JP2008503531A5 - - Google Patents
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- Publication number
- JP2008503531A5 JP2008503531A5 JP2007517186A JP2007517186A JP2008503531A5 JP 2008503531 A5 JP2008503531 A5 JP 2008503531A5 JP 2007517186 A JP2007517186 A JP 2007517186A JP 2007517186 A JP2007517186 A JP 2007517186A JP 2008503531 A5 JP2008503531 A5 JP 2008503531A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- oxo
- dihydropyridazine
- ylamino
- carboxylic acid
- 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.)
- Pending
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- -1 hydroxy, hydroxycarbonyl Chemical group 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000005843 halogen group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004414 alkyl thio group Chemical group 0.000 claims description 13
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
- 125000004442 acylamino group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 7
- 125000003342 alkenyl group Chemical group 0.000 claims description 6
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 6
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 6
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000005110 aryl thio group Chemical group 0.000 claims description 5
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 claims description 5
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- AYQAYXANVWKXST-UHFFFAOYSA-N (3-oxo-1h-2-benzofuran-1-yl) 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound O1C(=O)C2=CC=CC=C2C1OC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 AYQAYXANVWKXST-UHFFFAOYSA-N 0.000 claims description 3
- JIPDQAIEXJPADH-UHFFFAOYSA-N 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 JIPDQAIEXJPADH-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- YRTLKHAPXWLXBG-UHFFFAOYSA-N butanoyloxymethyl 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound O=C1N(CC)N=C(C=2C=CC=CC=2)C(C(=O)OCOC(=O)CCC)=C1NC1=CC=CN=C1 YRTLKHAPXWLXBG-UHFFFAOYSA-N 0.000 claims description 3
- SVINEOXRWZEKBM-UHFFFAOYSA-N cyclohexyloxycarbonyloxymethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound C1CCCCC1OC(=O)OCOC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CC=C1 SVINEOXRWZEKBM-UHFFFAOYSA-N 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- OEPNIULYTJOPOW-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound CCOC(=O)COC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 OEPNIULYTJOPOW-UHFFFAOYSA-N 0.000 claims description 2
- KVXKNJUOGZSBHV-UHFFFAOYSA-N (2-oxo-2-phenylmethoxyethyl) 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)COC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 KVXKNJUOGZSBHV-UHFFFAOYSA-N 0.000 claims description 2
- RRVRXMWPEHHLJX-UHFFFAOYSA-N (2-oxo-2-phenylmethoxyethyl) 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)COC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 RRVRXMWPEHHLJX-UHFFFAOYSA-N 0.000 claims description 2
- RFSRFPWPEPMVPE-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 1-ethyl-3-(4-methylphenyl)-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-4-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=C(C)C=C1 RFSRFPWPEPMVPE-UHFFFAOYSA-N 0.000 claims description 2
- 241001024304 Mino Species 0.000 claims description 2
- SUJKVNMXHCHELC-UHFFFAOYSA-N methyl 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound COC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 SUJKVNMXHCHELC-UHFFFAOYSA-N 0.000 claims description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 6
- 125000005647 linker group Chemical group 0.000 claims 4
- UTFVFEWESJDJPX-UHFFFAOYSA-N 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-phenylpyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CC=C1 UTFVFEWESJDJPX-UHFFFAOYSA-N 0.000 claims 3
- 125000003118 aryl group Chemical group 0.000 claims 3
- 201000010099 disease Diseases 0.000 claims 3
- 125000000623 heterocyclic group Chemical group 0.000 claims 3
- 230000001575 pathological effect Effects 0.000 claims 3
