EA013244B1 - 8-МЕТОКСИ-9Н-ИЗОТИАЗОЛО[5,4-b]ХИНОЛИН-3,4-ДИОНЫ И РОДСТВЕННЫЕ СОЕДИНЕНИЯ В КАЧЕСТВЕ ПРОТИВОИНФЕКЦИОННЫХ СРЕДСТВ - Google Patents

Info

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

2005-07-27

Links

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• 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
• 239000013543 active substance Substances 0.000 abstract description 15
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• 239000000969 carrier Substances 0.000 abstract description 6
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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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• 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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• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 12
• 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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• 125000000623 heterocyclic group Chemical group 0.000 description 10
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• 125000000882 C2-C6 alkenyl group Chemical group 0.000 description 9
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