FI111264B - Uudet erytromysiinijohdannaiset, menetelmät niiden valmistamiseksi ja niiden käyttö lääkkeinä - Google Patents
Uudet erytromysiinijohdannaiset, menetelmät niiden valmistamiseksi ja niiden käyttö lääkkeinä Download PDFInfo
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- FI111264B FI111264B FI955913A FI955913A FI111264B FI 111264 B FI111264 B FI 111264B FI 955913 A FI955913 A FI 955913A FI 955913 A FI955913 A FI 955913A FI 111264 B FI111264 B FI 111264B
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- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 title claims description 56
- 238000002360 preparation method Methods 0.000 title claims description 29
- 239000003814 drug Substances 0.000 title claims description 12
- 238000000034 method Methods 0.000 title claims description 10
- 229940079593 drug Drugs 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 165
- -1 oxycarbonyl- (2- (3- (4-quinolinyl) propyl) hydrazono) Chemical class 0.000 claims description 50
- 229960003276 erythromycin Drugs 0.000 claims description 27
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 23
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 150000001299 aldehydes Chemical class 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical group 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 23
- 238000003756 stirring Methods 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 150000003254 radicals Chemical class 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000003480 eluent Substances 0.000 description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 8
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- 229940126062 Compound A Drugs 0.000 description 7
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 241000193998 Streptococcus pneumoniae Species 0.000 description 5
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 5
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 5
- 150000007857 hydrazones Chemical class 0.000 description 5
- 125000005638 hydrazono group Chemical group 0.000 description 5
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 5
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
- 241000894006 Bacteria Species 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 150000005840 aryl radicals Chemical class 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
- GTJNQHWEJNBLLS-UHFFFAOYSA-N n,n-diethylethanamine;methanol;2-propan-2-yloxypropane Chemical compound OC.CCN(CC)CC.CC(C)OC(C)C GTJNQHWEJNBLLS-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- MGCGJBXTNWUHQE-UHFFFAOYSA-N quinoline-4-carbaldehyde Chemical compound C1=CC=C2C(C=O)=CC=NC2=C1 MGCGJBXTNWUHQE-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 4
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- JJMTYUUFWCZEAA-UHFFFAOYSA-N 3-(1h-imidazol-2-yl)propanal Chemical compound O=CCCC1=NC=CN1 JJMTYUUFWCZEAA-UHFFFAOYSA-N 0.000 description 3
- KECFNYKLSNPOOB-UHFFFAOYSA-N 3-(3-phenyl-1,2,4-oxadiazol-5-yl)propanal Chemical compound O1C(CCC=O)=NC(C=2C=CC=CC=2)=N1 KECFNYKLSNPOOB-UHFFFAOYSA-N 0.000 description 3
- UXFKFJVEGHQOGU-UHFFFAOYSA-N 3-(4-phenylimidazol-1-yl)propanal Chemical compound O=CCCN1C=NC(C=2C=CC=CC=2)=C1 UXFKFJVEGHQOGU-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000193985 Streptococcus agalactiae Species 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 3
- DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 3
- QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 3
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- 239000000825 pharmaceutical preparation Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 3
- 125000000335 thiazolyl group Chemical group 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 3
