DK172397B1 - 5-Amino-8-phenyl-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-on-forbindelser, farmaceutisk præparat og anvendelse af derivaterne til fremstilling af farmaceutisk præparat - Google Patents
5-Amino-8-phenyl-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-on-forbindelser, farmaceutisk præparat og anvendelse af derivaterne til fremstilling af farmaceutisk præparat Download PDFInfo
- Publication number
- DK172397B1 DK172397B1 DK079589A DK79589A DK172397B1 DK 172397 B1 DK172397 B1 DK 172397B1 DK 079589 A DK079589 A DK 079589A DK 79589 A DK79589 A DK 79589A DK 172397 B1 DK172397 B1 DK 172397B1
- Authority
- DK
- Denmark
- Prior art keywords
- phenyl
- trifluoromethyl
- mixture
- tetraazaacenaphthylen
- stirred
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 6
- AFRXXRQTYLNRSL-UHFFFAOYSA-N 7-amino-11-phenyl-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-5-one Chemical class C=1CN(C=23)C(N)=NC(=O)C=2C=NN3C=1C1=CC=CC=C1 AFRXXRQTYLNRSL-UHFFFAOYSA-N 0.000 title claims 2
- 239000000825 pharmaceutical preparation Substances 0.000 title 2
- 150000001875 compounds Chemical class 0.000 claims description 49
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- -1 hydroxy, 4-morpholinyl Chemical group 0.000 claims description 40
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 36
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 21
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- 230000001537 neural effect Effects 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 230000001149 cognitive effect Effects 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- LYFFMDZFPCZNMS-UHFFFAOYSA-N 5-amino-8-[3-(trifluoromethyl)phenyl]-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Chemical group C=1CN(C=23)C(N)=NC(=O)C=2C=NN3C=1C1=CC=CC(C(F)(F)F)=C1 LYFFMDZFPCZNMS-UHFFFAOYSA-N 0.000 claims description 4
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- RKMMMWVFSVOSFK-UHFFFAOYSA-N 7-(2-methylpropyl)-11-[3-(trifluoromethyl)phenyl]-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-5-one Chemical group C=1CN(C=23)C(CC(C)C)=NC(=O)C=2C=NN3C=1C1=CC=CC(C(F)(F)F)=C1 RKMMMWVFSVOSFK-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- GPADRTORXVCSGJ-UHFFFAOYSA-N [5-oxo-11-[3-(trifluoromethyl)phenyl]-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-7-yl]carbamic acid Chemical group C=1CN(C=23)C(NC(=O)O)=NC(=O)C=2C=NN3C=1C1=CC=CC(C(F)(F)F)=C1 GPADRTORXVCSGJ-UHFFFAOYSA-N 0.000 claims 1
- 230000006399 behavior Effects 0.000 claims 1
- JFAUDVHAXVIITQ-UHFFFAOYSA-N chembl139494 Chemical group C=1CN(C=23)C(NCC)=NC(=O)C=2C=NN3C=1C1=CC=CC(C(F)(F)F)=C1 JFAUDVHAXVIITQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 90
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 89
- 239000007787 solid Substances 0.000 description 79
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 58
- 239000000047 product Substances 0.000 description 58
- 239000011541 reaction mixture Substances 0.000 description 52
- 239000000243 solution Substances 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 238000001914 filtration Methods 0.000 description 37
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 238000003756 stirring Methods 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- 239000013078 crystal Substances 0.000 description 24
