CY1641A - Imidazoquinoline derivatives - Google Patents

Imidazoquinoline derivatives Download PDF

Info

Publication number: CY1641A
Authority: CY; Cyprus
Prior art keywords: compound; imidazo; dihydro; quinolin; formula
Prior art date: 1985-04-25

Application number

CY1641A

Other languages

English (en)

Original Assignee

Bristol Myers Squibb Co

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

1985-04-25

Filing date

1992-11-06

Publication date

1992-11-06

1992-11-06 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1992-11-06 Publication of CY1641A publication Critical patent/CY1641A/en

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
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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
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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
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238000007796 conventional method Methods 0.000 description 3
231100000673 dose–response relationship Toxicity 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
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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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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
FGFRGLZXPZOXAI-UHFFFAOYSA-N (2,3-dimethyl-6-nitrophenyl)methanamine Chemical compound CC1=CC=C([N+]([O-])=O)C(CN)=C1C FGFRGLZXPZOXAI-UHFFFAOYSA-N 0.000 description 2
NYNBIZMIFBGAJF-UHFFFAOYSA-N (2,5-dioxoimidazolidin-4-yl)phosphonic acid Chemical compound OP(O)(=O)C1NC(=O)NC1=O NYNBIZMIFBGAJF-UHFFFAOYSA-N 0.000 description 2
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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
- 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
- A—HUMAN NECESSITIES
- 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)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Veterinary Medicine (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Hematology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

CY1641A 1985-04-25 1992-11-06 Imidazoquinoline derivatives CY1641A (en)

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)

Country	Link
US (1)	US4668686A (de)
KR (1)	KR940000828B1 (de)
CN (1)	CN1016175B (de)
AT (1)	AT390257B (de)
AU (1)	AU592983B2 (de)
BE (1)	BE904671A (de)
CA (1)	CA1298836C (de)
CH (1)	CH675722A5 (de)
CY (1)	CY1641A (de)
DE (1)	DE3614132A1 (de)
DK (3)	DK164868C (de)
EG (1)	EG18104A (de)
ES (3)	ES8708229A1 (de)
FI (1)	FI83316C (de)
FR (1)	FR2581065B1 (de)
GB (1)	GB2174987B (de)
GR (1)	GR861086B (de)
HK (1)	HK64492A (de)
HU (1)	HU195813B (de)
IL (1)	IL78581A0 (de)
IT (1)	IT1215651B (de)
LU (1)	LU86406A1 (de)
MY (1)	MY102086A (de)
NL (1)	NL8601053A (de)
NO (1)	NO163406C (de)
NZ (1)	NZ215885A (de)
OA (1)	OA08242A (de)
PT (1)	PT82460B (de)
SE (1)	SE461468B (de)
SG (1)	SG29092G (de)
SU (3)	SU1450746A3 (de)
YU (1)	YU46054B (de)

Families Citing this family (45)

