LU86896A1 - Composes derives de l'imidazoquinolinylether,et leur procede de preparation - Google Patents

Composes derives de l'imidazoquinolinylether,et leur procede de preparation Download PDF

Info

Publication number: LU86896A1
Authority: LU; Luxembourg
Prior art keywords: compound; quinolin; imidazo; pharmaceutically acceptable; acceptable salt
Prior art date: 1986-05-23

Application number

LU86896A

Other languages

English (en)

French (fr)

Original Assignee

Bristol Myers 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.)

1986-05-23

Filing date

1987-05-22

Publication date

1988-01-20

1987-05-22 Application filed by Bristol Myers Co filed Critical Bristol Myers Co

1988-01-20 Publication of LU86896A1 publication Critical patent/LU86896A1/fr

Links

150000001875 compounds Chemical class 0.000 title claims description 301
238000000034 method Methods 0.000 title claims description 103
230000008569 process Effects 0.000 title claims description 31
238000002360 preparation method Methods 0.000 title description 12
MOJBIJPADSWXCM-UHFFFAOYSA-N 2-(3h-imidazo[4,5-h]quinolin-2-yloxy)-3h-imidazo[4,5-h]quinoline Chemical compound C1=CC=NC2=C(NC(OC=3NC4=C5N=CC=CC5=CC=C4N=3)=N3)C3=CC=C21 MOJBIJPADSWXCM-UHFFFAOYSA-N 0.000 title description 4
-1 adamantanamyl Chemical group 0.000 claims description 195
150000003839 salts Chemical class 0.000 claims description 113
125000000217 alkyl group Chemical group 0.000 claims description 78
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 70
239000002253 acid Substances 0.000 claims description 68
125000004432 carbon atom Chemical group C* 0.000 claims description 49
229910052739 hydrogen Inorganic materials 0.000 claims description 45
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 42
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
239000001257 hydrogen Substances 0.000 claims description 33
125000003545 alkoxy group Chemical group 0.000 claims description 28
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 24
150000002148 esters Chemical class 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 19
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
229910052736 halogen Inorganic materials 0.000 claims description 17
150000002367 halogens Chemical group 0.000 claims description 17
229940091173 hydantoin Drugs 0.000 claims description 16
NQPDZGIKBAWPEJ-UHFFFAOYSA-N pentanoic acid group Chemical group C(CCCC)(=O)O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 16
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims description 14
239000000463 material Substances 0.000 claims description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 12
FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 12
108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 12
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
125000002947 alkylene group Chemical group 0.000 claims description 11
210000001772 blood platelet Anatomy 0.000 claims description 11
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
IPWFJLQDVFKJDU-UHFFFAOYSA-N pentanamide Chemical compound CCCCC(N)=O IPWFJLQDVFKJDU-UHFFFAOYSA-N 0.000 claims description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 9
150000001469 hydantoins Chemical class 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
241000124008 Mammalia Species 0.000 claims description 8
230000002776 aggregation Effects 0.000 claims description 8
238000004220 aggregation Methods 0.000 claims description 8
150000001408 amides Chemical class 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
150000002576 ketones Chemical class 0.000 claims description 8
230000002401 inhibitory effect Effects 0.000 claims description 6
125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 6
230000002829 reductive effect Effects 0.000 claims description 6
FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical group CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 5
125000001137 3-hydroxypropoxy group Chemical group [H]OC([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 5
241001465754 Metazoa Species 0.000 claims description 5
230000000297 inotrophic effect Effects 0.000 claims description 5
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical group CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
239000007800 oxidant agent Substances 0.000 claims description 4
230000001590 oxidative effect Effects 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
150000001414 amino alcohols Chemical class 0.000 claims description 3
NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000002757 morpholinyl group Chemical group 0.000 claims description 3
125000003386 piperidinyl group Chemical group 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 2
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims description 2
239000008194 pharmaceutical composition Substances 0.000 claims description 2
AOAQFGRPXBJZPI-UHFFFAOYSA-N 7-(4-hydroxypentoxy)-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical group N1=C2NC(=O)NC2=CC2=CC(OCCCC(O)C)=CC=C21 AOAQFGRPXBJZPI-UHFFFAOYSA-N 0.000 claims 2