- 239000002244 precipitate Substances 0.000 description 23
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 21
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 229910000104 sodium hydride Inorganic materials 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- HGOQXPTZTZPWMD-UHFFFAOYSA-N 1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-5-one Chemical class C1C=CN2N=CC3=C2N1C=NC3=O HGOQXPTZTZPWMD-UHFFFAOYSA-N 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 17
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 17
- 239000003921 oil Substances 0.000 description 17
- 235000019198 oils Nutrition 0.000 description 17
- 239000012312 sodium hydride Substances 0.000 description 17
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
- RAFNCPHFRHZCPS-UHFFFAOYSA-N di(imidazol-1-yl)methanethione Chemical compound C1=CN=CN1C(=S)N1C=CN=C1 RAFNCPHFRHZCPS-UHFFFAOYSA-N 0.000 description 16
- 239000006185 dispersion Substances 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 229960000583 acetic acid Drugs 0.000 description 13
- 239000002480 mineral oil Substances 0.000 description 13
- 235000010446 mineral oil Nutrition 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 11
- 239000012362 glacial acetic acid Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 11
- 206010021143 Hypoxia Diseases 0.000 description 10
- 241000699670 Mus sp. Species 0.000 description 10
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- XMRIUEGHBZTNND-UHFFFAOYSA-N pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical class C1=CC=NC2=C(C(=O)N)C=NN21 XMRIUEGHBZTNND-UHFFFAOYSA-N 0.000 description 9
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 9
- 230000004083 survival effect Effects 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 8
- 239000000706 filtrate Substances 0.000 description 8
- 230000001146 hypoxic effect Effects 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 235000011089 carbon dioxide Nutrition 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 6
- 125000006309 butyl amino group Chemical group 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- GJFNRSDCSTVPCJ-UHFFFAOYSA-N 1,8-bis(dimethylamino)naphthalene Chemical compound C1=CC(N(C)C)=C2C(N(C)C)=CC=CC2=C1 GJFNRSDCSTVPCJ-UHFFFAOYSA-N 0.000 description 5
- 241000124008 Mammalia Species 0.000 description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 5
- 230000008020 evaporation Effects 0.000 description 5
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 5
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 5
- 150000003139 primary aliphatic amines Chemical class 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000002775 capsule Substances 0.000 description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000006188 syrup Substances 0.000 description 4
- 235000020357 syrup Nutrition 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- YMVFJGSXZNNUDW-UHFFFAOYSA-N (4-chlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C=C1 YMVFJGSXZNNUDW-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- KZFGNDBDCDFDSL-UHFFFAOYSA-N 7-[3-(trifluoromethyl)phenyl]-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC(=O)C=1C=NN2C=1NCC=C2C1=CC=CC(C(F)(F)F)=C1 KZFGNDBDCDFDSL-UHFFFAOYSA-N 0.000 description 3
