JP2006505505A - 化合物 - Google Patents
化合物 Download PDFInfo
- Publication number
- JP2006505505A JP2006505505A JP2004516690A JP2004516690A JP2006505505A JP 2006505505 A JP2006505505 A JP 2006505505A JP 2004516690 A JP2004516690 A JP 2004516690A JP 2004516690 A JP2004516690 A JP 2004516690A JP 2006505505 A JP2006505505 A JP 2006505505A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- hydroxy
- substituted
- alkenyl
- amino
- Prior art date
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 title claims description 114
- 238000000034 method Methods 0.000 claims abstract description 91
- 241000124008 Mammalia Species 0.000 claims abstract description 10
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 8
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 8
- -1 amino, piperidyl Chemical group 0.000 claims description 265
- 125000000217 alkyl group Chemical group 0.000 claims description 155
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 69
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 239000001257 hydrogen Substances 0.000 claims description 37
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 36
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 36
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 34
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 33
- 125000003277 amino group Chemical group 0.000 claims description 33
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 29
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 25
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 24
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 23
- 125000000623 heterocyclic group Chemical group 0.000 claims description 23
- 125000004429 atom Chemical group 0.000 claims description 22
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 22
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 21
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 230000008569 process Effects 0.000 claims description 20
- 125000005137 alkenylsulfonyl group Chemical group 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000005843 halogen group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 17
- 229910052799 carbon Inorganic materials 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 15
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical group [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 14
- 229910052717 sulfur Inorganic materials 0.000 claims description 14
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 125000004043 oxo group Chemical group O=* 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 229910052727 yttrium Inorganic materials 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 229910052721 tungsten Inorganic materials 0.000 claims description 11
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 10
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 8
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 8
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 6
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 125000005035 acylthio group Chemical group 0.000 claims description 4
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 150000001540 azides Chemical class 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000005948 methanesulfonyloxy group Chemical group 0.000 claims description 4
- 125000004553 quinoxalin-5-yl group Chemical group N1=CC=NC2=C(C=CC=C12)* 0.000 claims description 4
- 125000003396 thiol group Chemical class [H]S* 0.000 claims description 4
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- KMAKPGNCADAYCQ-UHFFFAOYSA-N 4-[2-[3-hydroxy-4-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]piperidin-1-yl]ethyl]quinoline-6-carbonitrile Chemical compound O1CC(=O)NC2=NC(CNC3CCN(CCC=4C5=CC(=CC=C5N=CC=4)C#N)CC3O)=CC=C21 KMAKPGNCADAYCQ-UHFFFAOYSA-N 0.000 claims description 3
