JP2007502275A5 - - Google Patents
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- Publication number
- JP2007502275A5 JP2007502275A5 JP2006523236A JP2006523236A JP2007502275A5 JP 2007502275 A5 JP2007502275 A5 JP 2007502275A5 JP 2006523236 A JP2006523236 A JP 2006523236A JP 2006523236 A JP2006523236 A JP 2006523236A JP 2007502275 A5 JP2007502275 A5 JP 2007502275A5
- Authority
- JP
- Japan
- Prior art keywords
- cyclopropyl
- fluoro
- alkyl
- isothiazolo
- quinoline
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 115
- -1 hydroxy, amino Chemical group 0.000 claims 77
- 150000003839 salts Chemical class 0.000 claims 66
- 150000001875 compounds Chemical class 0.000 claims 64
- 125000001424 substituent group Chemical group 0.000 claims 44
- 125000000753 cycloalkyl group Chemical group 0.000 claims 40
- 229910052736 halogen Inorganic materials 0.000 claims 40
- 150000002367 halogens Chemical class 0.000 claims 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 39
- 125000001188 haloalkyl group Chemical group 0.000 claims 34
- 125000004438 haloalkoxy group Chemical group 0.000 claims 33
- 125000004093 cyano group Chemical group *C#N 0.000 claims 32
- 125000003282 alkyl amino group Chemical group 0.000 claims 31
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 23
- 125000003545 alkoxy group Chemical group 0.000 claims 22
- 229910052739 hydrogen Inorganic materials 0.000 claims 17
- 239000001257 hydrogen Substances 0.000 claims 17
- 125000004076 pyridyl group Chemical group 0.000 claims 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 14
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 12
- 229910052799 carbon Inorganic materials 0.000 claims 12
- 125000003386 piperidinyl group Chemical group 0.000 claims 12
- 125000003118 aryl group Chemical group 0.000 claims 11
- 150000002431 hydrogen Chemical class 0.000 claims 11
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 10
- 125000001624 naphthyl group Chemical group 0.000 claims 10
- 125000004043 oxo group Chemical group O=* 0.000 claims 10
- 125000004193 piperazinyl group Chemical group 0.000 claims 10
- 125000001544 thienyl group Chemical group 0.000 claims 10
- 125000002541 furyl group Chemical group 0.000 claims 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 9
- 125000000168 pyrrolyl group Chemical group 0.000 claims 9
- 229920006395 saturated elastomer Polymers 0.000 claims 9
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 125000002757 morpholinyl group Chemical group 0.000 claims 8
- 125000003373 pyrazinyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 8
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 8
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 8
- 150000001721 carbon Chemical group 0.000 claims 7
- 125000001041 indolyl group Chemical group 0.000 claims 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 7
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 6
- 125000002619 bicyclic group Chemical group 0.000 claims 6
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 6
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims 6
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims 6
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 6
- 125000000842 isoxazolyl group Chemical group 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims 5
- 125000005046 dihydronaphthyl group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 4
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 3
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 3
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 3
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims 3
- 125000001153 fluoro group Chemical group F* 0.000 claims 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 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 3
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 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
- 208000035143 Bacterial infection Diseases 0.000 claims 2
- 241000588724 Escherichia coli Species 0.000 claims 2
- 208000022362 bacterial infectious disease Diseases 0.000 claims 2
- 239000003085 diluting agent Substances 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229910052717 sulfur Inorganic materials 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
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[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
- 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
- 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
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 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
- 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
- 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
- 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
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| WO2006118605A2 (en) * | 2004-11-11 | 2006-11-09 | Achillion Pharmaceuticals, Inc. | 8a, 9-dihydro-4a-h-isothiazolo[5,4-b] quinoline-3, 4-diones and related compounds as anti-infective agents |
