JP4462926B2 - 新規な抗細菌性複素環式化合物 - Google Patents
新規な抗細菌性複素環式化合物 Download PDFInfo
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- JP4462926B2 JP4462926B2 JP2003506265A JP2003506265A JP4462926B2 JP 4462926 B2 JP4462926 B2 JP 4462926B2 JP 2003506265 A JP2003506265 A JP 2003506265A JP 2003506265 A JP2003506265 A JP 2003506265A JP 4462926 B2 JP4462926 B2 JP 4462926B2
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- Prior art keywords
- ethyl
- oxo
- carboxy
- uracil
- methylanilino
- 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.)
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- 230000000844 anti-bacterial effect Effects 0.000 title description 14
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 347
- -1 Substituted-3-carboxy-4-pyridone Chemical class 0.000 claims description 126
- 239000000203 mixture Substances 0.000 claims description 125
- 125000000217 alkyl group Chemical group 0.000 claims description 73
- 125000005843 halogen group Chemical group 0.000 claims description 65
- 230000001580 bacterial effect Effects 0.000 claims description 58
- 125000001424 substituent group Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 47
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 46
- 238000000034 method Methods 0.000 claims description 45
- ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical group O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 claims description 38
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 31
- 125000003342 alkenyl group Chemical group 0.000 claims description 27
- 125000000304 alkynyl group Chemical group 0.000 claims description 27
- 229920006395 saturated elastomer Polymers 0.000 claims description 26
- 239000003242 anti bacterial agent Substances 0.000 claims description 22
- 229940035893 uracil Drugs 0.000 claims description 22
- 101710183280 Topoisomerase Proteins 0.000 claims description 21
- LVWZTYCIRDMTEY-UHFFFAOYSA-N metamizole Chemical group O=C1C(N(CS(O)(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 LVWZTYCIRDMTEY-UHFFFAOYSA-N 0.000 claims description 21
- 239000008194 pharmaceutical composition Substances 0.000 claims description 21
- 208000035143 Bacterial infection Diseases 0.000 claims description 20
- 229940088710 antibiotic agent Drugs 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 18
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 14
- 230000003115 biocidal effect Effects 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 13
- 108020000946 Bacterial DNA Proteins 0.000 claims description 12
- 230000001225 therapeutic effect Effects 0.000 claims description 12
- 230000002401 inhibitory effect Effects 0.000 claims description 11
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 10
- 108020004414 DNA Proteins 0.000 claims description 9
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 9
- 229940124307 fluoroquinolone Drugs 0.000 claims description 8
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 8
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 claims description 7
- 150000004677 hydrates Chemical class 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- XQCZBXHVTFVIFE-UHFFFAOYSA-N 2-amino-4-hydroxypyrimidine Chemical group NC1=NC=CC(O)=N1 XQCZBXHVTFVIFE-UHFFFAOYSA-N 0.000 claims description 6
- 125000001054 5 membered carbocyclic group Chemical group 0.000 claims description 6
- 125000004008 6 membered carbocyclic group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 230000001093 anti-cancer Effects 0.000 claims description 4
- 230000000840 anti-viral effect Effects 0.000 claims description 4
- 125000004193 piperazinyl group Chemical group 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 239000011782 vitamin Substances 0.000 claims description 3
- 235000013343 vitamin Nutrition 0.000 claims description 3
- 229940088594 vitamin Drugs 0.000 claims description 3
- 229930003231 vitamin Natural products 0.000 claims description 3