CXKZVQGXPZXMLT-UHFFFAOYSA-N 7-[3-(benzenesulfonyl)propoxy]-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical group C=1C=C2N=C3NC(=O)NC3=CC2=CC=1OCCCS(=O)(=O)C1=CC=CC=C1 CXKZVQGXPZXMLT-UHFFFAOYSA-N 0.000 claims 2
JAODEWCDRHAJPF-UHFFFAOYSA-N 7-[4-(1-cyclohexyltetrazol-5-yl)butoxy]-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical group C=1C=C2N=C3NC(=O)NC3=CC2=CC=1OCCCCC1=NN=NN1C1CCCCC1 JAODEWCDRHAJPF-UHFFFAOYSA-N 0.000 claims 2
PSFRCKHLCWZSJR-UHFFFAOYSA-N 7-[4-(benzenesulfonyl)butoxy]-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical group C=1C=C2N=C3NC(=O)NC3=CC2=CC=1OCCCCS(=O)(=O)C1=CC=CC=C1 PSFRCKHLCWZSJR-UHFFFAOYSA-N 0.000 claims 2
125000005322 morpholin-1-yl group Chemical group 0.000 claims 2
AUZJVEDTLNZEHH-UHFFFAOYSA-N n-cyclohexyl-4-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxy]butanamide Chemical group C=1C=C2N=C3NC(=O)NC3=CC2=CC=1OCCCC(=O)NC1CCCCC1 AUZJVEDTLNZEHH-UHFFFAOYSA-N 0.000 claims 2
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
NEXQSNFNHKOAMU-UHFFFAOYSA-N 1-methyl-7-(4-oxo-4-piperidin-1-ylbutoxy)-3h-imidazo[4,5-b]quinolin-2-one Chemical group C=1C=C2N=C3NC(=O)N(C)C3=CC2=CC=1OCCCC(=O)N1CCCCC1 NEXQSNFNHKOAMU-UHFFFAOYSA-N 0.000 claims 1
YVEQUTSPFYJJAS-UHFFFAOYSA-N 3-tert-butyl-5-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxymethyl]-1,3-oxazolidin-2-one Chemical group O1C(=O)N(C(C)(C)C)CC1COC1=CC=C(N=C2C(NC(=O)N2)=C2)C2=C1 YVEQUTSPFYJJAS-UHFFFAOYSA-N 0.000 claims 1
VDJBMWZCELLWPP-UHFFFAOYSA-N 4-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxy]-n-pentan-3-ylbutanamide Chemical group N1=C2NC(=O)NC2=CC2=CC(OCCCC(=O)NC(CC)CC)=CC=C21 VDJBMWZCELLWPP-UHFFFAOYSA-N 0.000 claims 1
OGIFXNGAJSAHFH-UHFFFAOYSA-N 5-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxymethyl]-3-propan-2-yl-1,3-oxazolidin-2-one Chemical group O1C(=O)N(C(C)C)CC1COC1=CC=C(N=C2C(NC(=O)N2)=C2)C2=C1 OGIFXNGAJSAHFH-UHFFFAOYSA-N 0.000 claims 1
CZDOWLCKYCPNMU-UHFFFAOYSA-N 7-(4-oxopentoxy)-1,3-dihydroimidazo[4,5-b]quinolin-2-one Chemical group N1=C2NC(=O)NC2=CC2=CC(OCCCC(=O)C)=CC=C21 CZDOWLCKYCPNMU-UHFFFAOYSA-N 0.000 claims 1
RFPQEXNUIMCZDQ-UHFFFAOYSA-N ac1ne2g0 Chemical compound CCC[CH2-] RFPQEXNUIMCZDQ-UHFFFAOYSA-N 0.000 claims 1
230000000747 cardiac effect Effects 0.000 claims 1
229940125782 compound 2 Drugs 0.000 claims 1
FYTROBAKOHFNCC-UHFFFAOYSA-N ethyl 1-[4-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxy]butanoyl]piperidine-4-carboxylate Chemical group C1CC(C(=O)OCC)CCN1C(=O)CCCOC1=CC=C(N=C2C(NC(=O)N2)=C2)C2=C1 FYTROBAKOHFNCC-UHFFFAOYSA-N 0.000 claims 1
PZVFRCCIJOLDRB-UHFFFAOYSA-N imidazo[4,5-b]quinolin-2-one Chemical compound C1=CC=CC2=NC3=NC(=O)N=C3C=C21 PZVFRCCIJOLDRB-UHFFFAOYSA-N 0.000 claims 1
QJCPQIHEKQJMJL-UHFFFAOYSA-N methyl 4-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxy]butanoate Chemical group N1=C2NC(=O)NC2=CC2=CC(OCCCC(=O)OC)=CC=C21 QJCPQIHEKQJMJL-UHFFFAOYSA-N 0.000 claims 1
DHHNFBRHDIGAHC-UHFFFAOYSA-N methyl 5-[(2-oxo-1,3-dihydroimidazo[4,5-b]quinolin-7-yl)oxy]pentanoate Chemical group N1=C2NC(=O)NC2=CC2=CC(OCCCCC(=O)OC)=CC=C21 DHHNFBRHDIGAHC-UHFFFAOYSA-N 0.000 claims 1
CVZAAYRCMFKBOJ-UHFFFAOYSA-N n-cycloheptyl-n-methyl-4-[(1-methyl-2-oxo-3h-imidazo[4,5-b]quinolin-7-yl)oxy]butanamide Chemical group C=1C=C2N=C3NC(=O)N(C)C3=CC2=CC=1OCCCC(=O)N(C)C1CCCCCC1 CVZAAYRCMFKBOJ-UHFFFAOYSA-N 0.000 claims 1
NAPKHDRXTZVUOK-UHFFFAOYSA-N n-cycloheptyl-n-methyl-5-[(1-methyl-2-oxo-3h-imidazo[4,5-b]quinolin-7-yl)oxy]pentanamide Chemical group C=1C=C2N=C3NC(=O)N(C)C3=CC2=CC=1OCCCCC(=O)N(C)C1CCCCCC1 NAPKHDRXTZVUOK-UHFFFAOYSA-N 0.000 claims 1
SFVRSCDYQRBUBX-UHFFFAOYSA-N n-cyclohexyl-n-methyl-5-[(1-methyl-2-oxo-3h-imidazo[4,5-b]quinolin-7-yl)oxy]pentanamide Chemical group C=1C=C2N=C3NC(=O)N(C)C3=CC2=CC=1OCCCCC(=O)N(C)C1CCCCC1 SFVRSCDYQRBUBX-UHFFFAOYSA-N 0.000 claims 1
125000003118 aryl group Chemical group 0.000 description 158
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 116
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 112
239000000203 mixture Substances 0.000 description 89
238000004458 analytical method Methods 0.000 description 80
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 73
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 68
239000000243 solution Substances 0.000 description 57
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
238000005481 NMR spectroscopy Methods 0.000 description 43
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
239000000460 chlorine Substances 0.000 description 29
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 25
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 24
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
239000002904 solvent Substances 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
239000012265 solid product Substances 0.000 description 21
229910052740 iodine Inorganic materials 0.000 description 20
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 19
