EA025563B1 - Новые третичные производные 8-оксихинолин-7-карбоксамида и их применение - Google Patents
Новые третичные производные 8-оксихинолин-7-карбоксамида и их применение Download PDFInfo
- Publication number
- EA025563B1 EA025563B1 EA201270670A EA201270670A EA025563B1 EA 025563 B1 EA025563 B1 EA 025563B1 EA 201270670 A EA201270670 A EA 201270670A EA 201270670 A EA201270670 A EA 201270670A EA 025563 B1 EA025563 B1 EA 025563B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- methanone
- hydroxyquinolin
- carboxamide
- hydroxy
- alkyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 229940121375 antifungal agent Drugs 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 239000003429 antifungal agent Substances 0.000 claims abstract description 7
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 38
- -1 (tetrahydrofuran-2-yl) methyl Chemical group 0.000 claims description 33
- 206010017533 Fungal infection Diseases 0.000 claims description 22
- 208000031888 Mycoses Diseases 0.000 claims description 21
- 125000005842 heteroatom Chemical group 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 229920006395 saturated elastomer Polymers 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 229910052717 sulfur Chemical group 0.000 claims description 15
- 238000011282 treatment Methods 0.000 claims description 15
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 239000011593 sulfur Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 239000001301 oxygen Substances 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
- 239000013256 coordination polymer Substances 0.000 claims description 8
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 239000004305 biphenyl Substances 0.000 claims description 7
- 235000010290 biphenyl Nutrition 0.000 claims description 7
- 125000002950 monocyclic group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- MMCIXNVRVDTQSG-UHFFFAOYSA-N quinoline-7-carboxamide Chemical compound C1=CC=NC2=CC(C(=O)N)=CC=C21 MMCIXNVRVDTQSG-UHFFFAOYSA-N 0.000 claims description 6
- ZVPNBKXLAIQXAQ-UHFFFAOYSA-N (4-tert-butylpiperidin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CC(C(C)(C)C)CCN1C(=O)C1=CC=C(C=CC=N2)C2=C1O ZVPNBKXLAIQXAQ-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 5
- IDWAIJVQGCLRDV-UHFFFAOYSA-N 1,3-dihydroisoindol-2-yl-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1C2=CC=CC=C2CN1C(=O)C1=C(O)C2=NC=CC=C2C=C1 IDWAIJVQGCLRDV-UHFFFAOYSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 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 4
- 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 4
- HGNLFMRNEFPDHZ-UHFFFAOYSA-N 8-hydroxyquinoline-7-carbaldehyde Chemical compound C1=CN=C2C(O)=C(C=O)C=CC2=C1 HGNLFMRNEFPDHZ-UHFFFAOYSA-N 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 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
- OKZBWZJACNHVMU-UHFFFAOYSA-N (5-bromo-8-hydroxyquinolin-7-yl)-(1,3-dihydroisoindol-2-yl)methanone Chemical compound C1C2=CC=CC=C2CN1C(=O)C1=C(O)C2=NC=CC=C2C(Br)=C1 OKZBWZJACNHVMU-UHFFFAOYSA-N 0.000 claims description 3
- AGGWISYPIUAOIZ-UHFFFAOYSA-N (5-chloro-8-hydroxy-3,4-dihydro-2h-quinolin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1=CC=NC2=C(O)C(C(=O)N3CCCC=4C(Cl)=CC=C(C3=4)O)=CC=C21 AGGWISYPIUAOIZ-UHFFFAOYSA-N 0.000 claims description 3
- 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 description 3
- 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 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
- 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 3
- 125000006280 2-bromobenzyl group Chemical group [H]C1=C([H])C(Br)=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006279 3-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Br)=C1[H])C([H])([H])* 0.000 claims description 3
- 125000006281 4-bromobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Br)C([H])([H])* 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 3
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 3
- 150000001924 cycloalkanes Chemical group 0.000 claims description 3
