AP587A - New erythromycin derivatives, their preparation process and their use as medicaments. - Google Patents

New erythromycin derivatives, their preparation process and their use as medicaments. Download PDF

Info

Publication number: AP587A
Authority: AP; ARIPO
Prior art keywords: formula; compounds; methyl; radical; dideoxy
Prior art date: 1994-04-08

Application number

APAP/P/1995/000743A

Other languages

English (en)

Other versions

AP9500743A0 (en

Inventor

Constantin Agouridas

Yannick Benedetti

Jean-Francis Chantot (Deceased)

Alexis Denis

Martret Odile Le

Original Assignee

Aventis Pharma Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-04-08

Filing date

1995-03-17

Publication date

1997-04-29

1995-03-17 Application filed by Aventis Pharma Sa filed Critical Aventis Pharma Sa

1995-07-31 Publication of AP9500743A0 publication Critical patent/AP9500743A0/xx

1997-04-29 Application granted granted Critical

1997-04-29 Publication of AP587A publication Critical patent/AP587A/en

Links

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 47
238000002360 preparation method Methods 0.000 title claims description 29
239000003814 drug Substances 0.000 title claims description 13
150000001875 compounds Chemical class 0.000 claims abstract description 69
-1 oxycarbonyl (2-(3-(4-quinolinyl) 2-propyl) hydrazono) Chemical class 0.000 claims description 41
239000000203 mixture Substances 0.000 claims description 32
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
229960003276 erythromycin Drugs 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 14
125000004432 carbon atom Chemical group C* 0.000 claims description 13
125000005638 hydrazono group Chemical group 0.000 claims description 13
150000003839 salts Chemical class 0.000 claims description 13
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
229910052739 hydrogen Inorganic materials 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 8
125000005842 heteroatom Chemical group 0.000 claims description 8
150000007513 acids Chemical class 0.000 claims description 7
238000000034 method Methods 0.000 claims description 7
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
239000004215 Carbon black (E152) Substances 0.000 claims description 6
229930195733 hydrocarbon Natural products 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
229920006395 saturated elastomer Polymers 0.000 claims description 6
125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 5
125000003107 substituted aryl group Chemical group 0.000 claims description 5
239000003638 chemical reducing agent Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
239000012374 esterification 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
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
239000005864 Sulphur Substances 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
239000001301 oxygen Substances 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
229910017852 NH2NH2 Inorganic materials 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
125000000623 heterocyclic group 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
125000001072 heteroaryl group Chemical group 0.000 claims 1
239000004615 ingredient Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
239000000047 product Substances 0.000 description 113
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 66
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 54
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
239000000377 silicon dioxide Substances 0.000 description 33
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 30
239000000243 solution Substances 0.000 description 30
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 23
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
238000013019 agitation Methods 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 16
150000003254 radicals Chemical class 0.000 description 16
238000001704 evaporation Methods 0.000 description 14
238000000605 extraction Methods 0.000 description 14
238000001914 filtration Methods 0.000 description 12
238000005406 washing Methods 0.000 description 12
238000004458 analytical method Methods 0.000 description 11
238000004587 chromatography analysis Methods 0.000 description 11
238000001035 drying Methods 0.000 description 11
239000002904 solvent Substances 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 8
WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 7
239000000908 ammonium hydroxide Substances 0.000 description 7
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 7
239000012429 reaction media Substances 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
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
150000001299 aldehydes Chemical class 0.000 description 6
WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
230000008020 evaporation Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 5
241000193998 Streptococcus pneumoniae Species 0.000 description 5
230000001580 bacterial effect Effects 0.000 description 5
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 5
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 5
229940031000 streptococcus pneumoniae Drugs 0.000 description 5
