EA013244B1 - 8-МЕТОКСИ-9Н-ИЗОТИАЗОЛО[5,4-b]ХИНОЛИН-3,4-ДИОНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ПРОТИВОИНФЕКЦИОННЫХ СРЕДСТВ - Google Patents
8-МЕТОКСИ-9Н-ИЗОТИАЗОЛО[5,4-b]ХИНОЛИН-3,4-ДИОНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ПРОТИВОИНФЕКЦИОННЫХ СРЕДСТВ Download PDFInfo
- Publication number
- EA013244B1 EA013244B1 EA200800444A EA200800444A EA013244B1 EA 013244 B1 EA013244 B1 EA 013244B1 EA 200800444 A EA200800444 A EA 200800444A EA 200800444 A EA200800444 A EA 200800444A EA 013244 B1 EA013244 B1 EA 013244B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- alkyl
- cyclopropyl
- dione
- fluoro
- pyrrolidin
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 265
- 239000004599 antimicrobial Substances 0.000 title description 8
- TYDQUACGVFCRFY-UHFFFAOYSA-N 8-methoxy-9h-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical class COC1=CC=CC(C2=O)=C1NC1=C2C(=O)NS1 TYDQUACGVFCRFY-UHFFFAOYSA-N 0.000 title description 4
- 229960005475 antiinfective agent Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 65
- 208000015181 infectious disease Diseases 0.000 claims abstract description 45
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 18
- 230000001580 bacterial effect Effects 0.000 claims abstract description 12
- 239000003085 diluting agent Substances 0.000 claims abstract description 12
- -1 hydroxy, amino Chemical group 0.000 claims description 208
- 125000000217 alkyl group Chemical group 0.000 claims description 172
- 125000001424 substituent group Chemical group 0.000 claims description 120
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 87
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 77
- 150000002367 halogens Chemical class 0.000 claims description 68
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 61
- 125000003118 aryl group Chemical group 0.000 claims description 59
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 54
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 53
- 125000004043 oxo group Chemical group O=* 0.000 claims description 52
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 50
- 125000005842 heteroatom Chemical group 0.000 claims description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims description 41
- 239000001257 hydrogen Substances 0.000 claims description 40
- 125000003545 alkoxy group Chemical group 0.000 claims description 39
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 34
- 125000004429 atom Chemical group 0.000 claims description 32
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 30
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 25
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 24
- 125000002619 bicyclic group Chemical group 0.000 claims description 23
- NISLPFWOZJYGOT-UHFFFAOYSA-N 9h-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound N1C2=CC=CC=C2C(=O)C2=C1SNC2=O NISLPFWOZJYGOT-UHFFFAOYSA-N 0.000 claims description 22
- 125000003282 alkyl amino group Chemical group 0.000 claims description 22
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 19
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 18
- 125000003386 piperidinyl group Chemical group 0.000 claims description 18
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004193 piperazinyl group Chemical group 0.000 claims description 17
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 16
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 14
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 12
- 125000004939 6-pyridyl group Chemical group N1=CC=CC=C1* 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 239000011737 fluorine Substances 0.000 claims description 12
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000003277 amino group Chemical group 0.000 claims description 11
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000002757 morpholinyl group Chemical group 0.000 claims description 10
