ZA200602415B - Pyridazin-3 (2H) -one derivatives and their use as PDE4 inhibitors - Google Patents
Pyridazin-3 (2H) -one derivatives and their use as PDE4 inhibitors Download PDFInfo
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- ZA200602415B ZA200602415B ZA200602415A ZA200602415A ZA200602415B ZA 200602415 B ZA200602415 B ZA 200602415B ZA 200602415 A ZA200602415 A ZA 200602415A ZA 200602415 A ZA200602415 A ZA 200602415A ZA 200602415 B ZA200602415 B ZA 200602415B
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- amino
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims description 16
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 title description 4
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title description 4
- -1 hydroxycarbonyi Chemical group 0.000 claims description 366
- 125000001424 substituent group Chemical group 0.000 claims description 201
- 125000005843 halogen group Chemical group 0.000 claims description 136
- 125000003545 alkoxy group Chemical group 0.000 claims description 126
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 117
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 113
- 125000000217 alkyl group Chemical group 0.000 claims description 102
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 85
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 81
- 125000004414 alkyl thio group Chemical group 0.000 claims description 65
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 60
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 60
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 55
- 125000002252 acyl group Chemical group 0.000 claims description 50
- 125000004442 acylamino group Chemical group 0.000 claims description 49
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 48
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000004104 aryloxy group Chemical group 0.000 claims description 43
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000005110 aryl thio group Chemical group 0.000 claims description 34
- 125000001072 heteroaryl group Chemical group 0.000 claims description 34
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 34
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 28
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims description 25
- 125000004043 oxo group Chemical group O=* 0.000 claims description 24
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 23
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000005842 heteroatom Chemical group 0.000 claims description 22
- 125000002950 monocyclic group Chemical group 0.000 claims description 20
- 125000004423 acyloxy group Chemical group 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 18
- 239000005864 Sulphur Chemical group 0.000 claims description 18
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 18
- 239000001301 oxygen Chemical group 0.000 claims description 18
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 13
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims description 11
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 11
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 11
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 9
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000000623 heterocyclic group Chemical group 0.000 claims description 6
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- 201000010099 disease Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
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- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims description 3
- 125000000676 alkoxyimino group Chemical group 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
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- 201000004681 Psoriasis Diseases 0.000 claims description 2
- 108091008874 T cell receptors Proteins 0.000 claims description 2
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- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzenecarbonitrile Natural products N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 11
