AU2010338267B2 - New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof - Google Patents
New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof Download PDFInfo
- Publication number
- AU2010338267B2 AU2010338267B2 AU2010338267A AU2010338267A AU2010338267B2 AU 2010338267 B2 AU2010338267 B2 AU 2010338267B2 AU 2010338267 A AU2010338267 A AU 2010338267A AU 2010338267 A AU2010338267 A AU 2010338267A AU 2010338267 B2 AU2010338267 B2 AU 2010338267B2
- Authority
- AU
- Australia
- Prior art keywords
- hydroxyquinolin
- methanone
- carboxamide
- hydroxy
- dihydroquinolin
- 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.)
- Ceased
Links
- FOXMISVOVQTSGS-UHFFFAOYSA-N 8-hydroxyquinoline-7-carboxamide Chemical group C1=CC=NC2=C(O)C(C(=O)N)=CC=C21 FOXMISVOVQTSGS-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 229940121375 antifungal agent Drugs 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims abstract description 8
- 239000003429 antifungal agent Substances 0.000 claims abstract description 7
- 241000222122 Candida albicans Species 0.000 claims abstract description 5
- 229940095731 candida albicans Drugs 0.000 claims abstract description 5
- 241000228245 Aspergillus niger Species 0.000 claims abstract description 4
- 241000825258 Scopulariopsis brevicaulis Species 0.000 claims abstract description 4
- 241000222126 [Candida] glabrata Species 0.000 claims abstract description 4
- 208000032343 candida glabrata infection Diseases 0.000 claims abstract description 4
- MYSWGUAQZAJSOK-UHFFFAOYSA-N ciprofloxacin Chemical compound C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 MYSWGUAQZAJSOK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000000034 method Methods 0.000 claims description 92
- -1 8-hydroxyquinolin-7-yl Chemical group 0.000 claims description 61
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 238000011282 treatment Methods 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 17
- 239000005864 Sulphur Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 239000001301 oxygen Substances 0.000 claims description 15
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 208000031888 Mycoses Diseases 0.000 claims description 13
- 150000003857 carboxamides Chemical class 0.000 claims description 13
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
- 206010017533 Fungal infection Diseases 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- VPDUYOQREPLCNA-UHFFFAOYSA-N 3,4,4a,5,6,7,8,8a-octahydro-1h-isoquinolin-2-yl-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CC2CCCCC2CN1C(=O)C1=C(O)C2=NC=CC=C2C=C1 VPDUYOQREPLCNA-UHFFFAOYSA-N 0.000 claims description 5
- VNTJOUTZMPCPDK-UHFFFAOYSA-N (7-fluoro-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CCC2=CC=C(F)C=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 VNTJOUTZMPCPDK-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- FULAAOORPDJGNY-UHFFFAOYSA-N (5,7-difluoro-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CCC2=C(F)C=C(F)C=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 FULAAOORPDJGNY-UHFFFAOYSA-N 0.000 claims description 3