- 208000035143 Bacterial infection Diseases 0.000 claims description 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 9
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 125000003003 spiro group Chemical group 0.000 claims description 8
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 7
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 239000007788 liquid Substances 0.000 claims description 7
- 239000006188 syrup Substances 0.000 claims description 7
- 235000020357 syrup Nutrition 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 239000005977 Ethylene Chemical group 0.000 claims description 6
- 239000000499 gel Substances 0.000 claims description 6
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 6
- 125000006413 ring segment Chemical group 0.000 claims description 6
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 239000007924 injection Substances 0.000 claims description 5
- 238000002347 injection Methods 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 4
- 239000006071 cream Substances 0.000 claims description 4
- 239000003826 tablet Substances 0.000 claims description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 3
- 125000003725 azepanyl group Chemical group 0.000 claims description 3
- 229940054534 ophthalmic solution Drugs 0.000 claims description 3
- 239000002997 ophthalmic solution Substances 0.000 claims description 3
- 239000006187 pill Substances 0.000 claims description 3
- 208000028172 protozoa infectious disease Diseases 0.000 claims description 3
- 125000006645 (C3-C4) cycloalkyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000005879 dioxolanyl group Chemical group 0.000 claims description 2
- VJVQHNNWFIAYBE-UHFFFAOYSA-N 1-(9-cyclopropyl-6-fluoro-8-methoxy-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)-4-methylpyrrolidine-3-carbonitrile Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C(OC)=C1N1CC(C)C(C#N)C1 VJVQHNNWFIAYBE-UHFFFAOYSA-N 0.000 claims 1
- CECJUHKZSOSOJJ-BSFGQKQYSA-N 7-[3-(2-aminopropan-2-yl)-2,2,5,5-tetradeuteriopyrrolidin-1-yl]-9-cyclopropyl-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound [2H]C1([2H])CC(C(C)(C)N)C([2H])([2H])N1C1=C(F)C=C2C(=O)C(C(=O)NS3)=C3N(C3CC3)C2=C1OC CECJUHKZSOSOJJ-BSFGQKQYSA-N 0.000 claims 1
- OXJQXSMVBYVHFL-UHFFFAOYSA-N 7-[3-(aminomethyl)azetidin-1-yl]-9-cyclopropyl-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C(OC)=C1N1CC(CN)C1 OXJQXSMVBYVHFL-UHFFFAOYSA-N 0.000 claims 1
- KNDXGEBFIJOZPT-UHFFFAOYSA-N 7-[3-(aminomethyl)pyrrolidin-1-yl]-9-cyclopropyl-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C(OC)=C1N1CCC(CN)C1 KNDXGEBFIJOZPT-UHFFFAOYSA-N 0.000 claims 1
- LRIHMVWDTGSVKD-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-piperazin-1-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C(OC)=C1N1CCNCC1 LRIHMVWDTGSVKD-UHFFFAOYSA-N 0.000 claims 1
- DOCVHCLKKONVRF-UHFFFAOYSA-N 9-cyclopropyl-7-(dimethylamino)-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(N(C)C)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 DOCVHCLKKONVRF-UHFFFAOYSA-N 0.000 claims 1
- SRZOWBIQKRHYAN-UHFFFAOYSA-N 9-cyclopropyl-7-[3-(dimethylamino)pyrrolidin-1-yl]-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C(OC)=C1N1CCC(N(C)C)C1 SRZOWBIQKRHYAN-UHFFFAOYSA-N 0.000 claims 1
- QSNLKAZJPOCZEO-UHFFFAOYSA-N 9-cyclopropyl-7-[3-(ethylamino)azetidin-1-yl]-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1C(NCC)CN1C1=C(F)C=C2C(=O)C(C(=O)NS3)=C3N(C3CC3)C2=C1OC QSNLKAZJPOCZEO-UHFFFAOYSA-N 0.000 claims 1
- SVFZLYACCDMMHP-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-(4-methylpiperazin-1-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(N2CCN(C)CC2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 SVFZLYACCDMMHP-UHFFFAOYSA-N 0.000 claims 1
- RDXLJPHGXPNKCY-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-piperazin-1-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(N2CCNCC2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 RDXLJPHGXPNKCY-UHFFFAOYSA-N 0.000 claims 1
