CY1641A - Imidazoquinoline derivatives - Google Patents
Imidazoquinoline derivatives Download PDFInfo
- Publication number
- CY1641A CY1641A CY1641A CY164192A CY1641A CY 1641 A CY1641 A CY 1641A CY 1641 A CY1641 A CY 1641A CY 164192 A CY164192 A CY 164192A CY 1641 A CY1641 A CY 1641A
- Authority
- CY
- Cyprus
- Prior art keywords
- compound
- imidazo
- dihydro
- quinolin
- formula
- Prior art date
Links
- RHKWIGHJGOEUSM-UHFFFAOYSA-N 3h-imidazo[4,5-h]quinoline Chemical class C1=CN=C2C(N=CN3)=C3C=CC2=C1 RHKWIGHJGOEUSM-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 103
- 238000000034 method Methods 0.000 claims description 79
- 239000000203 mixture Substances 0.000 claims description 71
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 239000001257 hydrogen Substances 0.000 claims description 58
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 42
- -1 thio compound Chemical class 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 34
- 150000002367 halogens Chemical group 0.000 claims description 34
- 150000002431 hydrogen Chemical group 0.000 claims description 28
- 239000000463 material Substances 0.000 claims description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 229940091173 hydantoin Drugs 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 15
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 15
- 210000001772 blood platelet Anatomy 0.000 claims description 14
- 150000001469 hydantoins Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 12
- 208000010110 spontaneous platelet aggregation Diseases 0.000 claims description 11
- 230000002829 reductive effect Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 230000000297 inotrophic effect Effects 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- 239000007800 oxidant agent Substances 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 239000010452 phosphate Substances 0.000 claims description 6
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 claims description 5
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 230000002152 alkylating effect Effects 0.000 claims description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 4
- YCKKLLYMMVHPIG-UHFFFAOYSA-N 7,8-dimethyl-1,4,9,9a-tetrahydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2CC2=C(C)C(C)=CC=C21 YCKKLLYMMVHPIG-UHFFFAOYSA-N 0.000 claims description 3
- 210000004369 blood Anatomy 0.000 claims description 3
- 239000008280 blood Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- CKJZPMFALWTSJS-UHFFFAOYSA-N 6,7-dimethoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2C=C(OC)C(OC)=CC2=CC2=C1NC(=O)N2 CKJZPMFALWTSJS-UHFFFAOYSA-N 0.000 claims description 2
- ODCKPUDNMNCWMR-UHFFFAOYSA-N 7,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=C(C)C(C)=CC=C21 ODCKPUDNMNCWMR-UHFFFAOYSA-N 0.000 claims description 2
- YEBXOZQMALFMCP-UHFFFAOYSA-N 7-bromo-6,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=C(Br)C(C)=CC2=NC2=C1NC(=O)N2 YEBXOZQMALFMCP-UHFFFAOYSA-N 0.000 claims description 2
- GYPSSORWUVEFFW-UHFFFAOYSA-N 7-chloro-6,8-dimethyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=C(Cl)C(C)=CC2=NC2=C1NC(=O)N2 GYPSSORWUVEFFW-UHFFFAOYSA-N 0.000 claims description 2
- PJRUEHQERHHYKI-UHFFFAOYSA-N 1,7,8-trimethyl-3h-imidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)N(C)C2=CC2=C(C)C(C)=CC=C21 PJRUEHQERHHYKI-UHFFFAOYSA-N 0.000 claims 1
- YEZYOQWGSQOGIH-UHFFFAOYSA-N 1,8-dimethyl-3h-imidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=CC=CC2=NC2=C1N(C)C(=O)N2 YEZYOQWGSQOGIH-UHFFFAOYSA-N 0.000 claims 1
- XTXHKKBSLRGOJD-UHFFFAOYSA-N 7-fluoro-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(F)=CC=C21 XTXHKKBSLRGOJD-UHFFFAOYSA-N 0.000 claims 1
- BSAKVJKPJIQKNP-UHFFFAOYSA-N 7-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(C)=CC=C21 BSAKVJKPJIQKNP-UHFFFAOYSA-N 0.000 claims 1