- 208000000044 Amnesia Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000032683 aging Effects 0.000 description 3
- CPEKAXYCDKETEN-UHFFFAOYSA-N benzoyl isothiocyanate Chemical compound S=C=NC(=O)C1=CC=CC=C1 CPEKAXYCDKETEN-UHFFFAOYSA-N 0.000 description 3
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000006071 cream Substances 0.000 description 3
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000037149 energy metabolism Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000006870 function Effects 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 150000002540 isothiocyanates Chemical class 0.000 description 3
- 239000007937 lozenge Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- FUXJMHXHGDAHPD-UHFFFAOYSA-N pyrimidine-2-carboxamide Chemical compound NC(=O)C1=NC=CC=N1 FUXJMHXHGDAHPD-UHFFFAOYSA-N 0.000 description 3
- 239000012047 saturated solution Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 description 2
- KDHWOCLBMVSZPG-UHFFFAOYSA-N 3-imidazol-1-ylpropan-1-amine Chemical compound NCCCN1C=CN=C1 KDHWOCLBMVSZPG-UHFFFAOYSA-N 0.000 description 2
- QVIVSNGEBQQGQA-UHFFFAOYSA-N 4,5-dihydro-8-(3-methoxyphenyl)-5-thioxo-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Chemical compound COC1=CC=CC(C=2N3C=4N(C(NC(=O)C=4C=N3)=S)CC=2)=C1 QVIVSNGEBQQGQA-UHFFFAOYSA-N 0.000 description 2
- SSGQBXROTIHBCN-UHFFFAOYSA-N 4,5-dihydro-8-phenyl-5-thioxo-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Chemical compound C=12N3N=CC=1C(=O)NC(=S)N2CC=C3C1=CC=CC=C1 SSGQBXROTIHBCN-UHFFFAOYSA-N 0.000 description 2
- NIEIVFHQPZKLEN-UHFFFAOYSA-N 7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound C=1C=NC2=C(C(=O)N)C=NN2C=1C1=CC=CC=C1 NIEIVFHQPZKLEN-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 206010002660 Anoxia Diseases 0.000 description 2
- 241000976983 Anoxia Species 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- 241000167854 Bourreria succulenta Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000026139 Memory disease Diseases 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 229930006000 Sucrose Natural products 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 230000007953 anoxia Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 231100000871 behavioral problem Toxicity 0.000 description 2
- 230000003542 behavioural effect Effects 0.000 description 2
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- 235000019693 cherries Nutrition 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000008120 corn starch Substances 0.000 description 2
- 239000002178 crystalline material Substances 0.000 description 2
- 230000003292 diminished effect Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- BDTDECDAHYOJRO-UHFFFAOYSA-N ethyl n-(sulfanylidenemethylidene)carbamate Chemical compound CCOC(=O)N=C=S BDTDECDAHYOJRO-UHFFFAOYSA-N 0.000 description 2
- 235000003599 food sweetener Nutrition 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 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
- 230000006984 memory degeneration Effects 0.000 description 2
