ES2707787T3 - Análogos antibacterianos de aminoglucósido 4,5-sustituidos que tienen sustituyentes múltiples - Google Patents

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Publication number

ES2707787T3

ES2707787T3 ES06844751T ES06844751T ES2707787T3 ES 2707787 T3 ES2707787 T3 ES 2707787T3 ES 06844751 T ES06844751 T ES 06844751T ES 06844751 T ES06844751 T ES 06844751T ES 2707787 T3 ES2707787 T3 ES 2707787T3

Authority

ES

Spain

Prior art keywords

substituted

compound

alkyl

alkynyl

alkenyl

Prior art date

2005-12-02

Legal status (The legal status 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 status listed.)

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• 229940126575 aminoglycoside Drugs 0.000 title description 22
• 230000000844 anti-bacterial effect Effects 0.000 title description 9
• 150000001875 compounds Chemical class 0.000 claims abstract description 391
• 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 75
• -1 -NJ1J2 Chemical group 0.000 claims abstract description 66
• 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims abstract description 57
• 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims abstract description 55
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 41
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 29
• 125000003118 aryl group Chemical group 0.000 claims abstract description 26
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 25
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 23
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 22
• 125000006239 protecting group Chemical group 0.000 claims abstract description 21
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 21
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 19
• 229940002612 prodrug Drugs 0.000 claims abstract description 18
• 239000000651 prodrug Substances 0.000 claims abstract description 18
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 16
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
• 150000002367 halogens Chemical class 0.000 claims abstract description 16
• 125000002950 monocyclic group Chemical group 0.000 claims abstract description 15
• 125000003367 polycyclic group Chemical group 0.000 claims abstract description 15
• 150000003839 salts Chemical class 0.000 claims abstract description 15
• 125000003277 amino group Chemical class 0.000 claims abstract description 12
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 7
• KWEDUNSJJZVRKR-UHFFFAOYSA-N carbononitridic azide Chemical compound [N-]=[N+]=NC#N KWEDUNSJJZVRKR-UHFFFAOYSA-N 0.000 claims abstract description 6
• 150000002148 esters Chemical class 0.000 claims abstract description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
• 150000001540 azides Chemical group 0.000 claims abstract description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 4
• 150000001735 carboxylic acids Chemical class 0.000 claims abstract 2
• 238000000034 method Methods 0.000 claims description 174
• 125000000217 alkyl group Chemical group 0.000 claims description 35
• 125000001424 substituent group Chemical group 0.000 claims description 30
• 125000000304 alkynyl group Chemical group 0.000 claims description 17
• 229960004927 neomycin Drugs 0.000 claims description 15
• 229930193140 Neomycin Natural products 0.000 claims description 14
• 229910052799 carbon Inorganic materials 0.000 claims description 8
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 6
• 208000035143 Bacterial infection Diseases 0.000 claims description 5
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
• 150000001298 alcohols Chemical class 0.000 claims description 3
• UBPIRRORRFGPNE-UHFFFAOYSA-N benzoic acid;formic acid Chemical class OC=O.OC(=O)C1=CC=CC=C1 UBPIRRORRFGPNE-UHFFFAOYSA-N 0.000 claims description 3
• 150000001558 benzoic acid derivatives Chemical class 0.000 abstract description 2
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 258
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 163
• 238000005481 NMR spectroscopy Methods 0.000 description 125
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 102
• UOZODPSAJZTQNH-LSWIJEOBSA-N paromomycin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)O[C@@H]1CO UOZODPSAJZTQNH-LSWIJEOBSA-N 0.000 description 91
• 239000000243 solution Substances 0.000 description 86
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 81
• 239000000203 mixture Substances 0.000 description 71
• 235000019439 ethyl acetate Nutrition 0.000 description 64
• 239000002904 solvent Substances 0.000 description 61
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 57
• 238000003818 flash chromatography Methods 0.000 description 57
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• 238000003756 stirring Methods 0.000 description 54
• 229960001914 paromomycin Drugs 0.000 description 53
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 52
• 108091032973 (ribonucleotides)n+m Proteins 0.000 description 51
• 239000012043 crude product Substances 0.000 description 51
• 238000003786 synthesis reaction Methods 0.000 description 47
• UOZODPSAJZTQNH-UHFFFAOYSA-N Paromomycin II Natural products NC1C(O)C(O)C(CN)OC1OC1C(O)C(OC2C(C(N)CC(N)C2O)OC2C(C(O)C(O)C(CO)O2)N)OC1CO UOZODPSAJZTQNH-UHFFFAOYSA-N 0.000 description 46
