OA11582A - Phthalazine derivatives phosphodiesterase 4 inhibitors. - Google Patents
Phthalazine derivatives phosphodiesterase 4 inhibitors. Download PDFInfo
- Publication number
- OA11582A OA11582A OA1200100019A OA1200100019A OA11582A OA 11582 A OA11582 A OA 11582A OA 1200100019 A OA1200100019 A OA 1200100019A OA 1200100019 A OA1200100019 A OA 1200100019A OA 11582 A OA11582 A OA 11582A
- Authority
- OA
- OAPI
- Prior art keywords
- mmoles
- methoxy
- dichloro
- pyridin
- give
- Prior art date
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- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 title abstract description 8
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 257
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 31
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 21
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- -1 nitro, carboxy groups Chemical group 0.000 claims abstract description 16
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 9
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 4
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 4
- 125000003277 amino group Chemical group 0.000 claims abstract description 4
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 4
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 29
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 238000011282 treatment Methods 0.000 claims description 8
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
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- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
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- 125000006705 (C5-C7) cycloalkyl group Chemical group 0.000 abstract description 7
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract description 5
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract description 5
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract description 5
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- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- YNHIGQDRGKUECZ-UHFFFAOYSA-N dichloropalladium;triphenylphosphanium Chemical compound Cl[Pd]Cl.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1[PH+](C=1C=CC=CC=1)C1=CC=CC=C1 YNHIGQDRGKUECZ-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 1
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- SRZXTJYVDZUQAN-UHFFFAOYSA-N ethyl 3-(4-chloro-6-methoxyphthalazin-1-yl)propanoate Chemical compound COC1=CC=C2C(CCC(=O)OCC)=NN=C(Cl)C2=C1 SRZXTJYVDZUQAN-UHFFFAOYSA-N 0.000 description 1
- YNRPEKBXBBOJJE-UHFFFAOYSA-N ethyl 3-(6-methoxy-4-oxo-3h-phthalazin-1-yl)propanoate Chemical compound COC1=CC=C2C(CCC(=O)OCC)=NNC(=O)C2=C1 YNRPEKBXBBOJJE-UHFFFAOYSA-N 0.000 description 1
- LMMKIGZSMNAXDB-UHFFFAOYSA-N ethyl 3-[6-methoxy-4-(1,3-thiazol-2-yl)phthalazin-1-yl]propanoate Chemical compound C12=CC(OC)=CC=C2C(CCC(=O)OCC)=NN=C1C1=NC=CS1 LMMKIGZSMNAXDB-UHFFFAOYSA-N 0.000 description 1
- GWNFQAKCJYEJEW-UHFFFAOYSA-N ethyl 3-[8-[[4-methyl-5-[(3-methyl-4-oxophthalazin-1-yl)methyl]-1,2,4-triazol-3-yl]sulfanyl]octanoylamino]benzoate Chemical compound CCOC(=O)C1=CC(NC(=O)CCCCCCCSC2=NN=C(CC3=NN(C)C(=O)C4=CC=CC=C34)N2C)=CC=C1 GWNFQAKCJYEJEW-UHFFFAOYSA-N 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
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- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
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- 229910052731 fluorine Inorganic materials 0.000 description 1
