AT390257B - Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate - Google Patents

Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate Download PDF

Info

Publication number: AT390257B
Authority: AT; Austria
Prior art keywords: formula; methyl; imidazolidinedione; nitrophenyl; starting compound
Prior art date: 1985-04-25

Application number

AT0112186A

Other languages

German (de)

English (en)

Other versions

ATA112186A (de

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

1986-04-25

Publication date

1990-04-10

1986-04-25 Application filed by Bristol Myers Squibb Co filed Critical Bristol Myers Squibb Co

1989-07-12 Priority to AT0168989A priority Critical patent/AT390953B/de

1989-09-15 Publication of ATA112186A publication Critical patent/ATA112186A/de

1990-04-10 Application granted granted Critical

1990-04-10 Publication of AT390257B publication Critical patent/AT390257B/de

Links

238000004519 manufacturing process Methods 0.000 title description 3
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical class N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title 1
238000000034 method Methods 0.000 claims description 107
150000001875 compounds Chemical class 0.000 claims description 88
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 81
229910052739 hydrogen Inorganic materials 0.000 claims description 41
239000001257 hydrogen Substances 0.000 claims description 38
-1 thio compound Chemical class 0.000 claims description 30
239000007858 starting material Substances 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 24
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
230000008569 process Effects 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 16
150000002367 halogens Chemical group 0.000 claims description 16
229940091173 hydantoin Drugs 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 13
150000001469 hydantoins Chemical class 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 10
150000002431 hydrogen Chemical group 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
239000000463 material Substances 0.000 claims description 6
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 6
239000000460 chlorine Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 4
229910019142 PO4 Inorganic materials 0.000 claims description 4
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
239000010452 phosphate Substances 0.000 claims description 4
IDVVDXHDDWLPFQ-UHFFFAOYSA-N 5-[(2-chloro-3-methyl-6-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound CC1=CC=C([N+]([O-])=O)C(CC2C(NC(=O)N2)=O)=C1Cl IDVVDXHDDWLPFQ-UHFFFAOYSA-N 0.000 claims description 3
RMDXKBUERRXWDD-UHFFFAOYSA-N 5-[(2-methyl-6-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound CC1=CC=CC([N+]([O-])=O)=C1CC1C(=O)NC(=O)N1 RMDXKBUERRXWDD-UHFFFAOYSA-N 0.000 claims description 3
RYQMWRNCEHFJKV-UHFFFAOYSA-N 5-[(5-chloro-2-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=C(Cl)C=C1CC1C(=O)NC(=O)N1 RYQMWRNCEHFJKV-UHFFFAOYSA-N 0.000 claims description 3
FOBQFDVPYJEMFC-UHFFFAOYSA-N 5-[(5-methoxy-2-nitrophenyl)methylidene]-1-methylimidazolidine-2,4-dione Chemical compound COC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2C)=O)=C1 FOBQFDVPYJEMFC-UHFFFAOYSA-N 0.000 claims description 3
MLWIJCWUUBZBHZ-UHFFFAOYSA-N 5-[(5-methyl-2-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound CC1=CC=C([N+]([O-])=O)C(CC2C(NC(=O)N2)=O)=C1 MLWIJCWUUBZBHZ-UHFFFAOYSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
GIMXBORKCIXLDB-UHFFFAOYSA-N 1h-imidazo[4,5-b]quinoline Chemical class C1=CC=C2NC3=NC=NC3=CC2=C1 GIMXBORKCIXLDB-UHFFFAOYSA-N 0.000 claims description 2
OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims description 2
FHHWJBYTBSEZHE-UHFFFAOYSA-N 2-methylsulfanyl-6-(trifluoromethyl)-1h-imidazo[4,5-b]quinoline Chemical compound FC(F)(F)C1=CC=C2C=C(NC(SC)=N3)C3=NC2=C1 FHHWJBYTBSEZHE-UHFFFAOYSA-N 0.000 claims description 2
TXSUREPGYUVQEM-UHFFFAOYSA-N 5-[(2,3-dimethyl-6-nitrophenyl)methylidene]-1-methylimidazolidine-2,4-dione Chemical compound CN1C(=O)NC(=O)C1=CC1=C(C)C(C)=CC=C1[N+]([O-])=O TXSUREPGYUVQEM-UHFFFAOYSA-N 0.000 claims description 2
HOEUDOHXWFWZPR-UHFFFAOYSA-N 5-[(2-methoxy-6-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound COC1=CC=CC([N+]([O-])=O)=C1CC1C(=O)NC(=O)N1 HOEUDOHXWFWZPR-UHFFFAOYSA-N 0.000 claims description 2
DBTBDZTWXIAUEG-UHFFFAOYSA-N 5-[(3-chloro-2,4-dimethyl-6-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound CC1=C(Cl)C(C)=CC([N+]([O-])=O)=C1CC1C(=O)NC(=O)N1 DBTBDZTWXIAUEG-UHFFFAOYSA-N 0.000 claims description 2
INXCDAYOONISFV-UHFFFAOYSA-N 5-[(4,5-dimethoxy-2-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound C1=C(OC)C(OC)=CC(CC2C(NC(=O)N2)=O)=C1[N+]([O-])=O INXCDAYOONISFV-UHFFFAOYSA-N 0.000 claims description 2
UHBKAIMRBMARAT-UHFFFAOYSA-N 5-[(4,5-dimethyl-2-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound C1=C(C)C(C)=CC(CC2C(NC(=O)N2)=O)=C1[N+]([O-])=O UHBKAIMRBMARAT-UHFFFAOYSA-N 0.000 claims description 2
VJPJCHSSLUOZEG-UHFFFAOYSA-N 5-[(5-fluoro-2-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound [O-][N+](=O)C1=CC=C(F)C=C1CC1C(=O)NC(=O)N1 VJPJCHSSLUOZEG-UHFFFAOYSA-N 0.000 claims description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 2
XESDVFPKKYJMMA-UHFFFAOYSA-N 5-[(2,3,4-trimethoxy-6-nitrophenyl)methylidene]imidazolidine-2,4-dione Chemical compound COC1=C(OC)C(OC)=CC([N+]([O-])=O)=C1C=C1C(=O)NC(=O)N1 XESDVFPKKYJMMA-UHFFFAOYSA-N 0.000 claims 1
PZETVVICLLGENE-UHFFFAOYSA-N 5-[(2-amino-5-bromophenyl)methyl]imidazolidine-2,4-dione Chemical compound NC1=CC=C(Br)C=C1CC1C(=O)NC(=O)N1 PZETVVICLLGENE-UHFFFAOYSA-N 0.000 claims 1
AITDMZBNNPYQNY-UHFFFAOYSA-N 5-[(2-amino-6-methylphenyl)methyl]-1-methylimidazolidine-2,4-dione Chemical compound O=C1NC(=O)N(C)C1CC1=C(C)C=CC=C1N AITDMZBNNPYQNY-UHFFFAOYSA-N 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 126
229910001868 water Inorganic materials 0.000 description 93
239000000203 mixture Substances 0.000 description 76
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 67
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 61
239000000243 solution Substances 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 47
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 39
239000007787 solid Substances 0.000 description 35
239000002904 solvent Substances 0.000 description 35
125000003118 aryl group Chemical group 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 30
