IL97289A - 8-(hetero) aryl-3h 6h-1 4 5a 8-tetraazaacenaphthylene-3,5(4h)-dione derivatives pharmaceutical compositions containing them and processes for their preparation - Google Patents
8-(hetero) aryl-3h 6h-1 4 5a 8-tetraazaacenaphthylene-3,5(4h)-dione derivatives pharmaceutical compositions containing them and processes for their preparationInfo
- Publication number
- IL97289A IL97289A IL9728991A IL9728991A IL97289A IL 97289 A IL97289 A IL 97289A IL 9728991 A IL9728991 A IL 9728991A IL 9728991 A IL9728991 A IL 9728991A IL 97289 A IL97289 A IL 97289A
- Authority
- IL
- Israel
- Prior art keywords
- alkyl
- compound
- hydrogen
- carbon atoms
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- 230000008569 process Effects 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 8
- 239000008194 pharmaceutical composition Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 49
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 40
- 239000001257 hydrogen Substances 0.000 claims abstract description 40
- -1 carboxamidomethyl Chemical group 0.000 claims abstract description 34
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 9
- 239000000460 chlorine Substances 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 7
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims abstract description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 6
- 239000011737 fluorine Substances 0.000 claims abstract description 6
- 239000011630 iodine Substances 0.000 claims abstract description 6
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 239000007787 solid Substances 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 43
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 22
- 125000004494 ethyl ester group Chemical group 0.000 claims description 14
- 241000124008 Mammalia Species 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 10
- 238000001704 evaporation Methods 0.000 claims description 8
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 7
- 238000010992 reflux Methods 0.000 claims description 7
- 239000012312 sodium hydride Substances 0.000 claims description 7
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- NGZYTECBMJVSJH-UHFFFAOYSA-N 8-(3-(trifluoromethyl)phenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylene-3,5(4h)-dione Chemical compound FC(F)(F)C1=CC=CC(C=2N3C=4N(C(NC(=O)C=4C=N3)=O)CC=2)=C1 NGZYTECBMJVSJH-UHFFFAOYSA-N 0.000 claims description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 claims description 3
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- HQDDYUKOPXEYQL-UHFFFAOYSA-N 7,8-dihydro-8-(3-(trifluoromethyl)phenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylene-3,5(4h)-dione Chemical compound FC(F)(F)C1=CC=CC(C2N3C=4N(C(NC(=O)C=4C=N3)=O)CC2)=C1 HQDDYUKOPXEYQL-UHFFFAOYSA-N 0.000 claims 1
- 230000002152 alkylating effect Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000001035 drying Methods 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
- 230000001777 nootropic effect Effects 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 abstract description 6
- 230000003276 anti-hypertensive effect Effects 0.000 abstract description 2
- 239000002249 anxiolytic agent Substances 0.000 abstract description 2
- 239000000047 product Substances 0.000 description 38
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 28
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 238000012360 testing method Methods 0.000 description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000012362 glacial acetic acid Substances 0.000 description 15
- 239000002244 precipitate Substances 0.000 description 14
- 238000003756 stirring Methods 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 238000001914 filtration Methods 0.000 description 12
- 230000001537 neural effect Effects 0.000 description 11
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 11
- 241000699670 Mus sp. Species 0.000 description 10
- LDIJKUBTLZTFRG-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine Chemical class N1=CC=CN2N=CC=C21 LDIJKUBTLZTFRG-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 206010021143 Hypoxia Diseases 0.000 description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 9
- 230000037396 body weight Effects 0.000 description 9
- 230000001146 hypoxic effect Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000001301 oxygen Substances 0.000 description 9
- 229910052760 oxygen Inorganic materials 0.000 description 9
- 230000009467 reduction Effects 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 239000006185 dispersion Substances 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000012258 stirred mixture Substances 0.000 description 7
- 230000004083 survival effect Effects 0.000 description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 231100000871 behavioral problem Toxicity 0.000 description 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 6
- 230000001149 cognitive effect Effects 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- SIPFGIVYWGWAFF-UHFFFAOYSA-N 7-(2,5-dichlorophenyl)-2-methyl-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC(=O)C=1C(C)=NN2C=1NCC=C2C1=CC(Cl)=CC=C1Cl SIPFGIVYWGWAFF-UHFFFAOYSA-N 0.000 description 4
- KUNVUVMAYULPOI-UHFFFAOYSA-N 7-(2,5-dichlorophenyl)-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(N)=O)C(C)=NN2C=1C1=CC(Cl)=CC=C1Cl KUNVUVMAYULPOI-UHFFFAOYSA-N 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229940030600 antihypertensive agent Drugs 0.000 description 4
- 230000004872 arterial blood pressure Effects 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002480 mineral oil Substances 0.000 description 4
- 235000010446 mineral oil Nutrition 0.000 description 4
- 239000012047 saturated solution Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
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- 208000000044 Amnesia Diseases 0.000 description 3
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
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- 239000002585 base Substances 0.000 description 3
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- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 3
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- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 3
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- RRHORVAOECWFPT-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound C1=CC=NC2=C(C#N)C=NN21 RRHORVAOECWFPT-UHFFFAOYSA-N 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
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- WABFHIRTWFQGJP-UHFFFAOYSA-N 1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),10-triene-5,7-dione Chemical class C1=CCN2C(=O)NC(=O)C3=C2N1N=C3 WABFHIRTWFQGJP-UHFFFAOYSA-N 0.000 description 2
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical class NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 2
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- CMDLMEWUTRWGGS-UHFFFAOYSA-N 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1CCNC2=C(C(=O)N)C=NN21 CMDLMEWUTRWGGS-UHFFFAOYSA-N 0.000 description 2
- VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 2
- NISNJNISVXZUQS-UHFFFAOYSA-N 7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)N)C=NN2C=1C1=CC=CC(C(F)(F)F)=C1 NISNJNISVXZUQS-UHFFFAOYSA-N 0.000 description 2
- WHYJXQDNGUFTQA-UHFFFAOYSA-N 7-pyridin-3-ylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)N)C=NN2C=1C1=CC=CN=C1 WHYJXQDNGUFTQA-UHFFFAOYSA-N 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
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- 206010012289 Dementia Diseases 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 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 2
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- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
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- HCWCAKKEBCNQJP-UHFFFAOYSA-N magnesium orthosilicate Chemical compound [Mg+2].[Mg+2].[O-][Si]([O-])([O-])[O-] HCWCAKKEBCNQJP-UHFFFAOYSA-N 0.000 description 2
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- 235000019792 magnesium silicate Nutrition 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
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- XMRIUEGHBZTNND-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C1=CC=NC2=C(C(=O)N)C=NN21 XMRIUEGHBZTNND-UHFFFAOYSA-N 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
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- 238000011699 spontaneously hypertensive rat Methods 0.000 description 2
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- 125000001424 substituent group Chemical group 0.000 description 2
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- 125000001544 thienyl group Chemical group 0.000 description 2
- YCTFUHSIWVLYLO-IMSRSEOMSA-N (2r,3r,4s,5r)-2-[6-(1,2-dihydroacenaphthylen-1-ylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical class O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC=NC(NC3C=4C=CC=C5C=CC=C(C=45)C3)=C2N=C1 YCTFUHSIWVLYLO-IMSRSEOMSA-N 0.000 description 1
- YYVRLHVUPJBXRX-UHFFFAOYSA-N 1-(2,5-dichlorophenyl)-3-(dimethylamino)prop-2-en-1-one Chemical compound CN(C)C=CC(=O)C1=CC(Cl)=CC=C1Cl YYVRLHVUPJBXRX-UHFFFAOYSA-N 0.000 description 1
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/16—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Photoreceptors In Electrophotography (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/482,568 US5013737A (en) | 1988-02-22 | 1990-02-21 | 2,4,8-Trisubstituted-3H,6H-1,4,5A,8A-tetraazaacenaphtylene-3,5-(4H)-diones and 2,4-8-trisubstituted-4,5-dihydro-5-thioxo-3H,6H-1,4,5A,8A-tetrazaacenaphthylen-3-ones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL97289A0 IL97289A0 (en) | 1992-05-25 |
| IL97289A true IL97289A (en) | 1995-06-29 |
Family
ID=23916572
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9728991A IL97289A (en) | 1990-02-21 | 1991-02-20 | 8-(hetero) aryl-3h 6h-1 4 5a 8-tetraazaacenaphthylene-3,5(4h)-dione derivatives pharmaceutical compositions containing them and processes for their preparation |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5013737A (cs) |
| EP (1) | EP0443312B1 (cs) |
| JP (1) | JP3046851B2 (cs) |
| KR (1) | KR0183395B1 (cs) |
| AT (1) | ATE152723T1 (cs) |
| AU (1) | AU640202B2 (cs) |
| CA (1) | CA2036589A1 (cs) |
| CZ (1) | CZ285584B6 (cs) |
| DE (1) | DE69125962T2 (cs) |
| DK (1) | DK0443312T3 (cs) |
| ES (1) | ES2102371T3 (cs) |
| FI (1) | FI93963C (cs) |
| GR (1) | GR3024063T3 (cs) |
| HU (1) | HUT60500A (cs) |
| IE (1) | IE910575A1 (cs) |
| IL (1) | IL97289A (cs) |
| NO (1) | NO177749C (cs) |
| NZ (1) | NZ237123A (cs) |
| PH (1) | PH27464A (cs) |
| PL (1) | PL166100B1 (cs) |
| PT (1) | PT96805B (cs) |
| SG (1) | SG47638A1 (cs) |
| SK (1) | SK279997B6 (cs) |
| ZA (1) | ZA911260B (cs) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20010080402A (ko) * | 1998-11-12 | 2001-08-22 | 추후기재 | Ｃｒｆ 수용체 길항제 및 그와 관련된 방법 |
| EP1129091B1 (en) * | 1998-11-12 | 2002-10-02 | Neurocrine Biosciences, Inc. | Crf receptor antagonists and methods relating thereto |
| BRPI0708813A2 (pt) * | 2006-03-17 | 2011-05-24 | Wyeth Corp | composto; composição; método de tratamento, inibição do crescimento ou erradicaçõ de neoplasias em um mamìfero necessitado; método de tratamento dse cáncer em um mamìfero necessitado; e mistura |
| US20070219183A1 (en) * | 2006-03-17 | 2007-09-20 | Wyeth | Dihydropyrazolo[1,5-A]pyrimidine and dihydroimidazo[1,5-A]pyrimidine derivatives and methods of use thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4178449A (en) * | 1978-04-17 | 1979-12-11 | American Cyanamid Company | Pyrazolo[1,5-a]pyrimidines and imidazo-[1,5-a]pyrimidines |
| US4236005A (en) * | 1979-07-02 | 1980-11-25 | American Cyanamid Company | Imidazo[1,5-a]pyrimidines |
| US4281000A (en) * | 1979-07-09 | 1981-07-28 | American Cyanamid Company | Substituted pyrazolo (1,5-a)pyrimidines and their use as anxiolytic agents |
| US4713383A (en) * | 1984-10-01 | 1987-12-15 | Ciba-Geigy Corporation | Triazoloquinazoline compounds, and their methods of preparation, pharmaceutical compositions, and uses |
| US4614732A (en) * | 1984-10-26 | 1986-09-30 | Warner-Lambert Company | N6 -acenaphthyl adenosines and analogs thereof |
| ES2061739T3 (es) * | 1988-02-22 | 1994-12-16 | American Cyanamid Co | 5-(amino-sustituida)-8-(fenil o fenil-sustituidas)-3h,6h-1,4,5a,8a-tetraazaacenaftilen-3-onas, que son utiles como agentes para el tratamiento de trastornos del comportamiento cognitivo y neural asociado con el mismo en animales mamiferos. |
-
1990
- 1990-02-21 US US07/482,568 patent/US5013737A/en not_active Expired - Lifetime
-
1991
- 1991-01-08 EP EP91100189A patent/EP0443312B1/en not_active Expired - Lifetime
- 1991-01-08 DE DE69125962T patent/DE69125962T2/de not_active Expired - Fee Related
- 1991-01-08 AT AT91100189T patent/ATE152723T1/de not_active IP Right Cessation
- 1991-01-08 SG SG1996003303A patent/SG47638A1/en unknown
- 1991-01-08 DK DK91100189.9T patent/DK0443312T3/da active
- 1991-01-08 ES ES91100189T patent/ES2102371T3/es not_active Expired - Lifetime
- 1991-02-14 NZ NZ23712391A patent/NZ237123A/en unknown
- 1991-02-19 CZ CS91419A patent/CZ285584B6/cs not_active IP Right Cessation
- 1991-02-19 JP JP3045452A patent/JP3046851B2/ja not_active Expired - Lifetime
- 1991-02-19 PH PH42023A patent/PH27464A/en unknown
- 1991-02-19 SK SK419-91A patent/SK279997B6/sk unknown
- 1991-02-19 PT PT96805A patent/PT96805B/pt not_active IP Right Cessation
- 1991-02-19 CA CA002036589A patent/CA2036589A1/en not_active Abandoned
- 1991-02-20 IE IE057591A patent/IE910575A1/en not_active Application Discontinuation
- 1991-02-20 KR KR1019910002713A patent/KR0183395B1/ko not_active Expired - Fee Related
- 1991-02-20 NO NO910686A patent/NO177749C/no not_active IP Right Cessation
- 1991-02-20 FI FI910816A patent/FI93963C/fi active
- 1991-02-20 IL IL9728991A patent/IL97289A/en not_active IP Right Cessation
- 1991-02-20 AU AU71225/91A patent/AU640202B2/en not_active Ceased
- 1991-02-20 ZA ZA911260A patent/ZA911260B/xx unknown
- 1991-02-21 PL PL91289157A patent/PL166100B1/pl unknown
- 1991-02-21 HU HU91584A patent/HUT60500A/hu unknown
-
1997
- 1997-07-09 GR GR970401719T patent/GR3024063T3/el unknown
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