- 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 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims 2
- 206010012438 Dermatitis atopic Diseases 0.000 claims 2
- 201000004681 Psoriasis Diseases 0.000 claims 2
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 2
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
- KWZNFMMDBXUYEK-UHFFFAOYSA-N benzyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CS1 KWZNFMMDBXUYEK-UHFFFAOYSA-N 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 2
- ZQOVMCITMFRZGF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound CCOC(=O)COC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CS1 ZQOVMCITMFRZGF-UHFFFAOYSA-N 0.000 claims 1
- WBNSRYIMLAZTFJ-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound O=C1N(CC)N=C(C=2SC=CC=2)C(C(=O)OCC(=O)OCC)=C1NC1=CC=CN=C1 WBNSRYIMLAZTFJ-UHFFFAOYSA-N 0.000 claims 1
- UXMXAWPLMKACIA-UHFFFAOYSA-N (2-oxo-1,3-dioxolan-4-yl) 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound C1OC(=O)OC1OC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 UXMXAWPLMKACIA-UHFFFAOYSA-N 0.000 claims 1
- ZFGXZAPWVWUKAF-UHFFFAOYSA-N (2-oxo-2-phenylmethoxyethyl) 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)COC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CS1 ZFGXZAPWVWUKAF-UHFFFAOYSA-N 0.000 claims 1
- TYMDATUIPDWLGT-UHFFFAOYSA-N (2-oxo-2-phenylmethoxyethyl) 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound C=1C=CC=CC=1COC(=O)COC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CS1 TYMDATUIPDWLGT-UHFFFAOYSA-N 0.000 claims 1
- REUFIMAVCLSMMJ-UHFFFAOYSA-N (2-oxo-2-pyridin-4-ylethyl) 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound C=1C=NC=CC=1C(=O)COC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 REUFIMAVCLSMMJ-UHFFFAOYSA-N 0.000 claims 1
- MINSMCISGFLMIQ-UHFFFAOYSA-N (2-oxo-2-pyrrolidin-1-ylethyl) 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound C1CCCN1C(=O)COC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 MINSMCISGFLMIQ-UHFFFAOYSA-N 0.000 claims 1
- OQPZLRXILZSINC-UHFFFAOYSA-N (3-amino-3-oxopropyl) 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound NC(=O)CCOC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 OQPZLRXILZSINC-UHFFFAOYSA-N 0.000 claims 1
- DMJCJQSMRTUWOS-UHFFFAOYSA-N (3-fluorophenyl)methyl 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound C=1C=CC(F)=CC=1COC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 DMJCJQSMRTUWOS-UHFFFAOYSA-N 0.000 claims 1
- RHKDFZKGDRQCPC-UHFFFAOYSA-N (4-fluorophenyl)methyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-thiophen-3-ylpyridazine-4-carboxylate Chemical compound C=1C=C(F)C=CC=1COC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C=1C=CSC=1 RHKDFZKGDRQCPC-UHFFFAOYSA-N 0.000 claims 1
- SUILFGYRLGYPIC-UHFFFAOYSA-N (4-fluorophenyl)methyl 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-3-ylpyridazine-4-carboxylate Chemical compound C=1C=C(F)C=CC=1COC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C=1C=CSC=1 SUILFGYRLGYPIC-UHFFFAOYSA-N 0.000 claims 1
- IGXQOAOVRWRXTR-UHFFFAOYSA-N (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound O1C(=O)OC(C)=C1COC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 IGXQOAOVRWRXTR-UHFFFAOYSA-N 0.000 claims 1
- QCLGYOHTBTZSDN-UHFFFAOYSA-N (6-ethoxy-6-oxohexyl) 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-3-ylpyridazine-4-carboxylate Chemical compound O=C1N(CC)N=C(C2=CSC=C2)C(C(=O)OCCCCCC(=O)OCC)=C1NC1=CC=CN=C1 QCLGYOHTBTZSDN-UHFFFAOYSA-N 0.000 claims 1
- PJDZQOIYQQRWJD-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound C1CCCCC1OC(=O)OC(C)OC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 PJDZQOIYQQRWJD-UHFFFAOYSA-N 0.000 claims 1
- YYRKGSDUHBQLOB-UHFFFAOYSA-N 1-cyclohexyloxycarbonyloxyethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound C1CCCCC1OC(=O)OC(C)OC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CC=C1 YYRKGSDUHBQLOB-UHFFFAOYSA-N 0.000 claims 1
- PYPSOMQKFXTIJF-UHFFFAOYSA-N 1-ethoxycarbonyloxyethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound O=C1N(CC)N=C(C=2C=CC=CC=2)C(C(=O)OC(C)OC(=O)OCC)=C1NC1=CN=CC=C1C PYPSOMQKFXTIJF-UHFFFAOYSA-N 0.000 claims 1