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 4
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 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
125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 description 4
125000003118 aryl group Chemical group 0.000 description 4
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 4
229960001760 dimethyl sulfoxide Drugs 0.000 description 4
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 4
239000000284 extract Substances 0.000 description 4
238000010438 heat treatment Methods 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
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
238000010992 reflux Methods 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
239000000725 suspension Substances 0.000 description 4
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
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
241000193985 Streptococcus agalactiae Species 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
125000000217 alkyl group Chemical group 0.000 description 3
150000005840 aryl radicals Chemical class 0.000 description 3
239000012298 atmosphere Substances 0.000 description 3
244000052616 bacterial pathogen Species 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
QVDYYQXUNAQSNI-UHFFFAOYSA-N ethyl acetate;pentane Chemical compound CCCCC.CCOC(C)=O QVDYYQXUNAQSNI-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 3
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 3
229910052763 palladium Inorganic materials 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 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
HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-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
FYUUJKZXEUGJFF-UHFFFAOYSA-N 3-(2-phenyl-1,3-thiazol-5-yl)propanal Chemical compound S1C(CCC=O)=CN=C1C1=CC=CC=C1 FYUUJKZXEUGJFF-UHFFFAOYSA-N 0.000 description 2
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
206010002383 Angina Pectoris Diseases 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
229910020889 NaBH3 Inorganic materials 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
QQONPFPTGQHPMA-UHFFFAOYSA-N Propene Chemical compound CC=C QQONPFPTGQHPMA-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
241000191963 Staphylococcus epidermidis Species 0.000 description 2
229920002472 Starch Polymers 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
125000000304 alkynyl group Chemical group 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 2
YDVNLQGCLLPHAH-UHFFFAOYSA-N dichloromethane;hydrate Chemical compound O.ClCCl YDVNLQGCLLPHAH-UHFFFAOYSA-N 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 2
UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 2
229940047650 haemophilus influenzae Drugs 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
125000002883 imidazolyl group Chemical group 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
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
235000011181 potassium carbonates Nutrition 0.000 description 2
125000004076 pyridyl group Chemical group 0.000 description 2
125000000714 pyrimidinyl 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
URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000008107 starch Substances 0.000 description 2
235000019698 starch Nutrition 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
125000000335 thiazolyl group Chemical group 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
125000004505 1,2,4-oxadiazol-5-yl group Chemical group O1N=CN=C1* 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
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-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
WEBRDDDJKLAXTO-UHFFFAOYSA-N 2-ethyl-1,3-dioxolane Chemical compound CCC1OCCO1 WEBRDDDJKLAXTO-UHFFFAOYSA-N 0.000 description 1
KKALNCQCDXQTCG-UHFFFAOYSA-N 2-phenyl-1,3-thiazole-5-carbaldehyde Chemical compound S1C(C=O)=CN=C1C1=CC=CC=C1 KKALNCQCDXQTCG-UHFFFAOYSA-N 0.000 description 1
LCALUFNLWHYTKX-UHFFFAOYSA-N 2-phenyl-1,3-thiazole-5-carboxylic acid Chemical compound S1C(C(=O)O)=CN=C1C1=CC=CC=C1 LCALUFNLWHYTKX-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
IRBFZSQRGLMBAP-UHFFFAOYSA-N 2-quinolin-4-ylprop-2-enal Chemical compound C1=CC=C2C(C(C=O)=C)=CC=NC2=C1 IRBFZSQRGLMBAP-UHFFFAOYSA-N 0.000 description 1
ACVSHQGHCWUJFU-UHFFFAOYSA-N 2h-imidazole Chemical compound C1N=CC=N1 ACVSHQGHCWUJFU-UHFFFAOYSA-N 0.000 description 1
CGQLWWXAVSIXPY-UHFFFAOYSA-N 3-(1,3-thiazol-4-yl)propanal Chemical compound O=CCCC1=CSC=N1 CGQLWWXAVSIXPY-UHFFFAOYSA-N 0.000 description 1
RROVHEOLZYPASG-UHFFFAOYSA-N 3-(2-chlorophenyl)propan-1-ol Chemical compound OCCCC1=CC=CC=C1Cl RROVHEOLZYPASG-UHFFFAOYSA-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

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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)

APAP/P/1995/000743A 1994-04-08 1995-03-17 New erythromycin derivatives, their preparation process and their use as medicaments. AP587A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR9404154A FR2718450B1 (fr)	1994-04-08	1994-04-08	Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.