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 4
- 125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 3
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
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- 235000010233 benzoic acid Nutrition 0.000 claims 2
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- CTBPVFDWXAPPTN-UHFFFAOYSA-N 2-ethyl-4-(4-fluoroanilino)-6-phenylpyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=CC=CC=2)C=C1NC1=CC=C(F)C=C1 CTBPVFDWXAPPTN-UHFFFAOYSA-N 0.000 claims 1
- SLRXCHGHRRRYFX-UHFFFAOYSA-N 2-ethyl-4-(isoquinolin-4-ylamino)-6-pyridin-4-ylpyridazin-3-one Chemical compound C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=NC=C1 SLRXCHGHRRRYFX-UHFFFAOYSA-N 0.000 claims 1
- ANAZDCIIOKPEKT-UHFFFAOYSA-N 2-ethyl-5-(5-methyl-1,3,4-oxadiazol-2-yl)-6-phenyl-4-(3,4,5-trifluoroanilino)pyridazin-3-one Chemical compound N=1N=C(C)OC=1C1=C(NC=2C=C(F)C(F)=C(F)C=2)C(=O)N(CC)N=C1C1=CC=CC=C1 ANAZDCIIOKPEKT-UHFFFAOYSA-N 0.000 claims 1
- WMDOWXJPNPGLSK-UHFFFAOYSA-N 2-ethyl-6-(4-methylphenyl)-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=CC(C)=CC=2)C=C1NC1=CC=CN=C1 WMDOWXJPNPGLSK-UHFFFAOYSA-N 0.000 claims 1
- SIBXTUPNVFJKLM-UHFFFAOYSA-N 2-ethyl-6-(5-methylpyridin-3-yl)-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=C(C)C=NC=2)C=C1NC1=CC=CN=C1 SIBXTUPNVFJKLM-UHFFFAOYSA-N 0.000 claims 1
- SGLNSMCZASHWKJ-UHFFFAOYSA-N 2-ethyl-6-pyridin-3-yl-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=NC=CC=2)C=C1NC1=CC=CN=C1 SGLNSMCZASHWKJ-UHFFFAOYSA-N 0.000 claims 1
- XWJAMKHTEXUFMJ-UHFFFAOYSA-N 2-ethyl-6-pyridin-4-yl-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=CN=CC=2)C=C1NC1=CC=CN=C1 XWJAMKHTEXUFMJ-UHFFFAOYSA-N 0.000 claims 1
- RNYAIIMWJZIICO-UHFFFAOYSA-N 4-(3-chloroanilino)-2-ethyl-5-(1-hydroxyethyl)-6-phenylpyridazin-3-one Chemical compound CC(O)C1=C(NC=2C=C(Cl)C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 RNYAIIMWJZIICO-UHFFFAOYSA-N 0.000 claims 1
- RGZBSRQKDFBGBH-UHFFFAOYSA-N 4-(3-chloroanilino)-2-ethyl-5-(1-methoxyethyl)-6-phenylpyridazin-3-one Chemical compound COC(C)C1=C(NC=2C=C(Cl)C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 RGZBSRQKDFBGBH-UHFFFAOYSA-N 0.000 claims 1
- XBEGKIQVXKMHHC-UHFFFAOYSA-N 4-(3-chloroanilino)-2-ethyl-6-phenylpyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=CC=CC=2)C=C1NC1=CC=CC(Cl)=C1 XBEGKIQVXKMHHC-UHFFFAOYSA-N 0.000 claims 1
- FHSGEHGAXJISFE-UHFFFAOYSA-N 4-anilino-2,5-diethyl-6-phenylpyridazin-3-one Chemical compound CCC=1C(C=2C=CC=CC=2)=NN(CC)C(=O)C=1NC1=CC=CC=C1 FHSGEHGAXJISFE-UHFFFAOYSA-N 0.000 claims 1
- DLMKKFLPEQIYOR-UHFFFAOYSA-N 5-(4-cyanoanilino)-1-ethyl-3-(4-fluorophenyl)-6-oxopyridazine-4-carbonitrile Chemical compound N#CC1=C(NC=2C=CC(=CC=2)C#N)C(=O)N(CC)N=C1C1=CC=C(F)C=C1 DLMKKFLPEQIYOR-UHFFFAOYSA-N 0.000 claims 1
- XLLOUMUSMQWNFL-UHFFFAOYSA-N 6-(3-chlorophenyl)-2-ethyl-4-(isoquinolin-4-ylamino)pyridazin-3-one Chemical compound C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC(Cl)=C1 XLLOUMUSMQWNFL-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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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
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- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/50—Pyridazines; Hydrogenated pyridazines
- A61K31/501—Pyridazines; Hydrogenated pyridazines not condensed and containing further heterocyclic rings
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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Families Citing this family (65)
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| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| EP1604988A1 (en) * | 2004-05-18 | 2005-12-14 | Sanofi-Aventis Deutschland GmbH | Pyridazinone derivatives, methods for producing them and their use as pharmaceuticals |
| ES2257152B1 (es) | 2004-05-31 | 2007-07-01 | Laboratorios Almirall S.A. | Combinaciones que comprenden agentes antimuscarinicos y agonistas beta-adrenergicos. |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251867B1 (es) * | 2004-06-21 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| JPWO2006041121A1 (ja) * | 2004-10-13 | 2008-05-15 | 協和醗酵工業株式会社 | 慢性皮膚疾患の治療および/または予防剤 |