- SDQZFTVOTNKYDA-UHFFFAOYSA-N 9-ethyl-6-fluoro-8-methoxy-7-piperazin-1-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C2N(CC)C=3SNC(=O)C=3C(=O)C2=CC(F)=C1N1CCNCC1 SDQZFTVOTNKYDA-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 83
- 230000000845 anti-microbial effect Effects 0.000 abstract description 24
- 241001465754 Metazoa Species 0.000 abstract description 19
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- 230000010076 replication Effects 0.000 abstract description 3
- 108020000946 Bacterial DNA Proteins 0.000 abstract description 2
- 229940124639 Selective inhibitor Drugs 0.000 abstract description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 101
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 74
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 68
- 238000003786 synthesis reaction Methods 0.000 description 54
- 230000015572 biosynthetic process Effects 0.000 description 50
- 239000000243 solution Substances 0.000 description 48
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
- 210000004027 cell Anatomy 0.000 description 29
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- 102000052567 Anaphase-Promoting Complex-Cyclosome Apc1 Subunit Human genes 0.000 description 27
- 108091006463 SLC25A24 Proteins 0.000 description 27
- 125000004432 carbon atom Chemical group C* 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 23
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 23
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- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
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- 244000005700 microbiome Species 0.000 description 18
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 12
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- 235000011152 sodium sulphate Nutrition 0.000 description 12
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- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 11
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- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 11
- 239000007858 starting material Substances 0.000 description 11
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- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
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- YEZNLOUZAIOMLT-UHFFFAOYSA-N tolfenamic acid Chemical compound CC1=C(Cl)C=CC=C1NC1=CC=CC=C1C(O)=O YEZNLOUZAIOMLT-UHFFFAOYSA-N 0.000 description 1
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- 229960002117 triamcinolone acetonide Drugs 0.000 description 1
- YNDXUCZADRHECN-JNQJZLCISA-N triamcinolone acetonide Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H]3OC(C)(C)O[C@@]3(C(=O)CO)[C@@]1(C)C[C@@H]2O YNDXUCZADRHECN-JNQJZLCISA-N 0.000 description 1
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- 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
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- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- FYZXEMANQYHCFX-UHFFFAOYSA-K tripotassium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxymethyl)amino]acetate Chemical compound [K+].[K+].[K+].OC(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O FYZXEMANQYHCFX-UHFFFAOYSA-K 0.000 description 1
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- 229960000832 tromantadine Drugs 0.000 description 1
- UXQDWARBDDDTKG-UHFFFAOYSA-N tromantadine Chemical compound C1C(C2)CC3CC2CC1(NC(=O)COCCN(C)C)C3 UXQDWARBDDDTKG-UHFFFAOYSA-N 0.000 description 1
- 229950002470 tropesin Drugs 0.000 description 1
- UCCJWNPWWPJKGL-UHFFFAOYSA-N tropesin Chemical compound CC1=C(CC(=O)OCC(C(O)=O)C=2C=CC=CC=2)C2=CC(OC)=CC=C2N1C(=O)C1=CC=C(Cl)C=C1 UCCJWNPWWPJKGL-UHFFFAOYSA-N 0.000 description 1
- 229950008396 ulobetasol propionate Drugs 0.000 description 1
