NO315118B1 - 1,2,4-triazolo[4,3-B]pyrido[3,2-D]pyridazinderivater samt farmasöytiske sammensetninger inneholdende slike - Google Patents
1,2,4-triazolo[4,3-B]pyrido[3,2-D]pyridazinderivater samt farmasöytiske sammensetninger inneholdende slike Download PDFInfo
- Publication number
- NO315118B1 NO315118B1 NO20000394A NO20000394A NO315118B1 NO 315118 B1 NO315118 B1 NO 315118B1 NO 20000394 A NO20000394 A NO 20000394A NO 20000394 A NO20000394 A NO 20000394A NO 315118 B1 NO315118 B1 NO 315118B1
- Authority
- NO
- Norway
- Prior art keywords
- group
- alkyl
- phenyl
- pyrido
- compound according
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title description 4
- DIAJZQVKZBSZCG-UHFFFAOYSA-N C1=CN=C2C=NN3C=NN=C3C2=C1 Chemical class C1=CN=C2C=NN3C=NN=C3C2=C1 DIAJZQVKZBSZCG-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 15
- -1 methylenedioxy- Chemical class 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000003085 diluting agent Substances 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims description 5
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims description 5
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 3
- 208000025865 Ulcer Diseases 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 231100000397 ulcer Toxicity 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
- FZOKILRFZOVKRQ-UHFFFAOYSA-N N=1N2C(CC(C)C)=NN=C2C2=CC=CN=C2C=1C1=CC=C(F)C=C1 Chemical compound N=1N2C(CC(C)C)=NN=C2C2=CC=CN=C2C=1C1=CC=C(F)C=C1 FZOKILRFZOVKRQ-UHFFFAOYSA-N 0.000 claims description 2
- YMNVGDHORTVWCT-UHFFFAOYSA-N [O-][N+](=O)C1=CC=CC(C=2C3=NC=CC=C3C3=NN=C(CC4CC4)N3N=2)=C1 Chemical compound [O-][N+](=O)C1=CC=CC(C=2C3=NC=CC=C3C3=NN=C(CC4CC4)N3N=2)=C1 YMNVGDHORTVWCT-UHFFFAOYSA-N 0.000 claims description 2
- CNINWDBQCDAKFK-UHFFFAOYSA-N [O-][N+](=O)C1=CC=CC(C=2C3=NC=CC=C3C3=NN=C(CC4CCC4)N3N=2)=C1 Chemical compound [O-][N+](=O)C1=CC=CC(C=2C3=NC=CC=C3C3=NN=C(CC4CCC4)N3N=2)=C1 CNINWDBQCDAKFK-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 208000026278 immune system disease Diseases 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical group C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 claims 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical group C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 claims 1
- XCJPTECQPSWMRE-UHFFFAOYSA-N 5-cyclopropyl-8-phenyl-3,4,6,7,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound C1CC1C1=NN=C2N1N=C(C=1C=CC=CC=1)C1=NC=CC=C12 XCJPTECQPSWMRE-UHFFFAOYSA-N 0.000 claims 1
- 206010020751 Hypersensitivity Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000026935 allergic disease Diseases 0.000 claims 1
- 208000030961 allergic reaction Diseases 0.000 claims 1
- 125000001887 cyclopentyloxy group Chemical group C1(CCCC1)O* 0.000 claims 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 150000002391 heterocyclic compounds Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910052698 phosphorus Inorganic materials 0.000 description 4
- 239000011574 phosphorus Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 101710111837 Cyclic phosphodiesterase Proteins 0.000 description 3
- 102000004127 Cytokines Human genes 0.000 description 3
- 108090000695 Cytokines Proteins 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000000903 blocking effect Effects 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- 150000002429 hydrazines Chemical class 0.000 description 3