- NNTJRXFQKMHWCH-UHFFFAOYSA-N 1-ethyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(CC)C=4C=3)F)C(=O)C=2)=C1 NNTJRXFQKMHWCH-UHFFFAOYSA-N 0.000 claims description 2
- GCNTZFIIOFTKIY-UHFFFAOYSA-N 4-hydroxypyridine Chemical group OC1=CC=NC=C1 GCNTZFIIOFTKIY-UHFFFAOYSA-N 0.000 claims description 2
- BZULXVDYDGSWKC-UHFFFAOYSA-N 8-chloro-1-ethyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=C4C(C(C(C(O)=O)=CN4CC)=O)=CC=3F)Cl)C(=O)C=2)=C1 BZULXVDYDGSWKC-UHFFFAOYSA-N 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- FNVBDZXQBKQFAQ-UHFFFAOYSA-N 1-cyclononyl-1,3-diazonane Chemical group C1CCCCCCCC1N1CNCCCCCC1 FNVBDZXQBKQFAQ-UHFFFAOYSA-N 0.000 claims 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 2
- HBBBFLGEOOJNAI-UHFFFAOYSA-N 5-cyclononyl-1,3,5-oxadiazonane Chemical group C1CCCCCCCC1N1CNCOCCCC1 HBBBFLGEOOJNAI-UHFFFAOYSA-N 0.000 claims 2
- XMINXPSYULINQV-XPLLYYSMSA-N (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-13-[(2s)-butan-2-yl]-10-(hydroxymethyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s,3s)-1-[(2-amino-2-oxoethyl)amino]-3-m Chemical compound NC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]1CCCN1C(=O)[C@H]1NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](N)CSSC1 XMINXPSYULINQV-XPLLYYSMSA-N 0.000 claims 1
- UXYMMKYCPVNQBM-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=C4C(C(C(C(O)=O)=CN4C=4C(=CC(F)=CC=4)F)=O)=CC=3F)OC)C(=O)C=2)=C1 UXYMMKYCPVNQBM-UHFFFAOYSA-N 0.000 claims 1
- RLTJVACKEUKLJE-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-[[1-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]pyrrolidin-3-yl]methylamino]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CC(CNC=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C=4C(=CC(F)=CC=4)F)F)CC3)C(=O)C=2)=C1 RLTJVACKEUKLJE-UHFFFAOYSA-N 0.000 claims 1
- BQUBBSOIYZBBOF-UHFFFAOYSA-N 1-(2,4-difluorophenyl)-7-[[1-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]pyrrolidin-3-yl]methylamino]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CC(CNC=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C=4C(=CC(F)=CC=4)F)F)CC3)C(=O)C=2)=C1 BQUBBSOIYZBBOF-UHFFFAOYSA-N 0.000 claims 1
- AAEJBCQDIPJIHN-UHFFFAOYSA-N 1-cyclooctyl-1,3-diazocane Chemical group C1CCCCCCC1N1CNCCCCC1 AAEJBCQDIPJIHN-UHFFFAOYSA-N 0.000 claims 1
- KKCOQCVPBASEDD-UHFFFAOYSA-N 1-cyclooctyl-1,4-diazocane Chemical group C1CCCCCCC1N1CCNCCCC1 KKCOQCVPBASEDD-UHFFFAOYSA-N 0.000 claims 1
- ATKRMHKKVKSKDD-UHFFFAOYSA-N 1-cyclopropyl-6-[4-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]piperazin-1-yl]-4-oxopyridine-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CCN(CC3)C=3N(C=C(C(=O)C=3)C(O)=O)C3CC3)C(=O)C=2)=C1 ATKRMHKKVKSKDD-UHFFFAOYSA-N 0.000 claims 1
- CFXOKKSZPDFENA-JOCHJYFZSA-N 1-cyclopropyl-7-[(3r)-4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]-3-methylpiperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3[C@@H](CN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(C=4C=3)C3CC3)F)C)C(=O)C=2)=C1 CFXOKKSZPDFENA-JOCHJYFZSA-N 0.000 claims 1
- BSSRCWTVYSAQCP-NRFANRHFSA-N 1-cyclopropyl-7-[(3s)-4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]-3-methylpiperazin-1-yl]-6,8-difluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3[C@H](CN(CC3)C=3C(=C4C(C(C(C(O)=O)=CN4C4CC4)=O)=CC=3F)F)C)C(=O)C=2)=C1 BSSRCWTVYSAQCP-NRFANRHFSA-N 0.000 claims 1
- YZACLCJBWPYSNU-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[2-[2-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]ethoxy]ethyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCOCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(C=4C=3)C3CC3)F)C(=O)C=2)=C1 YZACLCJBWPYSNU-UHFFFAOYSA-N 0.000 claims 1
- CMKWEZJDUBMWER-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[4-[6-(2,3-dihydro-1h-inden-5-ylamino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CCCCN4C(NC(NC=5C=C6CCCC6=CC=5)=CC4=O)=O)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 CMKWEZJDUBMWER-UHFFFAOYSA-N 0.000 claims 1
- GAZAYHFWBIBZGV-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(C=4C=3)C3CC3)F)C(=O)C=2)=C1 GAZAYHFWBIBZGV-UHFFFAOYSA-N 0.000 claims 1