- 208000023060 memory loss Diseases 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical compound NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229960001697 physostigmine Drugs 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 208000020016 psychiatric disease Diseases 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 230000035939 shock Effects 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000003765 sweetening agent Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- CJAAPVQEZPAQNI-UHFFFAOYSA-N (2-methylphenyl)methanamine Chemical compound CC1=CC=CC=C1CN CJAAPVQEZPAQNI-UHFFFAOYSA-N 0.000 description 1
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- IAADPEJYEZPFOT-UHFFFAOYSA-N 1-(1h-imidazol-2-yl)propan-1-amine Chemical compound CCC(N)C1=NC=CN1 IAADPEJYEZPFOT-UHFFFAOYSA-N 0.000 description 1
- FRYSRVXPZFAABD-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-(dimethylamino)-2-methylprop-2-en-1-one Chemical compound CN(C)C=C(C)C(=O)C1=CC=C(Cl)C=C1 FRYSRVXPZFAABD-UHFFFAOYSA-N 0.000 description 1
- ADCYRBXQAJXJTD-UHFFFAOYSA-N 1-(4-chlorophenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(Cl)C=C1 ADCYRBXQAJXJTD-UHFFFAOYSA-N 0.000 description 1
- IQXXEPZFOOTTBA-UHFFFAOYSA-N 1-benzylpiperazine Chemical compound C=1C=CC=CC=1CN1CCNCC1 IQXXEPZFOOTTBA-UHFFFAOYSA-N 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- GPSFHCVYMLUWDL-UHFFFAOYSA-N 10-methyl-7-sulfanylidene-11-[3-(trifluoromethyl)phenyl]-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),10-trien-5-one Chemical compound N12N=CC(C(NC3=S)=O)=C2N3CC(C)=C1C1=CC=CC(C(F)(F)F)=C1 GPSFHCVYMLUWDL-UHFFFAOYSA-N 0.000 description 1
- SWPDRDQDAXBYJU-UHFFFAOYSA-N 11-[3-(trifluoromethyl)phenyl]-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-5-one Chemical compound FC(F)(F)C1=CC=CC(C=2N3N=CC=4C(=O)N=CN(C3=4)CC=2)=C1 SWPDRDQDAXBYJU-UHFFFAOYSA-N 0.000 description 1
- LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical compound ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 description 1
- MEKOFIRRDATTAG-UHFFFAOYSA-N 2,2,5,8-tetramethyl-3,4-dihydrochromen-6-ol Chemical compound C1CC(C)(C)OC2=C1C(C)=C(O)C=C2C MEKOFIRRDATTAG-UHFFFAOYSA-N 0.000 description 1
- QKWWDTYDYOFRJL-UHFFFAOYSA-N 2,2-dimethoxyethanamine Chemical compound COC(CN)OC QKWWDTYDYOFRJL-UHFFFAOYSA-N 0.000 description 1
- UDQLLANHQLALPU-UHFFFAOYSA-N 2,6-dimethyl-7-phenyl-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC(=O)C=1C(C)=NN2C=1NCC(C)=C2C1=CC=CC=C1 UDQLLANHQLALPU-UHFFFAOYSA-N 0.000 description 1
- VKCJXGNDLNJLBN-UHFFFAOYSA-N 2,6-dimethyl-7-phenylpyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC=1C=NC2=C(C#N)C(C)=NN2C=1C1=CC=CC=C1 VKCJXGNDLNJLBN-UHFFFAOYSA-N 0.000 description 1
- VCTFDJWAERQRMR-UHFFFAOYSA-N 2,6-dimethyl-7-phenylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC=1C=NC2=C(C(N)=O)C(C)=NN2C=1C1=CC=CC=C1 VCTFDJWAERQRMR-UHFFFAOYSA-N 0.000 description 1
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 description 1
- JGNKBOHSDKTXJX-UHFFFAOYSA-N 2-chloro-n-[3-oxo-8-[3-(trifluoromethyl)phenyl]-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-5-yl]acetamide Chemical compound FC(F)(F)C1=CC=CC(C=2N3N=CC=4C(=O)N=C(NC(=O)CCl)N(C3=4)CC=2)=C1 JGNKBOHSDKTXJX-UHFFFAOYSA-N 0.000 description 1
- BFKYQYMHJANOTR-UHFFFAOYSA-N 2h-pyrimidine-1-carbonitrile Chemical compound N#CN1CN=CC=C1 BFKYQYMHJANOTR-UHFFFAOYSA-N 0.000 description 1
- MJKGRSIGRDJWLU-UHFFFAOYSA-N 3-(dimethylamino)-2-methyl-1-phenylprop-2-en-1-one Chemical compound CN(C)C=C(C)C(=O)C1=CC=CC=C1 MJKGRSIGRDJWLU-UHFFFAOYSA-N 0.000 description 1