Publications (2)

Publication Number	Publication Date
AP9500743A0 AP9500743A0 (en)	1995-07-31
AP587A true AP587A (en)	1997-04-29

Family

ID=9461886

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
APAP/P/1995/000743A AP587A (en)	1994-04-08	1995-03-17	New erythromycin derivatives, their preparation process and their use as medicaments.

Country Status (49)

Country	Link
US (2)	US5656607A (cs)
EP (1)	EP0676409B1 (cs)
JP (1)	JP3000023B2 (cs)
KR (1)	KR100317148B1 (cs)
CN (1)	CN1059445C (cs)
AP (1)	AP587A (cs)
AT (1)	ATE234853T1 (cs)
AU (1)	AU684939B2 (cs)
BG (1)	BG61916B1 (cs)
BR (1)	BR9506147A (cs)
CA (1)	CA2164638C (cs)
CO (1)	CO4370097A1 (cs)
CZ (1)	CZ296005B6 (cs)
DE (1)	DE69529934T2 (cs)
DK (1)	DK0676409T3 (cs)
DZ (1)	DZ1869A1 (cs)
EE (1)	EE04498B1 (cs)
ES (1)	ES2189820T3 (cs)
FI (1)	FI111264B (cs)
FR (1)	FR2718450B1 (cs)
GB (1)	GB2288174A (cs)
GE (1)	GEP19991836B (cs)
HR (1)	HRP950217B1 (cs)
HU (1)	HU215396B (cs)
IL (1)	IL112954A (cs)
IS (1)	IS1865B (cs)
JO (1)	JO1850B1 (cs)
LV (1)	LV11182B (cs)
MA (1)	MA23501A1 (cs)
MD (1)	MD663G2 (cs)
MY (1)	MY114672A (cs)
NO (1)	NO308361B1 (cs)
NZ (1)	NZ284498A (cs)
OA (1)	OA10200A (cs)
PE (1)	PE2896A1 (cs)
PL (1)	PL180837B1 (cs)
PT (1)	PT676409E (cs)
RO (1)	RO115634B1 (cs)
RU (1)	RU2141965C1 (cs)
SA (1)	SA97170757A (cs)
SI (1)	SI0676409T1 (cs)
SK (1)	SK284079B6 (cs)
SV (1)	SV1995000018A (cs)
TN (1)	TNSN95026A1 (cs)
TW (1)	TW316908B (cs)
UA (1)	UA44705C2 (cs)
WO (1)	WO1995027720A1 (cs)
YU (1)	YU49221B (cs)
ZA (1)	ZA952059B (cs)

Families Citing this family (50)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
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- 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 GB GB9506856A patent/GB2288174A/en not_active Withdrawn
- 1995-04-03 PE PE1995265509A patent/PE2896A1/es not_active IP Right Cessation
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- 1995-04-05 JP JP7103170A patent/JP3000023B2/ja not_active Expired - Lifetime
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- 1995-04-06 UA UA95125173A patent/UA44705C2/uk unknown
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- 1995-04-06 MD MD95-0431A patent/MD663G2/ro not_active IP Right Cessation
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Also Published As

