RU2376293C2 - Производные пиридазин-3(2h)-она и их применение в качестве ингибиторов фдэ4 - Google Patents
Производные пиридазин-3(2h)-она и их применение в качестве ингибиторов фдэ4 Download PDFInfo
- Publication number
- RU2376293C2 RU2376293C2 RU2007101654/04A RU2007101654A RU2376293C2 RU 2376293 C2 RU2376293 C2 RU 2376293C2 RU 2007101654/04 A RU2007101654/04 A RU 2007101654/04A RU 2007101654 A RU2007101654 A RU 2007101654A RU 2376293 C2 RU2376293 C2 RU 2376293C2
- Authority
- RU
- Russia
- Prior art keywords
- ethyl
- carboxylate
- oxo
- dihydropyridazin
- ylamino
- Prior art date
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 10
- 201000010099 disease Diseases 0.000 claims abstract 8
- 230000001575 pathological effect Effects 0.000 claims abstract 8
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract 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 abstract 6
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims abstract 6
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract 6
- 125000004429 atom Chemical group 0.000 claims abstract 5
- 230000005764 inhibitory process Effects 0.000 claims abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 5
- 230000002265 prevention Effects 0.000 claims abstract 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims abstract 4
- 206010012438 Dermatitis atopic Diseases 0.000 claims abstract 4
- 201000004681 Psoriasis Diseases 0.000 claims abstract 4
- 208000006673 asthma Diseases 0.000 claims abstract 4
- 201000008937 atopic dermatitis Diseases 0.000 claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 4
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 125000004076 pyridyl group Chemical group 0.000 claims abstract 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 3
- 125000001544 thienyl group Chemical group 0.000 claims abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 239000000048 adrenergic agonist Substances 0.000 claims abstract 2
- 239000005557 antagonist Substances 0.000 claims abstract 2
- 208000035475 disorder Diseases 0.000 claims abstract 2
- 239000003814 drug Substances 0.000 claims abstract 2
- 229940125721 immunosuppressive agent Drugs 0.000 claims abstract 2
- 239000003018 immunosuppressive agent Substances 0.000 claims abstract 2
- 125000005956 isoquinolyl group Chemical group 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000005493 quinolyl group Chemical group 0.000 claims abstract 2
- 150000003431 steroids Chemical class 0.000 claims abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000005843 halogen group Chemical group 0.000 claims 4
- 208000002551 irritable bowel syndrome Diseases 0.000 claims 3
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 2
- 125000003342 alkenyl group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- -1 isoquinolin-4-ylamino Chemical group 0.000 claims 2
- DUGLNILOHLZOSC-UHFFFAOYSA-N 1-ethyl-4-[(3-methoxyphenyl)methyl]-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylic acid Chemical compound C=1N=CC=C(C)C=1NC=1C(=O)N(CC)N=C(C(O)=O)C=1CC1=CC=CC(OC)=C1 DUGLNILOHLZOSC-UHFFFAOYSA-N 0.000 claims 1