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- 150000004795 grignard reagents Chemical class 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WQPDUTSPKFMPDP-OUMQNGNKSA-N hirudin Chemical compound C([C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC(OS(O)(=O)=O)=CC=1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(N)=O)C(O)=O)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H]1NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CO)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H](C(=O)N[C@H](C(NCC(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCCCN)C(=O)N2)=O)CSSC1)C(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)CNC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=2C=CC(O)=CC=2)NC(=O)[C@@H](NC(=O)[C@@H](N)C(C)C)C(C)C)[C@@H](C)O)CSSC1)C(C)C)[C@@H](C)O)[C@@H](C)O)C1=CC=CC=C1 WQPDUTSPKFMPDP-OUMQNGNKSA-N 0.000 description 1
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- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- SQTJICYBJPHFNH-UHFFFAOYSA-N methyl 4-(6-methoxy-4-oxo-3h-phthalazin-1-yl)butanoate Chemical compound COC1=CC=C2C(CCCC(=O)OC)=NNC(=O)C2=C1 SQTJICYBJPHFNH-UHFFFAOYSA-N 0.000 description 1
- USMUKQLLFFOKQJ-UHFFFAOYSA-N methyl 4-[6-methoxy-4-(1,3-thiazol-2-yl)phthalazin-1-yl]butanoate Chemical compound C12=CC(OC)=CC=C2C(CCCC(=O)OC)=NN=C1C1=NC=CS1 USMUKQLLFFOKQJ-UHFFFAOYSA-N 0.000 description 1
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- YGBMCLDVRUGXOV-UHFFFAOYSA-N n-[6-[6-chloro-5-[(4-fluorophenyl)sulfonylamino]pyridin-3-yl]-1,3-benzothiazol-2-yl]acetamide Chemical compound C1=C2SC(NC(=O)C)=NC2=CC=C1C(C=1)=CN=C(Cl)C=1NS(=O)(=O)C1=CC=C(F)C=C1 YGBMCLDVRUGXOV-UHFFFAOYSA-N 0.000 description 1
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- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
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- 125000002347 octyl 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])[H] 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
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- 210000002741 palatine tonsil Anatomy 0.000 description 1
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- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 1
- UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
- IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
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- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- IEVXRRZWEHUEHP-UHFFFAOYSA-M potassium;3-ethoxy-3-oxoprop-1-en-1-olate Chemical compound [K+].CCOC(=O)C=C[O-] IEVXRRZWEHUEHP-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- ZVJHJDDKYZXRJI-UHFFFAOYSA-N pyrroline Natural products C1CC=NC1 ZVJHJDDKYZXRJI-UHFFFAOYSA-N 0.000 description 1
- 239000000700 radioactive tracer Substances 0.000 description 1
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- 230000004044 response Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 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
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical compound O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 229940056345 tums Drugs 0.000 description 1
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Classifications
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
- C07D207/09—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/42—Radicals substituted by singly-bound nitrogen atoms having hetero atoms attached to the substituent nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/32—Phthalazines with oxygen atoms directly attached to carbon atoms of the nitrogen-containing ring
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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
- C07D237/26—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings condensed with carbocyclic rings or ring systems
- C07D237/30—Phthalazines
- C07D237/34—Phthalazines with nitrogen atoms directly attached to carbon atoms of the nitrogen-containing ring, e.g. hydrazine radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/28—Radicals substituted by nitrogen atoms
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- C—CHEMISTRY; METALLURGY
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- 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