- ZBAJIBVXDSAGBU-UHFFFAOYSA-N (6-fluoro-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CCC2=CC(F)=CC=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 ZBAJIBVXDSAGBU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- JVEGDLYMUJOLEL-UHFFFAOYSA-N 1,2,3,4,4a,4b,5,6,7,8,8a,9a-dodecahydrocarbazol-9-yl-(8-hydroxyquinolin-7-yl)methanone Chemical compound C12CCCCC2C2CCCCC2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 JVEGDLYMUJOLEL-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- LZXGGCMVEOIRLE-UHFFFAOYSA-N n-(4-bromophenyl)-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)C1=CC=C(Br)C=C1 LZXGGCMVEOIRLE-UHFFFAOYSA-N 0.000 claims description 3
- DALZZCVFSXIGAZ-UHFFFAOYSA-N n-[(4-chlorophenyl)methyl]-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)CC1=CC=C(Cl)C=C1 DALZZCVFSXIGAZ-UHFFFAOYSA-N 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims description 3
- QYWQCLPAQJHKFP-UHFFFAOYSA-N (6-bromo-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CCC2=CC(Br)=CC=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 QYWQCLPAQJHKFP-UHFFFAOYSA-N 0.000 claims description 2
- YCDBHYOFWHALBP-UHFFFAOYSA-N (6-chloro-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CCC2=CC(Cl)=CC=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 YCDBHYOFWHALBP-UHFFFAOYSA-N 0.000 claims description 2
- NKHFUOLJEVCICC-UHFFFAOYSA-N (8-hydroxyquinolin-7-yl)-(7-methyl-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound C1=CC=NC2=C(O)C(C(=O)N3CCCC4=CC=C(C=C43)C)=CC=C21 NKHFUOLJEVCICC-UHFFFAOYSA-N 0.000 claims description 2
- MCLYRJUITIDXLY-UHFFFAOYSA-N 2,3-dihydro-1,4-benzoxazin-4-yl-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1COC2=CC=CC=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 MCLYRJUITIDXLY-UHFFFAOYSA-N 0.000 claims description 2
- GGFUMFQBWPFPDP-UHFFFAOYSA-N 8-hydroxy-n-(4-methoxyphenyl)-n-methylquinoline-7-carboxamide Chemical compound C1=CC(OC)=CC=C1N(C)C(=O)C1=CC=C(C=CC=N2)C2=C1O GGFUMFQBWPFPDP-UHFFFAOYSA-N 0.000 claims description 2
- CCBBJNQJWATFRI-GFCCVEGCSA-N 8-hydroxy-n-[(1r)-1-phenylethyl]quinoline-7-carboxamide Chemical compound C1([C@H](NC(=O)C=2C(=C3N=CC=CC3=CC=2)O)C)=CC=CC=C1 CCBBJNQJWATFRI-GFCCVEGCSA-N 0.000 claims description 2
- MOHZXRNLUKZFBT-UHFFFAOYSA-N 8-hydroxy-n-methyl-n-(2-phenylethyl)quinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)CCC1=CC=CC=C1 MOHZXRNLUKZFBT-UHFFFAOYSA-N 0.000 claims description 2
- IUUXEYLGBMTUHO-ZDUSSCGKSA-N 8-hydroxy-n-methyl-n-[(1s)-1-phenylethyl]quinoline-7-carboxamide Chemical compound C1([C@@H](N(C)C(=O)C=2C(=C3N=CC=CC3=CC=2)O)C)=CC=CC=C1 IUUXEYLGBMTUHO-ZDUSSCGKSA-N 0.000 claims description 2
- RHQMMENSBKWQBL-UHFFFAOYSA-N 8-hydroxy-n-methyl-n-[[4-(2-phenylpropan-2-yl)phenyl]methyl]quinoline-2-carboxamide Chemical compound C=1C=C2C=CC=C(O)C2=NC=1C(=O)N(C)CC(C=C1)=CC=C1C(C)(C)C1=CC=CC=C1 RHQMMENSBKWQBL-UHFFFAOYSA-N 0.000 claims description 2
- YBQIPZBDCZCBJT-UHFFFAOYSA-N 8-hydroxy-n-methyl-n-propylquinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)N(C)CCC)=CC=C21 YBQIPZBDCZCBJT-UHFFFAOYSA-N 0.000 claims description 2
- KUJFCNJMTLANNY-UHFFFAOYSA-N 8-hydroxy-n-phenyl-n-propylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(CCC)C1=CC=CC=C1 KUJFCNJMTLANNY-UHFFFAOYSA-N 0.000 claims description 2
- 241001114451 Scopulariopsis candida Species 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000002538 fungal effect Effects 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- LCEDQNDDFOCWGG-UHFFFAOYSA-N morpholine-4-carbaldehyde Chemical compound O=CN1CCOCC1 LCEDQNDDFOCWGG-UHFFFAOYSA-N 0.000 claims description 2