- XBGXGCOLWCMVOI-UHFFFAOYSA-N 3-(trifluoromethyl)benzamide Chemical compound NC(=O)C1=CC=CC(C(F)(F)F)=C1 XBGXGCOLWCMVOI-UHFFFAOYSA-N 0.000 description 1
- CRRHJAMDQMQGKG-UHFFFAOYSA-N 3-amino-5-methyl-1h-pyrazole-4-carbonitrile Chemical compound CC=1NN=C(N)C=1C#N CRRHJAMDQMQGKG-UHFFFAOYSA-N 0.000 description 1
- DPGLRSUXJBFBGT-UHFFFAOYSA-N 4,5-dihydro-5-thioxo-8-(3-methylphenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Chemical compound CC1=CC=CC(C=2N3C=4N(C(NC(=O)C=4C=N3)=S)CC=2)=C1 DPGLRSUXJBFBGT-UHFFFAOYSA-N 0.000 description 1
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 description 1
- NKSUHGWUDGKGKC-UHFFFAOYSA-N 5-(methylthio)-8-(3-(trifluoromethyl)phenyl)-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Chemical compound C=1CN(C=23)C(SC)=NC(=O)C=2C=NN3C=1C1=CC=CC(C(F)(F)F)=C1 NKSUHGWUDGKGKC-UHFFFAOYSA-N 0.000 description 1
- FFNKBQRKZRMYCL-UHFFFAOYSA-N 5-amino-1h-pyrazole-4-carbonitrile Chemical compound NC1=NNC=C1C#N FFNKBQRKZRMYCL-UHFFFAOYSA-N 0.000 description 1
- ZTPONYHBWRYSPM-UHFFFAOYSA-N 6-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC=1C=NC2=C(C#N)C=NN2C=1C1=CC=CC(C(F)(F)F)=C1 ZTPONYHBWRYSPM-UHFFFAOYSA-N 0.000 description 1
- LVTOYXVCIZVTOI-UHFFFAOYSA-N 6-methyl-7-[3-(trifluoromethyl)phenyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC=1C=NC2=C(C(N)=O)C=NN2C=1C1=CC=CC(C(F)(F)F)=C1 LVTOYXVCIZVTOI-UHFFFAOYSA-N 0.000 description 1
- LKUHPMZWWMDZTG-UHFFFAOYSA-N 7-(3-fluorophenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC(=O)C=1C=NN2C=1NCC=C2C1=CC=CC(F)=C1 LKUHPMZWWMDZTG-UHFFFAOYSA-N 0.000 description 1
- FPWOERTWNJOEHJ-UHFFFAOYSA-N 7-(3-fluorophenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound FC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 FPWOERTWNJOEHJ-UHFFFAOYSA-N 0.000 description 1
- PEGAJTXIULIBFZ-UHFFFAOYSA-N 7-(3-methoxyphenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine Chemical compound COC1=CC=CC(C=2N3N=CC=C3NCC=2)=C1 PEGAJTXIULIBFZ-UHFFFAOYSA-N 0.000 description 1
- TUYFVBMFYVWUMU-UHFFFAOYSA-N 7-(3-methylphenyl)-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=CC=CC(C=2N3N=CC(=C3NCC=2)C(N)=O)=C1 TUYFVBMFYVWUMU-UHFFFAOYSA-N 0.000 description 1
- CKMAHHVZMHOADP-UHFFFAOYSA-N 7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C#N)=C1 CKMAHHVZMHOADP-UHFFFAOYSA-N 0.000 description 1
- HNKGGVGQAVODNJ-UHFFFAOYSA-N 7-(3-methylphenyl)pyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC1=CC=CC(C=2N3N=CC(=C3N=CC=2)C(N)=O)=C1 HNKGGVGQAVODNJ-UHFFFAOYSA-N 0.000 description 1
- NPHCABLWEGXCFW-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-methyl-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound ClC1=CC=C(C=C1)C1=C(CNC=2N1N=CC2C(=O)N)C NPHCABLWEGXCFW-UHFFFAOYSA-N 0.000 description 1
- HLNQYLVMWVLMEX-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-methylpyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound CC=1C=NC2=C(C#N)C=NN2C=1C1=CC=C(Cl)C=C1 HLNQYLVMWVLMEX-UHFFFAOYSA-N 0.000 description 1
- UFXUSFXTHHGKCF-UHFFFAOYSA-N 7-(4-chlorophenyl)-6-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound CC=1C=NC2=C(C(N)=O)C=NN2C=1C1=CC=C(Cl)C=C1 UFXUSFXTHHGKCF-UHFFFAOYSA-N 0.000 description 1
- 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 1
