UA68383C2 - Phthalazine derivatives and pharmaceutical compositions - Google Patents
Phthalazine derivatives and pharmaceutical compositions Download PDFInfo
- Publication number
- UA68383C2 UA68383C2 UA2001010439A UA2001010439A UA68383C2 UA 68383 C2 UA68383 C2 UA 68383C2 UA 2001010439 A UA2001010439 A UA 2001010439A UA 2001010439 A UA2001010439 A UA 2001010439A UA 68383 C2 UA68383 C2 UA 68383C2
- Authority
- UA
- Ukraine
- Prior art keywords
- methoxy
- mmol
- compound
- methyl
- dichloropyridin
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 title description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 281
- -1 nitro, carboxy groups Chemical group 0.000 claims abstract description 47
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 34
- 239000001257 hydrogen Substances 0.000 claims abstract description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 34
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 16
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 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
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 5
- 125000003368 amide group Chemical group 0.000 claims abstract description 5
- 125000001769 aryl amino group Chemical group 0.000 claims abstract description 5
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 5
- 125000004043 oxo group Chemical group O=* 0.000 claims abstract description 5
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 4
- 125000005844 heterocyclyloxy group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- 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 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 8
- 125000000304 alkynyl group Chemical group 0.000 claims description 8
- 230000000172 allergic effect Effects 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 208000027866 inflammatory disease Diseases 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- HMTGPYRFOCPERJ-UHFFFAOYSA-N 1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxy-4-phenylphthalazine Chemical compound N=1N=C(C=2C=CC=CC=2)C2=CC(OC)=CC=C2C=1CC1=C(Cl)C=NC=C1Cl HMTGPYRFOCPERJ-UHFFFAOYSA-N 0.000 claims description 2
- RQKYYWBMXHYBAP-UHFFFAOYSA-N 4-(chloromethyl)-2,2-dimethyl-1,3,2-dioxasilolane Chemical group C[Si]1(C)OCC(CCl)O1 RQKYYWBMXHYBAP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 208000026935 allergic disease Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- NBNCEZNBWYPDFB-UHFFFAOYSA-N 4-[4-[(3,5-dichloropyridin-4-yl)methyl]-7-methoxyphthalazin-1-yl]morpholine Chemical compound N=1N=C(N2CCOCC2)C2=CC(OC)=CC=C2C=1CC1=C(Cl)C=NC=C1Cl NBNCEZNBWYPDFB-UHFFFAOYSA-N 0.000 claims 1
- 101100314454 Caenorhabditis elegans tra-1 gene Proteins 0.000 claims 1
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims 1
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 238000012876 topography Methods 0.000 claims 1
- 125000003277 amino group Chemical group 0.000 abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 2
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 abstract 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 abstract 1
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 abstract 1
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 abstract 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 243
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 180
- 239000000203 mixture Substances 0.000 description 175
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 141
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 138
- 239000000243 solution Substances 0.000 description 112
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 84
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
- 239000007787 solid Substances 0.000 description 73
- 238000002844 melting Methods 0.000 description 70
- 230000008018 melting Effects 0.000 description 70
- 239000012074 organic phase Substances 0.000 description 66
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 65
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- 239000003480 eluent Substances 0.000 description 50
- 238000010992 reflux Methods 0.000 description 48
- 238000004809 thin layer chromatography Methods 0.000 description 47
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 44
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 42
- 239000000725 suspension Substances 0.000 description 41
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- 229940066842 petrolatum Drugs 0.000 description 25
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 24
- 229960000583 acetic acid Drugs 0.000 description 23
- 238000000034 method Methods 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 229910052700 potassium Inorganic materials 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000003610 charcoal Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