- DFFBITOYBFEFIR-UHFFFAOYSA-N 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-4-(1-pyridin-4-ylethyl)pyridazine-3-carboxylic acid Chemical compound C=1N=CC2=CC=CC=C2C=1NC=1C(=O)N(CC)N=C(C(O)=O)C=1C(C)C1=CC=NC=C1 DFFBITOYBFEFIR-UHFFFAOYSA-N 0.000 claims 1
- KHTROZMCKMAICL-UHFFFAOYSA-N 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxo-4-(1-pyridin-4-ylethyl)pyridazine-3-carboxylic acid Chemical compound C=1N=CC=C(C)C=1NC=1C(=O)N(CC)N=C(C(O)=O)C=1C(C)C1=CC=NC=C1 KHTROZMCKMAICL-UHFFFAOYSA-N 0.000 claims 1
- POKGEXKSJVTVPY-UHFFFAOYSA-N 1-ethyl-6-oxo-5-(pyridin-3-ylamino)-4-(1-pyridin-4-ylethyl)pyridazine-3-carboxylic acid Chemical compound C=1C=CN=CC=1NC=1C(=O)N(CC)N=C(C(O)=O)C=1C(C)C1=CC=NC=C1 POKGEXKSJVTVPY-UHFFFAOYSA-N 0.000 claims 1
- ZLVYFZKDGSBWLH-UHFFFAOYSA-N 1-phenylethyl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC(C)C1=CC=CC=C1 ZLVYFZKDGSBWLH-UHFFFAOYSA-N 0.000 claims 1
- JMSHQRQIKGQOKW-UHFFFAOYSA-N 1-phenylethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)C=2C=CC=CC=2)C=C1NC1=CN=CC=C1C JMSHQRQIKGQOKW-UHFFFAOYSA-N 0.000 claims 1
- HCITYDRGAUSHMA-UHFFFAOYSA-N 1-phenylethyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC(C)C1=CC=CC=C1 HCITYDRGAUSHMA-UHFFFAOYSA-N 0.000 claims 1
- BWQLDNNFADPVJI-UHFFFAOYSA-N 1-phenylethyl 4-acetyl-1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C(=O)OC(C)C1=CC=CC=C1 BWQLDNNFADPVJI-UHFFFAOYSA-N 0.000 claims 1
- UXBWUANOUDOKAX-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-yl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound C1CC2=CC=CC=C2C1OC(=O)C1=NN(CC)C(=O)C(NC=2C3=CC=CC=C3C=NC=2)=C1 UXBWUANOUDOKAX-UHFFFAOYSA-N 0.000 claims 1
- YBAFRKFYYVKMNM-UHFFFAOYSA-N 2,3-dihydro-1h-inden-1-yl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC2C3=CC=CC=C3CC2)C=C1NC1=CN=CC=C1C YBAFRKFYYVKMNM-UHFFFAOYSA-N 0.000 claims 1
- CDDBIRVXFASTJN-UHFFFAOYSA-N 2-methoxyethyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCCOC)C(C(C)=O)=C1NC1=CC=CN=C1 CDDBIRVXFASTJN-UHFFFAOYSA-N 0.000 claims 1
- SDBZZUKSQDHPAK-UHFFFAOYSA-N 2-phenylethyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C(=O)OCCC1=CC=CC=C1 SDBZZUKSQDHPAK-UHFFFAOYSA-N 0.000 claims 1
- WNDXHGSRBTYYGX-UHFFFAOYSA-N 3-methylbutyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCCC(C)C)C(C(C)=O)=C1NC1=CC=CN=C1 WNDXHGSRBTYYGX-UHFFFAOYSA-N 0.000 claims 1
- RLLQYENNUBQCTN-UHFFFAOYSA-N 4-[(3-chlorophenyl)methyl]-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylic acid Chemical compound C=1N=CC2=CC=CC=C2C=1NC=1C(=O)N(CC)N=C(C(O)=O)C=1CC1=CC=CC(Cl)=C1 RLLQYENNUBQCTN-UHFFFAOYSA-N 0.000 claims 1
- DCPHRBXAWXQBTG-UHFFFAOYSA-N 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-2-(1-methoxy-1-oxopropan-2-yl)-6-oxo-3H-pyridazine-3-carboxylic acid Chemical compound CCN1C(=O)C(=C(C(N1C(C)C(=O)OC)C(=O)O)C(=O)C)NC2=CN=CC3=CC=CC=C32 DCPHRBXAWXQBTG-UHFFFAOYSA-N 0.000 claims 1
