JP2005533024A5 - - Google Patents
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- JP2005533024A5 JP2005533024A5 JP2004505346A JP2004505346A JP2005533024A5 JP 2005533024 A5 JP2005533024 A5 JP 2005533024A5 JP 2004505346 A JP2004505346 A JP 2004505346A JP 2004505346 A JP2004505346 A JP 2004505346A JP 2005533024 A5 JP2005533024 A5 JP 2005533024A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- acetyl
- ethyl
- phenylpyridazin
- phenyl
- 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 cyano, difluoromethoxy Chemical group 0.000 claims description 91
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 29
- 125000001424 substituent group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 22
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 17
- 125000004414 alkyl thio group Chemical group 0.000 claims description 15
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 125000004442 acylamino group Chemical group 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 7
- VROMXVIODDASTK-UHFFFAOYSA-N 5-amino-1h-pyridazin-6-one Chemical class NC1=CC=NNC1=O VROMXVIODDASTK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 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 5
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 5
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 230000005764 inhibitory process Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- PXINPBFBXVDMMC-UHFFFAOYSA-N 2-ethyl-5-(2-ethylbutanoyl)-4-(3-fluoroanilino)-6-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=CC(SC)=CC=2)C(C(=O)C(CC)CC)=C1NC1=CC=CC(F)=C1 PXINPBFBXVDMMC-UHFFFAOYSA-N 0.000 claims description 2
- PNRNDNPESUNOLE-UHFFFAOYSA-N 2-ethyl-5-(2-ethylbutanoyl)-6-(4-methylsulfanylphenyl)-4-(naphthalen-1-ylamino)pyridazin-3-one Chemical compound CCC(CC)C(=O)C1=C(NC=2C3=CC=CC=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=C(SC)C=C1 PNRNDNPESUNOLE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- GTJBUBGAMVZLAE-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(2-methoxyanilino)-6-(4-methylsulfinylphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C(=CC=CC=2)OC)C(=O)N(CC)N=C1C1=CC=C(S(C)=O)C=C1 GTJBUBGAMVZLAE-UHFFFAOYSA-N 0.000 claims description 2
- QSDUGPFIFZEJQV-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(2-methoxyanilino)-6-phenylpyridazin-3-one 5-acetyl-2-ethyl-4-(naphthalen-1-ylamino)-6-phenylpyridazin-3-one Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC=CC2=CC=CC=C12.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=C(C=CC=C1)OC QSDUGPFIFZEJQV-UHFFFAOYSA-N 0.000 claims description 2
- ORTTWVNNFJVMBD-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(3-methoxyanilino)-6-(4-methylsulfinylphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=C(OC)C=CC=2)C(=O)N(CC)N=C1C1=CC=C(S(C)=O)C=C1 ORTTWVNNFJVMBD-UHFFFAOYSA-N 0.000 claims description 2
- GOTRFKPRTIEMCF-UHFFFAOYSA-N 5-acetyl-4-(3,5-dichloro-n-(3,5-dichlorophenyl)anilino)-2-ethyl-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(N(C=2C=C(Cl)C=C(Cl)C=2)C=2C=C(Cl)C=C(Cl)C=2)C(=O)N(CC)N=C1C1=CC=CC=C1 GOTRFKPRTIEMCF-UHFFFAOYSA-N 0.000 claims description 2