- 239000000126 substance Substances 0.000 description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000002156 mixing Methods 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- INJOULQGSUBQJR-UHFFFAOYSA-N 4-[(3,5-dichloropyridin-4-yl)methyl]-7-methoxy-1,2-dihydrophthalazine Chemical compound N=1NCC2=CC(OC)=CC=C2C=1CC1=C(Cl)C=NC=C1Cl INJOULQGSUBQJR-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- 102000004190 Enzymes Human genes 0.000 description 12
- 108090000790 Enzymes Proteins 0.000 description 12
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 12
- 150000002431 hydrogen Chemical class 0.000 description 12
- 210000004027 cell Anatomy 0.000 description 11
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 11
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 11
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
- 239000008346 aqueous phase Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 10
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 9
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 9
- 210000001616 monocyte Anatomy 0.000 description 9
- 239000012071 phase Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- FZNLULCNCVCWKJ-UHFFFAOYSA-N 1-[(3,5-dichloropyridin-4-yl)methyl]-4-ethyl-6-methoxyphthalazine Chemical compound C12=CC=C(OC)C=C2C(CC)=NN=C1CC1=C(Cl)C=NC=C1Cl FZNLULCNCVCWKJ-UHFFFAOYSA-N 0.000 description 8
- YBHYECGRNFZJPC-UHFFFAOYSA-N 3,5-dichloro-4-methylpyridine Chemical compound CC1=C(Cl)C=NC=C1Cl YBHYECGRNFZJPC-UHFFFAOYSA-N 0.000 description 8
- 101100237844 Mus musculus Mmp19 gene Proteins 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- 238000000354 decomposition reaction Methods 0.000 description 8
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- RPQKQQJAHJDVOD-UHFFFAOYSA-N 4-chloro-1-[(3,5-dichloropyridin-4-yl)methyl]-6-methoxyphthalazine Chemical compound N=1N=C(Cl)C2=CC(OC)=CC=C2C=1CC1=C(Cl)C=NC=C1Cl RPQKQQJAHJDVOD-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- ZYKKSNKZEXNOLS-UHFFFAOYSA-N 4-[(3,5-dichloropyridin-4-yl)methyl]-7-methoxy-2h-phthalazin-1-one Chemical compound N=1NC(=O)C2=CC(OC)=CC=C2C=1CC1=C(Cl)C=NC=C1Cl ZYKKSNKZEXNOLS-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 6
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- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 6
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- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 6
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- HGSCIJVKEUKATE-UHFFFAOYSA-M (5-methoxy-3-oxo-1h-2-benzofuran-1-yl)-triphenylphosphanium;bromide Chemical compound [Br-].O1C(=O)C2=CC(OC)=CC=C2C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 HGSCIJVKEUKATE-UHFFFAOYSA-M 0.000 description 5
- HQVCWVGSZXODRW-UHFFFAOYSA-N 2-(4-methoxyphenyl)-4,4-dimethyl-5h-1,3-oxazole Chemical compound C1=CC(OC)=CC=C1C1=NC(C)(C)CO1 HQVCWVGSZXODRW-UHFFFAOYSA-N 0.000 description 5
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- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
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
-
- 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
-
- 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
- C07D401/14—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
-
- 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
Landscapes
- 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)
- Pyridine Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT98MI001670A ITMI981670A1 (it) | 1998-07-21 | 1998-07-21 | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
PCT/EP1999/004904 WO2000005218A1 (en) | 1998-07-21 | 1999-07-13 | Phthalazine derivatives phosphodiesterase 4 inhibitors |
Publications (1)
Publication Number | Publication Date |
---|---|
UA68383C2 true UA68383C2 (en) | 2004-08-16 |
Family
ID=11380474
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA2001010439A UA68383C2 (en) | 1998-07-21 | 1999-07-13 | Phthalazine derivatives and pharmaceutical compositions |
Country Status (35)
Country | Link |
---|---|
US (2) | US6329370B1 (xx) |
EP (2) | EP1097142B1 (xx) |
JP (1) | JP2002521370A (xx) |
KR (1) | KR20010087161A (xx) |
CN (1) | CN1127486C (xx) |
AP (1) | AP2000001993A0 (xx) |
AR (1) | AR019409A1 (xx) |
AT (1) | ATE279397T1 (xx) |
AU (1) | AU765457B2 (xx) |
BG (1) | BG105063A (xx) |
BR (1) | BR9911175A (xx) |
CA (1) | CA2338044A1 (xx) |
CO (1) | CO5090842A1 (xx) |
DE (1) | DE69921139T2 (xx) |
EA (1) | EA200100062A1 (xx) |
EE (1) | EE200100039A (xx) |
HK (1) | HK1039124B (xx) |
HR (1) | HRP20010057A2 (xx) |
HU (1) | HUP0102646A3 (xx) |
ID (1) | ID28874A (xx) |
IL (1) | IL139490A0 (xx) |
IS (1) | IS5772A (xx) |
IT (1) | ITMI981670A1 (xx) |
MX (1) | MXPA01000670A (xx) |
