UA80016C2 - Pyridazin-3(2h)-one derivates - Google Patents
Pyridazin-3(2h)-one derivates Download PDFInfo
- Publication number
- UA80016C2 UA80016C2 UAA200507288A UA2005007288A UA80016C2 UA 80016 C2 UA80016 C2 UA 80016C2 UA A200507288 A UAA200507288 A UA A200507288A UA 2005007288 A UA2005007288 A UA 2005007288A UA 80016 C2 UA80016 C2 UA 80016C2
- Authority
- UA
- Ukraine
- Prior art keywords
- acetyl
- ethyl
- amino
- pyridin
- ylamino
- Prior art date
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- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 title claims abstract description 126
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 4
- -1 oxo- Chemical class 0.000 claims description 448
- 150000001875 compounds Chemical class 0.000 claims description 298
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 253
- 238000000034 method Methods 0.000 claims description 169
- 125000001424 substituent group Chemical group 0.000 claims description 145
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 90
- 125000004432 carbon atom Chemical group C* 0.000 claims description 81
- 150000003254 radicals Chemical class 0.000 claims description 73
- 125000000217 alkyl group Chemical group 0.000 claims description 70
- 125000003545 alkoxy group Chemical group 0.000 claims description 63
- 125000005843 halogen group Chemical group 0.000 claims description 59
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 48
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 46
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 30
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 28
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 26
- 125000005117 dialkylcarbamoyl group Chemical group 0.000 claims description 26
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 23
- 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 21
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 21
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 21
- 125000002252 acyl group Chemical group 0.000 claims description 21
- 125000004414 alkyl thio group Chemical group 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000004442 acylamino group Chemical group 0.000 claims description 18
- 125000004104 aryloxy group Chemical group 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 17
- 125000002950 monocyclic group Chemical group 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
- 230000001575 pathological effect Effects 0.000 claims description 13
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 12
- 125000003342 alkenyl group Chemical group 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 201000010099 disease Diseases 0.000 claims description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 230000005764 inhibitory process Effects 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 10
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 claims description 9
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- 239000003153 chemical reaction reagent Substances 0.000 claims description 8
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 8
- 125000001153 fluoro group Chemical group F* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 125000002947 alkylene group Chemical group 0.000 claims description 7
- 125000000304 alkynyl group Chemical group 0.000 claims description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 230000002265 prevention Effects 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 6
- 239000003814 drug Substances 0.000 claims description 6
- 239000003018 immunosuppressive agent Substances 0.000 claims description 6
- 125000001041 indolyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 6
- 235000001968 nicotinic acid Nutrition 0.000 claims description 6
- 239000011664 nicotinic acid Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 6
- 125000002971 oxazolyl group Chemical group 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- 125000003367 polycyclic group Chemical group 0.000 claims description 6
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 6
- 150000003431 steroids Chemical class 0.000 claims description 6