- IMUNEGDGHFJVHG-UHFFFAOYSA-N 5-acetyl-4-(3-acetylanilino)-2-ethyl-6-phenylpyridazin-3-one 2-[4-[(5-acetyl-2-ethyl-3-oxo-6-phenylpyridazin-4-yl)amino]phenyl]acetic acid Chemical compound CCn1nc(-c2ccccc2)c(C(C)=O)c(Nc2cccc(c2)C(C)=O)c1=O.CCn1nc(-c2ccccc2)c(C(C)=O)c(Nc2ccc(CC(O)=O)cc2)c1=O IMUNEGDGHFJVHG-UHFFFAOYSA-N 0.000 claims description 2
- PGBIMMPETMLNPG-UHFFFAOYSA-N 5-acetyl-4-(3-chloroanilino)-2,6-diphenylpyridazin-3-one;5-acetyl-4-(3,5-difluoroanilino)-2,6-diphenylpyridazin-3-one Chemical compound O=C1C(NC=2C=C(Cl)C=CC=2)=C(C(=O)C)C(C=2C=CC=CC=2)=NN1C1=CC=CC=C1.O=C1N(C=2C=CC=CC=2)N=C(C=2C=CC=CC=2)C(C(=O)C)=C1NC1=CC(F)=CC(F)=C1 PGBIMMPETMLNPG-UHFFFAOYSA-N 0.000 claims description 2
- IGHUAIVNQCPLHM-UHFFFAOYSA-N 5-acetyl-6-(3-cyclopentyloxy-4-methoxyphenyl)-2-ethyl-4-(3-fluoroanilino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=C(F)C=CC=2)C(=O)N(CC)N=C1C(C=1)=CC=C(OC)C=1OC1CCCC1 IGHUAIVNQCPLHM-UHFFFAOYSA-N 0.000 claims description 2
- AZJVYKVJKKOCMQ-UHFFFAOYSA-N 5-butanoyl-2-ethyl-4-(3-fluoroanilino)-6-(4-methylsulfanylphenyl)pyridazin-3-one Chemical compound O=C1N(CC)N=C(C=2C=CC(SC)=CC=2)C(C(=O)CCC)=C1NC1=CC=CC(F)=C1 AZJVYKVJKKOCMQ-UHFFFAOYSA-N 0.000 claims description 2
- KILMWYKRIUZJHI-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)F)CC)=O)NC1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)F)CC)=O)NC1=CC(=CC=C1)F Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)F)CC)=O)NC1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)F)CC)=O)NC1=CC(=CC=C1)F KILMWYKRIUZJHI-UHFFFAOYSA-N 0.000 claims description 2
- IYQFDCVWMUYQBM-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)[N+](=O)[O-])CC)=O)NC1=CC(=CC=C1)Br.C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)[N+](=O)[O-])CC)=O)NC1=CC=C(C(=O)O)C=C1 Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)[N+](=O)[O-])CC)=O)NC1=CC(=CC=C1)Br.C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)[N+](=O)[O-])CC)=O)NC1=CC=C(C(=O)O)C=C1 IYQFDCVWMUYQBM-UHFFFAOYSA-N 0.000 claims description 2
- YEXVBAGSTJLBHX-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC=C(C=C1)SC)CC)=O)NC1=CC=CC2=CC=CC=C12.C(C)(=O)C1=C(C(N(N=C1C1=CC=C(C=C1)SC)CC)=O)NC1=CC=C(C(=O)O)C=C1 Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=C(C=C1)SC)CC)=O)NC1=CC=CC2=CC=CC=C12.C(C)(=O)C1=C(C(N(N=C1C1=CC=C(C=C1)SC)CC)=O)NC1=CC=C(C(=O)O)C=C1 YEXVBAGSTJLBHX-UHFFFAOYSA-N 0.000 claims description 2
- BFTQBTFUCYQGKB-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)N(C1=CC(=CC=C1)Cl)C1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)N(C1=CC(=CC=C1)F)C1=CC(=CC=C1)F Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)N(C1=CC(=CC=C1)Cl)C1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)N(C1=CC(=CC=C1)F)C1=CC(=CC=C1)F BFTQBTFUCYQGKB-UHFFFAOYSA-N 0.000 claims description 2
- HBUMKFOVTJTPCX-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC1CC1)=O)NC1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC1CC1)=O)NC1=CC(=CC=C1)F Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC1CC1)=O)NC1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC1CC1)=O)NC1=CC(=CC=C1)F HBUMKFOVTJTPCX-UHFFFAOYSA-N 0.000 claims description 2
- MJYQSPCVOAAJHS-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CCCC)=O)NC1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CCC)=O)NC1=CC(=CC=C1)Cl Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CCCC)=O)NC1=CC(=CC=C1)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CCC)=O)NC1=CC(=CC=C1)Cl MJYQSPCVOAAJHS-UHFFFAOYSA-N 0.000 claims description 2