- C07D401/14—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 three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- 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
-
- 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
- C07D417/14—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 three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT98MI001670A ITMI981670A1 (it) | 1998-07-21 | 1998-07-21 | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| OA11582A true OA11582A (en) | 2004-07-26 |
Family
ID=11380474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| OA1200100019A OA11582A (en) | 1998-07-21 | 1999-07-13 | Phthalazine derivatives phosphodiesterase 4 inhibitors. |
Country Status (35)
| Country | Link |
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| US (2) | US6329370B1 (is) |
| EP (2) | EP1097142B1 (is) |
| JP (1) | JP2002521370A (is) |
| KR (1) | KR20010087161A (is) |
| CN (1) | CN1127486C (is) |
| AP (1) | AP2000001993A0 (is) |
| AR (1) | AR019409A1 (is) |
| AT (1) | ATE279397T1 (is) |
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| BR (1) | BR9911175A (is) |
| CA (1) | CA2338044A1 (is) |
| CO (1) | CO5090842A1 (is) |
| DE (1) | DE69921139T2 (is) |
| EA (1) | EA200100062A1 (is) |
| EE (1) | EE200100039A (is) |
| HK (1) | HK1039124B (is) |
| HR (1) | HRP20010057A2 (is) |
| HU (1) | HUP0102646A3 (is) |
| ID (1) | ID28874A (is) |
| IL (1) | IL139490A0 (is) |
| IS (1) | IS5772A (is) |
| IT (1) | ITMI981670A1 (is) |
| MX (1) | MXPA01000670A (is) |
| NO (1) | NO318988B1 (is) |
| NZ (1) | NZ507926A (is) |
| OA (1) | OA11582A (is) |
| PA (1) | PA8478301A1 (is) |
| PE (1) | PE20000755A1 (is) |
| PL (1) | PL345187A1 (is) |
| SK (1) | SK1002001A3 (is) |
| TW (1) | TW509682B (is) |
| UA (1) | UA68383C2 (is) |
| WO (1) | WO2000005218A1 (is) |
| YU (1) | YU77500A (is) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CO4950519A1 (es) * | 1997-02-13 | 2000-09-01 | Novartis Ag | Ftalazinas, preparaciones farmaceuticas que las comprenden y proceso para su preparacion |
| IT1296984B1 (it) * | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
| ITMI981671A1 (it) | 1998-07-21 | 2000-01-21 | Zambon Spa | Derivati ftalazinici inibitori della fosfodisterasi 4 |
| DE19921567A1 (de) | 1999-05-11 | 2000-11-16 | Basf Ag | Verwendung von Phthalazine-Derivaten |
| DE19963607B4 (de) * | 1999-12-23 | 2005-12-15 | Schering Ag | Verfahren zur Herstellung von 4-(Heteroaryl-methyl) halogen-1(2H)-phthalazinonen |
| ITMI20000261A1 (it) * | 2000-02-16 | 2001-08-16 | Zambon Group | Processo per la preparazione di piridiniliden-ftalidi |
| US6703390B2 (en) * | 2000-04-13 | 2004-03-09 | Transgenomic, Inc. | Sulfur containing dihydrophthalazine antagonists of excitatory amino acid receptors |
| US6525049B2 (en) * | 2000-07-05 | 2003-02-25 | Pharmacia & Upjohn Company | Pyrroloquinolones as antiviral agents |
| WO2002044157A2 (en) * | 2000-12-01 | 2002-06-06 | Iconix Pharmaceuticals, Inc. | Parb inhibitors |
| ITMI20022738A1 (it) * | 2002-12-23 | 2004-06-24 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4. |
| ITMI20022739A1 (it) * | 2002-12-23 | 2004-06-24 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4. |
| WO2004076386A2 (en) | 2003-02-25 | 2004-09-10 | Topotarget Uk Limited | Carbamic acid compounds comprising a bicyclic heteroaryl group as hdac inhibitors |
| ITMI20031451A1 (it) * | 2003-07-16 | 2005-01-17 | Zambon Spa | Derivati diidro-ftalazinici inibitori della fosfodiesterasi 4 |
| US8338591B2 (en) * | 2004-05-08 | 2012-12-25 | Novartis International Pharmaceutical Ltd. | 3-aryl-5,6-disubstituted pyridazines |
| CA2593005A1 (en) * | 2005-01-03 | 2006-07-13 | Myriad Genetics Inc. | Pharmaceutical compounds as activators of caspases and inducers of apoptosis and the use thereof |
| RU2008119323A (ru) | 2005-10-19 | 2009-11-27 | Рэнбакси Лабораториз Лимитед (In) | Фармацевтические композиции мускаринового рецептора |
