MX2007015173A - Penemes triciclicos de 6-alquilideno como inhibidores de beta-lactamasas clase d. - Google Patents
Penemes triciclicos de 6-alquilideno como inhibidores de beta-lactamasas clase d.Info
- Publication number
- MX2007015173A MX2007015173A MX2007015173A MX2007015173A MX2007015173A MX 2007015173 A MX2007015173 A MX 2007015173A MX 2007015173 A MX2007015173 A MX 2007015173A MX 2007015173 A MX2007015173 A MX 2007015173A MX 2007015173 A MX2007015173 A MX 2007015173A
- Authority
- MX
- Mexico
- Prior art keywords
- optionally substituted
- oxo
- alkyl
- ene
- thia
- Prior art date
Links
- 239000003112 inhibitor Substances 0.000 title abstract description 5
- 102000006635 beta-lactamase Human genes 0.000 title description 14
- 108020004256 Beta-lactamase Proteins 0.000 title description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 64
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 55
- 239000003782 beta lactam antibiotic agent Substances 0.000 claims abstract description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
- 102000004190 Enzymes Human genes 0.000 claims abstract description 15
- 108090000790 Enzymes Proteins 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
- -1 [1,3] benzothiazol-2-ylmethylene Chemical group 0.000 claims description 117
- 239000002253 acid Substances 0.000 claims description 104
- 229910052799 carbon Inorganic materials 0.000 claims description 69
- 159000000000 sodium salts Chemical class 0.000 claims description 50
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 45
- 238000000034 method Methods 0.000 claims description 44
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000001721 carbon Chemical group 0.000 claims description 36
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 31
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- 229910052757 nitrogen Inorganic materials 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- FYZUENZXIZCLAZ-UHFFFAOYSA-N 2-methylhept-2-enoic acid Chemical compound CCCCC=C(C)C(O)=O FYZUENZXIZCLAZ-UHFFFAOYSA-N 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 18
- 239000002132 β-lactam antibiotic Substances 0.000 claims description 18
- 229940124586 β-lactam antibiotics Drugs 0.000 claims description 18
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000003107 substituted aryl group Chemical group 0.000 claims description 12
- 125000003003 spiro group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 10
- 238000006664 bond formation reaction Methods 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 8
- 125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 8
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 8
- 125000005325 aryloxy aryl group Chemical group 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000002950 monocyclic group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 5
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 150000002431 hydrogen Chemical group 0.000 claims description 4
- 238000001727 in vivo Methods 0.000 claims description 4
- DMJNNHOOLUXYBV-PQTSNVLCSA-N meropenem Chemical compound C=1([C@H](C)[C@@H]2[C@H](C(N2C=1C(O)=O)=O)[C@H](O)C)S[C@@H]1CN[C@H](C(=O)N(C)C)C1 DMJNNHOOLUXYBV-PQTSNVLCSA-N 0.000 claims description 4
- OZBZQLHFHVWHPS-UHFFFAOYSA-N 1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CCC2CCN12 OZBZQLHFHVWHPS-UHFFFAOYSA-N 0.000 claims description 3
- MGADZUXDNSDTHW-UHFFFAOYSA-N 2H-pyran Chemical compound C1OC=CC=C1 MGADZUXDNSDTHW-UHFFFAOYSA-N 0.000 claims description 3
- JKRKHPFTFGBKCV-UHFFFAOYSA-N 6-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CSC2C(=O)CN12 JKRKHPFTFGBKCV-UHFFFAOYSA-N 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 3
- 125000002619 bicyclic group Chemical group 0.000 claims description 3
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 3
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 3
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 3
- DUNKKIRUWZSMPT-UHFFFAOYSA-N 7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CSC2CC(=O)N12 DUNKKIRUWZSMPT-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- 125000005605 benzo group Chemical group 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- 239000003451 thiazide diuretic agent Substances 0.000 claims description 2
- YJHLAPIOTYDKSI-VYLZPFMQSA-N (5r,6z)-7-oxo-6-([1,3]thiazolo[3,2-a]benzimidazol-7-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1([C@@H]2SC=C1C(=O)O)C(=O)\C2=C\C(C=C12)=CC=C1N=C1N2C=CS1 YJHLAPIOTYDKSI-VYLZPFMQSA-N 0.000 claims 1
