 辉瑞产品公司 | 制备药用多颗粒的方法 |
| CA2549225A1 (en) | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Spray-congeal process using an extruder for preparing multiparticulate crystalline drug compositions containing preferably a poloxamer and a glyceride |
| WO2005053652A1 (en) | 2003-12-04 | 2005-06-16 | Pfizer Products Inc. | Multiparticulate crystalline drug compositions containing a poloxamer and a glyceride |
| BRPI0416534A (pt) | 2003-12-04 | 2007-01-09 | Pfizer Prod Inc | composições multiparticuladas com estabilidade melhorada |
| US6984403B2 (en) | 2003-12-04 | 2006-01-10 | Pfizer Inc. | Azithromycin dosage forms with reduced side effects |
| RU2256665C1 (ru) * | 2004-01-29 | 2005-07-20 | Открытое акционерное общество Акционерное Курганское общество медицинских препаратов и изделий "Синтез" | Способ получения оксима эритромицина |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU43116B (en) * | 1979-04-02 | 1989-04-30 | Pliva Pharm & Chem Works | Process for preparing 11-aza-4-o-cladinosyl-6-o-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one(11-aza-10-deox |
| JPS5788193A (en) * | 1980-11-21 | 1982-06-01 | Pliva Pharm & Chem Works | 11-aza-10-deoxo-10-dihydroerythromycin a, derivatives and manufacture |
| YU43006B (en) * | 1981-03-06 | 1989-02-28 | Pliva Pharm & Chem Works | Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin and derivatives thereof |
| US4382085A (en) * | 1982-03-01 | 1983-05-03 | Pfizer Inc. | 4"-Epi erythromycin A and derivatives thereof as useful antibacterial agents |
-
1983
- 1983-10-21 PH PH29751A patent/PH19293A/en unknown
- 1983-11-09 DE DE8383306815T patent/DE3374065D1/de not_active Expired
- 1983-11-09 AT AT83306815T patent/ATE30237T1/de not_active IP Right Cessation
- 1983-11-09 EP EP83306815A patent/EP0109253B1/en not_active Expired
- 1983-11-10 CA CA000440924A patent/CA1239639A/en not_active Expired
- 1983-11-11 GR GR72951A patent/GR79425B/el unknown
- 1983-11-11 GT GT198304062A patent/GT198304062A/es unknown
- 1983-11-11 PT PT77645A patent/PT77645B/pt unknown
- 1983-11-14 HU HU833902A patent/HU193886B/hu unknown
- 1983-11-14 KR KR1019830005387A patent/KR850000968B1/ko not_active Expired
- 1983-11-14 DD DD83256672A patent/DD216017A5/de not_active IP Right Cessation
- 1983-11-14 SU SU833661803A patent/SU1272996A3/ru active
- 1983-11-14 PL PL1983244557A patent/PL143281B1/pl unknown
- 1983-11-14 AU AU21309/83A patent/AU544790B2/en not_active Expired
- 1983-11-14 FI FI834163A patent/FI72980C/fi not_active IP Right Cessation
- 1983-11-14 ZA ZA838460A patent/ZA838460B/xx unknown
- 1983-11-14 NZ NZ206259A patent/NZ206259A/en unknown
- 1983-11-14 DK DK518683A patent/DK159322C/da not_active IP Right Cessation
- 1983-11-14 IL IL70228A patent/IL70228A/xx not_active IP Right Cessation
- 1983-11-14 PL PL1983250350A patent/PL142601B1/pl unknown
- 1983-11-14 ES ES527249A patent/ES527249A0/es active Granted
- 1983-11-14 NO NO834146A patent/NO160262C/no not_active IP Right Cessation
- 1983-11-14 IE IE2652/83A patent/IE56234B1/en not_active IP Right Cessation
- 1983-11-15 CS CS838455A patent/CS241069B2/cs unknown
- 1983-11-15 EG EG717/83A patent/EG16641A/xx active
- 1983-11-15 JP JP58214928A patent/JPS59104398A/ja active Granted
