KR20060069836A - 항-감염제로서의 이소티아졸로퀴놀론 및 관련 화합물 - Google Patents

Info

Publication number

KR20060069836A

KR20060069836A KR1020067002923A KR20067002923A KR20060069836A KR 20060069836 A KR20060069836 A KR 20060069836A KR 1020067002923 A KR1020067002923 A KR 1020067002923A KR 20067002923 A KR20067002923 A KR 20067002923A KR 20060069836 A KR20060069836 A KR 20060069836A

Authority

KR

South Korea

Prior art keywords

alkyl

cyclopropyl

isothiazolo

fluoro

quinoline

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.)

Ceased

Links

• Espacenet
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 305
• 239000004599 antimicrobial Substances 0.000 title description 9
• QXHKKCITURTUFC-UHFFFAOYSA-N [1,2]thiazolo[3,4-h]quinoline 8-oxide Chemical compound C1=CN=C2C3=CS(=O)N=C3C=CC2=C1 QXHKKCITURTUFC-UHFFFAOYSA-N 0.000 title description 4
• 229960005475 antiinfective agent Drugs 0.000 title 1
• 150000003839 salts Chemical class 0.000 claims abstract description 111
• 239000000203 mixture Substances 0.000 claims abstract description 80
• 238000000034 method Methods 0.000 claims abstract description 42
• 208000015181 infectious disease Diseases 0.000 claims abstract description 34
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 25
• 241001465754 Metazoa Species 0.000 claims abstract description 20
• 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 19
• 230000001580 bacterial effect Effects 0.000 claims abstract description 12
• 239000003085 diluting agent Substances 0.000 claims abstract description 10
• -1 hydroxy, amino Chemical group 0.000 claims description 279
• 125000000217 alkyl group Chemical group 0.000 claims description 260
• 125000001424 substituent group Chemical group 0.000 claims description 99
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 98
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 83
• 229910052736 halogen Inorganic materials 0.000 claims description 81
• 150000002367 halogens Chemical class 0.000 claims description 75
• 125000001188 haloalkyl group Chemical group 0.000 claims description 74
• 239000000243 solution Substances 0.000 claims description 67
• 125000003282 alkyl amino group Chemical group 0.000 claims description 66
• 125000003118 aryl group Chemical group 0.000 claims description 65
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
• CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 65
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 63
• 125000003545 alkoxy group Chemical group 0.000 claims description 58
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 48
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 44
• PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 40
• 125000004076 pyridyl group Chemical group 0.000 claims description 36
• 229910052799 carbon Inorganic materials 0.000 claims description 34
• 229910052739 hydrogen Inorganic materials 0.000 claims description 34
• 239000001257 hydrogen Substances 0.000 claims description 33
• 229910052757 nitrogen Inorganic materials 0.000 claims description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 32
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 31
• 125000001544 thienyl group Chemical group 0.000 claims description 31
• 125000003386 piperidinyl group Chemical group 0.000 claims description 28
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• 125000002541 furyl group Chemical group 0.000 claims description 23
• 125000004193 piperazinyl group Chemical group 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
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
• 125000001624 naphthyl group Chemical group 0.000 claims description 22
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
• 150000002431 hydrogen Chemical class 0.000 claims description 20
• 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
• 125000001072 heteroaryl group Chemical group 0.000 claims description 19
• 125000004043 oxo group Chemical group O=* 0.000 claims description 19
• 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 18
• 244000005700 microbiome Species 0.000 claims description 18
• 229910052760 oxygen Inorganic materials 0.000 claims description 18
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 18
• 229910052717 sulfur Inorganic materials 0.000 claims description 18
• 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 18
• 125000001041 indolyl group Chemical group 0.000 claims description 17
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 16
• 241000588724 Escherichia coli Species 0.000 claims description 15
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
• 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 15
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 14
