MXPA06001645A - Isotiazoloquinolonas y compuestos relacionados como agentes anti-infecciosos. - Google Patents
Isotiazoloquinolonas y compuestos relacionados como agentes anti-infecciosos.Info
- Publication number
- MXPA06001645A MXPA06001645A MXPA06001645A MXPA06001645A MXPA06001645A MX PA06001645 A MXPA06001645 A MX PA06001645A MX PA06001645 A MXPA06001645 A MX PA06001645A MX PA06001645 A MXPA06001645 A MX PA06001645A MX PA06001645 A MXPA06001645 A MX PA06001645A
- Authority
- MX
- Mexico
- Prior art keywords
- cyclopropyl
- fluoro
- dione
- isothiazolo
- phenyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 289
- 239000004599 antimicrobial Substances 0.000 title description 11
- 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 122
- 239000000203 mixture Substances 0.000 claims abstract description 101
- 238000000034 method Methods 0.000 claims abstract description 44
- 208000015181 infectious disease Diseases 0.000 claims abstract description 43
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 22
- 241001465754 Metazoa Species 0.000 claims abstract description 21
- 239000013543 active substance Substances 0.000 claims abstract description 13
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract description 13
- 230000001580 bacterial effect Effects 0.000 claims abstract description 11
- 239000003085 diluting agent Substances 0.000 claims abstract description 10
- -1 or R2 is Ci-C8alkyl Chemical group 0.000 claims description 380
- 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 174
- 125000000217 alkyl group Chemical group 0.000 claims description 93
- 125000001424 substituent group Chemical group 0.000 claims description 88
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 84
- 125000003118 aryl group Chemical group 0.000 claims description 83
- 229910052736 halogen Inorganic materials 0.000 claims description 81
- 150000002367 halogens Chemical class 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 74
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 66
- 125000003282 alkyl amino group Chemical group 0.000 claims description 60
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 48
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 46
- 229910052799 carbon Inorganic materials 0.000 claims description 42
- 125000004076 pyridyl group Chemical group 0.000 claims description 41
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 37
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 33
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 125000001544 thienyl group Chemical group 0.000 claims description 32
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
- 229920006395 saturated elastomer Polymers 0.000 claims description 30
- 125000003386 piperidinyl group Chemical group 0.000 claims description 28
- 150000002148 esters Chemical class 0.000 claims description 24
- 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
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 125000002541 furyl group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 125000004193 piperazinyl group Chemical group 0.000 claims description 21
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 21
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 19
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 125000002757 morpholinyl group Chemical group 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 19
- 125000004043 oxo group Chemical group O=* 0.000 claims description 19
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 19
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 19
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 18
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 18
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 18
- 125000002883 imidazolyl group Chemical group 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
- 244000005700 microbiome Species 0.000 claims description 17
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 16
- 150000001721 carbon Chemical group 0.000 claims description 16
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 16
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 14
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 14
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 13
- 125000000623 heterocyclic group Chemical group 0.000 claims description 13
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 125000004611 dihydroisoindolyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 12
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 12
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 12
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 11
- 241000588724 Escherichia coli Species 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 230000000844 anti-bacterial effect Effects 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 10
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 10
- 125000006536 (C1-C2)alkoxy group Chemical group 0.000 claims description 9
- 208000035143 Bacterial infection Diseases 0.000 claims description 9
- 101150020251 NR13 gene Proteins 0.000 claims description 9
- 125000004429 atom Chemical group 0.000 claims description 9
- 208000022362 bacterial infectious disease Diseases 0.000 claims description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 8
