ES2298806T3 - Derivados de 4-aminoquinolina-3-carboxamida como inhibidores de pde4. - Google Patents
Derivados de 4-aminoquinolina-3-carboxamida como inhibidores de pde4. Download PDFInfo
- Publication number
- ES2298806T3 ES2298806T3 ES04765656T ES04765656T ES2298806T3 ES 2298806 T3 ES2298806 T3 ES 2298806T3 ES 04765656 T ES04765656 T ES 04765656T ES 04765656 T ES04765656 T ES 04765656T ES 2298806 T3 ES2298806 T3 ES 2298806T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- quad
- optionally substituted
- alkoxy
- sulfonyl
- 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 - Lifetime
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 11
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 159
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 94
- -1 C1-6-CO- alkoxy Chemical group 0.000 claims abstract description 59
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 58
- 239000001257 hydrogen Substances 0.000 claims abstract description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 50
- 150000003839 salts Chemical class 0.000 claims abstract description 47
- 125000003118 aryl group Chemical group 0.000 claims abstract description 40
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 40
- 125000001424 substituent group Chemical group 0.000 claims abstract description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 34
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 29
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 28
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 25
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 150000002367 halogens Chemical class 0.000 claims abstract description 16
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 15
- 239000001301 oxygen Substances 0.000 claims abstract description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 11
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- 125000002950 monocyclic group Chemical group 0.000 claims abstract description 8
- 229910052717 sulfur Chemical group 0.000 claims abstract description 8
- 239000011593 sulfur Chemical group 0.000 claims abstract description 8
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 7
- 239000011737 fluorine Substances 0.000 claims abstract description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 26
- 238000011282 treatment Methods 0.000 claims description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 238000011321 prophylaxis Methods 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 5
- 230000000172 allergic effect Effects 0.000 claims description 4
- 208000010668 atopic eczema Diseases 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 230000000699 topical effect Effects 0.000 claims description 4
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims description 3
- YBYWZPBPJMHJAV-UHFFFAOYSA-N 4-(3-chloroanilino)-8-methyl-6-morpholin-4-ylsulfonylquinoline-3-carboxamide Chemical compound NC(=O)C1=CN=C2C(C)=CC(S(=O)(=O)N3CCOCC3)=CC2=C1NC1=CC=CC(Cl)=C1 YBYWZPBPJMHJAV-UHFFFAOYSA-N 0.000 claims description 3
- BGNVJYIGOWOUFY-UHFFFAOYSA-N 4-(4-fluoro-3-methoxyanilino)-8-methyl-6-morpholin-4-ylsulfonylquinoline-3-carboxamide Chemical compound C1=C(F)C(OC)=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)N2CCOCC2)=C1 BGNVJYIGOWOUFY-UHFFFAOYSA-N 0.000 claims description 3
- HNQXUZRWWFMUPY-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)sulfonyl-4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methylquinoline-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1S(=O)(=O)C1=CC(C)=C(N=CC(C(N)=O)=C2NC=3C=4CCOC=4C=CC=3)C2=C1 HNQXUZRWWFMUPY-UHFFFAOYSA-N 0.000 claims description 3