| US20080085858A1 (en) * | 2004-10-13 | 2008-04-10 | Kyowa Hakko Kogyo Co., Ltd. | Pharmaceutical Composition |
| ES2265276B1 (es) | 2005-05-20 | 2008-02-01 | Laboratorios Almirall S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor beta2 adrenergico. |
| ES2298049B1 (es) | 2006-07-21 | 2009-10-20 | Laboratorios Almirall S.A. | Procedimiento para fabricar bromuro de 3(r)-(2-hidroxi-2,2-ditien-2-ilacetoxi)-1-(3-fenoxipropil)-1-azoniabiciclo (2.2.2) octano. |
| ES2306595B1 (es) | 2007-02-09 | 2009-09-11 | Laboratorios Almirall S.A. | Sal de napadisilato de 5-(2-((6-(2,2-difluoro-2-feniletoxi)hexil)amino)-1-hidroxietil)-8-hidroxiquinolin-2(1h)-ona como agonista del receptor adrenergico beta2. |
| ES2320954B1 (es) * | 2007-03-02 | 2010-03-16 | Laboratorio Almirall S.A. | Nuevo procedimiento de preparacion de 3-metil-4-fenilisoxazolo (3,4-d)iridazin-7(6h)-ona. |
| ES2320955B1 (es) | 2007-03-02 | 2010-03-16 | Laboratorios Almirall S.A. | Nuevos derivados de 3-((1,2,4)triazolo(4,3-a)piridin-7-il)benzamida. |
| ES2320961B1 (es) | 2007-11-28 | 2010-03-17 | Laboratorios Almirall, S.A. | Derivados de 4-(2-amino-1-hidroxietil)fenol como agonistas del receptor adrenergico beta2. |
| WO2009098144A1 (en) * | 2008-02-05 | 2009-08-13 | F. Hoffmann-La Roche Ag | Novel pyridinones and pyridazinones |
| EP2096105A1 (en) * | 2008-02-28 | 2009-09-02 | Laboratorios Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the b2 adrenergic receptor |
| EP2100599A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2100598A1 (en) | 2008-03-13 | 2009-09-16 | Laboratorios Almirall, S.A. | Inhalation composition containing aclidinium for treatment of asthma and chronic obstructive pulmonary disease |
| EP2108641A1 (en) | 2008-04-11 | 2009-10-14 | Laboratorios Almirall, S.A. | New substituted spiro[cycloalkyl-1,3'-indo]-2'(1'H)-one derivatives and their use as p38 mitogen-activated kinase inhibitors |
| EP2113503A1 (en) | 2008-04-28 | 2009-11-04 | Laboratorios Almirall, S.A. | New substituted indolin-2-one derivatives and their use as p39 mitogen-activated kinase inhibitors |
| EP2196465A1 (en) * | 2008-12-15 | 2010-06-16 | Almirall, S.A. | (3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors |
| UY32297A (es) | 2008-12-22 | 2010-05-31 | Almirall Sa | Sal mesilato de 5-(2-{[6-(2,2-difluoro-2-fenilitoxi) hexil]amino}-1-hidroxietil)-8-hidroxiquinolin-2( 1h)-ona como agonista del receptor b(beta)2 acrenérgico |
| EP2221055A1 (en) | 2009-02-18 | 2010-08-25 | Almirall, S.A. | 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one for the treatment of lung function |
| EP2221297A1 (en) | 2009-02-18 | 2010-08-25 | Almirall, S.A. | 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one and its use in the treatment of pulmonary diseases |
| EP2228368A1 (en) | 2009-03-12 | 2010-09-15 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| EP2322176A1 (en) | 2009-11-11 | 2011-05-18 | Almirall, S.A. | New 7-phenyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one derivatives |
| EP2338888A1 (en) | 2009-12-24 | 2011-06-29 | Almirall, S.A. | Imidazopyridine derivatives as JAK inhibitors |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
| EP2360158A1 (en) | 2010-02-18 | 2011-08-24 | Almirall, S.A. | Pyrazole derivatives as jak inhibitors |
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| EP2394998A1 (en) * | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
| EP2397482A1 (en) | 2010-06-15 | 2011-12-21 | Almirall, S.A. | Heteroaryl imidazolone derivatives as jak inhibitors |
| EP2441755A1 (en) | 2010-09-30 | 2012-04-18 | Almirall, S.A. | Pyridine- and isoquinoline-derivatives as Syk and JAK kinase inhibitors |
| EP2457900A1 (en) | 2010-11-25 | 2012-05-30 | Almirall, S.A. | New pyrazole derivatives having CRTh2 antagonistic behaviour |
| EP2463289A1 (en) | 2010-11-26 | 2012-06-13 | Almirall, S.A. | Imidazo[1,2-b]pyridazine derivatives as JAK inhibitors |