* Cited by examiner, † Cited by third party
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.
US5158958A (en) *	1992-04-03	1992-10-27	Bristol-Myers Squibb Company	Imidazo[4,5-b]quinolinyl oxy alkyl sulfonyl piperidine derivatives
US5196428A (en) *	1992-04-03	1993-03-23	Bristol-Myers Squibb Company	Imidazo[4,5-b]qinolinyl oxy alkyl ureas
US5348960A (en) *	1992-04-03	1994-09-20	Bristol-Myers Squibb Company	Imidazo[4,5-b]quinolinyl oxy alkyl tetrazolyl 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
US5208237A (en) *	1992-04-03	1993-05-04	Bristol-Meyers Squibb Company	7-oxypropylsulfonamido-imidazo[4,5-b]quinolin-2-ones
TW593317B (en) *	1993-06-21	2004-06-21	Janssen Pharmaceutica Nv	Positive cardiac inotropic and lusitropic pyrroloquinolinone derivatives
RU2131876C1 (ru) *	1993-07-06	1999-06-20	Пфайзер Инк.	Бициклические тетрагидропиразолпиридины или их фармацевтически приемлемые соли, фармацевтическая композиция, способ ингибирования фосфодиэстеразы, способ лечения
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
BRPI0413558A (pt)	2003-08-12	2006-10-17	3M Innovative Properties Co	compostos contendo imidazo substituìdo por hidroxilamina
MXPA06002199A (es)	2003-08-27	2006-05-22	3M Innovative Properties Co	Imidazoquinolinas sustituidas con grupos ariloxi o arilalquilenoxi.
CA2537763A1 (en)	2003-09-05	2005-03-17	3M Innovative Properties Company	Treatment for cd5+ b cell lymphoma
CA2540541C (en) *	2003-10-03	2012-03-27	3M Innovative Properties Company	Alkoxy substituted imidazoquinolines
US7544697B2 (en)	2003-10-03	2009-06-09	Coley Pharmaceutical Group, Inc.	Pyrazolopyridines and analogs thereof
WO2005048945A2 (en) *	2003-11-14	2005-06-02	3M Innovative Properties Company	Hydroxylamine substituted imidazo ring compounds
US7897767B2 (en)	2003-11-14	2011-03-01	3M Innovative Properties Company	Oxime substituted imidazoquinolines
WO2005051317A2 (en)	2003-11-25	2005-06-09	3M Innovative Properties Company	Substituted imidazo ring systems and methods
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
EP1699788A2 (de)	2003-12-30	2006-09-13	3M Innovative Properties Company	Imidazochinolinyl-, imidazopyridinyl- und imidazonaphthyridinylsulfonamide
WO2005094531A2 (en)	2004-03-24	2005-10-13	3M Innovative Properties Company	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
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
US7897609B2 (en)	2004-06-18	2011-03-01	3M Innovative Properties Company	Aryl substituted imidazonaphthyridines
US20080213308A1 (en) *	2004-09-14	2008-09-04	Nicholas Valiante	Imidazoquinoline Compounds
AU2005326708C1 (en)	2004-12-30	2012-08-30	3M Innovative Properties Company	Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds
JP5543068B2 (ja)	2004-12-30	2014-07-09	スリーエムイノベイティブプロパティズカンパニー	キラル縮合［１，２］イミダゾ［４，５−ｃ］環状化合物
WO2006084251A2 (en)	2005-02-04	2006-08-10	Coley Pharmaceutical Group, Inc.	Aqueous gel formulations containing immune reponse modifiers
CA2597587A1 (en)	2005-02-11	2006-08-17	Coley Pharmaceutical Group, Inc.	Oxime and hydroxylamine substituted imidazo[4,5-c] ring compounds and methods
JP2008535832A (ja)	2005-04-01	2008-09-04	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	ピラゾロピリジン−１，４−ジアミン、およびそのアナログ
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
US7906506B2 (en)	2006-07-12	2011-03-15	3M Innovative Properties Company	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
ES2558517T3 (es)	2006-08-02	2016-02-04	Cytokinetics, Inc.	Ciertas entidades químicas, composiciones y métodos que comprenden imidazopirimidinas
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
WO2008121333A1 (en) *	2007-03-30	2008-10-09	Cytokinetics, Incorporated	Certain chemical entities, compositions and methods
KR101951220B1 (ko)	2011-07-13	2019-02-22	싸이토키네틱스, 인코포레이티드	조합 als 치료법
CN120265631A (zh) *	2023-01-13	2025-07-04	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)

* Cited by examiner, † Cited by third party
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 IL IL78581A patent/IL78581A0/xx not_active IP Right Cessation
- 1986-04-22 FI FI861684A patent/FI83316C/fi not_active IP Right Cessation
- 1986-04-23 CN CN86102747A patent/CN1016175B/zh not_active Expired
- 1986-04-23 EG EG237/86A patent/EG18104A/xx active
- 1986-04-24 CH CH1679/86A patent/CH675722A5/de not_active IP Right Cessation
- 1986-04-24 GB GB8610037A patent/GB2174987B/en not_active Expired
- 1986-04-24 DK DK190986A patent/DK164868C/da not_active IP Right Cessation
- 1986-04-24 ES ES554336A patent/ES8708229A1/es not_active Expired
- 1986-04-24 GR GR861086A patent/GR861086B/el unknown
- 1986-04-24 NO NO861617A patent/NO163406C/no unknown
- 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 FR FR868605966A patent/FR2581065B1/fr not_active Expired - Fee Related
- 1986-04-24 IT IT8620206A patent/IT1215651B/it active
- 1986-04-24 LU LU86406A patent/LU86406A1/fr unknown
- 1986-04-24 BE BE0/216585A patent/BE904671A/fr not_active IP Right Cessation
- 1986-04-24 SU SU864027355A patent/SU1450746A3/ru active
- 1986-04-24 SE SE8601907A patent/SE461468B/sv not_active IP Right Cessation
- 1986-04-25 DE DE19863614132 patent/DE3614132A1/de not_active Ceased
- 1986-04-25 OA OA58845A patent/OA08242A/xx unknown
- 1986-04-25 KR KR1019860003204A patent/KR940000828B1/ko not_active Expired - Lifetime
- 1986-04-25 AT AT0112186A patent/AT390257B/de not_active IP Right Cessation
- 1986-04-25 HU HU861723A patent/HU195813B/hu not_active IP Right Cessation
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

