SK1902004A3 - Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same - Google Patents
Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same Download PDFInfo
- Publication number
- SK1902004A3 SK1902004A3 SK1902004A SK1902004A SK1902004A3 SK 1902004 A3 SK1902004 A3 SK 1902004A3 SK 1902004 A SK1902004 A SK 1902004A SK 1902004 A SK1902004 A SK 1902004A SK 1902004 A3 SK1902004 A3 SK 1902004A3
- Authority
- SK
- Slovakia
- Prior art keywords
- formula
- pyridazin
- acid addition
- pharmaceutically acceptable
- dioxin
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 36
- 238000000034 method Methods 0.000 title claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 67
- 239000002253 acid Substances 0.000 claims abstract description 46
- 150000003839 salts Chemical class 0.000 claims abstract description 45
- 239000001257 hydrogen Substances 0.000 claims abstract description 37
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 35
- 229910052736 halogen Chemical group 0.000 claims abstract description 31
- 150000002367 halogens Chemical group 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 230000000949 anxiolytic effect Effects 0.000 claims abstract description 13
- 239000002249 anxiolytic agent Substances 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 101
- -1 2,3-dihydrobenzo [1,4] dioxin-5-yl Chemical group 0.000 claims description 47
- 239000000460 chlorine Chemical group 0.000 claims description 31
- 229910052801 chlorine Chemical group 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
- 239000004480 active ingredient Substances 0.000 claims description 10
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 10
- 125000004193 piperazinyl group Chemical group 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000006308 propyl amino group Chemical group 0.000 claims description 4
- 229910052727 yttrium Inorganic materials 0.000 claims description 4
- DGIKIRMOQMLKFR-UHFFFAOYSA-N 5-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylamino]-2-methylpyridazin-3-one Chemical compound O=C1N(C)N=CC(NCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1 DGIKIRMOQMLKFR-UHFFFAOYSA-N 0.000 claims description 3
- 238000005695 dehalogenation reaction Methods 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- CRCCDLXNBMVXRE-UHFFFAOYSA-N 4-[3-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]propylamino]-1h-pyridazin-6-one Chemical compound C1=NNC(=O)C=C1NCCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 CRCCDLXNBMVXRE-UHFFFAOYSA-N 0.000 claims description 2
- UYXYHHBVFZUVNC-UHFFFAOYSA-N 4-chloro-5-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethyl-methylamino]-2-methylpyridazin-3-one Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CCN(C)C=1C=NN(C)C(=O)C=1Cl UYXYHHBVFZUVNC-UHFFFAOYSA-N 0.000 claims description 2
- OVSWGEFJLVHBKZ-UHFFFAOYSA-N 5-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethyl-methylamino]-2-methylpyridazin-3-one Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CCN(C)C=1C=NN(C)C(=O)C=1 OVSWGEFJLVHBKZ-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- SIVUQQKXULHTJR-UHFFFAOYSA-N 4-chloro-5-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylamino]-2-methylpyridazin-3-one Chemical compound O=C1N(C)N=CC(NCCN2CCN(CC2)C=2C=3OCCOC=3C=CC=2)=C1Cl SIVUQQKXULHTJR-UHFFFAOYSA-N 0.000 claims 2
- 239000012752 auxiliary agent Substances 0.000 claims 2
- ODABSAWZAHDAPT-UHFFFAOYSA-N 2-(methylamino)pyridazin-3-one Chemical compound CNN1N=CC=CC1=O ODABSAWZAHDAPT-UHFFFAOYSA-N 0.000 claims 1
- GGULBKLAHUMRAL-UHFFFAOYSA-N 4-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethyl-methylamino]-1h-pyridazin-6-one Chemical compound C1CN(C=2C=3OCCOC=3C=CC=2)CCN1CCN(C)C=1C=NNC(=O)C=1 GGULBKLAHUMRAL-UHFFFAOYSA-N 0.000 claims 1
- XGVHQXGZCSWXEO-UHFFFAOYSA-N 4-[2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical compound C1=NNC(=O)C=C1NCCN1CCN(C=2C=3OCCOC=3C=CC=2)CC1 XGVHQXGZCSWXEO-UHFFFAOYSA-N 0.000 claims 1
- HFOPNMQVKOCZIF-UHFFFAOYSA-N 4-[2-[4-(7-chloro-2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical compound C=1C(Cl)=CC=2OCCOC=2C=1N(CC1)CCN1CCNC=1C=NNC(=O)C=1 HFOPNMQVKOCZIF-UHFFFAOYSA-N 0.000 claims 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 1
- 230000019771 cognition Effects 0.000 abstract 1
- 230000002708 enhancing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 229910052757 nitrogen Inorganic materials 0.000 description 31
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 27
- 238000012360 testing method Methods 0.000 description 27
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
- 239000011541 reaction mixture Substances 0.000 description 23
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 241001465754 Metazoa Species 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- 238000004458 analytical method Methods 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- 230000000694 effects Effects 0.000 description 13
- 238000010992 reflux Methods 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 229960003529 diazepam Drugs 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
- 230000035939 shock Effects 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 229910052799 carbon Inorganic materials 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 239000003480 eluent Substances 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
- 229910002027 silica gel Inorganic materials 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 230000001624 sedative effect Effects 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
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- 239000012043 crude product Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- 208000019901 Anxiety disease Diseases 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
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- 229920005372 Plexiglas® Polymers 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
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- 238000001816 cooling Methods 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- WVLHGCRWEHCIOT-UHFFFAOYSA-N eltoprazine Chemical compound C1CNCCN1C1=CC=CC2=C1OCCO2 WVLHGCRWEHCIOT-UHFFFAOYSA-N 0.000 description 4
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- 230000035515 penetration Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- YPJDGPDZLPYDNJ-UHFFFAOYSA-N 5-(3-bromopropylamino)-4-chloro-1h-pyridazin-6-one Chemical compound ClC=1C=NNC(=O)C=1NCCCBr YPJDGPDZLPYDNJ-UHFFFAOYSA-N 0.000 description 3
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- QWCRAEMEVRGPNT-UHFFFAOYSA-N buspirone Chemical compound C1C(=O)N(CCCCN2CCN(CC2)C=2N=CC=CN=2)C(=O)CC21CCCC2 QWCRAEMEVRGPNT-UHFFFAOYSA-N 0.000 description 3
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- 238000005303 weighing Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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- 108010010803 Gelatin Proteins 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
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- YBOBVLITLCFBJV-UHFFFAOYSA-N 2-[4-(2,3-dihydro-1,4-benzodioxin-5-yl)piperazin-1-yl]ethanamine Chemical compound C1CN(CCN)CCN1C1=CC=CC2=C1OCCO2 YBOBVLITLCFBJV-UHFFFAOYSA-N 0.000 description 1
- IZQAUUVBKYXMET-UHFFFAOYSA-N 2-bromoethanamine Chemical compound NCCBr IZQAUUVBKYXMET-UHFFFAOYSA-N 0.000 description 1
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 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
- C07D401/12—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- C07D237/22—Nitrogen and oxygen atoms
-
- 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
- C07D403/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D405/12—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 chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Psychiatry (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0103912A HU227237B1 (en) | 2001-09-27 | 2001-09-27 | Substituted alkylpyridazinone derivatives, process for their preparation, pharmaceutical compositions containing them |
