ZA200308696B - Nitrogen-containing bicyclic heterocycles for use as antibacterials. - Google Patents
Nitrogen-containing bicyclic heterocycles for use as antibacterials. Download PDFInfo
- Publication number
- ZA200308696B ZA200308696B ZA200308696A ZA200308696A ZA200308696B ZA 200308696 B ZA200308696 B ZA 200308696B ZA 200308696 A ZA200308696 A ZA 200308696A ZA 200308696 A ZA200308696 A ZA 200308696A ZA 200308696 B ZA200308696 B ZA 200308696B
- Authority
- ZA
- South Africa
- Prior art keywords
- amino
- alkyl
- dihydro
- amide
- hydroxy
- Prior art date
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- 230000000844 anti-bacterial effect Effects 0.000 title description 3
- 229940088710 antibiotic agent Drugs 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 158
- -1 amino, piperidyl Chemical group 0.000 claims description 135
- 125000003342 alkenyl group Chemical group 0.000 claims description 77
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 58
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 54
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 48
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 44
- 125000003118 aryl group Chemical group 0.000 claims description 42
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims description 39
- 125000005092 alkenyloxycarbonyl group Chemical group 0.000 claims description 39
- 125000003277 amino group Chemical group 0.000 claims description 39
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 239000001257 hydrogen Substances 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 29
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 28
- 125000005843 halogen group Chemical group 0.000 claims description 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 14
- 125000006574 non-aromatic ring group Chemical group 0.000 claims description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 101150020251 NR13 gene Proteins 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- 125000004043 oxo group Chemical group O=* 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 7
- 125000005605 benzo group Chemical group 0.000 claims description 7
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 241000124008 Mammalia Species 0.000 claims description 5
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 5
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 5
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
- 125000001414 1,2,4-triazol-5-yl group Chemical group [H]N1N=C([H])N=C1[*] 0.000 claims description 4
- 208000035143 Bacterial infection Diseases 0.000 claims description 4
- 101100240517 Caenorhabditis elegans nhr-11 gene Proteins 0.000 claims description 4
- 101000585507 Solanum tuberosum Cytochrome b-c1 complex subunit 7 Proteins 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
- 125000005035 acylthio group Chemical group 0.000 claims description 3
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 125000006413 ring segment Chemical group 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000005129 aryl carbonyl 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
- 125000002527 bicyclic carbocyclic group Chemical group 0.000 claims description 2
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 150000003950 cyclic amides Chemical class 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 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
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000002883 imidazolyl group Chemical group 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 2
- VUHCPMIDSUGHNO-UHFFFAOYSA-N 6-methoxy-1,5-naphthyridin-4-amine Chemical compound N1=CC=C(N)C2=NC(OC)=CC=C21 VUHCPMIDSUGHNO-UHFFFAOYSA-N 0.000 claims 22
- NZNMSOFKMUBTKW-UHFFFAOYSA-N Cyclohexanecarboxylic acid Natural products OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims 11
- VZFUCHSFHOYXIS-UHFFFAOYSA-N cycloheptane carboxylic acid Natural products OC(=O)C1CCCCCC1 VZFUCHSFHOYXIS-UHFFFAOYSA-N 0.000 claims 9
- UDQAHFTWCBMBAL-UHFFFAOYSA-N 6,8-difluoroquinolin-4-amine Chemical compound C1=C(F)C=C2C(N)=CC=NC2=C1F UDQAHFTWCBMBAL-UHFFFAOYSA-N 0.000 claims 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- YAIJZMMUWSFXQD-QAQDUYKDSA-N C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)C=C21 Chemical compound C1=CC2=NSN=C2C=C1CN[C@H](CC1)CC[C@@H]1C(=O)NC1=CC=NC2=CC=C(OC)C=C21 YAIJZMMUWSFXQD-QAQDUYKDSA-N 0.000 claims 1
- CFBZHYHIGXNJHA-JCNLHEQBSA-N C1=CN=C2NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC2=C1 Chemical compound C1=CN=C2NC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CC2=C1 CFBZHYHIGXNJHA-JCNLHEQBSA-N 0.000 claims 1