• 239000003242 anti bacterial agent Substances 0.000 claims description 14
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 14
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
• 150000001721 carbon Chemical group 0.000 claims description 13
• 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 13
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 13
• 230000000844 anti-bacterial effect Effects 0.000 claims description 12
• 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 10
• 125000002619 bicyclic group Chemical group 0.000 claims description 10
• 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 10
• 125000005843 halogen group Chemical group 0.000 claims description 10
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 10
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 9
• 239000000499 gel Substances 0.000 claims description 9
• 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 9
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 8
• 125000002252 acyl group Chemical group 0.000 claims description 8
• 229940121375 antifungal agent Drugs 0.000 claims description 8
• 125000005046 dihydronaphthyl group Chemical group 0.000 claims description 8
• 239000003937 drug carrier Substances 0.000 claims description 8
• 239000003112 inhibitor Substances 0.000 claims description 8
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 8
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
• 239000006188 syrup Substances 0.000 claims description 8
• 235000020357 syrup Nutrition 0.000 claims description 8
• 239000003826 tablet Substances 0.000 claims description 8
• 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 8
• 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 8
• 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 239000003429 antifungal agent Substances 0.000 claims description 7
• 239000003782 beta lactam antibiotic agent Substances 0.000 claims description 7
• 125000001153 fluoro group Chemical group F* 0.000 claims description 7
• 239000002132 β-lactam antibiotic Substances 0.000 claims description 7
• 229940124586 β-lactam antibiotics Drugs 0.000 claims description 7
• 239000003443 antiviral agent Substances 0.000 claims description 6
• 239000006071 cream Substances 0.000 claims description 6
• 239000004093 hydrolase inhibitor Substances 0.000 claims description 6
• 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
• 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
• IGLVERVMCZAZHD-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-phenyl-[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=C1 IGLVERVMCZAZHD-UHFFFAOYSA-N 0.000 claims description 5
• 241000251468 Actinopterygii Species 0.000 claims description 5
• 206010018612 Gonorrhoea Diseases 0.000 claims description 5
• 239000002775 capsule Substances 0.000 claims description 5
• 125000002837 carbocyclic group Chemical group 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 239000007788 liquid Substances 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• CPWIIFYGKOXEBI-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyridin-4-yl)-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound CC1=NC(C)=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 CPWIIFYGKOXEBI-UHFFFAOYSA-N 0.000 claims description 4
• 208000007190 Chlamydia Infections Diseases 0.000 claims description 4
• 102000014150 Interferons Human genes 0.000 claims description 4
• 108010050904 Interferons Proteins 0.000 claims description 4
• 229940047124 interferons Drugs 0.000 claims description 4
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
• 206010035664 Pneumonia Diseases 0.000 claims description 3
• 239000000443 aerosol Substances 0.000 claims description 3
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
• KTUXZCJQJNQPPH-UHFFFAOYSA-N quinoline-3,4-dione Chemical compound C1=CC=C2C(=O)C(=O)C=NC2=C1 KTUXZCJQJNQPPH-UHFFFAOYSA-N 0.000 claims description 3
• 210000003708 urethra Anatomy 0.000 claims description 3
• 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
• 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
• ILCYXLQBTVXHOU-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(1,2,3,6-tetrahydropyridin-4-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CCNCC1 ILCYXLQBTVXHOU-UHFFFAOYSA-N 0.000 claims description 2
• 206010060968 Arthritis infective Diseases 0.000 claims description 2
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 2
• 206010012742 Diarrhoea infectious Diseases 0.000 claims description 2
• 206010061977 Genital infection female Diseases 0.000 claims description 2
• 206010024971 Lower respiratory tract infections Diseases 0.000 claims description 2
• 206010031252 Osteomyelitis Diseases 0.000 claims description 2