- JFMIRFVCFNYDCF-UHFFFAOYSA-N 4-[2-[3-hydroxy-4-[(3-oxo-4h-pyrido[3,2-b][1,4]thiazin-6-yl)methylamino]piperidin-1-yl]ethyl]quinoline-6-carbonitrile Chemical compound S1CC(=O)NC2=NC(CNC3CCN(CCC=4C5=CC(=CC=C5N=CC=4)C#N)CC3O)=CC=C21 JFMIRFVCFNYDCF-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 3
- JECYNCQXXKQDJN-UHFFFAOYSA-N 2-(2-methylhexan-2-yloxymethyl)oxirane Chemical group CCCCC(C)(C)OCC1CO1 JECYNCQXXKQDJN-UHFFFAOYSA-N 0.000 claims description 2
- BJIFLZHRWYQMPW-MOPGFXCFSA-N 6-[[[(3r,4s)-1-[2-(2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-10-yl)ethyl]-3-fluoropiperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@H]3CCN(CCC=4C5=C6OCCOC6=CC=C5N=CC=4)C[C@H]3F)=CC=C21 BJIFLZHRWYQMPW-MOPGFXCFSA-N 0.000 claims description 2
- LLJZXPJNGPCDII-UHFFFAOYSA-N 6-[[[1-[2-hydroxy-2-(2-methoxyquinolin-8-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]oxazin-3-one Chemical compound O1CC(=O)NC2=NC(CNC3CCN(CC3)CC(O)C3=CC=CC4=CC=C(N=C43)OC)=CC=C21 LLJZXPJNGPCDII-UHFFFAOYSA-N 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000005360 alkyl sulfoxide group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl group Chemical group 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 2
- 125000005361 aryl sulfoxide group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
- 125000004468 heterocyclylthio group Chemical group 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004546 quinazolin-4-yl group Chemical group N1=CN=C(C2=CC=CC=C12)* 0.000 claims description 2
- 125000004549 quinolin-4-yl group Chemical group N1=CC=C(C2=CC=CC=C12)* 0.000 claims description 2
- FLBAYUMRQUHISI-UHFFFAOYSA-N 1,8-naphthyridine Chemical compound N1=CC=CC2=CC=CN=C21 FLBAYUMRQUHISI-UHFFFAOYSA-N 0.000 claims 1
- VUKUJMNZZWMYJN-UHFFFAOYSA-N 1-[2-(9-chloro-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-10-yl)ethyl]-n-(2,3-dihydro-[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)piperidin-4-amine Chemical compound O1CCOC(C=N2)=C1C=C2CNC(CC1)CCN1CCC1=C2C(OCCO3)=C3C=CC2=NC=C1Cl VUKUJMNZZWMYJN-UHFFFAOYSA-N 0.000 claims 1
- JOHNUIYZVOWTBI-UHFFFAOYSA-N 4-[2-[4-[(3-oxo-4h-pyrido[3,2-b][1,4]oxazin-6-yl)methylamino]piperidin-1-yl]ethyl]quinoline-6-carbonitrile Chemical compound C1=C(C#N)C=C2C(CCN3CCC(CC3)NCC3=CC=C4OCC(NC4=N3)=O)=CC=NC2=C1 JOHNUIYZVOWTBI-UHFFFAOYSA-N 0.000 claims 1
- KNDHRVXJZTWBHE-HSALFYBXSA-N 6-[[[(3r,4r)-3-hydroxy-1-[(2r)-2-hydroxy-2-(2-methoxyquinolin-8-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CCN(C[C@H]3O)C[C@H](O)C3=CC=CC4=CC=C(N=C43)OC)=CC=C21 KNDHRVXJZTWBHE-HSALFYBXSA-N 0.000 claims 1
- VQBIJEJMPOAABY-AABGKKOBSA-N 6-[[[(3r,4s)-3-fluoro-1-[(2r)-2-hydroxy-2-(2-methoxyquinolin-8-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@H]3CCN(C[C@H]3F)C[C@H](O)C3=CC=CC4=CC=C(N=C43)OC)=CC=C21 VQBIJEJMPOAABY-AABGKKOBSA-N 0.000 claims 1
- VQBIJEJMPOAABY-ZCNNSNEGSA-N 6-[[[(3s,4r)-3-fluoro-1-[(2r)-2-hydroxy-2-(2-methoxyquinolin-8-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@@H]3CCN(C[C@@H]3F)C[C@H](O)C3=CC=CC4=CC=C(N=C43)OC)=CC=C21 VQBIJEJMPOAABY-ZCNNSNEGSA-N 0.000 claims 1
- KNDHRVXJZTWBHE-UFYCRDLUSA-N 6-[[[(3s,4s)-3-hydroxy-1-[(2r)-2-hydroxy-2-(2-methoxyquinolin-8-yl)ethyl]piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound S1CC(=O)NC2=NC(CN[C@H]3CCN(C[C@@H]3O)C[C@H](O)C3=CC=CC4=CC=C(N=C43)OC)=CC=C21 KNDHRVXJZTWBHE-UFYCRDLUSA-N 0.000 claims 1
- XOWLBHUIVFHSJS-UHFFFAOYSA-N 6-[[[1-(2-quinolin-4-ylethyl)piperidin-4-yl]amino]methyl]-4h-pyrido[3,2-b][1,4]thiazin-3-one Chemical compound C1=CC=C2C(CCN3CCC(CC3)NCC3=CC=C4SCC(NC4=N3)=O)=CC=NC2=C1 XOWLBHUIVFHSJS-UHFFFAOYSA-N 0.000 claims 1
- 241001024304 Mino Species 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 150000003053 piperidines Chemical class 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 174