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 19
239000011630 iodine Substances 0.000 description 19
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 17
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 17
238000002425 crystallisation Methods 0.000 description 17
230000008025 crystallization Effects 0.000 description 17
238000001914 filtration Methods 0.000 description 17
238000010992 reflux Methods 0.000 description 17
238000012360 testing method Methods 0.000 description 17
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
230000036961 partial effect Effects 0.000 description 15
239000000047 product Substances 0.000 description 14
150000003254 radicals Chemical class 0.000 description 14
239000011734 sodium Substances 0.000 description 14
229910052708 sodium Inorganic materials 0.000 description 14
238000011282 treatment Methods 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
238000005984 hydrogenation reaction Methods 0.000 description 13
239000005909 Kieselgur Substances 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 12
235000019345 sodium thiosulphate Nutrition 0.000 description 12
208000010110 spontaneous platelet aggregation Diseases 0.000 description 12
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 11
238000000354 decomposition reaction Methods 0.000 description 11
230000000694 effects Effects 0.000 description 11
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
229910000041 hydrogen chloride Inorganic materials 0.000 description 11
230000005764 inhibitory process Effects 0.000 description 11
239000003921 oil Substances 0.000 description 11
PNQYQNIOVAYJJG-UHFFFAOYSA-N 5-diethoxyphosphorylimidazolidine-2,4-dione Chemical compound CCOP(=O)(OCC)C1NC(=O)NC1=O PNQYQNIOVAYJJG-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
150000007513 acids Chemical class 0.000 description 10
239000000538 analytical sample Substances 0.000 description 10
239000003795 chemical substances by application Substances 0.000 description 10
229910000029 sodium carbonate Inorganic materials 0.000 description 10
CMWKITSNTDAEDT-UHFFFAOYSA-N 2-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=CC=C1C=O CMWKITSNTDAEDT-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzenecarboxaldehyde Natural products O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 9
239000000543 intermediate Substances 0.000 description 9
239000012071 phase Substances 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
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 8
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
XLYPHUGUKGMURE-UHFFFAOYSA-N 5-hydroxy-2-nitrobenzaldehyde Chemical compound OC1=CC=C([N+]([O-])=O)C(C=O)=C1 XLYPHUGUKGMURE-UHFFFAOYSA-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
239000000284 extract Substances 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000000126 substance Substances 0.000 description 8
210000004623 platelet-rich plasma Anatomy 0.000 description 7
239000000523 sample Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
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 6
125000004429 atom Chemical group 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
229940079593 drug Drugs 0.000 description 6
238000000338 in vitro Methods 0.000 description 6
230000000144 pharmacologic effect Effects 0.000 description 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
238000001556 precipitation Methods 0.000 description 6
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BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
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125000006225 propoxyethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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239000003998 snake venom Substances 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
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235000010413 sodium alginate Nutrition 0.000 description 1
239000000661 sodium alginate Substances 0.000 description 1
229940005550 sodium alginate Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
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239000003760 tallow Substances 0.000 description 1
239000008399 tap water Substances 0.000 description 1
235000020679 tap water Nutrition 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
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238000002054 transplantation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
BDZBKCUKTQZUTL-UHFFFAOYSA-N triethyl phosphite Chemical compound CCOP(OCC)OCC BDZBKCUKTQZUTL-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
238000001665 trituration Methods 0.000 description 1
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230000002792 vascular Effects 0.000 description 1
230000002861 ventricular Effects 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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229910052727 yttrium Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- 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