| EP2489663A1 (en) | 2011-02-16 | 2012-08-22 | Almirall, S.A. | Compounds as syk kinase inhibitors |
| EP2510928A1 (en) | 2011-04-15 | 2012-10-17 | Almirall, S.A. | Aclidinium for use in improving the quality of sleep in respiratory patients |
| EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine derivatives as PI3K inhibitors |
| EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
| EP2527344A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | Pyridin-2(1H)-one derivatives useful as medicaments for the treatment of myeloproliferative disorders, transplant rejection, immune-mediated and inflammatory diseases |
| EP2526945A1 (en) | 2011-05-25 | 2012-11-28 | Almirall, S.A. | New CRTH2 Antagonists |
| EP2548863A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists. |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| EP2554544A1 (en) | 2011-08-01 | 2013-02-06 | Almirall, S.A. | Pyridin-2(1h)-one derivatives as jak inhibitors |
| EP2578570A1 (en) | 2011-10-07 | 2013-04-10 | Almirall, S.A. | Novel process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(r)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one via novel intermediates of synthesis. |
| EP2592078A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2592077A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2641900A1 (en) | 2012-03-20 | 2013-09-25 | Almirall, S.A. | Novel polymorphic Crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1h)-one, heminapadisylate as agonist of the ß2 adrenergic receptor. |
| EP2647627A1 (en) | 2012-04-02 | 2013-10-09 | Almirall, S.A. | Salts of 5-[(1r)-2-({2-[4-(2,2-difluoro-2-phenylethoxy)phenyl] ethyl}amino)-1-hydroxyethyl]-8-hydroxyquinolin-2(1h)-one. |
| EP2666465A1 (en) | 2012-05-25 | 2013-11-27 | Almirall, S.A. | Novel dosage and formulation |
| EP2668941A1 (en) | 2012-05-31 | 2013-12-04 | Almirall, S.A. | Novel dosage form and formulation of abediterol |
| EP2858982A4 (en) | 2012-06-12 | 2015-11-11 | Abbvie Inc | PYRIDINONE AND PYRIDAZINONE DERIVATIVES |
| WO2014060431A1 (en) | 2012-10-16 | 2014-04-24 | Almirall, S.A. | Pyrrolotriazinone derivatives as pi3k inhibitors |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| PT2931275T (pt) | 2012-12-17 | 2022-06-30 | Almirall Sa | Aclidínio para usar no aumento da atividade física na vida diária de um doente que sofre de doença pulmonar obstrutiva crónica |
| BR112015013628A2 (pt) | 2012-12-18 | 2017-07-11 | Almirall Sa | derivados de carbamato de ciclo-hexila e quinuclidinila tendo atividades agonista adrenérgica de beta2 e antagonista muscarínica de m3 |
| AR094797A1 (es) | 2013-02-15 | 2015-08-26 | Almirall Sa | Derivados de pirrolotriazina como inhibidores de pi3k |
| EP2848615A1 (en) | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
| FR3027901B1 (fr) * | 2014-10-31 | 2018-03-16 | Universite De Reims Champagne Ardenne | Nouveaux procedes appartenant a la famille des pyridazinones. |
| EP3265453B1 (en) * | 2015-03-05 | 2022-06-29 | Boehringer Ingelheim International GmbH | New pyridinones and isoquinolinones as inhibitors of the bromodomain brd9 |
| CA3102762A1 (en) | 2018-06-04 | 2019-12-12 | Ohio State Innovation Foundation | Eaat2 activators and methods of using thereof |
| CN109620829B (zh) * | 2018-12-29 | 2021-04-06 | 温州医科大学附属第一医院 | 一种治疗急性呼吸窘迫综合征的药物组合物及其制备方法 |
| TW202321229A (zh) * | 2021-08-18 | 2023-06-01 | 美商富曼西公司 | 殺真菌的取代的雜環化合物 |
| WO2023204124A1 (ja) * | 2022-04-20 | 2023-10-26 | 日本曹達株式会社 | ピリダジノン化合物並びに農園芸用殺菌剤、殺線虫剤、および医療用・動物用抗真菌剤 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US2786840A (en) * | 1957-03-26 | Aminopyridazone compounds and their | ||
| US2824873A (en) * | 1958-02-25 | Production of pyridazone derivatives | ||
| DE579391C (de) * | 1932-02-07 | 1933-06-24 | Schering Kahlbaum Ag | Verfahren zur Darstellung von in 5-Stellung substituierten 1, 3-Dialkylpyridazonen |
| GB656228A (en) * | 1948-12-30 | 1951-08-15 | Walter Norman Haworth | The manufacture of analgesics from pyridazone and pyridazine derivatives |