- BDSYKGHYMJNPAB-LICBFIPMSA-N ulobetasol propionate Chemical compound C1([C@@H](F)C2)=CC(=O)C=C[C@]1(C)[C@]1(F)[C@@H]2[C@@H]2C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]2(C)C[C@@H]1O BDSYKGHYMJNPAB-LICBFIPMSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- YEIGUXGHHKAURB-VAMGGRTRSA-N viridin Chemical compound O=C1C2=C3CCC(=O)C3=CC=C2[C@@]2(C)[C@H](O)[C@H](OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-VAMGGRTRSA-N 0.000 description 1
- 108010086097 viridin Proteins 0.000 description 1
- YEIGUXGHHKAURB-UHFFFAOYSA-N viridine Natural products O=C1C2=C3CCC(=O)C3=CC=C2C2(C)C(O)C(OC)C(=O)C3=COC1=C23 YEIGUXGHHKAURB-UHFFFAOYSA-N 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 230000003313 weakening effect Effects 0.000 description 1
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- 229960003434 xenysalate Drugs 0.000 description 1
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- 229960000523 zalcitabine Drugs 0.000 description 1
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- HBOMLICNUCNMMY-XLPZGREQSA-N zidovudine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](N=[N+]=[N-])C1 HBOMLICNUCNMMY-XLPZGREQSA-N 0.000 description 1
- MWLSOWXNZPKENC-SSDOTTSWSA-N zileuton Chemical compound C1=CC=C2SC([C@H](N(O)C(N)=O)C)=CC2=C1 MWLSOWXNZPKENC-SSDOTTSWSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—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
- A61K31/33—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
- A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4365—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system having sulfur as a ring hetero atom, e.g. ticlopidine
-
- 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
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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
-
- 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
- A61P31/12—Antivirals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—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
-
- 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
- C07D513/12—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 three hetero rings
- C07D513/14—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Medicinal Preparation (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US70281105P | 2005-07-27 | 2005-07-27 | |
| PCT/US2006/029302 WO2007014308A1 (en) | 2005-07-27 | 2006-07-27 | 8-methoxy-9h-isothiazolo[5,4-b]quinoline-3,4-diones and related compounds as anti-infective agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA200800444A1 EA200800444A1 (ru) | 2008-06-30 |
| EA013244B1 true EA013244B1 (ru) | 2010-04-30 |
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| EA200800444A EA013244B1 (ru) | 2005-07-27 | 2006-07-27 | 8-МЕТОКСИ-9Н-ИЗОТИАЗОЛО[5,4-b]ХИНОЛИН-3,4-ДИОНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ПРОТИВОИНФЕКЦИОННЫХ СРЕДСТВ |
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| EP (1) | EP1913004B1 (OSRAM) |
| JP (1) | JP5143000B2 (OSRAM) |
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| CN (1) | CN101263146B (OSRAM) |
| AT (1) | ATE482219T1 (OSRAM) |
| AU (1) | AU2006272571B2 (OSRAM) |
| BR (1) | BRPI0614456B8 (OSRAM) |
| CA (1) | CA2616768C (OSRAM) |
| DE (1) | DE602006017082D1 (OSRAM) |
| DK (1) | DK1913004T3 (OSRAM) |
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| ES (1) | ES2352799T3 (OSRAM) |
| IL (1) | IL189017A (OSRAM) |
| NO (1) | NO343376B1 (OSRAM) |
| NZ (1) | NZ566209A (OSRAM) |
| PL (1) | PL1913004T3 (OSRAM) |
| PT (1) | PT1913004E (OSRAM) |
| WO (1) | WO2007014308A1 (OSRAM) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2008021491A2 (en) * | 2006-08-16 | 2008-02-21 | Achillion Pharmaceuticals, Inc. | Method for synthesis of 8-alkoxy-9h-isothiazolo[5,4-b]quinoline-3,4-diones |
| WO2010115184A2 (en) * | 2009-04-03 | 2010-10-07 | Achillion Pharmaceuticals, Inc. | Hydroxythienoquinolones and related compounds as anti-infective agents |