- 1983-11-15 YU YU2243/83A patent/YU43198B/xx unknown
-
1985
- 1985-02-28 PH PH31922A patent/PH21560A/en unknown
- 1985-05-29 ES ES543638A patent/ES8604257A1/es not_active Expired
- 1985-12-17 YU YU1972/85A patent/YU43425B/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DD216017A5 (de) | Verfahren zur herstellung von 4"-epi-9-desoxo-9a-methyl-9a-aza-9a-homoerythromycin a | |
| DE2618822C3 (de) | Anthracyclin-Glycoside und Verfahren zu deren Herstellung | |
| US4526889A (en) | Epimeric azahomoerythromycin A derivative, intermediates and method of use | |
| JPH01193292A (ja) | Ｎ−メチル１１−アザ−１０−デオキソ−１０−ジヒドロエリスロマイシンａ製造用中間体 | |
| DE2346535B2 (de) | Verfahren zur Herstellung von 7-Dimethylamino-e-desmethyl-e-desoxytetracyclin über 9-tert.Butyl-6-desmethyl-6-desoxytetracyclin | |
| DE2411504C3 (de) | 6'-Substituierte 6'-Desoxylividomycine B, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Arzneimittel | |
| US5023240A (en) | Derivatives of tylosin and 10,11,12,13-tetrahydro tylosin and their use in pharmaceuticals | |
| DD211565A5 (de) | Verfahren zur herstellung von 4"-epi-erythromycin a und derivaten hiervon als brauchbare antibakterielle mittel | |
| DE2831579C3 (de) | Tetrahydropyranylether von Daunomycin und Adriamycin, Verfahren zu ihrer Herstellung, sowie diese Verbindungen enthaltende pharmazeutische Zubereitungen | |
| CH636869A5 (en) | Process for the preparation of flavones | |
| EP0136831A2 (en) | Azahomoerythromycin B derivatives and intermediates thereof | |
| DE2366288C3 (de) | Verfahren zur Herstellung von 3' -Desoxykanamycin B und 3' -Desoxyneamin | |
| DE2804507C2 (de) | 4"-Desoxy-4"-amino-erythromycin-A und dessen Derivate sowie diese Verbindungen enthaltende antibakterielle Mittel | |
| DE2731306C3 (de) | 9-Desacetyl- und 9-Desacetyl-9-epi-daunorubicin, Verfahren zu deren Herstellung und deren Verwendung | |
| DE3641835A1 (de) | Zytostatisch wirksame anthracyclinderivate | |
| CH642973A5 (de) | Antitumoranthracycline mit verzweigtkettigen aminodeoxyzuckerresten. | |
| DE2756057A1 (de) | Verfahren zur herstellung von 3',4'-dideoxykanamycin b | |
| DE69418715T2 (de) | Erythromycinderivate | |
| DE3009910C2 (de) | 3',4'-Diepi-4'-O-methyl-daunorubicin und -doxorubicin, Verfahren zu deren Herstellung und diese Verbindungen enthaltende pharmazeutische Zubereitungen | |
| CH449006A (de) | Verfahren zur Herstellung von Fusidinsäure- und Dihydrofusidinsäurederivaten | |
| CH642975A5 (de) | 4''-deoxy-4''-glyoxamido- und -carbonylthioformamidoderivate von oleandomycin und dessen estern, verfahren zu ihrer herstellung und diese enthaltende arzneimittel. | |
| CA1250284A (en) | Antibacterial epimeric azahomoerythromycin a derivative and production thereof | |
| CH507934A (de) | Verfahren zur Herstellung eines neuen Glucosids | |
| DD215787A5 (de) | Verfahren zur herstellung neuer zwischenstufen fuer antibakterielle erythromycin-derivate | |
| DE2149187C3 (de) | Neue, enteral wirksame Periplorhamnosid-Derivate und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NPV | Change in the person, the name or the address of the representative (addendum to changes before extension act) | ||
| ENJ | Ceased due to non-payment of renewal fee |