LU83376A1 - Nouveaux derives d'imidazo-rifamycine a activite antibacterienne - Google Patents
Nouveaux derives d'imidazo-rifamycine a activite antibacterienne Download PDFInfo
- Publication number
- LU83376A1 LU83376A1 LU83376A LU83376A LU83376A1 LU 83376 A1 LU83376 A1 LU 83376A1 LU 83376 A LU83376 A LU 83376A LU 83376 A LU83376 A LU 83376A LU 83376 A1 LU83376 A1 LU 83376A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- carbon atoms
- group
- hydrogen atom
- singlet
- doublet
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 69
- 125000004432 carbon atom Chemical group C* 0.000 claims description 44
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 23
- HJYYPODYNSCCOU-ODRIEIDWSA-N rifamycin SV Chemical compound OC1=C(C(O)=C2C)C3=C(O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O HJYYPODYNSCCOU-ODRIEIDWSA-N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 9
- 229940109171 rifamycin sv Drugs 0.000 claims description 9
- HJYYPODYNSCCOU-ZDHWWVNNSA-N Rifamycin SV Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)cc(O)c4c3C2=O HJYYPODYNSCCOU-ZDHWWVNNSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000003960 organic solvent Substances 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- -1 amino- Chemical class 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- 229930189077 Rifamycin Natural products 0.000 claims description 2
- 239000003638 chemical reducing agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052740 iodine Inorganic materials 0.000 claims description 2
- 150000003222 pyridines Chemical class 0.000 claims description 2
- 229960003292 rifamycin Drugs 0.000 claims description 2
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 claims 2
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 241000124008 Mammalia Species 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 150000008282 halocarbons Chemical class 0.000 claims 1
- 239000007788 liquid Substances 0.000 claims 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 claims 1
- 238000000862 absorption spectrum Methods 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 24
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 15
- 238000000354 decomposition reaction Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000002904 solvent Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000001580 bacterial effect Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 8
- BTVYFIMKUHNOBZ-ZDHWWVNNSA-N Rifamycin S Natural products COC1C=COC2(C)Oc3c(C)c(O)c4C(=O)C(=CC(=O)c4c3C2=O)NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C BTVYFIMKUHNOBZ-ZDHWWVNNSA-N 0.000 description 8
- BTVYFIMKUHNOBZ-ODRIEIDWSA-N Rifamycin S Chemical compound O=C1C(C(O)=C2C)=C3C(=O)C=C1NC(=O)\C(C)=C/C=C/[C@H](C)[C@H](O)[C@@H](C)[C@@H](O)[C@@H](C)[C@H](OC(C)=O)[C@H](C)[C@@H](OC)\C=C\O[C@@]1(C)OC2=C3C1=O BTVYFIMKUHNOBZ-ODRIEIDWSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- 235000011152 sodium sulphate Nutrition 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000010828 elution Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000000968 intestinal effect Effects 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 230000008034 disappearance Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
- 230000008030 elimination Effects 0.000 description 2
- 238000003379 elimination reaction Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000001575 pathological effect Effects 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 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 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 210000002700 urine Anatomy 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- RGDQRXPEZUNWHX-UHFFFAOYSA-N 3-methylpyridin-2-amine Chemical compound CC1=CC=CN=C1N RGDQRXPEZUNWHX-UHFFFAOYSA-N 0.000 description 1
- LLWFWIZOFFLRKC-UHFFFAOYSA-N 3-phenylmethoxypyridine Chemical compound C=1C=CC=CC=1COC1=CC=CN=C1 LLWFWIZOFFLRKC-UHFFFAOYSA-N 0.000 description 1
- CMBSSVKZOPZBKW-UHFFFAOYSA-N 5-methylpyridin-2-amine Chemical compound CC1=CC=C(N)N=C1 CMBSSVKZOPZBKW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920001479 Hydroxyethyl methyl cellulose Polymers 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
- 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
- 241000699670 Mus sp. Species 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 229930193140 Neomycin Natural products 0.000 description 1
- 101001041669 Oryctolagus cuniculus Corticostatin 1 Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- XTPGUQSTSWYULT-ZDHWWVNNSA-N Rifamycin P Natural products COC1C=COC2(C)Oc3c(C)c(O)c4c(O)c(NC(=O)C(=C/C=C/C(C)C(O)C(C)C(O)C(C)C(OC(=O)C)C1C)C)c5scnc5c4c3C2=O XTPGUQSTSWYULT-ZDHWWVNNSA-N 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 229940126574 aminoglycoside antibiotic Drugs 0.000 description 1
- 239000002647 aminoglycoside antibiotic agent Substances 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 229960005070 ascorbic acid Drugs 0.000 description 1
- 235000010323 ascorbic acid Nutrition 0.000 description 1
- 239000011668 ascorbic acid Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000002510 pyrogen Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- XTPGUQSTSWYULT-TXXBDZDDSA-N rifamycin p Chemical compound OC1=C(C(O)=C2C)C3=C4N=CSC4=C1NC(=O)\C(C)=C\C=C\C(C)C(O)C(C)C(O)C(C)C(OC(C)=O)C(C)C(OC)\C=C/OC1(C)OC2=C3C1=O XTPGUQSTSWYULT-TXXBDZDDSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000002485 urinary effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/22—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains four or more hetero rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT03429/80A IT1154655B (it) | 1980-05-22 | 1980-05-22 | Derivati imidazo-rifamicinici metodi per la loro preparazione e loro uso come sostanza ad azione antibatterica |
| IT342980 | 1980-05-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU83376A1 true LU83376A1 (fr) | 1981-09-11 |
Family
ID=11107198
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU83376A LU83376A1 (fr) | 1980-05-22 | 1981-05-20 | Nouveaux derives d'imidazo-rifamycine a activite antibacterienne |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4341785A (member.php) |
| JP (1) | JPS5711987A (member.php) |
| AR (1) | AR226212A1 (member.php) |
| AT (1) | AT373599B (member.php) |
| AU (1) | AU537093B2 (member.php) |
| BE (1) | BE888895A (member.php) |
| CA (1) | CA1142518A (member.php) |
| CH (1) | CH648037A5 (member.php) |
| DE (1) | DE3120460A1 (member.php) |
| DK (1) | DK157876C (member.php) |
| EG (1) | EG14891A (member.php) |
| ES (1) | ES8203388A1 (member.php) |
| FI (1) | FI69467C (member.php) |
| FR (1) | FR2482967A1 (member.php) |
| GB (1) | GB2079270B (member.php) |
| GR (1) | GR75640B (member.php) |
| IE (1) | IE51204B1 (member.php) |
| IT (1) | IT1154655B (member.php) |
| LU (1) | LU83376A1 (member.php) |
| NL (1) | NL187022C (member.php) |
| NO (1) | NO155622C (member.php) |
| PH (2) | PH17207A (member.php) |
| PT (1) | PT73064B (member.php) |
| SE (1) | SE453089B (member.php) |
| ZA (1) | ZA813430B (member.php) |
Families Citing this family (77)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1199374B (it) * | 1984-05-15 | 1988-12-30 | Alfa Farmaceutici Spa | Processo per la preparazione di pirido-imidazo-rifamicine |
| IT1264494B1 (it) * | 1993-03-23 | 1996-09-24 | Alfa Wassermann Spa | Uso di rifaximin e di formulazioni che la contengono nel trattamento delle dispepsie gastriche originate da helicobacter |
| US7048906B2 (en) * | 1995-05-17 | 2006-05-23 | Cedars-Sinai Medical Center | Methods of diagnosing and treating small intestinal bacterial overgrowth (SIBO) and SIBO-related conditions |
| US6861053B1 (en) | 1999-08-11 | 2005-03-01 | Cedars-Sinai Medical Center | Methods of diagnosing or treating irritable bowel syndrome and other disorders caused by small intestinal bacterial overgrowth |
| US5981522A (en) * | 1995-09-01 | 1999-11-09 | Kaneka Corporation | Treatment of disease caused by infection of Helicobacter |
| KR100407851B1 (ko) * | 1997-02-28 | 2004-04-29 | 가네가후치 가가쿠고교 가부시키가이샤 | 헬리코박터의감염에기인하는질환치료제 |
| EP1453837A4 (en) * | 2001-11-21 | 2007-11-07 | Activbiotics Inc | TARGETED THERAPEUTIC AGENTS AND USES THEREOF |
| WO2003051299A2 (en) * | 2001-12-13 | 2003-06-26 | Activbiotics, Inc. | Sulfhydryl rifamycins and uses thereof |
| WO2004041240A1 (en) * | 2002-11-05 | 2004-05-21 | Piero Chiarelli | Controlled and continued delivery of rifaximin and/or other substances |
| US7820652B2 (en) * | 2003-09-24 | 2010-10-26 | Activbiotics Pharma, Llc | Regimen for the administration of rifamycin-class antibiotics |
| US7902206B2 (en) * | 2003-11-07 | 2011-03-08 | Alfa Wassermann, S.P.A. | Polymorphic forms α, β and γ of rifaximin |
| US20080262024A1 (en) * | 2003-11-07 | 2008-10-23 | Giuseppe Claudio Viscomi | Rifaximin compositions and method of use |
| US7923553B2 (en) * | 2003-11-07 | 2011-04-12 | Alfa Wassermann, S.P.A. | Processes for the production of polymorphic forms of rifaximin |
| US7906542B2 (en) * | 2004-11-04 | 2011-03-15 | Alfa Wassermann, S.P.A. | Pharmaceutical compositions comprising polymorphic forms α, β, and γ of rifaximin |
| ITMI20032144A1 (it) * | 2003-11-07 | 2005-05-08 | Alfa Wassermann Spa | Forme polimorfe di rifaximina, processi per ottenerle e |
| US7256187B2 (en) * | 2004-03-10 | 2007-08-14 | Cumbre Pharmaceuticals Inc. | Rifamycin C-11 oxime derivatives effective against drug-resistant microbes |
| US7265107B2 (en) * | 2004-03-10 | 2007-09-04 | Cumbre Pharmaceuticals Inc. | Rifamycin C-11 oxime cyclo derivatives effective against drug-resistant microbes |
| US7202246B2 (en) * | 2004-06-09 | 2007-04-10 | Cumbre Pharmaceuticals Inc. | Spiro-rifamycin derivatives targeting RNA polymerase |
| US8003118B2 (en) * | 2005-03-02 | 2011-08-23 | Kodsi Robert E | Use of rifaximin for the prevention of aspiration pneumonia and/or sepsis |
| US20060210492A1 (en) * | 2005-03-02 | 2006-09-21 | Kodsi Robert E | Use of rifaximin for treatment and prevention of periodontal conditions |