- FPYRERVDZQWRBO-UHFFFAOYSA-N 7-propan-2-yloxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound N1=C2NC(=O)NC2=CC2=CC(OC(C)C)=CC=C21 FPYRERVDZQWRBO-UHFFFAOYSA-N 0.000 claims 1
- GMKORAPPNLPTAX-UHFFFAOYSA-N 8-methoxy-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(OC)=CC=CC2=NC2=C1NC(=O)N2 GMKORAPPNLPTAX-UHFFFAOYSA-N 0.000 claims 1
- NFWDGDAZJTYAHA-UHFFFAOYSA-N 8-methyl-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical compound C1=C2C(C)=CC=CC2=NC2=C1NC(=O)N2 NFWDGDAZJTYAHA-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 82
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 69
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 66
- 239000000243 solution Substances 0.000 description 47
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 45
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- 238000005481 NMR spectroscopy Methods 0.000 description 32
- 239000007787 solid Substances 0.000 description 32
- 125000003118 aryl group Chemical group 0.000 description 31
- 238000006243 chemical reaction Methods 0.000 description 31
- 239000000543 intermediate Substances 0.000 description 30
- 239000002904 solvent Substances 0.000 description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 26
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 229910052740 iodine Inorganic materials 0.000 description 18
- 239000011630 iodine Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 238000010992 reflux Methods 0.000 description 18
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 17
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 16
- 238000012360 testing method Methods 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 12
- 235000011167 hydrochloric acid Nutrition 0.000 description 12
- 229960000443 hydrochloric acid Drugs 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 229910000029 sodium carbonate Inorganic materials 0.000 description 12
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 10
- 235000019345 sodium thiosulphate Nutrition 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000007363 ring formation reaction Methods 0.000 description 9
- 230000003595 spectral effect Effects 0.000 description 9
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 8
- 239000002585 base Substances 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229940079593 drug Drugs 0.000 description 7
- 239000003814 drug Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 239000000538 analytical sample Substances 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 239000012298 atmosphere Substances 0.000 description 6
- 239000000284 extract Substances 0.000 description 6
- 210000004623 platelet-rich plasma Anatomy 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 102000008186 Collagen Human genes 0.000 description 5
- 108010035532 Collagen Proteins 0.000 description 5
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 5
- 230000002776 aggregation Effects 0.000 description 5
- 238000004220 aggregation Methods 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- 229920001436 collagen Polymers 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000000338 in vitro Methods 0.000 description 5
- 230000036961 partial effect Effects 0.000 description 5
- 230000000144 pharmacologic effect Effects 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- BINWKEIURMBREF-UHFFFAOYSA-N 1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical class C1=CC=C2N=C(NC(=O)N3)C3=CC2=C1 BINWKEIURMBREF-UHFFFAOYSA-N 0.000 description 4
- AGIWNONRDJEVHH-UHFFFAOYSA-N 2,3-dimethyl-6-nitrobenzaldehyde Chemical compound CC1=CC=C([N+]([O-])=O)C(C=O)=C1C AGIWNONRDJEVHH-UHFFFAOYSA-N 0.000 description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RHYBFKMFHLPQPH-UHFFFAOYSA-N N-methylhydantoin Chemical compound CN1CC(=O)NC1=O RHYBFKMFHLPQPH-UHFFFAOYSA-N 0.000 description 4
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 4