- ROFGSTUXSJJPOV-UHFFFAOYSA-N 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-phenylpyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 ROFGSTUXSJJPOV-UHFFFAOYSA-N 0.000 claims 1
- ZXOWDVZMXXEVLN-UHFFFAOYSA-N 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-thiophen-2-ylpyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CS1 ZXOWDVZMXXEVLN-UHFFFAOYSA-N 0.000 claims 1
- SVKAVXBNAOBVJC-UHFFFAOYSA-N 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-thiophen-2-ylpyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CS1 SVKAVXBNAOBVJC-UHFFFAOYSA-N 0.000 claims 1
- JCCXNKIMXIQXQL-UHFFFAOYSA-N 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 JCCXNKIMXIQXQL-UHFFFAOYSA-N 0.000 claims 1
- KWKJBUWSUGOXAM-UHFFFAOYSA-N 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-2-ylpyridazine-4-carboxylic acid Chemical compound OC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CS1 KWKJBUWSUGOXAM-UHFFFAOYSA-N 0.000 claims 1
- GAFOQWRUIGNQDB-UHFFFAOYSA-N 1-propan-2-yloxycarbonyloxyethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound CC(C)OC(=O)OC(C)OC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CC=C1 GAFOQWRUIGNQDB-UHFFFAOYSA-N 0.000 claims 1
- YYYKMPCEPVSSSB-UHFFFAOYSA-N 1-propan-2-yloxycarbonyloxyethyl 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound CC(C)OC(=O)OC(C)OC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 YYYKMPCEPVSSSB-UHFFFAOYSA-N 0.000 claims 1
- IUEMBCDGEXTGIJ-UHFFFAOYSA-N 2,2-dimethylbutanoyloxymethyl 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound CCC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 IUEMBCDGEXTGIJ-UHFFFAOYSA-N 0.000 claims 1
- CYPGRSZMLAOGFL-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 1-ethyl-5-(isoquinolin-4-ylamino)-3-(4-methylphenyl)-6-oxopyridazine-4-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=C(C)C=C1 CYPGRSZMLAOGFL-UHFFFAOYSA-N 0.000 claims 1
- LJGLLNSENMUOQF-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 LJGLLNSENMUOQF-UHFFFAOYSA-N 0.000 claims 1
- GMJJBMAYDTZOMV-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-3-phenylpyridazine-4-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C1=CC=CC=C1 GMJJBMAYDTZOMV-UHFFFAOYSA-N 0.000 claims 1
- SBDIUDUAUBGHNR-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 1-ethyl-6-oxo-3-phenyl-5-(pyridin-3-ylamino)pyridazine-4-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 SBDIUDUAUBGHNR-UHFFFAOYSA-N 0.000 claims 1
- ZPFDNXFWHRBUIQ-UHFFFAOYSA-N 2,2-dimethylpropanoyloxymethyl 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 ZPFDNXFWHRBUIQ-UHFFFAOYSA-N 0.000 claims 1
- DXMXLLYJNAFHGX-UHFFFAOYSA-N 2-(dimethylamino)ethyl 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound CN(C)CCOC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 DXMXLLYJNAFHGX-UHFFFAOYSA-N 0.000 claims 1
- UTNBEFDPUZDWLI-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound CC(C)(C)OC(=O)NCCOC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CS1 UTNBEFDPUZDWLI-UHFFFAOYSA-N 0.000 claims 1
- NFXMSFXHAXKYNP-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound CC(C)(C)OC(=O)NCCOC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 NFXMSFXHAXKYNP-UHFFFAOYSA-N 0.000 claims 1
- SPWNPRPDIBHYGB-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound CC(C)(C)OC(=O)NCCOC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CS1 SPWNPRPDIBHYGB-UHFFFAOYSA-N 0.000 claims 1
- VPVMFVPGIBKFFG-UHFFFAOYSA-N 2-acetyloxyethyl 1-ethyl-6-oxo-3-phenyl-5-(quinolin-5-ylamino)pyridazine-4-carboxylate Chemical compound CC(=O)OCCOC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 VPVMFVPGIBKFFG-UHFFFAOYSA-N 0.000 claims 1
- QYNIQKVOSKJEDI-UHFFFAOYSA-N 2-acetyloxyethyl 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-3-thiophen-2-ylpyridazine-4-carboxylate Chemical compound CC(=O)OCCOC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CS1 QYNIQKVOSKJEDI-UHFFFAOYSA-N 0.000 claims 1
