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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| EP1809639B1 (en) * | 2004-11-11 | 2009-10-14 | Achillion Pharmaceuticals, Inc. | 8a, 9-dihydro-4a-h-isothiazolo[5,4-b] quinoline-3, 4-diones and related compounds as anti-infective agents |
| WO2006074317A1 (en) * | 2005-01-05 | 2006-07-13 | Achillion Pharmaceuticals, Inc. | 1-thia-2,4a-diaza-cyclopenta[b]naphthalene-3,4-diones and related compounds as anti-infective agents |
| ES2352799T3 (es) | 2005-07-27 | 2011-02-23 | Achillion Pharmaceuticals, Inc. | 8-metoxi-9h-isotiazolo[5,4-b]quinolina-3,4-dionas y compuestos relacionados. |
| 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 |
| US8173636B2 (en) * | 2009-04-03 | 2012-05-08 | Achillion Pharmaceuticals, Inc. | Hydroxylthienoquinolones and related compounds as anti-infective agents |
| WO2011031745A1 (en) | 2009-09-09 | 2011-03-17 | Achaogen, Inc. | Antibacterial fluoroquinolone analogs |
| JP2013508299A (ja) | 2009-10-16 | 2013-03-07 | リブ−エックス ファーマシューティカルズ，インコーポレイテッド | 抗微生物性化合物および抗微生物性化合物の製造方法および使用方法 |
| NZ623384A (en) * | 2009-10-16 | 2016-06-24 | Melinta Therapeutics Inc | Antimicrobial compounds and methods of making and using the same |
| JP6274723B2 (ja) | 2009-10-16 | 2018-02-07 | メリンタ セラピューティクス，インコーポレイテッド | 抗微生物性化合物および抗微生物性化合物の製造方法および使用方法 |
| 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 |
| US9937183B2 (en) | 2013-09-09 | 2018-04-10 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| MX2016002975A (es) | 2013-09-09 | 2016-10-21 | Melinta Therapeutics Inc | Compuestos antimicrobianos y métodos de fabricación y utilización de los mismos. |
| 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 |
| WO2016145417A1 (en) | 2015-03-11 | 2016-09-15 | Melinta Therapeutics, Inc. | Antimicrobial compounds and methods of making and using the same |
| US11098047B2 (en) | 2016-05-06 | 2021-08-24 | BioVersys AG | Antimicrobials and methods of making and using same |
| 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 |
| 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 |
| 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 |
| CN122213010A (zh) * | 2026-05-20 | 2026-06-16 | 山东丰金制药有限公司 | 一种苏泽曲林中间体4-氨基吡啶-2-甲酸甲酯的制备方法 |
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| US4767762A (en) * | 1985-12-23 | 1988-08-30 | Abbott Laboratories | Tricyclic quinoline and naphthyride antibacterials |
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| 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 |
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| US7678235B2 (en) * | 2005-10-19 | 2010-03-16 | Sylvan Source, Inc. | Water purification system |
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- 2004-08-04 BR BRPI0413528-8A patent/BRPI0413528A/pt not_active IP Right Cessation
- 2004-08-04 CA CA2535370A patent/CA2535370C/en not_active Expired - Fee Related
- 2004-08-04 JP JP2006523236A patent/JP5147237B2/ja not_active Expired - Fee Related
- 2004-08-04 WO PCT/US2004/025365 patent/WO2005019228A1/en not_active Ceased
- 2004-08-04 US US10/911,406 patent/US20050075363A1/en not_active Abandoned
- 2004-08-04 CN CNA2004800299554A patent/CN1867570A/zh active Pending
- 2004-08-04 MX MXPA06001645A patent/MXPA06001645A/es not_active Application Discontinuation
- 2004-08-04 UA UAA200602630A patent/UA84879C2/ru unknown
-
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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