- ONYMQTLURCUBOY-UHFFFAOYSA-N 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-2-(1-phenylpropan-2-yl)-3H-pyridazine-3-carboxylic acid Chemical compound CCN1C(=O)C(=C(C(N1C(C)CC2=CC=CC=C2)C(=O)O)C(=O)C)NC3=CN=CC4=CC=CC=C43 ONYMQTLURCUBOY-UHFFFAOYSA-N 0.000 claims 1
- RVBQQBXFEGTHGV-UHFFFAOYSA-N 4-acetyl-2-[2-(dimethylamino)-2-oxoethyl]-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxo-3H-pyridazine-3-carboxylic acid Chemical compound CCN1C(=O)C(=C(C(N1CC(=O)N(C)C)C(=O)O)C(=O)C)NC2=CN=CC3=CC=CC=C32 RVBQQBXFEGTHGV-UHFFFAOYSA-N 0.000 claims 1
- 102000007202 Muscarinic M3 Receptor Human genes 0.000 claims 1
- 108010008405 Muscarinic M3 Receptor Proteins 0.000 claims 1
- 108091008874 T cell receptors Proteins 0.000 claims 1
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 1
- 229940124599 anti-inflammatory drug Drugs 0.000 claims 1
- QIRAQGGRQBGLDC-UHFFFAOYSA-N benzyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCC=2C=CC=CC=2)C=C1NC1=CN=CC=C1C QIRAQGGRQBGLDC-UHFFFAOYSA-N 0.000 claims 1
- LIDVWJYQIRVQSQ-UHFFFAOYSA-N benzyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OCC1=CC=CC=C1 LIDVWJYQIRVQSQ-UHFFFAOYSA-N 0.000 claims 1
- OLOHVDMVFNFNOW-UHFFFAOYSA-N benzyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C(=O)OCC1=CC=CC=C1 OLOHVDMVFNFNOW-UHFFFAOYSA-N 0.000 claims 1
- BCTIUOAMRBQOSL-UHFFFAOYSA-N butan-2-yl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CCC(C)OC(=O)C1=NN(CC)C(=O)C(NC=2C3=CC=CC=C3C=NC=2)=C1C(C)=O BCTIUOAMRBQOSL-UHFFFAOYSA-N 0.000 claims 1
- JXKWUDNZEPRUSE-UHFFFAOYSA-N cyclobutyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC1CCC1 JXKWUDNZEPRUSE-UHFFFAOYSA-N 0.000 claims 1
- MIYFJKWOMVWEKZ-UHFFFAOYSA-N cyclohexyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OC1CCCCC1 MIYFJKWOMVWEKZ-UHFFFAOYSA-N 0.000 claims 1
- VUOWFCSQQKDDMX-UHFFFAOYSA-N cyclohexyl 4-acetyl-1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C(=CC=NC=2)C)C(=O)N(CC)N=C1C(=O)OC1CCCCC1 VUOWFCSQQKDDMX-UHFFFAOYSA-N 0.000 claims 1
- JSASAAWXXZOLNE-UHFFFAOYSA-N cyclopropylmethyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C(=O)OCC1CC1 JSASAAWXXZOLNE-UHFFFAOYSA-N 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- GCXXYWUKFPXDBF-UHFFFAOYSA-N ethyl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCC)C=C1NC1=CN=CC2=CC=CC=C12 GCXXYWUKFPXDBF-UHFFFAOYSA-N 0.000 claims 1
- NAPWKYMJQQVNHP-UHFFFAOYSA-N ethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCC)C=C1NC1=CN=CC=C1C NAPWKYMJQQVNHP-UHFFFAOYSA-N 0.000 claims 1
- NPZYMUJSBMSKNZ-UHFFFAOYSA-N ethyl 1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCC)C=C1NC1=CC=CN=C1 NPZYMUJSBMSKNZ-UHFFFAOYSA-N 0.000 claims 1
- MVSZFEUWZYJFRG-UHFFFAOYSA-N ethyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound CCOC(=O)C1=NN(CC)C(=O)C(NC=2C3=CC=CC=C3C=NC=2)=C1C(C)=O MVSZFEUWZYJFRG-UHFFFAOYSA-N 0.000 claims 1
- XOTNULUUSWDFLS-UHFFFAOYSA-N ethyl 4-acetyl-1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound CCOC(=O)C1=NN(CC)C(=O)C(NC=2C(=CC=NC=2)C)=C1C(C)=O XOTNULUUSWDFLS-UHFFFAOYSA-N 0.000 claims 1