- GCRIJTOXXPSYRT-UHFFFAOYSA-N ClC=1C=C(C=CC1)NC1=C(C(=NN(C1=O)CC)C1=CC=CC=C1)C=O.C(C1=CC=CC=C1)(=O)C1=C(C(N(N=C1C)CC)=O)NC1=CC(=CC=C1)Cl Chemical compound ClC=1C=C(C=CC1)NC1=C(C(=NN(C1=O)CC)C1=CC=CC=C1)C=O.C(C1=CC=CC=C1)(=O)C1=C(C(N(N=C1C)CC)=O)NC1=CC(=CC=C1)Cl GCRIJTOXXPSYRT-UHFFFAOYSA-N 0.000 claims description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229940095102 methyl benzoate Drugs 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Chemical group 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 4
- 125000004663 dialkyl amino group Chemical group 0.000 claims 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
- QKLJQAOPWOHVAM-UHFFFAOYSA-N 4-[[5-acetyl-2-ethyl-6-(4-methylsulfanylphenyl)-3-oxopyridazin-4-yl]amino]benzoic acid Chemical compound CC(=O)C1=C(NC=2C=CC(=CC=2)C(O)=O)C(=O)N(CC)N=C1C1=CC=C(SC)C=C1 QKLJQAOPWOHVAM-UHFFFAOYSA-N 0.000 claims 1
- ZAWIPHOFTWJJOS-UHFFFAOYSA-N 4-acetyl-5-(3-chloroanilino)-3-phenyl-1h-pyridazin-6-one Chemical compound CC(=O)C=1C(C=2C=CC=CC=2)=NNC(=O)C=1NC1=CC=CC(Cl)=C1 ZAWIPHOFTWJJOS-UHFFFAOYSA-N 0.000 claims 1
- PYSDBLJXOCDXRH-UHFFFAOYSA-N 5-(3-cyanoanilino)-1-ethyl-6-oxo-3-phenylpyridazine-4-carboxamide;5-(3-cyanoanilino)-1-ethyl-6-oxo-3-phenylpyridazine-4-carboxylic acid Chemical compound NC(=O)C1=C(NC=2C=C(C=CC=2)C#N)C(=O)N(CC)N=C1C1=CC=CC=C1.OC(=O)C1=C(NC=2C=C(C=CC=2)C#N)C(=O)N(CC)N=C1C1=CC=CC=C1 PYSDBLJXOCDXRH-UHFFFAOYSA-N 0.000 claims 1
- SYIJJNUNOAXWHT-UHFFFAOYSA-N 5-acetyl-2-(cyclopropylmethyl)-4-(3,5-difluoroanilino)-6-phenylpyridazin-3-one Chemical compound O=C1N(CC2CC2)N=C(C=2C=CC=CC=2)C(C(=O)C)=C1NC1=CC(F)=CC(F)=C1 SYIJJNUNOAXWHT-UHFFFAOYSA-N 0.000 claims 1
- YGBOHWNHVJFPAU-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(2-methylanilino)-6-(4-methylsulfinylphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C(=CC=CC=2)C)C(=O)N(CC)N=C1C1=CC=C(S(C)=O)C=C1 YGBOHWNHVJFPAU-UHFFFAOYSA-N 0.000 claims 1
- IADBPRKUZVCLLE-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(3-hydroxy-4-methoxyanilino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=C(O)C(OC)=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 IADBPRKUZVCLLE-UHFFFAOYSA-N 0.000 claims 1
- QRAHDPXJBHBZSK-UHFFFAOYSA-N 5-acetyl-4-(2-chloroanilino)-2-ethyl-6-phenylpyridazin-3-one;5-acetyl-2-ethyl-4-(naphthalen-1-ylamino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C(=CC=CC=2)Cl)C(=O)N(CC)N=C1C1=CC=CC=C1.CC(=O)C1=C(NC=2C3=CC=CC=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 QRAHDPXJBHBZSK-UHFFFAOYSA-N 0.000 claims 1
- LRARSWDTAKYIPI-UHFFFAOYSA-N 5-acetyl-4-(3,4-dimethoxyanilino)-2-ethyl-6-phenylpyridazin-3-one 5-acetyl-2-ethyl-4-[4-(hydroxymethyl)anilino]-6-phenylpyridazin-3-one Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC=C(C=C1)CO.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=C(C=C1)OC)OC LRARSWDTAKYIPI-UHFFFAOYSA-N 0.000 claims 1
- PGTMPDTZRXCDCP-UHFFFAOYSA-N 5-acetyl-4-(3-chloro-4-methoxyanilino)-2-ethyl-6-phenylpyridazin-3-one 5-acetyl-2-ethyl-6-phenyl-4-[3-(trifluoromethyl)anilino]pyridazin-3-one Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=C(C=C1)OC)Cl.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=CC=C1)C(F)(F)F PGTMPDTZRXCDCP-UHFFFAOYSA-N 0.000 claims 1