| US20060210483A1 (en) * | 2005-03-02 | 2006-09-21 | Kodsi Robert E | Non-systemic antibiotic formulations and related method of use and treatment of upper respiratory infections |
| PL1698630T3 (pl) | 2005-03-03 | 2014-12-31 | Alfasigma Spa | Nowe postacie polimorficzne rifaksyminy,sposoby ich wytwarzania i ich zastosowanie w preparatach leczniczych |
| ITBO20050123A1 (it) | 2005-03-07 | 2005-06-06 | Alfa Wassermann Spa | Formulazioni farmaceutiche gastroresistenti contenenti rifaximina |
| WO2007096703A2 (en) | 2005-08-11 | 2007-08-30 | Targanta Therapeutics Inc. | Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
| BRPI0708561A2 (pt) | 2006-03-09 | 2011-06-07 | Salix Pharmaceuticals Inc | preparação farmacêutica, e métodos de tratamento de um indivìduo que sofre de um distúrbio anal, e de avaliação da eficácia de um tratamento de distúrbio anal em um indivìduo, monitoramento do progresso de um indivìduo sendo tratado para um distúrbio anal, ou um método de seleção de um indivìduo para o tratamento de distúrbio anal |
| MX2009001342A (es) | 2006-08-02 | 2009-08-31 | Salix Pharmaceuticals Inc | Composiciones y metodos para el tratamiento de proctosigmoiditis por radiacion. |
| ITMI20061692A1 (it) | 2006-09-05 | 2008-03-06 | Alfa Wassermann Spa | Uso di polioli per ottenere forme polimorfe stabili di rifaximina |
| JP2010504314A (ja) * | 2006-09-22 | 2010-02-12 | シプラ・リミテッド | リファキシミン |
| US20080159987A1 (en) * | 2007-01-03 | 2008-07-03 | Leonard Weinstock | Use of Rifaximin for the Treatment of Restless Legs Syndrome |
| US20080161337A1 (en) * | 2007-01-03 | 2008-07-03 | Leonard Weinstock | Use of Rifaximin for the Treatment of Chronic Prostatitis |
| ITMI20071241A1 (it) * | 2007-06-20 | 2008-12-21 | Solmag S P A | Processo per la preparazione di rifaximina amorfa e rifaximina amorfa cosi' ottenuta |
| US8383151B2 (en) | 2007-07-06 | 2013-02-26 | Lupin Limited | Pharmaceutical compositions of rifaximin |
| ES2389358T5 (es) | 2007-07-06 | 2016-01-19 | Lupin Ltd. | Composiciones farmacéuticas de rifaximina |
| US7709634B2 (en) * | 2007-09-20 | 2010-05-04 | Apotex Pharmachem Inc. | Amorphous form of rifaximin and processes for its preparation |
| MX2010009389A (es) | 2008-02-25 | 2010-11-22 | Salix Pharmaceuticals Ltd | Formas de rifaximina y sus usos. |
| US8486956B2 (en) | 2008-02-25 | 2013-07-16 | Salix Pharmaceuticals, Ltd | Forms of rifaximin and uses thereof |
| NZ587098A (en) | 2008-02-26 | 2012-09-28 | Salix Pharmaceuticals Ltd | Use of a rifamycin class antibiotic for treating diarrhea-associated Irritable Bowel Syndrome and hepatic encephalopathy |
| US11779571B2 (en) | 2008-02-26 | 2023-10-10 | Salix Pharmaceuticals, Inc. | Methods for treating irritable bowel syndrome (IBS) |
| DK2294012T3 (da) | 2008-05-07 | 2014-10-06 | Salix Pharmaceuticals Ltd | Administration af et tarmrensemiddel og et antibiotika til behandlingen af tarmsygdom |
| US8524691B2 (en) | 2008-08-13 | 2013-09-03 | The Medicines Company | Phosphonated rifamycins and uses thereof for the prevention and treatment of bone and joint infections |
| BRPI0918997A2 (pt) | 2008-09-26 | 2015-12-01 | Aska Pharm Co Ltd | agente para evitar e/ou tratar um disturbio gastrointestinal funcional. |
| US12285414B2 (en) | 2008-10-02 | 2025-04-29 | Salix Pharmaceuticals, Inc. | Methods of treating hepatic encephalopathy |