- FMLZDRFBZRLZSS-UHFFFAOYSA-N ethyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound CCOC(=O)C1=NN(CC)C(=O)C(NC=2C=NC=CC=2)=C1C(C)=O FMLZDRFBZRLZSS-UHFFFAOYSA-N 0.000 claims 1
- YQKBYSMUTSSLKW-UHFFFAOYSA-N ethyl 4-acetyl-1-ethyl-6-oxo-5-(quinolin-5-ylamino)pyridazine-3-carboxylate Chemical compound CCOC(=O)C1=NN(CC)C(=O)C(NC=2C3=CC=CN=C3C=CC=2)=C1C(C)=O YQKBYSMUTSSLKW-UHFFFAOYSA-N 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940126601 medicinal product Drugs 0.000 claims 1
- SQIDRVYHXSXDEQ-UHFFFAOYSA-N methyl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC)C(C(C)=O)=C1NC1=CC=CN=C1 SQIDRVYHXSXDEQ-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- DMLVYMZOVRESBK-UHFFFAOYSA-N propan-2-yl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)C)C=C1NC1=CN=CC=C1C DMLVYMZOVRESBK-UHFFFAOYSA-N 0.000 claims 1
- BHFJMINGVKTLED-UHFFFAOYSA-N propan-2-yl 1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)C)C=C1NC1=CC=CN=C1 BHFJMINGVKTLED-UHFFFAOYSA-N 0.000 claims 1
- FRRHUYSSLWNWOX-UHFFFAOYSA-N propan-2-yl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)C)C(C(C)=O)=C1NC1=CN=CC2=CC=CC=C12 FRRHUYSSLWNWOX-UHFFFAOYSA-N 0.000 claims 1
- KWCIIQXQXVLRBZ-UHFFFAOYSA-N propan-2-yl 4-acetyl-1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)C)C(C(C)=O)=C1NC1=CC=CN=C1 KWCIIQXQXVLRBZ-UHFFFAOYSA-N 0.000 claims 1
- GCCMWJXOFLMCBL-UHFFFAOYSA-N pyridin-2-ylmethyl 1-ethyl-6-oxo-5-(pyridin-3-ylamino)pyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCC=2N=CC=CC=2)C=C1NC1=CC=CN=C1 GCCMWJXOFLMCBL-UHFFFAOYSA-N 0.000 claims 1
- XBBKQMIXNNKAQD-UHFFFAOYSA-N tert-butyl 4-acetyl-1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)(C)C)C(C(C)=O)=C1NC1=CN=CC2=CC=CC=C12 XBBKQMIXNNKAQD-UHFFFAOYSA-N 0.000 claims 1
- PIEOKTWZXKYLAB-UHFFFAOYSA-N tert-butyl 4-acetyl-1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OC(C)(C)C)C(C(C)=O)=C1NC1=CN=CC=C1C PIEOKTWZXKYLAB-UHFFFAOYSA-N 0.000 claims 1
- VCHODBNJCGDHKC-UHFFFAOYSA-N thiophen-3-ylmethyl 1-ethyl-5-(isoquinolin-4-ylamino)-6-oxopyridazine-3-carboxylate Chemical compound C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C(=O)OCC=1C=CSC=1 VCHODBNJCGDHKC-UHFFFAOYSA-N 0.000 claims 1
- BBVAEFMUWAYHAL-UHFFFAOYSA-N thiophen-3-ylmethyl 1-ethyl-5-[(4-methylpyridin-3-yl)amino]-6-oxopyridazine-3-carboxylate Chemical compound O=C1N(CC)N=C(C(=O)OCC2=CSC=C2)C=C1NC1=CN=CC=C1C BBVAEFMUWAYHAL-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- PQNFLJBBNBOBRQ-UHFFFAOYSA-N indane Chemical compound C1=CC=C2CCCC2=C1 PQNFLJBBNBOBRQ-UHFFFAOYSA-N 0.000 abstract 2
- 229940124639 Selective inhibitor Drugs 0.000 abstract 1
- 210000001744 T-lymphocyte Anatomy 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000004966 cyanoalkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000001629 suppression Effects 0.000 abstract 1
- 208000011580 syndromic disease Diseases 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
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| ES2211344B1 (es) * | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US7517994B2 (en) * | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7732616B2 (en) * | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