- ADAGYJGTWJPBKY-UHFFFAOYSA-N 5-acetyl-6-(3-cyclopentyloxy-4-methoxyphenyl)-2-ethyl-4-(naphthalen-1-ylamino)pyridazin-3-one;5-acetyl-2-methyl-4-(naphthalen-1-ylamino)-6-phenylpyridazin-3-one Chemical compound N=1N(C)C(=O)C(NC=2C3=CC=CC=C3C=CC=2)=C(C(=O)C)C=1C1=CC=CC=C1.CC(=O)C1=C(NC=2C3=CC=CC=C3C=CC=2)C(=O)N(CC)N=C1C(C=1)=CC=C(OC)C=1OC1CCCC1 ADAGYJGTWJPBKY-UHFFFAOYSA-N 0.000 claims 1
- ANLZZGTWBDRRPB-UHFFFAOYSA-N 5-nitro-1h-pyridazin-6-one Chemical class [O-][N+](=O)C1=CC=NNC1=O ANLZZGTWBDRRPB-UHFFFAOYSA-N 0.000 claims 1
- UASSRZYLOUJSRH-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)[N+](=O)[O-])CC)=O)NC1=CC=CC2=CC=CC=C12.C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)F)CC)=O)NC1=CC(=CC=C1)Cl Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)[N+](=O)[O-])CC)=O)NC1=CC=CC2=CC=CC=C12.C(C)(=O)C1=C(C(N(N=C1C1=CC(=CC=C1)F)CC)=O)NC1=CC(=CC=C1)Cl UASSRZYLOUJSRH-UHFFFAOYSA-N 0.000 claims 1
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- VQVZHJUGXYQZLU-UHFFFAOYSA-N C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=CC=C1)Br.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=CC=C1)Cl Chemical compound C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=CC=C1)Br.C(C)(=O)C1=C(C(N(N=C1C1=CC=CC=C1)CC)=O)NC1=CC(=CC=C1)Cl VQVZHJUGXYQZLU-UHFFFAOYSA-N 0.000 claims 1
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| RU (1) | RU2326869C2 (https=) |
| TW (1) | TWI309981B (https=) |
| UA (1) | UA77532C2 (https=) |
| UY (1) | UY27807A1 (https=) |
| WO (1) | WO2003097613A1 (https=) |
| ZA (1) | ZA200409173B (https=) |
Families Citing this family (62)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7214687B2 (en) | 1999-07-14 | 2007-05-08 | Almirall Ag | Quinuclidine derivatives and medicinal compositions containing the same |
| ES2165768B1 (es) | 1999-07-14 | 2003-04-01 | Almirall Prodesfarma Sa | Nuevos derivados de quinuclidina y composiciones farmaceuticas que los contienen. |
| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| CN1938296A (zh) * | 2004-04-01 | 2007-03-28 | 安斯泰来制药有限公司 | 作为腺苷拮抗剂的吡嗪衍生物及其制药用途 |
| BRPI0510486A (pt) * | 2004-05-19 | 2007-11-20 | Basf Ag | composto, processo para preparar o mesmo, agente pesticida, e, processo para combater fungos nocivos fitopatogênicos |
| ATE474601T1 (de) | 2004-05-31 | 2010-08-15 | Almirall Sa | Kombinationen mit antimuskarin-wirkstoffen und pde4-hemmern |
| 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. |
| 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. |
| AU2008219166B2 (en) * | 2007-02-16 | 2013-05-16 | Amgen Inc. | Nitrogen-containing heterocyclyl ketones and their use as c-Met inhibitors |
| 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. |
| 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 |
| EP2226323A1 (en) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | New tetrahydropyrazolo[3,4-c]isoquinolin-5-amine derivatives |
| 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 |
| 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 |
| EP2380890A1 (en) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 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 |
| EP2518070A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Pyrrolotriazinone derivatives as PI3K inhibitors |