| EP2350096B1 (en) | 2008-10-02 | 2019-12-11 | Salix Pharmaceuticals, Ltd. | Methods of treating hepatic encephalopathy |
| WO2010067072A1 (en) | 2008-12-10 | 2010-06-17 | Cipla Limited | Rifaximin complexes |
| IT1397617B1 (it) * | 2009-04-20 | 2013-01-18 | Alfa Wassermann Spa | Nuovi derivati della rifamicina |
| KR20120025578A (ko) | 2009-06-02 | 2012-03-15 | 샐릭스 파마슈티컬스 리미티드 | 간성 뇌병증의 치료방법 |
| RU2582940C2 (ru) | 2009-09-13 | 2016-04-27 | Саликс Фармасьютикалз, Лтд. | Способы лечения синдрома раздраженного кишечника (срк) |
| SG10201501054TA (en) | 2009-10-27 | 2015-04-29 | Lupin Ltd | Solid dispersion of rifaximin |
| CN102724960A (zh) | 2009-11-23 | 2012-10-10 | 希普拉有限公司 | 局部泡沫组合物 |
| US8952159B2 (en) | 2009-12-28 | 2015-02-10 | Silvio Massimo Lavagna | Method for the production of amorphous rifaximin |
| AU2011218129A1 (en) | 2010-02-18 | 2012-08-23 | Board Of Regents Of The University Of Texas System | Methods for treating infection |
| IT1398550B1 (it) | 2010-03-05 | 2013-03-01 | Alfa Wassermann Spa | Formulazioni comprendenti rifaximina utili per ottenere un effetto prolungato nel tempo |
| WO2011110930A2 (en) | 2010-03-10 | 2011-09-15 | Lupin Limited | Rifaximin ready-to-use suspension |
| CA2804635C (en) | 2010-07-12 | 2019-09-10 | Salix Pharmaceuticals, Ltd. | Formulations of rifaximin and uses thereof |
| WO2012035544A2 (en) | 2010-09-13 | 2012-03-22 | Sequent Scientific Ltd. | A novel polymorphic form of rifaximin and process for its preparation |
| MX350448B (es) | 2011-02-11 | 2017-09-07 | Salix Pharmaceuticals Ltd | Formas de rifaximina y usos de las mismas. |
| WO2012150561A1 (en) | 2011-05-02 | 2012-11-08 | Ranbaxy Laboratories Limited | Rifaximin dimethylformamide solvate |
| ITMI20110890A1 (it) | 2011-05-19 | 2012-11-20 | A M S A Anonima Materie Sint & Affini S P A | Polimorfo di rifaximina e processo per la sua preparazione |
| ITBO20110461A1 (it) | 2011-07-29 | 2013-01-30 | Alfa Wassermann Spa | Composizioni farmaceutiche comprendenti rifaximina, processi per la loro preparazione e loro uso nel trattamento di infezioni vaginali. |
| RU2496475C2 (ru) | 2011-10-26 | 2013-10-27 | Александр Васильевич Иващенко | Фармацевтическая композиция и набор для лечения бактериальных инфекций |
| US20130184302A1 (en) | 2011-11-02 | 2013-07-18 | Enoch Bortey | Methods for treating irritable bowel syndrome (ibs) and infections |
| CA2861104A1 (en) | 2012-01-25 | 2013-08-01 | Salix Pharmaceuticals, Ltd. | Rifaximin derivative and uses thereof |
| ITBO20120368A1 (it) | 2012-07-06 | 2014-01-07 | Alfa Wassermann Spa | Composizioni comprendenti rifaximina e amminoacidi, cristalli di rifaximina derivanti da tali composizioni e loro uso. |
| WO2014091432A1 (en) | 2012-12-12 | 2014-06-19 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of rifaximin |
| CA2897758A1 (en) | 2013-03-15 | 2014-09-18 | Alfa Wassermann S.P.A. | Rifaximin for use in the treating of vaginal infections |
| EP2971062A2 (en) | 2013-03-15 | 2016-01-20 | ALFA WASSERMANN S.p.A. | Method for diagnosing vaginal infections |
| CA2908525C (en) | 2013-04-12 | 2021-04-06 | Alfa Wassermann S.P.A. | Nsaid administration and related compositions, methods and systems |
| US9018225B1 (en) | 2013-07-26 | 2015-04-28 | Novel Laboratories | Rifaximin crystalline forms and methods of preparation thereof |
