JP5147237B2 - 抗感染剤としてのイソチアゾロキノロン類および関連化合物 - Google Patents

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Publication number

JP5147237B2

JP5147237B2 JP2006523236A JP2006523236A JP5147237B2 JP 5147237 B2 JP5147237 B2 JP 5147237B2 JP 2006523236 A JP2006523236 A JP 2006523236A JP 2006523236 A JP2006523236 A JP 2006523236A JP 5147237 B2 JP5147237 B2 JP 5147237B2

Authority

JP

Japan

Prior art keywords

cyclopropyl

alkyl

fluoro

quinoline

isothiazolo

Prior art date

2003-08-12

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.)

Expired - Fee Related

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• 150000001875 compounds Chemical class 0.000 title claims description 273
• QXHKKCITURTUFC-UHFFFAOYSA-N [1,2]thiazolo[3,4-h]quinoline 8-oxide Chemical class C1=CN=C2C3=CS(=O)N=C3C=CC2=C1 QXHKKCITURTUFC-UHFFFAOYSA-N 0.000 title description 4
• 230000002924 anti-infective effect Effects 0.000 title 1
• 229960005475 antiinfective agent Drugs 0.000 title 1
• 125000000217 alkyl group Chemical group 0.000 claims description 296
• -1 hydroxy, amino Chemical group 0.000 claims description 207
• 150000003839 salts Chemical class 0.000 claims description 106
• 239000000203 mixture Substances 0.000 claims description 100
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 82
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 78
• 239000000243 solution Substances 0.000 claims description 78
• 125000001424 substituent group Chemical group 0.000 claims description 78
• 125000003118 aryl group Chemical group 0.000 claims description 64
• 229910052736 halogen Inorganic materials 0.000 claims description 60
• 150000002367 halogens Chemical class 0.000 claims description 56
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 55
• 125000001188 haloalkyl group Chemical group 0.000 claims description 54
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 52
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 52
• 125000003282 alkyl amino group Chemical group 0.000 claims description 51
• 125000003545 alkoxy group Chemical group 0.000 claims description 49
• 125000004076 pyridyl group Chemical group 0.000 claims description 44
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 37
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 34
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 31
• 125000001544 thienyl group Chemical group 0.000 claims description 31
• 208000015181 infectious disease Diseases 0.000 claims description 30
• 229910052799 carbon Inorganic materials 0.000 claims description 28
• 125000003386 piperidinyl group Chemical group 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 26
• 125000004432 carbon atom Chemical group C* 0.000 claims description 26
• 238000004519 manufacturing process Methods 0.000 claims description 26
• 230000000813 microbial effect Effects 0.000 claims description 25
• 125000004193 piperazinyl group Chemical group 0.000 claims description 24
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 23
• 125000002541 furyl group Chemical group 0.000 claims description 23
• 229910052757 nitrogen Inorganic materials 0.000 claims description 23
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 23
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 23
• 125000001624 naphthyl group Chemical group 0.000 claims description 22
• 229910052739 hydrogen Inorganic materials 0.000 claims description 21
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 21
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 21
• 125000002883 imidazolyl group Chemical group 0.000 claims description 20
• 125000002757 morpholinyl group Chemical group 0.000 claims description 20
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 20
• 239000001257 hydrogen Substances 0.000 claims description 19
• 239000008194 pharmaceutical composition Substances 0.000 claims description 19
• 125000001072 heteroaryl group Chemical group 0.000 claims description 18
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 18
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
• 125000001041 indolyl group Chemical group 0.000 claims description 17
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 17
• 125000004043 oxo group Chemical group O=* 0.000 claims description 17
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 16
• 241001465754 Metazoa Species 0.000 claims description 15
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 15
• 239000003242 anti bacterial agent Substances 0.000 claims description 13
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 13
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 10
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 10
• 150000002431 hydrogen Chemical class 0.000 claims description 10
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
• 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 9
• 239000003937 drug carrier Substances 0.000 claims description 9
• 239000000499 gel Substances 0.000 claims description 9