- 150000007857 hydrazones Chemical class 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 230000000770 proinflammatory effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010012438 Dermatitis atopic Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000000172 allergic effect Effects 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 201000008937 atopic dermatitis Diseases 0.000 description 2
- 208000010668 atopic eczema Diseases 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000009109 curative therapy Methods 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000035475 disorder Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 239000003018 immunosuppressive agent Substances 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 2
- 229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 2
- 239000002571 phosphodiesterase inhibitor Substances 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- JVANLUCASVHWEW-UHFFFAOYSA-N pyridazine Chemical compound N1=C=C=C=C=N1 JVANLUCASVHWEW-UHFFFAOYSA-N 0.000 description 2
- WCKGRSPYFFVKQT-UHFFFAOYSA-N pyridazine;dihydrochloride Chemical compound Cl.Cl.C1=CC=NN=C1 WCKGRSPYFFVKQT-UHFFFAOYSA-N 0.000 description 2
- 239000012047 saturated solution Substances 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- DKACXUFSLUYRFU-UHFFFAOYSA-N tert-butyl n-aminocarbamate Chemical compound CC(C)(C)OC(=O)NN DKACXUFSLUYRFU-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- CUADCEFWXFDKEK-UHFFFAOYSA-N 2-benzoylpyridine-3-carboxylic acid Chemical compound OC(=O)C1=CC=CN=C1C(=O)C1=CC=CC=C1 CUADCEFWXFDKEK-UHFFFAOYSA-N 0.000 description 1
- RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 1
- SGTXILTYXULEQD-UHFFFAOYSA-N 2H-triazolo[4,5-f]phthalazine Chemical class N1=NC=C2C3=NNN=C3C=CC2=C1 SGTXILTYXULEQD-UHFFFAOYSA-N 0.000 description 1
- PNRSQGPMSVOCOE-UHFFFAOYSA-N 3-(2-methylpropyl)-6-phenyl-[1,2,4]triazolo[3,4-a]phthalazine Chemical compound N=1N2C(CC(C)C)=NN=C2C2=CC=CC=C2C=1C1=CC=CC=C1 PNRSQGPMSVOCOE-UHFFFAOYSA-N 0.000 description 1
- UYKXYJVJFRLVIF-UHFFFAOYSA-N 5-chloro-8-phenylpyrido[2,3-d]pyridazine Chemical compound C12=NC=CC=C2C(Cl)=NN=C1C1=CC=CC=C1 UYKXYJVJFRLVIF-UHFFFAOYSA-N 0.000 description 1
- LQGNAZVVIMUYDQ-UHFFFAOYSA-N 5-tert-butyl-8-phenyl-3,4,6,7,10-pentazatricyclo[7.4.0.02,6]trideca-1(9),2,4,7,10,12-hexaene Chemical compound N=1N2C(C(C)(C)C)=NN=C2C2=CC=CN=C2C=1C1=CC=CC=C1 LQGNAZVVIMUYDQ-UHFFFAOYSA-N 0.000 description 1
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 206010002660 Anoxia Diseases 0.000 description 1
- 241000976983 Anoxia Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 206010009900 Colitis ulcerative Diseases 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- 206010011086 Coronary artery occlusion Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- PMATZTZNYRCHOR-CGLBZJNRSA-N Cyclosporin A Chemical compound CC[C@@H]1NC(=O)[C@H]([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](C(C)C)NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C1=O PMATZTZNYRCHOR-CGLBZJNRSA-N 0.000 description 1
- 229930105110 Cyclosporin A Natural products 0.000 description 1
- 108010036949 Cyclosporine Proteins 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
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 206010012442 Dermatitis contact Diseases 0.000 description 1
- 206010060742 Endocrine ophthalmopathy Diseases 0.000 description 1