- VUWIHBMHDCCKDK-KESTWPANSA-N COc1ccc2nccc(C(=O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 Chemical compound COc1ccc2nccc(C(=O)C[C@H]3CC[C@@H](CC3)NCc3ccc4OCCOc4c3)c2c1 VUWIHBMHDCCKDK-KESTWPANSA-N 0.000 claims 1
- WESVMUHKPRCJHK-KOMQPUFPSA-N N([C@H]1CC[C@@H](CC1)C(=O)NC1=CC=NC2=CC=C(N=C21)OC)CC(C(=C1)[N+]([O-])=O)=CC2=C1OCO2 Chemical compound N([C@H]1CC[C@@H](CC1)C(=O)NC1=CC=NC2=CC=C(N=C21)OC)CC(C(=C1)[N+]([O-])=O)=CC2=C1OCO2 WESVMUHKPRCJHK-KOMQPUFPSA-N 0.000 claims 1
- GINYYMFAGWWUOX-SHTZXODSSA-N N1=C2SN=NC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 Chemical compound N1=C2SN=NC2=CC(CN[C@H]2CC[C@@H](CC2)C(=O)NC2=CC=NC3=CC=C(N=C32)OC)=C1 GINYYMFAGWWUOX-SHTZXODSSA-N 0.000 claims 1
- INPHYSUGIAWTBU-IYARVYRRSA-N O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=C(F)C=C(C=C43)OC)=CC=C21 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=C(F)C=C(C=C43)OC)=CC=C21 INPHYSUGIAWTBU-IYARVYRRSA-N 0.000 claims 1
- PBMILUQGLGSJJH-QAQDUYKDSA-N O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CN=C21 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(N=C43)OC)=CN=C21 PBMILUQGLGSJJH-QAQDUYKDSA-N 0.000 claims 1
- RFIZPVKNXMEZQV-HAQNSBGRSA-N OC(=O)[C@H]1CC[C@@H](CC1)NCc1cc(=O)n2ccccc2n1 Chemical compound OC(=O)[C@H]1CC[C@@H](CC1)NCc1cc(=O)n2ccccc2n1 RFIZPVKNXMEZQV-HAQNSBGRSA-N 0.000 claims 1
- ZZRDGWHDXUEJBL-HAQNSBGRSA-N OC(=O)[C@H]1CC[C@@H](CC1)NCc1ccc2SCC(=O)Nc2c1 Chemical compound OC(=O)[C@H]1CC[C@@H](CC1)NCc1ccc2SCC(=O)Nc2c1 ZZRDGWHDXUEJBL-HAQNSBGRSA-N 0.000 claims 1
- BSSINILOHMJKKK-XYPYZODXSA-N OC(=O)[C@H]1CC[C@@H](CC1)NCc1cnc2scnc2c1 Chemical compound OC(=O)[C@H]1CC[C@@H](CC1)NCc1cnc2scnc2c1 BSSINILOHMJKKK-XYPYZODXSA-N 0.000 claims 1
- OSVVTVLREDJKKV-WGSAOQKQSA-N chembl1926762 Chemical compound O1CCOC2=CC(CN[C@H]3CC[C@@H](CC3)C(=O)NC3=CC=NC4=CC=C(C=C43)OC)=CC=C21 OSVVTVLREDJKKV-WGSAOQKQSA-N 0.000 claims 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims 1
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims 1
- 238000005984 hydrogenation reaction Methods 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 description 3
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 3
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 description 3
- 125000005936 piperidyl group Chemical group 0.000 description 3
- 125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 101000983970 Conus catus Alpha-conotoxin CIB Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- UEZROEGYRDHMRV-UHFFFAOYSA-N [1,3]thiazolo[3,2-a]pyrimidin-5-one Chemical compound O=C1C=CN=C2SC=CN12 UEZROEGYRDHMRV-UHFFFAOYSA-N 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 125000004190 benzothiazol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N=C(*)SC2=C1[H] 0.000 description 1
- 125000004540 benzothiazol-5-yl group Chemical group S1C=NC2=C1C=CC(=C2)* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 125000004242 cinnolin-3-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)N=NC2=C1[H] 0.000 description 1
- 125000004310 dioxan-2-yl group Chemical group [H]C1([H])OC([H])([H])C([H])(*)OC1([H])[H] 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical group FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 description 1
- 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004551 isoquinolin-3-yl group Chemical group C1=NC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical compound N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 1
- 125000004526 pyridazin-2-yl group Chemical group N1N(C=CC=C1)* 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 description 1
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000004159 quinolin-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C([H])C(*)=NC2=C1[H] 0.000 description 1
- 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 description 1
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000005415 substituted alkoxy group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
-
- 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
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- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
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- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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GBGB0112834.7A GB0112834D0 (en) | 2001-05-25 | 2001-05-25 | Medicaments |
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ZA200308696A ZA200308696B (en) | 2001-05-25 | 2003-11-07 | Nitrogen-containing bicyclic heterocycles for use as antibacterials. |