- ZUGAIJHWGUPKJR-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)sulfonyl-4-(2,3-dihydro-1-benzofuran-4-ylamino)quinoline-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1S(=O)(=O)C1=CC=C(N=CC(C(N)=O)=C2NC=3C=4CCOC=4C=CC=3)C2=C1 ZUGAIJHWGUPKJR-UHFFFAOYSA-N 0.000 claims description 3
- FMAZIEOCCREEFM-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)sulfonyl-4-(4-fluoro-3-methoxyanilino)-8-methylquinoline-3-carboxamide Chemical compound C1=C(F)C(OC)=CC(NC=2C3=CC(=CC(C)=C3N=CC=2C(N)=O)S(=O)(=O)N2CCN(CC2)C(C)=O)=C1 FMAZIEOCCREEFM-UHFFFAOYSA-N 0.000 claims description 3
- GVLLHJCWEHGPJS-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)sulfonyl-4-(4-fluoro-3-methoxyanilino)quinoline-3-carboxamide Chemical compound C1=C(F)C(OC)=CC(NC=2C3=CC(=CC=C3N=CC=2C(N)=O)S(=O)(=O)N2CCN(CC2)C(C)=O)=C1 GVLLHJCWEHGPJS-UHFFFAOYSA-N 0.000 claims description 3
- MVLHEBMREULBJY-UHFFFAOYSA-N 6-(4-acetylpiperazin-1-yl)sulfonyl-8-methyl-4-(3-methylanilino)quinoline-3-carboxamide Chemical compound C1CN(C(=O)C)CCN1S(=O)(=O)C1=CC(C)=C(N=CC(C(N)=O)=C2NC=3C=C(C)C=CC=3)C2=C1 MVLHEBMREULBJY-UHFFFAOYSA-N 0.000 claims description 3
- KTWNHRINTSYKIH-UHFFFAOYSA-N 8-methyl-4-[(1-methylindazol-6-yl)amino]-6-morpholin-4-ylsulfonylquinoline-3-carboxamide Chemical compound C=1C2=C(NC=3C=C4N(C)N=CC4=CC=3)C(C(N)=O)=CN=C2C(C)=CC=1S(=O)(=O)N1CCOCC1 KTWNHRINTSYKIH-UHFFFAOYSA-N 0.000 claims description 3
- 230000002757 inflammatory effect Effects 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- SVHWATQQUBHLTA-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-(4-methylsulfonylpiperazin-1-yl)sulfonylquinoline-3-carboxamide Chemical compound C1CN(S(=O)(=O)C)CCN1S(=O)(=O)C1=CC=C(N=CC(C(N)=O)=C2NC=3C=4CCOC=4C=CC=3)C2=C1 SVHWATQQUBHLTA-UHFFFAOYSA-N 0.000 claims description 2
- CNJOZWLBJKDGTN-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-(4-pyrazin-2-ylpiperazin-1-yl)sulfonylquinoline-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(=O)N)=CN=C2C=CC=1S(=O)(=O)N(CC1)CCN1C1=CN=CC=N1 CNJOZWLBJKDGTN-UHFFFAOYSA-N 0.000 claims description 2
- IDOIGAZVLFBSBX-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-(dimethylsulfamoyl)quinoline-3-carboxamide Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2N=CC(C(N)=O)=C1NC1=CC=CC2=C1CCO2 IDOIGAZVLFBSBX-UHFFFAOYSA-N 0.000 claims description 2
- VAWSWUOYVGGZAY-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-(oxan-4-ylsulfamoyl)quinoline-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(=O)N)=CN=C2C=CC=1S(=O)(=O)NC1CCOCC1 VAWSWUOYVGGZAY-UHFFFAOYSA-N 0.000 claims description 2
- FVBQZKXPVXGFOC-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-[4-(dimethylamino)piperidin-1-yl]sulfonylquinoline-3-carboxamide Chemical compound C1CC(N(C)C)CCN1S(=O)(=O)C1=CC=C(N=CC(C(N)=O)=C2NC=3C=4CCOC=4C=CC=3)C2=C1 FVBQZKXPVXGFOC-UHFFFAOYSA-N 0.000 claims description 2
- HBQBEDGJAGBZBO-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-morpholin-4-ylsulfonylquinoline-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(=O)N)=CN=C2C=CC=1S(=O)(=O)N1CCOCC1 HBQBEDGJAGBZBO-UHFFFAOYSA-N 0.000 claims description 2
- KQSMKFLODLYFCM-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-8-methyl-6-morpholin-4-ylsulfonylquinoline-3-carboxamide Chemical compound C=1C2=C(NC=3C=4CCOC=4C=CC=3)C(C(N)=O)=CN=C2C(C)=CC=1S(=O)(=O)N1CCOCC1 KQSMKFLODLYFCM-UHFFFAOYSA-N 0.000 claims description 2
- ICVSVGLRXAUBRS-UHFFFAOYSA-N 4-(3-cyanoanilino)-8-methyl-6-morpholin-4-ylsulfonylquinoline-3-carboxamide Chemical compound NC(=O)C1=CN=C2C(C)=CC(S(=O)(=O)N3CCOCC3)=CC2=C1NC1=CC=CC(C#N)=C1 ICVSVGLRXAUBRS-UHFFFAOYSA-N 0.000 claims description 2