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- NXTGYOHUBMJCMB-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(4-fluorophenyl)-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=C(F)C=C1 NXTGYOHUBMJCMB-UHFFFAOYSA-N 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000005256 alkoxyacyl group Chemical group 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 208000006673 asthma Diseases 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- 125000002541 furyl group Chemical group 0.000 claims description 5
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 5
- PPTSELDOMGCNJJ-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(isoquinolin-4-ylamino)-6-(3-methylphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC(C)=C1 PPTSELDOMGCNJJ-UHFFFAOYSA-N 0.000 claims description 4
- YAHVARLTKYJRKA-UHFFFAOYSA-N 5-acetyl-6-(3-fluorophenyl)-2-propan-2-yl-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(C(C)C)N=C1C1=CC=CC(F)=C1 YAHVARLTKYJRKA-UHFFFAOYSA-N 0.000 claims description 4
- 239000005711 Benzoic acid Substances 0.000 claims description 4
- 108091008874 T cell receptors Proteins 0.000 claims description 4
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 claims description 4
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- PHUPHFBLIOLMOW-UHFFFAOYSA-N ethyl 4-acetyl-5-amino-1-ethyl-6-oxopyridazine-3-carboxylate Chemical compound CCOC(=O)C1=NN(CC)C(=O)C(N)=C1C(C)=O PHUPHFBLIOLMOW-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- QMBWDINOTKXJKJ-UHFFFAOYSA-N 2-ethyl-4-(isoquinolin-4-ylamino)-6-phenyl-5-(3-phenylpropanoyl)pyridazin-3-one Chemical compound C=1C=CC=CC=1CCC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 QMBWDINOTKXJKJ-UHFFFAOYSA-N 0.000 claims description 3
- POWSZOPBIYCCPE-UHFFFAOYSA-N 2-ethyl-6-phenyl-5-(3-phenylpropanoyl)-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound C=1C=CC=CC=1CCC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 POWSZOPBIYCCPE-UHFFFAOYSA-N 0.000 claims description 3
- VDELIBHTJOAOIK-UHFFFAOYSA-N 5-acetyl-2-(cyclopropylmethyl)-6-(4-fluorophenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound N1=C(C=2C=CC(F)=CC=2)C(C(=O)C)=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N1CC1CC1 VDELIBHTJOAOIK-UHFFFAOYSA-N 0.000 claims description 3
- IYOUJSCXTQAGFR-UHFFFAOYSA-N 5-acetyl-2-(cyclopropylmethyl)-6-(4-fluorophenyl)-4-(quinolin-8-ylamino)pyridazin-3-one Chemical compound N1=C(C=2C=CC(F)=CC=2)C(C(=O)C)=C(NC=2C3=NC=CC=C3C=CC=2)C(=O)N1CC1CC1 IYOUJSCXTQAGFR-UHFFFAOYSA-N 0.000 claims description 3
- QIZVFRHMVXUSKN-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(1,5-naphthyridin-3-ylamino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=C3N=CC=CC3=NC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 QIZVFRHMVXUSKN-UHFFFAOYSA-N 0.000 claims description 3
- MOCDMFXJJWUYBU-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(isoquinolin-4-ylamino)-6-(4-methylphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=C(C)C=C1 MOCDMFXJJWUYBU-UHFFFAOYSA-N 0.000 claims description 3
- YKGAJZFTIJJINO-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(3-fluorophenyl)-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC(F)=C1 YKGAJZFTIJJINO-UHFFFAOYSA-N 0.000 claims description 3
- MBXSVESBRLYZKE-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(3-fluorophenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC(F)=C1 MBXSVESBRLYZKE-UHFFFAOYSA-N 0.000 claims description 3
- FSQZUYYRLQFOLT-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(3-methoxyphenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC(OC)=C1 FSQZUYYRLQFOLT-UHFFFAOYSA-N 0.000 claims description 3
- LOBCEHUQASHXKM-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(3-methylphenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC(C)=C1 LOBCEHUQASHXKM-UHFFFAOYSA-N 0.000 claims description 3
- CGBIDNGZESMZSC-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(4-methoxyphenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=C(OC)C=C1 CGBIDNGZESMZSC-UHFFFAOYSA-N 0.000 claims description 3
- ZKOOEGYRWRWWPG-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(4-methylphenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=C(C)C=C1 ZKOOEGYRWRWWPG-UHFFFAOYSA-N 0.000 claims description 3
- ZRUKSMMAWDJANF-UHFFFAOYSA-N 5-acetyl-6-(3-chlorophenyl)-2-ethyl-4-(isoquinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=NC=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC(Cl)=C1 ZRUKSMMAWDJANF-UHFFFAOYSA-N 0.000 claims description 3