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 9
• 239000003826 tablet Substances 0.000 claims description 9
• 208000035143 Bacterial infection Diseases 0.000 claims description 8
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
• 229940121375 antifungal agent Drugs 0.000 claims description 8
• 208000022362 bacterial infectious disease Diseases 0.000 claims description 8
• 239000003085 diluting agent Substances 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 8
• 239000006188 syrup Substances 0.000 claims description 8
• 235000020357 syrup Nutrition 0.000 claims description 8
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 7
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 7
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 239000006071 cream Substances 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
• 239000003429 antifungal agent Substances 0.000 claims description 6
• 239000003781 beta lactamase inhibitor Substances 0.000 claims description 6
• 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 6
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 5
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 5
• 239000003443 antiviral agent Substances 0.000 claims description 5
• 239000002775 capsule Substances 0.000 claims description 5
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 102000014150 Interferons Human genes 0.000 claims description 4
• 108010050904 Interferons Proteins 0.000 claims description 4
• 239000003904 antiprotozoal agent Substances 0.000 claims description 4
• 239000000443 aerosol Substances 0.000 claims description 3
• 239000007924 injection Substances 0.000 claims description 3
• 238000002347 injection Methods 0.000 claims description 3
• 229940047124 interferons Drugs 0.000 claims description 3
• 239000002997 ophthalmic solution Substances 0.000 claims description 3
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
• 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
• 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
• 125000004531 indol-5-yl group Chemical group [H]N1C([H])=C([H])C2=C([H])C(*)=C([H])C([H])=C12 0.000 claims description 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
• 229940054534 ophthalmic solution Drugs 0.000 claims description 2
• 239000006187 pill Substances 0.000 claims description 2
• 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 2
• 125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims description 2
• 125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims description 2
• XOQKPULBJQSJFY-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methylpyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=NC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 XOQKPULBJQSJFY-UHFFFAOYSA-N 0.000 claims 2
• CRIYBBNVSFMWAI-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-[4-(2-piperazin-1-ylethoxy)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(OCCN3CCNCC3)=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 CRIYBBNVSFMWAI-UHFFFAOYSA-N 0.000 claims 2
• YWKPGUNDQNCPFW-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-[4-(morpholin-4-ylmethyl)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(CN3CCOCC3)=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 YWKPGUNDQNCPFW-UHFFFAOYSA-N 0.000 claims 2
• UYPSDUSCAAQITG-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-quinolin-6-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C3C=CC=NC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 UYPSDUSCAAQITG-UHFFFAOYSA-N 0.000 claims 2
• KHRKFJDERXWJPK-UHFFFAOYSA-N 9-cyclopropyl-7-[3-(3,4-dihydro-2h-pyrrol-5-yl)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CC=CC=1C1=NCCC1 KHRKFJDERXWJPK-UHFFFAOYSA-N 0.000 claims 2
• ZZKYLKASKFDFIK-UHFFFAOYSA-N 2-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzaldehyde Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CC=C1C=O ZZKYLKASKFDFIK-UHFFFAOYSA-N 0.000 claims 1
• TXIKZINABYEDRP-UHFFFAOYSA-N 2-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzonitrile Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CC=C1C#N TXIKZINABYEDRP-UHFFFAOYSA-N 0.000 claims 1
• VKPUHQOMXQBHAU-UHFFFAOYSA-N 2-(butylamino)-n-[4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)CNCCCC)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 VKPUHQOMXQBHAU-UHFFFAOYSA-N 0.000 claims 1
• DQONWIJRCZUCJY-UHFFFAOYSA-N 2-[4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]acetonitrile Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=C(CC#N)C=C1 DQONWIJRCZUCJY-UHFFFAOYSA-N 0.000 claims 1
• GFZCDTJEQCRCPK-UHFFFAOYSA-N 2-[4-(9-cyclopropyl-8-methoxy-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]acetonitrile Chemical compound COC1=C(C=2C=CC(CC#N)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 GFZCDTJEQCRCPK-UHFFFAOYSA-N 0.000 claims 1
• UCPGRNRCERUMJB-UHFFFAOYSA-N 2-amino-n-[4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]acetamide Chemical compound C1=CC(NC(=O)CN)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 UCPGRNRCERUMJB-UHFFFAOYSA-N 0.000 claims 1
