IL134081A - History - 6 Aril 1, 2, 4 - Triazolo b] - 3, 4] Pyrido d] -2, 3] Pyridazine, their preparation and pharmaceutical preparations containing them - Google Patents

History - 6 Aril 1, 2, 4 - Triazolo b] - 3, 4] Pyrido d] -2, 3] Pyridazine, their preparation and pharmaceutical preparations containing them

Info

Publication number: IL134081A
Authority: IL; Israel
Prior art keywords: group; pyrido; compound according; pyridazine; triazolo
Prior art date: 1997-07-29

Application number

IL13408198A

Other languages

English (en)

Hebrew (he)

Other versions

IL134081A0 (en

Original Assignee

Almirall Prodesfarma Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-07-29

Filing date

1998-07-13

Publication date

2004-02-08

1998-07-13 Application filed by Almirall Prodesfarma Sa filed Critical Almirall Prodesfarma Sa

2001-04-30 Publication of IL134081A0 publication Critical patent/IL134081A0/xx

2004-02-08 Publication of IL134081A publication Critical patent/IL134081A/en

Links

238000002360 preparation method Methods 0.000 title claims description 7
GIVUQTUKKWDKHE-UHFFFAOYSA-N pyrido[2,3-d]pyridazine Chemical class C1=NN=CC2=CC=CN=C21 GIVUQTUKKWDKHE-UHFFFAOYSA-N 0.000 title claims description 5
239000008194 pharmaceutical composition Substances 0.000 title description 5
150000001875 compounds Chemical class 0.000 claims abstract description 43
125000000217 alkyl group Chemical group 0.000 claims abstract description 16
125000003118 aryl group Chemical group 0.000 claims abstract description 12
-1 methylenedioxy Chemical group 0.000 claims abstract description 12
125000005843 halogen group Chemical group 0.000 claims abstract description 10
125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 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 abstract description 5
102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims abstract description 5
108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
239000001257 hydrogen Substances 0.000 claims abstract description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims abstract description 3
239000000203 mixture Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 13
239000003085 diluting agent Substances 0.000 claims description 6
239000003814 drug Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 5
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
208000025865 Ulcer Diseases 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
231100000397 ulcer Toxicity 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 3
208000026935 allergic disease Diseases 0.000 claims description 3
208000026278 immune system disease Diseases 0.000 claims description 3
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
229910052801 chlorine Inorganic materials 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
125000001624 naphthyl group Chemical group 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
125000001544 thienyl group Chemical group 0.000 claims description 2
206010020751 Hypersensitivity Diseases 0.000 claims 2
206010061218 Inflammation Diseases 0.000 claims 2
208000030961 allergic reaction Diseases 0.000 claims 2
230000004054 inflammatory process Effects 0.000 claims 2
125000004169 (C1-C6) alkyl 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
DIAJZQVKZBSZCG-UHFFFAOYSA-N C1=CN=C2C=NN3C=NN=C3C2=C1 Chemical group C1=CN=C2C=NN3C=NN=C3C2=C1 DIAJZQVKZBSZCG-UHFFFAOYSA-N 0.000 claims 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
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 1
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 1
230000015572 biosynthetic process Effects 0.000 claims 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 1
125000001188 haloalkyl group Chemical group 0.000 abstract description 3
125000004429 atom Chemical group 0.000 abstract 1
230000002401 inhibitory effect Effects 0.000 abstract 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 9
239000000725 suspension Substances 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000007787 solid Substances 0.000 description 8
150000002391 heterocyclic compounds Chemical class 0.000 description 7
RFONJRMUUALMBA-UHFFFAOYSA-N 2-methanidylpropane Chemical compound CC(C)[CH2-] RFONJRMUUALMBA-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-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
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
239000000243 solution Substances 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
239000002775 capsule 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
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
239000002253 acid Substances 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000008901 benefit Effects 0.000 description 3
201000010099 disease Diseases 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
238000010992 reflux Methods 0.000 description 3
239000003826 tablet Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
101100296719 Caenorhabditis elegans pde-4 gene Proteins 0.000 description 2
206010012438 Dermatitis atopic Diseases 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
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
230000000903 blocking effect Effects 0.000 description 2
238000009835 boiling Methods 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
238000009109 curative therapy Methods 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000012530 fluid Substances 0.000 description 2
230000002496 gastric effect Effects 0.000 description 2
125000000623 heterocyclic group Chemical group 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
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
239000012047 saturated solution Substances 0.000 description 2
150000003431 steroids Chemical class 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
ZQWUKMQRYDIOPF-UHFFFAOYSA-N (8-phenylpyrido[2,3-d]pyridazin-5-yl)hydrazine;dihydrochloride Chemical compound Cl.Cl.C12=NC=CC=C2C(NN)=NN=C1C1=CC=CC=C1 ZQWUKMQRYDIOPF-UHFFFAOYSA-N 0.000 description 1
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
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
125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 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
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
DBXFFMDFQSNXQG-UHFFFAOYSA-N C1=CC=C(C=C1)C2=C3C(=CN=N2)C=CC=N3 Chemical compound C1=CC=C(C=C1)C2=C3C(=CN=N2)C=CC=N3 DBXFFMDFQSNXQG-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
206010009900 Colitis ulcerative Diseases 0.000 description 1
229940126062 Compound A Drugs 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
206010011086 Coronary artery occlusion Diseases 0.000 description 1
208000011231 Crohn disease Diseases 0.000 description 1
229930105110 Cyclosporin A Natural products 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
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
239000004150 EU approved colour Substances 0.000 description 1
208000018522 Gastrointestinal disease Diseases 0.000 description 1
239000001828 Gelatine Substances 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
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
206010038687 Respiratory distress 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
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
PRXRUNOAOLTIEF-ADSICKODSA-N Sorbitan trioleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](OC(=O)CCCCCCC\C=C/CCCCCCCC)[C@H]1OC[C@H](O)[C@H]1OC(=O)CCCCCCC\C=C/CCCCCCCC PRXRUNOAOLTIEF-ADSICKODSA-N 0.000 description 1
239000004147 Sorbitan trioleate Substances 0.000 description 1
229920002472 Starch Polymers 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
108700012920 TNF Proteins 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
239000000443 aerosol Substances 0.000 description 1
125000003342 alkenyl 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
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 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
239000007864 aqueous solution Substances 0.000 description 1
208000010668 atopic eczema Diseases 0.000 description 1
KFRAKQXWWCKHKF-UHFFFAOYSA-N azanium;dichloromethane;ethanol;hydroxide Chemical compound [NH4+].[OH-].CCO.ClCCl KFRAKQXWWCKHKF-UHFFFAOYSA-N 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
125000005605 benzo group Chemical group 0.000 description 1
XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 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
125000004432 carbon atom Chemical group C* 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
230000008455 cerebrovascular function Effects 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229960001265 ciclosporin Drugs 0.000 description 1
238000004040 coloring Methods 0.000 description 1
208000010247 contact dermatitis Diseases 0.000 description 1
239000008120 corn starch Substances 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
208000035475 disorder Diseases 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
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
238000009472 formulation Methods 0.000 description 1
208000021302 gastroesophageal reflux disease Diseases 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 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
125000001183 hydrocarbyl group Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
229960003444 immunosuppressant agent Drugs 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
OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
239000002664 nootropic agent Substances 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
210000000056 organ Anatomy 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
230000007170 pathology 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
LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
WCKGRSPYFFVKQT-UHFFFAOYSA-N pyridazine;dihydrochloride Chemical compound Cl.Cl.C1=CC=NN=C1 WCKGRSPYFFVKQT-UHFFFAOYSA-N 0.000 description 1
150000004892 pyridazines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 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
230000009467 reduction Effects 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229950005741 rolipram Drugs 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
229910052708 sodium Inorganic materials 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
235000019337 sorbitan trioleate Nutrition 0.000 description 1
229960000391 sorbitan trioleate Drugs 0.000 description 1
239000000600 sorbitol 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
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
208000011580 syndromic disease Diseases 0.000 description 1
229920001059 synthetic polymer Polymers 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
230000017423 tissue regeneration Effects 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect 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)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pulmonology (AREA)
Immunology (AREA)
Dermatology (AREA)
Ophthalmology & Optometry (AREA)
Rheumatology (AREA)
Hematology (AREA)
Obesity (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Diabetes (AREA)
Cardiology (AREA)
Neurosurgery (AREA)
Heart & Thoracic Surgery (AREA)
Pain & Pain Management (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

IL13408198A 1997-07-29 1998-07-13 History - 6 Aril 1, 2, 4 - Triazolo b] - 3, 4] Pyrido d] -2, 3] Pyridazine, their preparation and pharmaceutical preparations containing them IL134081A (en)

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 (2)

Publication Number	Publication Date
IL134081A0 IL134081A0 (en)	2001-04-30
IL134081A true IL134081A (en)	2004-02-08

Family

ID=8300216

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL13408198A IL134081A (en)	1997-07-29	1998-07-13	History - 6 Aril 1, 2, 4 - Triazolo b] - 3, 4] Pyrido d] -2, 3] Pyridazine, their preparation and pharmaceutical preparations containing them

Country Status (35)

Country	Link
US (2)	US6407108B1 (pl)
EP (1)	EP1001955B1 (pl)
JP (1)	JP4320118B2 (pl)
KR (1)	KR20010022353A (pl)
CN (1)	CN1135231C (pl)
AR (1)	AR015927A1 (pl)
AT (1)	ATE207069T1 (pl)
AU (1)	AU737709B2 (pl)
BG (1)	BG64448B1 (pl)
BR (1)	BR9810829B1 (pl)
CA (1)	CA2298935A1 (pl)
CO (1)	CO4970780A1 (pl)
CZ (1)	CZ290208B6 (pl)
DE (1)	DE69802100T2 (pl)
DK (1)	DK1001955T3 (pl)
EE (1)	EE04313B1 (pl)
EG (1)	EG24041A (pl)
ES (2)	ES2137113B1 (pl)
HU (1)	HUP0004708A3 (pl)
ID (1)	ID24506A (pl)
IL (1)	IL134081A (pl)
MY (1)	MY118796A (pl)
NO (1)	NO315118B1 (pl)
NZ (1)	NZ502356A (pl)
PE (1)	PE111099A1 (pl)
PL (1)	PL191031B1 (pl)
PT (1)	PT1001955E (pl)
RU (1)	RU2202552C2 (pl)
SI (1)	SI1001955T1 (pl)
SK (1)	SK284046B6 (pl)
TR (1)	TR200000243T2 (pl)
TW (1)	TW542837B (pl)
UA (1)	UA60339C2 (pl)
WO (1)	WO1999006404A1 (pl)
ZA (1)	ZA986248B (pl)

Families Citing this family (38)

* Cited by examiner, † Cited by third party
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
CA2715683A1 (en)	1999-08-21	2001-03-01	Nycomed Gmbh	Synergistic combination
WO2002080974A1 (en) *	2001-04-04	2002-10-17	Sankyo Company, Limited	Novel medicinal use of cytokine production inhibitor
MXPA04002562A (es) *	2001-09-19	2004-05-31	Altana Pharma Ag	Combinacion de un pde-4 y nsaid.
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
US7608716B2 (en)	2002-11-06	2009-10-27	Aska Pharmaceutical Co., Ltd.	Pyrazolonaphthyridine derivative
ES2211344B1 (es)	2002-12-26	2005-10-01	Almirall Prodesfarma, S.A.	Nuevos derivados de piridazin-3(2h)-ona.
EA200501548A1 (ru)	2003-04-01	2006-02-24	Апплайд Резеч Системз Арс Холдинг Н.В.	Ингибиторы фосфодиэстераз при бесплодии
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.
AU2006258124B8 (en) *	2005-06-10	2010-01-07	Merck Sharp & Dohme Corp.	Inhibitors of Akt activity
EP2258359A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009506069A (ja)	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
CN101268073B (zh) *	2005-09-15	2011-10-19	Aska制药株式会社	杂环化合物、制备方法及其用途
US7985756B2 (en)	2005-10-21	2011-07-26	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
WO2007134136A2 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
WO2007134077A2 (en)	2006-05-09	2007-11-22	Braincells, Inc.	5 ht receptor mediated neurogenesis
JP2010500365A (ja)	2006-08-07	2010-01-07	インサイト・コーポレイション	キナーゼ阻害剤としてのトリアゾロトリアジン
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
ES2560435T3 (es)	2006-11-22	2016-02-19	Incyte Holdings Corporation	Imidazotriazinas e imidazopirimidinas como inhibidores de la quinasa
US20110112079A1 (en) *	2008-01-09	2011-05-12	Thomas Craig J	Phosphodiesterase inhibitors
MX393622B (es)	2008-05-21	2025-03-24	Incyte Corp	Sales de 2-fluoro-n-metil-4-[7-(quinolin-6-il-metil)-imidazo[1,2-b][1,2,4]triazin-2-il]benzamida y procesos relacionados con la preparacion de las mismas.
EP2196465A1 (en)	2008-12-15	2010-06-16	Almirall, S.A.	(3-oxo)pyridazin-4-ylurea derivatives as PDE4 inhibitors
WO2010099217A1 (en)	2009-02-25	2010-09-02	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
PH12012501361A1 (en)	2009-12-31	2012-10-22	Centro Nac De Investigaciones Oncologicas Cnio	Tricyclic compounds for use as kinase inhibitors
JP5714030B2 (ja)	2010-02-03	2015-05-07	インサイトコーポレーションＩｎｃｙｔｅＣｏｒｐｏｒａｔｉｏｎ	Ｃ−Ｍｅｔ阻害剤としてのイミダゾ［１，２−ｂ］［１，２，４］トリアジン
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
WO2013005057A1 (en)	2011-07-07	2013-01-10	Centro Nacional De Investigaciones Oncológicas (Cnio)	New compounds
WO2013004984A1 (en)	2011-07-07	2013-01-10	Centro Nacional De Investigaciones Oncologicas (Cnio)	Tricyclic compounds for use as kinase inhibitors
WO2013005041A1 (en)	2011-07-07	2013-01-10	Centro Nacional De Investigaciones Oncológicas (Cnio)	Tricyclic heterocyclic compounds as kinase inhibitors
EP2804603A1 (en)	2012-01-10	2014-11-26	President and Fellows of Harvard College	Beta-cell replication promoting compounds and methods of their use

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
DE3677445D1 (de) *	1985-09-30	1991-03-14	Ciba Geigy Ag	2-substituierte-e-kondensierte(1,5-c)-pyrimidine, pharmazeutische zubereitungen und ihre verwendung.
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
JP3245165B2 (ja) *	1991-10-09	2002-01-07	シンテックス（ユー・エス・エイ）・インコーポレイテッド	ピリドピリダジノンおよびピリダジンチオン化合物
GB9514465D0 (en)	1995-07-14	1995-09-13	Glaxo Lab Sa	Chemical compounds
DE19510965A1 (de) *	1995-03-24	1996-09-26	Asta Medica Ag	Neue Pyrido/3,2-e/pyrazinone mit antiasthmatischer Wirksamkeit und Verfahren zu deren Herstellung

1997
- 1997-07-29 ES ES009701670A patent/ES2137113B1/es not_active Expired - Lifetime
1998
- 1998-07-13 DK DK98940218T patent/DK1001955T3/da active
- 1998-07-13 ES ES98940218T patent/ES2162466T3/es not_active Expired - Lifetime
- 1998-07-13 CZ CZ2000333A patent/CZ290208B6/cs not_active IP Right Cessation
- 1998-07-13 EP EP98940218A patent/EP1001955B1/en not_active Expired - Lifetime
- 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 PL PL338214A patent/PL191031B1/pl not_active IP Right Cessation
- 1998-07-13 UA UA2000010486A patent/UA60339C2/uk unknown
- 1998-07-13 CN CNB988081210A patent/CN1135231C/zh not_active Expired - Fee Related
- 1998-07-13 JP JP2000505162A patent/JP4320118B2/ja not_active Expired - Fee Related
- 1998-07-13 NZ NZ502356A patent/NZ502356A/xx unknown
- 1998-07-13 HU HU0004708A patent/HUP0004708A3/hu unknown
- 1998-07-13 ID IDW20000180A patent/ID24506A/id unknown
- 1998-07-13 SI SI9830042T patent/SI1001955T1/xx unknown
- 1998-07-13 EE EEP200000052A patent/EE04313B1/xx not_active IP Right Cessation
- 1998-07-13 TR TR2000/00243T patent/TR200000243T2/xx unknown
- 1998-07-13 CA CA002298935A patent/CA2298935A1/en not_active Abandoned
- 1998-07-13 KR KR1020007000932A patent/KR20010022353A/ko not_active Ceased
- 1998-07-13 BR BRPI9810829-8A patent/BR9810829B1/pt not_active IP Right Cessation
- 1998-07-13 DE DE69802100T patent/DE69802100T2/de not_active Expired - Fee Related
- 1998-07-13 IL IL13408198A patent/IL134081A/en active IP Right Grant
- 1998-07-13 AT AT98940218T patent/ATE207069T1/de not_active IP Right Cessation
- 1998-07-13 AU AU88612/98A patent/AU737709B2/en not_active Ceased
- 1998-07-13 WO PCT/EP1998/004340 patent/WO1999006404A1/en not_active Ceased
- 1998-07-13 PT PT78400158T patent/PT1001955E/pt unknown
- 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 EG EG88998A patent/EG24041A/xx active
- 1998-07-29 AR ARP980103719A patent/AR015927A1/es active IP Right Grant
- 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
2002
- 2002-01-08 US US10/038,777 patent/US20020183326A1/en not_active Abandoned

Also Published As

Publication number	Publication date
EP1001955B1 (en)	2001-10-17
CN1266434A (zh)	2000-09-13
BR9810829B1 (pt)	2009-08-11
ES2137113A1 (es)	1999-12-01
DE69802100D1 (de)	2001-11-22
PL338214A1 (en)	2000-10-09
BG104112A (en)	2001-01-31
CZ2000333A3 (cs)	2000-05-17
UA60339C2 (uk)	2003-10-15
AR015927A1 (es)	2001-05-30
CZ290208B6 (cs)	2002-06-12
TR200000243T2 (tr)	2000-07-21
NO20000394D0 (no)	2000-01-26
HUP0004708A2 (hu)	2001-07-30
CN1135231C (zh)	2004-01-21
US20020183326A1 (en)	2002-12-05
ATE207069T1 (de)	2001-11-15
SI1001955T1 (en)	2002-02-28
CO4970780A1 (es)	2000-11-07
EP1001955A1 (en)	2000-05-24
NO315118B1 (no)	2003-07-14
MY118796A (en)	2005-01-31
BG64448B1 (en)	2005-02-28
US6407108B1 (en)	2002-06-18
WO1999006404A1 (en)	1999-02-11
NZ502356A (en)	2001-03-30
PE111099A1 (es)	1999-11-18
SK862000A3 (en)	2000-07-11
EG24041A (en)	2008-04-03
ZA986248B (en)	1999-02-05
CA2298935A1 (en)	1999-02-11
EE200000052A (et)	2000-10-16
NO20000394L (no)	2000-03-27
DK1001955T3 (da)	2001-11-19
HUP0004708A3 (en)	2002-11-28
JP2001512121A (ja)	2001-08-21
ES2162466T3 (es)	2001-12-16
BR9810829A (pt)	2000-07-25
IL134081A0 (en)	2001-04-30
HK1024914A1 (en)	2000-10-27
JP4320118B2 (ja)	2009-08-26
AU8861298A (en)	1999-02-22
PT1001955E (pt)	2002-02-28
DE69802100T2 (de)	2002-03-14
KR20010022353A (ko)	2001-03-15
SK284046B6 (sk)	2004-08-03
RU2202552C2 (ru)	2003-04-20
PL191031B1 (pl)	2006-03-31
EE04313B1 (et)	2004-06-15
ES2137113B1 (es)	2000-09-16
TW542837B (en)	2003-07-21
ID24506A (id)	2000-07-20
AU737709B2 (en)	2001-08-30

Legal Events

Date	Code	Title	Description
2004-06-20	FF	Patent granted
2004-07-25	KB	Patent renewed

Publication	Publication Date	Title
AU737709B2 (en)	2001-08-30	1,2,4-triazolo{4,3-b}pyrido{3,2-d}pyridazine derivatives and pharmaceutical compositions containing them
CA2339630C (en)	2006-05-23	Carboline derivatives as cgmp phosphodiesterase inhibitors
AU702548B2 (en)	1999-02-25	Chemical compounds
CZ211696A3 (en)	1997-06-11	Tetracyclic derivatives, processes of their preparation, their use and pharmaceutical compositions containing thereof
MXPA02012895A (es)	2003-05-14	Derivados de pirazol condensado con 1-(heteroaril-fenil) como inhibidores del factor xa.
IL142959A (en)	2010-05-31	Nitrogen containing heterobicycles and pharmaceutical compositions comprising same
CA2660318A1 (en)	2008-02-21	Modulators of glucocorticoid receptor, ap-1, and/or nf-kb activit y and use thereof
EP0640606A1 (en)	1995-03-01	Thienopyrimidine derivatives, their production and use
WO2009100536A1 (en)	2009-08-20	Inhibitors of kinase activity with 1,2-di-cyclyl substituted alkyne structures
CA2557785A1 (en)	2005-10-06	Hiv integrase inhibitors
CZ265498A3 (cs)	1998-12-16	Triazolové deriváty, způsob jejich výroby a farmaceutický prostředek s jejich obsahem
JP2004513128A (ja)	2004-04-30	Ｐｄｅ５阻害剤としてのインドール誘導体
MX2007006172A (es)	2007-07-13	Nuevos derivados de piridotienopirimidina.
HK1024914B (en)	2002-02-22	1,2,4-triazolo 4,3-b]pyrido 3,2-d]pyridazine derivatives and pharmaceutical compositions containing them
MXPA00000910A (en)	2002-03-05	1,2,4-triazolo[4,3-b]pyrido[3,2-d]pyridazine derivatives and pharmaceutical compositions containing them
RU2682678C1 (ru)	2019-03-20	Способ получения диспироиндолинонов
RU2730286C1 (ru)	2020-08-21	Диспироиндолиноны на основе роданинов как ингибиторы р53-mdm2 белок-белкового взаимодействия
US20080221096A1 (en)	2008-09-11	Pyrido[3' ,2':4,5]Furo[3,2-d]Pyrimidine Derivatives
WO2025252117A1 (zh)	2025-12-11	选择性cdk抑制剂化合物及其应用
JPH02290878A (ja)	1990-11-30	ベンゾチエノ（フロ）ピリジン誘導体