Landscapes

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)
Plural Heterocyclic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

LU86896A 1986-05-23 1987-05-22 Composes derives de l'imidazoquinolinylether,et leur procede de preparation LU86896A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US86681386		1986-05-23
US06/866,813 US4775674A (en)	1986-05-23	1986-05-23	Imidazoquinolinylether derivatives useful as phosphodiesterase and blood aggregation inhibitors

Publications (1)

Publication Number	Publication Date
LU86896A1 true LU86896A1 (fr)	1988-01-20

Family

ID=25348473

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU86896A LU86896A1 (fr)	1986-05-23	1987-05-22	Composes derives de l'imidazoquinolinylether,et leur procede de preparation

Country Status (24)

Country	Link
US (1)	US4775674A (it)
JP (1)	JPS62283972A (it)
KR (1)	KR900008567B1 (it)
AT (1)	AT392790B (it)
AU (1)	AU603577B2 (it)
BE (1)	BE1002033A4 (it)
CA (1)	CA1289137C (it)
CH (1)	CH675246A5 (it)
DE (1)	DE3717291A1 (it)
DK (1)	DK166084C (it)
ES (1)	ES2005588A6 (it)
FI (1)	FI86723C (it)
FR (1)	FR2603586B1 (it)
GB (1)	GB2190676B (it)
GR (1)	GR870803B (it)
HU (1)	HU197570B (it)
IL (1)	IL82612A0 (it)
IT (1)	IT1205031B (it)
LU (1)	LU86896A1 (it)
NL (1)	NL8701226A (it)
NZ (1)	NZ220345A (it)
PT (1)	PT84938B (it)
SE (1)	SE465163B (it)
ZA (1)	ZA873583B (it)