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 2
- GGZQLTVZPOGLCC-UHFFFAOYSA-N 2-(2-bromoethyl)-1,3-dioxolane Chemical compound BrCCC1OCCO1 GGZQLTVZPOGLCC-UHFFFAOYSA-N 0.000 description 2
- GCADRZXDZQALMW-UHFFFAOYSA-N 3-(2-chlorophenyl)propanal Chemical compound ClC1=CC=CC=C1CCC=O GCADRZXDZQALMW-UHFFFAOYSA-N 0.000 description 2
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 2
- 241000194032 Enterococcus faecalis Species 0.000 description 2
- 241000194031 Enterococcus faecium Species 0.000 description 2
- 241000606790 Haemophilus Species 0.000 description 2
- 241000606768 Haemophilus influenzae Species 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 206010041925 Staphylococcal infections Diseases 0.000 description 2
- 241000191940 Staphylococcus Species 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 210000002615 epidermis Anatomy 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
- 125000001041 indolyl group Chemical group 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 235000019359 magnesium stearate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
- 239000002808 molecular sieve Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000000168 pyrrolyl group Chemical group 0.000 description 2
- ALQUTEKNDPODSS-UHFFFAOYSA-N quinoline-4-carbaldehyde-oxime Natural products C1=CC=C2C(C=NO)=CC=NC2=C1 ALQUTEKNDPODSS-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 210000003491 skin Anatomy 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- ITOFPJRDSCGOSA-KZLRUDJFSA-N (2s)-2-[[(4r)-4-[(3r,5r,8r,9s,10s,13r,14s,17r)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthren-17-yl]pentanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H](CC[C@]13C)[C@@H]2[C@@H]3CC[C@@H]1[C@H](C)CCC(=O)N[C@H](C(O)=O)CC1=CNC2=CC=CC=C12 ITOFPJRDSCGOSA-KZLRUDJFSA-N 0.000 description 1
- QYAPHLRPFNSDNH-MRFRVZCGSA-N (4s,4as,5as,6s,12ar)-7-chloro-4-(dimethylamino)-1,6,10,11,12a-pentahydroxy-6-methyl-3,12-dioxo-4,4a,5,5a-tetrahydrotetracene-2-carboxamide;hydrochloride Chemical compound Cl.C1=CC(Cl)=C2[C@](O)(C)[C@H]3C[C@H]4[C@H](N(C)C)C(=O)C(C(N)=O)=C(O)[C@@]4(O)C(=O)C3=C(O)C2=C1O QYAPHLRPFNSDNH-MRFRVZCGSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- LQFLWENCRMHCBB-UHFFFAOYSA-N 1-[2-(1,3-dioxolan-2-yl)ethyl]imidazole Chemical compound O1CCOC1CCN1C=CN=C1 LQFLWENCRMHCBB-UHFFFAOYSA-N 0.000 description 1
- VROMJSDIQMATBP-UHFFFAOYSA-N 2-(2-chlorophenyl)propanal Chemical compound O=CC(C)C1=CC=CC=C1Cl VROMJSDIQMATBP-UHFFFAOYSA-N 0.000 description 1
- AEJOSDWQCPXZCC-UHFFFAOYSA-N 2-(2-pyridin-3-yl-1,3-thiazol-4-yl)propanal Chemical compound O=CC(C)C1=CSC(C=2C=NC=CC=2)=N1 AEJOSDWQCPXZCC-UHFFFAOYSA-N 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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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
- 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)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR9404154 | 1994-04-08 | ||
| FR9404154A FR2718450B1 (fr) | 1994-04-08 | 1994-04-08 | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| FR9500441 | 1995-04-06 | ||
| PCT/FR1995/000441 WO1995027720A1 (fr) | 1994-04-08 | 1995-04-06 | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI955913A7 FI955913A7 (fi) | 1995-12-08 |
| FI955913A0 FI955913A0 (fi) | 1995-12-08 |
| FI111264B true FI111264B (fi) | 2003-06-30 |
Family
ID=9461886
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI955913A FI111264B (fi) | 1994-04-08 | 1995-12-08 | Uudet erytromysiinijohdannaiset, menetelmät niiden valmistamiseksi ja niiden käyttö lääkkeinä |
Country Status (49)
Families Citing this family (50)