- YTIBUQFDOUJDMO-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(C=4C=3)C3CC3)F)C(=O)C=2)=C1 YTIBUQFDOUJDMO-UHFFFAOYSA-N 0.000 claims 1
- TUAVKZURGLLRHQ-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=C4C(C(C(C(O)=O)=CN4C4CC4)=O)=CC=3F)OC)C(=O)C=2)=C1 TUAVKZURGLLRHQ-UHFFFAOYSA-N 0.000 claims 1
- IDHYRQSMSDNNHK-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[4-[6-[(3,4-dichlorophenyl)methylamino]-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=CC(N3CCN(CCCCN4C(NC(NCC=5C=C(Cl)C(Cl)=CC=5)=CC4=O)=O)CC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 IDHYRQSMSDNNHK-UHFFFAOYSA-N 0.000 claims 1
- FYGWDABKQRNMHR-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]piperazin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CCN(CC3)C=3C(=C4C(C(C(C(O)=O)=CN4C4CC4)=O)=CC=3F)OC)C(=O)C=2)=C1 FYGWDABKQRNMHR-UHFFFAOYSA-N 0.000 claims 1
- CTTHOSAXMLPGMG-UHFFFAOYSA-N 1-cyclopropyl-7-[4-[7-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]heptyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(C=4C=3)C3CC3)F)C(=O)C=2)=C1 CTTHOSAXMLPGMG-UHFFFAOYSA-N 0.000 claims 1
- AZLODONDCTYFJR-UHFFFAOYSA-N 1-cyclopropyl-7-[6-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]-2,3,4a,5,7,7a-hexahydropyrrolo[3,4-b][1,4]oxazin-4-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CC4N(CCOC4C3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(C=4C=3)C3CC3)F)C(=O)C=2)=C1 AZLODONDCTYFJR-UHFFFAOYSA-N 0.000 claims 1
- CJOGUVFCFDFESU-UHFFFAOYSA-N 1-cyclopropyl-7-[[1-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]pyrrolidin-3-yl]methylamino]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CC(CNC=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)CC3)C(=O)C=2)=C1 CJOGUVFCFDFESU-UHFFFAOYSA-N 0.000 claims 1
- AVPRGYSVYCJALJ-UHFFFAOYSA-N 1-ethyl-6-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-4-oxopyridine-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3N(C=C(C(=O)C=3)C(O)=O)CC)C(=O)C=2)=C1 AVPRGYSVYCJALJ-UHFFFAOYSA-N 0.000 claims 1
- CEEMTVQVNKSSHX-UHFFFAOYSA-N 1-ethyl-6-[4-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]piperazin-1-yl]-4-oxopyridine-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CCN(CC3)C=3N(C=C(C(=O)C=3)C(O)=O)CC)C(=O)C=2)=C1 CEEMTVQVNKSSHX-UHFFFAOYSA-N 0.000 claims 1
- AKXUGDTXVORMCW-UHFFFAOYSA-N 1-ethyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylic acid;hydrochloride Chemical compound Cl.C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(O)=O)=CN(CC)C=4C=3)F)C(=O)C=2)=C1 AKXUGDTXVORMCW-UHFFFAOYSA-N 0.000 claims 1
- MDURNWAMSWGJEK-UHFFFAOYSA-N 1-ethyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCN3CCN(CC3)C=3C(=C4C(C(C(C(O)=O)=CN4CC)=O)=CC=3F)OC)C(=O)C=2)=C1 MDURNWAMSWGJEK-UHFFFAOYSA-N 0.000 claims 1
- OEQDQOSPNTWRNH-UHFFFAOYSA-N 1-ethyl-7-[[1-[5-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]pentyl]pyrrolidin-3-yl]methylamino]-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCCCCN3CC(CNC=4C(=CC=5C(=O)C(C(O)=O)=CN(CC)C=5C=4)F)CC3)C(=O)C=2)=C1 OEQDQOSPNTWRNH-UHFFFAOYSA-N 0.000 claims 1
- ZUKHYOMKCHKXCK-UHFFFAOYSA-N 5-(3-ethyl-4-methylanilino)-1H-pyrimidine-2,4-dione Chemical compound C(C)C=1C=C(NC=2C(NC(NC=2)=O)=O)C=CC=1C ZUKHYOMKCHKXCK-UHFFFAOYSA-N 0.000 claims 1
- ZEEGKCFKHLONIM-UHFFFAOYSA-N 6-[4-[4-[2-amino-4-(3-ethyl-4-methylanilino)-6-oxopyrimidin-1-yl]butyl]piperazin-1-yl]-1-cyclopropyl-4-oxopyridine-3-carboxylic acid Chemical compound C1=C(C)C(CC)=CC(NC=2N=C(N)N(CCCCN3CCN(CC3)C=3N(C=C(C(=O)C=3)C(O)=O)C3CC3)C(=O)C=2)=C1 ZEEGKCFKHLONIM-UHFFFAOYSA-N 0.000 claims 1
- RICAYQWOHSLBTP-UHFFFAOYSA-N 7-[4-[4-[6-(3-chloro-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C1=C(Cl)C(C)=CC=C1NC(NC1=O)=CC(=O)N1CCCCN1CCN(C=2C(=CC=3C(=O)C(C(O)=O)=CN(C=3C=2)C2CC2)F)CC1 RICAYQWOHSLBTP-UHFFFAOYSA-N 0.000 claims 1
- 101800000805 Isotocin Proteins 0.000 claims 1