Also Published As

Publication number	Publication date
ES557552A0 (es)	1988-07-16
SE8601907L (sv)	1986-10-26
DK165248C (da)	1993-03-22
DK81091A (da)	1991-05-01
DK190986D0 (da)	1986-04-24
GR861086B (en)	1986-09-01
NO163406B (no)	1990-02-12
DK164868B (da)	1992-08-31
FR2581065A1 (fr)	1986-10-31
GB2174987A (en)	1986-11-19
AT390257B (de)	1990-04-10
KR860008177A (ko)	1986-11-12
FI83316C (fi)	1991-06-25
AU592983B2 (en)	1990-02-01
GB2174987B (en)	1989-08-02
ES8801829A1 (es)	1988-02-16
HK64492A (en)	1992-09-04
FI861684L (fi)	1986-10-26
MY102086A (en)	1992-03-31
CH675722A5 (de)	1990-10-31
YU116787A (en)	1988-04-30
SE461468B (sv)	1990-02-19
SG29092G (en)	1992-05-15
NL8601053A (nl)	1986-11-17
CN1016175B (zh)	1992-04-08
FI83316B (fi)	1991-03-15
DK81091D0 (da)	1991-05-01
ES8708229A1 (es)	1987-10-01
EG18104A (en)	1992-09-30
ES557551A0 (es)	1988-02-16
DK80291A (da)	1991-04-30
LU86406A1 (fr)	1986-11-05
BE904671A (fr)	1986-10-24
NO163406C (no)	1990-05-23
NO861617L (no)	1986-10-27
KR940000828B1 (ko)	1994-02-02
NZ215885A (en)	1989-04-26
OA08242A (en)	1987-10-30
DK190986A (da)	1986-10-26
HUT42089A (en)	1987-06-29
FI861684A0 (fi)	1986-04-22
CN86102747A (zh)	1987-02-04
PT82460A (en)	1986-05-01
DK165249C (da)	1993-03-22
AU5641386A (en)	1986-10-30
DK164868C (da)	1993-01-11
SU1470192A3 (ru)	1989-03-30
IT8620206A0 (it)	1986-04-24
YU46054B (sh)	1992-12-21
IT1215651B (it)	1990-02-22
PT82460B (pt)	1988-11-30
ATA112186A (de)	1989-09-15
SU1560056A3 (ru)	1990-04-23
CA1298836C (en)	1992-04-14
DK165248B (da)	1992-10-26
FR2581065B1 (fr)	1990-02-02
HU195813B (en)	1988-07-28
SU1450746A3 (ru)	1989-01-07
DK165249B (da)	1992-10-26
DK80291D0 (da)	1991-04-30
SE8601907D0 (sv)	1986-04-24
DE3614132A1 (de)	1986-11-27
US4668686A (en)	1987-05-26
GB8610037D0 (en)	1986-05-29
ES8802521A1 (es)	1988-07-16
ES554336A0 (es)	1987-10-01
IL78581A0 (en)	1986-08-31

Publication	Publication Date	Title
CY1641A (en)	1992-11-06	Imidazoquinoline derivatives
AU603577B2 (en)	1990-11-22	Imidazoquinolinylether derivatives
CA1309095C (en)	1992-10-20	Aminoimidazoquinoline derivatives
US4663326A (en)	1987-05-05	Pyrazolo[4,3-d]pyrimidine-5,7-(4H,6H)dione or -5-thione-7-one analogs
US4786645A (en)	1988-11-22	1H, 3H-pyrrolo (1,2-C) thiazole derivatives and pharmaceutical compositions
GB2177393A (en)	1987-01-21	Benzimidazole derivatives
PT90907B (pt)	1994-12-30	Processo para a preparacao de novas 4,5,7,8-tetra-hidro-6h-tiazolo {5,4-d} azepinas e de composicoes farmaceuticas que as contem
EP0594883B1 (de)	1999-01-27	Imidazo(1,2-c)chinazolinderivate als antihypertensive und antidysurie
CS248020B2 (en)	1987-01-15	Production method of the (+)-enantiomere or (+-)-racemical 4a,9b-trans-hexahydro-1h-pyridoindole derivatives
IE883136L (en)	1989-05-19	Ó(2)-adreno receptor antagonists
EP0462986B1 (de)	1993-10-06	Imidazopyrimidine, antiallergische heilmittel
JPS6284A (ja)	1987-01-06	イミダゾキノリン抗血栓性強心薬
JP3709203B2 (ja)	2005-10-26	５−ｈｔ１ａレセプターに対して親和性をもつ三環式化合物
JPH10505330A (ja)	1998-05-26	ハロゲンイミダゾピリジン
NO893611L (no)	1986-10-27	Fremstilling av imidazokinolinonderivater.
WO1992012979A1 (en)	1992-08-06	2,4-DIOXO-PYRIDO [2,3-d]PYRIMIDINE-3-ACETIC ACIDS AND ESTERS AND SALTS THEREOF
HU191670B (en)	1987-03-30	Process for production of 1-phenoxi-3-/hydroxi-indolil-alkyl-amino/-2-propanols and medical preparatives containing thereof as active substance
JPH04503944A (ja)	1992-07-16	ピリダジノン―、ピラゾロン―及びピリドン―ナフテリジノン化合物、それらを含む強心薬組成物、及びそれらの使用