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| ES200401512A ES2251867B1 (es) | 2004-06-21 | 2004-06-21 | Nuevos derivados de piridazin-3(2h)-ona. |
| PCT/EP2005/006712 WO2005123693A1 (en) | 2004-06-21 | 2005-06-21 | Pyridazin-3(2h)-one derivatives and their use as pde4 inhibitors |
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| EP (1) | EP1781621A1 (https=) |
| JP (1) | JP2008503531A (https=) |
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Families Citing this family (56)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2211344B1 (es) | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251866B1 (es) | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
| JO2849B1 (en) | 2007-02-13 | 2015-03-15 | جانسين فارماسوتيكا ان. في | Dopamine 2 receptor antagonists are rapidly hydrolyzed |
| 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. |
| US9086277B2 (en) * | 2007-03-13 | 2015-07-21 | Certusview Technologies, Llc | Electronically controlled marking apparatus and methods |
| KR20100016620A (ko) | 2007-04-23 | 2010-02-12 | 얀센 파마슈티카 엔.브이. | 속해리성 도파민 2 수용체 길항제로서의 4-알콕시피리다진 유도체 |
| AU2008240729B2 (en) | 2007-04-23 | 2012-08-23 | Janssen Pharmaceutica N.V. | Thia(dia)zoles as fast dissociating dopamine 2 receptor antagonists |
| 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 |
| 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 |
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| 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 |
| CA2730774C (en) | 2008-07-31 | 2016-09-13 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
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| EP2360158A1 (en) | 2010-02-18 | 2011-08-24 | Almirall, S.A. | Pyrazole derivatives as jak inhibitors |
| UY33213A (es) | 2010-02-18 | 2011-09-30 | Almirall Sa | Derivados de pirazol como inhibidores de jak |
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| 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 |
| 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 |
| EP2548876A1 (en) | 2011-07-18 | 2013-01-23 | Almirall, S.A. | New CRTh2 antagonists |
| EP2548863A1 (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 |
| US20140278981A1 (en) * | 2011-10-06 | 2014-09-18 | Gueorgui Mersov | Automated allocation of media via network |
| 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. |
| EP2592077A1 (en) | 2011-11-11 | 2013-05-15 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and M3 muscarinic antagonist activities |
| EP2592078A1 (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 |
| JP6215315B2 (ja) | 2012-06-12 | 2017-10-18 | アッヴィ・インコーポレイテッド | ピリジノンおよびピリダジノン誘導体 |
| 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 |
| LT2931275T (lt) | 2012-12-17 | 2022-06-27 | Almirall S.A. | Aklidiniumas, skirtas naudoti fizinio aktyvumo kasdieniniame gyvenime padidinimui pacientui, sergančiam lėtine obstrukcine plaučių liga |
| ES2750523T3 (es) | 2012-12-18 | 2020-03-26 | Almirall Sa | Derivados de ciclohexil y quinuclidinil carbamato que tienen actividades de agonista beta2 adrenérgicos y antagonistas muscarínicos M3 |
| TW201446767A (zh) | 2013-02-15 | 2014-12-16 | Almirall Sa | 作為磷脂肌醇3-激酶抑製劑之吡咯並三嗪衍生物 |
| TWI643853B (zh) | 2013-02-27 | 2018-12-11 | 阿爾米雷爾有限公司 | 同時具有β2腎上腺素受體促效劑和M3毒蕈鹼受體拮抗劑活性之2-氨基-1-羥乙基-8-羥基喹啉-2(1H)-酮衍生物之鹽類 |
| EP2848615A1 (en) | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
| TWI641373B (zh) | 2013-07-25 | 2018-11-21 | 阿爾米雷爾有限公司 | 具有蕈毒鹼受體拮抗劑和β２腎上腺素受體促效劑二者之活性的２－胺基－１－羥乙基－８－羥基喹啉－２（１Ｈ）－酮衍生物之鹽 |
| TW201517906A (zh) | 2013-07-25 | 2015-05-16 | Almirall Sa | 含有ｍａｂａ化合物和皮質類固醇之組合 |
| TW201617343A (zh) | 2014-09-26 | 2016-05-16 | 阿爾米雷爾有限公司 | 具有β２腎上腺素促效劑及Ｍ３蕈毒拮抗劑活性之新穎雙環衍生物 |
| WO2023008885A1 (ko) * | 2021-07-27 | 2023-02-02 | 보로노이바이오 주식회사 | 피롤로피리미딘 유도체 화합물 및 이의 용도 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5679696A (en) * | 1992-07-28 | 1997-10-21 | Rhone-Poulenc Rorer Limited | Compounds containing phenyl linked to aryl or heteroaryl by an aliphatic-or heteroatom-containing linking group |
| DE19514568A1 (de) * | 1995-04-20 | 1996-10-24 | Merck Patent Gmbh | Arylalkyl-pyridazinone |