- LUEHJRPKQANHLR-UHFFFAOYSA-N 7-phenyl-4,5-dihydropyrazolo[1,5-a]pyrimidine-3-carboxamide Chemical compound NC(=O)C=1C=NN2C=1NCC=C2C1=CC=CC=C1 LUEHJRPKQANHLR-UHFFFAOYSA-N 0.000 description 1
- JEIMLAZQABXLEV-UHFFFAOYSA-N 7-phenylpyrazolo[1,5-a]pyrimidine-3-carbonitrile Chemical compound C=1C=NC2=C(C#N)C=NN2C=1C1=CC=CC=C1 JEIMLAZQABXLEV-UHFFFAOYSA-N 0.000 description 1
- MGGBVIVNJXJOOF-UHFFFAOYSA-N 7-sulfanylidene-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),10-trien-5-one Chemical compound C1C=CN2N=CC3=C2N1C(=S)NC3=O MGGBVIVNJXJOOF-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZYFNWNDMHRPMFY-UHFFFAOYSA-N 8-(3-fluorophenyl)-4,5-dihydro-5-thioxo-3h,6h-1,4,5a,8a-tetraazaacenaphthylen-3-one Chemical compound FC1=CC=CC(C=2N3C=4N(C(NC(=O)C=4C=N3)=S)CC=2)=C1 ZYFNWNDMHRPMFY-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 208000031091 Amnestic disease Diseases 0.000 description 1
- 241000416162 Astragalus gummifer Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- JXRHTGUEFQCKFI-UHFFFAOYSA-N COC1=CC=CC(C=2N3N=CC=4C(=O)N=C(NCC(C)C)N(C3=4)CC=2)=C1 Chemical compound COC1=CC=CC(C=2N3N=CC=4C(=O)N=C(NCC(C)C)N(C3=4)CC=2)=C1 JXRHTGUEFQCKFI-UHFFFAOYSA-N 0.000 description 1
- XUHKNPQAQPGRQM-UHFFFAOYSA-N COC=1C=C(C=CC1)C1=CCNC=2N1N=CC2C(=O)N Chemical compound COC=1C=C(C=CC1)C1=CCNC=2N1N=CC2C(=O)N XUHKNPQAQPGRQM-UHFFFAOYSA-N 0.000 description 1
- IYMYLGSLPNUUCY-UHFFFAOYSA-N CSC(N(CC=C(C1=CC(C(F)(F)F)=CC=C1)N1N=C2)C1=C2C(N)=O)=NC(C1=CC=CC=C1)=O Chemical compound CSC(N(CC=C(C1=CC(C(F)(F)F)=CC=C1)N1N=C2)C1=C2C(N)=O)=NC(C1=CC=CC=C1)=O IYMYLGSLPNUUCY-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000028698 Cognitive impairment Diseases 0.000 description 1
- 206010012289 Dementia Diseases 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010019196 Head injury Diseases 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 235000010643 Leucaena leucocephala Nutrition 0.000 description 1
- 240000007472 Leucaena leucocephala Species 0.000 description 1
- 244000246386 Mentha pulegium Species 0.000 description 1
- 235000016257 Mentha pulegium Nutrition 0.000 description 1
- 235000004357 Mentha x piperita Nutrition 0.000 description 1
- ZSXGLVDWWRXATF-UHFFFAOYSA-N N,N-dimethylformamide dimethyl acetal Chemical compound COC(OC)N(C)C ZSXGLVDWWRXATF-UHFFFAOYSA-N 0.000 description 1
- PXBWMCCBVVDHME-UHFFFAOYSA-N N-(5-oxo-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-7-yl)benzamide Chemical compound N=1C(=O)C(=C23)C=NN3C=CCN2C=1NC(=O)C1=CC=CC=C1 PXBWMCCBVVDHME-UHFFFAOYSA-N 0.000 description 1
- WFIJNOHGMINJLW-UHFFFAOYSA-N N-[5-oxo-11-[3-(trifluoromethyl)phenyl]-1,2,6,8-tetrazatricyclo[6.3.1.04,12]dodeca-2,4(12),6,10-tetraen-7-yl]benzamide Chemical compound FC(F)(F)C1=CC=CC(C=2N3N=CC=4C(=O)N=C(NC(=O)C=5C=CC=CC=5)N(C3=4)CC=2)=C1 WFIJNOHGMINJLW-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 101150036449 SIRPA gene Proteins 0.000 description 1
- 206010039966 Senile dementia Diseases 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical class [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 229920001615 Tragacanth Polymers 0.000 description 1