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| FR2732023B1 (fr) * | 1995-03-22 | 1997-04-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2742757B1 (fr) * | 1995-12-22 | 1998-01-30 | Roussel Uclaf | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2745289B1 (fr) * | 1996-02-28 | 1998-05-29 | Roussel Uclaf | Nouveaux derives de l'acide 1(2h) quinoleine carboxylique, leur procede de preparation et leur application a la synthese de produits doues de proprietes antibiotiques |
| US5750510A (en) * | 1997-04-04 | 1998-05-12 | Abbott Laboratories | 3-descladinose-2,3-anhydroerythromycin derivatives |
| DE69723848T2 (de) * | 1996-05-07 | 2004-07-01 | Abbott Laboratories, Abbott Park | 3-descladinose-2,3-anhydroerythromycin-derivate |
| FR2748746B1 (fr) * | 1996-05-14 | 1998-08-14 | Hoechst Marion Roussel Inc | Nouveau procede d'isomerisation du radical methyle en 10 de derives de l'erythromycine |
| FR2751656B1 (fr) * | 1996-07-24 | 1998-10-16 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| UA51730C2 (uk) * | 1996-09-04 | 2002-12-16 | Ебботт Лабораторіз | 6-o-заміщені кетоліди з антибактеріальною активністю, спосіб їх одержання (варіанти), фармацевтична композиція та спосіб регулювання бактеріальної інфекції у ссавців |
| IL128681A0 (en) * | 1996-09-04 | 2000-01-31 | Abbott Lab | 6-O substituted ketolides having antibacterial activity |
| FR2757168B1 (fr) * | 1996-12-12 | 1999-06-11 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| FR2760017B1 (fr) * | 1997-02-27 | 1999-04-30 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erytromycine, leur procede de preparation et leur application comme medicaments |
| AU4472897A (en) * | 1997-03-10 | 1998-09-29 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a derivatives |
| WO1998042720A1 (fr) * | 1997-03-24 | 1998-10-01 | Taisho Pharmaceutical Co., Ltd. | Derives d'erythromycine a |
| AU6932098A (en) * | 1997-05-09 | 1998-12-08 | Pfizer Products Inc. | Erythromycin derivatives |
| US5922683A (en) * | 1997-05-29 | 1999-07-13 | Abbott Laboratories | Multicyclic erythromycin derivatives |
| BR9810021A (pt) * | 1997-06-11 | 2000-09-19 | Pfizer Prod Inc | Derivados 9-oxima-eritromicina |
| FR2771008B1 (fr) * | 1997-11-17 | 2000-04-28 | Hoechst Marion Roussel Inc | Utilisation des ketolides pour la preparation de compositions pharmaceutiques destinees a prevenir les complications thrombotiques arterielles liees a l'atherosclerose |
| AP1060A (en) * | 1998-01-02 | 2002-04-23 | Pfizer Prod Inc | Novel erythromycin derivatives. |
| HRP980189B1 (en) * | 1998-04-06 | 2004-04-30 | Pliva Pharm & Chem Works | Novel 15-membered lactams ketolides |
| ES2243066T3 (es) | 1998-09-22 | 2005-11-16 | Pfizer Products Inc. | Antibioticos de carbamato y carbazato cetolida. |
| FR2786188B1 (fr) * | 1998-11-24 | 2002-10-31 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur applicaion comme medicaments |
| TR200102129T2 (tr) | 1998-12-10 | 2002-01-21 | Pfizer Products Inc. | Karbamat ve karbazat ketolid antibiyotikleri. |
| EP1298138B1 (en) * | 1998-12-10 | 2006-11-02 | Pfizer Products Inc. | Carbamate and Carbazate Ketolide Antibiotics |
| EP1749832A3 (en) * | 1998-12-10 | 2008-03-26 | Pfizer Products Incorporated | Carbamate and carbazate ketolide antibiotics |
| FR2789392B1 (fr) | 1999-02-04 | 2001-10-05 | Hoechst Marion Roussel Inc | Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US6054435A (en) * | 1999-03-19 | 2000-04-25 | Abbott Laboratories | 6-O-substituted macrolides having antibacterial activity |
| US6590083B1 (en) | 1999-04-16 | 2003-07-08 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| WO2000063224A2 (en) * | 1999-04-16 | 2000-10-26 | Kosan Biosciences, Inc. | Macrolide antiinfective agents |