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1986
- 1986-05-23 US US06/866,813 patent/US4775674A/en not_active Expired - Fee Related
1987
- 1987-05-15 AU AU72993/87A patent/AU603577B2/en not_active Ceased
- 1987-05-18 NZ NZ220345A patent/NZ220345A/xx unknown
- 1987-05-19 ZA ZA873583A patent/ZA873583B/xx unknown
- 1987-05-19 GB GB8711839A patent/GB2190676B/en not_active Expired - Fee Related
- 1987-05-20 FI FI872220A patent/FI86723C/fi not_active IP Right Cessation
- 1987-05-21 IL IL82612A patent/IL82612A0/xx not_active IP Right Cessation
- 1987-05-21 GR GR870803A patent/GR870803B/el unknown
- 1987-05-22 PT PT84938A patent/PT84938B/pt unknown
- 1987-05-22 NL NL8701226A patent/NL8701226A/nl not_active Application Discontinuation
- 1987-05-22 JP JP62125642A patent/JPS62283972A/ja active Pending
- 1987-05-22 AT AT1320/87A patent/AT392790B/de not_active IP Right Cessation
- 1987-05-22 DK DK263587A patent/DK166084C/da active
- 1987-05-22 SE SE8702158A patent/SE465163B/sv not_active IP Right Cessation
- 1987-05-22 FR FR878707252A patent/FR2603586B1/fr not_active Expired - Fee Related
- 1987-05-22 CA CA000537720A patent/CA1289137C/en not_active Expired - Fee Related
- 1987-05-22 BE BE8700581A patent/BE1002033A4/fr not_active IP Right Cessation
- 1987-05-22 IT IT20650/87A patent/IT1205031B/it active
- 1987-05-22 HU HU872295A patent/HU197570B/hu not_active IP Right Cessation
- 1987-05-22 ES ES8701506A patent/ES2005588A6/es not_active Expired
- 1987-05-22 DE DE19873717291 patent/DE3717291A1/de not_active Withdrawn
- 1987-05-22 LU LU86896A patent/LU86896A1/fr unknown
- 1987-05-22 KR KR1019870005066A patent/KR900008567B1/ko not_active Expired
- 1987-05-25 CH CH2018/87A patent/CH675246A5/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
HUT43602A (en)	1987-11-30
NL8701226A (nl)	1987-12-16
US4775674A (en)	1988-10-04
ES2005588A6 (es)	1989-03-16
DK263587D0 (da)	1987-05-22
FR2603586B1 (fr)	1990-12-28
GB2190676A (en)	1987-11-25
IT1205031B (it)	1989-03-10
IL82612A0 (en)	1987-11-30
NZ220345A (en)	1990-10-26
FI872220L (fi)	1987-11-24
ATA132087A (de)	1990-11-15
DK166084B (da)	1993-03-08
PT84938A (en)	1987-06-01
IT8720650A0 (it)	1987-05-22
PT84938B (pt)	1990-02-08
FI86723B (fi)	1992-06-30
SE8702158D0 (sv)	1987-05-22
BE1002033A4 (fr)	1990-05-29
DK263587A (da)	1987-11-24
FR2603586A1 (fr)	1988-03-11
AU7299387A (en)	1987-11-26
KR870011137A (ko)	1987-12-21
AU603577B2 (en)	1990-11-22
HU197570B (en)	1989-04-28
JPS62283972A (ja)	1987-12-09
GB2190676B (en)	1990-05-30
GB8711839D0 (en)	1987-06-24
FI872220A0 (fi)	1987-05-20
CH675246A5 (it)	1990-09-14
KR900008567B1 (ko)	1990-11-24
AT392790B (de)	1991-06-10
DK166084C (da)	1993-08-02
CA1289137C (en)	1991-09-17
GR870803B (en)	1987-09-24
ZA873583B (en)	1988-04-27
SE8702158L (sv)	1987-11-24
SE465163B (sv)	1991-08-05
DE3717291A1 (de)	1987-11-26
FI86723C (fi)	1992-10-12