| ES2621557T3 (es) | 2014-03-31 | 2017-07-04 | Euticals S.P.A. | Mezcla polimórfica de rifaximina y su uso para la preparación de formulaciones sólidas |
| WO2015159275A2 (en) * | 2014-04-19 | 2015-10-22 | Granules India Limited | An improved process for the preparation of rifamycin derivatives |
| WO2015171493A1 (en) | 2014-05-04 | 2015-11-12 | Salix Pharmaceuticals, Inc. | Ibs microbiota and uses thereof |
| CA2940601C (en) | 2014-05-12 | 2021-08-24 | Alfa Wassermann S.P.A. | New solvated crystal form of rifaximin, production, compositions and uses thereof |
| EP2982764A1 (en) | 2014-08-05 | 2016-02-10 | ALFA WASSERMANN S.p.A. | Identification of vaginal bacteria |
| US9988398B2 (en) | 2016-06-07 | 2018-06-05 | Cadila Healthcare Limited | Crystalline form of rifaximin and process for its preparation |
| PT3518924T (pt) | 2016-09-30 | 2022-10-27 | Salix Pharmaceuticals Inc | Formas de dispersão sólidas de rifaximina |
| IT201700091912A1 (it) * | 2017-08-08 | 2019-02-08 | Biofer Spa | Nuove pirido-imidazo rifamicine |
| HUE054832T2 (hu) * | 2017-06-26 | 2021-10-28 | Biofer Spa | Pirido-imidazo rifamicinszármazékok baktériumellenes szerként |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE273377C (member.php) * | ||||
| AT273377B (de) * | 1967-03-01 | 1969-08-11 | Lepetit Spa | Verfahren zur Herstellung von neuen Rifamycinen |
| AT344898B (de) * | 1975-06-13 | 1978-08-10 | Archifar Ind Chim Trentino | Verfahren zur herstellung neuer rifamycin-verbindungen |
| DK345977A (da) * | 1976-09-30 | 1978-03-31 | Archifar Ind Chim Trentino | G rifamycinforbindelser og fremgangsmaade til deres fremstillin |
| CH629212A5 (it) * | 1976-10-18 | 1982-04-15 | Erba Farmitalia | Procedimento per la preparazione di composti di rifamicina. |
| CH633014A5 (en) * | 1978-06-09 | 1982-11-15 | Erba Farmitalia | Rifamycin compounds |
-
1980
- 1980-05-22 IT IT03429/80A patent/IT1154655B/it active Protection Beyond IP Right Term
-
1981
- 1981-05-11 NL NLAANVRAGE8102290,A patent/NL187022C/xx not_active IP Right Cessation
- 1981-05-11 US US06/262,123 patent/US4341785A/en not_active Expired - Lifetime
- 1981-05-18 AU AU70655/81A patent/AU537093B2/en not_active Expired
- 1981-05-19 AT AT0222781A patent/AT373599B/de not_active IP Right Cessation
- 1981-05-20 FR FR8110058A patent/FR2482967A1/fr active Granted
- 1981-05-20 PT PT73064A patent/PT73064B/pt unknown
- 1981-05-20 GR GR65010A patent/GR75640B/el unknown
- 1981-05-20 EG EG280/81A patent/EG14891A/xx active
- 1981-05-20 LU LU83376A patent/LU83376A1/fr unknown
- 1981-05-20 PH PH25656A patent/PH17207A/en unknown
- 1981-05-21 NO NO811731A patent/NO155622C/no unknown
- 1981-05-21 ZA ZA00813430A patent/ZA813430B/xx unknown
- 1981-05-21 CA CA000378015A patent/CA1142518A/en not_active Expired
- 1981-05-21 BE BE2/59169A patent/BE888895A/fr not_active IP Right Cessation
- 1981-05-21 FI FI811565A patent/FI69467C/fi not_active IP Right Cessation
- 1981-05-21 SE SE8103216A patent/SE453089B/sv not_active IP Right Cessation
- 1981-05-21 DK DK224781A patent/DK157876C/da active
- 1981-05-21 ES ES502906A patent/ES8203388A1/es not_active Expired
- 1981-05-21 IE IE1139/81A patent/IE51204B1/en not_active IP Right Cessation
- 1981-05-22 DE DE19813120460 patent/DE3120460A1/de active Granted
- 1981-05-22 JP JP7787781A patent/JPS5711987A/ja active Granted
- 1981-05-22 AR AR285424A patent/AR226212A1/es active