- 208000003443 Unconsciousness Diseases 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- 230000003925 brain function Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 208000010877 cognitive disease Diseases 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000003405 delayed action preparation Substances 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000003467 diminishing effect Effects 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000001050 hortel pimenta Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N methyl monoether Natural products COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- RWIVICVCHVMHMU-UHFFFAOYSA-N n-aminoethylmorpholine Chemical compound NCCN1CCOCC1 RWIVICVCHVMHMU-UHFFFAOYSA-N 0.000 description 1
- 230000001722 neurochemical effect Effects 0.000 description 1
- 230000000926 neurological effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000011302 passive avoidance test Methods 0.000 description 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004797 therapeutic response Effects 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 125000000464 thioxo group Chemical group S=* 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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
- C07D487/12—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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15844888A | 1988-02-22 | 1988-02-22 | |
| US15844888 | 1988-02-22 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK79589D0 DK79589D0 (da) | 1989-02-21 |
| DK79589A DK79589A (da) | 1989-08-23 |
| DK172397B1 true DK172397B1 (da) | 1998-05-18 |
Family
ID=22568168
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK079589A DK172397B1 (da) | 1988-02-22 | 1989-02-21 | 5-Amino-8-phenyl-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-on-forbindelser, farmaceutisk præparat og anvendelse af derivaterne til fremstilling af farmaceutisk præparat |
Country Status (23)
| Country | Link |
|---|---|
| EP (1) | EP0329940B1 (cs) |
| JP (1) | JP2641556B2 (cs) |
| KR (1) | KR970009226B1 (cs) |
| AR (1) | AR247211A1 (cs) |
| AT (1) | ATE99686T1 (cs) |
| AU (1) | AU611769B2 (cs) |
| CA (1) | CA1329594C (cs) |
| CZ (1) | CZ284273B6 (cs) |
| DD (1) | DD283624A5 (cs) |
| DE (1) | DE68911951T2 (cs) |
| DK (1) | DK172397B1 (cs) |
| ES (1) | ES2061739T3 (cs) |
| FI (1) | FI89922C (cs) |
| HU (1) | HU203554B (cs) |
| IE (1) | IE64147B1 (cs) |
| IL (1) | IL88974A (cs) |
| NO (1) | NO169589C (cs) |
| NZ (1) | NZ228009A (cs) |
| PH (1) | PH26358A (cs) |
| PL (1) | PL158865B1 (cs) |
| PT (1) | PT89766B (cs) |
| SK (1) | SK105589A3 (cs) |
| ZA (1) | ZA891310B (cs) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5013737A (en) * | 1988-02-22 | 1991-05-07 | American Cyanamid Company | 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 |
| EP0562236A1 (en) * | 1992-03-26 | 1993-09-29 | American Cyanamid Company | Process for the synthesis of 5-[(substituted)-amino]-8-[phenyl or substiutued-phenyl]-3H, 6H-1, 4, 5A, 8A-tetraazaacephthylen-3-ones |
| CA2273288A1 (en) * | 1996-12-19 | 1998-06-25 | James Joseph Gibbons | Method of treating or inhibiting neutropenia |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4236005A (en) * | 1979-07-02 | 1980-11-25 | American Cyanamid Company | Imidazo[1,5-a]pyrimidines |
| US4713383A (en) * | 1984-10-01 | 1987-12-15 | Ciba-Geigy Corporation | Triazoloquinazoline compounds, and their methods of preparation, pharmaceutical compositions, and uses |