- 241001465754 Metazoa Species 0.000 claims description 3
- 150000007945 N-acyl ureas Chemical class 0.000 claims description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000010233 benzoic acid Nutrition 0.000 claims description 3
- 208000035475 disorder Diseases 0.000 claims description 3
- HJPRKFMSJWOSEH-UHFFFAOYSA-N ethyl 3-[(5-acetyl-2-ethyl-3-oxo-6-pyridin-4-ylpyridazin-4-yl)amino]benzoate Chemical compound CCOC(=O)C1=CC=CC(NC=2C(N(CC)N=C(C=2C(C)=O)C=2C=CN=CC=2)=O)=C1 HJPRKFMSJWOSEH-UHFFFAOYSA-N 0.000 claims description 3
- 229940126601 medicinal product Drugs 0.000 claims description 3
- ITIIKBZGEMBKBN-UHFFFAOYSA-N methyl 5-[(5-acetyl-2-ethyl-3-oxo-6-phenylpyridazin-4-yl)amino]quinoline-8-carboxylate Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C(C(=O)OC)=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 ITIIKBZGEMBKBN-UHFFFAOYSA-N 0.000 claims description 3
- 235000005152 nicotinamide Nutrition 0.000 claims description 3
- 239000011570 nicotinamide Substances 0.000 claims description 3
- 229960003966 nicotinamide Drugs 0.000 claims description 3
- 229960003512 nicotinic acid Drugs 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 2
- ICOVFVVBLZEFMU-UHFFFAOYSA-N 2-ethyl-6-phenyl-4-(pyridin-3-ylamino)-5-(3-thiophen-3-ylpropanoyl)pyridazin-3-one Chemical compound C1=CSC=C1CCC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 ICOVFVVBLZEFMU-UHFFFAOYSA-N 0.000 claims description 2
- DINLQJZKPAGVHP-UHFFFAOYSA-N 2-ethyl-6-phenyl-5-(3-phenylpropanoyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound C=1C=CC=CC=1CCC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 DINLQJZKPAGVHP-UHFFFAOYSA-N 0.000 claims description 2
- FMERVOMGGAZRCG-UHFFFAOYSA-N 5-acetyl-2-(cyclopropylmethyl)-6-phenyl-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound N1=C(C=2C=CC=CC=2)C(C(=O)C)=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N1CC1CC1 FMERVOMGGAZRCG-UHFFFAOYSA-N 0.000 claims description 2
- BIRSCTOECJSENB-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(1,6-naphthyridin-8-ylamino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=NC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 BIRSCTOECJSENB-UHFFFAOYSA-N 0.000 claims description 2
- SJMUMBSUGDZMEF-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(isoquinolin-4-ylamino)-6-(3-methoxyphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=CC(OC)=C1 SJMUMBSUGDZMEF-UHFFFAOYSA-N 0.000 claims description 2
- LYPGZGHLIOZNFB-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(isoquinolin-4-ylamino)-6-(4-methoxyphenyl)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=C(OC)C=C1 LYPGZGHLIOZNFB-UHFFFAOYSA-N 0.000 claims description 2
- HRSCXPMOJSWZFV-UHFFFAOYSA-N 5-acetyl-2-ethyl-6-(4-fluorophenyl)-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=C(F)C=C1 HRSCXPMOJSWZFV-UHFFFAOYSA-N 0.000 claims description 2
- ICVZTGKSZYRVKC-UHFFFAOYSA-N 5-acetyl-6-(3-chlorophenyl)-2-(cyclopropylmethyl)-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound O=C1N(CC2CC2)N=C(C=2C=C(Cl)C=CC=2)C(C(=O)C)=C1NC1=CC=CN=C1 ICVZTGKSZYRVKC-UHFFFAOYSA-N 0.000 claims description 2
- ZGLJIVIDIOHDHI-UHFFFAOYSA-N 5-acetyl-6-(3-chlorophenyl)-2-ethyl-4-(pyridin-3-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=NC=CC=2)C(=O)N(CC)N=C1C1=CC=CC(Cl)=C1 ZGLJIVIDIOHDHI-UHFFFAOYSA-N 0.000 claims description 2
- BHOLIRBLRKVVBI-UHFFFAOYSA-N 5-acetyl-6-(3-chlorophenyl)-2-ethyl-4-(quinolin-5-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CN=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC(Cl)=C1 BHOLIRBLRKVVBI-UHFFFAOYSA-N 0.000 claims description 2
- NSEYIBHLTVGNTO-UHFFFAOYSA-N 5-acetyl-6-(3-chlorophenyl)-2-ethyl-4-(quinolin-8-ylamino)pyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=NC=CC=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC(Cl)=C1 NSEYIBHLTVGNTO-UHFFFAOYSA-N 0.000 claims description 2
- MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 229940125721 immunosuppressive agent Drugs 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
- 239000011593 sulfur Chemical group 0.000 claims description 2