- 241000124008 Mammalia Species 0.000 claims description 8
- 239000003937 drug carrier Substances 0.000 claims description 8
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 239000006188 syrup Substances 0.000 claims description 8
- 235000020357 syrup Nutrition 0.000 claims description 8
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 claims description 7
- 229940121375 antifungal agent Drugs 0.000 claims description 7
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 7
- 125000002619 bicyclic group Chemical group 0.000 claims description 7
- 239000006071 cream Substances 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 241000894006 Bacteria Species 0.000 claims description 6
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 6
- 241000606161 Chlamydia Species 0.000 claims description 6
- 239000003429 antifungal agent Substances 0.000 claims description 6
- 239000003443 antiviral agent Substances 0.000 claims description 6
- 125000001246 bromo group Chemical group Br* 0.000 claims description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 6
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 6
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 6
- 241000251468 Actinopterygii Species 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003242 anti bacterial agent Substances 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 239000002775 capsule Substances 0.000 claims description 5
- 125000006582 (C5-C6) heterocycloalkyl group Chemical group 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 102000014150 Interferons Human genes 0.000 claims description 4
- 108010050904 Interferons Proteins 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 239000003781 beta lactamase inhibitor Substances 0.000 claims description 4
- 229940126813 beta-lactamase inhibitor Drugs 0.000 claims description 4
- 229940079322 interferon Drugs 0.000 claims description 4
- 239000001301 oxygen Substances 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
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 4
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims description 4
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 3
- 206010035664 Pneumonia Diseases 0.000 claims description 3
- 206010037075 Protozoal infections Diseases 0.000 claims description 3
- 239000000443 aerosol Substances 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940054534 ophthalmic solution Drugs 0.000 claims description 3
- 239000002997 ophthalmic solution Substances 0.000 claims description 3
- 208000000143 urethritis Diseases 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
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])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
- 206010001076 Acute sinusitis Diseases 0.000 claims description 2
- 206010012742 Diarrhoea infectious Diseases 0.000 claims description 2
- 206010061977 Genital infection female Diseases 0.000 claims description 2
- 208000036209 Intraabdominal Infections 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
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 206010006451 bronchitis Diseases 0.000 claims description 2
- CBGUOGMQLZIXBE-XGQKBEPLSA-N clobetasol propionate Chemical compound C1CC2=CC(=O)C=C[C@]2(C)[C@]2(F)[C@@H]1[C@@H]1C[C@H](C)[C@@](C(=O)CCl)(OC(=O)CC)[C@@]1(C)C[C@@H]2O CBGUOGMQLZIXBE-XGQKBEPLSA-N 0.000 claims description 2
- 208000001848 dysentery Diseases 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 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
- 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
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- 201000008297 typhoid fever Diseases 0.000 claims description 2
- 208000019206 urinary tract infection Diseases 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 claims 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims 2
- 125000001589 carboacyl group Chemical group 0.000 claims 2
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 claims 2
- MDGXQGMSNOEFRL-UHFFFAOYSA-N quinoline-3,4-dione;hydrochloride Chemical compound Cl.C1=CC=C2C(=O)C(=O)C=NC2=C1 MDGXQGMSNOEFRL-UHFFFAOYSA-N 0.000 claims 2
- 229920002554 vinyl polymer Polymers 0.000 claims 2
- KLIDCXVFHGNTTM-UHFFFAOYSA-N 2,6-dimethoxyphenol Chemical group COC1=CC=CC(OC)=C1O KLIDCXVFHGNTTM-UHFFFAOYSA-N 0.000 claims 1
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-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
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 1
- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- 125000000389 2-pyrrolyl group Chemical group [H]N1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- GQOJGBVTUSRBPQ-UHFFFAOYSA-N 2-quinolin-3-ylacetic acid Chemical compound C1=CC=CC2=CC(CC(=O)O)=CN=C21 GQOJGBVTUSRBPQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims 1
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 1
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 1
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims 1
- BAYGVMXZJBFEMB-UHFFFAOYSA-N 4-(trifluoromethyl)phenol Chemical compound OC1=CC=C(C(F)(F)F)C=C1 BAYGVMXZJBFEMB-UHFFFAOYSA-N 0.000 claims 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims 1
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims 1