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 117
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 93
- 238000006243 chemical reaction Methods 0.000 description 91
- 239000000243 solution Substances 0.000 description 90
- 239000000203 mixture Substances 0.000 description 88
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 85
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 63
- 239000007787 solid Substances 0.000 description 58
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 55
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 53
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 50
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
- 150000001412 amines Chemical class 0.000 description 46
- 239000000047 product Substances 0.000 description 44
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 43
- 150000002500 ions Chemical class 0.000 description 41
- 230000002829 reductive effect Effects 0.000 description 41
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- 150000001299 aldehydes Chemical class 0.000 description 30
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 239000000741 silica gel Substances 0.000 description 28
- 229910002027 silica gel Inorganic materials 0.000 description 28
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 26
- 235000019441 ethanol Nutrition 0.000 description 26
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 239000002253 acid Substances 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 22
- 235000019439 ethyl acetate Nutrition 0.000 description 22
- 238000003756 stirring Methods 0.000 description 22
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 19
- 239000003153 chemical reaction reagent Substances 0.000 description 17
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 17
- 229910052763 palladium Inorganic materials 0.000 description 17
- 239000011734 sodium Substances 0.000 description 17
- 239000012279 sodium borohydride Substances 0.000 description 17
- 229910000033 sodium borohydride Inorganic materials 0.000 description 17
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000002585 base Substances 0.000 description 15
- 230000009467 reduction Effects 0.000 description 15
- 238000006722 reduction reaction Methods 0.000 description 15
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 14
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 14
- 150000003839 salts Chemical class 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- 239000000543 intermediate Substances 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 238000004587 chromatography analysis Methods 0.000 description 11
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 11
- 235000019341 magnesium sulphate Nutrition 0.000 description 11
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000012267 brine Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 150000002118 epoxides Chemical class 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 description 9
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 9
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 241000283690 Bos taurus Species 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 229910052786 argon Inorganic materials 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 239000000284 extract Substances 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 239000000377 silicon dioxide Substances 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 125000003545 alkoxy group Chemical group 0.000 description 7
- PYXBJXCKGMSJMY-LSDHHAIUSA-N benzyl (3r,4s)-3-hydroxy-4-[(2-methylpropan-2-yl)oxycarbonylamino]piperidine-1-carboxylate Chemical compound C1[C@@H](O)[C@@H](NC(=O)OC(C)(C)C)CCN1C(=O)OCC1=CC=CC=C1 PYXBJXCKGMSJMY-LSDHHAIUSA-N 0.000 description 7