- 206010017943 Gastrointestinal conditions Diseases 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 206010018364 Glomerulonephritis Diseases 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 206010021143 Hypoxia Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010030216 Oesophagitis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000008469 Peptic Ulcer Diseases 0.000 description 1
- 229940123932 Phosphodiesterase 4 inhibitor Drugs 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 description 1
- 206010040070 Septic Shock Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 108091008874 T cell receptors Proteins 0.000 description 1
- 102000016266 T-Cell Antigen Receptors Human genes 0.000 description 1
- 206010052779 Transplant rejections Diseases 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 201000006704 Ulcerative Colitis Diseases 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 description 1
- 201000000028 adult respiratory distress syndrome Diseases 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000007953 anoxia Effects 0.000 description 1
- 229940124599 anti-inflammatory drug Drugs 0.000 description 1
- 230000001262 anti-secretory effect Effects 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- KFRAKQXWWCKHKF-UHFFFAOYSA-N azanium;dichloromethane;ethanol;hydroxide Chemical compound [NH4+].[OH-].CCO.ClCCl KFRAKQXWWCKHKF-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
- 230000008455 cerebrovascular function Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 208000010247 contact dermatitis Diseases 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 201000001981 dermatomyositis Diseases 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 230000000095 emetic effect Effects 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 208000006881 esophagitis Diseases 0.000 description 1
- DZGCGKFAPXFTNM-UHFFFAOYSA-N ethanol;hydron;chloride Chemical compound Cl.CCO DZGCGKFAPXFTNM-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 210000005003 heart tissue Anatomy 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 229960003444 immunosuppressant agent Drugs 0.000 description 1
- 230000001861 immunosuppressant effect Effects 0.000 description 1
- 229940125721 immunosuppressive agent Drugs 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 206010028417 myasthenia gravis Diseases 0.000 description 1
- 229920005615 natural polymer Polymers 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 125000001477 organic nitrogen group Chemical group 0.000 description 1
- 230000011164 ossification Effects 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- GIVUQTUKKWDKHE-UHFFFAOYSA-N pyrido[2,3-d]pyridazine Chemical compound C1=NN=CC2=CC=CN=C21 GIVUQTUKKWDKHE-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- ZAHRKKWIAAJSAO-UHFFFAOYSA-N rapamycin Natural products COCC(O)C(=C/C(C)C(=O)CC(OC(=O)C1CCCCN1C(=O)C(=O)C2(O)OC(CC(OC)C(=CC=CC=CC(C)CC(C)C(=O)C)C)CCC2C)C(C)CC3CCC(O)C(C3)OC)C ZAHRKKWIAAJSAO-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- HJORMJIFDVBMOB-UHFFFAOYSA-N rolipram Chemical compound COC1=CC=C(C2CC(=O)NC2)C=C1OC1CCCC1 HJORMJIFDVBMOB-UHFFFAOYSA-N 0.000 description 1
- 229950005741 rolipram Drugs 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 230000036303 septic shock Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- 208000017520 skin disease Diseases 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
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000002294 steroidal antiinflammatory agent Substances 0.000 description 1