- WKVXXUZTBQURHS-UHFFFAOYSA-N 6-(dimethylsulfamoyl)-4-(3-methoxyanilino)quinoline-3-carboxamide Chemical compound COC1=CC=CC(NC=2C3=CC(=CC=C3N=CC=2C(N)=O)S(=O)(=O)N(C)C)=C1 WKVXXUZTBQURHS-UHFFFAOYSA-N 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- XDWZYBSRANUFJF-UHFFFAOYSA-N 4-(2,3-dihydro-1-benzofuran-4-ylamino)-6-[4-(dimethylcarbamoyl)piperazin-1-yl]sulfonylquinoline-3-carboxamide Chemical compound C1CN(C(=O)N(C)C)CCN1S(=O)(=O)C1=CC=C(N=CC(C(N)=O)=C2NC=3C=4CCOC=4C=CC=3)C2=C1 XDWZYBSRANUFJF-UHFFFAOYSA-N 0.000 claims 1
- PUVGOARSSXJLJM-UHFFFAOYSA-N 4-(4-fluoro-3-methoxyanilino)-6-(4-methylsulfonylpiperazin-1-yl)sulfonylquinoline-3-carboxamide Chemical compound C1=C(F)C(OC)=CC(NC=2C3=CC(=CC=C3N=CC=2C(N)=O)S(=O)(=O)N2CCN(CC2)S(C)(=O)=O)=C1 PUVGOARSSXJLJM-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- 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
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- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
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- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/622—Forming processes; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/626—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B
- C04B35/63—Preparing or treating the powders individually or as batches ; preparing or treating macroscopic reinforcing agents for ceramic products, e.g. fibres; mechanical aspects section B using additives specially adapted for forming the products, e.g.. binder binders
- C04B35/632—Organic additives
-
- 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
-
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- 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
- C07D405/14—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 three or more hetero rings
Landscapes
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
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- Neurology (AREA)
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- Ceramic Engineering (AREA)
- Manufacturing & Machinery (AREA)
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- Dermatology (AREA)
- Immunology (AREA)
- Inorganic Chemistry (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
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- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
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- Vascular Medicine (AREA)
- Ophthalmology & Optometry (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0322722.0A GB0322722D0 (en) | 2003-09-27 | 2003-09-27 | Compounds |
| GB0322722 | 2003-09-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2298806T3 true ES2298806T3 (es) | 2008-05-16 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04765656T Expired - Lifetime ES2298806T3 (es) | 2003-09-27 | 2004-09-23 | Derivados de 4-aminoquinolina-3-carboxamida como inhibidores de pde4. |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US20080096884A1 (OSRAM) |
| EP (1) | EP1673086B1 (OSRAM) |
| JP (1) | JP2007506703A (OSRAM) |
| AR (1) | AR045824A1 (OSRAM) |
| AT (1) | ATE384530T1 (OSRAM) |
| DE (1) | DE602004011548T2 (OSRAM) |
| ES (1) | ES2298806T3 (OSRAM) |
| GB (1) | GB0322722D0 (OSRAM) |
| TW (1) | TW200526584A (OSRAM) |
| WO (1) | WO2005030212A1 (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI328009B (en) * | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| GB0605462D0 (en) * | 2006-03-17 | 2006-04-26 | Glaxo Group Ltd | Novel compounds |
| WO2008052734A1 (en) | 2006-10-30 | 2008-05-08 | Novartis Ag | Heterocyclic compounds as antiinflammatory agents |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| EP2379076B1 (en) * | 2008-12-23 | 2014-11-12 | The Trustees of Columbia University in the City of New York | Phosphodiesterase inhibitors and uses thereof |