• MPZFBKMYODUUMA-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)-4-fluorobenzonitrile Chemical compound FC1=CC=C(C#N)C=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 MPZFBKMYODUUMA-UHFFFAOYSA-N 0.000 claims 1
• SKEUBXQVSOIZFD-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzaldehyde Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CC(C=O)=C1 SKEUBXQVSOIZFD-UHFFFAOYSA-N 0.000 claims 1
• KWSRANFQBPECDZ-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 KWSRANFQBPECDZ-UHFFFAOYSA-N 0.000 claims 1
• GLTRXSIQLMYMDI-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzonitrile Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CC(C#N)=C1 GLTRXSIQLMYMDI-UHFFFAOYSA-N 0.000 claims 1
• PDDPQJYFVLQNNZ-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)thiophene-2-carbaldehyde Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C=1C=CSC=1C=O PDDPQJYFVLQNNZ-UHFFFAOYSA-N 0.000 claims 1
• JCJDDCSISLGXQE-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-8-methoxy-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzonitrile Chemical compound COC1=C(C=2C=C(C=CC=2)C#N)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 JCJDDCSISLGXQE-UHFFFAOYSA-N 0.000 claims 1
• ADHVHOJEMSWKDK-UHFFFAOYSA-N 3-(9-cyclopropyl-8-methoxy-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzonitrile Chemical compound COC1=C(C=2C=C(C=CC=2)C#N)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ADHVHOJEMSWKDK-UHFFFAOYSA-N 0.000 claims 1
• CZDBJUNAGXZNCT-UHFFFAOYSA-N 3-amino-n-[4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]propanamide Chemical compound C1=CC(NC(=O)CCN)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 CZDBJUNAGXZNCT-UHFFFAOYSA-N 0.000 claims 1
• FKLMUBAFGRSSAD-UHFFFAOYSA-N 4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzaldehyde Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=C(C=O)C=C1 FKLMUBAFGRSSAD-UHFFFAOYSA-N 0.000 claims 1
• OPEQHLNWRIRUFX-UHFFFAOYSA-N 4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzonitrile Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=C(C#N)C=C1 OPEQHLNWRIRUFX-UHFFFAOYSA-N 0.000 claims 1
• COTHAJIFCSYEGY-UHFFFAOYSA-N 5-cyclopenta[b]pyran-2-yl-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=2SNC(=O)C=2C(=O)C2=C(C=3OC4=CC=CC4=CC=3)C(F)=CC=C2N1C1CC1 COTHAJIFCSYEGY-UHFFFAOYSA-N 0.000 claims 1
• LHAGFWHQNNTTJM-UHFFFAOYSA-N 7-(1,3-benzodioxol-5-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3OCOC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 LHAGFWHQNNTTJM-UHFFFAOYSA-N 0.000 claims 1
• MNYBJBXJSSLQKB-UHFFFAOYSA-N 7-(1-benzothiophen-2-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2SC3=CC=CC=C3C=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 MNYBJBXJSSLQKB-UHFFFAOYSA-N 0.000 claims 1
• MXTCSLANVSRZAY-UHFFFAOYSA-N 7-(1-benzylpyrazol-4-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(=C1)C=NN1CC1=CC=CC=C1 MXTCSLANVSRZAY-UHFFFAOYSA-N 0.000 claims 1
• NMDLMCNOMSXERQ-UHFFFAOYSA-N 7-(2-aminophenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound NC1=CC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 NMDLMCNOMSXERQ-UHFFFAOYSA-N 0.000 claims 1
• XIYZKIOYISMEAI-UHFFFAOYSA-N 7-(2-chloropyridin-3-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CN=C1Cl XIYZKIOYISMEAI-UHFFFAOYSA-N 0.000 claims 1
• HIMNMEMZWHWBRO-UHFFFAOYSA-N 7-(3-acetylphenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC(=O)C1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 HIMNMEMZWHWBRO-UHFFFAOYSA-N 0.000 claims 1
• ZGAFFFIUJOOABG-UHFFFAOYSA-N 7-(3-amino-4-fluorophenyl)-9-cyclopropyl-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(N)C(F)=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ZGAFFFIUJOOABG-UHFFFAOYSA-N 0.000 claims 1
• HFRGSVIKEOBJHY-UHFFFAOYSA-N 7-(3-amino-4-fluorophenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(F)C(N)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 HFRGSVIKEOBJHY-UHFFFAOYSA-N 0.000 claims 1
• DVBCSVHTGNDKIW-UHFFFAOYSA-N 7-(3-amino-4-methylphenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(N)C(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 DVBCSVHTGNDKIW-UHFFFAOYSA-N 0.000 claims 1
• KKUHZTLGKWLPKE-UHFFFAOYSA-N 7-(3-aminophenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound NC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 KKUHZTLGKWLPKE-UHFFFAOYSA-N 0.000 claims 1
• BDAVOIPATTWXOJ-UHFFFAOYSA-N 7-(3-chloropyridin-4-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=NC=C1Cl BDAVOIPATTWXOJ-UHFFFAOYSA-N 0.000 claims 1
• JYDZVUWVVASPRQ-UHFFFAOYSA-N 7-(4-aminophenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(N)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 JYDZVUWVVASPRQ-UHFFFAOYSA-N 0.000 claims 1
• VUZSTEBQFPSZPC-UHFFFAOYSA-N 7-(4-tert-butylphenyl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(C(C)(C)C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 VUZSTEBQFPSZPC-UHFFFAOYSA-N 0.000 claims 1
• ANWXHTCCTWKIPJ-UHFFFAOYSA-N 7-[1-(benzenesulfonyl)indol-3-yl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C1=CC=CC=C11)=CN1S(=O)(=O)C1=CC=CC=C1 ANWXHTCCTWKIPJ-UHFFFAOYSA-N 0.000 claims 1
• FXVJVTDGWQCYOQ-UHFFFAOYSA-N 7-[3-(aminomethyl)phenyl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound NCC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 FXVJVTDGWQCYOQ-UHFFFAOYSA-N 0.000 claims 1
• BZOIHLQZHMUKDR-UHFFFAOYSA-N 7-[4-(2-amino-3-hydroxypropyl)phenyl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(CC(CO)N)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 BZOIHLQZHMUKDR-UHFFFAOYSA-N 0.000 claims 1
• VJCSLYVMJRFIBU-UHFFFAOYSA-N 7-[4-(2-aminoethyl)phenyl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(CCN)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 VJCSLYVMJRFIBU-UHFFFAOYSA-N 0.000 claims 1
• DJCSYPYZUIMLAD-UHFFFAOYSA-N 7-[4-(aminomethyl)phenyl]-9-cyclopropyl-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=CC(CN)=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 DJCSYPYZUIMLAD-UHFFFAOYSA-N 0.000 claims 1
• JRMYGOQEFDLQJN-UHFFFAOYSA-N 7-[4-(aminomethyl)phenyl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(CN)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 JRMYGOQEFDLQJN-UHFFFAOYSA-N 0.000 claims 1
• YSYWTSGTIIQDBD-UHFFFAOYSA-N 7-[4-(aminomethyl)phenyl]-9-cyclopropyl-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(CN)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 YSYWTSGTIIQDBD-UHFFFAOYSA-N 0.000 claims 1
• YFKOZLSAJAURNR-UHFFFAOYSA-N 7-[4-(azepan-2-yl)phenyl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=C1)=CC=C1C1CCCCCN1 YFKOZLSAJAURNR-UHFFFAOYSA-N 0.000 claims 1
• CKPRQGFZVOFSRT-UHFFFAOYSA-N 7-[6-(aminomethyl)pyridin-3-yl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.C1=NC(CN)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 CKPRQGFZVOFSRT-UHFFFAOYSA-N 0.000 claims 1
• UDIXIZGXKVFDEO-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1,2,3,4-tetrahydroisoquinolin-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=3CCNCC=3C=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 UDIXIZGXKVFDEO-UHFFFAOYSA-N 0.000 claims 1
• WLUGSWYWAKTACB-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1,2,3,4-tetrahydroisoquinolin-6-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3CCNCC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 WLUGSWYWAKTACB-UHFFFAOYSA-N 0.000 claims 1
• ZWNZZUPTEQZPFP-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1,2,3,4-tetrahydroquinolin-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=3CCCNC=3C=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ZWNZZUPTEQZPFP-UHFFFAOYSA-N 0.000 claims 1
• WYJAPBZSMDRTRA-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1,2,3,4-tetrahydroquinolin-6-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3CCCNC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 WYJAPBZSMDRTRA-UHFFFAOYSA-N 0.000 claims 1
• DRYAFOTZRQGSAV-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1,3-thiazol-2-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=NC=CS1 DRYAFOTZRQGSAV-UHFFFAOYSA-N 0.000 claims 1
• JLIBGEGQMRREEI-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1-methyl-2,3-dihydro-1h-isoindol-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C=1C=C2C(C)NCC2=CC=1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 JLIBGEGQMRREEI-UHFFFAOYSA-N 0.000 claims 1
• WCHBHALZTXKDGC-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1-methylindol-6-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C2N(C)C=CC2=CC=C1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 WCHBHALZTXKDGC-UHFFFAOYSA-N 0.000 claims 1
• OPJNSXZCMYVJIF-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1h-indol-2-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2NC3=CC=CC=C3C=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 OPJNSXZCMYVJIF-UHFFFAOYSA-N 0.000 claims 1
• KIIHYLQTRPZXOO-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1h-indol-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3C=CNC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 KIIHYLQTRPZXOO-UHFFFAOYSA-N 0.000 claims 1
• FKWGLPTZAGIYTG-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1h-pyrrol-2-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CN1 FKWGLPTZAGIYTG-UHFFFAOYSA-N 0.000 claims 1
• ZMARNIFJCUSNEH-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2,4,6-trimethylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC(C)=CC(C)=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 ZMARNIFJCUSNEH-UHFFFAOYSA-N 0.000 claims 1
• CNPWWMOSTVQKGJ-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-fluorophenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 CNPWWMOSTVQKGJ-UHFFFAOYSA-N 0.000 claims 1
• BGWYQEFQCMRJGY-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-fluoropyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CN=C1F BGWYQEFQCMRJGY-UHFFFAOYSA-N 0.000 claims 1
• IDXNHRNHCGDEQR-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-fluoropyridin-4-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=NC(F)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 IDXNHRNHCGDEQR-UHFFFAOYSA-N 0.000 claims 1
• RADYVVZAZJQFAM-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methoxy-4-methylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 RADYVVZAZJQFAM-UHFFFAOYSA-N 0.000 claims 1
• NUBPDNKPJYPGII-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methoxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 NUBPDNKPJYPGII-UHFFFAOYSA-N 0.000 claims 1
• DAUKXNUSOVHBHB-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methoxypyrimidin-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=NC(OC)=NC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 DAUKXNUSOVHBHB-UHFFFAOYSA-N 0.000 claims 1
• JPUSEYDWDIYGGK-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methyl-1,3-dihydroisoindol-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C2CN(C)CC2=CC=C1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 JPUSEYDWDIYGGK-UHFFFAOYSA-N 0.000 claims 1
• DUTFCORAPQTKIR-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methyl-3,4-dihydro-1h-isoquinolin-6-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C=1C=C2CN(C)CCC2=CC=1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 DUTFCORAPQTKIR-UHFFFAOYSA-N 0.000 claims 1
• ZCANEJVVXSAHJC-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-methylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 ZCANEJVVXSAHJC-UHFFFAOYSA-N 0.000 claims 1
• AYIHESPYYZYLOH-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-morpholin-4-ylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CC=C1N1CCOCC1 AYIHESPYYZYLOH-UHFFFAOYSA-N 0.000 claims 1
• UWJQBRJDIKCCNU-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-morpholin-4-ylpyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=CN=C1N1CCOCC1 UWJQBRJDIKCCNU-UHFFFAOYSA-N 0.000 claims 1
• IYHMYPKBQIROEL-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-fluoro-4-methylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(F)C(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 IYHMYPKBQIROEL-UHFFFAOYSA-N 0.000 claims 1
• RYGQUNHPYQJBTQ-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-fluorophenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 RYGQUNHPYQJBTQ-UHFFFAOYSA-N 0.000 claims 1
• RFAPGAPICNQXOM-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-hydroxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound OC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 RFAPGAPICNQXOM-UHFFFAOYSA-N 0.000 claims 1
• ZJZVYCLADXEMHX-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-methoxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 ZJZVYCLADXEMHX-UHFFFAOYSA-N 0.000 claims 1
• VJVUQNJYHIPOII-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-phenylmethoxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CC=CC=1OCC1=CC=CC=C1 VJVUQNJYHIPOII-UHFFFAOYSA-N 0.000 claims 1
• QBQMFPAESUGUTF-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-piperidin-1-ylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CC=CC=1N1CCCCC1 QBQMFPAESUGUTF-UHFFFAOYSA-N 0.000 claims 1
• PKSRQRFDRMZEJO-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-piperidin-2-ylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CC=CC=1C1CCCCN1 PKSRQRFDRMZEJO-UHFFFAOYSA-N 0.000 claims 1
• SOVROYBDNVSMII-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-propan-2-yloxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC(C)OC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 SOVROYBDNVSMII-UHFFFAOYSA-N 0.000 claims 1
• NCSHIYBJAPNXPI-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-pyrrol-1-ylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CC=CC=1N1C=CC=C1 NCSHIYBJAPNXPI-UHFFFAOYSA-N 0.000 claims 1
• NZYDOGZZQXTVLE-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-pyrrolidin-1-ylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CC=CC=1N1CCCC1 NZYDOGZZQXTVLE-UHFFFAOYSA-N 0.000 claims 1
• JAWPNZIFCXTZDM-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-fluorophenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(F)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 JAWPNZIFCXTZDM-UHFFFAOYSA-N 0.000 claims 1
• WWHQGHPOTUSHCB-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-hydroxy-3,5-dimethylphenyl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(C)C(O)=C(C)C=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 WWHQGHPOTUSHCB-UHFFFAOYSA-N 0.000 claims 1
• FMFZDRXHROLOID-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-hydroxy-3,5-dimethylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=C(O)C(C)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 FMFZDRXHROLOID-UHFFFAOYSA-N 0.000 claims 1
• HEACTVVOHWSEHT-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-hydroxy-3-methoxyphenyl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(O)C(OC)=CC(C=2C(=C3C(C(C=4C(=O)NSC=4N3C3CC3)=O)=CC=2F)OC)=C1 HEACTVVOHWSEHT-UHFFFAOYSA-N 0.000 claims 1