• 206010058674 Pelvic Infection Diseases 0.000 claims description 2
• 206010037596 Pyelonephritis Diseases 0.000 claims description 2
• 208000037386 Typhoid Diseases 0.000 claims description 2
• 206010006451 bronchitis Diseases 0.000 claims description 2
• 208000001848 dysentery Diseases 0.000 claims description 2
• 125000004356 hydroxy functional group Chemical group O* 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
• 206010040872 skin infection Diseases 0.000 claims description 2
• SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 2
• 201000008297 typhoid fever Diseases 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
• 241000125205 Anethum Species 0.000 claims 2
• YMFUFNCNIHAZOD-UHFFFAOYSA-N (9-cyclopropyl-6-fluoro-4-oxo-7-pyridin-4-yl-[1,2]thiazolo[5,4-b]quinolin-3-yl) acetate Chemical compound C12=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C=2C(OC(=O)C)=NSC=2N1C1CC1 YMFUFNCNIHAZOD-UHFFFAOYSA-N 0.000 claims 1
• 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
• QNQWAMFKYJZNQF-UHFFFAOYSA-N 2-[4-(9-cyclopropyl-6-fluoro-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(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 QNQWAMFKYJZNQF-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
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 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
• 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
• 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
• VFPBQKKMMFDEGW-UHFFFAOYSA-N 3-[6-fluoro-9-(2-fluorocyclopropyl)-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl]benzonitrile Chemical compound FC1CC1N1C2=CC(C=3C=C(C=CC=3)C#N)=C(F)C=C2C(=O)C2=C1SNC2=O VFPBQKKMMFDEGW-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
• OUAOQRPICPBFFR-UHFFFAOYSA-N 4-(9-cyclopropyl-6-fluoro-3,4-dioxo-7-pyridin-4-yl-[1,2]thiazolo[5,4-b]quinolin-2-yl)butanoic acid Chemical compound C12=CC(C=3C=CN=CC=3)=C(F)C=C2C(=O)C=2C(=O)N(CCCC(=O)O)SC=2N1C1CC1 OUAOQRPICPBFFR-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
• NBIULWYQGDTGLK-UHFFFAOYSA-N 7-(1-acetyl-3,6-dihydro-2h-pyridin-4-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1N(C(=O)C)CCC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 NBIULWYQGDTGLK-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
• 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
• ZWDXPDRGKQHBHR-UHFFFAOYSA-N 7-(6-amino-5,6,7,8-tetrahydronaphthalen-2-yl)-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C=1C=C2CC(N)CCC2=CC=1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 ZWDXPDRGKQHBHR-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
• PIHMVMSLZWVLBR-UHFFFAOYSA-N 7-[2-(4-aminophenyl)ethynyl]-9-cyclopropyl-6-fluoro-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=CC(N)=CC=C1C#CC(C(=C1)F)=CC2=C1C(=O)C(C(=O)NS1)=C1N2C1CC1 PIHMVMSLZWVLBR-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
• 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
• KRGWTBPYXBSDKE-UHFFFAOYSA-N 9-(2,4-difluorophenyl)-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)=C1N2C1=CC=C(F)C=C1F KRGWTBPYXBSDKE-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 class 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
• RURVIBJKQFZLPR-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-phenylethenyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C=CC1=CC=CC=C1 RURVIBJKQFZLPR-UHFFFAOYSA-N 0.000 claims 1
• KTHQLGONTKYPQO-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-phenylethynyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C#CC1=CC=CC=C1 KTHQLGONTKYPQO-UHFFFAOYSA-N 0.000 claims 1
• IFHRZWOMYPJZAX-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-pyridin-3-ylethynyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C#CC1=CC=CN=C1 IFHRZWOMYPJZAX-UHFFFAOYSA-N 0.000 claims 1
• OBMLBKYYNHVRCO-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(2-pyridin-4-ylethynyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C#CC1=CC=NC=C1 OBMLBKYYNHVRCO-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
• SPBNMZKFDNAGRB-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-(3-morpholin-4-ylprop-1-enyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C=CCN1CCOCC1 SPBNMZKFDNAGRB-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
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• WKPDUCKQUZBGHI-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-(piperazin-1-ylmethyl)phenyl]-[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=C1CN1CCNCC1 WKPDUCKQUZBGHI-UHFFFAOYSA-N 0.000 claims 1
• KKLABWRQTOPKEJ-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-(piperidin-1-ylmethyl)phenyl]-[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=C1CN1CCCCC1 KKLABWRQTOPKEJ-UHFFFAOYSA-N 0.000 claims 1