- LXRVDCRNMWZPHR-UHFFFAOYSA-N n-(2-cyanoethyl)-n-(furan-2-ylmethyl)-8-hydroxyquinoline-7-carboxamide Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)N(CCC#N)CC1=CC=CO1 LXRVDCRNMWZPHR-UHFFFAOYSA-N 0.000 claims description 2
- VHOGKPRJHUHNKV-UHFFFAOYSA-N n-(4-chlorophenyl)-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)C1=CC=C(Cl)C=C1 VHOGKPRJHUHNKV-UHFFFAOYSA-N 0.000 claims description 2
- BKLAHUGTJMZOCG-UHFFFAOYSA-N n-(furan-2-ylmethyl)-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)CC1=CC=CO1 BKLAHUGTJMZOCG-UHFFFAOYSA-N 0.000 claims description 2
- NIJVZJOOOJXDRB-UHFFFAOYSA-N n-[(3-bromophenyl)methyl]-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)CC1=CC=CC(Br)=C1 NIJVZJOOOJXDRB-UHFFFAOYSA-N 0.000 claims description 2
- UCHPCORPSLOTNW-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)CC1=CC=C(F)C=C1 UCHPCORPSLOTNW-UHFFFAOYSA-N 0.000 claims description 2
- DRDJXHGBPLCNMC-UHFFFAOYSA-N n-benzyl-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)CC1=CC=CC=C1 DRDJXHGBPLCNMC-UHFFFAOYSA-N 0.000 claims description 2
- VOATUTGRQJASRW-UHFFFAOYSA-N n-cyclohexyl-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)C1CCCCC1 VOATUTGRQJASRW-UHFFFAOYSA-N 0.000 claims description 2
- LUHIFCDHQXUPFY-UHFFFAOYSA-N n-ethyl-8-hydroxy-n-methylquinoline-7-carboxamide Chemical compound C1=CC=NC2=C(O)C(C(=O)N(C)CC)=CC=C21 LUHIFCDHQXUPFY-UHFFFAOYSA-N 0.000 claims description 2
- HGRLNQHFZBWQKK-UHFFFAOYSA-N n-ethyl-8-hydroxy-n-phenylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(CC)C1=CC=CC=C1 HGRLNQHFZBWQKK-UHFFFAOYSA-N 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- CKJNUZNMWOVDFN-UHFFFAOYSA-N methanone Chemical compound O=[CH-] CKJNUZNMWOVDFN-UHFFFAOYSA-N 0.000 claims 35
- 125000005044 dihydroquinolinyl group Chemical class N1(CC=CC2=CC=CC=C12)* 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 3
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- JFCBYEPIECUPDF-UHFFFAOYSA-N (5-fluoro-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CCC2=C(F)C=CC=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 JFCBYEPIECUPDF-UHFFFAOYSA-N 0.000 claims 1
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
- ZVSDHCZKWDHFCQ-UHFFFAOYSA-N 8-hydroxy-n-methyl-n-phenylquinoline-7-carboxamide Chemical compound C=1C=C2C=CC=NC2=C(O)C=1C(=O)N(C)C1=CC=CC=C1 ZVSDHCZKWDHFCQ-UHFFFAOYSA-N 0.000 claims 1
- 229940053202 antiepileptics carboxamide derivative Drugs 0.000 abstract 1
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 59
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
- C07D491/113—Spiro-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09180902.0 | 2009-12-29 | ||
| EP09180902A EP2345643A1 (en) | 2009-12-29 | 2009-12-29 | New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof |
| PCT/EP2010/070790 WO2011080264A1 (en) | 2009-12-29 | 2010-12-28 | New tertiary 8-hydroxyquinoline-7-carboxamide derivatives and uses thereof |
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| AU2010338267A1 AU2010338267A1 (en) | 2012-07-19 |
| AU2010338267A2 AU2010338267A2 (en) | 2012-07-26 |
| AU2010338267B2 true AU2010338267B2 (en) | 2014-03-27 |
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| EP2345641A1 (en) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | New secondary 8-hydroxyquinoline-7-carboxamide derivatives |
| EP2345642A1 (en) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Secondary 8-hydroxyquinoline-7-carboxamide derivatives for use as antifungal agents |
