CA2535370C - Isothiazoloquinolones and related compounds as anti-infective agents - Google Patents
Isothiazoloquinolones and related compounds as anti-infective agents Download PDFInfo
- Publication number
- CA2535370C CA2535370C CA2535370A CA2535370A CA2535370C CA 2535370 C CA2535370 C CA 2535370C CA 2535370 A CA2535370 A CA 2535370A CA 2535370 A CA2535370 A CA 2535370A CA 2535370 C CA2535370 C CA 2535370C
- Authority
- CA
- Canada
- Prior art keywords
- cyclopropyl
- isothiazolo
- fluoro
- quinoline
- dione
- 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.)
- Expired - Fee Related
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 296
- 239000004599 antimicrobial Substances 0.000 title description 10
- 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 2
- 229960005475 antiinfective agent Drugs 0.000 title 1
- 150000003839 salts Chemical class 0.000 claims abstract description 123
- 239000000203 mixture Substances 0.000 claims abstract description 102
- 238000000034 method Methods 0.000 claims abstract description 43
- 208000015181 infectious disease Diseases 0.000 claims abstract description 37
- 241001465754 Metazoa Species 0.000 claims abstract description 22
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 21
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 14
- 230000001580 bacterial effect Effects 0.000 claims abstract description 13
- 239000003085 diluting agent Substances 0.000 claims abstract description 10
- -1 or R2 is C1-C8alkyl Chemical group 0.000 claims description 230
- 125000001424 substituent group Chemical group 0.000 claims description 90
- 125000003118 aryl group Chemical group 0.000 claims description 86
- 229910052736 halogen Inorganic materials 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 81
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 81
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 70
- 125000003282 alkyl amino group Chemical group 0.000 claims description 65
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 65
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 58
- 125000001544 thienyl group Chemical group 0.000 claims description 43
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 39
- 229910052757 nitrogen Inorganic materials 0.000 claims description 39
- 125000004076 pyridyl group Chemical group 0.000 claims description 39
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 37
- 229910052799 carbon Inorganic materials 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 229910052760 oxygen Inorganic materials 0.000 claims description 32
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 125000004193 piperazinyl group Chemical group 0.000 claims description 24
- 125000002541 furyl 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
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 22
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 21
- 125000002883 imidazolyl group Chemical group 0.000 claims description 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 20
- 244000005700 microbiome Species 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
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 18
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 17
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 17
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 125000004043 oxo group Chemical group O=* 0.000 claims description 16
- 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
- 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
- 150000001721 carbon Chemical group 0.000 claims description 14
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 14
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 13
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 13
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 12
- 241000588724 Escherichia coli Species 0.000 claims description 12
- 125000002619 bicyclic group Chemical group 0.000 claims description 12
- 208000035143 Bacterial infection Diseases 0.000 claims description 11
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 11
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 8
- 101150020251 NR13 gene Proteins 0.000 claims description 8
- 230000000844 anti-bacterial effect Effects 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 239000003112 inhibitor Substances 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
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 8
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 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
- 229940121375 antifungal agent Drugs 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 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 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 239000006071 cream Substances 0.000 claims description 6
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 6
- 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
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 206010018612 Gonorrhoea Diseases 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 239000003443 antiviral agent Substances 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 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
- 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 4
- 206010061041 Chlamydial infection Diseases 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 239000003429 antifungal agent Substances 0.000 claims description 4