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US (2) | US7141564B2 (hu) |
EP (1) | EP1399443B1 (hu) |
JP (2) | JP4463565B2 (hu) |
KR (1) | KR20040010654A (hu) |
CN (1) | CN1535272A (hu) |
AR (1) | AR038172A1 (hu) |
AT (1) | ATE380812T1 (hu) |
AU (1) | AU2002367697A1 (hu) |
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CA (1) | CA2448525A1 (hu) |
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CZ (1) | CZ20033202A3 (hu) |
DE (1) | DE60224039T2 (hu) |
ES (1) | ES2298439T3 (hu) |
GB (1) | GB0112834D0 (hu) |
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PL (1) | PL367079A1 (hu) |
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FR2844268B1 (fr) | 2002-09-11 | 2004-10-22 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leurs procedes et intermediaires de preparation et les compositions qui les contiennent |
FR2844270B1 (fr) | 2002-09-11 | 2006-05-19 | Aventis Pharma Sa | Derives de la quinolyl propyl piperidine, leur procede et intermediaires de preparation et les compositions qui les contiennent |
DE50312598D1 (de) | 2002-10-10 | 2010-05-20 | Morphochem Ag Komb Chemie | Neue verbindungen mit antibakterieller aktivität |
AR042486A1 (es) * | 2002-12-18 | 2005-06-22 | Glaxo Group Ltd | Compuesto de quinolina y naftiridina halosustituido en la posicion 3, procedimiento para preparar el compuesto, composicion farmaceutica que lo comprende y su uso para preparar dicha composicion . |
DE10316081A1 (de) | 2003-04-08 | 2004-10-21 | Morphochem AG Aktiengesellschaft für kombinatorische Chemie | Neue Verbindungen mit antibakterieller Aktivität |
-
2001
- 2001-05-25 GB GBGB0112834.7A patent/GB0112834D0/en not_active Ceased
-
2002
- 2002-05-23 TW TW091110839A patent/TWI232219B/zh not_active IP Right Cessation
- 2002-05-23 AR ARP020101914A patent/AR038172A1/es not_active Application Discontinuation
- 2002-05-24 EP EP02807202A patent/EP1399443B1/en not_active Expired - Lifetime
- 2002-05-24 BR BR0210016-9A patent/BR0210016A/pt not_active IP Right Cessation
- 2002-05-24 CN CNA028146689A patent/CN1535272A/zh active Pending
- 2002-05-24 AU AU2002367697A patent/AU2002367697A1/en not_active Abandoned
- 2002-05-24 IL IL15886902A patent/IL158869A0/xx unknown
- 2002-05-24 AT AT02807202T patent/ATE380812T1/de not_active IP Right Cessation
- 2002-05-24 WO PCT/EP2002/005708 patent/WO2003087098A1/en active IP Right Grant
- 2002-05-24 HU HU0400017A patent/HUP0400017A2/hu unknown
- 2002-05-24 CA CA002448525A patent/CA2448525A1/en not_active Abandoned
- 2002-05-24 ES ES02807202T patent/ES2298439T3/es not_active Expired - Lifetime
- 2002-05-24 JP JP2003584054A patent/JP4463565B2/ja not_active Expired - Fee Related
- 2002-05-24 CZ CZ20033202A patent/CZ20033202A3/cs unknown
- 2002-05-24 PL PL02367079A patent/PL367079A1/xx not_active Application Discontinuation
- 2002-05-24 MX MXPA03010790A patent/MXPA03010790A/es unknown
- 2002-05-24 KR KR10-2003-7015379A patent/KR20040010654A/ko not_active Application Discontinuation
- 2002-05-24 US US10/478,154 patent/US7141564B2/en not_active Expired - Fee Related
- 2002-05-24 DE DE60224039T patent/DE60224039T2/de not_active Expired - Lifetime
-
2003
- 2003-11-07 ZA ZA200308696A patent/ZA200308696B/en unknown
- 2003-11-18 CO CO03101671A patent/CO5540344A2/es not_active Application Discontinuation
- 2003-11-21 NO NO20035190A patent/NO20035190D0/no not_active Application Discontinuation
-
2006
- 2006-11-22 US US11/604,045 patent/US20070135422A1/en not_active Abandoned
-
2009
- 2009-11-13 JP JP2009259981A patent/JP2010031057A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
MXPA03010790A (es) | 2004-03-02 |
JP2005519981A (ja) | 2005-07-07 |
US20070135422A1 (en) | 2007-06-14 |
EP1399443A1 (en) | 2004-03-24 |
IL158869A0 (en) | 2004-05-12 |
US20040171620A1 (en) | 2004-09-02 |
JP4463565B2 (ja) | 2010-05-19 |
ATE380812T1 (de) | 2007-12-15 |
CN1535272A (zh) | 2004-10-06 |
KR20040010654A (ko) | 2004-01-31 |
JP2010031057A (ja) | 2010-02-12 |
CZ20033202A3 (cs) | 2004-08-18 |
WO2003087098A1 (en) | 2003-10-23 |
ES2298439T3 (es) | 2008-05-16 |
PL367079A1 (en) | 2005-02-21 |
HUP0400017A2 (hu) | 2004-06-28 |
BR0210016A (pt) | 2004-06-15 |
DE60224039T2 (de) | 2008-11-27 |
CA2448525A1 (en) | 2003-10-23 |
EP1399443B1 (en) | 2007-12-12 |
GB0112834D0 (en) | 2001-07-18 |
US7141564B2 (en) | 2006-11-28 |
AU2002367697A1 (en) | 2003-10-27 |
DE60224039D1 (de) | 2008-01-24 |
NO20035190D0 (no) | 2003-11-21 |
TWI232219B (en) | 2005-05-11 |
AR038172A1 (es) | 2005-01-05 |
CO5540344A2 (es) | 2005-07-29 |
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