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| 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. |
| KR20080019236A (ko) * | 2005-05-18 | 2008-03-03 | 어레이 바이오파마 인크. | Ｍｅｋ의 헤테로시클릭 억제제 및 그의 사용 방법 |
| 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. |
| 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 |
| 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. |
| 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. |
| SI2148873T1 (sl) | 2007-04-23 | 2013-01-31 | Janssen Pharmaceutica, N.V. | Derivati 4-alkoksipiridazina kot antagonisti receptorja dopamina 2 s hitro disociacijo |
| ES2400710T3 (es) | 2007-04-23 | 2013-04-11 | Janssen Pharmaceutica, N.V. | Tia(dia)zoles como antagonistas del receptor de dopamina 2 de disociación rápida |
| 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 |
| 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 |
| 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 |
| US8895562B2 (en) | 2008-07-31 | 2014-11-25 | Janssen Pharmaceutica Nv | Piperazin-1-yl-trifluoromethyl-substituted-pyridines as fast dissociating dopamine 2 receptor antagonists |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| EP2386555A1 (en) | 2010-05-13 | 2011-11-16 | Almirall, S.A. | New cyclohexylamine derivatives having beta2 adrenergic agonist and m3 muscarinic antagonist activities |
| 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 |
| 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 |
| WO2014060431A1 (en) | 2012-10-16 | 2014-04-24 | Almirall, S.A. | Pyrrolotriazinone derivatives as pi3k inhibitors |
| KR101282885B1 (ko) * | 2012-11-14 | 2013-07-05 | 한국원자력연구원 | 스티릴피리다진온 유도체를 이용한 아밀로이드 단백질 응집물의 검출 방법 |
| EP2738172A1 (en) | 2012-11-28 | 2014-06-04 | Almirall, S.A. | New bicyclic compounds as crac channel modulators |
| DK2931275T3 (da) | 2012-12-17 | 2022-07-04 | Almirall Sa | Aclidinium til anvendelse i øgning af fysisk aktivitet i hverdagen hos en patient, der lider af kronisk, obstruktiv lungesygdom |
| HK1215166A1 (zh) | 2012-12-18 | 2016-08-19 | Almirall, S.A. | 具有β2肾上腺素激动剂及M3毒蕈碱拮抗剂活性的新型环己基和奎宁环基氨基甲酸酯衍生物 |
| UY35332A (es) | 2013-02-15 | 2014-11-28 | 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 |
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| RU2182574C2 (ru) * | 1995-06-20 | 2002-05-20 | Зенека Лимитед | Ароматические соединения и содержащие их фармацевтические композиции |
| RU2198878C2 (ru) * | 1995-06-20 | 2003-02-20 | Зенека Лимитед | Ароматические соединения и содержащие их фармацевтические композиции |
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| RU2232755C2 (ru) * | 1999-02-26 | 2004-07-20 | Кова Ко., Лтд. | Производные пиридазин-3-она и содержащие их лекарственные средства |
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2004
- 2004-06-18 ES ES200401500A patent/ES2251866B1/es not_active Expired - Fee Related
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2005