| EP2131656A4 (en) | 2006-11-15 | 2011-12-07 | Forest Lab Holdings Ltd | phthalazine |
| EP2323991B1 (en) * | 2008-08-13 | 2017-05-31 | Boehringer Ingelheim International GmbH | Chymase inhibitors |
| CN102108078B (zh) * | 2009-12-24 | 2013-10-30 | 沈阳药科大学 | 1,4-取代酞嗪类化合物及其制备方法和用途 |
| SG11201402134VA (en) * | 2011-11-09 | 2014-06-27 | Abbvie Deutschland | Heterocyclic carboxamides useful as inhibitors of phosphodiesterase type 10a |
| CN117924243B (zh) * | 2024-01-16 | 2025-09-12 | 沈阳药科大学 | 一种喹啉衍生物及其药用组合物和应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2063249A (en) * | 1979-10-09 | 1981-06-03 | Mitsubishi Yuka Pharma | 4-Phenylphthalazine derivatives |
| JPH03106873A (ja) * | 1989-09-20 | 1991-05-07 | Morishita Pharmaceut Co Ltd | 1―ピリジルフタラジン誘導体及びそれらを含有する血小板凝集抑制剤 |
| DE69105572T2 (de) * | 1990-03-30 | 1995-05-11 | Mitsubishi Chem Ind | 4-Phenylphthalazin-Derivate. |
| EP0634404A1 (en) * | 1993-07-13 | 1995-01-18 | Rhone Poulenc Agriculture Ltd. | Phtalazin derivatives and their use as pesticides |
| CA2173493C (en) * | 1994-08-09 | 2008-03-25 | Nobuhisa Watanabe | Fused pyridazine compounds |
| IT1296984B1 (it) | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
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1998
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1999
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- 1999-07-13 BR BR9911175-6A patent/BR9911175A/pt not_active IP Right Cessation
- 1999-07-13 CA CA002338044A patent/CA2338044A1/en not_active Abandoned
- 1999-07-13 NZ NZ507926A patent/NZ507926A/xx unknown
- 1999-07-13 EA EA200100062A patent/EA200100062A1/ru unknown
- 1999-07-13 YU YU77500A patent/YU77500A/sh unknown
- 1999-07-13 KR KR1020017000971A patent/KR20010087161A/ko not_active Ceased
- 1999-07-13 DE DE69921139T patent/DE69921139T2/de not_active Expired - Fee Related
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- 1999-07-13 JP JP2000561174A patent/JP2002521370A/ja active Pending
- 1999-07-13 WO PCT/EP1999/004904 patent/WO2000005218A1/en not_active Ceased
- 1999-07-13 EP EP99938229A patent/EP1097142B1/en not_active Expired - Lifetime
- 1999-07-13 CN CN99807294A patent/CN1127486C/zh not_active Expired - Fee Related
- 1999-07-13 AP APAP/P/2000/001993A patent/AP2000001993A0/en unknown
- 1999-07-13 EP EP03102377A patent/EP1371648A1/en not_active Withdrawn
- 1999-07-13 ID IDW20010132A patent/ID28874A/id unknown
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- 1999-07-13 HK HK02100584.0A patent/HK1039124B/zh not_active IP Right Cessation
- 1999-07-13 HR HR20010057A patent/HRP20010057A2/hr not_active Application Discontinuation
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- 1999-07-13 OA OA1200100019A patent/OA11582A/en unknown
- 1999-07-13 UA UA2001010439A patent/UA68383C2/uk unknown
- 1999-07-13 IL IL13949099A patent/IL139490A0/xx not_active IP Right Cessation
- 1999-07-13 AU AU52810/99A patent/AU765457B2/en not_active Ceased
- 1999-07-13 US US09/743,813 patent/US6329370B1/en not_active Expired - Fee Related
- 1999-07-13 MX MXPA01000670A patent/MXPA01000670A/es not_active Application Discontinuation
- 1999-07-13 AT AT99938229T patent/ATE279397T1/de not_active IP Right Cessation
- 1999-07-16 AR ARP990103501A patent/AR019409A1/es unknown
- 1999-07-19 TW TW088112218A patent/TW509682B/zh not_active IP Right Cessation
- 1999-07-19 CO CO99045518A patent/CO5090842A1/es unknown
- 1999-07-19 PA PA19998478301A patent/PA8478301A1/es unknown
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2000
- 2000-12-15 IS IS5772A patent/IS5772A/is unknown
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2001
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- 2001-10-15 US US09/976,436 patent/US6492360B1/en not_active Expired - Fee Related
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