- 210000002837 heart atrium Anatomy 0.000 description 4
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 4
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000002560 therapeutic procedure Methods 0.000 description 4
- HBZVGKAFFVCHLO-UHFFFAOYSA-N (2,3-dimethyl-6-nitrophenyl)methanol Chemical compound CC1=CC=C([N+]([O-])=O)C(CO)=C1C HBZVGKAFFVCHLO-UHFFFAOYSA-N 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 3
- JLADTIPBYWSGLM-UHFFFAOYSA-N 1-nitroimidazolidine-2,4-dione Chemical compound [O-][N+](=O)N1CC(=O)NC1=O JLADTIPBYWSGLM-UHFFFAOYSA-N 0.000 description 3
- GYDRDYBWCJBHKC-UHFFFAOYSA-N 5-[(2-chloro-6-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=CC(Cl)=C1CC1C(=O)NC(=O)N1 GYDRDYBWCJBHKC-UHFFFAOYSA-N 0.000 description 3
- ICQRXJVLDVTQBH-UHFFFAOYSA-N 5-[(5-chloro-4-methyl-2-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound C1=C(Cl)C(C)=CC([N+]([O-])=O)=C1CC1C(=O)NC(=O)N1 ICQRXJVLDVTQBH-UHFFFAOYSA-N 0.000 description 3
- PNQYQNIOVAYJJG-UHFFFAOYSA-N 5-diethoxyphosphorylimidazolidine-2,4-dione Chemical compound CCOP(=O)(OCC)C1NC(=O)NC1=O PNQYQNIOVAYJJG-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 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 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001450 anions Chemical class 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229940082638 cardiac stimulant phosphodiesterase inhibitors Drugs 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 231100000673 dose–response relationship Toxicity 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000003456 ion exchange resin Substances 0.000 description 3
- 229920003303 ion-exchange polymer Polymers 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
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- 238000011160 research Methods 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
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- C—CHEMISTRY; METALLURGY
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- 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
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- 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
- C07D471/02—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 two hetero rings
- C07D471/04—Ortho-condensed systems
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Heart & Thoracic Surgery (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US72686985A | 1985-04-25 | 1985-04-25 | |
| US06/832,212 US4668686A (en) | 1985-04-25 | 1986-02-26 | Imidazoquinoline antithrombrogenic cardiotonic agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CY1641A true CY1641A (en) | 1992-11-06 |
Family
ID=27111398
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CY1641A CY1641A (en) | 1985-04-25 | 1992-11-06 | Imidazoquinoline derivatives |
Country Status (32)
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4775674A (en) * | 1986-05-23 | 1988-10-04 | Bristol-Myers Company | Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors |
| US4701459A (en) * | 1986-07-08 | 1987-10-20 | Bristol-Myers Company | 7-amino-1,3-dihydro-2H-imidazo[4,5-b]quinolin 2-ones and method for inhibiting phosphodiesterase and blood platelet aggregation |
| US4803210A (en) * | 1987-05-29 | 1989-02-07 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic tricyclic oxazolones |
| US4743607A (en) * | 1987-05-29 | 1988-05-10 | Merrell Dow Pharmaceuticals Inc. | Cardiotonic tricyclic imidazolones |
| US4943573A (en) * | 1989-11-01 | 1990-07-24 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyloxyalkanoic acid amides with enhanced water solubility |
| DE4035854C2 (de) * | 1990-11-10 | 1996-10-02 | Daimler Benz Ag | Vorrichtung zum Fangen und Ableiten des von einem Fahrzeugrad hochgeschleuderten Spritzwassers |
| PH31245A (en) * | 1991-10-30 | 1998-06-18 | Janssen Pharmaceutica Nv | 1,3-Dihydro-2H-imidazoÄ4,5-BÜ-quinolin-2-one derivatives. |