Publication number	Publication date
YU49221B (sh)	2004-11-25
BG100150A (bg)	1996-06-28
HU9503505D0 (en)	1996-02-28
CN1059445C (zh)	2000-12-13
CA2164638C (fr)	2003-12-30
EP0676409B1 (fr)	2003-03-19
JO1850B1 (en)	1995-12-27
CZ322395A3 (en)	1996-08-14
FI955913A0 (fi)	1995-12-08
MA23501A1 (fr)	1995-12-31
EE04498B1 (et)	2005-06-15
LV11182A (lv)	1996-04-20
NZ284498A (en)	1997-07-27
ZA952059B (en)	1996-03-13
ATE234853T1 (de)	2003-04-15
HUT73772A (en)	1996-09-30
AU2310795A (en)	1995-10-30
SA97170757A (ar)	2005-12-03
FI955913A7 (fi)	1995-12-08
JPH07278177A (ja)	1995-10-24
US5656607A (en)	1997-08-12
FR2718450A1 (fr)	1995-10-13
BG61916B1 (bg)	1998-09-30
YU21695A (sh)	1997-12-05
IL112954A0 (en)	1995-06-29
DE69529934T2 (de)	2003-09-04
UA44705C2 (uk)	2002-03-15
DE69529934D1 (de)	2003-04-24
BR9506147A (pt)	1996-04-16
NO954942L (no)	1996-02-07
CZ296005B6 (cs)	2005-12-14
PE2896A1 (es)	1996-02-12
PL180837B1 (pl)	2001-04-30
PL311871A1 (en)	1996-03-18
TW316908B (cs)	1997-10-01
AP9500743A0 (en)	1995-07-31
RO115634B1 (ro)	2000-04-28
FR2718450B1 (fr)	1997-01-10
HRP950217B1 (en)	2004-06-30
AU684939B2 (en)	1998-01-08
NO954942D0 (no)	1995-12-06
IS1865B (is)	2003-05-02
KR100317148B1 (ko)	2002-06-22
IS4309A (is)	1995-11-17
JP3000023B2 (ja)	2000-01-17
MD663F1 (ro)	1997-01-31
FI111264B (fi)	2003-06-30
GB9506856D0 (en)	1995-05-24
OA10200A (fr)	1996-12-18
CA2164638A1 (fr)	1995-10-19
RU2141965C1 (ru)	1999-11-27
HRP950217A2 (en)	1997-08-31
MD663G2 (ro)	1997-07-31
US5760233A (en)	1998-06-02
NO308361B1 (no)	2000-09-04
WO1995027720A1 (fr)	1995-10-19
HU215396B (hu)	1998-12-28
LV11182B (en)	1997-04-20
SK154695A3 (en)	1996-10-02
TNSN95026A1 (fr)	1996-02-06
SV1995000018A (es)	1997-10-24
GEP19991836B (en)	1999-11-05
EE9500080A (et)	1996-12-16
DZ1869A1 (fr)	2002-02-17
CN1126997A (zh)	1996-07-17
IL112954A (en)	2000-07-16
SK284079B6 (sk)	2004-09-08
SI0676409T1 (en)	2003-06-30
EP0676409A1 (fr)	1995-10-11
DK0676409T3 (da)	2003-06-23
MY114672A (en)	2002-12-31
CO4370097A1 (es)	1996-10-07
GB2288174A (en)	1995-10-11
PT676409E (pt)	2003-08-29
ES2189820T3 (es)	2003-07-16

Publication	Publication Date	Title
US5656607A (en)	1997-08-12	Erythromycin derivatives
US6147197A (en)	2000-11-14	6-O-substituted erythromycin ketolides having antibacterial activity
US5866549A (en)	1999-02-02	6-O-substituted ketolides having antibacterial activity
AU716204B2 (en)	2000-02-24	Novel erythromycin derivatives, method for preparing same, and use thereof as drugs
US5786339A (en)	1998-07-28	Erythromycins
US5543400A (en)	1996-08-06	Erythromycin compounds
US6313101B1 (en)	2001-11-06	Derivatives of erythromycin, their preparation process and their use as medicaments
HUP0201067A2 (en)	2002-08-28	6-o-substituted macrolides having antibacterial activity, pharmaceutical compositions containing them, their use and process for preparation of the compounds
US6034069A (en)	2000-03-07	3-'N-modified 6-O-substituted erythromycin ketolide derivatives having antibacterial activity
US6433151B1 (en)	2002-08-13	Erythromycin derivatives, a process for their preparation and their use as medicaments
FR2732023A1 (fr)	1996-09-27	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
US6162793A (en)	2000-12-19	Erythromycin derivatives, method for preparing same and use thereof as drugs
AP997A (en)	2001-08-09	Novel erythromycin derivatives, method for preparing them and their use as medicine.
FR2702480A1 (fr)	1994-09-16	Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.
US5747466A (en)	1998-05-05	3-deoxy-3-descladinose derivatives of erythromycins A and B
USRE38520E1 (en)	2004-05-18	Erythromycin derivatives, method for preparing same, and use thereof as drugs
HK1021537B (en)	2005-12-23	6-o-substituted ketolides having antibacterial activity
MXPA99005226A (en)	2000-01-01	Novel erythromycin derivatives, method for preparing them and their use as medicine