| WO2000062783A2 (en) | 1999-04-16 | 2000-10-26 | Ortho-Mcneil Pharmaceutical, Inc. | Ketolide antibacterials |
| EP1180110A1 (en) * | 1999-05-24 | 2002-02-20 | Pfizer Products Inc. | 13-methyl-erythromycin derivatives |
| CA2451391A1 (en) * | 2001-07-03 | 2003-01-16 | Chiron Corporation | C12 modified erythromycin macrolides and ketolides having antibacterial activity |
| MXPA04012978A (es) | 2002-07-01 | 2005-09-12 | Arkion Life Sciences Llc D B A | Proceso y material para la produccion de glucosamina y n-acetilglucosamina. |
| EP2772254A3 (en) | 2003-03-10 | 2015-03-11 | Optimer Pharmaceuticals, Inc. | Novel Antibacterial Agents |
| US7332476B2 (en) * | 2003-04-25 | 2008-02-19 | Novartis Ag | Pyridyl substituted ketolide antibiotics |
| US7163924B2 (en) * | 2003-04-25 | 2007-01-16 | Chiron Corporation | Ketolide derivatives |
| CA2703475A1 (en) * | 2007-10-25 | 2009-04-30 | Cempra Pharmaceuticals, Inc. | Process for the preparation of macrolide antibacterial agents |
| AU2009308182B2 (en) | 2008-10-24 | 2016-05-19 | Cempra Pharmaceuticals, Inc. | Biodefenses using triazole-containing macrolides |
| US9937194B1 (en) | 2009-06-12 | 2018-04-10 | Cempra Pharmaceuticals, Inc. | Compounds and methods for treating inflammatory diseases |
| WO2011032052A1 (en) | 2009-09-10 | 2011-03-17 | Cempra Pharmaceuticals, Inc. | Methods for treating malaria, tuberculosis and mac diseases |
| WO2011119604A1 (en) | 2010-03-22 | 2011-09-29 | Cempra Pharmaceuticals, Inc. | Crystalline forms of a macrolide, and uses therefor |
| DK2571506T3 (en) | 2010-05-20 | 2017-08-28 | Cempra Pharmaceuticals Inc | PROCEDURES FOR THE MANUFACTURE OF MACROLIDES AND KETOLIDES AND INTERMEDIATES |
| KR20130120458A (ko) | 2010-09-10 | 2013-11-04 | 셈프라 파마슈티컬스, 인크. | 질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드 |
| US10188674B2 (en) | 2012-03-27 | 2019-01-29 | Cempra Pharmaceuticals, Inc. | Parenteral formulations for administering macrolide antibiotics |
| AU2014239959A1 (en) | 2013-03-14 | 2015-10-01 | Cempra Pharmaceuticals, Inc. | Methods for treating respiratory diseases and formulations therefor |
| KR20160020403A (ko) | 2013-03-15 | 2016-02-23 | 셈프라 파마슈티컬스, 인크. | 매크로라이드 항세균제들을 제조하기 위한 수렴 프로세스들 |
| WO2014165792A2 (en) | 2013-04-04 | 2014-10-09 | President And Fellows Of Harvard College | Macrolides and methods of their preparation and use |
| HK1242920A1 (zh) | 2014-10-08 | 2018-07-06 | 哈佛大学的校长及成员们 | 14-元酮内酯及其制备和使用方法 |
| CN107530365A (zh) | 2015-03-25 | 2018-01-02 | 哈佛大学的校长及成员们 | 具有修饰的脱氧糖胺糖的大环内酯及其用途 |
| MD1222Z (ro) * | 2017-05-31 | 2018-08-31 | ИНСТИТУТ ЭЛЕКТРОННОЙ ИНЖЕНЕРИИ И НАНОТЕХНОЛОГИЙ "D. Ghitu" АНМ | Procedeu de tratare a materialului săditor al florilor înainte de plantare |
| JP7199722B2 (ja) | 2019-12-25 | 2023-01-06 | 旭精工株式会社 | 硬貨搬送振分機構及びそれを備えた硬貨識別搬送装置 |
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| US3868414A (en) * | 1973-01-22 | 1975-02-25 | Merck & Co Inc | Tetrahydrofluorene carboxylic acids and related compounds |
| AT342770B (de) * | 1975-04-07 | 1978-04-25 | Thomae Gmbh Dr K | Verfahren zur herstellung neuer erythromycinderivate |
| DE2842759A1 (de) * | 1978-09-30 | 1980-04-10 | Merck Patent Gmbh | Basische aether, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
| IL114589A (en) * | 1990-11-21 | 1999-12-22 | Roussel Uclaf | Intermediates for the preparation of erythromycin derivatives |
| FR2692579B1 (fr) * | 1992-06-19 | 1995-06-02 | Roussel Uclaf | Nouveaux dérivés de la picromycine, leur procédé de préparation et leur application comme médicaments. |
| FR2697524B1 (fr) * | 1992-11-05 | 1994-12-23 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| US5527780A (en) * | 1992-11-05 | 1996-06-18 | Roussel Uclaf | Erythromycin derivatives |