- 125000005044 dihydroquinolinyl group Chemical class N1(CC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 238000011321 prophylaxis Methods 0.000 claims description 3
- OSEHHHGBHHTENC-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1=CC2=CC=CN=C2C(O)=C1C(=O)N1CCS(=O)(=O)CC1 OSEHHHGBHHTENC-UHFFFAOYSA-N 0.000 claims description 2
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- KODXYKOCOVZOMP-UHFFFAOYSA-N (3,3-dimethylpiperidin-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1C(C)(C)CCCN1C(=O)C1=CC=C(C=CC=N2)C2=C1O KODXYKOCOVZOMP-UHFFFAOYSA-N 0.000 claims description 2
- SCOBWEANUXAFAR-UHFFFAOYSA-N (5-bromo-2,3-dihydroindol-1-yl)-(8-hydroxyquinolin-7-yl)methanone Chemical compound C1CC2=CC(Br)=CC=C2N1C(=O)C1=C(O)C2=NC=CC=C2C=C1 SCOBWEANUXAFAR-UHFFFAOYSA-N 0.000 claims description 2
- 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
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- FLCUQKVWAFMYFX-UHFFFAOYSA-N (8-hydroxyquinolin-7-yl)-(2-methylpiperidin-1-yl)methanone Chemical compound CC1CCCCN1C(=O)C1=CC=C(C=CC=N2)C2=C1O FLCUQKVWAFMYFX-UHFFFAOYSA-N 0.000 claims description 2
- CDHOHSRQJKGXJR-UHFFFAOYSA-N (8-hydroxyquinolin-7-yl)-(2-methylpyrrolidin-1-yl)methanone Chemical compound CC1CCCN1C(=O)C1=CC=C(C=CC=N2)C2=C1O CDHOHSRQJKGXJR-UHFFFAOYSA-N 0.000 claims description 2
- CRVDQFZTXZGOCM-UHFFFAOYSA-N (8-hydroxyquinolin-7-yl)-(3-methyl-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound C12=CC=CC=C2CC(C)CN1C(=O)C1=CC=C(C=CC=N2)C2=C1O CRVDQFZTXZGOCM-UHFFFAOYSA-N 0.000 claims description 2
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- CVQRPSDXCSJKJD-UHFFFAOYSA-N (8-hydroxyquinolin-7-yl)-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)methanone Chemical compound C1=CC=NC2=C(O)C(C(=O)N3C4=CC=C(C=C4CCC3)C)=CC=C21 CVQRPSDXCSJKJD-UHFFFAOYSA-N 0.000 claims description 2
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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
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- 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 (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201270670A1 EA201270670A1 (ru) | 2013-03-29 |
| EA025563B1 true EA025563B1 (ru) | 2017-01-30 |
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| Application Number | Title | Priority Date | Filing Date |
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| EA201270670A EA025563B1 (ru) | 2009-12-29 | 2010-12-28 | Новые третичные производные 8-оксихинолин-7-карбоксамида и их применение |
Country Status (37)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2345642A1 (en) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | Secondary 8-hydroxyquinoline-7-carboxamide derivatives for use as antifungal agents |
| EP2345641A1 (en) * | 2009-12-29 | 2011-07-20 | Polichem S.A. | New secondary 8-hydroxyquinoline-7-carboxamide derivatives |
| CN104185624B (zh) * | 2012-02-24 | 2016-10-12 | 弗·哈夫曼-拉罗切有限公司 | 抗病毒化合物 |
| ES2749512T3 (es) | 2012-10-02 | 2020-03-20 | Inst Nat Sante Rech Med | Derivados de tetrahidroquinolina y su uso como inhibidores de Epac |
| US8697753B1 (en) | 2013-02-07 | 2014-04-15 | Polichem Sa | Method of treating onychomycosis |
| USD976093S1 (en) | 2020-09-22 | 2023-01-24 | Milwaukee Electric Tool Corporation | Staple collation |
| CN220302508U (zh) | 2020-09-22 | 2024-01-05 | 米沃奇电动工具公司 | 动力式紧固件驱动器及钉排 |
| WO2022094190A2 (en) | 2020-10-30 | 2022-05-05 | Milwaukee Electric Tool Corporation | Powered fastener driver |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998011073A1 (en) * | 1996-09-10 | 1998-03-19 | Pharmacia & Upjohn Company | 8-hydroxy-7-substituted quinolines as anti-viral agents |
| US6194413B1 (en) * | 1995-11-13 | 2001-02-27 | Smithkline Beecham Corporation | Hemoregulatory compounds |
| US6525042B1 (en) * | 1997-09-30 | 2003-02-25 | Daiichi Pharmaceutical Co., Ltd. | Sulfonyl derivatives |
| EP1669348A1 (en) * | 2003-09-30 | 2006-06-14 | Eisai Co., Ltd. | Novel antifungal agent comprising heterocyclic compound |
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| US326328A (en) | 1885-09-15 | Broiler | ||
| US326330A (en) | 1885-09-15 | Harness-support | ||
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