ZA200504943B - New pyridazin-3(2H)-one derivatives - Google Patents
New pyridazin-3(2H)-one derivatives Download PDFInfo
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- ZA200504943B ZA200504943B ZA200504943A ZA200504943A ZA200504943B ZA 200504943 B ZA200504943 B ZA 200504943B ZA 200504943 A ZA200504943 A ZA 200504943A ZA 200504943 A ZA200504943 A ZA 200504943A ZA 200504943 B ZA200504943 B ZA 200504943B
- Authority
- ZA
- South Africa
- Prior art keywords
- acetyl
- ethyl
- amino
- pyridin
- pyridazin
- 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 claims description 76
- -1 atkoxycarbonyl Chemical group 0.000 claims description 423
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 216
- 125000001424 substituent group Chemical group 0.000 claims description 147
- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 125000003545 alkoxy group Chemical group 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 125000005843 halogen group Chemical group 0.000 claims description 74
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 62
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 45
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 43
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 29
- 125000001153 fluoro group Chemical group F* 0.000 claims description 27
- 229910052799 carbon Inorganic materials 0.000 claims description 26
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 25
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 24
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 125000004414 alkyl thio group Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
- 125000004442 acylamino group Chemical group 0.000 claims description 21
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical group O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 21
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
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- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 13
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000005530 alkylenedioxy group Chemical group 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000004043 oxo group Chemical group O=* 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 229910052717 sulfur Inorganic materials 0.000 claims description 9
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 7
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- 229910052731 fluorine Inorganic materials 0.000 claims description 7
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- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002883 imidazolyl group Chemical group 0.000 claims description 7
- 230000005764 inhibitory process Effects 0.000 claims description 7
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 6
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- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
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- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 6
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- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
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- 125000002971 oxazolyl group Chemical group 0.000 claims description 5
- 230000001575 pathological effect Effects 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
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- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 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
- UQULUALMFFYJLC-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(naphthalen-1-ylamino)-6-pyridin-4-ylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=NC=C1 UQULUALMFFYJLC-UHFFFAOYSA-N 0.000 claims description 3
- 150000001204 N-oxides Chemical class 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-M benzoate Chemical compound [O-]C(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-M 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 239000012024 dehydrating agents Substances 0.000 claims description 3
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- QRDZFPUVLYEQTA-UHFFFAOYSA-N quinoline-8-carboxylic acid Chemical compound C1=CN=C2C(C(=O)O)=CC=CC2=C1 QRDZFPUVLYEQTA-UHFFFAOYSA-N 0.000 claims description 3
- 150000003431 steroids Chemical class 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 2
- JAKGRYDCCXIQID-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(1,2-oxazol-3-ylamino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC2=NOC=C2)C(=O)N(CC)N=C1C1=CC=CC=C1 JAKGRYDCCXIQID-UHFFFAOYSA-N 0.000 claims description 2
- UKKJYRUUBQFMKA-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(1h-indazol-7-ylamino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C=3NN=CC=3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 UKKJYRUUBQFMKA-UHFFFAOYSA-N 0.000 claims description 2
- DCKXRWBKWWZSMV-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(isoquinolin-1-ylamino)-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=CN=2)C(=O)N(CC)N=C1C1=CC=CC=C1 DCKXRWBKWWZSMV-UHFFFAOYSA-N 0.000 claims description 2
- XBJPBCDERIOLDC-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-(isoquinolin-4-ylamino)-6-pyridin-4-ylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=CC=CC=C3C=NC=2)C(=O)N(CC)N=C1C1=CC=NC=C1 XBJPBCDERIOLDC-UHFFFAOYSA-N 0.000 claims description 2
- RQOHQARLTZNGGF-UHFFFAOYSA-N 5-acetyl-2-ethyl-4-[(2-methylquinolin-8-yl)amino]-6-phenylpyridazin-3-one Chemical compound CC(=O)C1=C(NC=2C3=NC(C)=CC=C3C=CC=2)C(=O)N(CC)N=C1C1=CC=CC=C1 RQOHQARLTZNGGF-UHFFFAOYSA-N 0.000 claims description 2
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- 239000000126 substance Substances 0.000 description 1
- 125000005156 substituted alkylene group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 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
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 230000017423 tissue regeneration Effects 0.000 description 1
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 1
- JLTRXTDYQLMHGR-UHFFFAOYSA-N trimethylaluminium Chemical compound C[Al](C)C JLTRXTDYQLMHGR-UHFFFAOYSA-N 0.000 description 1
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- 230000001562 ulcerogenic effect Effects 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
- 230000035899 viability Effects 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
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Classifications
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- 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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- 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
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- 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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- 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
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- 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
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- 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
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- 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
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- 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 (1)
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ES200203003A ES2211344B1 (es) | 2002-12-26 | 2002-12-26 | Nuevos derivados de piridazin-3(2h)-ona. |
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ZA200504943A ZA200504943B (en) | 2002-12-26 | 2003-12-22 | New pyridazin-3(2H)-one derivatives |
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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) |
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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) |
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TW (1) | TWI287545B (es) |
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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 |
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JO2769B1 (en) | 2005-10-26 | 2014-03-15 | جانسين فارماسوتيكا ان. في | Rapid decomposition of physiologically antagonistic agents of the 2-dopamine receptor |
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- 2003-12-22 KR KR1020057012084A patent/KR20050087868A/ko not_active Application Discontinuation
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