| US5196428A (en) * | 1992-04-03 | 1993-03-23 | Bristol-Myers Squibb Company | Imidazo[4,5-b]qinolinyl oxy alkyl ureas |
| US5208237A (en) * | 1992-04-03 | 1993-05-04 | Bristol-Meyers Squibb Company | 7-oxypropylsulfonamido-imidazo[4,5-b]quinolin-2-ones |
| US5158958A (en) * | 1992-04-03 | 1992-10-27 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyl oxy alkyl sulfonyl piperidine derivatives |
| US5552267A (en) * | 1992-04-03 | 1996-09-03 | The Trustees Of Columbia University In The City Of New York | Solution for prolonged organ preservation |
| US5348960A (en) * | 1992-04-03 | 1994-09-20 | Bristol-Myers Squibb Company | Imidazo[4,5-b]quinolinyl oxy alkyl tetrazolyl piperidine derivatives |
| TW593317B (en) * | 1993-06-21 | 2004-06-21 | Janssen Pharmaceutica Nv | Positive cardiac inotropic and lusitropic pyrroloquinolinone derivatives |
| CN1048015C (zh) * | 1993-07-06 | 2000-01-05 | 美国辉瑞有限公司 | 双环四氢吡唑并吡啶类化合物 |
| TW530047B (en) * | 1994-06-08 | 2003-05-01 | Pfizer | Corticotropin releasing factor antagonists |
| US6664264B2 (en) * | 2000-12-08 | 2003-12-16 | 3M Innovative Properties Company | Thioether substituted imidazoquinolines |
| AU2004266641A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Oxime substituted imidazo-containing compounds |
| ES2406730T3 (es) | 2003-08-27 | 2013-06-07 | 3M Innovative Properties Company | Imidazoquinolinas sustituidas con ariloxi y arilalquilenoxi |
| WO2005023190A2 (en) | 2003-09-05 | 2005-03-17 | 3M Innovative Properties Company | Treatment for cd5+ b cell lymphoma |
| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
| SG149828A1 (en) * | 2003-10-03 | 2009-02-27 | 3M Innovative Properties Co | Alkoxy substituted imidazoquinolines |
| JP2007511535A (ja) * | 2003-11-14 | 2007-05-10 | スリーエム イノベイティブ プロパティズ カンパニー | ヒドロキシルアミン置換イミダゾ環化合物 |
| CA2545774A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
| KR101130928B1 (ko) | 2003-11-25 | 2012-04-12 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 치환된 이미다조 고리 시스템 및 방법 |
| JP2007517035A (ja) | 2003-12-29 | 2007-06-28 | スリーエム イノベイティブ プロパティズ カンパニー | アリールアルケニルおよびアリールアルキニル置換されたイミダゾキノリン |
| CA2551399A1 (en) | 2003-12-30 | 2005-07-21 | 3M Innovative Properties Company | Imidazoquinolinyl, imidazopyridinyl, and imidazonaphthyridinyl sulfonamides |
| TW200612932A (en) | 2004-03-24 | 2006-05-01 | 3M Innovative Properties Co | Amide substituted imidazopyridines, imidazoquinolines, and imidazonaphthyridines |
| US8017779B2 (en) | 2004-06-15 | 2011-09-13 | 3M Innovative Properties Company | Nitrogen containing heterocyclyl substituted imidazoquinolines and imidazonaphthyridines |
| US7897609B2 (en) | 2004-06-18 | 2011-03-01 | 3M Innovative Properties Company | Aryl substituted imidazonaphthyridines |
| US8026366B2 (en) | 2004-06-18 | 2011-09-27 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted thiazoloquinolines and thiazolonaphthyridines |
| US7915281B2 (en) | 2004-06-18 | 2011-03-29 | 3M Innovative Properties Company | Isoxazole, dihydroisoxazole, and oxadiazole substituted imidazo ring compounds and method |
| JP4769810B2 (ja) * | 2004-09-14 | 2011-09-07 | ノバルティス ヴァクシンズ アンド ダイアグノスティクス， インコーポレイテッド | イミダゾキノリン化合物 |
| WO2006074003A2 (en) | 2004-12-30 | 2006-07-13 | 3M Innovative Properties Company | CHIRAL FUSED [1,2]IMIDAZO[4,5-c] RING COMPOUNDS |
| CA2594674C (en) | 2004-12-30 | 2016-05-17 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| JP2008530022A (ja) | 2005-02-04 | 2008-08-07 | コーリー ファーマシューティカル グループ，インコーポレイテッド | 免疫反応調節物質を含む水性ゲル処方物 |
| US7968563B2 (en) | 2005-02-11 | 2011-06-28 | 3M Innovative Properties Company | Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods |
| US7943610B2 (en) | 2005-04-01 | 2011-05-17 | 3M Innovative Properties Company | Pyrazolopyridine-1,4-diamines and analogs thereof |