| GB788393A (en) * | 1953-04-30 | 1958-01-02 | Ciba Ltd | Process for the manufacture of pyridazone compounds |
| DE932489C (de) * | 1953-09-11 | 1955-09-01 | Hoffmann La Roche | Verfahren zur Herstellung von neuen Xanthinbasen und deren Salzen |
| GB794870A (en) * | 1955-05-07 | 1958-05-14 | Basf Ag | A process for the production of 3-oxo-2,3-dihydropyridazine derivatives |
| GB788502A (en) * | 1956-05-30 | 1958-01-02 | Chimie Atomistique | Pyridazine compounds and process of preparing the latter |
| US2834780A (en) * | 1956-07-05 | 1958-05-13 | Dow Chemical Co | Phthalidyl piperazines |
| US3014034A (en) * | 1959-01-22 | 1961-12-19 | Ciba Pharm Prod Inc | 1, 3-diaryl, 5-amino-pyridazinones |
| GB889317A (en) * | 1959-01-22 | 1962-02-14 | Ciba Ltd | New phenyl-diazines and a process for their manufacture |
| SU405344A1 (ru) | 1970-06-01 | 1975-08-25 | Всесоюзный научно-исследовательский химико-фармацевтический институт им. С.Орджоникидзе | Способ получени производных 3-замещенных 5-(2-оксифениламино)-пиридазона-6 |
| JPS5312880A (en) * | 1976-07-21 | 1978-02-04 | Morishita Pharma | Pyridazinone derivatives |
| TWI241295B (en) * | 1998-03-02 | 2005-10-11 | Kowa Co | Pyridazine derivative and medicine containing the same as effect component |
| KR20030031907A (ko) * | 2000-06-05 | 2003-04-23 | 알타나 파마 아게 | β-2-아드레날린 수용체 작동물질로서 뿐만 아니라PDE4-억제제로서 효과적인 화합물 |
| CA2473461C (en) * | 2002-01-11 | 2011-11-01 | Sankyo Company, Limited | Amino alcohol derivative or phosphonic acid derivative and medicinal composition containing these |
| ES2211344B1 (es) | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| MXPA05010081A (es) * | 2003-03-24 | 2005-11-23 | Hoffmann La Roche | Bencil-piridazinonas como inhibidores de transcriptasa inversa. |
-
2003
- 2003-11-10 ES ES200302613A patent/ES2232306B1/es not_active Expired - Fee Related
-
2004
- 2004-08-11 UA UAA200606338A patent/UA82420C2/uk unknown
- 2004-11-08 PE PE2004001087A patent/PE20050490A1/es not_active Application Discontinuation
- 2004-11-08 EP EP04797700A patent/EP1682519A1/en not_active Withdrawn
- 2004-11-08 KR KR1020067011454A patent/KR20070001907A/ko not_active Withdrawn
- 2004-11-08 WO PCT/EP2004/012604 patent/WO2005049581A1/en not_active Ceased
- 2004-11-08 US US10/578,594 patent/US7511038B2/en not_active Expired - Fee Related
- 2004-11-08 CN CNA2004800331136A patent/CN1878759A/zh active Pending
- 2004-11-08 RU RU2006120082/04A patent/RU2006120082A/ru not_active Application Discontinuation
- 2004-11-08 BR BRPI0416212-9A patent/BRPI0416212A/pt not_active IP Right Cessation
- 2004-11-08 AU AU2004291282A patent/AU2004291282A1/en not_active Abandoned
- 2004-11-08 CA CA002545193A patent/CA2545193A1/en not_active Abandoned
- 2004-11-08 JP JP2006538762A patent/JP2007510689A/ja active Pending
- 2004-11-09 AR ARP040104120A patent/AR046445A1/es unknown
- 2004-11-10 TW TW093134355A patent/TW200526593A/zh unknown
-
2006
- 2006-03-24 ZA ZA200602415A patent/ZA200602415B/en unknown
- 2006-04-27 IL IL175278A patent/IL175278A0/en unknown
- 2006-05-03 EC EC2006006541A patent/ECSP066541A/es unknown
- 2006-05-10 CO CO06044361A patent/CO5690558A2/es not_active Application Discontinuation
- 2006-06-12 NO NO20062726A patent/NO20062726L/no not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| UA82420C2 (en) | 2008-04-10 |
| RU2006120082A (ru) | 2008-01-10 |
| TW200526593A (en) | 2005-08-16 |
| CO5690558A2 (es) | 2006-10-31 |
| JP2007510689A (ja) | 2007-04-26 |
| CN1878759A (zh) | 2006-12-13 |
| US20070197536A1 (en) | 2007-08-23 |
| IL175278A0 (en) | 2006-09-05 |
| WO2005049581A8 (en) | 2006-05-04 |
| AU2004291282A1 (en) | 2005-06-02 |
| AR046445A1 (es) | 2005-12-07 |
| ES2232306A1 (es) | 2005-05-16 |
| WO2005049581A1 (en) | 2005-06-02 |
| ECSP066541A (es) | 2006-12-20 |
| KR20070001907A (ko) | 2007-01-04 |
| US7511038B2 (en) | 2009-03-31 |
| NO20062726L (no) | 2006-06-12 |
| CA2545193A1 (en) | 2005-06-02 |
| BRPI0416212A (pt) | 2007-01-02 |
| PE20050490A1 (es) | 2005-08-24 |
| EP1682519A1 (en) | 2006-07-26 |
| ES2232306B1 (es) | 2006-08-01 |
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