- 230000003637 steroidlike Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000013268 sustained release Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 230000017423 tissue regeneration Effects 0.000 description 1
- 208000035408 type 1 diabetes mellitus 1 Diseases 0.000 description 1
- 230000001562 ulcerogenic effect Effects 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/14—Decongestants or antiallergics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Dermatology (AREA)
- Immunology (AREA)
- Cardiology (AREA)
- Biomedical Technology (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Ophthalmology & Optometry (AREA)
- Pain & Pain Management (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES009701670A ES2137113B1 (es) | 1997-07-29 | 1997-07-29 | Nuevos derivados de triazolo-piridazinas heterociclicos. |
| PCT/EP1998/004340 WO1999006404A1 (en) | 1997-07-29 | 1998-07-13 | 1,2,4-triazolo[4,3-b]pyrido[3,2-d]pyridazine derivatives and pharmaceutical compositions containing them |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20000394D0 NO20000394D0 (no) | 2000-01-26 |
| NO20000394L NO20000394L (no) | 2000-03-27 |
| NO315118B1 true NO315118B1 (no) | 2003-07-14 |
Family
ID=8300216
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20000394A NO315118B1 (no) | 1997-07-29 | 2000-01-26 | 1,2,4-triazolo[4,3-B]pyrido[3,2-D]pyridazinderivater samt farmasöytiske sammensetninger inneholdende slike |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US6407108B1 (bg) |
| EP (1) | EP1001955B1 (bg) |
| JP (1) | JP4320118B2 (bg) |
| KR (1) | KR20010022353A (bg) |
| CN (1) | CN1135231C (bg) |
| AR (1) | AR015927A1 (bg) |
| AT (1) | ATE207069T1 (bg) |
| AU (1) | AU737709B2 (bg) |
| BG (1) | BG64448B1 (bg) |
| BR (1) | BR9810829B1 (bg) |
| CA (1) | CA2298935A1 (bg) |
| CO (1) | CO4970780A1 (bg) |
| CZ (1) | CZ290208B6 (bg) |
| DE (1) | DE69802100T2 (bg) |
| DK (1) | DK1001955T3 (bg) |
| EE (1) | EE04313B1 (bg) |
| EG (1) | EG24041A (bg) |
| ES (2) | ES2137113B1 (bg) |
| HK (1) | HK1024914A1 (bg) |
| HU (1) | HUP0004708A3 (bg) |
| ID (1) | ID24506A (bg) |
| IL (1) | IL134081A (bg) |
| MY (1) | MY118796A (bg) |
| NO (1) | NO315118B1 (bg) |
| NZ (1) | NZ502356A (bg) |
| PE (1) | PE111099A1 (bg) |
| PL (1) | PL191031B1 (bg) |
| PT (1) | PT1001955E (bg) |
| RU (1) | RU2202552C2 (bg) |
| SI (1) | SI1001955T1 (bg) |
| SK (1) | SK284046B6 (bg) |
| TR (1) | TR200000243T2 (bg) |
| TW (1) | TW542837B (bg) |
| UA (1) | UA60339C2 (bg) |
| WO (1) | WO1999006404A1 (bg) |
| ZA (1) | ZA986248B (bg) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2792938B1 (fr) * | 1999-04-28 | 2001-07-06 | Warner Lambert Co | NOUVELLES 1-AMINO TRIAZOLO [4,3-a] QUINAZOLINE-5-ONES INHIBITRICES DE PHOSPHODIESTERASES IV |
| MXPA02001830A (es) | 1999-08-21 | 2002-08-12 | Byk Gulden Lomberg Chem Fab | Combinacion sinergica de inhibidores de pde y agonista de beta 2 adrenoceptor. |
| WO2002080974A1 (fr) * | 2001-04-04 | 2002-10-17 | Sankyo Company, Limited | Utilisation medicale d'inhibiteur de production de cytokine |
| ES2282469T3 (es) | 2001-09-19 | 2007-10-16 | Nycomed Gmbh | Combinacion de un nsaid y un inhibidor de pde-4. |
| FR2832711B1 (fr) * | 2001-11-26 | 2004-01-30 | Warner Lambert Co | Derives de triazolo [4,3-a] pyrido [2,3-d] pyrimidin-5-ones, compositions les contenant, procede de preparation et utilisation |