- 2005-06-13 UY UY28958A patent/UY28958A1/es unknown
- 2005-06-13 AT AT05751683T patent/ATE492538T1/de not_active IP Right Cessation
- 2005-06-13 WO PCT/EP2005/006304 patent/WO2005123692A1/en not_active Ceased
- 2005-06-13 AU AU2005254659A patent/AU2005254659A1/en not_active Abandoned
- 2005-06-13 KR KR1020077001216A patent/KR20070029808A/ko not_active Ceased
- 2005-06-13 BR BRPI0511383-0A patent/BRPI0511383A/pt not_active IP Right Cessation
- 2005-06-13 SG SG200906039-3A patent/SG155909A1/en unknown
- 2005-06-13 MX MXPA06013593A patent/MXPA06013593A/es active IP Right Grant
- 2005-06-13 EP EP05751683A patent/EP1758869B1/en not_active Expired - Lifetime
- 2005-06-13 CA CA002570170A patent/CA2570170A1/en not_active Abandoned
- 2005-06-13 RU RU2007101654/04A patent/RU2376293C2/ru not_active IP Right Cessation
- 2005-06-13 DE DE602005025478T patent/DE602005025478D1/de not_active Expired - Lifetime
- 2005-06-13 ES ES05751683T patent/ES2358335T3/es not_active Expired - Lifetime
- 2005-06-13 UA UAA200700279A patent/UA88472C2/ru unknown
- 2005-06-13 JP JP2007515846A patent/JP2008502628A/ja active Pending
- 2005-06-13 US US11/629,522 patent/US7960383B2/en not_active Expired - Fee Related
- 2005-06-13 CN CNA2005800187731A patent/CN1964952A/zh active Pending
- 2005-06-15 PE PE2005000683A patent/PE20060436A1/es not_active Application Discontinuation
- 2005-06-17 TW TW094120336A patent/TW200612951A/zh unknown
- 2005-06-17 AR ARP050102489A patent/AR049402A1/es not_active Application Discontinuation
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2006
- 2006-11-13 ZA ZA200609403A patent/ZA200609403B/xx unknown
- 2006-11-30 IL IL179734A patent/IL179734A0/en unknown
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- 2007-01-17 NO NO20070321A patent/NO20070321L/no not_active Application Discontinuation
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Also Published As
| Publication number | Publication date |
|---|---|
| US20080280918A1 (en) | 2008-11-13 |
| NO20070321L (no) | 2007-03-12 |
| MXPA06013593A (es) | 2007-03-15 |
| TW200612951A (en) | 2006-05-01 |
| KR20070029808A (ko) | 2007-03-14 |
| ECSP067058A (es) | 2007-03-29 |
| ES2251866A1 (es) | 2006-05-01 |
| ES2358335T3 (es) | 2011-05-09 |
| US7960383B2 (en) | 2011-06-14 |
| AU2005254659A1 (en) | 2005-12-29 |
| AR049402A1 (es) | 2006-07-26 |
| ZA200609403B (en) | 2007-12-27 |
| IL179734A0 (en) | 2007-05-15 |
| EP1758869B1 (en) | 2010-12-22 |
| JP2008502628A (ja) | 2008-01-31 |
| PE20060436A1 (es) | 2006-06-02 |
| UY28958A1 (es) | 2005-08-31 |
| BRPI0511383A (pt) | 2007-12-26 |
| EP1758869A1 (en) | 2007-03-07 |
| WO2005123692A8 (en) | 2006-05-04 |
| ES2251866B1 (es) | 2007-06-16 |
| WO2005123692A1 (en) | 2005-12-29 |
| CN1964952A (zh) | 2007-05-16 |
| UA88472C2 (en) | 2009-10-26 |
| RU2007101654A (ru) | 2008-07-27 |
| SG155909A1 (en) | 2009-10-29 |
| ATE492538T1 (de) | 2011-01-15 |
| CA2570170A1 (en) | 2005-12-29 |
| DE602005025478D1 (de) | 2011-02-03 |
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