| DE19533975A1 (de) * | 1995-09-14 | 1997-03-20 | Merck Patent Gmbh | Arylalkyl-diazinone |
| DE19540475A1 (de) * | 1995-10-20 | 1997-04-24 | Schering Ag | Chirale Methylphenyloxazolidinone |
| CN1219171A (zh) * | 1996-05-20 | 1999-06-09 | 达尔文发现有限公司 | 苯并呋喃甲酰胺及其治疗用途 |
| EP0952832B1 (en) * | 1996-05-20 | 2008-08-27 | Darwin Discovery Limited | Quinoline carboxamides as tnf inhibitors and as pde-iv inhibitors |
| WO1999026616A1 (en) * | 1997-11-25 | 1999-06-03 | Warner-Lambert Company | Benzenesulfonamide inhibitors of pde-iv and their therapeutic use |
| AU764005B2 (en) * | 1999-02-25 | 2003-08-07 | Merck Frosst Canada & Co. | PDE IV inhibiting compounds, compositions and methods of treatment |
| CA2742411A1 (en) * | 2000-09-18 | 2002-03-21 | Eisai R&D Management Co., Ltd. | Pyridazinone and triazinone compounds and use thereof as pharmaceutical preparations |
| US6699890B2 (en) * | 2000-12-22 | 2004-03-02 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
| CN1604776A (zh) * | 2001-10-16 | 2005-04-06 | 记忆药物公司 | 作为用于治疗神经病综合症的pde－4抑制剂的4－(4－烷氧基－3－羟基苯基)－2－吡咯烷酮衍生物 |
| AR037517A1 (es) * | 2001-11-05 | 2004-11-17 | Novartis Ag | Derivados de naftiridinas, un proceso para su preparacion, composicion farmaceutica y el uso de los mismos para la preparacion de un medicamento para el tratamiento de una enfermedad inflamatoria |
| ES2195785B1 (es) * | 2002-05-16 | 2005-03-16 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| AU2003295656B2 (en) * | 2002-11-19 | 2010-11-11 | Memory Pharmaceuticals Corporation | Pyridine N-oxide compounds as phosphodiesterase 4 inhibitors |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| AU2004232973A1 (en) * | 2003-04-18 | 2004-11-04 | Memory Pharmaceuticals Corporation | Pyrazole derivatives as phosphodiesterase 4 inhibitors |
| ES2232306B1 (es) * | 2003-11-10 | 2006-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| ES2251866B1 (es) * | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| 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. |
| KR20100098653A (ko) * | 2007-11-21 | 2010-09-08 | 디코드 제네틱스 이에이치에프 | 염증의 치료를 위한 바이아릴 ｐｄｅ４ 억제제 |
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2004
- 2004-06-21 ES ES200401512A patent/ES2251867B1/es not_active Expired - Fee Related
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2005
- 2005-06-20 PE PE2005000702A patent/PE20060531A1/es not_active Application Discontinuation
- 2005-06-21 AU AU2005254704A patent/AU2005254704A1/en not_active Abandoned
- 2005-06-21 BR BRPI0511344-0A patent/BRPI0511344A/pt not_active IP Right Cessation
- 2005-06-21 KR KR1020077001315A patent/KR20070036137A/ko not_active Ceased
- 2005-06-21 UA UAA200700276A patent/UA87691C2/ru unknown
- 2005-06-21 WO PCT/EP2005/006712 patent/WO2005123693A1/en not_active Ceased
- 2005-06-21 RU RU2007102223/04A patent/RU2386620C2/ru not_active IP Right Cessation
- 2005-06-21 NZ NZ551284A patent/NZ551284A/en unknown
- 2005-06-21 CN CNA2005800193338A patent/CN1976904A/zh active Pending
- 2005-06-21 TW TW094120704A patent/TW200610757A/zh unknown
- 2005-06-21 JP JP2007517186A patent/JP2008503531A/ja active Pending
- 2005-06-21 EP EP05752744A patent/EP1781621A1/en not_active Withdrawn
- 2005-06-21 AR ARP050102533A patent/AR051738A1/es not_active Application Discontinuation
- 2005-06-21 MX MXPA06014562A patent/MXPA06014562A/es not_active Application Discontinuation
- 2005-06-21 US US11/629,527 patent/US20090029996A1/en not_active Abandoned
- 2005-06-21 SG SG200906269-6A patent/SG155943A1/en unknown
- 2005-06-21 CA CA002570196A patent/CA2570196A1/en not_active Abandoned
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2006
- 2006-11-13 ZA ZA200609399A patent/ZA200609399B/xx unknown
- 2006-11-30 IL IL179741A patent/IL179741A0/en unknown
- 2006-12-08 EC EC2006007057A patent/ECSP067057A/es unknown
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2007
- 2007-01-17 NO NO20070319A patent/NO20070319L/no not_active Application Discontinuation
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