| 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 |
| FR2702480B1 (fr) * | 1993-03-09 | 1995-04-28 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
-
1994
- 1994-04-08 FR FR9404154A patent/FR2718450B1/fr not_active Expired - Fee Related
-
1995
- 1995-01-05 LV LVP-95-363A patent/LV11182B/lv unknown
- 1995-03-10 IL IL11295495A patent/IL112954A/xx not_active IP Right Cessation
- 1995-03-13 ZA ZA952059A patent/ZA952059B/xx unknown
- 1995-03-17 AP APAP/P/1995/000743A patent/AP587A/en active
- 1995-03-19 JO JO19951850A patent/JO1850B1/en active
- 1995-03-31 US US08/414,503 patent/US5656607A/en not_active Expired - Lifetime
- 1995-04-02 DZ DZ950037A patent/DZ1869A1/fr active
- 1995-04-03 PE PE1995265509A patent/PE2896A1/es not_active IP Right Cessation
- 1995-04-03 GB GB9506856A patent/GB2288174A/en not_active Withdrawn
- 1995-04-05 YU YU21695A patent/YU49221B/sh unknown
- 1995-04-05 JP JP7103170A patent/JP3000023B2/ja not_active Expired - Lifetime
- 1995-04-05 CO CO95013829A patent/CO4370097A1/es unknown
- 1995-04-05 MA MA23828A patent/MA23501A1/fr unknown
- 1995-04-06 AT AT95400763T patent/ATE234853T1/de active
- 1995-04-06 HU HU9503505A patent/HU215396B/hu unknown
- 1995-04-06 ES ES95400763T patent/ES2189820T3/es not_active Expired - Lifetime
- 1995-04-06 DE DE69529934T patent/DE69529934T2/de not_active Expired - Lifetime
- 1995-04-06 EE EE9500080A patent/EE04498B1/xx unknown
- 1995-04-06 DK DK95400763T patent/DK0676409T3/da active
- 1995-04-06 CA CA002164638A patent/CA2164638C/fr not_active Expired - Lifetime
- 1995-04-06 EP EP95400763A patent/EP0676409B1/fr not_active Expired - Lifetime
- 1995-04-06 PT PT95400763T patent/PT676409E/pt unknown
- 1995-04-06 UA UA95125173A patent/UA44705C2/uk unknown
- 1995-04-06 CZ CZ19953223A patent/CZ296005B6/cs not_active IP Right Cessation
- 1995-04-06 SK SK1546-95A patent/SK284079B6/sk not_active IP Right Cessation
- 1995-04-06 SI SI9530633T patent/SI0676409T1/xx unknown
- 1995-04-06 BR BR9506147A patent/BR9506147A/pt not_active IP Right Cessation
- 1995-04-06 NZ NZ284498A patent/NZ284498A/en not_active IP Right Cessation
- 1995-04-06 MD MD95-0431A patent/MD663G2/ro not_active IP Right Cessation
- 1995-04-06 RU RU96101139A patent/RU2141965C1/ru active
- 1995-04-06 WO PCT/FR1995/000441 patent/WO1995027720A1/fr not_active Ceased
- 1995-04-06 PL PL95311871A patent/PL180837B1/pl unknown
- 1995-04-06 RO RO95-02126A patent/RO115634B1/ro unknown
- 1995-04-06 TN TNTNSN95026A patent/TNSN95026A1/fr unknown
- 1995-04-06 KR KR1019950705537A patent/KR100317148B1/ko not_active Expired - Lifetime
- 1995-04-06 CN CN95190283A patent/CN1059445C/zh not_active Expired - Lifetime
- 1995-04-06 AU AU23107/95A patent/AU684939B2/en not_active Expired
- 1995-04-07 HR HR950217A patent/HRP950217B1/xx not_active IP Right Cessation
- 1995-04-07 MY MYPI95000907A patent/MY114672A/en unknown
- 1995-04-07 SV SV1995000018A patent/SV1995000018A/es not_active Application Discontinuation
- 1995-04-08 GE GEAP19952968A patent/GEP19991836B/en unknown
- 1995-06-05 TW TW084105604A patent/TW316908B/zh not_active IP Right Cessation
- 1995-11-17 IS IS4309A patent/IS1865B/is unknown
- 1995-11-20 BG BG100150A patent/BG61916B1/bg unknown
- 1995-12-06 NO NO954942A patent/NO308361B1/no not_active IP Right Cessation
- 1995-12-08 FI FI955913A patent/FI111264B/fi not_active IP Right Cessation
- 1995-12-08 OA OA60752A patent/OA10200A/fr unknown
-
1997
- 1997-02-25 US US08/805,439 patent/US5760233A/en not_active Expired - Lifetime
- 1997-03-29 SA SA97170757A patent/SA97170757A/ar unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| GB | Transfer or assigment of application |
Owner name: HOECHST MARION ROUSSEL |
|
| MA | Patent expired |