| WO2010097248A1 (en) | 2009-01-13 | 2010-09-02 | Glaxo Group Limited | Pyrimidinecarboxamide derivatives as inhibitors of syk kinase |
| US8367829B2 (en) | 2010-05-10 | 2013-02-05 | Gilead Sciences, Inc. | Bi-functional pyrazolopyridine compounds |
| US8394829B2 (en) | 2010-05-10 | 2013-03-12 | Gilead Sciences, Inc. | Bi-functional quinoline analogs |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| CA2828219A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Pyrazolo [1,5-a] pyridines as trk inhibitors |
| BR112015019276A2 (pt) | 2013-02-19 | 2017-07-18 | Pfizer | compostos de azabenzimidazol como inibidores de isoenzimas de pde4 para o tratamento de distúrbios do snc e outros distúrbios |
| US10131669B2 (en) | 2014-07-24 | 2018-11-20 | Pfizer Inc. | Pyrazolopyrimidine compounds |
| EA031201B1 (ru) | 2014-08-06 | 2018-11-30 | Пфайзер Инк. | Соединения имидазопиридазина |
| MA41140A (fr) | 2014-12-12 | 2017-10-17 | Cancer Research Tech Ltd | Dérivés de 2,4-dioxo-quinazoline-6-sulfonamide en tant qu'inhibiteurs de la parg |
| MA41179A (fr) | 2014-12-19 | 2017-10-24 | Cancer Research Tech Ltd | Composés inhibiteurs de parg |
| BR112018006873A2 (pt) | 2015-10-05 | 2018-11-06 | The Trustees Of Columbia University In The City Of New York | ativadores do fluxo autofágico e fosfolipase d e depuração de agregados de proteína incluindo tau e tratamento de proteinopatias |
| TW202345809A (zh) | 2022-03-23 | 2023-12-01 | 美商愛德亞生物科學公司 | 作為parg抑制劑之經哌取代的吲唑化合物 |
| TW202430172A (zh) * | 2023-01-17 | 2024-08-01 | 大陸商瑞石生物醫藥有限公司 | Ｐｄｅ４抑制劑、其製備方法及其在醫藥上的應用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR920701162A (ko) * | 1990-03-28 | 1992-08-11 | 오츠카 아끼히코 | 퀴놀린 유도체, 당해 유도체를 함유하는 항궤양제 및 당해 유도체의 제조방법 |
| AU722662B2 (en) * | 1996-05-20 | 2000-08-10 | Darwin Discovery Limited | Quinoline sulfonamides as TNF inhibitors and as PDE-IV inhibitors |
| ATE303993T1 (de) * | 1997-12-22 | 2005-09-15 | Pharmacia & Upjohn Co Llc | 4-hydroxychinolin-3-carboxamide und hydrazide als antivirale wirkstoffe |
| US6576644B2 (en) * | 2000-09-06 | 2003-06-10 | Bristol-Myers Squibb Co. | Quinoline inhibitors of cGMP phosphodiesterase |
| SE0101675D0 (sv) * | 2001-05-11 | 2001-05-11 | Astrazeneca Ab | Novel composition |
| JO2311B1 (en) * | 2001-08-29 | 2005-09-12 | ميرك فروست كندا ليمتد | Alkyl inhibitors Ariel phosphodiesterase-4 |
-
2003
- 2003-09-27 GB GBGB0322722.0A patent/GB0322722D0/en not_active Ceased
-
2004
- 2004-09-23 ES ES04765656T patent/ES2298806T3/es not_active Expired - Lifetime
- 2004-09-23 DE DE602004011548T patent/DE602004011548T2/de not_active Expired - Fee Related
- 2004-09-23 WO PCT/EP2004/010844 patent/WO2005030212A1/en not_active Ceased
- 2004-09-23 US US10/572,914 patent/US20080096884A1/en not_active Abandoned
- 2004-09-23 JP JP2006527374A patent/JP2007506703A/ja active Pending
- 2004-09-23 EP EP04765656A patent/EP1673086B1/en not_active Expired - Lifetime
- 2004-09-23 AT AT04765656T patent/ATE384530T1/de not_active IP Right Cessation
- 2004-09-24 TW TW093129113A patent/TW200526584A/zh unknown
- 2004-09-24 AR ARP040103472A patent/AR045824A1/es not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| DE602004011548D1 (de) | 2008-03-13 |
| DE602004011548T2 (de) | 2009-01-29 |
| AR045824A1 (es) | 2005-11-16 |
| US20080096884A1 (en) | 2008-04-24 |
| ATE384530T1 (de) | 2008-02-15 |
| JP2007506703A (ja) | 2007-03-22 |
| WO2005030212A1 (en) | 2005-04-07 |
| GB0322722D0 (en) | 2003-10-29 |
| EP1673086B1 (en) | 2008-01-23 |
| EP1673086A1 (en) | 2006-06-28 |
| TW200526584A (en) | 2005-08-16 |
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