| JP2008538550A (ja) | 2005-04-01 | 2008-10-30 | コーリー ファーマシューティカル グループ，インコーポレイテッド | ウイルス感染および腫瘍性疾患を処置するためのサイトカイン生合成の調節因子としての１−置換ピラゾロ（３，４−ｃ）環状化合物 |
| WO2008008432A2 (en) | 2006-07-12 | 2008-01-17 | Coley Pharmaceutical Group, Inc. | Substituted chiral fused( 1,2) imidazo (4,5-c) ring compounds and methods |
| US8227603B2 (en) | 2006-08-01 | 2012-07-24 | Cytokinetics, Inc. | Modulating skeletal muscle |
| US8299248B2 (en) | 2006-08-02 | 2012-10-30 | Cytokinetics, Incorporated | Certain 1H-imidazo[4,5-b]pyrazin-2(3H)-ones and 1H-imidazo[4,5-b]pyrazin-2-ols and methods for their use |
| DK2583970T3 (en) | 2006-08-02 | 2015-11-16 | Cytokinetics Inc | Certain chemical entities, compositions, and methods comprising imidazopyrimidines |
| WO2008121333A1 (en) * | 2007-03-30 | 2008-10-09 | Cytokinetics, Incorporated | Certain chemical entities, compositions and methods |
| SG10201605707UA (en) | 2011-07-13 | 2016-09-29 | Cytokinetics Inc | Combination als therapy |
| WO2024149378A1 (zh) * | 2023-01-13 | 2024-07-18 | 上海超阳药业有限公司 | 喹啉酮化合物和萘啶酮化合物及其用途 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3932407A (en) * | 1973-11-19 | 1976-01-13 | Bristol-Myers Company | Optionally substituted 1,2,3,5-tetrahydroimidezo(2,1-b)-quinazolin-2-ones and 6(H)-1,2,3,4-tetrahydropyimido(2,1-b)quinazolin-2-ones |
-
1986
- 1986-02-26 US US06/832,212 patent/US4668686A/en not_active Expired - Fee Related
- 1986-03-26 CA CA000505136A patent/CA1298836C/en not_active Expired - Fee Related
- 1986-04-18 NZ NZ215885A patent/NZ215885A/xx unknown
- 1986-04-21 AU AU56413/86A patent/AU592983B2/en not_active Ceased
- 1986-04-22 FI FI861684A patent/FI83316C/fi not_active IP Right Cessation
- 1986-04-22 IL IL78581A patent/IL78581A0/xx not_active IP Right Cessation
- 1986-04-23 EG EG237/86A patent/EG18104A/xx active
- 1986-04-23 CN CN86102747A patent/CN1016175B/zh not_active Expired
- 1986-04-24 GR GR861086A patent/GR861086B/el unknown
- 1986-04-24 LU LU86406A patent/LU86406A1/fr unknown
- 1986-04-24 DK DK190986A patent/DK164868C/da not_active IP Right Cessation
- 1986-04-24 SE SE8601907A patent/SE461468B/sv not_active IP Right Cessation
- 1986-04-24 BE BE0/216585A patent/BE904671A/fr not_active IP Right Cessation
- 1986-04-24 IT IT8620206A patent/IT1215651B/it active
- 1986-04-24 FR FR868605966A patent/FR2581065B1/fr not_active Expired - Fee Related
- 1986-04-24 ES ES554336A patent/ES8708229A1/es not_active Expired
- 1986-04-24 SU SU864027355A patent/SU1450746A3/ru active
- 1986-04-24 PT PT82460A patent/PT82460B/pt not_active IP Right Cessation
- 1986-04-24 NL NL8601053A patent/NL8601053A/xx not_active Application Discontinuation
- 1986-04-24 NO NO861617A patent/NO163406C/no unknown
- 1986-04-24 GB GB8610037A patent/GB2174987B/en not_active Expired
- 1986-04-24 CH CH1679/86A patent/CH675722A5/de not_active IP Right Cessation
- 1986-04-25 AT AT0112186A patent/AT390257B/de not_active IP Right Cessation
- 1986-04-25 KR KR1019860003204A patent/KR940000828B1/ko not_active Expired - Lifetime
- 1986-04-25 OA OA58845A patent/OA08242A/xx unknown
- 1986-04-25 HU HU861723A patent/HU195813B/hu not_active IP Right Cessation
- 1986-04-25 DE DE19863614132 patent/DE3614132A1/de not_active Ceased
-
1987
- 1987-02-27 SU SU874202071A patent/SU1470192A3/ru active
- 1987-05-14 ES ES557552A patent/ES8802521A1/es not_active Expired
- 1987-05-14 ES ES557551A patent/ES8801829A1/es not_active Expired
- 1987-06-23 YU YU116787A patent/YU46054B/sh unknown
- 1987-09-25 SU SU874203391A patent/SU1560056A3/ru active
- 1987-09-29 MY MYPI87002266A patent/MY102086A/en unknown
-
1991
- 1991-04-30 DK DK080291A patent/DK165248C/da not_active IP Right Cessation
- 1991-05-01 DK DK081091A patent/DK165249C/da not_active IP Right Cessation
-
1992
- 1992-03-10 SG SG290/92A patent/SG29092G/en unknown
- 1992-08-27 HK HK644/92A patent/HK64492A/xx unknown
- 1992-11-06 CY CY1641A patent/CY1641A/en unknown
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