- HZEJLWYMAOTFKR-UHFFFAOYSA-N benzyl 1-cyclopropyl-7-[4-[2-[2-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]ethoxy]ethyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C1=C(C)C(CC)=CC(NC=2NC(=O)N(CCOCCN3CCN(CC3)C=3C(=CC=4C(=O)C(C(=O)OCC=5C=CC=CC=5)=CN(C=4C=3)C3CC3)F)C(=O)C=2)=C1 HZEJLWYMAOTFKR-UHFFFAOYSA-N 0.000 claims 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 claims 1
- FKKVBJQNRRLLLI-UHFFFAOYSA-N ethyl 1-cyclopropyl-7-[4-[4-[6-(3-ethyl-4-methylanilino)-2,4-dioxo-1h-pyrimidin-3-yl]butyl]piperazin-1-yl]-6-fluoro-4-oxoquinoline-3-carboxylate Chemical compound C12=CC(N3CCN(CCCCN4C(NC(NC=5C=C(CC)C(C)=CC=5)=CC4=O)=O)CC3)=C(F)C=C2C(=O)C(C(=O)OCC)=CN1C1CC1 FKKVBJQNRRLLLI-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 150000002739 metals Chemical class 0.000 claims 1
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- 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
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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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
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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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- 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
-
- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Communicable Diseases (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)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29853901P | 2001-06-15 | 2001-06-15 | |
| US34884002P | 2002-01-14 | 2002-01-14 | |
| US34981502P | 2002-01-17 | 2002-01-17 | |
| PCT/US2002/019148 WO2002102792A1 (en) | 2001-06-15 | 2002-06-17 | Novel heterocyclic antibacterial compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2004535427A JP2004535427A (ja) | 2004-11-25 |
| JP2004535427A5 JP2004535427A5 (enExample) | 2005-12-22 |
| JP4462926B2 true JP4462926B2 (ja) | 2010-05-12 |
Family
ID=27404574
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003506265A Expired - Fee Related JP4462926B2 (ja) | 2001-06-15 | 2002-06-17 | 新規な抗細菌性複素環式化合物 |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1401829B1 (enExample) |
| JP (1) | JP4462926B2 (enExample) |
| AU (1) | AU2002327182B2 (enExample) |
| CA (1) | CA2450122C (enExample) |
| ES (1) | ES2392819T3 (enExample) |
| WO (1) | WO2002102792A1 (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1472254A4 (en) * | 2002-02-08 | 2006-02-15 | Glsynthesis Inc | PURINE AND ISOSTERIC ANTIBACTERIAL COMPOUNDS |
| US7884099B2 (en) | 2007-11-16 | 2011-02-08 | Cumbre Ip Ventures, L.P. | Quinolone carboxylic acid-substituted rifamycin derivatives |
| WO2011031935A1 (en) * | 2009-09-11 | 2011-03-17 | Glsynthesis Inc. | Selective antibacterials for clostridium difficile infections |
| AR096135A1 (es) | 2013-05-02 | 2015-12-09 | Actelion Pharmaceuticals Ltd | Derivados de la quinolona |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2012681A1 (en) * | 1989-03-31 | 1990-09-30 | Masayasu Okuhira | Quinolone derivatives, preparation processes thereof, and antibacterial agents containing the same |
| CA2199645C (en) * | 1997-03-11 | 1999-06-29 | Apotex Inc. | Methods for the manufacture of quinolone carboxylic acids derivatives and intermediates thereof |
-
2002
- 2002-06-17 ES ES02763207T patent/ES2392819T3/es not_active Expired - Lifetime
- 2002-06-17 AU AU2002327182A patent/AU2002327182B2/en not_active Ceased
- 2002-06-17 WO PCT/US2002/019148 patent/WO2002102792A1/en not_active Ceased
- 2002-06-17 EP EP02763207A patent/EP1401829B1/en not_active Expired - Lifetime
- 2002-06-17 CA CA002450122A patent/CA2450122C/en not_active Expired - Fee Related
- 2002-06-17 JP JP2003506265A patent/JP4462926B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP1401829B1 (en) | 2012-08-22 |
| CA2450122C (en) | 2009-10-20 |
| ES2392819T3 (es) | 2012-12-14 |
| EP1401829A4 (en) | 2004-10-27 |
| JP2004535427A (ja) | 2004-11-25 |
| CA2450122A1 (en) | 2002-12-27 |
| EP1401829A1 (en) | 2004-03-31 |
| AU2002327182B2 (en) | 2005-09-15 |
| WO2002102792A1 (en) | 2002-12-27 |
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