- LVDAGEHCAGXUMS-UITAMQMPSA-N (6z)-7-oxo-6-([1,3]thiazolo[3,2-a]benzimidazol-2-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound S1C2=NC3=CC=CC=C3N2C=C1/C=C1/C(=O)N2C1SC=C2C(=O)O LVDAGEHCAGXUMS-UITAMQMPSA-N 0.000 claims 1
- QOPVVFKNSPILEH-UHFFFAOYSA-N 7-oxo-6-(quinolin-2-ylmethylidene)-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound N1=C(C=CC2=CC=CC=C12)C=C1C2SC=C(N2C1=O)C(=O)O QOPVVFKNSPILEH-UHFFFAOYSA-N 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 239000000178 monomer Substances 0.000 claims 1
- 125000005017 substituted alkenyl group Chemical group 0.000 claims 1
- 206010034133 Pathogen resistance Diseases 0.000 abstract description 4
- 239000010752 BS 2869 Class D Substances 0.000 abstract 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 422
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 291
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 214
- 239000011541 reaction mixture Substances 0.000 description 176
- 235000019439 ethyl acetate Nutrition 0.000 description 142
- 239000000243 solution Substances 0.000 description 135
- 239000000203 mixture Substances 0.000 description 131
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 118
- 238000002360 preparation method Methods 0.000 description 116
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 114
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 108
- 239000007787 solid Substances 0.000 description 108
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 102
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 101
- 229910001868 water Inorganic materials 0.000 description 100
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 93
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 91
- 239000000047 product Substances 0.000 description 90
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 74
- 230000002829 reductive effect Effects 0.000 description 72
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 69
- 239000012044 organic layer Substances 0.000 description 64
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 63
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
- 239000000706 filtrate Substances 0.000 description 59
- 238000006243 chemical reaction Methods 0.000 description 57
- 239000010410 layer Substances 0.000 description 57
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 238000005481 NMR spectroscopy Methods 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 47
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 42
- 239000011780 sodium chloride Substances 0.000 description 39
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 38
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 37
- 235000019341 magnesium sulphate Nutrition 0.000 description 37
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 35
- 239000002244 precipitate Substances 0.000 description 32
- 125000001424 substituent group Chemical group 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 239000008363 phosphate buffer Substances 0.000 description 31
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical class O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
- 238000010898 silica gel chromatography Methods 0.000 description 27
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 238000004440 column chromatography Methods 0.000 description 25
- 239000013078 crystal Substances 0.000 description 25
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 description 23
- 239000011734 sodium Substances 0.000 description 23
- 238000001816 cooling Methods 0.000 description 22
- 239000012300 argon atmosphere Substances 0.000 description 21
- 239000012071 phase Substances 0.000 description 21
- 230000002441 reversible effect Effects 0.000 description 21
- 239000011347 resin Substances 0.000 description 20
- 229920005989 resin Polymers 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000008367 deionised water Substances 0.000 description 18
- 229910021641 deionized water Inorganic materials 0.000 description 18
- 229910001623 magnesium bromide Inorganic materials 0.000 description 18
- 239000000741 silica gel Substances 0.000 description 18
- 229910002027 silica gel Inorganic materials 0.000 description 18
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 17
- 239000007864 aqueous solution Substances 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 239000012429 reaction media Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium on carbon Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
- 239000012141 concentrate Substances 0.000 description 14
- 235000008504 concentrate Nutrition 0.000 description 14
- 239000000843 powder Substances 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 13
- 239000011888 foil Substances 0.000 description 13
- 239000002274 desiccant Substances 0.000 description 12
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
- 229910052938 sodium sulfate Inorganic materials 0.000 description 11
- 235000011152 sodium sulphate Nutrition 0.000 description 11
- 150000001299 aldehydes Chemical class 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 229960002292 piperacillin Drugs 0.000 description 9
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 9
- VQWYSTGIQKLGAL-WVZVXSGGSA-N (5r,6s)-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CS[C@@H]2[C@@H](Br)C(=O)N12 VQWYSTGIQKLGAL-WVZVXSGGSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 235000015320 potassium carbonate Nutrition 0.000 description 8
- VQWYSTGIQKLGAL-UHFFFAOYSA-N 6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid Chemical compound OC(=O)C1=CSC2C(Br)C(=O)N12 VQWYSTGIQKLGAL-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000003781 beta lactamase inhibitor Substances 0.000 description 7
- 229940126813 beta-lactamase inhibitor Drugs 0.000 description 7
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 7
- 125000004494 ethyl ester group Chemical group 0.000 description 7
- 238000003818 flash chromatography Methods 0.000 description 7
- 239000012448 Lithium borohydride Substances 0.000 description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 238000004007 reversed phase HPLC Methods 0.000 description 6
- 238000002390 rotary evaporation Methods 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 229930182555 Penicillin Natural products 0.000 description 5
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 5
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 5
- 230000000844 anti-bacterial effect Effects 0.000 description 5
- SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 5
- 150000004702 methyl esters Chemical class 0.000 description 5
- 125000004433 nitrogen atom Chemical group N* 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- KJUGUADJHNHALS-UHFFFAOYSA-N 1H-tetrazole Chemical compound C=1N=NNN=1 KJUGUADJHNHALS-UHFFFAOYSA-N 0.000 description 4
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 4
- 229930186147 Cephalosporin Natural products 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 4
- 229960003022 amoxicillin Drugs 0.000 description 4
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 4
- 150000007942 carboxylates Chemical class 0.000 description 4
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- 238000004587 chromatography analysis Methods 0.000 description 4
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- JGZKUKYUQJUUNE-UHFFFAOYSA-L magnesium;ethoxyethane;dibromide Chemical compound [Mg+2].[Br-].[Br-].CCOCC JGZKUKYUQJUUNE-UHFFFAOYSA-L 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 4
- 150000002960 penicillins Chemical class 0.000 description 4
- 235000011181 potassium carbonates Nutrition 0.000 description 4
- WQWSMVWRGAFPJX-UHFFFAOYSA-N (3-amino-1h-1,2,4-triazol-5-yl)methanol Chemical compound NC1=NNC(CO)=N1 WQWSMVWRGAFPJX-UHFFFAOYSA-N 0.000 description 3
- XHIQSYLMJAVDLM-UHFFFAOYSA-N (4-nitrophenyl)methyl 2-methylhept-2-enoate Chemical compound CCCCC=C(C)C(=O)OCC1=CC=C([N+]([O-])=O)C=C1 XHIQSYLMJAVDLM-UHFFFAOYSA-N 0.000 description 3
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
- A61K31/424—Oxazoles condensed with heterocyclic ring systems, e.g. clavulanic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Bioinformatics & Cheminformatics (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 |
|---|---|---|---|
| US68622105P | 2005-06-01 | 2005-06-01 | |
| PCT/US2006/020410 WO2007030166A2 (en) | 2005-06-01 | 2006-05-25 | TRICYCLIC 6-ALKYLIDENE-PENEMS AS CLASS-D β-LACTAMASES INHIBITORS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2007015173A true MX2007015173A (es) | 2008-02-15 |
Family
ID=37836305
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2007015173A MX2007015173A (es) | 2005-06-01 | 2006-05-25 | Penemes triciclicos de 6-alquilideno como inhibidores de beta-lactamasas clase d. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US20060276446A1 (enExample) |
| EP (1) | EP1885358A2 (enExample) |
| JP (1) | JP2008542376A (enExample) |
| CN (1) | CN101189010A (enExample) |
| AR (1) | AR054467A1 (enExample) |
| AU (1) | AU2006287938A1 (enExample) |
| BR (1) | BRPI0611491A2 (enExample) |
| CA (1) | CA2610478A1 (enExample) |
| GT (1) | GT200600235A (enExample) |
| MX (1) | MX2007015173A (enExample) |
| PE (1) | PE20070010A1 (enExample) |
| SV (1) | SV2007002555A (enExample) |
| TW (1) | TW200716104A (enExample) |
| WO (1) | WO2007030166A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
| US8945652B2 (en) | 2005-11-23 | 2015-02-03 | The Coca-Cola Company | High-potency sweetener for weight management and compositions sweetened therewith |
| US8524304B2 (en) * | 2005-11-23 | 2013-09-03 | The Coca-Cola Company | High-potency sweetener composition with probiotics/prebiotics and compositions sweetened therewith |
| US8512789B2 (en) * | 2005-11-23 | 2013-08-20 | The Coca-Cola Company | High-potency sweetener composition with dietary fiber and compositions sweetened therewith |
| JP2012121809A (ja) * | 2009-02-26 | 2012-06-28 | Eisai R & D Management Co Ltd | 多環式化合物の製造法およびその中間体 |
| US20110288063A1 (en) * | 2010-05-19 | 2011-11-24 | Naeja Pharmaceutical Inc. | Novel fused bridged bicyclic heteroaryl substituted 6-alkylidene penems as potent beta-lactamase inhibitors |
| CN104341345B (zh) * | 2014-10-24 | 2016-03-23 | 海门海康生物医药科技有限公司 | 一种2-甲氧基-6-酮-5,6,7,8-四氢喹啉的合成方法 |
| WO2020179859A1 (ja) | 2019-03-06 | 2020-09-10 | 第一三共株式会社 | ピロロピラゾール誘導体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2206502T3 (es) * | 1994-04-25 | 2004-05-16 | Smithkline Beecham Plc | Formulaciones farmaceuticas que contienen un penem inhibidor de beta-lactamasa en combinacion con un antibiotico de beta-lactama y su uso en el tratamiento de infecciones bacterianas. |
| US20040132706A1 (en) * | 2001-10-05 | 2004-07-08 | Daniela Salvemini | Composition comprising a catalyst for the dismutation of superoxide and use of the composition for preventing and treating hypotension |
| US20040132708A1 (en) * | 2002-05-01 | 2004-07-08 | Wyeth | Process for preparing 6-alkylidene penem derivatives |
| AR039774A1 (es) * | 2002-05-01 | 2005-03-02 | Wyeth Corp | 6-alquiliden-penems biciclicos como inhibidores de beta-lactamasas |
| AR039476A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | Proceso para preparar derivados de 6-alquiliden penem |
| AR039475A1 (es) * | 2002-05-01 | 2005-02-23 | Wyeth Corp | 6-alquiliden-penems triciclicos como inhibidores de beta-lactamasa |
| TW200716102A (en) * | 2005-06-01 | 2007-05-01 | Wyeth Corp | Bicyclic 6-alkylidene-penems as class-D β -lactamases inhibitors |
-
2006
- 2006-05-22 TW TW095118171A patent/TW200716104A/zh unknown
- 2006-05-25 MX MX2007015173A patent/MX2007015173A/es unknown
- 2006-05-25 BR BRPI0611491-1A patent/BRPI0611491A2/pt not_active IP Right Cessation
- 2006-05-25 JP JP2008514712A patent/JP2008542376A/ja not_active Withdrawn
- 2006-05-25 AU AU2006287938A patent/AU2006287938A1/en not_active Abandoned
- 2006-05-25 CN CNA2006800193154A patent/CN101189010A/zh active Pending
- 2006-05-25 WO PCT/US2006/020410 patent/WO2007030166A2/en not_active Ceased
- 2006-05-25 EP EP06824758A patent/EP1885358A2/en not_active Withdrawn
- 2006-05-25 CA CA002610478A patent/CA2610478A1/en not_active Abandoned
- 2006-05-31 PE PE2006000563A patent/PE20070010A1/es not_active Application Discontinuation
- 2006-05-31 SV SV2006002555A patent/SV2007002555A/es unknown
- 2006-05-31 US US11/444,346 patent/US20060276446A1/en not_active Abandoned
- 2006-06-01 GT GT200600235A patent/GT200600235A/es unknown
- 2006-06-01 AR ARP060102292A patent/AR054467A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| WO2007030166A2 (en) | 2007-03-15 |
| WO2007030166A3 (en) | 2007-05-24 |
| EP1885358A2 (en) | 2008-02-13 |
| JP2008542376A (ja) | 2008-11-27 |
| GT200600235A (es) | 2007-03-29 |
| US20060276446A1 (en) | 2006-12-07 |
| SV2007002555A (es) | 2007-02-02 |
| AU2006287938A1 (en) | 2007-03-15 |
| AR054467A1 (es) | 2007-06-27 |
| CN101189010A (zh) | 2008-05-28 |
| CA2610478A1 (en) | 2007-03-15 |
| TW200716104A (en) | 2007-05-01 |
| BRPI0611491A2 (pt) | 2010-12-21 |
| PE20070010A1 (es) | 2007-01-12 |
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