| US7659399B2 (en) | 2005-01-05 | 2010-02-09 | Achillion Pharmaceuticals, Inc. | 1-thia-2,4a-diaza-cyclopenta[b]napththalene-3,4-diones and related compounds as anti-infective agents |
| BRPI0607723A2 (pt) * | 2005-02-16 | 2009-10-06 | Achillion Pharmaceuticals Inc | isotiazoloquinolonas e compostos relacionados como agentes antiinfecciosos |
| AU2006272571B2 (en) * | 2005-07-27 | 2012-03-08 | Achillion Pharmaceuticals, Inc. | 8-methoxy-9H-isothiazolo[5,4-B]quinoline-3,4-diones and related compounds as anti-infective agents |
| WO2008021491A2 (en) | 2006-08-16 | 2008-02-21 | Achillion Pharmaceuticals, Inc. | Method for synthesis of 8-alkoxy-9h-isothiazolo[5,4-b]quinoline-3,4-diones |
| WO2008036420A2 (en) * | 2006-09-21 | 2008-03-27 | Achillion Pharmaceuticals, Inc. | 9-(heteroaryl)-isothiazolo[5,4-b]quinoline-3,4-diones and related compounds as anti-infective agents |
| WO2010115184A2 (en) * | 2009-04-03 | 2010-10-07 | Achillion Pharmaceuticals, Inc. | Hydroxythienoquinolones and related compounds as anti-infective agents |
| WO2011031745A1 (en) | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| US9216979B2 (en) | 2009-10-16 | 2015-12-22 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| TW201726630A (zh) * | 2009-10-16 | 2017-08-01 | 梅林塔療法公司 | 抗微生物性化合物及其製造與使用方法 |
| WO2011047320A2 (en) * | 2009-10-16 | 2011-04-21 | Rib-X Pharmaceuticals, Inc. | Antimicrobial compounds and methods of making and using the same |
| CN102866153B (zh) * | 2012-09-29 | 2014-08-13 | 郑州安图生物工程股份有限公司 | 前列腺炎联合检测试剂盒 |
| KR20160070066A (ko) | 2013-09-09 | 2016-06-17 | 멜린타 테라퓨틱스, 인크. | 항균 화합물, 및 이의 제조 방법 및 이용 방법 |
| EP3038623A4 (en) | 2013-09-09 | 2017-04-19 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| CN104530034B (zh) * | 2014-12-31 | 2017-02-22 | 西南大学 | 喹诺酮噻唑类化合物及其制备方法和应用 |
| CA2979342A1 (en) | 2015-03-11 | 2016-09-15 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| WO2017193016A1 (en) | 2016-05-06 | 2017-11-09 | Melinta Therapeutics, Inc. | Antimicrobials and methods of making and using same |
| KR101891315B1 (ko) | 2017-08-01 | 2018-08-24 | 한국화학연구원 | 퀴놀린 4-온 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물 |
| KR101915550B1 (ko) | 2016-10-20 | 2018-11-07 | 한국화학연구원 | 퀴놀린 4-온 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물 |
| CN113045589B (zh) * | 2019-12-27 | 2024-08-23 | 广东东阳光药业股份有限公司 | 流感病毒复制抑制剂及其用途 |
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| US4767762A (en) * | 1985-12-23 | 1988-08-30 | Abbott Laboratories | Tricyclic quinoline and naphthyride antibacterials |
| JPS62187472A (ja) * | 1985-12-23 | 1987-08-15 | アボツト ラボラトリ−ズ | イソオキサゾロ−ナフチリジン、イソオキサゾロキノリン、イソチアゾロ−ナフチリジン及びイソチアゾロ−キノリン誘導体 |
| JP2681190B2 (ja) * | 1988-04-13 | 1997-11-26 | 塩野義製薬株式会社 | ピリドン系抗菌剤 |
| US5328908A (en) * | 1988-10-24 | 1994-07-12 | Procter & Gamble Pharmaceuticals, Inc. | Antimicrobial quinolone thioureas |
| CA2001203C (en) * | 1988-10-24 | 2001-02-13 | Thomas P. Demuth, Jr. | Novel antimicrobial dithiocarbamoyl quinolones |
| US4945160A (en) * | 1988-11-22 | 1990-07-31 | Warner-Lambert Company | Preparation of certain 7-substituted quinolones |
| JP2787713B2 (ja) * | 1989-07-28 | 1998-08-20 | 富山化学工業株式会社 | 新規なイソチアゾローナフチリジンおよびイソチアゾローキノリン誘導体並びにそれらの塩 |
| US5646163A (en) * | 1992-10-30 | 1997-07-08 | The Procter & Gamble Company | Quinolone 5-(N-heterosubstituted amino) antimicrobials |
| US20020103115A1 (en) * | 2000-09-19 | 2002-08-01 | Karl Guegler | Isolated human transporter proteins, nucleic acid molecules encoding human transporter proteins, and uses thereof |
| US7678235B2 (en) * | 2005-10-19 | 2010-03-16 | Sylvan Source, Inc. | Water purification system |
| BRPI0607723A2 (pt) * | 2005-02-16 | 2009-10-06 | Achillion Pharmaceuticals Inc | isotiazoloquinolonas e compostos relacionados como agentes antiinfecciosos |
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2004
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- 2004-08-04 CA CA2535370A patent/CA2535370C/en not_active Expired - Fee Related
- 2004-08-04 UA UAA200602630A patent/UA84879C2/ru unknown
- 2004-08-04 EP EP04780234A patent/EP1664062B1/en not_active Expired - Lifetime
- 2004-08-04 BR BRPI0413528-8A patent/BRPI0413528A/pt not_active IP Right Cessation
- 2004-08-04 NZ NZ545157A patent/NZ545157A/en not_active IP Right Cessation
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- 2004-08-04 US US10/911,406 patent/US20050075363A1/en not_active Abandoned
- 2004-08-04 MX MXPA06001645A patent/MXPA06001645A/es not_active Application Discontinuation
- 2004-08-04 JP JP2006523236A patent/JP5147237B2/ja not_active Expired - Fee Related
- 2004-08-04 AU AU2004267052A patent/AU2004267052B2/en not_active Ceased
- 2004-08-04 CN CNA2004800299554A patent/CN1867570A/zh active Pending
-
2006
- 2006-01-31 IL IL173492A patent/IL173492A0/en unknown
- 2006-02-09 NO NO20060653A patent/NO20060653L/no not_active Application Discontinuation
-
2011
- 2011-03-14 US US13/047,150 patent/US20110223132A1/en not_active Abandoned
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