| EP2518071A1 (en) | 2011-04-29 | 2012-10-31 | Almirall, S.A. | Imidazopyridine 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. |
| 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 |
| WO2013097052A1 (en) | 2011-12-30 | 2013-07-04 | Abbott Laboratories | Bromodomain inhibitors |
| 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 |
| EP2848615A1 (en) | 2013-07-03 | 2015-03-18 | Almirall, S.A. | New pyrazole derivatives as CRAC channel modulators |
| EP3290407B1 (en) | 2013-10-18 | 2020-01-01 | Celgene Quanticel Research, Inc | Bromodomain inhibitors |
| CA3018802A1 (en) | 2016-04-15 | 2017-10-19 | Abbvie Inc. | Bromodomain inhibitors |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HUT66969A (en) | 1991-10-09 | 1995-01-30 | Syntex Inc | Benzo- and pyrido-pyridazinone- and pyridazin-thion derivatives, pharmaceutical compositions containing the same and process for the production of thereof |
| EP0742211B1 (en) * | 1994-01-25 | 2000-05-10 | Nissan Chemical Industries, Limited | Pyridazinone derivatives |
| 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 |
| 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 |
| NZ522882A (en) * | 2000-06-05 | 2004-07-30 | Altana Pharma Bv | Pyridazinone compounds effective as beta-2-adrenoreceptor agonists as well as PDE4-inhibitors |
| US6699890B2 (en) | 2000-12-22 | 2004-03-02 | Memory Pharmaceuticals Corp. | Phosphodiesterase 4 inhibitors |
-
2002
- 2002-05-16 ES ES200201111A patent/ES2195785B1/es not_active Expired - Fee Related
-
2003
- 2003-05-14 EP EP03735387A patent/EP1503992A1/en not_active Withdrawn
- 2003-05-14 UA UA20041210293A patent/UA77532C2/uk unknown
- 2003-05-14 AU AU2003236648A patent/AU2003236648A1/en not_active Abandoned
- 2003-05-14 CN CNB03816342XA patent/CN1324014C/zh not_active Expired - Fee Related
- 2003-05-14 US US10/513,219 patent/US7459453B2/en not_active Expired - Fee Related
- 2003-05-14 CA CA002485896A patent/CA2485896A1/en not_active Abandoned
- 2003-05-14 MX MXPA04011209A patent/MXPA04011209A/es active IP Right Grant
- 2003-05-14 PE PE2003000462A patent/PE20040689A1/es not_active Application Discontinuation
- 2003-05-14 RU RU2004136977/04A patent/RU2326869C2/ru not_active IP Right Cessation
- 2003-05-14 WO PCT/EP2003/005056 patent/WO2003097613A1/en not_active Ceased
- 2003-05-14 NZ NZ536604A patent/NZ536604A/en unknown
- 2003-05-14 KR KR10-2004-7018292A patent/KR20040106536A/ko not_active Ceased
- 2003-05-14 JP JP2004505346A patent/JP2005533024A/ja active Pending
- 2003-05-14 BR BR0310106-1A patent/BR0310106A/pt not_active IP Right Cessation
- 2003-05-14 UY UY27807A patent/UY27807A1/es not_active Application Discontinuation
- 2003-05-15 AR ARP030101684A patent/AR040076A1/es unknown
- 2003-05-16 TW TW092113343A patent/TWI309981B/zh not_active IP Right Cessation
- 2003-05-16 MY MYPI20031820A patent/MY132106A/en unknown
-
2004
- 2004-11-05 EC EC2004005410A patent/ECSP045410A/es unknown
- 2004-11-11 ZA ZA200409173A patent/ZA200409173B/en unknown
- 2004-11-11 IL IL16517304A patent/IL165173A0/xx unknown
- 2004-12-15 NO NO20045461A patent/NO20045461L/no not_active Application Discontinuation
-
2008
- 2008-06-18 US US12/141,712 patent/US20080269235A1/en not_active Abandoned
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