| WO2011031745A1 (en) | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| BR112012008759A2 (pt) | 2009-10-16 | 2020-08-25 | Rib-X Pharmaceuticals, Inc. | compostos antimicrobianos e métodos de fabricação e uso dos mesmos |
| WO2011047323A2 (en) | 2009-10-16 | 2011-04-21 | Rib-X Pharmaceuticals, Inc. | Antimicrobial compounds and methods of making and using the same |
| CN105646370A (zh) * | 2009-10-16 | 2016-06-08 | 梅琳塔治疗公司 | 抗微生物化合物和其制备和使用方法 |
| TN2010000566A1 (en) * | 2010-12-03 | 2012-05-24 | Rekik Raouf | Folic acid - ramipril combination : cell protective neuroprotective and retinoprotective ophtalmologic drugs |
| CN103819401B (zh) * | 2012-11-19 | 2016-04-13 | 浙江中欣氟材股份有限公司 | 1-环丙基-4-氧代-7-氟-8-甲氧基-1,4-二氢喹啉-3-羧酸的合成方法 |
| EP3039025A4 (en) | 2013-09-09 | 2017-05-31 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| MX2016003046A (es) | 2013-09-09 | 2016-09-08 | Melinta Therapeutics Inc | Compuestos antimicrobianos y métodos de fabricación y utilización de los mismos. |
| WO2015114317A1 (en) * | 2014-01-28 | 2015-08-06 | Redx Pharma Plc | 5h-isothiazolo[4,5-c]pyridine-3,4-dione or 5h-pyrazolo[4,3-c]pyridin-3,4-dione as antibacterial compounds |
| CN107922418A (zh) | 2015-03-11 | 2018-04-17 | 梅琳塔治疗公司 | 抗微生物化合物及制备和使用所述化合物的方法 |
| JP2019515041A (ja) | 2016-05-06 | 2019-06-06 | メリンタ セラピューティクス、 インコーポレイテッドＭｅｌｉｎｔａ Ｔｈｅｒａｐｅｕｔｉｃｓ， Ｉｎｃ． | 抗菌剤ならびにそれを作製および使用する方法 |
| EP4483875A3 (en) | 2016-05-10 | 2025-04-02 | C4 Therapeutics, Inc. | Spirocyclic degronimers for target protein degradation |
| CN109562107A (zh) | 2016-05-10 | 2019-04-02 | C4医药公司 | 用于靶蛋白降解的杂环降解决定子体 |
| EP3455219A4 (en) | 2016-05-10 | 2019-12-18 | C4 Therapeutics, Inc. | AMINE-RELATED C3-GLUTARIMIDE DEGRONIMERS FOR TARGET PROTEIN REDUCTION |
| CN109641874A (zh) | 2016-05-10 | 2019-04-16 | C4医药公司 | 用于靶蛋白降解的c3-碳连接的戊二酰亚胺降解决定子体 |
| EP3641762B1 (en) | 2017-06-20 | 2026-02-18 | C4 Therapeutics, Inc. | N/o-linked degrons and degronimers for protein degradation |
| KR102534570B1 (ko) * | 2019-02-01 | 2023-05-18 | 에어리 파마슈티컬즈, 인코포레이티드 | 근시의 치료를 위한 화합물, 조성물 및 방법 |
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| WO1995029894A1 (en) * | 1994-04-28 | 1995-11-09 | The Procter & Gamble Company | Novel quinolone 5-(n-heterosubstituted amino) antimicrobials |
| WO2002048138A1 (en) * | 2000-12-14 | 2002-06-20 | The Procter & Gamble Company | Antimicrobial quinolones |
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| US4767762A (en) | 1985-12-23 | 1988-08-30 | Abbott Laboratories | Tricyclic quinoline and naphthyride antibacterials |
| JPH01160985A (ja) | 1987-12-17 | 1989-06-23 | Otsuka Pharmaceut Co Ltd | ベンゾヘテロ環化合物 |
| JPH01193275A (ja) | 1988-01-28 | 1989-08-03 | Otsuka Pharmaceut Co Ltd | ベンゾヘテロ環化合物 |
| JP2681190B2 (ja) | 1988-04-13 | 1997-11-26 | 塩野義製薬株式会社 | ピリドン系抗菌剤 |
| CA2001203C (en) | 1988-10-24 | 2001-02-13 | Thomas P. Demuth, Jr. | Novel antimicrobial dithiocarbamoyl quinolones |
| US5328908A (en) | 1988-10-24 | 1994-07-12 | Procter & Gamble Pharmaceuticals, Inc. | Antimicrobial quinolone thioureas |
| JPH02174784A (ja) | 1988-12-27 | 1990-07-06 | Hokuriku Seiyaku Co Ltd | イソチアゾロキノリン誘導体 |
| JPH02243692A (ja) | 1989-03-16 | 1990-09-27 | Dainippon Pharmaceut Co Ltd | 三環式化合物 |
| JPH02255687A (ja) | 1989-03-27 | 1990-10-16 | Dainippon Pharmaceut Co Ltd | 三環式化合物 |
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| US5071848A (en) | 1989-10-23 | 1991-12-10 | Abbott Laboratories | Tricyclic quinoline antineoplastic agents |
| JP2939280B2 (ja) | 1990-01-10 | 1999-08-25 | 三共株式会社 | フッ素置換メトキシキノロンカルボン酸誘導体 |
| US5580872A (en) | 1990-05-02 | 1996-12-03 | Abbott Laboratories | Quinolizinone type compounds |
| NO304832B1 (no) | 1992-05-27 | 1999-02-22 | Ube Industries | Aminokinolonderivater samt middel mot HIV |
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| JP3616454B2 (ja) | 1996-04-19 | 2005-02-02 | 栄研化学株式会社 | 生体成分測定用試薬 |
| JPH10130149A (ja) | 1996-07-12 | 1998-05-19 | Sankyo Co Ltd | Ｔｎｆ産生抑制剤 |