- 125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 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
- XXWBBUTXZUJGJY-UHFFFAOYSA-N 9-cyclopropyl-6-fluoro-3,4-dioxo-n-phenyl-[1,2]thiazolo[5,4-b]quinoline-7-carboxamide Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(=O)NC1=CC=CC=C1 XXWBBUTXZUJGJY-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
- 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
- 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
- WBWUYPBFCIMNRV-UHFFFAOYSA-N 9-cyclopropyl-8-(difluoromethoxy)-7-(3-methyl-2,3-dihydro-1h-isoindol-5-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound C1=C2C(C)NCC2=CC=C1C(C=1OC(F)F)=CC=C(C(C=2C(=O)NSC=22)=O)C=1N2C1CC1 WBWUYPBFCIMNRV-UHFFFAOYSA-N 0.000 claims 1
- VACGDJABSZROER-UHFFFAOYSA-N 9-cyclopropyl-8-methoxy-7-(2-methylpyridin-3-yl)-[1,2]thiazolo[5,4-b]quinoline-3,4-dione Chemical compound COC1=C(C=2C(=NC=CC=2)C)C=CC(C(C=2C(=O)NSC=22)=O)=C1N2C1CC1 VACGDJABSZROER-UHFFFAOYSA-N 0.000 claims 1
- 241000478345 Afer Species 0.000 claims 1
- 239000005711 Benzoic acid Substances 0.000 claims 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- 208000010362 Protozoan Infections Diseases 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims 1
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- IUEPRJYNLFJEBW-UHFFFAOYSA-N piperazin-1-yl 9-cyclopropyl-6-fluoro-3,4-dioxo-[1,2]thiazolo[5,4-b]quinoline-7-carboxylate Chemical compound FC1=CC(C(C=2C(=O)NSC=2N2C3CC3)=O)=C2C=C1C(=O)ON1CCNCC1 IUEPRJYNLFJEBW-UHFFFAOYSA-N 0.000 claims 1
- 229940080818 propionamide Drugs 0.000 claims 1
- 201000007094 prostatitis Diseases 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- A—HUMAN NECESSITIES
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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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
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- Engineering & Computer Science (AREA)
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- Urology & Nephrology (AREA)
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- Tropical Medicine & Parasitology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Gynecology & Obstetrics (AREA)
- Virology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Farming Of Fish And Shellfish (AREA)
- Medicinal Preparation (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US49465503P | 2003-08-12 | 2003-08-12 | |
| PCT/US2004/025365 WO2005019228A1 (en) | 2003-08-12 | 2004-08-04 | Isothiazoloquinolones and related compounds as anti-infective agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA06001645A true MXPA06001645A (es) | 2006-05-12 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA06001645A MXPA06001645A (es) | 2003-08-12 | 2004-08-04 | Isotiazoloquinolonas y compuestos relacionados como agentes anti-infecciosos. |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US20050075363A1 (enExample) |
| EP (1) | EP1664062B1 (enExample) |
| JP (1) | JP5147237B2 (enExample) |
| KR (1) | KR20060069836A (enExample) |
| CN (1) | CN1867570A (enExample) |
| AU (1) | AU2004267052B2 (enExample) |
| BR (1) | BRPI0413528A (enExample) |
| CA (1) | CA2535370C (enExample) |
| IL (1) | IL173492A0 (enExample) |
| MX (1) | MXPA06001645A (enExample) |
| NO (1) | NO20060653L (enExample) |
| NZ (1) | NZ545157A (enExample) |
| UA (1) | UA84879C2 (enExample) |
| WO (1) | WO2005019228A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006089054A1 (en) * | 2005-02-16 | 2006-08-24 | Achillion Pharmaceuticals, Inc. | New isothiazoloquinolones and related compounds as anti-infective agents |
| 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 |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US4767762A (en) * | 1985-12-23 | 1988-08-30 | Abbott Laboratories | Tricyclic quinoline and naphthyride antibacterials |
| 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 |
| WO2006089054A1 (en) * | 2005-02-16 | 2006-08-24 | Achillion Pharmaceuticals, Inc. | New isothiazoloquinolones and related compounds as anti-infective agents |
| US7678235B2 (en) * | 2005-10-19 | 2010-03-16 | Sylvan Source, Inc. | Water purification system |
-
2004
- 2004-08-04 KR KR1020067002923A patent/KR20060069836A/ko not_active Ceased
- 2004-08-04 NZ NZ545157A patent/NZ545157A/en not_active IP Right Cessation
- 2004-08-04 AU AU2004267052A patent/AU2004267052B2/en not_active Ceased
- 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 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
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007502275A (ja) | 2007-02-08 |
| US20110223132A1 (en) | 2011-09-15 |
| AU2004267052B2 (en) | 2009-02-05 |
| EP1664062A1 (en) | 2006-06-07 |
| KR20060069836A (ko) | 2006-06-22 |
| WO2005019228A1 (en) | 2005-03-03 |
| IL173492A0 (en) | 2006-06-11 |
| US20050075363A1 (en) | 2005-04-07 |
| UA84879C2 (ru) | 2008-12-10 |
| EP1664062B1 (en) | 2013-03-13 |
| JP5147237B2 (ja) | 2013-02-20 |
| CN1867570A (zh) | 2006-11-22 |
| CA2535370A1 (en) | 2005-03-03 |
| BRPI0413528A (pt) | 2006-10-10 |
| AU2004267052A1 (en) | 2005-03-03 |
| CA2535370C (en) | 2011-01-25 |
| NZ545157A (en) | 2009-03-31 |
| NO20060653L (no) | 2006-03-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FA | Abandonment or withdrawal |