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 27
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 26
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 26
239000000543 intermediate Substances 0.000 description 25
238000010992 reflux Methods 0.000 description 24
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 16
229910000041 hydrogen chloride Inorganic materials 0.000 description 16
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 15
230000000694 effects Effects 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 13
238000009835 boiling Methods 0.000 description 13
239000011630 iodine Substances 0.000 description 13
229910052740 iodine Inorganic materials 0.000 description 13
238000002844 melting Methods 0.000 description 13
230000008018 melting Effects 0.000 description 13
229910000029 sodium carbonate Inorganic materials 0.000 description 13
238000012360 testing method Methods 0.000 description 13
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
210000001772 blood platelet Anatomy 0.000 description 12
230000005764 inhibitory process Effects 0.000 description 12
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 12
208000010110 spontaneous platelet aggregation Diseases 0.000 description 12
239000000126 substance Substances 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 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
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 description 9
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 description 9
229960000583 acetic acid Drugs 0.000 description 9
239000000047 product Substances 0.000 description 9
230000003595 spectral effect Effects 0.000 description 9
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 8
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 8
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 8
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
239000002253 acid Substances 0.000 description 8
238000002425 crystallisation Methods 0.000 description 8
230000008025 crystallization Effects 0.000 description 8
238000002474 experimental method Methods 0.000 description 8
238000011282 treatment Methods 0.000 description 8
239000000538 analytical sample Substances 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
238000001914 filtration Methods 0.000 description 7
238000000338 in vitro Methods 0.000 description 7
238000001802 infusion Methods 0.000 description 7
210000004623 platelet-rich plasma Anatomy 0.000 description 7
LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 description 7
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 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
241000124008 Mammalia Species 0.000 description 6
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000000284 extract Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000000725 suspension Substances 0.000 description 6
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102000008186 Collagen Human genes 0.000 description 5
108010035532 Collagen Proteins 0.000 description 5
208000007536 Thrombosis Diseases 0.000 description 5
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239000004480 active ingredient Substances 0.000 description 5
239000012300 argon atmosphere Substances 0.000 description 5
210000001367 artery Anatomy 0.000 description 5
239000002585 base Substances 0.000 description 5
229920001436 collagen Polymers 0.000 description 5
239000003814 drug Substances 0.000 description 5
DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 5
238000003756 stirring Methods 0.000 description 5
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 4
KBOROMLUUMZHDJ-UHFFFAOYSA-N 5-[(5-methoxy-2-nitrophenyl)methylidene]imidazolidine-2,4-dione Chemical compound COC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=C1 KBOROMLUUMZHDJ-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
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
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 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
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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
230000008602 contraction Effects 0.000 description 4
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
230000000297 inotrophic effect Effects 0.000 description 4
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 4
UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 4
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 4
230000009467 reduction Effects 0.000 description 4
230000004044 response Effects 0.000 description 4
238000007363 ring formation reaction Methods 0.000 description 4
239000011734 sodium Substances 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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 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
KVYKDNGUEZRPGJ-UHFFFAOYSA-N 1-Aminohydantoin Chemical compound NN1CC(=O)NC1=O KVYKDNGUEZRPGJ-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
LBHWNZFYCKTRFN-UHFFFAOYSA-N 2-methyl-6-nitrobenzaldehyde Chemical compound CC1=CC=CC([N+]([O-])=O)=C1C=O LBHWNZFYCKTRFN-UHFFFAOYSA-N 0.000 description 3
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 3
YKTRUMDBBHMCIM-UHFFFAOYSA-N 5-[(2,3-dimethyl-6-nitrophenyl)methyl]imidazolidine-2,4-dione Chemical compound CC1=CC=C([N+]([O-])=O)C(CC2C(NC(=O)N2)=O)=C1C YKTRUMDBBHMCIM-UHFFFAOYSA-N 0.000 description 3
XHSCTCAIAUBTGK-UHFFFAOYSA-N 5-[(2,3-dimethyl-6-nitrophenyl)methylidene]imidazolidine-2,4-dione Chemical compound CC1=CC=C([N+]([O-])=O)C(C=C2C(NC(=O)N2)=O)=C1C XHSCTCAIAUBTGK-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
PNQYQNIOVAYJJG-UHFFFAOYSA-N 5-diethoxyphosphorylimidazolidine-2,4-dione Chemical compound CCOP(=O)(OCC)C1NC(=O)NC1=O PNQYQNIOVAYJJG-UHFFFAOYSA-N 0.000 description 3
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
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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)
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Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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AT0112186A 1985-04-25 1986-04-25 Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate AT390257B (de)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
AT0168989A AT390953B (de)	1986-02-26	1989-07-12	Verfahren zur herstellung neuer imidazo(4,5-b) chinolin-2-thione