NO (1) | NO318988B1 (xx) |
NZ (1) | NZ507926A (xx) |
OA (1) | OA11582A (xx) |
PA (1) | PA8478301A1 (xx) |
PE (1) | PE20000755A1 (xx) |
PL (1) | PL345187A1 (xx) |
SK (1) | SK1002001A3 (xx) |
TW (1) | TW509682B (xx) |
UA (1) | UA68383C2 (xx) |
WO (1) | WO2000005218A1 (xx) |
YU (1) | YU77500A (xx) |
Families Citing this family (20)
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 |
AU2002220241A1 (en) * | 2000-12-01 | 2002-06-11 | 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 |
WO2006004589A2 (en) * | 2004-05-08 | 2006-01-12 | Neurogen Corporation | 3-aryl-5,6-disubstituted pyridazines |
EP1833803A4 (en) * | 2005-01-03 | 2009-08-05 | Myriad Genetics Inc | PHARMACEUTICAL COMPOUNDS COMPRISING CASPASE ACTIVATORS AND INDUCERS OF APOPTOSIS AND THE USE THEREOF |
AU2006305619A1 (en) | 2005-10-19 | 2007-04-26 | Ranbaxy Laboratories Limited | Pharmaceutical compositions of muscarinic receptor antagonists |
CA2669687C (en) | 2006-11-15 | 2013-09-10 | Forest Laboratories Holdings Limited | Phthalazine derivatives |
US8969348B2 (en) * | 2008-08-13 | 2015-03-03 | 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 |
RU2014123352A (ru) * | 2011-11-09 | 2015-12-20 | Эббви Дойчланд Гмбх Унд Ко. Кг | Гетероциклические карбоксамиды, полезные в качестве ингибиторов фосфодиэстеразы типа 10а |
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 |
ES2068413T3 (es) * | 1990-03-30 | 1995-04-16 | Mitsubishi Chem Ind | Derivados de 4-fenilftalazina. |
EP0634404A1 (en) * | 1993-07-13 | 1995-01-18 | Rhone Poulenc Agriculture Ltd. | Phtalazin derivatives and their use as pesticides |
EP0722936B1 (en) * | 1994-08-09 | 2004-05-19 | Eisai Co., Ltd. | Fused pyridazine compound |
IT1296984B1 (it) * | 1997-12-19 | 1999-08-03 | Zambon Spa | Derivati ftalazinici inibitori della fosfodiesterasi 4 |
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1998
- 1998-07-21 IT IT98MI001670A patent/ITMI981670A1/it unknown
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1999
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- 1999-07-13 US US09/743,813 patent/US6329370B1/en not_active Expired - Fee Related
- 1999-07-13 JP JP2000561174A patent/JP2002521370A/ja active Pending
- 1999-07-13 OA OA1200100019A patent/OA11582A/en unknown
- 1999-07-13 KR KR1020017000971A patent/KR20010087161A/ko not_active Application Discontinuation
- 1999-07-13 DE DE69921139T patent/DE69921139T2/de not_active Expired - Fee Related
- 1999-07-13 MX MXPA01000670A patent/MXPA01000670A/es not_active Application Discontinuation
- 1999-07-13 YU YU77500A patent/YU77500A/sh unknown
- 1999-07-13 SK SK100-2001A patent/SK1002001A3/sk unknown
- 1999-07-13 AP APAP/P/2000/001993A patent/AP2000001993A0/en unknown
- 1999-07-13 CA CA002338044A patent/CA2338044A1/en not_active Abandoned
- 1999-07-13 WO PCT/EP1999/004904 patent/WO2000005218A1/en not_active Application Discontinuation
- 1999-07-13 EP EP99938229A patent/EP1097142B1/en not_active Expired - Lifetime
- 1999-07-13 AU AU52810/99A patent/AU765457B2/en not_active Ceased
- 1999-07-13 AT AT99938229T patent/ATE279397T1/de not_active IP Right Cessation
- 1999-07-13 IL IL13949099A patent/IL139490A0/xx not_active IP Right Cessation
- 1999-07-13 PL PL99345187A patent/PL345187A1/xx not_active Application Discontinuation
- 1999-07-13 CN CN99807294A patent/CN1127486C/zh not_active Expired - Fee Related
- 1999-07-13 UA UA2001010439A patent/UA68383C2/uk unknown
- 1999-07-13 HU HU0102646A patent/HUP0102646A3/hu unknown
- 1999-07-13 ID IDW20010132A patent/ID28874A/id unknown
- 1999-07-13 NZ NZ507926A patent/NZ507926A/xx unknown
- 1999-07-13 EA EA200100062A patent/EA200100062A1/ru unknown
- 1999-07-13 EP EP03102377A patent/EP1371648A1/en not_active Withdrawn
- 1999-07-13 BR BR9911175-6A patent/BR9911175A/pt not_active IP Right Cessation
- 1999-07-13 EE EEP200100039A patent/EE200100039A/xx unknown
- 1999-07-16 AR ARP990103501A patent/AR019409A1/es unknown
- 1999-07-19 CO CO99045518A patent/CO5090842A1/es unknown
- 1999-07-19 TW TW088112218A patent/TW509682B/zh not_active IP Right Cessation
- 1999-07-19 PA PA19998478301A patent/PA8478301A1/es unknown
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2000
- 2000-12-15 IS IS5772A patent/IS5772A/is unknown
- 2000-12-18 BG BG105063A patent/BG105063A/xx unknown
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2001
- 2001-01-19 NO NO20010331A patent/NO318988B1/no not_active IP Right Cessation
- 2001-01-22 HR HR20010057A patent/HRP20010057A2/hr not_active Application Discontinuation
- 2001-10-15 US US09/976,436 patent/US6492360B1/en not_active Expired - Fee Related
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2002
- 2002-01-25 HK HK02100584.0A patent/HK1039124B/zh not_active IP Right Cessation
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