| DE19652219A1 (de) | 1996-12-16 | 1998-06-18 | Bayer Ag | Verwendung von 7-(1-Aminomethyl-2-oxa-7-azabicyclo[3.3.0]oct-7-yl)-chinolon- und naphthyridoncarbonsäure-Derivaten zur Therapie von Helicobacter-pylori-Infektionen und den damit assoziierten gastroduodenalen Erkrankungen |
| AU2004267052B2 (en) * | 2003-08-12 | 2009-02-05 | Achillion Pharmaceuticals, Inc. | Isothiazoloquinolones and related compounds as anti-infective agents |
| ATE445623T1 (de) * | 2004-11-11 | 2009-10-15 | Achillion Pharmaceuticals Inc | 8a, 9-dihydro-4a-h-isothiazoloä5,4-bü chinolin-3, 4-dione und verwandte verbindungen als infektionsschutzmittel |
| EP1848723B1 (en) * | 2005-02-16 | 2010-12-15 | Achillion Pharmaceuticals, Inc. | New isothiazoloquinolones and related compounds as anti-infective agents |
| WO2010115184A2 (en) | 2009-04-03 | 2010-10-07 | Achillion Pharmaceuticals, Inc. | Hydroxythienoquinolones and related compounds as anti-infective agents |
-
2006
- 2006-07-27 CN CN200680033548XA patent/CN101263146B/zh active Active
- 2006-07-27 ES ES06800428T patent/ES2352799T3/es active Active
- 2006-07-27 JP JP2008524168A patent/JP5143000B2/ja not_active Expired - Fee Related
- 2006-07-27 EP EP06800428A patent/EP1913004B1/en active Active
- 2006-07-27 BR BRPI0614456A patent/BRPI0614456B8/pt active IP Right Grant
- 2006-07-27 DE DE602006017082T patent/DE602006017082D1/de active Active
- 2006-07-27 AT AT06800428T patent/ATE482219T1/de active
- 2006-07-27 DK DK06800428.2T patent/DK1913004T3/da active
- 2006-07-27 KR KR1020087004769A patent/KR101272263B1/ko active Active
- 2006-07-27 CA CA2616768A patent/CA2616768C/en not_active Expired - Fee Related
- 2006-07-27 EA EA200800444A patent/EA013244B1/ru unknown
- 2006-07-27 US US11/494,205 patent/US8044204B2/en active Active
- 2006-07-27 PT PT06800428T patent/PT1913004E/pt unknown
- 2006-07-27 AU AU2006272571A patent/AU2006272571B2/en not_active Ceased
- 2006-07-27 PL PL06800428T patent/PL1913004T3/pl unknown
- 2006-07-27 NZ NZ566209A patent/NZ566209A/en unknown
- 2006-07-27 WO PCT/US2006/029302 patent/WO2007014308A1/en not_active Ceased
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2008
- 2008-01-24 IL IL189017A patent/IL189017A/en active IP Right Grant
- 2008-02-27 NO NO20081005A patent/NO343376B1/no unknown
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2011
- 2011-10-24 US US13/279,852 patent/US8946422B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1995029894A1 (en) * | 1994-04-28 | 1995-11-09 | The Procter & Gamble Company | Novel quinolone 5-(n-heterosubstituted amino) antimicrobials |
| WO2002048138A1 (en) * | 2000-12-14 | 2002-06-20 | The Procter & Gamble Company | Antimicrobial quinolones |
Also Published As
| Publication number | Publication date |
|---|---|
| PT1913004E (pt) | 2010-12-09 |
| EA200800444A1 (ru) | 2008-06-30 |
| AU2006272571B2 (en) | 2012-03-08 |
| BRPI0614456B8 (pt) | 2021-05-25 |
| PL1913004T3 (pl) | 2011-03-31 |
| WO2007014308A1 (en) | 2007-02-01 |
| US20120040959A1 (en) | 2012-02-16 |
| NO343376B1 (no) | 2019-02-11 |
| US20070049586A1 (en) | 2007-03-01 |
| AU2006272571A1 (en) | 2007-02-01 |
| CA2616768C (en) | 2014-05-06 |
| IL189017A (en) | 2014-01-30 |
| DE602006017082D1 (de) | 2010-11-04 |
| HK1122024A1 (en) | 2009-05-08 |
| CA2616768A1 (en) | 2007-02-01 |
| JP5143000B2 (ja) | 2013-02-13 |
| BRPI0614456B1 (pt) | 2019-08-27 |
| ATE482219T1 (de) | 2010-10-15 |
| NZ566209A (en) | 2011-03-31 |
| EP1913004A1 (en) | 2008-04-23 |
| KR101272263B1 (ko) | 2013-06-13 |
| KR20080035661A (ko) | 2008-04-23 |
| IL189017A0 (en) | 2008-08-07 |
| BRPI0614456A2 (pt) | 2011-03-29 |
| JP2009502953A (ja) | 2009-01-29 |
| DK1913004T3 (da) | 2011-01-10 |
| US8044204B2 (en) | 2011-10-25 |
| CN101263146A (zh) | 2008-09-10 |
| EP1913004B1 (en) | 2010-09-22 |
| US8946422B2 (en) | 2015-02-03 |
| CN101263146B (zh) | 2012-12-05 |
| NO20081005L (no) | 2008-04-09 |
| ES2352799T3 (es) | 2011-02-23 |
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