| US4576943A (en) * | 1984-10-09 | 1986-03-18 | American Cyanamid Company | Pyrazolo[1,5-a]pyrimidines |
| EP0264773A1 (en) * | 1986-10-16 | 1988-04-27 | American Cyanamid Company | 4,5-dihydro and 4,5,6,7-tetrahydropyrazolo[1,5-a]pyrimidines |
-
1989
- 1989-01-16 AT AT89100657T patent/ATE99686T1/de active
- 1989-01-16 ES ES89100657T patent/ES2061739T3/es not_active Expired - Lifetime
- 1989-01-16 EP EP89100657A patent/EP0329940B1/en not_active Expired - Lifetime
- 1989-01-16 DE DE68911951T patent/DE68911951T2/de not_active Expired - Fee Related
- 1989-01-17 IL IL88974A patent/IL88974A/xx not_active IP Right Cessation
- 1989-02-16 NZ NZ228009A patent/NZ228009A/xx unknown
- 1989-02-17 CZ CS891055A patent/CZ284273B6/cs not_active IP Right Cessation
- 1989-02-17 SK SK1055-89A patent/SK105589A3/sk unknown
- 1989-02-20 CA CA000591526A patent/CA1329594C/en not_active Expired - Fee Related
- 1989-02-20 DD DD89325854A patent/DD283624A5/de unknown
- 1989-02-20 PT PT89766A patent/PT89766B/pt not_active IP Right Cessation
- 1989-02-20 PH PH38218A patent/PH26358A/en unknown
- 1989-02-20 JP JP1038480A patent/JP2641556B2/ja not_active Expired - Lifetime
- 1989-02-21 FI FI890826A patent/FI89922C/fi not_active IP Right Cessation
- 1989-02-21 AU AU30172/89A patent/AU611769B2/en not_active Ceased
- 1989-02-21 NO NO890724A patent/NO169589C/no not_active IP Right Cessation
- 1989-02-21 DK DK079589A patent/DK172397B1/da not_active IP Right Cessation
- 1989-02-21 AR AR89313253A patent/AR247211A1/es active
- 1989-02-21 KR KR89002051A patent/KR970009226B1/ko not_active Expired - Fee Related
- 1989-02-21 ZA ZA891310A patent/ZA891310B/xx unknown
- 1989-02-21 IE IE54389A patent/IE64147B1/en not_active IP Right Cessation
- 1989-02-21 PL PL1989277837A patent/PL158865B1/pl unknown
- 1989-02-22 HU HU89856A patent/HU203554B/hu not_active IP Right Cessation
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US8497278B2 (en) | Imidazo[1,2-a]pyridine compounds | |
| KR0133372B1 (ko) | 4-아미노(알킬)시클로헥산-1-카르복사미드 화합물 및 그 용도 | |
| TW201904958A (zh) | 含有咪唑之alk2激酶抑制劑 | |
| JP7763772B2 (ja) | 補体阻害剤としてのピロロピリミジンアミン | |
| PT672666E (pt) | Imidazodiazepina | |
| KR20210031925A (ko) | Ｐ2ｘ3 수용체 길항제 | |
| BR112020023946A2 (pt) | composto heterocíclico, e, composição farmacêutica. | |
| DK172397B1 (da) | 5-Amino-8-phenyl-3H,6H-1,4,5a,8a-tetraazaacenaphthylen-3-on-forbindelser, farmaceutisk præparat og anvendelse af derivaterne til fremstilling af farmaceutisk præparat | |
| WO1998003511A1 (de) | Neue triazolopurine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel | |
| DE69413112T2 (de) | 5-HT3 Pyrrolopyrazinderivate | |
| JP3046851B2 (ja) | ２，４，８−三置換−３Ｈ，６Ｈ−１，４，５ａ，８ａ−テトラアザアセナフチレン−３，５（４Ｈ）−ジオン類 | |
| DE69231244T2 (de) | Pyrazolothiazolopyrimidin-derivate | |
| WO2001003644A9 (en) | Pyrazolopyrimidinone derivatives conjugated to thiophene moieties or benzo [fused] 5-membered heterocycles for erectile dysfunction | |
| DE69320542T2 (de) | Pyrrolothienopyrazin-Verbindungen als 5HT3-Rezeptoren-Antagonisten | |
| OA21436A (en) | Pyrrolopyrimidine amines as complement inhibitors | |
| EA048685B1 (ru) | Содержащие имидазол ингибиторы alk2 киназы |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PBP | Patent lapsed |