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 (2)

Publication Number	Publication Date
ATA112186A ATA112186A (de)	1989-09-15
AT390257B true AT390257B (de)	1990-04-10

Family

ID=27111398

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
AT0112186A AT390257B (de)	1985-04-25	1986-04-25	Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate

Country Status (32)

Country	Link
US (1)	US4668686A (2)
KR (1)	KR940000828B1 (2)
CN (1)	CN1016175B (2)
AT (1)	AT390257B (2)
AU (1)	AU592983B2 (2)
BE (1)	BE904671A (2)
CA (1)	CA1298836C (2)
CH (1)	CH675722A5 (2)
CY (1)	CY1641A (2)
DE (1)	DE3614132A1 (2)
DK (3)	DK164868C (2)
EG (1)	EG18104A (2)
ES (3)	ES8708229A1 (2)
FI (1)	FI83316C (2)
FR (1)	FR2581065B1 (2)
GB (1)	GB2174987B (2)
GR (1)	GR861086B (2)
HK (1)	HK64492A (2)
HU (1)	HU195813B (2)
IL (1)	IL78581A0 (2)
IT (1)	IT1215651B (2)
LU (1)	LU86406A1 (2)
MY (1)	MY102086A (2)
NL (1)	NL8601053A (2)
NO (1)	NO163406C (2)
NZ (1)	NZ215885A (2)
OA (1)	OA08242A (2)
PT (1)	PT82460B (2)
SE (1)	SE461468B (2)
SG (1)	SG29092G (2)
SU (3)	SU1450746A3 (2)
YU (1)	YU46054B (2)