Legal Events

Date	Code	Title	Description
1987-05-22	DT	Application date
1991-06-07	TA	Annual fee

Publication	Publication Date	Title
LU86896A1 (fr)	1988-01-20	Composes derives de l'imidazoquinolinylether,et leur procede de preparation
FR2581065A1 (fr)	1986-10-31	Agents cardiotoniques et antithrombogeniques d'imidazoquinoline et leur procede de preparation
EP0385850A2 (fr)	1990-09-05	Nouveaux dérivés de benzimidazoles et azabenzimidazoles, leurs procédés de préparation, intermédiaires de synthèse, compositions pharmaceutiques les contenant, utiles notamment pour le traitement des maladies cardiovasculaires, et les ulcères duodénaux
EP0010029B1 (fr)	1982-11-17	Ellipticines substituées en position 1 par une chaîne polyaminée, leur synthèse et médicaments les contenant
FI93013B (fi)	1994-10-31	Menetelmä terapeuttisesti käyttökelpoisten pyridopyridatsinonijohdannaisten valmistamiseksi
US4337258A (en)	1982-06-29	2,4-Dioxo-4-substituted-1-butanoic acid derivatives useful in treating urinary tract calcium oxalate lithiasis
EP0018857B1 (fr)	1983-01-19	Pyrimido et imidazo-pyrido-indole-diones, leur préparation et leur application en thérapeutique
FR2527608A1 (fr)	1983-12-02	Nouveaux composes heterocycliques, leur preparation et leur utilisation comme medicaments
MC1221A1 (fr)	1979-07-20	Derives de l'imidazole et leurs sels,leur synthese et leurs produits intermediaires,et preparation de compositions pharmaceutiques contenant ces substances
CH650254A5 (fr)	1985-07-15	Quinolones, leurs procedes de preparation et compositions therapeutiques les contenant.
JPH03502690A (ja)	1991-06-20	ドーパミン‐β‐ヒドロキシラーゼ抑制剤
FR2536072A1 (fr)	1984-05-18	Nouveaux derives de la quinazoline, leur preparation et leur utilisation comme medicaments
EP0234970B1 (fr)	1991-04-17	Dérivés d'acylaminométhyl-3 imidazo[1,2-a]pyridines, leur préparation et leur application en thérapeutique
EP0233800B1 (fr)	1990-02-28	Dérivés d'imidazo[1,2-a]quinoléines, leur préparation et leur application en thérapeutique
EP0231138B1 (fr)	1990-04-18	Dérivés d'acylaminométhyl-1imidazo [1,2-a] quinoléines, leur préparation et leur application en thérapeutique
JPS63500518A (ja)	1988-02-25	多環式キノリン、ナフチリジンおよびピラジノピリジン誘導体
JPH01279864A (ja)	1989-11-10	新規の１，２―ジヒドロピリド〔３，４―ｂ〕―ピラジン類製造用の中間体
US4226773A (en)	1980-10-07	Pyrazolyl amino imidazolines as diuretic agents
US3715367A (en)	1973-02-06	Substituted 2 -(2-imidazolin-2-ylthio)acetophenones
FR2593181A1 (fr)	1987-07-24	Derives d'acylaminomethyl-3 imidazo(1,2-a)pyridines, leur preparation et leur application en therapeutique
BE883963A (fr)	1980-12-23	Derives du benzimidazole et compositions pharmaceutiques les contenant
FR2525218A1 (fr)	1983-10-21	Nouveaux derives du benzimidazole, leur preparation et les medicaments qui les contiennent
BE896159A (fr)	1983-09-15	1h-pyrazolo (1,5,-a) pyrimidines substituees et leur preparation
FR2462436A1 (fr)	1981-02-13	Nouvelles 2-(5-pyrazolylamino)-2-imidazolines, utiles notamment comme agents anti-inflammatoires, et compositions pharmaceutiques les contenant
RU2173316C2 (ru)	2001-09-10	Новые гетероциклические производные и их фармацевтическое использование