- 239000003638 chemical reducing agent Substances 0.000 description 7
- 238000007796 conventional method Methods 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000012948 isocyanate Substances 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 7
- 229910000104 sodium hydride Inorganic materials 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
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- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000002560 nitrile group Chemical group 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000000269 nucleophilic effect Effects 0.000 description 1
- 239000003883 ointment base Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
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- UQPUONNXJVWHRM-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 UQPUONNXJVWHRM-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- BZBAYMUKLAYQEO-UHFFFAOYSA-N phenylborane Chemical compound BC1=CC=CC=C1 BZBAYMUKLAYQEO-UHFFFAOYSA-N 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 1
- CPGRMGOILBSUQC-UHFFFAOYSA-N phosphoryl azide Chemical compound [N-]=[N+]=NP(=O)(N=[N+]=[N-])N=[N+]=[N-] CPGRMGOILBSUQC-UHFFFAOYSA-N 0.000 description 1
- 125000005633 phthalidyl group Chemical group 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
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- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- YHOBGCSGTGDMLF-UHFFFAOYSA-N sodium;di(propan-2-yl)azanide Chemical compound [Na+].CC(C)[N-]C(C)C YHOBGCSGTGDMLF-UHFFFAOYSA-N 0.000 description 1
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- 150000003457 sulfones Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 1
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- 239000011593 sulfur Substances 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
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- 239000007885 tablet disintegrant Substances 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- FJUUTKFGNMTODZ-HUUCEWRRSA-N tert-butyl (3r,4r)-3-(benzylamino)-4-hydroxypiperidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H](O)[C@@H]1NCC1=CC=CC=C1 FJUUTKFGNMTODZ-HUUCEWRRSA-N 0.000 description 1
- ZDIVZXZUIPLHNP-HUUCEWRRSA-N tert-butyl (3r,4r)-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate Chemical compound O[C@@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1NCC1=CC=CC=C1 ZDIVZXZUIPLHNP-HUUCEWRRSA-N 0.000 description 1
- KREUZCYJWPQPJX-HTQZYQBOSA-N tert-butyl (3r,4r)-4-amino-3-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](N)[C@H](O)C1 KREUZCYJWPQPJX-HTQZYQBOSA-N 0.000 description 1
- DUOWOUTVIPTSKH-LSDHHAIUSA-N tert-butyl (3s,4r)-3-fluoro-4-(phenylmethoxycarbonylamino)piperidine-1-carboxylate Chemical compound F[C@H]1CN(C(=O)OC(C)(C)C)CC[C@H]1NC(=O)OCC1=CC=CC=C1 DUOWOUTVIPTSKH-LSDHHAIUSA-N 0.000 description 1
- ZQRYPCAUVKVMLZ-JGVFFNPUSA-N tert-butyl (3s,4r)-4-amino-3-fluoropiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](N)[C@@H](F)C1 ZQRYPCAUVKVMLZ-JGVFFNPUSA-N 0.000 description 1
- CQWAEPLMMYOMSW-UHFFFAOYSA-N tert-butyl 2-[(4-aminophenyl)methyl]-3-fluoropiperidine-1-carboxylate Chemical class CC(C)(C)OC(=O)N1CCCC(F)C1CC1=CC=C(N)C=C1 CQWAEPLMMYOMSW-UHFFFAOYSA-N 0.000 description 1
- MMPWHAJQEZIIEH-UHFFFAOYSA-N tert-butyl 7-oxa-4-azabicyclo[4.1.0]heptane-4-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC2OC21 MMPWHAJQEZIIEH-UHFFFAOYSA-N 0.000 description 1
- MLTCALYMVICSBJ-JGVFFNPUSA-N tert-butyl n-[(3r,4s)-3-hydroxypiperidin-4-yl]carbamate Chemical class CC(C)(C)OC(=O)N[C@H]1CCNC[C@H]1O MLTCALYMVICSBJ-JGVFFNPUSA-N 0.000 description 1
- RWVJJORMCCGYKE-UHFFFAOYSA-N tert-butyl n-[1-[2-(9-chloro-2,3-dihydro-[1,4]dioxino[2,3-f]quinolin-10-yl)ethyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1CCC1=C(Cl)C=NC2=CC=C(OCCO3)C3=C12 RWVJJORMCCGYKE-UHFFFAOYSA-N 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
