ZA200408849B - New piperidinyl-alkylamino-pyridazinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing said compounds - Google Patents
New piperidinyl-alkylamino-pyridazinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing said compounds Download PDFInfo
- Publication number
- ZA200408849B ZA200408849B ZA200408849A ZA200408849A ZA200408849B ZA 200408849 B ZA200408849 B ZA 200408849B ZA 200408849 A ZA200408849 A ZA 200408849A ZA 200408849 A ZA200408849 A ZA 200408849A ZA 200408849 B ZA200408849 B ZA 200408849B
- Authority
- ZA
- South Africa
- Prior art keywords
- general formula
- hal
- alkylamino
- piperidinyl
- acid addition
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 23
- 238000000034 method Methods 0.000 title claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 239000002253 acid Substances 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 230000000949 anxiolytic effect Effects 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 208000019901 Anxiety disease Diseases 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 7
- 238000009903 catalytic hydrogenation reaction Methods 0.000 claims description 7
- 239000002249 anxiolytic agent Substances 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- FSBUHRJTFGPCPV-UHFFFAOYSA-N 5-[2-[4-(4-fluoro-2-hydroxybenzoyl)piperidin-1-yl]ethylamino]-2-methylpyridazin-3-one Chemical compound O=C1N(C)N=CC(NCCN2CCC(CC2)C(=O)C=2C(=CC(F)=CC=2)O)=C1 FSBUHRJTFGPCPV-UHFFFAOYSA-N 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 description 6
- 239000007858 starting material Substances 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 230000036506 anxiety Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 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 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-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
- 229960003529 diazepam Drugs 0.000 description 3
- 230000037023 motor activity Effects 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000001624 sedative effect Effects 0.000 description 3
- 230000002269 spontaneous effect Effects 0.000 description 3
- SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
- 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
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 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
- 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
- 239000000010 aprotic solvent Substances 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 125000003310 benzodiazepinyl group Chemical group N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000003586 protic polar solvent Substances 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
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 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 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
- -1 3-(1-substituted-4-piperidinyl)-1,2-benzisoxazole Chemical class 0.000 description 1
- CCJRACIGPHNCTO-UHFFFAOYSA-N 5-[2-[4-(4-fluoro-2-hydroxybenzoyl)piperidin-1-yl]propylamino]-2-methylpyridazin-3-one Chemical compound C1CC(C(=O)C=2C(=CC(F)=CC=2)O)CCN1C(C)CNC=1C=NN(C)C(=O)C=1 CCJRACIGPHNCTO-UHFFFAOYSA-N 0.000 description 1
- MRMGJMGHPJZSAE-UHFFFAOYSA-N 6-fluoro-3-piperidin-4-yl-1,2-benzoxazole Chemical compound N=1OC2=CC(F)=CC=C2C=1C1CCNCC1 MRMGJMGHPJZSAE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-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
- 208000011688 Generalised anxiety disease Diseases 0.000 description 1
- NPPQSCRMBWNHMW-UHFFFAOYSA-N Meprobamate Chemical compound NC(=O)OCC(C)(CCC)COC(N)=O NPPQSCRMBWNHMW-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 206010039897 Sedation 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
- 230000002411 adverse Effects 0.000 description 1
- 125000000217 alkyl group Chemical group 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
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 229940005530 anxiolytics Drugs 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
- 239000011230 binding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 229960003120 clonazepam Drugs 0.000 description 1
- DGBIGWXXNGSACT-UHFFFAOYSA-N clonazepam Chemical compound C12=CC([N+](=O)[O-])=CC=C2NC(=O)CN=C1C1=CC=CC=C1Cl DGBIGWXXNGSACT-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 208000029364 generalized anxiety disease Diseases 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 150000002500 ions Chemical class 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
- 230000002045 lasting effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 229960004815 meprobamate Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000003158 myorelaxant agent Substances 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
- 239000003176 neuroleptic agent Substances 0.000 description 1
- 230000000701 neuroleptic effect Effects 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
- 208000019906 panic disease Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 208000028173 post-traumatic stress disease Diseases 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000000611 regression analysis Methods 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000036280 sedation Effects 0.000 description 1
- 239000000932 sedative agent 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
- 238000013222 sprague-dawley male rat Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000005208 trialkylammonium group Chemical group 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
- 238000005303 weighing 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
-
- 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
- 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
- A61P25/22—Anxiolytics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU0201374A HU227255B1 (en) | 2002-04-26 | 2002-04-26 | Novel piperidine-alkyl-amino-pyridazine derivatives, pharmaceutical compositions containing the same and process for the preparation of the active ingredient |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200408849B true ZA200408849B (en) | 2006-09-27 |
Family
ID=89980388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200408849A ZA200408849B (en) | 2002-04-26 | 2002-12-28 | New piperidinyl-alkylamino-pyridazinone derivatives, a process for the preparation thereof and pharmaceutical compositions containing said compounds |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US7183283B2 (cs) |
| EP (1) | EP1501823B1 (cs) |
| JP (1) | JP2005526113A (cs) |
| KR (1) | KR20040104608A (cs) |
| CN (1) | CN1289495C (cs) |
| AT (1) | ATE312091T1 (cs) |
| AU (1) | AU2002356351A1 (cs) |
| BR (1) | BR0215672A (cs) |
| CA (1) | CA2480293A1 (cs) |
| CY (1) | CY1105422T1 (cs) |
| CZ (1) | CZ20041085A3 (cs) |
| DE (1) | DE60207895T2 (cs) |
| DK (1) | DK1501823T3 (cs) |
| EA (1) | EA007202B1 (cs) |
| ES (1) | ES2254793T3 (cs) |
| HU (1) | HU227255B1 (cs) |
| MX (1) | MXPA04010411A (cs) |
| NO (1) | NO20045124L (cs) |
| NZ (1) | NZ536639A (cs) |
| PL (1) | PL371520A1 (cs) |
| SI (1) | SI1501823T1 (cs) |
| SK (1) | SK50162004A3 (cs) |
| WO (1) | WO2003091244A1 (cs) |
| ZA (1) | ZA200408849B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102004010207A1 (de) * | 2004-03-02 | 2005-09-15 | Aventis Pharma S.A. | Neue 4-Benzimidazol-2-yl-pyridazin-3-on-Derivate |
| HUP0600555A3 (en) * | 2006-07-03 | 2008-10-28 | Egis Gyogyszergyar Nyrt | Use of 4-chloro-5-{2-[4-(6-fluoro-1,2-benz[d]izoxazol-3-yl)piperidin-1-yl]ethylamino}2-methyl-3(2h)-piridazinon for the production of pharmaceutical compositions for influencing cognitive functions and causing neuroprotective effect |
| US20100211495A1 (en) * | 2009-02-13 | 2010-08-19 | Bank Of America Corporation | Systems, methods and computer program products for improving foreign currency exchange in a comprehensive payment hub system |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU225955B1 (en) | 2001-07-26 | 2008-01-28 | Egis Gyogyszergyar Nyilvanosan | Novel 2h-pyridazin-3-one derivatives, process for their preparation, their use and pharmaceutical compositions containing them |
-
2002
- 2002-04-26 HU HU0201374A patent/HU227255B1/hu not_active IP Right Cessation
- 2002-12-28 AT AT02807294T patent/ATE312091T1/de not_active IP Right Cessation
- 2002-12-28 EA EA200401417A patent/EA007202B1/ru not_active IP Right Cessation
- 2002-12-28 DK DK02807294T patent/DK1501823T3/da active
- 2002-12-28 DE DE60207895T patent/DE60207895T2/de not_active Expired - Fee Related
- 2002-12-28 CA CA002480293A patent/CA2480293A1/en not_active Abandoned
- 2002-12-28 CN CNB028288165A patent/CN1289495C/zh not_active Expired - Fee Related
- 2002-12-28 NZ NZ536639A patent/NZ536639A/en unknown
- 2002-12-28 AU AU2002356351A patent/AU2002356351A1/en not_active Abandoned
- 2002-12-28 BR BR0215672-5A patent/BR0215672A/pt not_active IP Right Cessation
- 2002-12-28 KR KR10-2004-7017067A patent/KR20040104608A/ko not_active Withdrawn
- 2002-12-28 SI SI200230281T patent/SI1501823T1/sl unknown
- 2002-12-28 JP JP2003587802A patent/JP2005526113A/ja not_active Withdrawn
- 2002-12-28 EP EP02807294A patent/EP1501823B1/en not_active Expired - Lifetime
- 2002-12-28 US US10/508,676 patent/US7183283B2/en not_active Expired - Fee Related
- 2002-12-28 ZA ZA200408849A patent/ZA200408849B/en unknown
- 2002-12-28 PL PL02371520A patent/PL371520A1/xx unknown
- 2002-12-28 CZ CZ20041085A patent/CZ20041085A3/cs unknown
- 2002-12-28 ES ES02807294T patent/ES2254793T3/es not_active Expired - Lifetime
- 2002-12-28 SK SK5016-2004A patent/SK50162004A3/sk unknown
- 2002-12-28 MX MXPA04010411A patent/MXPA04010411A/es unknown
- 2002-12-28 WO PCT/HU2002/000171 patent/WO2003091244A1/en active IP Right Grant
-
2004
- 2004-11-24 NO NO20045124A patent/NO20045124L/no not_active Application Discontinuation
-
2006
- 2006-03-01 CY CY20061100286T patent/CY1105422T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1501823B1 (en) | 2005-12-07 |
| EP1501823A1 (en) | 2005-02-02 |
| SK50162004A3 (sk) | 2005-06-02 |
| HUP0201374A2 (hu) | 2005-01-28 |
| CN1289495C (zh) | 2006-12-13 |
| SI1501823T1 (sl) | 2006-06-30 |
| US7183283B2 (en) | 2007-02-27 |
| US20050215560A1 (en) | 2005-09-29 |
| MXPA04010411A (es) | 2005-02-17 |
| NO20045124L (no) | 2004-11-24 |
| DE60207895T2 (de) | 2006-08-10 |
| DE60207895D1 (de) | 2006-01-12 |
| JP2005526113A (ja) | 2005-09-02 |
| CN1630652A (zh) | 2005-06-22 |
| BR0215672A (pt) | 2005-02-01 |
| CZ20041085A3 (cs) | 2005-10-12 |
| CY1105422T1 (el) | 2010-04-28 |
| NZ536639A (en) | 2006-09-29 |
| WO2003091244A1 (en) | 2003-11-06 |
| AU2002356351A1 (en) | 2003-11-10 |
| HU0201374D0 (cs) | 2002-06-29 |
| EA200401417A1 (ru) | 2005-04-28 |
| DK1501823T3 (da) | 2006-04-10 |
| CA2480293A1 (en) | 2003-11-06 |
| ATE312091T1 (de) | 2005-12-15 |
| KR20040104608A (ko) | 2004-12-10 |
| HU227255B1 (en) | 2010-12-28 |
| ES2254793T3 (es) | 2006-06-16 |
| EA007202B1 (ru) | 2006-08-25 |
| HK1075656A1 (en) | 2005-12-23 |
| PL371520A1 (en) | 2005-06-27 |
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