• SUQNNGRPTDESSL-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-(piperidine-1-carbonyl)phenyl]-[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=C1C(=O)N1CCCCC1 SUQNNGRPTDESSL-UHFFFAOYSA-N 0.000 claims 1
• WIFHEQYVBQQKHK-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-(pyrrolidine-1-carbonyl)phenyl]-[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=C1C(=O)N1CCCC1 WIFHEQYVBQQKHK-UHFFFAOYSA-N 0.000 claims 1
• UCRNNYPIRHITCE-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-(trifluoromethoxy)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=C(OC(F)(F)F)C=C1 UCRNNYPIRHITCE-UHFFFAOYSA-N 0.000 claims 1
• YBCSUPWEJLCXTB-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-(trifluoromethyl)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1=CC=C(C(F)(F)F)C=C1 YBCSUPWEJLCXTB-UHFFFAOYSA-N 0.000 claims 1
• DYHHRJCDMMKLHJ-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-[4-[(2-oxo-1,3-oxazolidin-4-yl)methyl]phenyl]-[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=C1CC1COC(=O)N1 DYHHRJCDMMKLHJ-UHFFFAOYSA-N 0.000 claims 1
• OMXVFQQUHGDGGN-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-isoquinolin-4-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C3=CC=CC=C3C=NC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 OMXVFQQUHGDGGN-UHFFFAOYSA-N 0.000 claims 1
• VBDBVGOJRRMHMG-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-isoquinolin-5-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C3=CC=NC=C3C=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 VBDBVGOJRRMHMG-UHFFFAOYSA-N 0.000 claims 1
• YQBZZXCNAOOMLT-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-isoquinolin-6-yl-8-methoxy-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C3C=CN=CC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 YQBZZXCNAOOMLT-UHFFFAOYSA-N 0.000 claims 1
• TUOOJOYIRPNXDT-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-isoquinolin-6-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3C=CN=CC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 TUOOJOYIRPNXDT-UHFFFAOYSA-N 0.000 claims 1
• UQKDLCHGHCBTPK-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-naphthalen-2-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3C=CC=CC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 UQKDLCHGHCBTPK-UHFFFAOYSA-N 0.000 claims 1
• OEXHGKHRCUKEQM-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-piperidin-4-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C1CCNCC1 OEXHGKHRCUKEQM-UHFFFAOYSA-N 0.000 claims 1
• VGXSEFMYPYGXAQ-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-pyrazin-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=CN=CC=N1 VGXSEFMYPYGXAQ-UHFFFAOYSA-N 0.000 claims 1
• XFFNZYGEEVRMSC-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-pyridin-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=C1 XFFNZYGEEVRMSC-UHFFFAOYSA-N 0.000 claims 1
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• QWZPNYZFBDOWMD-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-7-quinolin-6-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C(C=2C=C3C=CC=NC3=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 QWZPNYZFBDOWMD-UHFFFAOYSA-N 0.000 claims 1
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• AEXXNEACCPUNGC-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-[3-(2-piperazin-1-ylethoxy)phenyl]-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=C(OCCN3CCNCC3)C=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 AEXXNEACCPUNGC-UHFFFAOYSA-N 0.000 claims 1
• OBCFUXBVUMCQEP-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-8-methoxy-7-pyridin-4-yl-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C=CN=CC=2)C(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 OBCFUXBVUMCQEP-UHFFFAOYSA-N 0.000 claims 1
• 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
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• 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
• VSJDXWLCKGBBNW-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyridin-4-yl)-6-fluoro-5-(2-methylhydrazinyl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=2SNC(=O)C=2C(=O)C=2C(NNC)=C(F)C(C=3C=C(C)N=C(C)C=3)=CC=2N1C1CC1 VSJDXWLCKGBBNW-UHFFFAOYSA-N 0.000 claims 1
• BGJYJHMNNGVNLK-UHFFFAOYSA-N 9-cyclopropyl-7-(2,6-dimethylpyridin-4-yl)-6-fluoro-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(F)=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 BGJYJHMNNGVNLK-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
• 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
• KBVIMEJOJXOQPA-UHFFFAOYSA-N 9-cyclopropyl-7-(4-ethenylphenyl)-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=C(C=C)C=C1 KBVIMEJOJXOQPA-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
• 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
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