- 239000003904 antiprotozoal agent Substances 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- 208000028172 protozoa infectious disease Diseases 0.000 claims description 4
- 208000019206 urinary tract infection Diseases 0.000 claims description 4
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 206010035664 Pneumonia Diseases 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229940054534 ophthalmic solution Drugs 0.000 claims description 3
- 239000002997 ophthalmic solution Substances 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
- 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 description 2
- 206010001076 Acute sinusitis Diseases 0.000 claims description 2
- 206010060968 Arthritis infective Diseases 0.000 claims description 2
- 206010012742 Diarrhoea infectious Diseases 0.000 claims description 2
- 241000270322 Lepidosauria Species 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
- 239000012530 fluid Substances 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
- 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
- 206010040872 skin infection Diseases 0.000 claims description 2
- QTAFXMIKBKQWGJ-UHFFFAOYSA-N tert-butyl n-[6-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate Chemical compound C=1C=C2CC(NC(=O)OC(C)(C)C)CCC2=CC=1C(C(=CC=1C(=O)C=2C(=O)NSC=22)F)=CC=1N2C1CC1 QTAFXMIKBKQWGJ-UHFFFAOYSA-N 0.000 claims description 2
- 201000008297 typhoid fever Diseases 0.000 claims description 2
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims 23
- 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
- 201000000902 chlamydia Diseases 0.000 claims 2
- 208000012538 chlamydia trachomatis infectious disease Diseases 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
- 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
- MIRPEVDMURQGBL-UHFFFAOYSA-N 3-(9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinolin-7-yl)benzamide Chemical compound NC(=O)C1=CC=CC(C=2C(=CC=3C(=O)C=4C(=O)NSC=4N(C4CC4)C=3C=2)F)=C1 MIRPEVDMURQGBL-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
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- 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
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Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
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- A—HUMAN NECESSITIES
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- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
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- General Chemical & Material Sciences (AREA)
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- Endocrinology (AREA)
- Reproductive Health (AREA)
- Pulmonology (AREA)
- Gynecology & Obstetrics (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Farming Of Fish And Shellfish (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49465503P | 2003-08-12 | 2003-08-12 | |
| US60/494,655 | 2003-08-12 | ||
| PCT/US2004/025365 WO2005019228A1 (en) | 2003-08-12 | 2004-08-04 | Isothiazoloquinolones and related compounds as anti-infective agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2535370A1 CA2535370A1 (en) | 2005-03-03 |
| CA2535370C true CA2535370C (en) | 2011-01-25 |
Family
ID=34215887
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2535370A Expired - Fee Related CA2535370C (en) | 2003-08-12 | 2004-08-04 | Isothiazoloquinolones and related compounds as anti-infective agents |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20050075363A1 (https=) |
| EP (1) | EP1664062B1 (https=) |
| JP (1) | JP5147237B2 (https=) |
| KR (1) | KR20060069836A (https=) |
| CN (1) | CN1867570A (https=) |
| AU (1) | AU2004267052B2 (https=) |
| BR (1) | BRPI0413528A (https=) |
| CA (1) | CA2535370C (https=) |
| IL (1) | IL173492A0 (https=) |
| MX (1) | MXPA06001645A (https=) |
| NO (1) | NO20060653L (https=) |
| NZ (1) | NZ545157A (https=) |
| UA (1) | UA84879C2 (https=) |
| WO (1) | WO2005019228A1 (https=) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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| 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 |
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| 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 |
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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 |
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-
2004
- 2004-08-04 KR KR1020067002923A patent/KR20060069836A/ko not_active Ceased
- 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
- 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 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
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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
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004267052A1 (en) | 2005-03-03 |
| MXPA06001645A (es) | 2006-05-12 |
| NO20060653L (no) | 2006-03-13 |
| EP1664062B1 (en) | 2013-03-13 |
| JP5147237B2 (ja) | 2013-02-20 |
| JP2007502275A (ja) | 2007-02-08 |
| CN1867570A (zh) | 2006-11-22 |
| NZ545157A (en) | 2009-03-31 |
| WO2005019228A1 (en) | 2005-03-03 |
| US20050075363A1 (en) | 2005-04-07 |
| CA2535370A1 (en) | 2005-03-03 |
| US20110223132A1 (en) | 2011-09-15 |
| EP1664062A1 (en) | 2006-06-07 |
| KR20060069836A (ko) | 2006-06-22 |
| BRPI0413528A (pt) | 2006-10-10 |
| AU2004267052B2 (en) | 2009-02-05 |
| UA84879C2 (ru) | 2008-12-10 |
| IL173492A0 (en) | 2006-06-11 |
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