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- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- XFTQRUTUGRCSGO-UHFFFAOYSA-N pyrazin-2-amine Chemical compound NC1=CN=CC=N1 XFTQRUTUGRCSGO-UHFFFAOYSA-N 0.000 description 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 description 1
- 125000002755 pyrazolinyl group Chemical group 0.000 description 1
- JUSIWJONLKBPDU-UHFFFAOYSA-N pyridazine-4-carboxylic acid Chemical compound OC(=O)C1=CC=NN=C1 JUSIWJONLKBPDU-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
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- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000004071 soot Substances 0.000 description 1
- 235000013555 soy sauce Nutrition 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
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- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- IRGDRSIZYKSOPT-UHFFFAOYSA-N thiophen-2-ylazanium;chloride Chemical compound Cl.NC1=CC=CS1 IRGDRSIZYKSOPT-UHFFFAOYSA-N 0.000 description 1
- VNMLVHLVBFHHSN-UHFFFAOYSA-N thiophen-2-ylcarbamic acid Chemical compound OC(=O)NC1=CC=CS1 VNMLVHLVBFHHSN-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- IZSFYANROMTISV-UHFFFAOYSA-N trifluoro-(sulfamoylamino)methane Chemical compound NS(=O)(=O)NC(F)(F)F IZSFYANROMTISV-UHFFFAOYSA-N 0.000 description 1
- 229920000685 trimethylsilyl polyphosphate Polymers 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1
- 229960001763 zinc sulfate Drugs 0.000 description 1
- 229910000368 zinc sulfate Inorganic materials 0.000 description 1
Classifications
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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ES200203003A ES2211344B1 (es) | 2002-12-26 | 2002-12-26 | Nuevos derivados de piridazin-3(2h)-ona. |
PCT/EP2003/014722 WO2004058729A1 (en) | 2002-12-26 | 2003-12-22 | New pyridazin-3(2h)-one derivatives |
Publications (1)
Publication Number | Publication Date |
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UA80016C2 true UA80016C2 (en) | 2007-08-10 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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UAA200507288A UA80016C2 (en) | 2002-12-26 | 2003-12-22 | Pyridazin-3(2h)-one derivates |
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US (2) | US7491722B2 (es) |
EP (1) | EP1575926B1 (es) |
JP (1) | JP4679154B2 (es) |
KR (1) | KR20050087868A (es) |
CN (1) | CN100443474C (es) |
AR (1) | AR042665A1 (es) |
AT (1) | ATE388140T1 (es) |
AU (1) | AU2003290110B2 (es) |
BR (1) | BR0316883A (es) |
CA (1) | CA2512099A1 (es) |
CL (1) | CL2003002746A1 (es) |
CY (1) | CY1107978T1 (es) |
DE (1) | DE60319584T2 (es) |
DK (1) | DK1575926T3 (es) |
EC (1) | ECSP055883A (es) |
ES (2) | ES2211344B1 (es) |
HK (1) | HK1075629A1 (es) |
MX (1) | MXPA05006809A (es) |
MY (1) | MY140725A (es) |
NO (1) | NO20053614L (es) |
NZ (1) | NZ540762A (es) |
PE (1) | PE20040937A1 (es) |
PT (1) | PT1575926E (es) |
RU (1) | RU2346939C2 (es) |
SI (1) | SI1575926T1 (es) |
TW (1) | TWI287545B (es) |
UA (1) | UA80016C2 (es) |
UY (1) | UY28141A1 (es) |
WO (1) | WO2004058729A1 (es) |
ZA (1) | ZA200504943B (es) |
Families Citing this family (71)
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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. |
ES2232306B1 (es) * | 2003-11-10 | 2006-08-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
DE602005022499D1 (de) | 2004-05-31 | 2010-09-02 | 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. |
CA2584261A1 (en) * | 2004-10-13 | 2006-04-20 | Kyowa Hakko Kogyo Co., Ltd. | Pharmaceutical composition |
EP1810692A1 (en) * | 2004-10-13 | 2007-07-25 | Kyowa Hakko Kogyo Co., Ltd. | Remedies/preventives for chronic skin disease |
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. |
ES2354627T3 (es) | 2005-10-05 | 2011-03-16 | F. Hoffmann-La Roche Ag | Derivados de naftiridina. |
JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
KR20080094921A (ko) * | 2006-01-16 | 2008-10-27 | 우베 고산 가부시키가이샤 | 피롤로피리다지논 화합물 |
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. |
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. |
PT2148873E (pt) | 2007-04-23 | 2012-11-20 | Janssen Pharmaceutica Nv | Derivados da 4-alcoxipiridazina antagonistas de dissociação rápida do recetor da dopamina 2 |
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