| WO2013124335A1 (en) * | 2012-02-24 | 2013-08-29 | F. Hoffmann-La Roche Ag | Antiviral compounds |
| WO2014053315A1 (en) * | 2012-10-02 | 2014-04-10 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | Tetrahydroquinoline derivatives and their use as epac inhibitors |
| US8697753B1 (en) | 2013-02-07 | 2014-04-15 | Polichem Sa | Method of treating onychomycosis |
| WO2022066759A1 (en) | 2020-09-22 | 2022-03-31 | Milwaukee Electric Tool Corporation | Staple and staple collation |
| USD976093S1 (en) | 2020-09-22 | 2023-01-24 | Milwaukee Electric Tool Corporation | Staple collation |
| EP4237201A4 (en) | 2020-10-30 | 2024-12-11 | Milwaukee Electric Tool Corporation | POWERED FASTENER DRIVER |
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| US326330A (en) | 1885-09-15 | Harness-support | ||
| US326328A (en) | 1885-09-15 | Broiler | ||
| DE540842C (de) | 1930-08-06 | 1931-12-28 | Chinosol Fabrik Akt Ges | Verfahren zur Darstellung der 8-Acetyloxychinolin-7-carbonsaeure |
| HUP9801630A2 (hu) | 1995-04-08 | 1998-11-30 | Basf Aktiengesellschaft | Kinolinszármazékokból és citokróm B/C inhibitorokból készített szinergikus fungicid készítmények |
| WO1997017973A1 (en) * | 1995-11-13 | 1997-05-22 | Smithkline Beecham Corporation | Hemoregulatory compounds |
| AU4172197A (en) | 1996-09-10 | 1998-04-02 | Pharmacia & Upjohn Company | 8-hydroxy-7-substituted quinolines as anti-viral agents |
| ATE314347T1 (de) * | 1997-09-30 | 2006-01-15 | Daiichi Seiyaku Co | Sulfonylderivate |
| JP2001294572A (ja) * | 2000-02-09 | 2001-10-23 | Dai Ichi Seiyaku Co Ltd | 新規スルホニル誘導体 |
| ATE364385T1 (de) | 2000-10-12 | 2007-07-15 | Merck & Co Inc | Aza- und polyaza-naphthalenylcarbonsäureamide als hiv-integrase-hemmer |
| WO2002030931A2 (en) | 2000-10-12 | 2002-04-18 | Merck & Co., Inc. | Aza- and polyaza-naphthalenyl carboxamides useful as hiv integrase inhibitors |
| WO2002070486A1 (en) | 2001-03-01 | 2002-09-12 | Shionogi & Co., Ltd. | Nitrogen-containing heteroaryl compounds having hiv integrase inhibitory activity |
| AU2003257822A1 (en) | 2002-08-13 | 2004-04-30 | Shionogi And Co., Ltd. | Heterocyclic compound having hiv integrase inhibitory activity |
| EP1669348A4 (en) * | 2003-09-30 | 2009-03-11 | Eisai R&D Man Co Ltd | NEW ANTIPILIC AGENT CONTAINING A HETEROCYCLIC COMPOUND |
| FR2889192A1 (fr) * | 2005-07-27 | 2007-02-02 | Cytomics Systems Sa | Composes antifongiques, compositions contenant ces composes et leurs utilisations |
| EP2059305A2 (en) * | 2006-07-26 | 2009-05-20 | Novartis Ag | Inhibitors of undecaprenyl pyrophosphate synthase |
| WO2009140215A2 (en) * | 2008-05-11 | 2009-11-19 | Geraghty, Erin | Method for treating drug-resistant bacterial and other infections with clioquinol, phanquinone, and related compounds |
| EP2499139B1 (en) * | 2009-11-10 | 2013-12-11 | Pfizer Inc | N1-pyrazolospiroketone acetyl-coa carboxylase inhibitors |
| AR079529A1 (es) * | 2009-12-18 | 2012-02-01 | Incyte Corp | Derivados arilo y heteroarilo sustituidos y fundidos como inhibidores de la pi3k |
| EP2345641A1 (en) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | New secondary 8-hydroxyquinoline-7-carboxamide derivatives |
| EP2345642A1 (en) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Secondary 8-hydroxyquinoline-7-carboxamide derivatives for use as antifungal agents |
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2009
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