- XJPANWOKBWZVHC-UHFFFAOYSA-N tetrazol-2-amine Chemical compound NN1N=CN=N1 XJPANWOKBWZVHC-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 150000004897 thiazines Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 239000012049 topical pharmaceutical composition Substances 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- JKVRTUCVPZTEQZ-UHFFFAOYSA-N tributyltin azide Chemical compound CCCC[Sn](CCCC)(CCCC)N=[N+]=[N-] JKVRTUCVPZTEQZ-UHFFFAOYSA-N 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
- JPFRZOQKRGLTAC-UHFFFAOYSA-N trifluoromethanesulfonate;1-(trifluoromethyl)dibenzothiophen-5-ium Chemical compound [O-]S(=O)(=O)C(F)(F)F.[SH+]1C2=CC=CC=C2C2=C1C=CC=C2C(F)(F)F JPFRZOQKRGLTAC-UHFFFAOYSA-N 0.000 description 1
- QXXHXTRTGZBOGD-UHFFFAOYSA-M trifluoromethanesulfonate;5-(trifluoromethyl)dibenzothiophen-5-ium Chemical compound [O-]S(=O)(=O)C(F)(F)F.C1=CC=C2[S+](C(F)(F)F)C3=CC=CC=C3C2=C1 QXXHXTRTGZBOGD-UHFFFAOYSA-M 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PGAJYUDRKAPMPA-UHFFFAOYSA-N trimethylsilyl n-ethylcarbamate Chemical compound CCNC(=O)O[Si](C)(C)C PGAJYUDRKAPMPA-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 150000003952 β-lactams Chemical group 0.000 description 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- 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
- A61K31/02—Halogenated hydrocarbons
- A61K31/025—Halogenated hydrocarbons carbocyclic
- A61K31/03—Halogenated hydrocarbons carbocyclic aromatic
-
- 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
- A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39171002P | 2002-06-26 | 2002-06-26 | |
| PCT/EP2003/006754 WO2004002490A2 (en) | 2002-06-26 | 2003-06-25 | Piperidine compounds as antibacterials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006505505A true JP2006505505A (ja) | 2006-02-16 |
| JP2006505505A5 JP2006505505A5 (cg-RX-API-DMAC7.html) | 2006-06-15 |
Family
ID=30000740
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004516690A Pending JP2006505505A (ja) | 2002-06-26 | 2003-06-25 | 化合物 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7498326B2 (cg-RX-API-DMAC7.html) |
| EP (1) | EP1583537A3 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2006505505A (cg-RX-API-DMAC7.html) |
| AR (1) | AR040336A1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU2003238054A1 (cg-RX-API-DMAC7.html) |
| TW (1) | TW200409637A (cg-RX-API-DMAC7.html) |
| WO (1) | WO2004002490A2 (cg-RX-API-DMAC7.html) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010513255A (ja) * | 2006-12-15 | 2010-04-30 | アストラゼネカ アクチボラグ | ２−キノリノン及び２−キノキサリノン誘導体と抗菌剤としてのそれらの使用 |
| JP2010524884A (ja) * | 2007-04-20 | 2010-07-22 | グラクソ グループ リミテッド | 抗菌剤としての三環式含窒素化合物 |
| JP2012511566A (ja) * | 2008-12-12 | 2012-05-24 | アクテリオン ファーマシューティカルズ リミテッド | ５−アミノ−２−（１−ヒドロキシ−エチル）−テトラヒドロピラン誘導体 |
Families Citing this family (70)
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2010513255A (ja) * | 2006-12-15 | 2010-04-30 | アストラゼネカ アクチボラグ | ２−キノリノン及び２−キノキサリノン誘導体と抗菌剤としてのそれらの使用 |
| JP2010524884A (ja) * | 2007-04-20 | 2010-07-22 | グラクソ グループ リミテッド | 抗菌剤としての三環式含窒素化合物 |
| JP2012511566A (ja) * | 2008-12-12 | 2012-05-24 | アクテリオン ファーマシューティカルズ リミテッド | ５−アミノ−２−（１−ヒドロキシ−エチル）−テトラヒドロピラン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1583537A2 (en) | 2005-10-12 |
| WO2004002490A3 (en) | 2005-10-27 |
| AR040336A1 (es) | 2005-03-30 |
| US7498326B2 (en) | 2009-03-03 |
| AU2003238054A8 (en) | 2004-01-19 |
| AU2003238054A1 (en) | 2004-01-19 |
| WO2004002490A2 (en) | 2004-01-08 |
| TW200409637A (en) | 2004-06-16 |
| EP1583537A3 (en) | 2005-12-14 |
| US20060058287A1 (en) | 2006-03-16 |
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