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RU2131876C1 (ru) *	1993-07-06	1999-06-20	Пфайзер Инк.	Бициклические тетрагидропиразолпиридины или их фармацевтически приемлемые соли, фармацевтическая композиция, способ ингибирования фосфодиэстеразы, способ лечения
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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
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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 (en)	2003-12-30	2006-09-13	3M Innovative Properties Company	Imidazoquinolinyl, imidazopyridinyl and imidazonaphthyridinyl sulfonamides
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
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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

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Title
CHEMICAL ABSTRACTS 102, 132000 J *

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
CY1641A (en)	1992-11-06
NO163406B (no)	1990-02-12
DK164868B (da)	1992-08-31
FR2581065A1 (fr)	1986-10-31
GB2174987A (en)	1986-11-19
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 (2)	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

Legal Events

Date	Code	Title
1990-04-15	EIH	Change in the person of patent owner
1995-06-15	ELJ	Ceased due to non-payment of the annual fee
1997-04-15	REN	Ceased due to non-payment of the annual fee

Publication	Publication Date	Title
AT390257B (de)	1990-04-10	Verfahren zur herstellung neuer imidazo(4,5-b)chinolin-derivate
AT392790B (de)	1991-06-10	Verfahren zur herstellung von neuen 2,3-dihydro-2-oxo-1h-imidazo-(4,5-b)-chinolinyletherderivaten und den pharmazeutisch vertraeglichen salzen davon
DE69530989T2 (de)	2004-05-19	Neue pyrimidinderivate und verfahren zu ihrer herstellung
DE69426422T2 (de)	2001-05-10	Pyridazino-chinolin verbindungen
EP0736532B1 (de)	2002-05-15	Pyrido(3,2-e)pyrazinone mit antiasthmatischer Wirksamkeit und Verfahren zu deren Herstellung
DE69524114T2 (de)	2002-07-18	Naphthyridinonderivate
DE3782687T2 (de)	1993-04-01	Aminoimidazochinolin-derivate.
EP0528922B1 (de)	1999-06-16	Neue sulfonylverbindungen
DE2854115C2 (2)	1988-07-28
DE69013750T2 (de)	1995-05-24	Antagonisten von excitatorischen Aminosäuren.
CH639662A5 (de)	1983-11-30	Imidazoazine und imidazodiazine.
DE3533331A1 (de)	1987-03-26	Pyridothiazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
EP0058341A1 (de)	1982-08-25	Azepinderivate, ihre Herstellung und diese enthaltende Arzneimittel
CH621552A5 (2)	1981-02-13
DE2914258C2 (2)	1989-08-03
EP0073060A1 (de)	1983-03-02	Neue Imidazochinazolinderivate, ihre Herstellung und diese Derivate enthaltende Arzneimittel
EP0621037B1 (de)	1999-07-07	Pyrido-pyrimidindione, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel
EP0180834A1 (de)	1986-05-14	4-Alkoxy-pyrido[2,3-d]pyrimidin-Derivate, Verfahren zu deren Herstellung und diese enthaltende Arzneimittel
EP0124893A2 (de)	1984-11-14	Neue Pyrimidonderivate
DE2647041C2 (de)	1982-07-01	3-Aminomethylen-6,7-dimethoxy-2- methyl-4-oxo-1,2,3,4-tetrahydro-1-chinolincarbonsäureäthylester
DE2841126A1 (de)	1979-04-05	Pyrimido eckige klammer auf 2,1-a eckige klammer zu isochinolinderivate, verfahren zu ihrer herstellung und pharmazeutische mittel, die diese verbindungen enthalten
EP0089528B1 (de)	1987-05-27	6-Aryl-4,5-dihydro-3(2H)-pyridazinone,ihre Herstellung und Verwendung
EP0180833B1 (de)	1989-07-19	4-Oxo-pyrido[2,3]pyrimidin-Derivate, Verfahren zur deren Herstellung und diese ethaltende Arzneimittel
DE3346640A1 (de)	1985-07-04	Neue imidazolderivate, deren herstellung und diese verbindungen enthaltende arzneimittel
CH634069A5 (en)	1983-01-14	Process for preparing novel 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines