NO326370B1 - Substituerte alkylaminopyridazinonderivater, fremgangsmate til fremstilling derav, anvendelse derav, farmasoytisk sammensetning som inneholder dem og fremgangsmate for fremstilling av sammensetningene - Google Patents
Substituerte alkylaminopyridazinonderivater, fremgangsmate til fremstilling derav, anvendelse derav, farmasoytisk sammensetning som inneholder dem og fremgangsmate for fremstilling av sammensetningene Download PDFInfo
- Publication number
- NO326370B1 NO326370B1 NO20041551A NO20041551A NO326370B1 NO 326370 B1 NO326370 B1 NO 326370B1 NO 20041551 A NO20041551 A NO 20041551A NO 20041551 A NO20041551 A NO 20041551A NO 326370 B1 NO326370 B1 NO 326370B1
- Authority
- NO
- Norway
- Prior art keywords
- general formula
- acid addition
- pharmaceutically acceptable
- acceptable acid
- hydrogen
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 12
- 239000000203 mixture Substances 0.000 title description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 46
- 239000002253 acid Substances 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 239000001257 hydrogen Substances 0.000 claims abstract description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910052736 halogen Chemical group 0.000 claims abstract description 17
- 150000002367 halogens Chemical group 0.000 claims abstract description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 16
- 230000000949 anxiolytic effect Effects 0.000 claims abstract description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 239000002249 anxiolytic agent Substances 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 7
- 150000002431 hydrogen Chemical class 0.000 claims abstract 4
- 150000001875 compounds Chemical class 0.000 claims description 58
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- JCMVXCLLRPDLRG-UHFFFAOYSA-N 4-[2-(4-phenylpiperazin-1-yl)ethylamino]-1h-pyridazin-6-one Chemical group C1=NNC(=O)C=C1NCCN1CCN(C=2C=CC=CC=2)CC1 JCMVXCLLRPDLRG-UHFFFAOYSA-N 0.000 claims description 3
- AVVQYCNDMYIPGU-UHFFFAOYSA-N 4-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical group FC1=CC=CC=C1N1CCN(CCNC2=CC(=O)NN=C2)CC1 AVVQYCNDMYIPGU-UHFFFAOYSA-N 0.000 claims description 3
- TWMKPFQMPCZCRH-UHFFFAOYSA-N 4-[2-[4-(3-chlorophenyl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical group ClC1=CC=CC(N2CCN(CCNC3=CC(=O)NN=C3)CC2)=C1 TWMKPFQMPCZCRH-UHFFFAOYSA-N 0.000 claims description 3
- NTTYWJGVUNURRC-UHFFFAOYSA-N 4-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical group C1=CC(F)=CC=C1N1CCN(CCNC2=CC(=O)NN=C2)CC1 NTTYWJGVUNURRC-UHFFFAOYSA-N 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 238000005695 dehalogenation reaction Methods 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 3
- MFXXTCPZOTXOOV-UHFFFAOYSA-N 4-[2-(4-pyridin-2-ylpiperazin-1-yl)ethylamino]-1h-pyridazin-6-one Chemical group C1=NNC(=O)C=C1NCCN1CCN(C=2N=CC=CC=2)CC1 MFXXTCPZOTXOOV-UHFFFAOYSA-N 0.000 claims description 2
- DXDDHJZKNLUJQT-UHFFFAOYSA-N 4-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethylamino]-1h-pyridazin-6-one Chemical group C1=NNC(=O)C=C1NCCN1CCN(C=2N=CC=CN=2)CC1 DXDDHJZKNLUJQT-UHFFFAOYSA-N 0.000 claims description 2
- FYOKKHAZSGICQN-UHFFFAOYSA-N 4-[2-[4-[3-methoxy-2-(trifluoromethyl)phenyl]piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical group COC1=CC=CC(N2CCN(CCNC3=CC(=O)NN=C3)CC2)=C1C(F)(F)F FYOKKHAZSGICQN-UHFFFAOYSA-N 0.000 claims description 2
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 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 description 3
- 230000001737 promoting effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 241001465754 Metazoa Species 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 230000000694 effects Effects 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000003054 catalyst Substances 0.000 description 13
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- 239000000706 filtrate Substances 0.000 description 11
- 230000035939 shock Effects 0.000 description 10
- -1 methoxy, ethoxy, isopropoxy Chemical group 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000013078 crystal Substances 0.000 description 8
- 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 8
- 239000000243 solution Substances 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- 229960003529 diazepam Drugs 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 229910052763 palladium Inorganic materials 0.000 description 7
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
- 241000700159 Rattus Species 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 230000001624 sedative effect Effects 0.000 description 6
- 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 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 5
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 5
- 239000003981 vehicle Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 229920005372 Plexiglas® Polymers 0.000 description 4
- 239000012153 distilled water Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000013558 reference substance Substances 0.000 description 4
- 239000000932 sedative agent Substances 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 208000019901 Anxiety disease Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical group COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 241000700157 Rattus norvegicus Species 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229940049706 benzodiazepine Drugs 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 230000036772 blood pressure Effects 0.000 description 3
- 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
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 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
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000003276 anti-hypertensive effect Effects 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 239000000010 aprotic solvent Substances 0.000 description 2
- 230000004872 arterial blood pressure Effects 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 229960002495 buspirone Drugs 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 230000013016 learning Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- 230000037023 motor activity Effects 0.000 description 2
- 239000003586 protic polar solvent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 230000002269 spontaneous effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VHFVKMTVMIZMIK-UHFFFAOYSA-N 1-(3-chlorophenyl)piperazine Chemical compound ClC1=CC=CC(N2CCNCC2)=C1 VHFVKMTVMIZMIK-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- QQCAYIPEZKIOBL-UHFFFAOYSA-N 4-(2-chloroethylamino)-1h-pyridazin-6-one;hydrochloride Chemical compound Cl.ClCCNC=1C=NNC(=O)C=1 QQCAYIPEZKIOBL-UHFFFAOYSA-N 0.000 description 1
- NUTOCYSJAIPZHN-UHFFFAOYSA-N 5-chloro-4-[2-(4-phenylpiperazin-1-yl)ethylamino]-1h-pyridazin-6-one Chemical compound C1=NNC(=O)C(Cl)=C1NCCN1CCN(C=2C=CC=CC=2)CC1 NUTOCYSJAIPZHN-UHFFFAOYSA-N 0.000 description 1
- JNKUDKXJUIZFMT-UHFFFAOYSA-N 5-chloro-4-[2-(4-pyridin-2-ylpiperazin-1-yl)ethylamino]-1h-pyridazin-6-one Chemical compound C1=NNC(=O)C(Cl)=C1NCCN1CCN(C=2N=CC=CC=2)CC1 JNKUDKXJUIZFMT-UHFFFAOYSA-N 0.000 description 1
- BTEIGBDNRMWUON-UHFFFAOYSA-N 5-chloro-4-[2-(4-pyrimidin-2-ylpiperazin-1-yl)ethylamino]-1h-pyridazin-6-one Chemical compound C1=NNC(=O)C(Cl)=C1NCCN1CCN(C=2N=CC=CN=2)CC1 BTEIGBDNRMWUON-UHFFFAOYSA-N 0.000 description 1