| PCT/HU2002/000096 WO2003027097A1 (en) | 2001-09-27 | 2002-09-26 | Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SK1902004A3 true SK1902004A3 (en) | 2004-10-05 |
Family
ID=89979721
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1892004A SK1892004A3 (en) | 2001-09-27 | 2002-09-26 | Substituted alkaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same |
| SK1902004A SK1902004A3 (en) | 2001-09-27 | 2002-09-26 | Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK1892004A SK1892004A3 (en) | 2001-09-27 | 2002-09-26 | Substituted alkaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US20050043314A1 (ja) |
| EP (2) | EP1430047B1 (ja) |
| JP (2) | JP4472337B2 (ja) |
| KR (2) | KR100911069B1 (ja) |
| CN (3) | CN1325489C (ja) |
| AT (2) | ATE288910T1 (ja) |
| AU (2) | AU2002330656B9 (ja) |
| BR (2) | BR0212932A (ja) |
| CA (2) | CA2461467A1 (ja) |
| CZ (2) | CZ2004528A3 (ja) |
| DE (2) | DE60202970T2 (ja) |
| DK (2) | DK1430034T3 (ja) |
| EA (2) | EA006392B1 (ja) |
| ES (2) | ES2237690T3 (ja) |
| HK (3) | HK1069817A1 (ja) |
| HU (1) | HU227237B1 (ja) |
| MA (2) | MA27137A1 (ja) |
| MX (2) | MXPA04002836A (ja) |
| NO (2) | NO326370B1 (ja) |
| NZ (2) | NZ532104A (ja) |
| PL (2) | PL369256A1 (ja) |
| PT (2) | PT1430047E (ja) |
| SI (2) | SI1430047T1 (ja) |
| SK (2) | SK1892004A3 (ja) |
| WO (2) | WO2003027078A1 (ja) |
| ZA (2) | ZA200402545B (ja) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1408976B3 (en) | 2001-07-20 | 2010-08-25 | Psychogenics Inc. | Treatment for attention-deficit hyperactivity disorder |
| HU227592B1 (en) * | 2002-11-13 | 2011-09-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | Use of substituted alkyl-piridazinone derivatives for the treatment of memory decline and learning malfunctions |
| JP5147866B2 (ja) * | 2007-03-15 | 2013-02-20 | メルク・シャープ・アンド・ドーム・コーポレーション | グルカン合成酵素阻害剤として有用であるピリダジノン誘導体 |
| CA3098585A1 (en) * | 2018-04-30 | 2019-11-07 | Ribon Therapeutics Inc. | Pyridazinones as parp7 inhibitors |
| CN109053693B (zh) | 2018-09-20 | 2021-02-05 | 顺毅股份有限公司 | 哒嗪胺类化合物的制备及其应用 |
| WO2022188889A1 (zh) * | 2021-03-12 | 2022-09-15 | 杭州英创医药科技有限公司 | 作为parp7抑制剂的化合物 |
| CN115490671B (zh) * | 2022-10-21 | 2024-05-14 | 水木未来(北京)科技有限公司 | Parp7抑制剂及其制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH557820A (de) * | 1970-11-12 | 1975-01-15 | Sandoz Ag | Verfahren zur herstellung von neuen 2-(2-hydroxyalkyl)4,5-dihydro-pyridazin (2h)-3-onen. |
| IE62890B1 (en) * | 1988-12-06 | 1995-03-08 | Hafslund Nycomed Pharma | New piperazinylalkyl-3(2h)-pyridazinones process for the preparation thereof and the use thereof as agents lowering blood pressure |
| PL164079B1 (pl) * | 1990-06-15 | 1994-06-30 | Akad Medyczna | posób wytwarzania nowych 2-amlnoalkilopochodnych 5-aminometyleno-6-/p-chlorofenylo /-4,5-dihydro-2H- plrydazyn -3-onu |
| HU209388B (en) * | 1990-12-27 | 1994-05-30 | Richter Gedeon Vegyeszet | Process for producing new 3/2h/-pyridazinones and pharmaceutical compositions comprising same |
| HU214320B (hu) | 1991-12-20 | 1998-03-02 | EGIS Gyógyszergyár Rt. | Eljárás új 3(2H)-piridazinon-származékok és ezeket tartalmazó gyógyszerkészítmények előállítására |
| HU224067B1 (hu) * | 1995-05-29 | 2005-05-30 | Gyógyszerkutató Intézet Kft. | 3(2H)-Piridazinon-származékok és e vegyületeket tartalmazó gyógyszerkészítmények |
| BR9815967A (pt) * | 1998-06-05 | 2004-06-22 | Egyt Gyogyszervegyeszeti Gyar | Processo para a preparação de um derivado de amino-5-cloro de 3(2h)-piridazinona-4-substituìdo |
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2001
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2002
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- 2002-09-26 CZ CZ2004532A patent/CZ2004532A3/cs unknown
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2004
- 2004-03-24 MA MA27588A patent/MA27137A1/fr unknown
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- 2004-03-31 ZA ZA200402545A patent/ZA200402545B/en unknown
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- 2004-04-16 NO NO20041551A patent/NO326370B1/no not_active IP Right Cessation
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