• 230000015572 biosynthetic process Effects 0.000 description 45
• 238000006243 chemical reaction Methods 0.000 description 44
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 44
• 239000012044 organic layer Substances 0.000 description 42
• 239000011541 reaction mixture Substances 0.000 description 42
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 41
• 239000000741 silica gel Substances 0.000 description 39
• 229910002027 silica gel Inorganic materials 0.000 description 39
• 239000007832 Na2SO4 Substances 0.000 description 38
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
• 229910052938 sodium sulfate Inorganic materials 0.000 description 38
• 235000011152 sodium sulphate Nutrition 0.000 description 38
• 238000002360 preparation method Methods 0.000 description 36
• 239000012267 brine Substances 0.000 description 30
• 238000001704 evaporation Methods 0.000 description 28
• 230000008020 evaporation Effects 0.000 description 28
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 26
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
• 230000001580 bacterial effect Effects 0.000 description 26
• 229910052739 hydrogen Chemical group 0.000 description 25
• 239000000047 product Substances 0.000 description 25
• 239000001257 hydrogen Chemical group 0.000 description 23
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
• 238000012512 characterization method Methods 0.000 description 21
• 108090000623 proteins and genes Proteins 0.000 description 21
• 102000004169 proteins and genes Human genes 0.000 description 21
• 239000000126 substance Substances 0.000 description 21
• 238000003556 assay Methods 0.000 description 20
• 241000588724 Escherichia coli Species 0.000 description 19
• 239000003242 anti bacterial agent Substances 0.000 description 19
• 125000004432 carbon atom Chemical group C* 0.000 description 19
• 239000013058 crude material Substances 0.000 description 19
• 239000011734 sodium Substances 0.000 description 19
• 229940088710 antibiotic agent Drugs 0.000 description 18
• 230000000694 effects Effects 0.000 description 18
• 239000003480 eluent Substances 0.000 description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 16
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 16
• 125000003342 alkenyl group Chemical group 0.000 description 16
• 230000027455 binding Effects 0.000 description 16
• 239000000463 material Substances 0.000 description 16
• 229940079593 drug Drugs 0.000 description 15
• 239000003814 drug Substances 0.000 description 15
• 238000004440 column chromatography Methods 0.000 description 14
• 125000000524 functional group Chemical group 0.000 description 14
• 230000004048 modification Effects 0.000 description 14
• 238000012986 modification Methods 0.000 description 14
• 230000002829 reductive effect Effects 0.000 description 14
• 101150065749 Churc1 gene Proteins 0.000 description 13
• 239000012298 atmosphere Substances 0.000 description 13
• 125000004122 cyclic group Chemical group 0.000 description 13
• 238000000605 extraction Methods 0.000 description 13
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 13
• 239000007787 solid Substances 0.000 description 13
• 0 *CC(C(C(C1*(*)*)N)N)OC1OC(C(CC(C1*)O)*(*)*)C1OC(C1O)OC(CO)C1N Chemical compound *CC(C(C(C1*(*)*)N)N)OC1OC(C(CC(C1*)O)*(*)*)C1OC(C1O)OC(CO)C1N 0.000 description 12
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
• 125000001931 aliphatic group Chemical group 0.000 description 12
• 238000009472 formulation Methods 0.000 description 12
• 125000000623 heterocyclic group Chemical group 0.000 description 12
• 238000000746 purification Methods 0.000 description 12
• 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
• 235000017557 sodium bicarbonate Nutrition 0.000 description 12
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
• 241000894006 Bacteria Species 0.000 description 11
• CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 11
• 229960000583 acetic acid Drugs 0.000 description 11
• 150000001299 aldehydes Chemical class 0.000 description 11
• 150000001412 amines Chemical class 0.000 description 11
• KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 10
• BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 10
• WLLIXJBWWFGEHT-UHFFFAOYSA-N [tert-butyl(dimethyl)silyl] trifluoromethanesulfonate Chemical compound CC(C)(C)[Si](C)(C)OS(=O)(=O)C(F)(F)F WLLIXJBWWFGEHT-UHFFFAOYSA-N 0.000 description 10
• 229940125877 compound 31 Drugs 0.000 description 10
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• 125000005647 linker group Chemical group 0.000 description 10
• KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
• 239000003826 tablet Substances 0.000 description 10
• 238000012360 testing method Methods 0.000 description 10
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
• QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
• 125000002723 alicyclic group Chemical group 0.000 description 9
• 125000003710 aryl alkyl group Chemical group 0.000 description 9
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• 238000013519 translation Methods 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
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• IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 7
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