| CN100572381C (zh) * | 2002-11-06 | 2009-12-23 | Aska制药株式会社 | 吡唑并二氮杂萘衍生物 |
| ES2211344B1 (es) | 2002-12-26 | 2005-10-01 | Almirall Prodesfarma, S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| US20050187278A1 (en) * | 2003-08-28 | 2005-08-25 | Pharmacia Corporation | Treatment or prevention of vascular disorders with Cox-2 inhibitors in combination with cyclic AMP-specific phosphodiesterase inhibitors |
| RU2246496C1 (ru) * | 2003-09-12 | 2005-02-20 | Тец Виктор Вениаминович | Вещество с противовирусной и антибактериальной активностью на основе производных 2,8-дитиоксо-1h-пирано[2,3-d, 6,5-d`] дипиримидина и их 10-аза-аналогов |
| ES2251866B1 (es) | 2004-06-18 | 2007-06-16 | Laboratorios Almirall S.A. | Nuevos derivados de piridazin-3(2h)-ona. |
| KR100959771B1 (ko) * | 2005-06-10 | 2010-05-28 | 머크 샤프 앤드 돔 코포레이션 | Ａｋｔ 활성의 억제제 |
| EP2258358A3 (en) | 2005-08-26 | 2011-09-07 | Braincells, Inc. | Neurogenesis with acetylcholinesterase inhibitor |
| CA2620333A1 (en) | 2005-08-26 | 2007-03-01 | Braincells, Inc. | Neurogenesis by muscarinic receptor modulation |
| EP1925617B1 (en) * | 2005-09-15 | 2012-11-14 | ASKA Pharmaceutical Co., Ltd. | Heterocyclic compound, and production process and use thereof |
| EP1940389A2 (en) | 2005-10-21 | 2008-07-09 | Braincells, Inc. | Modulation of neurogenesis by pde inhibition |
| WO2007053596A1 (en) | 2005-10-31 | 2007-05-10 | Braincells, Inc. | Gaba receptor mediated modulation of neurogenesis |
| US20100216734A1 (en) | 2006-03-08 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis by nootropic agents |
| CA2651813A1 (en) | 2006-05-09 | 2007-11-22 | Braincells, Inc. | Neurogenesis by modulating angiotensin |
| EP2026813A2 (en) | 2006-05-09 | 2009-02-25 | Braincells, Inc. | 5 ht receptor mediated neurogenesis |
| EP2057164A1 (en) | 2006-08-07 | 2009-05-13 | Incyte Corporation | Triazolotriazines as kinase inhibitors |
| EP2068872A1 (en) | 2006-09-08 | 2009-06-17 | Braincells, Inc. | Combinations containing a 4-acylaminopyridine derivative |
| US20100184806A1 (en) | 2006-09-19 | 2010-07-22 | Braincells, Inc. | Modulation of neurogenesis by ppar agents |
| HUE026659T2 (en) | 2006-11-22 | 2016-07-28 | Incyte Holdings Corp | Imidazotriazines and imidazopyrimidines as kinase inhibitors |
| WO2009089027A1 (en) * | 2008-01-09 | 2009-07-16 | Government Of The United States Of America As Represented By The Secretary Of The Department Of Health And Human Service, National Institutes Of Health | Phosphodiesterase inhibitors |
| EP2300455B1 (en) | 2008-05-21 | 2017-07-19 | Incyte Holdings Corporation | Salts of 2-fluoro-n-methyl-4-[7-(quinolin-6-yl-methyl)- imidazo[1,2-b][1,2,4]triazin-2-yl]benzamide and processes related to preparing the same |
| EP2196465A1 (en) | 2008-12-15 | 2010-06-16 | Almirall, S.A. | (3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors |
| US20100216805A1 (en) | 2009-02-25 | 2010-08-26 | Braincells, Inc. | Modulation of neurogenesis using d-cycloserine combinations |
| EP2226323A1 (en) | 2009-02-27 | 2010-09-08 | Almirall, S.A. | New tetrahydropyrazolo[3,4-c]isoquinolin-5-amine derivatives |
| NZ601033A (en) | 2009-12-31 | 2014-02-28 | Ct Nac Investigaciones Oncologicas Cnio | Tricyclic compounds for use as kinase inhibitors |
| CA2788398C (en) | 2010-02-03 | 2018-02-27 | Incyte Corporation | Imidazo[1,2-b][1,2,4]triazines as c-met inhibitors |
| EP2380890A1 (en) | 2010-04-23 | 2011-10-26 | Almirall, S.A. | New 7,8-dihydro-1,6-naphthyridin-5(6h)-one-derivatives as PDE4 inhibitors |
| EP2394998A1 (en) | 2010-05-31 | 2011-12-14 | Almirall, S.A. | 3-(5-Amino-6-oxo-1,6-dihydropyridazin-3-yl)-biphenyl derivatives as PDE4 inhibitors |
| WO2012098387A1 (en) | 2011-01-18 | 2012-07-26 | Centro Nacional De Investigaciones Oncológicas (Cnio) | 6, 7-ring-fused triazolo [4, 3 - b] pyridazine derivatives as pim inhibitors |
| WO2013005041A1 (en) | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncológicas (Cnio) | Tricyclic heterocyclic compounds as kinase inhibitors |
| WO2013004984A1 (en) | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncologicas (Cnio) | Tricyclic compounds for use as kinase inhibitors |
| WO2013005057A1 (en) | 2011-07-07 | 2013-01-10 | Centro Nacional De Investigaciones Oncológicas (Cnio) | New compounds |
| WO2013106547A1 (en) | 2012-01-10 | 2013-07-18 | President And Fellows Of Harvard College | Beta-cell replication promoting compounds and methods of their use |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3122670A1 (de) | 1981-06-06 | 1982-12-23 | Dr. Karl Thomae Gmbh, 7950 Biberach | "neue 1,4,9,10-tetrahydro-pyrazolo(4,3-e) pyrido(3,2-b)(1,4)diazepin-10-one, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von pharmazeutischen wirkstoffen" |
| PH21834A (en) * | 1982-01-18 | 1988-03-17 | Lepetit Spa | New 6-substituted-s-triazolo(3,4-a)phthalazine derivatives |
| JP3120857B2 (ja) * | 1990-02-19 | 2000-12-25 | 中外製薬株式会社 | 新規な縮合複素環化合物とこれを用いた抗喘息剤 |
| WO1993007146A1 (en) * | 1991-10-09 | 1993-04-15 | Syntex (U.S.A.) Inc. | Benzo and pyrido pyridazinone and pyridazinthione compounds with pde iv inhibiting activity |
| GB9514465D0 (en) | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
-
1997
- 1997-07-29 ES ES009701670A patent/ES2137113B1/es not_active Expired - Lifetime
-
1998
- 1998-07-13 CZ CZ2000333A patent/CZ290208B6/cs not_active IP Right Cessation
- 1998-07-13 ID IDW20000180A patent/ID24506A/id unknown
- 1998-07-13 PL PL338214A patent/PL191031B1/pl not_active IP Right Cessation
- 1998-07-13 WO PCT/EP1998/004340 patent/WO1999006404A1/en not_active Application Discontinuation
- 1998-07-13 AU AU88612/98A patent/AU737709B2/en not_active Ceased
- 1998-07-13 SI SI9830042T patent/SI1001955T1/xx unknown
- 1998-07-13 SK SK86-2000A patent/SK284046B6/sk not_active IP Right Cessation
- 1998-07-13 RU RU2000104863/04A patent/RU2202552C2/ru not_active IP Right Cessation
- 1998-07-13 DK DK98940218T patent/DK1001955T3/da active
- 1998-07-13 CA CA002298935A patent/CA2298935A1/en not_active Abandoned
- 1998-07-13 NZ NZ502356A patent/NZ502356A/xx unknown
- 1998-07-13 IL IL13408198A patent/IL134081A/en active IP Right Grant
- 1998-07-13 CN CNB988081210A patent/CN1135231C/zh not_active Expired - Fee Related
- 1998-07-13 TR TR2000/00243T patent/TR200000243T2/xx unknown
- 1998-07-13 BR BRPI9810829-8A patent/BR9810829B1/pt not_active IP Right Cessation
- 1998-07-13 PT PT78400158T patent/PT1001955E/pt unknown
- 1998-07-13 EP EP98940218A patent/EP1001955B1/en not_active Expired - Lifetime
- 1998-07-13 AT AT98940218T patent/ATE207069T1/de not_active IP Right Cessation
- 1998-07-13 KR KR1020007000932A patent/KR20010022353A/ko not_active Application Discontinuation
- 1998-07-13 DE DE69802100T patent/DE69802100T2/de not_active Expired - Fee Related
- 1998-07-13 JP JP2000505162A patent/JP4320118B2/ja not_active Expired - Fee Related
- 1998-07-13 UA UA2000010486A patent/UA60339C2/uk unknown
- 1998-07-13 ES ES98940218T patent/ES2162466T3/es not_active Expired - Lifetime
- 1998-07-13 HU HU0004708A patent/HUP0004708A3/hu unknown
- 1998-07-13 EE EEP200000052A patent/EE04313B1/xx not_active IP Right Cessation
- 1998-07-14 ZA ZA986248A patent/ZA986248B/xx unknown
- 1998-07-16 TW TW087111560A patent/TW542837B/zh not_active IP Right Cessation
- 1998-07-27 MY MYPI98003421A patent/MY118796A/en unknown
- 1998-07-28 CO CO98042905A patent/CO4970780A1/es unknown
- 1998-07-29 AR ARP980103719A patent/AR015927A1/es active IP Right Grant
- 1998-07-29 EG EG88998A patent/EG24041A/xx active
- 1998-07-30 PE PE1998000682A patent/PE111099A1/es not_active Application Discontinuation
-
2000
- 2000-01-26 NO NO20000394A patent/NO315118B1/no not_active IP Right Cessation
- 2000-01-27 BG BG104112A patent/BG64448B1/bg unknown
- 2000-01-28 US US09/496,019 patent/US6407108B1/en not_active Expired - Fee Related
- 2000-06-15 HK HK00103595A patent/HK1024914A1/xx not_active IP Right Cessation
-
2002
- 2002-01-08 US US10/038,777 patent/US20020183326A1/en not_active Abandoned
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| NO315118B1 (no) | 1,2,4-triazolo[4,3-B]pyrido[3,2-D]pyridazinderivater samt farmasöytiske sammensetninger inneholdende slike | |
| CA2557541C (en) | Pyrimidine derivatives | |
| TW378210B (en) | Tetracyclic derivatives; process of preparation and use | |
| TW406082B (en) | Pyridazino quinoline compounds | |
| CZ224195A3 (en) | The use of pyrrolopyridine derivatives for preparing pharmaceutical preparations | |
| MX2008001020A (es) | Un monohidrato de pirrolo[1-2-b]pirazol piridin quinolin substituido como inhibidor de factor de crecimiento de transformacion-beta (tgf-beta). | |
| JP2008523070A (ja) | バニロイド受容体サブタイプ１（ｖｒ１）に対する拮抗薬およびこの使用 | |
| AU4564500A (en) | 4,5,6,7-tetrahydroindazole derivatives as antitumor agents | |
| CA2934553A1 (en) | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment | |
| JPH03215489A (ja) | Ｐａｆ拮抗作用を有する新規ヘトラゼピン、その製造方法及び該ヘトラゼピンを含有する医薬組成物 | |
| CN106456653A (zh) | 高胰岛素血症相关病症的治疗 | |
| JPH0412269B2 (bg) | ||
| WO2014043246A1 (en) | Enoyl reductase inhibitors with antibacterial activity | |
| CA2990004A1 (en) | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment | |
| MX2007006172A (es) | Nuevos derivados de piridotienopirimidina. | |
| IL126206A (en) | History 2 - (3H) - Oxazolone and their use as COX-2 enzyme inhibitors, processes for their preparation and pharmaceutical preparations containing them | |
| WO1995007893A1 (en) | Fused tricyclic heteroaromatic derivatives as dopamine receptor subtype ligands | |
| CZ265498A3 (cs) | Triazolové deriváty, způsob jejich výroby a farmaceutický prostředek s jejich obsahem | |
| NO136251B (bg) | ||
| TW201120048A (en) | Azabicyclo[2.2.1]heptane compounds as alpha-7 nicotinic acetylcholine receptor ligands | |
| JP2009502832A (ja) | 新規ピリド［３’，２’：４，５］フロ［３，２−ｄ］ピリミジン誘導体 | |
| CN116283993B (zh) | 一种嘧啶类化合物及其制备方法和应用 | |
| MXPA00000910A (en) | 1,2,4-triazolo[4,3-b]pyrido[3,2-d]pyridazine derivatives and pharmaceutical compositions containing them | |
| BRPI0903803B1 (pt) | Composto, processo de preparação, composição farmacêutica e uso dos compostos | |
| TWI325322B (en) | Substituted 2-pyrimidinyl-6,7,8,9-tetrahydropyrimido[1,2-a] pyrimidin-4-one; and 7-pyrimidiny-2,3-dihydroimidazo[1,2-a] pyrimidin-5(1h)one derivatives |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM1K | Lapsed by not paying the annual fees |