• WOXYBNZJQAVVKV-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-hydroxy-3-methoxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(O)C(OC)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 WOXYBNZJQAVVKV-UHFFFAOYSA-N 0.000 claims 1
• ZKTJDFKFXKVQQV-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-hydroxyphenyl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(O)=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ZKTJDFKFXKVQQV-UHFFFAOYSA-N 0.000 claims 1
• DBHRNNUAKNLSTN-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-hydroxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(O)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 DBHRNNUAKNLSTN-UHFFFAOYSA-N 0.000 claims 1
• ZHNKEMCNFZELJQ-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-methoxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(OC)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 ZHNKEMCNFZELJQ-UHFFFAOYSA-N 0.000 claims 1
• NAHKJYKGOJFNHP-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-methoxypyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC=NC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 NAHKJYKGOJFNHP-UHFFFAOYSA-N 0.000 claims 1
• WITZONUAXZSVSW-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-methylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 WITZONUAXZSVSW-UHFFFAOYSA-N 0.000 claims 1
• QNTKEMOFVQAJMA-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-methylpyridin-2-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC=NC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 QNTKEMOFVQAJMA-UHFFFAOYSA-N 0.000 claims 1
• AXWARDICDGUFPI-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-methylsulfonylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(S(=O)(=O)C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 AXWARDICDGUFPI-UHFFFAOYSA-N 0.000 claims 1
• VBTXQZZSAUAITD-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-morpholin-4-ylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=C1)=CC=C1N1CCOCC1 VBTXQZZSAUAITD-UHFFFAOYSA-N 0.000 claims 1
• IVWGHSCCLXSMKT-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-phenoxyphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=C1)=CC=C1OC1=CC=CC=C1 IVWGHSCCLXSMKT-UHFFFAOYSA-N 0.000 claims 1
• FDRQYFLBOAMJSN-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(4-phenylphenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=C1)=CC=C1C1=CC=CC=C1 FDRQYFLBOAMJSN-UHFFFAOYSA-N 0.000 claims 1
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• HWJHLIQKKAJFQU-UHFFFAOYSA-N 9-cyclopropyl-7-(2,3-dihydro-1h-isoindol-5-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3CNCC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 HWJHLIQKKAJFQU-UHFFFAOYSA-N 0.000 claims 1
• XAVSZNMPLSSUPP-UHFFFAOYSA-N 9-cyclopropyl-7-(2,3-dihydro-1h-isoindol-5-yl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C3CNCC3=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 XAVSZNMPLSSUPP-UHFFFAOYSA-N 0.000 claims 1
• IKKAJWSZRDWAQS-UHFFFAOYSA-N 9-cyclopropyl-7-(2,3-dimethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1OC IKKAJWSZRDWAQS-UHFFFAOYSA-N 0.000 claims 1
• QFOGOHVBFAYJBZ-UHFFFAOYSA-N 9-cyclopropyl-7-(2,4-difluorophenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(F)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 QFOGOHVBFAYJBZ-UHFFFAOYSA-N 0.000 claims 1
• JWJQLQKELHKOTI-UHFFFAOYSA-N 9-cyclopropyl-7-(2,4-dimethoxypyrimidin-5-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=NC(OC)=NC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 JWJQLQKELHKOTI-UHFFFAOYSA-N 0.000 claims 1
• ROBDLWAQNDEBRY-UHFFFAOYSA-N 9-cyclopropyl-7-(2,4-dimethylphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 ROBDLWAQNDEBRY-UHFFFAOYSA-N 0.000 claims 1
• OCQIJBLXEGHCQX-UHFFFAOYSA-N 9-cyclopropyl-7-(2,5-difluorophenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC=C(F)C(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 OCQIJBLXEGHCQX-UHFFFAOYSA-N 0.000 claims 1
• FJCOEACJOWLRPL-UHFFFAOYSA-N 9-cyclopropyl-7-(2,5-dimethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC=C(OC)C(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 FJCOEACJOWLRPL-UHFFFAOYSA-N 0.000 claims 1
• UJHORMINDSJFSW-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=CC=CC(OC)=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 UJHORMINDSJFSW-UHFFFAOYSA-N 0.000 claims 1
• QSZTVRPKJCEKPM-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethoxypyridin-3-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=NC(OC)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 QSZTVRPKJCEKPM-UHFFFAOYSA-N 0.000 claims 1
• XPDYWTGTFHDGDY-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC=CC(C)=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 XPDYWTGTFHDGDY-UHFFFAOYSA-N 0.000 claims 1
• RJJIYFJFDDWEDG-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyridin-3-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=NC(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 RJJIYFJFDDWEDG-UHFFFAOYSA-N 0.000 claims 1
• YMFZNLVSPOAGKV-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyridin-4-yl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(C)N=C(C)C=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 YMFZNLVSPOAGKV-UHFFFAOYSA-N 0.000 claims 1
• RJOLUFVOCIYBTB-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyrimidin-4-yl)-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC(=NC(=N1)C)C2=C(C=C3C(=C2OC)N(C4=C(C3=O)C(=O)NS4)C5CC5)F RJOLUFVOCIYBTB-UHFFFAOYSA-N 0.000 claims 1
• KYOINQSKAYHQMB-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyrimidin-4-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC(=NC(=N1)C)C2=C(C=C3C(=C2)N(C4=C(C3=O)C(=O)NS4)C5CC5)F KYOINQSKAYHQMB-UHFFFAOYSA-N 0.000 claims 1
• YZFFQIOYJDLRNK-UHFFFAOYSA-N 9-cyclopropyl-7-(2-ethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CCOC1=CC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 YZFFQIOYJDLRNK-UHFFFAOYSA-N 0.000 claims 1
• AEEMUTZYUFNVKW-UHFFFAOYSA-N 9-cyclopropyl-7-(2-fluoropyridin-3-yl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C(=NC=CC=2)F)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 AEEMUTZYUFNVKW-UHFFFAOYSA-N 0.000 claims 1
• HKDAIGTYYWHVQF-UHFFFAOYSA-N 9-cyclopropyl-7-(3,4-difluorophenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(F)C(F)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 HKDAIGTYYWHVQF-UHFFFAOYSA-N 0.000 claims 1
• DZGGMDFKRTZRKZ-UHFFFAOYSA-N 9-cyclopropyl-7-(3,4-dimethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(OC)C(OC)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 DZGGMDFKRTZRKZ-UHFFFAOYSA-N 0.000 claims 1
• LHDFCQFVZGYKQT-UHFFFAOYSA-N 9-cyclopropyl-7-(3,4-dimethylphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C)C(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 LHDFCQFVZGYKQT-UHFFFAOYSA-N 0.000 claims 1
• CMPHDVXTPLJQSN-UHFFFAOYSA-N 9-cyclopropyl-7-(3,5-difluorophenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(F)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 CMPHDVXTPLJQSN-UHFFFAOYSA-N 0.000 claims 1
• KAFUYEZXFPRCEN-UHFFFAOYSA-N 9-cyclopropyl-7-(3,5-dimethyl-1,2-oxazol-4-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=NOC(C)=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 KAFUYEZXFPRCEN-UHFFFAOYSA-N 0.000 claims 1
• ORBKNLILRFTSQF-UHFFFAOYSA-N 9-cyclopropyl-7-(3,5-dimethylphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC(C)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 ORBKNLILRFTSQF-UHFFFAOYSA-N 0.000 claims 1
• YJAWLQYSBQEWNA-UHFFFAOYSA-N 9-cyclopropyl-7-(3-ethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CCOC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 YJAWLQYSBQEWNA-UHFFFAOYSA-N 0.000 claims 1
• UCAUSBRRDCPYMN-UHFFFAOYSA-N 9-cyclopropyl-7-(4-ethoxyphenyl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(OCC)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 UCAUSBRRDCPYMN-UHFFFAOYSA-N 0.000 claims 1
• SEFOMXRJKFPZRJ-UHFFFAOYSA-N 9-cyclopropyl-7-(4-hydroxy-3-methoxyphenyl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(O)C(OC)=CC(C=2C(=C3C(C(C=4C(=O)NSC=4N3C3CC3)=O)=CC=2)OC)=C1 SEFOMXRJKFPZRJ-UHFFFAOYSA-N 0.000 claims 1
• ZIKIPZPQEUZJTK-UHFFFAOYSA-N 9-cyclopropyl-7-(6-fluoropyridin-3-yl)-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=NC(F)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 ZIKIPZPQEUZJTK-UHFFFAOYSA-N 0.000 claims 1
• JKJDOMFIIYDMOA-UHFFFAOYSA-N 9-cyclopropyl-7-[2-(dimethylamino)-4-methylphenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CN(C)C1=CC(C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 JKJDOMFIIYDMOA-UHFFFAOYSA-N 0.000 claims 1
• WVLIGWNEQZUYGK-UHFFFAOYSA-N 9-cyclopropyl-7-[2-(dimethylamino)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CN(C)C1=CC=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 WVLIGWNEQZUYGK-UHFFFAOYSA-N 0.000 claims 1
• JKIJLPBAIYUZCX-UHFFFAOYSA-N 9-cyclopropyl-7-[3,5-dimethyl-4-(2-piperazin-1-ylethoxy)phenyl]-6-fluoro-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=C(C)C(OCCN3CCNCC3)=C(C)C=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 JKIJLPBAIYUZCX-UHFFFAOYSA-N 0.000 claims 1
• BMRDFZXNCLZVFK-UHFFFAOYSA-N 9-cyclopropyl-7-[3,5-dimethyl-4-(2-piperazin-1-ylethoxy)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=CC(C)=C1OCCN1CCNCC1 BMRDFZXNCLZVFK-UHFFFAOYSA-N 0.000 claims 1
• JCYKRCTVEREHEQ-UHFFFAOYSA-N 9-cyclopropyl-7-[3,5-dimethyl-4-(2-piperazin-1-ylethoxy)phenyl]-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=C(C)C(OCCN3CCNCC3)=C(C)C=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 JCYKRCTVEREHEQ-UHFFFAOYSA-N 0.000 claims 1
• ZDXBOQJLJDEEHM-UHFFFAOYSA-N 9-cyclopropyl-7-[3-(dimethylamino)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CN(C)C1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 ZDXBOQJLJDEEHM-UHFFFAOYSA-N 0.000 claims 1
• ACQYCNMZNGWQTF-UHFFFAOYSA-N 9-cyclopropyl-7-[3-(ethylaminomethyl)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CCNCC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 ACQYCNMZNGWQTF-UHFFFAOYSA-N 0.000 claims 1
• QEXCVUDIUQVBFZ-UHFFFAOYSA-N 9-cyclopropyl-7-[3-[(dimethylamino)methyl]phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CN(C)CC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 QEXCVUDIUQVBFZ-UHFFFAOYSA-N 0.000 claims 1
• MIGWMAOYFKMMLJ-UHFFFAOYSA-N 9-cyclopropyl-7-[4-(dimethylamino)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(N(C)C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 MIGWMAOYFKMMLJ-UHFFFAOYSA-N 0.000 claims 1
• BQIDKOQAEIVUCY-UHFFFAOYSA-N 9-cyclopropyl-7-[4-(ethylaminomethyl)phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(CNCC)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 BQIDKOQAEIVUCY-UHFFFAOYSA-N 0.000 claims 1
• ZGJSRMVDAJTIII-UHFFFAOYSA-N 9-cyclopropyl-7-[4-[(dimethylamino)methyl]phenyl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(CN(C)C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 ZGJSRMVDAJTIII-UHFFFAOYSA-N 0.000 claims 1
• MXFLSYFWQVXPSE-UHFFFAOYSA-N 9-cyclopropyl-7-[5-(4,5-dihydro-1h-imidazol-2-yl)pyridin-3-yl]-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=1)=CN=CC=1C1=NCCN1 MXFLSYFWQVXPSE-UHFFFAOYSA-N 0.000 claims 1
• WZOIBHYJLOSVHM-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-(1-methyl-2,3-dihydro-1h-isoindol-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=C3CNC(C)C3=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 WZOIBHYJLOSVHM-UHFFFAOYSA-N 0.000 claims 1
• VACGDJABSZROER-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-(2-methylpyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C(=NC=CC=2)C)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 VACGDJABSZROER-UHFFFAOYSA-N 0.000 claims 1
• XFTNNMSJXKSIMA-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-(6-methylpyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=NC(C)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 XFTNNMSJXKSIMA-UHFFFAOYSA-N 0.000 claims 1
• QBESUYKRSZTYTR-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-[4-(2-piperazin-1-ylethoxy)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=CC(OCCN3CCNCC3)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 QBESUYKRSZTYTR-UHFFFAOYSA-N 0.000 claims 1
• DFCMOIUETCAXAG-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-[4-(morpholin-4-ylmethyl)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(CN3CCOCC3)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 DFCMOIUETCAXAG-UHFFFAOYSA-N 0.000 claims 1
• IKCAWSHXFBPNJE-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-[4-(piperazin-1-ylmethyl)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CC(CN3CCNCC3)=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 IKCAWSHXFBPNJE-UHFFFAOYSA-N 0.000 claims 1
• SQGWLQXHWRAYRN-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-pyridin-4-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=CN=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 SQGWLQXHWRAYRN-UHFFFAOYSA-N 0.000 claims 1
• JXNVVEBRANZDHJ-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-quinolin-6-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione;hydrochloride Chemical compound Cl.COC1=C(C=2C=C3C=CC=NC3=CC=2)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 JXNVVEBRANZDHJ-UHFFFAOYSA-N 0.000 claims 1
• BLKSFMKFNQPFOG-UHFFFAOYSA-N n-[3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]-5-(dimethylamino)naphthalene-1-sulfonamide Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1S(=O)(=O)NC(C=1)=CC=CC=1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 BLKSFMKFNQPFOG-UHFFFAOYSA-N 0.000 claims 1
• FVYWIEGGEGDGHL-UHFFFAOYSA-N n-[3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]acetamide Chemical compound CC(=O)NC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 FVYWIEGGEGDGHL-UHFFFAOYSA-N 0.000 claims 1
• GZODDISSRKLIGR-UHFFFAOYSA-N n-[3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 GZODDISSRKLIGR-UHFFFAOYSA-N 0.000 claims 1
• DPRHJTJVSVPIFK-UHFFFAOYSA-N n-[4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]-2-(dimethylamino)acetamide Chemical compound C1=CC(NC(=O)CN(C)C)=CC=C1C(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 DPRHJTJVSVPIFK-UHFFFAOYSA-N 0.000 claims 1
• HPIJVKIPDKCHTJ-UHFFFAOYSA-N n-[4-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)phenyl]-2-morpholin-4-ylacetamide Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(C=C1)=CC=C1NC(=O)CN1CCOCC1 HPIJVKIPDKCHTJ-UHFFFAOYSA-N 0.000 claims 1
• RUFGWEMYAALXCD-UHFFFAOYSA-N tert-butyl 4-[5-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)pyridin-2-yl]piperazine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCN1C1=CC=C(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)C=N1 RUFGWEMYAALXCD-UHFFFAOYSA-N 0.000 claims 1
• 238000005481 NMR spectroscopy Methods 0.000 description 62
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 48
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 45
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 37
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
• 238000000034 method Methods 0.000 description 36
• 239000011541 reaction mixture Substances 0.000 description 36
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