- 1981-05-22 CH CH3381/81A patent/CH648037A5/de not_active IP Right Cessation
- 1981-05-22 GB GB8115790A patent/GB2079270B/en not_active Expired
-
1982
- 1982-02-09 PH PH26842A patent/PH18704A/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| LU83376A1 (fr) | Nouveaux derives d'imidazo-rifamycine a activite antibacterienne | |
| EP1045856A1 (fr) | Nouveaux amides aromatiques, leur procede de preparation et leur application comme medicaments | |
| CH621555A5 (member.php) | ||
| EP0061380A1 (fr) | Dérivés d'imidazo (1,2-a) pyrimidines, leur préparation et leur application en thérapeutique | |
| FR2480286A1 (fr) | Nouveaux derives de theophyllinylmethyldioxolane, leurs procedes de preparation et leur application en therapeutique | |
| DE3880561T2 (de) | Actinoninderivate mit physiologischen Aktivitäten. | |
| FR2658195A1 (fr) | Nouveaux derives de la 20, 21-dinoreburnamenine, leur procede de preparation et les nouveaux intermediaires ainsi obtenus, leur application comme medicaments et les compositions les renfermant. | |
| CA1094547A (fr) | Procede de preparation de derives de l'acide 3- carbamoyloxymethyl 7-(amino thiazolyl acetamido) cephalosporanique | |
| EP0044238B1 (fr) | Dérivés de céphalosporines sulfoxydes, procédé de préparation et compositions pharmaceutiques en contenant | |
| DE3523231C2 (de) | 1,8-Diacyloxy-10-acylanthrone, Verfahren zu ihrer Herstellung und pharmazeutische und kosmetische Mittel | |
| FR2492821A1 (fr) | Derives de la pyrimidine, leur procede de preparation et les compositions pharmaceutiques les contenant | |
| EP0008965B1 (fr) | Nouveaux aminoglycosides dérivés de la désoxystreptamine et leurs sels, leur procédé de préparation, leur application à titre de médicaments et les compositions pharmaceutiques les renfermant | |
| CA1143740A (fr) | PROCEDE DE PREPARATION DE NOUVELLES .beta.- LACTONES DERIVEES DE L'ACIDE 2-HYDROXY CYCLOPENTANE CARBOXYLIQUE | |
| EP0002219B1 (de) | Arzneimittel mit schwefelhaltigen Estern und Verfahren zu ihrer Herstellung | |
| FR2504134A1 (fr) | Nouveaux derives du nitroimidazole, un procede pour leur preparation et compositions therapeutiques trichomonoacides en contenant | |
| WO1996004299A1 (fr) | Derives de streptogramine, leur preparation et les compositions pharmaceutiques qui les contiennent | |
| DE2654627C3 (de) | Oleandomycinderivate und deren nicht-toxische Säureanlagerungssalze, Verfahren zu deren Herstellung sowie diese Verbindungen enthaltende antibakterielle Arzneimittel | |
| FR2561105A1 (fr) | Sels d'erythromycine avec des derives de l'acide acetique. procede pour leur preparation et compositions pharmaceutiques en contenant | |
| DE3521722A1 (de) | Neue oxazino-verbindungen, verfahren zu ihrer herstellung und ihre verwendung | |
| FR2483928A1 (fr) | Derives de la n-trifluoracetyladriamycine, leur preparation et leurs utilisations therapeutiques | |
| FR2460304A1 (fr) | Hydrazones solubles dans l'eau de la formyl-3 rifamycine sv, utiles comme medicaments, leur procede de preparation et compositions therapeutiques les contenant | |
| DE2753768A1 (de) | Antiphologistisch wirkende arzneimittel | |
| BE881677A (fr) | Nouveaux derives d'acide penicillanique utile notamment comme antibiotiques et leurs procedes de preparation | |
| JPS6160837B2 (member.php) | ||
| BE851218A (fr) | Oleandomycines semi-synthetiques antibiotiques |