- LZULALWFIKWMCH-UHFFFAOYSA-N 5-chloro-4-[2-[4-(2-fluorophenyl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical compound FC1=CC=CC=C1N1CCN(CCNC2=C(C(=O)NN=C2)Cl)CC1 LZULALWFIKWMCH-UHFFFAOYSA-N 0.000 description 1
- VLJHTSDAIXPOPT-UHFFFAOYSA-N 5-chloro-4-[2-[4-(4-fluorophenyl)piperazin-1-yl]ethylamino]-1h-pyridazin-6-one Chemical compound C1=CC(F)=CC=C1N1CCN(CCNC2=C(C(=O)NN=C2)Cl)CC1 VLJHTSDAIXPOPT-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010052804 Drug tolerance Diseases 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000010029 Homer Scaffolding Proteins Human genes 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000006264 Korsakoff syndrome Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 201000008485 Wernicke-Korsakoff syndrome Diseases 0.000 description 1
- 210000003815 abdominal wall Anatomy 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229960004538 alprazolam Drugs 0.000 description 1
- VREFGVBLTWBCJP-UHFFFAOYSA-N alprazolam Chemical compound C12=CC(Cl)=CC=C2N2C(C)=NN=C2CN=C1C1=CC=CC=C1 VREFGVBLTWBCJP-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003109 amnesic effect Effects 0.000 description 1
- 238000000540 analysis of variance Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002180 anti-stress Effects 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 229960004782 chlordiazepoxide Drugs 0.000 description 1
- ANTSCNMPPGJYLG-UHFFFAOYSA-N chlordiazepoxide Chemical compound O=N=1CC(NC)=NC2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 ANTSCNMPPGJYLG-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 208000028831 congenital heart disease Diseases 0.000 description 1
- 239000012050 conventional carrier Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 230000035622 drinking Effects 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000007941 film coated tablet Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000001727 glucose Nutrition 0.000 description 1
- 230000026781 habituation Effects 0.000 description 1
- 239000003906 humectant Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 230000028252 learning or memory Effects 0.000 description 1
- 238000012153 long-term therapy Methods 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000003340 mental effect Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229940105631 nembutal Drugs 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 238000010149 post-hoc-test Methods 0.000 description 1
- 230000002980 postoperative effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 238000011160 research Methods 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
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000007619 statistical method Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000003440 toxic substance Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000007492 two-way ANOVA Methods 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
- C07D401/12—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)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (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/HU2002/000097 WO2003027078A1 (en) | 2001-09-27 | 2002-09-26 | Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO20041551L NO20041551L (no) | 2004-06-10 |
| NO326370B1 true NO326370B1 (no) | 2008-11-17 |
Family
ID=89979721
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20041551A NO326370B1 (no) | 2001-09-27 | 2004-04-16 | Substituerte alkylaminopyridazinonderivater, fremgangsmate til fremstilling derav, anvendelse derav, farmasoytisk sammensetning som inneholder dem og fremgangsmate for fremstilling av sammensetningene |
| NO20041704A NO325080B1 (no) | 2001-09-27 | 2004-04-26 | Substituerte alkylaminopyridazinonderivater, fremgangsmater til deres fremstilling, og farmasoytiske sammensetninger som inneholder disse, fremgangsmate til fremstilling av sammensetningen og anvendelse av derivatene til a fremstille farmasoytiske preparater. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20041704A NO325080B1 (no) | 2001-09-27 | 2004-04-26 | Substituerte alkylaminopyridazinonderivater, fremgangsmater til deres fremstilling, og farmasoytiske sammensetninger som inneholder disse, fremgangsmate til fremstilling av sammensetningen og anvendelse av derivatene til a fremstille farmasoytiske preparater. |
Country Status (26)
| Country | Link |
|---|---|
| US (2) | US6930110B2 (es) |
| EP (2) | EP1430047B1 (es) |
| JP (2) | JP4472337B2 (es) |
| KR (2) | KR100911069B1 (es) |
| CN (3) | CN100368404C (es) |
| AT (2) | ATE288899T1 (es) |
| AU (2) | AU2002328166B2 (es) |
| BR (2) | BR0212932A (es) |
| CA (2) | CA2461467A1 (es) |
| CZ (2) | CZ2004528A3 (es) |
| DE (2) | DE60202969T2 (es) |
| DK (2) | DK1430047T3 (es) |
| EA (2) | EA006942B1 (es) |
| ES (2) | ES2237696T3 (es) |
| HK (3) | HK1069816A1 (es) |
| HU (1) | HU227237B1 (es) |
| MA (2) | MA27068A1 (es) |
| MX (2) | MXPA04002836A (es) |
| NO (2) | NO326370B1 (es) |
| NZ (2) | NZ532103A (es) |
| PL (2) | PL369256A1 (es) |
| PT (2) | PT1430034E (es) |
| SI (2) | SI1430034T1 (es) |
| SK (2) | SK1902004A3 (es) |
| WO (2) | WO2003027097A1 (es) |
| ZA (2) | ZA200402544B (es) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE424825T1 (de) | 2001-07-20 | 2009-03-15 | Psychogenics Inc | Behandlung von hyperaktivitätsstörungen und aufmerksamkeitsdefiziten |
| 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 |
| AU2008227100B2 (en) * | 2007-03-15 | 2014-01-09 | Albany Molecular Research, Inc. | Pyridazinone derivatives useful as glucan synthase inhibitors |
| BR112020022006A2 (pt) * | 2018-04-30 | 2021-01-26 | Ribon Therapeutics Inc. | piridazinonas como inibidores de parp7 |
| 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 |
| CN117425648A (zh) * | 2021-03-12 | 2024-01-19 | 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 |
|---|---|---|---|---|
| CH557819A (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 |
| AU752967B2 (en) | 1998-06-05 | 2002-10-03 | Egis Gyogyszergyar Rt. | Process for the preparation of a 3(2H)-pyridazinone- 4-substituted amino- 5-chloro- derivative |
-
2001
- 2001-09-27 HU HU0103912A patent/HU227237B1/hu not_active IP Right Cessation
-
2002
- 2002-09-26 DE DE60202969T patent/DE60202969T2/de not_active Expired - Lifetime
- 2002-09-26 MX MXPA04002836A patent/MXPA04002836A/es active IP Right Grant
- 2002-09-26 US US10/491,151 patent/US6930110B2/en not_active Expired - Fee Related
- 2002-09-26 CZ CZ2004528A patent/CZ2004528A3/cs unknown
- 2002-09-26 PL PL02369256A patent/PL369256A1/xx unknown
- 2002-09-26 KR KR1020047004607A patent/KR100911069B1/ko not_active IP Right Cessation
- 2002-09-26 SK SK1902004A patent/SK1902004A3/sk unknown
- 2002-09-26 DE DE60202970T patent/DE60202970T2/de not_active Expired - Lifetime
- 2002-09-26 BR BR0212932-9A patent/BR0212932A/pt not_active IP Right Cessation
- 2002-09-26 AU AU2002328166A patent/AU2002328166B2/en not_active Ceased
- 2002-09-26 JP JP2003530685A patent/JP4472337B2/ja not_active Expired - Lifetime
- 2002-09-26 WO PCT/HU2002/000096 patent/WO2003027097A1/en active IP Right Grant
- 2002-09-26 CA CA002461467A patent/CA2461467A1/en not_active Abandoned
- 2002-09-26 ES ES02767729T patent/ES2237696T3/es not_active Expired - Lifetime
- 2002-09-26 CN CNB028189752A patent/CN100368404C/zh not_active Expired - Fee Related
- 2002-09-26 DK DK02762620T patent/DK1430047T3/da active
- 2002-09-26 DK DK02767729T patent/DK1430034T3/da active
- 2002-09-26 CZ CZ2004532A patent/CZ2004532A3/cs unknown
- 2002-09-26 ES ES02762620T patent/ES2237690T3/es not_active Expired - Lifetime
- 2002-09-26 KR KR1020047004606A patent/KR100890667B1/ko not_active IP Right Cessation
- 2002-09-26 BR BR0212839-0A patent/BR0212839A/pt not_active IP Right Cessation
- 2002-09-26 JP JP2003530669A patent/JP2005508914A/ja active Pending
- 2002-09-26 EP EP02762620A patent/EP1430047B1/en not_active Expired - Lifetime
- 2002-09-26 SI SI200230107T patent/SI1430034T1/xx unknown
- 2002-09-26 EP EP02767729A patent/EP1430034B1/en not_active Expired - Lifetime
- 2002-09-26 CN CNB028204425A patent/CN1325489C/zh not_active Expired - Fee Related
- 2002-09-26 PL PL02369107A patent/PL369107A1/xx not_active IP Right Cessation
- 2002-09-26 AT AT02767729T patent/ATE288899T1/de not_active IP Right Cessation
- 2002-09-26 SI SI200230109T patent/SI1430047T1/xx unknown
- 2002-09-26 AU AU2002330656A patent/AU2002330656B9/en not_active Ceased
- 2002-09-26 US US10/490,959 patent/US20050043314A1/en not_active Abandoned
- 2002-09-26 AT AT02762620T patent/ATE288910T1/de not_active IP Right Cessation
- 2002-09-26 CN CN200710104934XA patent/CN101099740B/zh not_active Expired - Fee Related
- 2002-09-26 NZ NZ532103A patent/NZ532103A/en unknown
- 2002-09-26 NZ NZ532104A patent/NZ532104A/en unknown
- 2002-09-26 WO PCT/HU2002/000097 patent/WO2003027078A1/en active IP Right Grant
- 2002-09-26 PT PT02767729T patent/PT1430034E/pt unknown
- 2002-09-26 MX MXPA04002838A patent/MXPA04002838A/es active IP Right Grant
- 2002-09-26 SK SK1892004A patent/SK1892004A3/sk unknown
- 2002-09-26 CA CA002461510A patent/CA2461510C/en not_active Expired - Fee Related
- 2002-09-26 EA EA200400470A patent/EA006942B1/ru not_active IP Right Cessation
- 2002-09-26 PT PT02762620T patent/PT1430047E/pt unknown
- 2002-09-26 EA EA200400469A patent/EA006392B1/ru not_active IP Right Cessation
-
2004
- 2004-03-24 MA MA27589A patent/MA27068A1/fr unknown
- 2004-03-24 MA MA27588A patent/MA27137A1/fr unknown
- 2004-03-31 ZA ZA200402544A patent/ZA200402544B/en unknown
- 2004-03-31 ZA ZA200402545A patent/ZA200402545B/en unknown
- 2004-04-16 NO NO20041551A patent/NO326370B1/no not_active IP Right Cessation
- 2004-04-26 NO NO20041704A patent/NO325080B1/no not_active IP Right Cessation
- 2004-12-23 HK HK04110210A patent/HK1069816A1/xx not_active IP Right Cessation
- 2004-12-23 HK HK04110211A patent/HK1069817A1/xx not_active IP Right Cessation
-
2008
- 2008-05-26 HK HK08105825.2A patent/HK1115728A1/xx not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO326370B1 (no) | Substituerte alkylaminopyridazinonderivater, fremgangsmate til fremstilling derav, anvendelse derav, farmasoytisk sammensetning som inneholder dem og fremgangsmate for fremstilling av sammensetningene | |
| AU2002330656A1 (en) | Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same | |
| JP2005508914A5 (es) | ||
| AU2002328166A1 (en) | Substituted alkylaminopyridazinone derivatives, process for the preparation thereof and pharmaceutical composition containing the same | |
| KR20040104608A (ko) | 피페리디닐-알킬아미노-피리다지논 유도체, 이의 제조방법, 및 이 화합물을 함유하는 약제 조성물 | |
| WO2022020889A1 (en) | Method of treatment of cytomegalovirus | |
| HU227294B1 (en) | Substituted alkylpyridazone derivatives, process for their preparation and pharmaceutical compositions containing them | |
| CZ2005316A3 (cs) | Substituované alkyl-pyridazinony pro léčení selhávání paměti a učení |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |